FUSED HETEROCYCLIC COMPOUND AND USE FOR PEST CONTROL THEREOF

TECHNICAL FIELD

The present invention relates to a certain fused heterocyclic compound and use for pest control thereof.

BACKGROUND ART

For controlling pests, various compounds have heretofore been developed and used practically.

Certain fused heterocyclic compounds are known (see, Patent Literature 1).

CITATION LIST
Patent Literature

Patent Literature 1: JP-A-01-501473

SUMMARY OF INVENTION
Technical Problem

An object of the present invention is to provide a compound having an excellent activity of controlling pests and a method of controlling pests using the compound.

Solution to Problem

The present inventors have studied so as to resolve the above problem and found that a fused heterocyclic compound of the following formula (1) has an excellent activity of controlling pests, thus leading to the present invention.

That is, the present invention provides:

[1] A fused heterocyclic compound of the formula (1):

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wherein:

A¹represents —NR⁸—, an oxygen atom, or a sulfur atom;

A²represents a nitrogen atom or ═CR⁹—;

A³represents a nitrogen atom or ═CR¹⁰—;

R¹represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, or a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y;

R², R³, R⁴, and R⁵are same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, —OR¹¹, —S(O)_mR¹¹, —NR¹¹R¹², —CO₂R¹¹, —C(O)R¹¹, a cyano group, a nitro group, a halogen atom, —SF₅, or a hydrogen atom, provided that at least two of R², R³, R⁴, and R⁵represent a hydrogen atom;

R⁶and R⁷are same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, a phenyl group optionally having one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, —OR¹¹, S(O)_mR¹¹, —S(O)₂NR¹¹R¹², —NR¹¹R¹², —NR¹¹CO₂R¹², —NR¹¹C(O)R¹², —CO₂R¹¹, —C(O)R¹¹, a cyano group, a nitro group, a halogen atom, —SF₅, or a hydrogen atom;

R⁸represents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group W, —CO₂R¹¹, —C(O)R¹¹, a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y, or a hydrogen atom;

R⁹and R¹⁰are same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, NR¹¹R¹², —CO₂R¹¹, —C(O)R¹¹, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R¹¹and R¹²are same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom; and

m represents 0, 1, or 2; and n represents 0, 1, or 2;

(except in cases as follows: both R⁶and R⁷are a hydrogen atom; in —S(O)_mR¹¹, when m is 1 or 2, R¹¹is a hydrogen atom; and when A¹represents —NH— or —N(CH₃)—, A²and A³represent ═CH—, R¹represents a methyl group, R², R³, R⁴, and R⁵represent a hydrogen atom, and n is 0, 1, or 2, R⁶and R⁷are same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, a phenyl group optionally having one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, —OR¹¹, —S(O)_mR¹¹, S(O)₂NR¹¹R¹², —NR¹¹R¹², —NR¹¹—CO₂R¹², —NR¹¹C(O)_R¹², —CO₂H, —C(O)R¹¹, a cyano group, a nitro group, a bromine atom, an iodine atom, —SF₅or a hydrogen atom)

the Group X consists of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C2-C6 alkenyloxy group optionally having one or more halogen atoms, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a cyano group, a hydroxy group, and a halogen atom;

the Group Y consists of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C2-C6 alkenyloxy group optionally having one or more halogen atoms, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a hydroxy group, and a halogen atom;

the Group Z consists of a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, a C2-C8 dialkylamino group optionally having one or more halogen atoms, a halogen atom, a cyano group, and a nitro group; and

the Group W consists of a C1-C6 alkoxy group optionally having one or more halogen atoms, a C2-C6 alkenyloxy group optionally having one or more halogen atoms, a C2-C6 alkynyloxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C3-C6 cycloalkyl group optionally having one or more halogen atoms, a halogen atom, a cyano group, and a hydroxy group (hereinafter referred to as the present compound);

[2] The fused heterocyclic compound according to the above [1] wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —(O)_mR¹¹, —NR¹¹R¹², a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

[3] The fused heterocyclic compound according to the above [1] or [2] wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, a halogen atom, or a hydrogen atom;

[4] The fused heterocyclic compound according to any one of the above [1]-[3] wherein A²is ═CH—;

[5] The fused heterocyclic compound according to any one of the above [1]-[4] wherein A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

[6] The fused heterocyclic compound according to any one of the above [1]-[4] wherein A³is a nitrogen atom;

[7] The fused heterocyclic compound according to any one of the above [1]-[6] wherein R², R⁴, and R⁵are same or different and are independently a hydrogen atom or a halogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, a halogen atom, or a hydrogen atom;

[8] The fused heterocyclic compound according to any one of the above [1]-[7] wherein A¹is —NR⁸—, and R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a cyclopropyl group;

[9] The fused heterocyclic compound according to any one of the above [1]-[7] wherein A¹is —NR⁸—, and R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group;

[10] The fused heterocyclic compound according to any one of the above [1]-[7] wherein A¹is an oxygen atom;

[11] The fused heterocyclic compound according to any one of the above [1]-[7] wherein A¹is a sulfur atom;

[12] The fused heterocyclic compound according to the above [1] which is represented by the formula (1-1):

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wherein:

A^1arepresents —NR^8a— or a sulfur atom;

A^3arepresents a nitrogen atom or ═CR^10a—;

R^1arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

R^2a, R^4a, and R^5aare same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom;

R^3arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11a, a halogen atom, or a hydrogen atom;

R^6arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11a, —S(O)_mR^11a, a bromine atom, or an iodine atom;

R^8arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

R^10arepresents a halogen atom or a hydrogen atom;

R^11arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms; and

m represents 0, 1, or 2, and n represents 0, 1, or 2; [13] The fused heterocyclic compound according to the above [12] wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a methyl group, A^3ais a nitrogen atom, R^1ais an ethyl group, R^2a, R^4a, and R^5aare same or different and are independently a halogen atom or a hydrogen atom, R^3ais a trifluoromethyl group, a halogen atom, or a hydrogen atom, and R^6ais a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

[14] A pest controlling composition which comprises the fused heterocyclic compound according to any one of the above [1]-[13] and an inert carrier; and

[15] A method of controlling pests which comprises applying an effective amount of the fused heterocyclic compound according to any one of the above [1]-[13] to pests or habitats of pests.

Effect of Invention

The present compound has an excellent activity of controlling pests and is useful as an active ingredient of a pest controlling agent.

DESCRIPTION OF EMBODIMENTS

Various substituents used in the present specification will be illustrated by way of examples.

In the present invention, the “halogen atom” includes a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.

In the present compound, examples of the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X” include a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group X such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, a tert-butyloxymethyl group, a 2-methoxyethyl group, a 2-ethoxyethyl group, a 2-propyloxyethyl group, a 2-isopropyloxyethyl group, a 2-butyloxyethyl group, a 2-sec-butyloxyethyl group, a 2-tert-butyloxyethyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a methylsulfanylethyl group, an ethylsulfanylethyl group, a methylsulfinylethyl group, and a methylsulfonylethyl group, a methoxycarbonylethyl group, a cyanomethyl group, a cyclopropylmethyl group, and a cyclobutylmethyl group;

a C2-C6 alkenyl group optionally having one or more atoms or groups selected from Group X such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoroallyl group, and a pentafluoroallyl group; and

a C2-C6 alkynyl group optionally having one or more atoms or groups selected from Group X such as an ethinyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, and a 4,4,4-trifluoro-2-butynyl group.

In the present compound, examples of the “C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a 1-cyclohexenyl group, a 2-cyclohexenyl group, a 3-cyclohexenyl group, a 1-methylcyclohexyl group, a 2-methylcyclohexyl group, a 3-methylcyclohexyl group, a 4-methylcyclohexyl group, a 2-methoxycyclohexyl group, a 3-methoxycyclohexyl group, a 4-methoxycyclohexyl group, a 1-fluorocyclohexyl group, a 2-fluorocyclohexyl group, a 3-fluorocyclohexyl group, and a 4-fluorocyclohexyl group.

In the present compound, examples of the “C1-C6 chain hydrocarbon group optionally having one or more halogen atoms” include a C1-C6 alkyl group optionally having one or more halogen atoms such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, and a heptafluoroisopropyl group;

a C2-C6 alkenyl group optionally having one or more halogen atoms such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoroallyl group, and a pentafluoroallyl group; and

a C2-C6 alkynyl group optionally having one or more halogen atoms such as an ethinyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, and a 4,4,4-trifluoro-2-butynyl group.

In the present compound, examples of the “phenyl group optionally having one or more atoms or groups selected from Group Z” include a phenyl group, a 2-fluorophenyl group, a 3-fluorophenyl group, a 4-fluorophenyl group, a 2,3-difluorophenyl group, a 2,4-difluorophenyl group, a 2,5-difluorophenyl group, a 2,6-difluorophenyl group, a 3,4-difluorophenyl group, a 3,5-difluorophenyl group, a 2,3,4,5,6-pentafluorophenyl group, a 2-chlorophenyl group, a 3-chlorophenyl group, a 4-chlorophenyl group, a 2-bromophenyl group, a 3-bromophenyl group, a 4-bromophenyl group, a 2-iodophenyl group, a 3-iodophenyl group, a 4-iodophenyl group, a 2-trifluoromethylphenyl group, a 3-trifluoromethylphenyl group, a 4-trifluoromethylphenyl group, a 2-trifluoromethoxyphenyl group, a 3-trifluoromethoxyphenyl group, a 4-trifluoromethoxyphenyl group, a 2-trifluoromethylsulfanylphenyl group, a 3-trifluoromethylsulfanylphenyl group, a 4-trifluoromethylsulfanylphenyl group, a 4-methoxycarbonylphenyl group, a 4-nitrophenyl group, a 4-cyanophenyl group, a 4-methylaminophenyl group, a 4-dimethylaminophenyl group, a 4-methylsulfinylphenyl group, a 4-methylsulfonylphenyl group, a 4-acetylphenyl group, and 4-methoxycarbonylphenyl group.

In the present compound, the “heterocyclic group” in the “5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z” represents a heterocyclic residue. Examples of “5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z” include a 5-membered saturated heterocyclic group optionally having one or more atoms or groups selected from Group Z such as a pyrrolidin-1-yl group and a tetrahydrofuran-2-yl group; and

a 5-membered unsaturated heterocyclic group optionally having one or more atoms or groups selected from Group Z such as a 2-pyrrolyl group, a 2-furyl group, a 3-furyl group, a 5-pyrazolyl group, a 4-pyrazolyl group, a 1-pyrrolyl group, a 1-methyl-2-pyrrolyl group, a 5-bromo-2-furyl group, a 5-nitro-2-furyl group, a 2-methyl-3-furyl group, a 2,5-dimethyl-3-furyl group, a 2,4-dimethyl-3-furyl group, a 5-methyl-2-thienyl group, a 3-methyl-2-thienyl group, a 1-methyl-3-trifluoromethyl-5-pyrazolyl group, a 5-chloro-1,3-dimethyl-4-pyrazolyl group, a pyrazol-1-yl group, a 3-chloro-pyrazol-1-yl group, a 3-bromopyrazol-1-yl group, a 4-chloropyrazol-1-yl group, a 4-bromopyrazol-1-yl group, a imidazol-1-yl group, a pyrrol-1-yl group, a 1,2,4-triazol-1-yl group, a 3-chloro-1,2,4-triazol-1-yl group, a 1,2,3,4-tetrazol-1-yl group, a 1,2,3,5-tetrazol-1-yl group, a 2-thienyl group, a 3-thienyl group, a 3-trifluoromethyl-1,2,4-triazol-1-yl group, and a 4-trifluoromethylpyrazol-1-yl group.

In the present compound, the “heterocyclic group” in the “6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z” represents a heterocyclic residue. Examples of the “6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z” include a 6-membered saturated heterocyclic group optionally having one or more atoms or groups selected from Group Z such as a piperidyl group, a morpholinyl group, and a thiomorpholinyl group; and

a 6-membered aromatic heterocyclic group optionally having one or more atoms or groups selected from Group Z such as a pyrazinyl group, a 2-pyrimidyl group, a 4-pyrimidyl group, a 5-pyrimidyl group, a 2-pyridyl group, a 3-pyridyl group, a 4-pyridyl group, a 3-fluoro-2-pyridyl group, a 4-fluoro-2-pyridyl group, a 5-fluoro-2-pyridyl group, a 6-fluoro-2-pyridyl group, a 2-pyrimidyl group, and a 5-trifluoromethylpyridin-2-yl group.

In the present compound, the “C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group W” include a C1-C6 alkyl group optionally having one or more atoms or groups selected from Group W such as a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a sec-butyl group, a tert-butyl group, a pentyl group, a neopentyl group, a hexyl group, a trifluoromethyl group, a trichloromethyl group, a 2-fluoroethyl group, a 2,2-difluoroethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a methoxymethyl group, an ethoxymethyl group, a propyloxymethyl group, an isopropyloxymethyl group, a butyloxymethyl group, a sec-butyloxymethyl group, an isobutyloxymethyl group, a tert-butyloxymethyl group, a methoxyethyl group, an ethoxyethyl group, a propyloxyethyl group, an isopropyloxyethyl group, a butyloxyethyl group, a sec-butyloxyethyl group, an isobutyloxyethyl group, a tert-butyloxyethyl group, a methylsulfanylethyl group, an ethylsulfanylethyl group, a methylsulfinylethyl group, a methylsulfonylethyl group, a methoxycarbonylmethyl group, a methoxycarbonylethyl group, a cyclopropylmethyl group, and a cyclohexylmethyl group;

a C2-C6 alkenyl group optionally having one or more atoms or groups selected from Group W such as a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-methylvinyl group, a 2-methyl-1-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-pentenyl group, a 1-hexenyl group, a 1,1-difluoroallyl group, and a pentafluoroallyl group; and

a C2-C6 alkynyl group optionally having one or more atoms or groups selected from Group W such as an ethinyl group, a propargyl group, a 2-butynyl group, a 3-butynyl group, a 1-pentynyl group, a 1-hexynyl group, and a 4,4,4-trifluoro-2-butynyl group.

In the present compound, examples of the “C1-C6 alkylsulfanyl group optionally having one or more halogen atoms” include a methylsulfanyl group, an ethylsulfanyl group, a propylsulfanyl group, an isopropylsulfanyl group, a butylsulfanyl group, a pentylsulfanyl group, a hexylsulfanyl group, a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, and a pentafluoroethylsulfanyl group.

In the present compound, examples of the “C1-C6 alkylsulfinyl group optionally having one or more halogen atoms” include a methylsulfinyl group, an ethylsulfinyl group, a propylsulfinyl group, an isopropylsulfinyl group, a butylsulfinyl group, a pentylsulfinyl group, a hexylsulfinyl group, a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, and a pentafluoroethylsulfinyl group.

In the present compound, examples of the “C1-C6 alkylsulfonyl group optionally having one or more halogen atoms” include a methylsulfonyl group, an ethylsulfonyl group, a propylsulfonyl group, an isopropylsulfonyl group, a butylsulfonyl group, a pentylsulfonyl group, a hexylsulfonyl group, a trifluoromethylsulfonyl group, a pentafluoroethylsulfonyl group.

In the present compound, examples of the “C1-C6 alkoxy group optionally having one or more halogen atoms” include a methoxy group, a trifluoromethoxy group, an ethoxy group, a 2,2,2-trifluoroethoxy group, a propyloxy group, an isopropyloxy group, a butyloxy group, an isobutyloxy group, a sec-butyloxy group, a tert-butyloxy group, a pentyloxy group, and a hexyloxy group.

In the present compound, examples of the “C2-C6 alkenyloxy group optionally having one or more halogen atoms” include a 2-propenyloxy group, a 2-methyl-2-propenyloxy group, a 2-butenyloxy group, a 3-butenyloxy group, a 2-pentenyloxy group, a 2-hexenyloxy group, a 3,3-difluoroallyloxy group, and a 3,3-dichloroallyloxy group.

In the present compound, examples of the “C2-C6 alkynyloxy group optionally having one or more halogen atoms” include a propargyloxy group, a 2-butynyloxy group, a 3-butynyloxy group, a 2-pentynyloxy group, a 2-hexynyloxy group, and a 4,4,4-trifluoro-2-butynyloxy group.

In the present compound, examples of the “C2-C6 alkylcarbonyl group optionally having one or more halogen atoms” include an acetyl group, a propionyl group, a propylcarbonyl group, a butylcarbonyl group, a pentylcarbonyl group, and a trifluoroacetyl group.

In the present compound, examples of the “C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms” include a methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, a butyloxycarbonyl group, a pentyloxycarbonyl group, a tert-butyloxycarbonyl group, and a 2,2,2-trifluoroethylcarbonyl group.

In the present compound, examples of the “C1-C6 alkylamino group optionally having one or more halogen atoms” include a methylamino group, an ethylamino group, a 2,2,2-trifluoroethylamino group, a propylamino group, an isopropylamino group, and a butylamino group.

In the present compound, examples of the “C2-C8 dialkylamino group optionally having one or more halogen atoms” include a dimethylamino group, a diethylamino group, a bis(2,2,2-trifluoroethyl)amino group, and a dipropylamino group.

In the present compound, examples of the “C3-C6 cycloalkyl group optionally having one or more halogen atoms” include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

In the present compound, examples of the “C1-C3 alkyl group having one or more a fluorine atoms” include a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a trichloromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

In the present compound, examples of the “C1-C3 alkoxy group having one or more a fluorine atoms” include a trifluoromethoxy group, a 2,2,2-trifluoroethoxy group, and a pentafluoroethoxy group.

In the present compound, examples of the “C1-C3 alkylsulfanyl group having one or more a fluorine atoms” include a trifluoromethylsulfanyl group, a 2,2,2-trifluoroethylsulfanyl group, a pentafluoroethylsulfanyl group, a heptafluoropropylsulfanyl group, and a heptafluoroisopropylsulfanyl group.

In the present compound, examples of the “C1-C3 alkylsulfinyl group having one or more a fluorine atoms” include a trifluoromethylsulfinyl group, a 2,2,2-trifluoroethylsulfinyl group, a pentafluoroethylsulfinyl group, a heptafluoropropylsulfinyl group, and a heptafluoroisopropylsulfinyl group.

In the present compound, examples of the “C1-C3 alkylsulfonyl group having one or more a fluorine atoms” include a trifluoromethylsulfonyl group, a 2,2,2-trifluoroethylsulfonyl group, a pentafluoroethylsulfonyl group, a heptafluoropropylsulfonyl group, and a heptafluoroisopropylsulfonyl group.

In the present compound, examples of the “C1-C3 alkyl group” include a methyl group, an ethyl group, a propyl group, and an isopropyl group.

In the present compound, examples of the “C1-C3 alkyl group optionally having one or more halogen atoms” include a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a 2,2,2-trifluoroethyl group, a 2,2,2-trichloroethyl group, a heptafluoropropyl group, and a heptafluoroisopropyl group.

Examples of the present compound include the following pyrimidine compounds.

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C2-C6 alkoxycarbonyl group, —CO₂R¹¹, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a methyl group;

A compound of the formula (1) wherein A¹is —NR⁸— or an oxygen atom, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C2-C6 alkoxycarbonyl group, —CO₂R¹¹, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, or a cyclopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group;

A compound of the formula (1) wherein A¹is an oxygen atom;

A compound of the formula (1) wherein A¹is a sulfur atom;

A compound of the formula (1) wherein A²is a nitrogen atom;

A compound of the formula (1) wherein A²is a nitrogen atom or ═CR⁹—, and R⁹is a C1-C3 chain hydrocarbon group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A²is a nitrogen atom or ═CR⁹—, and R⁹is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A²is a nitrogen atom or ═CR⁹—, and R⁹is a hydrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, and R⁹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, —NR¹¹R¹², —CO₂R¹¹, —C(O)R¹¹, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, and R⁹is a C1-C3 chain hydrocarbon group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, and R⁹is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, and R⁹is a hydrogen atom;

A compound of the formula (1) wherein A³is a nitrogen atom;

A compound of the formula (1) wherein A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a C1-C3 chain hydrocarbon group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A³is a nitrogen atom or ═CR¹⁰—, and R¹is a hydrogen atom;

A compound of the formula (1) wherein A³is ═CR¹⁰—, and R¹⁰is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, —NR¹¹R¹², —CO₂R¹¹, —C(O)R¹⁰, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A³is ═CR¹⁰—, and R¹⁰is a C1-C3 chain hydrocarbon group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein A³is ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A³is ═CR¹⁰—, and R¹⁰is a halogen atom;

A compound of the formula (1) wherein A³is ═CR¹⁰—, and R¹⁰is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C2-C6 alkoxycarbonyl group, —CO₂R¹¹, or a cyclopropyl group, A²is a nitrogen atom or ═CR⁹—, R⁹is a halogen atom or a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, or a cyclopropyl group, A²is a nitrogen atom or ═CR⁹—, R⁹is a halogen atom or a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, R⁸is a methyl group, A²is a nitrogen atom or ═CR⁹—, R⁹is a halogen atom or a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, R⁸is a methyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom; A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is an oxygen atom, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X;

A compound of the formula (1) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein R¹is a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y;

A compound of the formula (1) wherein R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, and a 2,2,2-trifluoroethyl group;

A compound of the formula (1) wherein R¹is a methyl group, an ethyl group, or a propyl group;

A compound of the formula (1) wherein R¹is an ethyl group;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —NR¹¹R¹², a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a methyl group, an ethyl group, a trifluoromethyl group, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a methoxy group, an ethoxy group, a trifluoromethoxy group, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently an amino group, a methylamino group, a dimethylamino group, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a cyano group or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a nitro group or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethoxy group, a pentafluoroethyl group, a methoxy group, a cyano group, a nitro group, or a hydrogen atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a C2-C6 alkylcarbonyl group optionally having one or more halogen atoms, a C2-C6 alkoxycarbonyl group optionally having one or more halogen atoms, a C1-C6 alkylamino group optionally having one or more halogen atoms, C2-C8 dialkylamino group optionally having one or more halogen atoms, an aldehyde group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a trifluoromethyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are a hydrogen atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a trifluoromethyl group;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group;

A compound of the formula (1) wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, —NR¹¹R¹², —CO₂R¹¹, —C(O)R¹¹, a cyano group, a nitro group, a halogen atom, or a hydrogen atom, and R¹¹and R¹²are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1) wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, a halogen atom, or a hydrogen atom, and R¹¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

A compound of the formula (1) wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms, an aldehyde group, a cyano group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, an aldehyde group, a cyano group, a halogen atom, or a hydrogen atom;

A compound of the formula (1) wherein R⁶and R⁷are same or different and are independently a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, or a halogen atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more halogen atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more a fluorine atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is −OR¹¹, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is —S(O)_mR¹¹, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, or a halogen atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a hydrogen atom, and R⁷is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom;

A compound of the formula (1) wherein R⁶is a bromine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a pentafluoroethyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethoxy group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethylsulfanyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethylsulfinyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a trifluoromethylsulfonyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a heptafluoroisopropyl group, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein n is 0;

A compound of the formula (1) wherein n is 1;

A compound of the formula (1) wherein n is 2;

A compound of the formula (1) wherein m is 0;

A compound of the formula (1) wherein m is 1;

A compound of the formula (1) wherein m is 2;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group, and R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a methoxymethyl group or an ethoxymethyl group, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, and R², R³, R⁴, and R⁵are a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R³, R⁴, and R⁵are a hydrogen atom, and R⁷is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, R¹⁰is a halogen atom or a hydrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, R¹⁰is a halogen atom or a hydrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, A²is a nitrogen atom or ═CR⁹—, A³is a nitrogen atom or ═CR¹⁰—, R¹is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X, R², R³, R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms, an aldehyde group, a cyano group, a halogen atom, or a hydrogen atom, R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a cyclopropyl group, R⁹and R¹⁰are same or different and are independently a halogen atom or a hydrogen atom, and R¹¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein A¹is —NR⁸—;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C6 chain hydrocarbon group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C6 alkyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a C1-C3 alkyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, an oxygen atom, or a sulfur atom, and R⁸is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C6 chain hydrocarbon group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C6 alkyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a C1-C3 alkyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, a cyclopropyl group, or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is an ethyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a propyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is an isopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methyl group or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, and R⁸is a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, and R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, and R⁸is a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A²is ═CR⁹—, A³is ═CR¹⁰—, and R⁹and R¹⁰are a hydrogen atom;

A compound of the formula (1) wherein A²is a nitrogen atom, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A²is ═CR⁹—, and A³is a nitrogen atom;

A compound of the formula (1) wherein A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A²is a nitrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, A²is ═CR⁹—, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is —NR⁸—, A²is a nitrogen atom, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is —NR⁸—, A²is ═CR⁹—, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, A²is a nitrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is an oxygen atom, A²is ═CR⁹—, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is an oxygen atom, A²is a nitrogen atom, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is an oxygen atom, A²is ═CR⁹—, and A³is a nitrogen atom; A compound of the formula (1) wherein A¹is an oxygen atom, A²is a nitrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is a nitrogen atom, and A³is ═CR¹⁰—;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is a nitrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, a cyclopropyl group, or a hydrogen atom, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, R⁸is a methyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, a cyclopropyl group, or a hydrogen atom, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, and A³is a nitrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, A²is ═CR⁹—, A³is ═CR¹⁰—, and R⁹and R¹⁰are a hydrogen atom;

A compound of the formula (1) wherein A¹is an oxygen atom, A²is ═CR⁹—, A³is ═CR¹⁰—, and R⁹and R¹⁰are a hydrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, A³is ═CR¹⁰—, and R⁹and R¹⁰are a hydrogen atom;

A compound of the formula (1) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more fluorine atoms;

A compound of the formula (1) wherein R¹is a C1-C6 chain hydrocarbon group;

A compound of the formula (1) wherein R¹is a C1-C6 alkyl group;

A compound of the formula (1) wherein R¹is a C1-C3 alkyl group;

A compound of the formula (1) wherein R¹is a C3-C6 alicyclic hydrocarbon group;

A compound of the formula (1) wherein R¹is a cyclopropyl group, a cyclobutyl group, or a cyclopentyl group;

A compound of the formula (1) wherein R¹is a methyl group;

A compound of the formula (1) wherein R¹is a propyl group;

A compound of the formula (1) wherein R¹is an isopropyl group;

A compound of the formula (1) wherein R¹is a trifluoromethyl group;

A compound of the formula (1) wherein R¹is a 2,2,2-trifluoroethyl group;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a phenyl group optionally having one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently —SF₅or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently a C1-C3 alkyl group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently —OR¹¹or a hydrogen atom;

A compound of the formula (1) wherein R², R³, R⁴, and R⁵are same or different and are independently —NR¹¹R¹²or a hydrogen atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, R³is a phenyl group optionally having one or more atoms or groups selected from Group Z, a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z, or a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, R³is a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a trifluoromethoxy group;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a fluorine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a chlorine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a bromine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is an iodine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 alkyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C3 alkyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 5-membered heterocyclic group optionally having one or more atoms or groups selected from Z group, or a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 6-membered heterocyclic group optionally having one or more atoms or groups selected from Group Z;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethoxy group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a fluorine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is an iodine atom;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, or a 3-chloro-5-trifluoromethyl-2-pyridyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 2-pyridyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 2-pyrimidyl group;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is —SF₅;

A compound of the formula (1) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethoxy group;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom;

A compound of the formula (1) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is an iodine atom;

A compound of the formula (1) wherein R⁶is a C1-C3 alkyl group having one or more fluorine atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C3 alkoxy group having one or more fluorine atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a halogen atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein R⁶is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1) wherein R⁶is —SF₅, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, R⁸is a C1-C6 alkyl group, A²is ═CR⁹—, A³is ═CR¹⁰—, R⁹and R¹⁰are a hydrogen atom, R¹is a C1-C3 alkyl group optionally having one or more fluorine atoms, R², R⁴, and R⁵are a hydrogen atom, R³is a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R⁶is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸— or a sulfur atom, R⁸is a C1-C6 alkyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom, R¹is a C1-C3 alkyl group optionally having one or more fluorine atoms, R², R⁴, and R⁵are a hydrogen atom, R³is a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R⁶is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom or ═CR¹⁰—, R¹⁰is a halogen atom or a hydrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, R⁷is a hydrogen atom, and n is 2;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group, A²is ═CR⁹—, A³is ═CR¹⁰—, R⁹and R¹⁰are a hydrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, A³is ═CR¹⁰—, R⁹and R¹⁰are a hydrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is —NR⁸—, R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1) wherein A¹is a sulfur atom, A²is ═CR⁹—, R⁹is a hydrogen atom, A³is a nitrogen atom, R¹is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

A compound of the formula (1-1)

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wherein;

A^1arepresents —NR^8a— or a sulfur atom;

A^3arepresents a nitrogen atom or ═CR^10a—;

R^1arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

R^2a, R^4a, and R^5aare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom;

R^6arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11a, a halogen atom, or a hydrogen atom;

R^6arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11a, —S(O)_mR^11a, a bromine atom, or an iodine atom;

R^8arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

R^10arepresents a halogen atom or a hydrogen atom;

R^11arepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, m represents 0, 1, or 2, and n represents 0, 1 or 2;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a methyl group, A^3ais a nitrogen atom, R^1ais an ethyl group, R^2a, R^4a, and R^5aare a halogen atom or a hydrogen atom, R^3ais a trifluoromethyl group, a halogen atom, or a hydrogen atom, and R^8ais a C1-C3 chain hydrocarbon group having one or more a fluorine atoms, a C1-C3 alkoxy group having one or more a fluorine atoms, a C1-C3 alkylsulfanyl group having one or more a fluorine atoms, a C1-C3 alkylsulfinyl group having one or more a fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more a fluorine atoms;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a methyl group, A^3ais a nitrogen atom, R^1ais an ethyl group, R^2a, R^4a, and R^5aare a hydrogen atom, R^3ais a chlorine atom, a bromine atom, a trifluoromethyl group, or a hydrogen atom, and R^6ais a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, and R^8ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a methyl group;

A compound of the formula (1-1) wherein A^1ais a sulfur atom;

A compound of the formula (1-1) wherein A^3ais a nitrogen atom or ═CR^10a—, and R^10ais a halogen atom or a hydrogen atom;

A compound of the formula (1-1) wherein A^3ais ═CR^{10a—, and R}^10ais a halogen atom or a hydrogen atom;

A compound of the formula (1-1) wherein A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, A^3ais a nitrogen atom or ═CR^10a—, and R^10ais a hydrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, A^3ais ═CR^10a—, and R^10ais a hydrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a methyl group, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, R^8ais a methyl group, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein A^1ais a sulfur atom, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein R^1ais a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1-1) wherein R^1ais an ethyl group;

A compound of the formula (1-1) wherein R^2a, R^4a, and R^5aare same or different and are independently a fluorine atom, a chlorine atom, or a hydrogen atom, and R^3ais a fluorine atom, a chlorine atom, a bromine atom, a methyl group, a trifluoromethyl group, or a hydrogen atom;

A compound of the formula (1-1) wherein R^2a, R^4a, and R^5aare a hydrogen atom, and R^3ais a fluorine atom, a chlorine atom, a bromine atom, a methyl group, or a trifluoromethyl group;

A compound of the formula (1-1) wherein R^6ais a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1-1) wherein R⁶⁸is a bromine atom;

A compound of the formula (1-1) wherein R^6ais an iodine atom;

A compound of the formula (1-1) wherein R^6ais a trifluoromethyl group;

A compound of the formula (1-1) wherein R^6ais a pentafluoroethyl group;

A compound of the formula (1-1) wherein R^6ais a heptafluoroisopropyl group;

A compound of the formula (1-1) wherein R^6ais a trifluoromethoxy group;

A compound of the formula (1-1) wherein R^6ais a trifluoromethylsulfanyl group;

A compound of the formula (1-1) wherein R^6ais a trifluoromethylsulfinyl group;

A compound of the formula (1-1) wherein R^6ais a trifluoromethylsulfonyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a C1-C3 alkyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais an ethyl group;

A compound of the formula (1-1) wherein is —NR^8a—, and R^8ais a propyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais an isopropyl group;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a methyl group or a hydrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a hydrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and R^8ais a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (1-1) wherein A^3ais ═CR^10a—, and R^10ais a hydrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and A^3ais ═CR^10a—;

A compound of the formula (1-1) wherein A^1ais a sulfur atom, and A^3ais ═CR^10a—;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a—, R^8ais a hydrogen atom group, and A^3ais a nitrogen atom;

A compound of the formula (1-1) wherein R^1ais a C1-C3 alkyl group;

A compound of the formula (1-1) wherein R^1ais a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group;

A compound of the formula (1-1) wherein R^1ais a methyl group;

A compound of the formula (1-1) wherein R^1ais a propyl group;

A compound of the formula (1-1) wherein R^2a, R^3a, R^4a, and R^5aare a hydrogen atom;

A compound of the formula (1-1) wherein R^6ais a halogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a C1-C6 alkyl group, A^3ais ═CR^10a—, R^10ais a hydrogen atom, R^1ais a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2a, R^4a, and R^5aare a hydrogen atom, R^3ais a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, and R^6ais a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1-1) wherein A^1ais —NR^8a— or a sulfur atom, R^8ais a C1-C6 alkyl group, A^3ais a nitrogen atom, R^1ais a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2a, R^4a, and R^5aare a hydrogen atom, R^1ais a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, and R^6ais a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1-0):

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wherein:

A^1jrepresents —NR^8j—, an oxygen atom, or a sulfur atom;

A^2jrepresents a nitrogen atom or ═CR^9j—;

A^3jrepresents a nitrogen atom or ═CR^10j—;

R^1jrepresents a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X^j, or a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y^j;

R^2j, R^3j, R^4j, and R^5jare same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11j, —NR^11jR^12j, a cyano group, a nitro group, a halogen atom, or a hydrogen atom: provided that at least two of R^2j, R^3j, R^4j, and R^5jrepresent a hydrogen atom;

R^6jand R⁷are same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms, —OR^11j, —S(O)_mR^11j, —NR^11jR^12j, —CO₂R^11j, —C(O)R^11j, an aldehyde group, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^8jrepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one —OR^11j, or a cyclopropyl group;

R^9jand R^10jare same or different and independently represent a C1-C3 chain hydrocarbon group, a halogen atom, or a hydrogen atom;

R^11jand R^12jare same or different and independently represent a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom; and

m represents 0, 1, or 2, and n represents 0, 1, or 2;

(except in cases as follows: both e and R⁷are a hydrogen atom; in —S(O)_mR^11j, when m is 1 or 2, R^11jrepresents a hydrogen atom; and when A^1jrepresents a methylimino group, A^2jand A^3jrepresent a methine group, R^1jrepresents a methyl group, R^2j, R^3j, R^4j, and R^5jrepresent a hydrogen atom, and n represents 0 or 1, both R^6jand R^7jare a chlorine atom and one of e and R⁷is a chlorine atom and the other is a hydrogen atom)

the Group X^jconsists of −OR^11jand a halogen atom; and

the Group Y^jconsists of a C1-C6 chain hydrocarbon group, a —OR^11j, and a halogen atom.

A compound of the formula (Z):

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wherein, R^1j, R^2j, R^3j, R^4j, R^5j, R^6j, A^1j, A^3j, and n are as defined in the formula (1-0);

A compound of the formula (Z) wherein A^1jis —NR^8j—, an oxygen atom, or a sulfur atom, and R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, and R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a cyclopropyl group, or a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms or a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C6 chain hydrocarbon group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C6 alkyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a C1-C3 alkyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methyl group, an ethyl group, a propyl group, an isopropyl group, a methoxymethyl group, an ethoxymethyl group, a cyclopropyl group, or a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis an ethyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a propyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis an isopropyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methyl group or a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and R^8jis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (Z) wherein A^1jis an oxygen atom;

A compound of the formula (Z) wherein A^1jis a sulfur atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, and R^8jis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, and R^8jis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (Z) wherein A^3jis a nitrogen atom or ═CR^10j—, and R^10jis a halogen atom or a hydrogen atom;

A compound of the formula (Z) wherein A^3jis ═CR^10j—, and R^10jis a halogen atom or a hydrogen atom;

A compound of the formula (Z) wherein A^3jis ═CR^10j—, and R^10jis a hydrogen atom;

A compound of the formula (Z) wherein A^3jis a nitrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and A^3jis ═CR^10j—;

A compound of the formula (Z) wherein A^1jis a sulfur atom, and A^3jis ═CR^10j—;

A compound of the formula (Z) wherein A^1jis —NR^8j—, and A^3jis a nitrogen atom;

A compound of the formula (Z) wherein A^1jis a sulfur atom, and A^3jis a nitrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, A^3jis a nitrogen atom or ═CR^10j—, and R^10jis a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, and A^3jis a nitrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, A^3jis ═CR^10j—, and R^10jis a hydrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a methyl group, and A^3jis a nitrogen atom;

A compound of the formula (Z) wherein A^1jis —NR^8j—, R^8jis a methyl group, and A^3jis a nitrogen atom;

A compound of the formula (Z) wherein R^1jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein R^1jis a C1-C6 chain hydrocarbon group optionally having one or more fluorine atoms;

A compound of the formula (Z) wherein R^1jis a C1-C6 chain hydrocarbon group;

A compound of the formula (Z) wherein R^1jis a C1-C6 alkyl group;

A compound of the formula (Z) wherein R^1jis a C1-C3 alkyl group;

A compound of the formula (Z) wherein R^1jis a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, a sec-butyl group, an isobutyl group, a tert-butyl group, a cyclopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group;

A compound of the formula (Z) wherein R^1jis a methyl group;

A compound of the formula (Z) wherein R^1jis an ethyl group;

A compound of the formula (Z) wherein R^1jis a propyl group;

A compound of the formula (Z) wherein R^1jis an isopropyl group;

A compound of the formula (Z) wherein R^1jis a trifluoromethyl group;

A compound of the formula (Z) wherein R^1jis a 2,2,2-trifluoroethyl group;

A compound of the formula (Z) wherein R^1jis a C3-C6 alicyclic hydrocarbon group optionally having one or more atoms or groups selected from Group Y^j;

A compound of the formula (Z) wherein R^1jis a C3-C6 alicyclic hydrocarbon group;

A compound of the formula (Z) wherein R^1jis a cyclopropyl group, a cyclobutyl group, or a cyclopentyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare same or different and are independently a fluorine atom, a chlorine atom, or a hydrogen atom, and R^3jis a fluorine atom, a chlorine atom, a bromine atom, a trifluoromethyl group, or a hydrogen atom;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, R^3jis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a C1-C6 alkyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a optionally having one or more fluorine atoms C1-C6 alkyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a C1-C3 alkyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a chlorine atom, a bromine atom, a trifluoromethyl group, or a hydrogen atom;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a fluorine atom;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a chlorine atom;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a bromine atom;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a methyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a trifluoromethyl group;

A compound of the formula (Z) wherein R^2j, R^4j, and R^5jare a hydrogen atom, and R^3jis a trifluoromethoxy group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R^5jare a hydrogen atom;

A compound of the formula (Z) wherein R^6jis a halogen atom;

A compound of the formula (Z) wherein R^6jis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (Z) wherein R^6jis a bromine atom;

A compound of the formula (Z) wherein R^6jis an iodine atom;

A compound of the formula (Z) wherein R^6jis a trifluoromethyl group;

A compound of the formula (Z) wherein R^6jis a pentafluoroethyl group;

A compound of the formula (Z) wherein R^6jis a heptafluoroisopropyl group;

A compound of the formula (Z) wherein R^6jis a trifluoromethoxy group;

A compound of the formula (Z) wherein R^6jis a trifluoromethylsulfanyl group;

A compound of the formula (Z) wherein R^6jis a trifluoromethylsulfinyl group;

A compound of the formula (Z) wherein R^6jis a trifluoromethylsulfonyl group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R^5jare same or different and are independently a fluorine atom, a chlorine atom, or a hydrogen atom, and R^6jis a trifluoromethyl group or a pentafluoroethyl group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R^5jare a hydrogen atom, and R^6jis a trifluoromethyl group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R^5jare a hydrogen atom, and R^6jis a pentafluoroethyl group or a heptafluoroisopropyl group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R⁵are a hydrogen atom, and R^6jis a trifluoromethoxy group;

A compound of the formula (Z) wherein R^2j, R^3j, R^4j, and R^5jare a hydrogen atom, and R^6jis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a C1-C6 alkyl group, A^3jis ═CR^10j—, R^10jis a hydrogen atom, R^1jis a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2j, R^4j, and R^5jare a hydrogen atom, R^3jis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, and R^6jis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom; and

A compound of the formula (Z) wherein A^1jis —NR^8j— or a sulfur atom, R^8jis a C1-C6 alkyl group, A^3jis a nitrogen atom, R^1jis a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2j, R^4j, and R^5jare a hydrogen atom, R^3jis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, and R^6jis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom.

The present compound can be produced, for example, by the following Production methods A-F.

(Production Method A)

The present compound (1) can be produced by reacting Compound (1F) with Compound (5). Alternatively, the present compound (1) can be produced by reacting Compound (F) with Compound (5) to give Compound (B), followed by cyclizing Compound (B):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and n are as defined above.

(Production Method B)

The present compound (1) can be produced by reacting Compound (1F) with Compound (M3). Alternatively, the present compound (1) can be produced by reacting Compound (F) with Compound (5) to give Compound (B), followed by cyclizing Compound (B):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³and n are as defined above.

(Production Method C)

The present compound (1) can be produced by reacting Compound (F) with Compound (3). Alternatively, the present compound (1) can be produced by reacting Compound (1F) with Compound (3) to give Compound (1J), followed by cyclizing Compound (1J):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and n are as defined above.

(Production Method D)

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting Compound (K) with a sulfating agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

(Production Method E)

Compound (23) of the formula (1) wherein n is 0 can be produced, for example, by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and n are as defined above, and V²represents a fluorine atom or a chlorine atom.

(Production Method F)

Compound (23) of the formula (1) wherein n is 0 can be produced, for example, by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, n, and V²are as defined above.

The production method of the present compound is illustrated below.

The production methods A-F of the present compound are further illustrated bellow. In addition, the production methods which the present compound is converted to other present compound are illustrated. The present compound can be produced, for example, by the following Production methods 1-26.

(Production Method 1) (Step (C-1))

Compound (4) of the formula (1) wherein A¹is —NR⁸— can be produced by reacting Compound (2) with Compound (3):

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wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a base, acid, sulfite, or disulfite.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; carbonates such as sodium carbonate and potassium carbonate; and mixtures thereof.

Examples of the acid to be used in the reaction include sulfonic acids such as p-toluenesulfonic acid; and carboxylic acids such as acetic acid.

Examples of the sulfite to be used in the reaction include sodium sulfite and potassium sulfite.

Examples of the disulfite to be used in the reaction include sodium disulfite and potassium disulfite.

Examples of the solvent to be used in the reaction include ethers such as tetrahydrofuran (hereinafter referred to as THF), ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as N,N-dimethylformamide (hereinafter referred to as DMF) and N-methylpyrrolidone (hereinafter referred to as NMP); sulfoxides such as dimethylsulfoxide (hereinafter referred to as DMSO); nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

An oxidizing agent can be added to the reaction as necessary.

Examples of the oxidizing agent to be used in the reaction include an oxygen, copper (II) oxide, and 2,3-dichloro-5,6-dicyano-p-benzoquinon.

The amount of Compound (3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the base to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the acid to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the sulfite to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the disulfite to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the oxidizing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (4) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (4) can be further purified by chromatography, recrystallization, and the like.

(Production Method 2) (Step A-1)

Compound (4) of the formula (1) wherein A¹is —NR⁸—can be produced by reacting Compound (2) with Compound (5) in the presence of a dehydration-condensing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, tert-butyl methyl ether, ethylene glycol dimethyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (hereinafter referred to as WSC), and 1,3-dicyclohexylcarbodiimide; and (benzotriazol-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate (hereinafter referred to as BOP reagent).

A catalyst can be added to the reaction as necessary.

Examples of the catalyst to be used in the reaction include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).

The amount of Compound (5) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the catalyst to be used in the reaction is usually 0.01 to 0.1 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

Alternatively, Compound (4) can be produced according to the above method using Compound (M3) instead of Compound (5).

When Compound (M3) is used, the reaction is usually performed without a dehydration-condensing agent.

A base can be added to the reaction as necessary.

Examples of the base to be used in the reaction include carbonates of alkali metal such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.

The amount of Compound (M3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (2).

(Production Method 3) (Step (A-3), Step (B-3))

Compound (4) of the formula (1) wherein A¹is —NR⁸— can be produced by dehydration-condensing Compound (6):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; alcohols such as methanol, ethanol, propanol, butanol, and pentanol; and mixtures thereof.

In the reaction, an acid or a dehydrating agent can be used as necessary. Examples of the acid to be used in the reaction include sulfonic acids such as p-toluenesulfonic acid, and carboxylic acids such as acetic acid. Examples of the dehydrating agent to be used in the reaction include phosphorous oxychloride, acetic anhydride, and trifluoroacetic anhydride.

The amount of the acid or the dehydrating agent to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (6).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (4) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (4) can be further purified by chromatography, recrystallization, and the like.

(Production Method 4) (Step (A-3), Step (B-3))

Compound (4) of the formula (1) wherein A¹is —NR⁸— can be produced by reacting Compound (6) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include tripotassium phosphate.

The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (6).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method 5)

Compound (4) of the formula (1) wherein A¹is —NR⁸— can be produced by reacting Compound (32) with Compound (33) in the presence of a base.

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above, and L represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom, a trifluoromethylsulfonyloxy group and a methylsulfonyloxy group.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include hydrides of alkali metal or alkali earth metal such as sodium hydride, potassium hydride, and calcium hydride; inorganic bases such as sodium carbonate and potassium carbonate; and organic bases such as triethylamine.

The amount of Compound (33) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (32).

The amount of the base to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (32).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method 6) (Step (A-1))

Compound (8) of the formula (1) wherein A¹is an oxygen atom can be produced by reacting Compound (7) with Compound (5) in the presence of an acid:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence or absence of a solvent.

Examples of the acid to be used in the reaction include polyphosphoric acid and trimethylsilyl polyphosphate.

When polyphosphoric acid is used as an acid, though the reaction is usually performed in the absence of a solvent, the reaction may be performed in the presence of a solvent.

The amount of Compound (5) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (7). The amount of the acid to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (7).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (8) can be isolated by post-treatments, for example, pouring the reaction mixture into water and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (8) can be further purified by chromatography, recrystallization, and the like.

Alternatively, Compound (8) can be produced according to the above method using Compound (M3) instead of Compound (5).

When Compound (M3) is used, the reaction is usually performed without a dehydration-condensing agent.

A base can be added to the reaction as necessary.

The amount of Compound (M3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (7). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (7).

(Production Method 7) (Step (C-3))

Compound (8) of the formula (1) wherein A¹is an oxygen atom can be produced by oxidizing Compound (9):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, and chlorobenzene; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; acetic acid; and mixtures thereof.

Examples of the oxidizing agent to be used in the reaction include a metal oxidizing agent such as lead (IV) acetate and lead (IV) oxide, and a hypervalent iodine compound such as iodobenzene diacetate.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (9).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (8) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (8) can be further purified by chromatography, recrystallization, and the like.

(Production Method 8) (Step (A-3), Step (B-3))

Compound (8) of the formula (1) wherein A¹is an oxygen atom can be produced by reacting Compound (10) in the presence of a dehydration-condensing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; and mixtures thereof. Among of them, carbon tetrachloride can be used as a dehydration-condensing agent.

Examples of the dehydration-condensing agent to be used in the reaction include a mixture of triphenylphosphine, a base and carbon tetrachloride or carbon tetrabromide, and a mixture of triphenylphosphine and azodiesters such as diethyl azodicarboxylate ester.

Examples of the base to be used in the reaction include tertiary amines such as triethylamine and diisopropylethylamine.

The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (10). The amount of the base to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (10).

The reaction temperature of the reaction is usually within a range of −30 to 100° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

(Production Method 9) (Step (A-3), Step (B-3))

Compound (8) of the formula (1) wherein A¹is an oxygen atom can be produced by reacting Compound (10) in the presence of an acid:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the acid include sulfonic acids such as p-toluenesulfonic acid and polyphosphoric acid.

The amount of the acid to be used in the reaction is usually 0.1 to 3 moles based on 1 mole of Compound (10).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 1 to 24 hours.

Compound (8) can be further purified by chromatography, recrystallization, and the like.

(Production Method 10) (Step (C-1))

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting Compound (11) with Compound (3):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a base, acid, sulfite, or disulfite.

Examples of the acid to be used in the reaction include sulfonic acids such as p-toluenesulfonic acid; and carboxylic acids such as acetic acid.

Examples of the sulfite to be used in the reaction include sodium sulfite and potassium sulfite.

Examples of the disulfite to be used in the reaction include sodium disulfite and potassium disulfite.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate nitriles such as acetonitrile; acid amides such as DMF, and NMP; sulfoxides such as DMSO; aromatic hydrocarbons such as toluene, xylene, nitrobenzene; and mixtures thereof.

An oxidizing agent can be added to the reaction as necessary.

Examples of the oxidizing agent to be used in the reaction include an oxygen, copper (II) oxide, and 2,3-dichloro-5,6-dicyano-p-benzoquinon.

The amount of Compound (3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (11). The amount of the acid to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (11). The amount of the sulfite to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (11). The amount of the disulfite to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (11). The amount of the oxidizing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (11). The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (12) can be isolated by post-treatments, for example, adding the reaction mixture to water and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (12) can be further purified by chromatography, recrystallization, and the like.

(Production Method 11) (Step (C-1))

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting hydrochloride of Compound (11) with Compound (3):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is performed in the presence of a base and usually in the presence of a solvent.

Examples of the base to be used in the reaction include tertiary amines such as diisopropylethylamine and triethylamine.

Examples of the solvent to be used in the reaction include sulfoxides such as DMSO; aromatic hydrocarbons such as nitrobenzene; and mixtures thereof.

The amount of Compound (3) to be used in the reaction is usually 0.5 to 3 moles based on 1 mole of Compound (11). The amount of the base to be used in the reaction is usually 1 to 2 moles based on 1 mole of Compound (11).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method 12)

Compound (14) of the formula (1) wherein R⁶is a cyano group or a C1-C6 alkyl group can be produced by reacting Compound (13) with a cyanating agent or di(C1-C6 alkyl) zinc in the presence of a palladium compound:

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wherein, R¹, R², R³, R⁴, R⁵, R⁷, A¹, A², and A³are as defined above, V¹represents a leaving group such as a bromine atom and an iodine atom, and R^6zrepresents a cyano group or a C1-C6 alkyl group.

The reaction is usually performed in the presence of a solvent.

Examples of the cyanating agent to be used in the reaction include zinc cyanide. Examples of di(C1-C6 alkyl)zinc to be used in the reaction include dimethyl zinc, diethyl zinc, and diisopropyl zinc.

Examples of the palladium compound to be used in the reaction include tetrakis(triphenylphosphine)palladium.

The amount of the cyanating agent or di(C1-C6 alkyl) zinc to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (13). The amount of the palladium compound to be used in the reaction is usually 0.01 to 0.5 moles based on 1 mole of Compound (13).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (14) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (14) can be further purified by chromatography, recrystallization, and the like.

(Production Method 13)

Compound (16) of the formula (1) wherein R⁶is C(O)R^6ycan be produced by reacting Compound (15) with a organometallic agent, then a carbonylating agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁷, A¹, A², and A³are as defined above, R^6yis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a hydrogen atom, or —OR¹¹, and R¹¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane.

Examples of the organometallic agent to be used in the reaction include alkyllithiums such as n-butyllithium and tert-butyllithium, organic magnesium halides such as isopropylmagnesium chloride.

Examples of the carbonylating agent to be used in the reaction include DMF, 1-formylpiperidine, 4-formylmorpholine, ethyl formate, ethyl acetate, methyl trifluoroacetate, methyl chloroformate, ethyl chloroformate, and carbon dioxide.

The amount of the organometallic agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (15). The amount of the carbonylating agent to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (15).

The reaction temperature of the reaction is usually within a range of −100 to 0° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (16) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (16) can be further purified by chromatography, recrystallization, and the like.

(Production Method 14)

Compound (18) of the formula (1) wherein R⁶is a C1-C3 perfluoroalkyl group can be produced by reacting Compound (13) with Compound (17) in the presence of copper iodide:

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wherein, R¹, R², R³, R⁴, R⁵, R⁷, A¹, A², A³, and V¹are as defined above, and R^frepresents a C1-C3 perfluoroalkyl group.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; acid amides such as DMF and NMP; and mixtures thereof.

The amount of Compound (17) to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (13). The amount of copper iodide to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (13).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (18) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (18) can be further purified by chromatography, recrystallization, and the like.

(Production Method 15)

Compound (20) of the formula (1) wherein R⁶is a phenyl group optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms can be produced by reacting Compound (13) with boronic acid compound (19) in the presence of a palladium compound:

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wherein, R¹, R², R³, R⁴, R⁵, R⁷, A¹, A², A³, and V¹are as defined above, and R^Arrepresents a phenyl group optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms.

The reaction is usually performed in the presence of a solvent.

The reaction can be performed in the presence of a base and/or a phase transfer catalyst as necessary.

Examples of the base to be used in the reaction include inorganic salts such as sodium acetate, potassium acetate, potassium carbonate, tripotassium phosphate, and sodium hydrogen carbonate.

Examples of the phase transfer catalyst to be used in the reaction include quaternary ammonium salts such as tetrabutylammonium bromide and benzyltriethylammonium bromide.

The reaction can be performed in the presence of a ligand as necessary.

Examples of the ligand to be used in the reaction include 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; alcohols such as methanol and ethanol; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; acid amides such as DMF and NMP; water; and mixtures thereof.

Examples of the palladium compound to be used in the reaction include palladium acetate, tetrakistriphenylphosphine palladium, {1,1′-bis(diphenylphosphino)ferrocene}dichloropalladium-methylene chloride complex, and bis(triphenylphosphine)palladium dichloride, and tris(dibenzylideneacetone)dipalladium (0).

The amount of boronic acid compound (19) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (13). The amount of the palladium compound to be used in the reaction is usually 0.01 to 0.5 moles based on 1 mole of Compound (13).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (20) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (20) can be further purified by chromatography, recrystallization, and the like.

(Production Method 16) (Step (E-4))

Compound (23) of the formula (1) wherein n is 0 can be produced by reacting Compound (21) with Compound (22) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include water; ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; alcohols such as methanol and ethanol; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; and mixtures thereof.

Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride.

The amount of Compound (22) to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (21). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (21).

The reaction temperature of the reaction is usually within a range of 0 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (23) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (23) can be further purified by chromatography, recrystallization, and the like.

(Production Method 17) (Step (F-2))

Compound (23) of the formula (1) wherein n is 0 can be produced by reacting Compound (24) with Compound (25) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and L are as defined above.

The reaction is usually performed in the presence of a solvent.

The amount of the base to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (24). The amount of Compound (25) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (24).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method 18)

Compound (26) of the formula (1) wherein n is 1 can be produced by oxidizing Compound (23):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², and A³are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform; alcohols such as methanol and ethanol; acetic acid; water; and mixtures thereof.

Examples of the oxidizing agent to be used in the reaction include sodium periodate or m-chloroperbenzoic acid.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (23). Preferably, the amount of the oxidizing agent to be used in the reaction is 1 to 1.2 moles based on 1 mole of Compound (23).

The reaction temperature of the reaction is usually within a range of −20 to 80° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

After the completion of the reaction, Compound (26) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite, thiosodium sulfate) and an aqueous solution of a base (e.g. sodium hydrogen carbonate) as necessary, followed by drying and concentrating the organic layer. The isolated Compound (26) can be further purified by chromatography, recrystallization, and the like.

(Production Method 19)

Compound (27) of the formula (1) wherein n is 2 can be produced by reacting Compound (23) in the presence of an oxidizing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², and A³are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the oxidizing agent to be used in the reaction include m-chloroperbenzoic acid or an aqueous solution of hydrogen peroxide.

The amount of the oxidizing agent to be used in the reaction is usually 2 to 5 moles based on 1 mole of Compound (23). Preferably, the amount of the oxidizing agent to be used in the reaction is 2 to 3 moles based on 1 mole of Compound (23).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

After the completion of the reaction, Compound (27) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite, thiosodium sulfate) and an aqueous solution of a base (e.g. sodium hydrogen carbonate) as necessary, followed by drying and concentrating the organic layer. The isolated Compound (27) can be further purified by chromatography, recrystallization, and the like.

(Production Method 20)

Compound (27) of the formula (1) wherein n is 2 can be produced by reacting Compound (26) in the presence of an oxidizing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², and A³are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the oxidizing agent to be used in the reaction include m-chloroperbenzoic acid or an aqueous solution of hydrogen peroxide.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 4 moles based on 1 mole of Compound (26). Preferably, the amount of the oxidizing agent to be used in the reaction is 1 to 2 moles based on 1 mole of Compound (26).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

(Production Method 21) (Step (A-3), Step (B-3))

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting Compound (35) in the presence of an acid:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the acid include sulfonic acids such as p-toluenesulfonic acid, and polyphosphoric acid.

The amount of the acid to be used in the reaction is usually 0.1 to 3 moles based on 1 mole of Compound (35).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 1 to 24 hours.

After the completion of the reaction, Compound (12) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (12) can be further purified by chromatography, recrystallization, and the like.

(Production Method 22)

Compound (34-a) of the formula (1) wherein R⁶is SH, Compound (34-b) which is a disulfide form of Compound (34-a), Compound (36) of the formula (1) wherein R⁶is SR^6x, and Compound (37) of the formula (1) wherein R⁶is S(O)mR^6xcan be produced, for example, by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, R¹⁰, R⁷, A¹, A², A³, n, m, V¹and L are as defined above.

Step (22-1)

Compound (34-a) and/or Compound (34-b) can be produced by reacting Compound (13) with a thiolating agent in the presence of a catalyst.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include aromatic hydrocarbons such as toluene and xylene; acid amides such as DMF and NMP; sulfoxides such as DMSO; and mixtures thereof.

Examples of the thiolating agent to be used in the reaction include sodium sulfide, sodium sulfide nonahydrate, and thiourea.

Examples of the catalyst to be used in the reaction include copper (I) chloride, copper (I) bromide, and copper (I) iodide.

The reaction can be performed in the presence of a base as necessary.

Examples of the base to be used in the reaction include potassium carbonate, cesium carbonate, tripotassium phosphate, and triethylamine.

The amount of the thiolating agent to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (13). The amount of the catalyst to be used in the reaction is usually 0.1 to 5 moles based on 1 mole of Compound (13).

The reaction temperature of the reaction is usually within a range of 50 to 200° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (34-a) and/or Compound (34-b) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (34-a) and/or Compound (34-b) can be further purified by chromatography, recrystallization, and the like.

Step (22-2)

Compound (36) can be produced by reacting Compound (34-a) and/or Compound (34-b) with Compound (38-1) in the presence of a base.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, THF, and tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, 1,3-dimethyl-2-imidazolidinone, and dimethylsulfoxide; nitrogen-containing aromatic compounds such as pyridine and quinoline; water; and mixtures thereof.

Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, DBU, and 1,5-diazabicyclo[4.3.0]-5-nonen; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as tripotassium phosphate, potassium carbonate, sodium hydride, sodium hydroxide, and potassium hydroxide.

The amount of Compound (38-1) to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (34-a) and/or Compound (34-b). The amount of the base to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (34-a) and/or Compound (34-b).

The reaction temperature of the reaction is usually within a range of 0 to 120° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (36) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (36) can be further purified by chromatography, recrystallization, and the like.

Step (22-3)

Compound (37) wherein m is 1 or 2 can be produced by oxidizing Compound (36).

The reaction is usually performed in the presence of a solvent.

Examples of the oxidizing agent to be used in the reaction include m-chloroperbenzoic acid and an aqueous solution of hydrogen peroxide.

The reaction can be performed in the presence of a catalyst as necessary,

Examples of the catalyst to be used in the reaction include sodium tungstate.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (36).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

After the completion of the reaction, Compound (37) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite, thiosodium sulfate) and an aqueous solution of a base (e.g. sodium hydrogen carbonate) as necessary, followed by drying and concentrating the organic layer. The isolated Compound (37) can be further purified by chromatography, recrystallization, and the like.

(Production Method 23)

Compound (39) of the formula (1) wherein R⁶is NH₂, Compound (40) of the formula (1) wherein R⁵is NHR¹⁰, and Compound (41) of the formula (1) wherein R⁵is NR¹⁰R¹¹can be produced, for example, by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, R¹⁰, R¹¹, R⁷, A¹, A², A³, n, V¹, and L are as defined above.

Step (23-1)

Compound (39) can be produced by aminating Compound (13).

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include water; alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such as ethyl acetate and butyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and dimethylsulfoxide; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the aminating agent to be used in the reaction include ammonia, ammonia water, and lithium amide.

Examples of the copper compound to be used in the reaction include copper, copper (I) iodide, copper (I) oxide, copper (II) oxide, copper (II) acetylacetone, copper (II) acetate, and copper (II) sulfate.

A ligand can be added to the reaction as necessary.

Examples of the ligand to be used in the reaction include acetylacetone, salen, and phenanthroline.

A base can be added to the reaction as necessary.

The amount of the aminating agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (13). The amount of the copper compound to be used in the reaction is usually 0.02 to 0.5 moles based on 1 mole of Compound (13). The amount of the ligand to be used in the reaction is 0.02 to 2 moles based on 1 mole of Compound (13) as necessary. The amount of the base to be used in the reaction is 1 to 5 moles based on 1 mole of Compound (13) as necessary.

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (39) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (39) can be further purified by recrystallization, chromatography, and the like.

Step (23-2)

Compound (40) can be produced by reacting Compound (39) with Compound (38-1) in the presence of a base.

The amount of Compound (38-1) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (40). The amount of the base to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (40).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (40) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (40) can be further purified by recrystallization, chromatography, and the like.

Step (23-3)

Compound (41) can be produced by reacting Compound (40) with Compound (38-2) in the presence of a base.

The amount of Compound (38-2) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (40). The amount of the base to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (40).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (41) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (41) can be further purified by recrystallization, chromatography, and the like.

(Production Method 24)

Compound (43) of the formula (1) wherein R⁶is OR¹¹can be produced, for example, by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, R⁷, R¹¹, A¹, A², A³, V¹, and n are as defined above.

Examples of the base to be used in the reaction include hydrides of alkali metal or alkali earth metal such as sodium hydride, potassium hydride, and calcium hydride; inorganic bases such as sodium carbonate, potassium carbonate, and cesium carbonate; and organic bases such as triethylamine.

A copper compound can be added to the reaction as necessary.

Examples of the copper compound to be used in the reaction include copper, copper (I) iodide, copper (I) bromide, and copper (I) chloride.

The amount of Compound (42) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (13). The amount of the base to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (13).

The reaction temperature of the reaction is usually within a range of 20 to 250° C. The reaction time of the reaction is usually within a range of 0.1 to 48 hours.

After the completion of the reaction, Compound (43) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (43) can be further purified by recrystallization, chromatography, and the like.

(Production Method 25) (Step (A-1))

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting Compound (11) with Compound (5):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

Compound (12) can be produced according to the method described in Production method 2 using Compound (11) instead of Compound (2).

(Production Method 26) (Production Method D)

Compound (12) of the formula (1) wherein A¹is a sulfur atom can be produced by reacting Compound (1K) with a sulfating agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is performed in the presence or absence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as 1,4-dioxane, diethyl ether, tetrahydrofuran, tert-butyl methyl ether, and Diglyme; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane, and chlorobenzene; hydrocarbons such as toluene, benzene, and xylene; nitrile such as acetonitrile; pyridines such as pyridine, picoline, and lutidine; and mixtures thereof.

Examples of the sulfating agent to be used in the reaction include phosphorus pentasulfide and Lawesson's reagent (2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane 2,4-disulfide).

The amount of the sulfating agent to be used in the reaction is usually one or more moles based on 1 mole of Compound (1K).

The reaction temperature of the reaction is usually within a range of 0 to 200° C. The reaction time of the reaction is usually within a range of 1 to 24 hours.

After the completion of the reaction, Compound (12) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (12) can be further purified by recrystallization, chromatography, and the like.

The intermediates of the present invention can be produced, for example, by the following method. (Production method of intermediate 1)

Compound (2) can be produced by the following method:

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wherein, R⁶, R⁷, R⁸, A², and A³are as defined above.

(Step 1)

Compound (M2) can be produced by reacting Compound (M1) in the presence of a nitrating agent.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include halogenated hydrocarbons such as dichloromethane and chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water and mixtures thereof.

Examples of the nitrating agent to be used in the reaction include concentrated nitric acid.

The amount of the nitrating agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M1).

The reaction temperature of the reaction is usually within a range of −10 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M2) can be isolated by post-treatments, for example, pouring the reaction mixture into water and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M2) can be further purified by chromatography, recrystallization, and the like.

(Step 2)

Compound (2) can be produced by reacting Compound (M2) with hydrogen in the presence of a hydrogenating catalyst.

The reaction is usually performed under 1 to 100 atms of hydrogen in the presence of a catalyst.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; esters such as ethyl acetate and butyl acetate; alcohols such as methanol and ethanol; water; and mixtures thereof.

Examples of the hydrogenating catalyst to be used in the reaction include transition metal compounds such as palladium-carbon, palladium hydroxide, Raney® nickel, and platinum oxide.

The amount of hydrogen to be used in the reaction is usually 3 moles based on 1 mole of Compound (M1). The amount of the hydrogenating catalyst to be used in the reaction is usually 0.001 to 0.5 moles based on 1 mole of Compound (M1).

An acid (or base, and the like) can be added to the reaction as necessary.

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (2) can be isolated by post-treatments, for example, filtrating the reaction mixture and then extracting the mixture with an organic solvent as necessary, followed by drying and concentrating the organic layer. The isolated Compound (2) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 2) (Step (A-2))

Compound (6) can be produced by reacting Compound (2) with Compound (5) in the presence of a dehydration-condensing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

The reaction temperature of the reaction is usually within a range of 0 to 140° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (6) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (6) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 3) (Step (B-2))

Compound (6) can be produced by reacting Compound (2) with Compound (M3) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the base include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 4)

Compound (7) can be produced by the following method:

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wherein, R⁶, R⁷, A², and A³are as defined above.

(Step 1)

Compound (M5) can be produced by reacting Compound (M4) in the presence of a nitrating agent.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include halogenated hydrocarbons such as chloroform, acetic acid, concentrated sulfuric acid, concentrated nitric acid, water, and mixtures thereof.

Examples of the nitrating agent to be used in the reaction include concentrated nitric acid.

The amount of the nitrating agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M4).

The reaction temperature of the reaction is usually within a range of −10 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M5) can be isolated by post-treatments, for example, pouring the reaction mixture into water and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M5) can be further purified by chromatography, recrystallization, and the like.

(Step 2)

Compound (7) can be produced by reacting Compound (M5) with hydrogen in the presence of a hydrogenating catalyst.

The reaction is usually performed under 1 to 100 atms of hydrogen in the presence of a catalyst.

Examples of the hydrogenating catalyst to be used in the reaction include transition metal compounds such as palladium-carbon, palladium hydroxide, Raney® nickel, and platinum oxide.

The amount of hydrogen to be used in the reaction is usually 3 moles based on 1 mole of Compound (M5). The amount of the hydrogenating catalyst to be used in the reaction is usually 0.001 to 0.5 moles based on 1 mole of Compound (M5).

An acid (or base, and the like) can be added to the reaction as necessary.

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (7) can be isolated by post-treatments, for example, filtrating the reaction mixture and then extracting the mixture with an organic solvent as necessary, followed by drying and concentrating the organic layer. The isolated Compound (7) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 5) (Step (C-2))

Compound (9) can be produced by reacting Compound (7) with Compound (3):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aromatic hydrocarbons such as toluene and xylene; and mixtures thereof.

The amount of Compound (3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (7).

An acid or base can be added to the reaction as necessary.

The reaction temperature of the reaction is usually within a range of 0 to 150° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (9) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (9) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 6) (Step (A-2))

Compound (10) can be produced by reacting Compound (7) with Compound (5) in the presence of a dehydration-condensing agent:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

The amount of Compound (5) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (7). The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (7).

The reaction temperature of the reaction is usually within a range of 0 to 140° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (10) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (10) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 7) (Step (B-2))

Compound (10) cab be produced by reacting Compound (7) with Compound (M3) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include alkali metal carbonates such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 8)

Compound (11) can be produced by the following method:

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wherein, R⁶, R⁷, A², and A³are as defined above.

(Step 1)

Compound (M7) can be produced by reacting Compound (M6) with thiourea in the presence of a base.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include alcohols such as methanol and ethanol; water; and mixtures thereof.

Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.

The amount of thiourea to be used in the reaction is usually 0.5 to 3 moles based on 1 mole of Compound (M6). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M6).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M7) can be isolated by post-treatments, for example, pouring an acid into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M7) can be further purified by chromatography, recrystallization, and the like.

(Step 2)

Compound (11) can be produced by reducing Compound (M7).

The reduction reaction can be performed, for example, in the presence of a reducing agent such as iron powder and zinc powder; acids such as hydrochloric acid and acetic acid; and water.

The reaction can be usually performed in the presence of a solvent.

The amount of the reducing agent to be used in the reaction is usually 3 to 10 moles based on 1 mole of Compound (M7).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (11) can be isolated by post-treatments, for example, adding water to the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (11) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 9)

Compound (28) of Compound (21) wherein A¹is —NR⁸— can be produced by reacting Compound (2) with Compound (M8) in the presence of a base:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

The amount of Compound (M8) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the base to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (28) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (28) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 10) (Step (E-1))

Compound (28) of Compound (21) wherein A¹is —NR⁸— can be produced by reacting Compound (2) with Compound (M9) in the presence of a dehydration-condensing agent:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

A catalyst can be added to the reaction as necessary.

Examples of the catalyst to be used in the reaction include 1-hydroxybenzotriazole (hereinafter referred to as HOBt).

The amount of Compound (M9) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (2). The amount of the catalyst to be used in the reaction is usually 0.01 to 0.1 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 11) (Step (E-3))

Compound (28) of Compound (21) wherein A¹is —NR⁸— can be produced by dehydration-condensing Compound (M10):

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

The amount of the acid or dehydrating agent to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M10).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (28) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (28) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 12) (Step (E-3))

Compound (28) of Compound (21) wherein A¹is —NR⁸— can be produced by reacting Compound (M10) in the presence of a base:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include tripotassium phosphate.

The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M10).

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 13) (Step (E-2))

Compound (M10) can be produced by reacting Compound (2) with Compound (M9) in the presence of a dehydration-condensing agent:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

The reaction temperature of the reaction is usually within a range of 0 to 140° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M10) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M10) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 14)

Compound (M10) can be produced by reacting Compound (2) with Compound (M12) in the presence of a base:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A², A³, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

The amount of Compound (M12) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (2). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (2).

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 15)

Compound (29) of Compound (3) wherein n is 0 can be produced by the following method:

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wherein, R¹, R², R³, R⁴, R⁵, and V²are as defined above.

(Step I15-1)

Compound (M14) can be produced by reacting Compound (M13) with Compound (22) in the presence of a base.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride.

The amount of Compound (22) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M13). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M13).

The reaction temperature of the reaction is usually within a range of 0 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (M14) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M14) can be further purified by chromatography, recrystallization, and the like.

(Step I15-2)

Compound (29) can be produced by reducing Compound (M14).

The reaction is usually performed in the presence of a solvent.

Examples of the reducing agent to be used in the reaction include diisobutylaluminium hydrate.

The amount of the reducing agent to be used in the reaction is usually 1 to 2 moles based on 1 mole of Compound (M14).

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

After the completion of the reaction, Compound (29) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (29) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 16)

Compound (29) of Compound (3) wherein n is 0 can be produced by reacting Compound (M8) with Compound (22) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, and V²are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include alkali metal hydrides such as sodium hydride.

The amount of Compound (22) to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M15). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M8).

The reaction temperature of the reaction is usually within a range of 0 to 150° C. The reaction time of the reaction is usually within a range of 0.5 to 24 hours.

(Production Method of Intermediate 17)

Compound (30) of Compound (5) wherein n is 0 can be produced by hydrolyzing Compound (M14) in the presence of a base, and Compound (M23) of Compound (5) wherein n is 1 or 2 can be produced by the following method:

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wherein, R¹, R², R³, R⁴, and R⁵are as defined above, and r represents 1 or 2.

(Step I17-1)

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.

The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M14).

The reaction temperature of the reaction is usually within a range of 0 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (30) can be isolated by post-treatments, for example, acidifying the reaction mixture and than extracting with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (30) can be further purified by chromatography, recrystallization, and the like.

(Step I17-2)

The reaction is usually performed in the presence of a solvent.

Examples of the oxidizing agent to be used in the reaction include m-chloroperbenzoic acid and an aqueous solution of hydrogen peroxide.

The reaction can be performed in the presence of a catalyst as necessary.

Examples of the catalyst to be used in the reaction include sodium tungstate.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (M14).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

After the completion of the reaction, Compound (M22) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite, thiosodium sulfate) and an aqueous solution of a base (e.g. sodium hydrogen carbonate) as necessary, followed by drying and concentrating the organic layer. The isolated Compound (M22) can be further purified by chromatography, recrystallization, and the like.

(Step I17-3)

The reaction is usually performed in the presence of a solvent.

Examples of the base to be used in the reaction include alkali metal hydroxides such as sodium hydroxide and potassium hydroxide.

The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M22).

The reaction temperature of the reaction is usually within a range of 0 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M23) can be isolated by post-treatments, for example, acidifying the reaction mixture and than extracting with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M23) can be further purified by chromatography, recrystallization, and the like.

(Step I17-4)

The reaction is usually performed in the presence of a solvent.

Examples of the oxidizing agent to be used in the reaction include m-chloroperbenzoic acid and an aqueous solution of hydrogen peroxide.

The reaction can be performed in the presence of a catalyst as necessary.

Examples of the catalyst to be used in the reaction include sodium tungstate.

The amount of the oxidizing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (30).

The reaction temperature of the reaction is usually within a range of −20 to 120° C. The reaction time of the reaction is usually within a range of 0.1 to 12 hours.

After the completion of the reaction, Compound (M23) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by washing the organic layer with an aqueous solution of a reducing agent (e.g. sodium sulfite, thiosodium sulfate) and an aqueous solution of a base (e.g. sodium hydrogen carbonate) as necessary, followed by drying and concentrating the organic layer. The isolated Compound (M23) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 18)

Compound (30) of Compound (5) wherein n is 0 can be produced by hydrolyzing Compound (M14) in the presence of an acid:

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wherein, R¹, R², R³, R⁴, and R⁵are as defined above.

In the reaction, usually, an aqueous solution of the acid is used as a solvent.

Examples of the acid to be used in the reaction include mineral acids such as hydrochloric acid, nitric acid, phosphoric acid, and sulfuric acid, and carboxylic acids such as acetic acid and trifluoroacetic acid.

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (30) can be isolated by post-treatments, for example, extracting the reaction mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (30) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 19)

Compound (M3) can be produced by chlorinating Compound (5) in the presence of a chlorinating agent:

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wherein, R¹, R², R³, R⁴, R⁵, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the chlorinating agent to be used in the reaction include thionyl chloride and oxalyl dichloride.

The amount of the chlorinating agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (5).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M3) can be isolated by evaporating the solvent.

(Production Method of Intermediate 20)

Compound (M21) of Compound (2) wherein A³is a nitrogen atom can be produced, for example, by the following method:

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wherein, R⁶, R⁷, R⁸, and A²are as defined above, and X^grepresents a chlorine atom, a bromine atom, or an iodine atom.

(Step I20-1)

Compound (M19) can be produced by reacting Compound (M17) with Compound (M18).

The reaction is performed in the presence or absence of a solvent.

Examples of the solvent to be used in the reaction include water, alcohols such as methanol and ethanol; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such as ethyl acetate and butyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile; aprotic polar solvents such as DMF, NMP, and dimethylsulfoxide; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

A base can be added to the reaction as necessary.

Examples of the base to be used in the reaction include nitrogen-containing heterocyclic compounds such as pyridine, picoline, 2,6-lutidine, diazabicycloundecene (hereinafter referred to as DBU), and 1,5-diazabicyclo[4.3.0]-5-nonen; tertiary amines such as triethylamine and N-ethyldiisopropylamine; and inorganic bases such as potassium carbonate, cesium carbonate, and sodium hydroxide.

The amount of Compound (M18) to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (M17).

The reaction temperature of the reaction is usually within a range of 0 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M19) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (M19) can be further purified by recrystallization, chromatography, and the like.

(Step I20-2)

Compound (M20) can be produced by reacting Compound (M19) with a halogenating agent.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include water; acetic acid; ethers such as 1,4-dioxane, diethyl ether, and THF; esters such as ethyl acetate and butyl acetate; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, and 1,2-dichloroethane; nitriles such as acetonitrile; aprotic polar solvents such as DMF and NMP; and mixtures thereof.

Examples of the halogenating agent to be used in the reaction include a chlorinating agent such as N-chlorosuccinimide and chlorine; a brominating agent such as N-bromosuccinimide and bromine; and an iodinating agent such as N-iodosuccinimide and iodine.

The amount of the halogenating agent to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M19).

The reaction temperature of the reaction is usually within a range of −10 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M20) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (M20) can be further purified by recrystallization, chromatography, and the like.

(Step I20-3)

Compound (M21) can be produced by reacting Compound (M20) with an aminating agent in the presence of a copper compound.

The reaction is usually performed in the presence of a solvent.

Examples of the aminating agent to be used in the reaction include ammonia, ammonia water, and lithium amide.

A ligand can be added to the reaction as necessary.

Examples of the ligand to be used in the reaction include acetylacetone, salen, and phenanthroline.

A base can be added to the reaction as necessary.

The amount of the aminating agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (M20). The amount of the copper compound to be used in the reaction is usually 0.02 to 0.5 moles based on 1 mole of Compound (M20). The amount of the ligand to be used in the reaction is 0.02 to 2 moles based on 1 mole of Compound (M20) as necessary. The amount of the base to be used in the reaction is 1 to 5 moles based on 1 mole of Compound (M20) as necessary.

The reaction temperature of the reaction is usually within a range of 30 to 200° C. The reaction time of the reaction is usually within a range of 0.1 to 48 hours.

After the completion of the reaction, Compound (M21) can be isolated by pouring the reaction mixture into water, extracting with an organic solvent, and concentrating the organic layer; pouring the reaction mixture into water, and collecting the generated solids by filtration; or collecting the solids generated in the reaction mixture by filtration. The isolated Compound (M21) can be further purified by recrystallization, chromatography, and the like.

(Production Method of Intermediate 21) (Step (A-2))

Compound (35) can be produced by reacting Compound (11) with Compound (5) in the presence of a dehydration-condensing agent:

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wherein, R¹, R², R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

The amount of Compound (5) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (11). The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (11).

The reaction temperature of the reaction is usually within a range of 0 to 140° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (35) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (35) can be further purified by chromatography, recrystallization, and the like.

(Production Method of Intermediate 22) (Step (B-2))

Compound (35) can be produced by reacting Compound (11) with Compound (M3) in the presence of a base:

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

The reaction is usually performed in the presence of a solvent.

The amount of Compound (M3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (11). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (11).

The reaction temperature of the reaction is usually within a range of −20 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

(Production Method of Intermediate 23) (Step (E-1))

Compound (M24) of Compound (21) wherein A¹is an oxygen atom can be produced by reacting Compound (7) with Compound (M9):

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, n, and V²are as defined above.

Compound (M24) can be produced according to the method described in (Production method 6) using Compound (M9) instead of Compound (5).

(Production Method of Intermediate 24) (Step (E-2))

Compound (M25) of Compound (1E) wherein A¹is an oxygen atom can be produced by reacting Compound (7) with Compound (M9). Additionally, Compound (M26) of Compound (1E) wherein A¹is a sulfur atom can be produced by reacting Compound (11) with Compound (M9):

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, n, and V²are as defined above.

Compound (M25) can be produced according to the method described in Production method of intermediate 6 using Compound (M9) instead of Compound (5).

Compound (M26) can be produced according to the method described in Production method of intermediate 21 using Compound (11) instead of Compound (5).

(Production Method of Intermediate 25) (Step (E-3))

Compound (M27) of Compound (21) wherein A¹is an oxygen atom can be produced by cyclizing Compound (M25). Additionally, Compound (M28) of Compound (21) wherein A¹is a sulfur atom can be produced by cyclizing Compound (M26):

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, n, and V²are as defined above.

Compound (M27) can be produced according to the method described in Production method 8 or Production method 9 using Compound (M25) instead of Compound (10).

Compound (M28) can be produced according to the method described in Production method 21 using Compound (M26) instead of Compound (35).

(Production Method of Intermediate 26) (Step (F-1))

Compound (24) can be produced by reacting Compound (21) with sodium sulfide, sodium hydrogen sulfide, or hydrogen sulfide:

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wherein, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, n, and V²are as defined above.

Compound (24) can be produced according to the method described in Production method 16 using sodium sulfide, sodium hydrogen sulfide, or hydrogen sulfide instead of Compound (22).

When sodium sulfide or sodium hydrogen sulfide is used, a reaction is usually performed without a base.

(Production Method of Intermediate 27) (Production Method D)

Compound (1K) can be produced by reacting Compound (M30) with Compound (5):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above.

(Step I27-1)

Compound (M30) can be produced by reducing Compound (M29).

The reduction reaction can be performed in the presence of a reducing agent such as iron powder and zinc powder; acids such as hydrochloric acid and acetic acid; and water.

The reaction can be usually performed in the presence of a solvent.

The amount of the reducing agent to be used in the reaction is usually 3 to 10 moles based on 1 mole of Compound (M29).

The reaction temperature of the reaction is usually within a range of 0 to 100° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (M30) can be isolated by post-treatments, for example, adding water to the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (M30) can be further purified by chromatography, recrystallization, and the like.

(Step I27-2)

The reaction is usually performed in the presence or absence of a solvent.

Examples of the solvent to be used in the reaction include ethers such as THF, ethylene glycol dimethyl ether, tert-butyl methyl ether, and 1,4-dioxane; aliphatic hydrocarbons such as hexane, heptane, and octane; aromatic hydrocarbons such as toluene and xylene; halogenated hydrocarbons such as chlorobenzene; esters such as ethyl acetate and butyl acetate; nitriles such as acetonitrile; acid amides such as DMF and NMP; sulfoxides such as DMSO; nitrogen-containing aromatic compounds such as pyridine and quinoline; and mixtures thereof.

Examples of the dehydration-condensing agent to be used in the reaction include carbodiimides such as WSC and 1,3-dicyclohexylcarbodiimide, and BOP reagent.

The amount of Compound (5) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M30). The amount of the dehydration-condensing agent to be used in the reaction is usually 1 to 5 moles based on 1 mole of Compound (M30).

The reaction temperature of the reaction is usually within a range of 0 to 140° C. The reaction time of the reaction is usually within a range of 0.1 to 24 hours.

After the completion of the reaction, Compound (1K) can be isolated by post-treatments, for example, pouring water into the reaction mixture and then extracting the mixture with an organic solvent, followed by drying and concentrating the organic layer. The isolated Compound (1K) can be further purified by chromatography, recrystallization, and the like.

Alternatively, Compound (1K) can be produced according to the above method using Compound (M3) instead of Compound (5).

When Compound (M3) is used, the reaction is usually performed without a dehydration-condensing agent

A base can be added to the reaction as necessary.

Examples of the base include carbonates of alkali metal such as sodium carbonate and potassium carbonate; tertiary amines such as triethylamine and diisopropylethylamine; and nitrogen-containing aromatic compounds such as pyridine and 4-dimethylaminopyridine.

The amount of Compound (M3) to be used in the reaction is usually 1 to 3 moles based on 1 mole of Compound (M30). The amount of the base to be used in the reaction is usually 1 to 10 moles based on 1 mole of Compound (M30).

(Production Method of Intermediate 28)

Compound (F) can be produced by reacting Compound (G) with an aminating agent:

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wherein, X^g, R⁶, R⁷, A¹, A², and A³are as defined the above.

Compound (F) can be produced according to the method described in Step (I20-3) of Production method of intermediate 20 using Compound (G) instead of Compound (M20).

Examples of Compound (B) include the following compounds:

An amide compound of the formula (6):

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wherein, R¹, R², R³, R⁹, R⁵, R⁶, R⁷, R⁸, A², A³, and n are as defined above (referred to as Compound (6));

An amide compound of the formula (10):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above (referred to as Compound (10));

An amide compound of the formula (35):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A², A³, and n are as defined above (referred to as Compound (35));

An amide compound of the formula (1B):

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wherein:

A^1brepresents —NR^8b—, an oxygen atom or a sulfur atom;

A^2brepresents a nitrogen atom or ═CR^9b—;

A^3brepresents a nitrogen atom or ═CR^10b—.

R^1brepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

R^2b, R^3b, R^4b, and R^5bare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11b, —S(O)_mR^11b, —SF₅, a cyano group, a nitro group, a halogen atom, or a hydrogen atom: provided that at least two of R^2b, R^3b, R^4b, and R^5brepresent a hydrogen atom;

R^6brepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11b, —S(O)_mR^11b, —SF₅, a cyano group, a nitro group, or a halogen atom;

R^7brepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11b, —S(O)_mR^11b, —SF₅, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^8brepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

R^9band R^10bare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11b, —S(O)_mR^11b, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^11band R^12bare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom; and

m represents 0, 1, or 2, and n represents 0, 1, or 2;

provided that: in —S(O)_mR^11b, when m is 1 or 2, R^11bis not a hydrogen atom; and when A^1bis an oxygen atom, and A^2bis a methine group, any one of R^2b, R^3b, R^4b, and R^5bare a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11b, —S(O)_mR^11b, a cyano group, a nitro group, or a halogen atom (hereinafter, referred to as Compound (1B));

And examples of Compound (1B) include the following compounds:

An amide compound of the formula (1B) wherein A^1bis —NR^8b—;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C1-C6 alkyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C1-C3 alkyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a methyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis an ethyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a propyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis an isopropyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a methoxymethyl group or an ethoxymethyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, and R^8bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis an oxygen atom;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, and R^8bis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, and R^8bis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, and A^3bis ═CR^10b—;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare same or different and are independently a halogen atom or a hydrogen atom;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare a hydrogen atom;

An amide compound of the formula (1B) wherein A^2bis a nitrogen atom, and A^3bis ═CR^10b—;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, R^9bis a halogen atom or a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^2bis ═CR^9b—, R^9bis a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^2bis a nitrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, A^2bis ═CR^9b—, and A^3bis ═CR^10b—;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis an oxygen atom, A^2bis ═CR^9b—, and A^3bis ═CR^10b—;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^2bis ═CR^9b—, and A^3bis ═CR^10b—.

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, A^2bis ═CR^9b—, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, A²b is ═CR^9b—, R^9bis a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis an oxygen atom, A^2bis ═CR^9b—, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^2bis ═CR^9b—, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^2bis ═CR^9b—, R^9bis a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, R^8bis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, R^8bis a methyl group, A^2bis ═CR^9b—, A^3bis ═CR^10b—, and R^9band R^10bare a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, R^8bis a methyl group, an ethyl group, a propyl group or an isopropyl group, A^2bis ═CR^9b—, R^9bis a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, R^8bis a methyl group, A^2bis ═CR^9b—, R^9bis a hydrogen atom, and A^3bis a nitrogen atom;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 chain hydrocarbon group optionally having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 alkyl group;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^1bis a C1-C3 alkyl group;

An amide compound of the formula (1B) wherein R^1bis a C1-C3 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^1bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group;

An amide compound of the formula (1B) wherein R^1bis a methyl group;

An amide compound of the formula (1B) wherein R^1bis an ethyl group;

An amide compound of the formula (1B) wherein R^1bis a propyl group;

An amide compound of the formula (1B) wherein R^1bis an isopropyl group;

An amide compound of the formula (1B) wherein R^1bis a trifluoromethyl group;

An amide compound of the formula (1B) wherein R^1bis a 2,2,2-trifluoroethyl group;

An amide compound of the formula (1B) wherein R^1bis a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^1bis a C3-C6 alicyclic hydrocarbon group;

An amide compound of the formula (1B) wherein R^1bis a cyclopropyl group, a cyclobutyl group, or a cyclopentyl group;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently —OR^11bor a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently —S(O)_mR^11bor a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently a cyano group, a nitro group, or a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare same or different and are independently a halogen atom or a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^3b, R^4b, and R^5bare a hydrogen atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, or a 3-chloro-5-trifluoromethyl-2-pyridyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 2-pyridyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 2-pyrimidyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 3-chloro-2-pyridyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 3-chloro-5-trifluoromethyl-2-pyridyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C6 alkyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C6 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C3 alkyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C3 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^2b, and R^5bare a hydrogen atom, and R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a methyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis an ethyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a propyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis an isopropyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a trifluoromethyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a pentafluoroethyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a heptafluoropropyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a halogen atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a fluorine atom, a chlorine atom, or a bromine atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a fluorine atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a chlorine atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a bromine atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis —SF₅;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

An amide compound of the formula (1B) wherein R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 alkyl group, R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^1bis a C1-C6 alkyl group, R^2b, R^4b, and R^5bare a hydrogen atom, and R^3bis a halogen atom;

An amide compound of the formula (1B) wherein R^6bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^6bis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1B) wherein R^6bis a C1-C6 chain hydrocarbon group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^6bis a C1-C3 alkyl group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethyl group;

An amide compound of the formula (1B) wherein R^6bis a pentafluoroethyl group;

An amide compound of the formula (1B) wherein R^6bis a heptafluoropropyl group;

An amide compound of the formula (1B) wherein R^6bis a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^6bis a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or a C1-C3 alkyl groups optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^6bis —OR^11b;

An amide compound of the formula (1B) wherein R^6bis a C1-C6 alkoxy group having one ore more fluorine atoms;

An amide compound of the formula (1B) wherein R^6bis a C1-C3 alkoxy group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethoxy group;

An amide compound of the formula (1B) wherein R^6bis —S(O)_mR^11b;

An amide compound of the formula (1B) wherein R^6bis a C1-C6 alkylsulfanyl group having one or more fluorine atoms, a C1-C6 alkylsulfinyl group having one or more fluorine atoms, or a C1-C6 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (13) wherein R^6bis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethylsulfanyl group;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethylsulfinyl group;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethylsulfonyl group;

An amide compound of the formula (1B) wherein R^6bis a cyano group or a nitro group;

An amide compound of the formula (1B) wherein R^6bis a halogen atom;

An amide compound of the formula (1B) wherein R^6bis a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1B) wherein R^6bis a chlorine atom;

An amide compound of the formula (1B) wherein R^6bis a bromine atom;

An amide compound of the formula (1B) wherein R^6bis an iodine atom;

An amide compound of the formula (1B) wherein R^6bis —SF₅;

An amide compound of the formula (1B) wherein R^6bis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

An amide compound of the formula (1B) wherein R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1B) wherein R^7bis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^7bis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1B) wherein R^7bis a C1-C6 chain hydrocarbon group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a C1-C3 alkyl group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethyl group;

An amide compound of the formula (1B) wherein R^7bis a pentafluoroethyl group;

An amide compound of the formula (1B) wherein R^7bis a heptafluoropropyl group;

An amide compound of the formula (1B) wherein R^7bis a heptafluoroisopropyl group;

An amide compound of the formula (1B) wherein R^7bis a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

An amide compound of the formula (1B) wherein R^7bis —OR^11b;

An amide compound of the formula (1B) wherein R^7bis a C1-C6 alkoxy group having one ore more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a C1-C3 alkoxy group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethoxy group;

An amide compound of the formula (1B) wherein R^7bis —S(O)_mR^11b;

An amide compound of the formula (1B) wherein R^7bis a C1-C6 alkylsulfanyl group having one or more fluorine atoms, a C1-C6 alkylsulfinyl group having one or more fluorine atoms, or a C1-C6 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethylsulfanyl group;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethylsulfinyl group;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethylsulfonyl group;

An amide compound of the formula (1B) wherein R^7bis a cyano group or a nitro group;

An amide compound of the formula (1B) wherein R^7bis a halogen atom;

An amide compound of the formula (1B) wherein R^7bis a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1B) wherein R^7bis a chlorine atom;

An amide compound of the formula (1B) wherein R^7bis a bromine atom;

An amide compound of the formula (1B) wherein R^7bis an iodine atom;

An amide compound of the formula (1B) wherein R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein R^7bis —SF₅;

An amide compound of the formula (1B) wherein R^7bis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

An amide compound of the formula (1B) wherein R^7bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1B) wherein m is 0;

An amide compound of the formula (1B) wherein m is 1;

An amide compound of the formula (1B) wherein m is 2;

An amide compound of the formula (1B) wherein n is 0;

An amide compound of the formula (1B) wherein n is 1;

An amide compound of the formula (1B) wherein n is 2;

An amide compound of the formula (1B) wherein A^1bis —NR^9b— or a sulfur atom, R^8bis a C1-C6 alkyl group, A^1bis ═CR^9b—, A^3bis ═CR^10b—, R^9band R^10bare a hydrogen atom, R^1bis a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6bis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b— or a sulfur atom, R^8bis a C1-C6 alkyl group, A^2bis ═CR^9b—, R^9bis a hydrogen atom, A^3bis a nitrogen atom, R^1bis a C1-C3 alkyl group optionally having one or more fluorine atoms, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6bis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, R^8bis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2bis ═CR^9b—, A^3bis ═CR^10b—, R^9band R^10bare a hydrogen atom, R^1bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^1bis ═CR^9b—, A^3bis ═CR^10b—, R^9band R^10bare a hydrogen atom, R^1bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group or a 2,2,2-trifluoroethyl group, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis —NR^8b—, R^8bis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2bis ═CR^9b—, R^9bis a hydrogen atom, A^3bis a nitrogen atom, R^1bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7bis a hydrogen atom;

An amide compound of the formula (1B) wherein A^1bis a sulfur atom, A^2bis ═CR^9b—, R^9bis a hydrogen atom, A^3bis a nitrogen atom, R^1bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, or a 2,2,2-trifluoroethyl group, R^2b, R^4b, and R^5bare a hydrogen atom, R^3bis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R^6bis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7bis a hydrogen atom;

And examples of Compound (6) include the following compounds:

An amide compound of the formula (6) wherein A²is ═CH—;

An amide compound of the formula (6) wherein A²is a nitrogen atom;

An amide compound of the formula (6) wherein A³is ═CH—;

An amide compound of the formula (6) wherein A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

An amide compound of the formula (6) wherein A³is a nitrogen atom;

An amide compound of the formula (6) wherein A²is ═CH—, A³is a nitrogen atom or ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

An amide compound of the formula (6) wherein A²is ═CH—, and A³is a nitrogen atom;

An amide compound of the formula (6) wherein A²is ═CH—, A³is ═CR¹⁰—, and R¹⁰is a halogen atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more atoms or groups selected from Group X;

An amide compound of the formula (6) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (6) wherein R¹is a C1-C6 chain hydrocarbon group;

An amide compound of the formula (6) wherein R¹is a C1-C3 alkyl group;

An amide compound of the formula (6) wherein R¹is a methyl group;

An amide compound of the formula (6) wherein R¹is an ethyl group;

An amide compound of the formula (6) wherein R¹is a propyl group;

An amide compound of the formula (6) wherein R¹is an isopropyl group;

An amide compound of the formula (6) wherein R², R³, R⁴, and R⁵are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —NR¹¹R¹², a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R², R⁴and R⁵are same or different and are independently a hydrogen atom or a halogen atom, R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R², R⁴and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a trifluoromethyl group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a trifluoromethoxy group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a chlorine atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a bromine atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethoxy group;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom;

An amide compound of the formula (6) wherein R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom;

An amide compound of the formula (6) wherein R², R³, R⁴, and R⁵are a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R², R⁴, and R⁵are same or different and are independently a hydrogen atom or a halogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, an iodine atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a methyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (6) wherein R¹is a methyl group, and R², R³, R⁴, and R⁵are a hydrogen atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (6) wherein R¹is an ethyl group, and R², R³, R⁴, and R⁵are a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a trifluoromethyl group or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a chlorine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a bromine atom or a hydrogen atom;

An amide compound of the formula (6) wherein R¹is a propyl group, R², R⁴, and R⁵are a hydrogen atom, and R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (6) wherein R¹is a propyl group, and R², R³, R⁴, and R⁵are a hydrogen atom;

An amide compound of the formula (6) wherein R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, —NR¹¹R¹², a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, or a halogen atom, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more halogen atoms, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more fluorine atoms, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is —OR¹¹, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is —S(O)_mR¹¹, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a C1-C6 chain hydrocarbon group having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, or a halogen atom, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein R⁸is a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a cyclopropyl group;

An amide compound of the formula (6) wherein R⁸is a methyl group, an ethyl group, a methoxymethyl group, or an ethoxymethyl group;

An amide compound of the formula (6) wherein R⁸is a methyl group;

An amide compound of the formula (6) wherein A²is ═CH—, A³is a nitrogen atom or ═CR¹⁰—, R¹⁰is a hydrogen atom, R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R¹is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R², R⁴, and R⁵are same or different and are independently a hydrogen atom or a halogen atom, R³is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, a halogen atom, or a hydrogen atom, and R⁶and R⁷are same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, a halogen atom, or a hydrogen atom;

An amide compound of the formula (6) wherein A²is ═CH—, A³is a nitrogen atom, R⁸is a methyl group or a hydrogen atom, R¹is a methyl group, an ethyl group or propyl group, R², R⁴, and R⁵are same or different and are independently a halogen atom or a hydrogen atom, R³is a trifluoromethyl group, a halogen atom or a hydrogen atom, R⁶is a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R⁷is a hydrogen atom;

An amide compound of the formula (6) wherein A²is ═CH—, A³is a nitrogen atom or ═CR¹⁰—, R¹⁰is a hydrogen atom, R⁸is a methyl group or a hydrogen atom, R¹is a methyl group, an ethyl group, or propyl group, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, a trifluoromethyl group, a trifluoromethoxy group, a chlorine atom, a bromine atom, or an iodine atom, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a bromine atom, or an iodine atom, and R⁷is a hydrogen atom.

Examples of Compound (C) include the following compounds:

An amide compound of the formula (M10):

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wherein, V², R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, A²and A³are as defined above (referred to as Compound (M10));

An amide compound of the formula (M25):

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wherein, V², R², R³, R⁴, R⁵, R⁶, R⁷, A²and A³are as defined above (referred to as Compound (M25));

An amide compound of the formula (M26):

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wherein, V², R², R³, R⁴, R⁵, R⁶, R⁷, A²and A³are as defined above (referred to as Compound (M26));

A compound of the formula (1C):

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wherein,

X^crepresents a fluorine atom or a chlorine atom;

A^1crepresents —NR^8c—, an oxygen atom, or a sulfur atom;

A^2crepresents a nitrogen atom or ═CR^9c—;

A^3crepresents a nitrogen atom or ═CR^10c—;

R^2c, R^3c, and R^5care same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms —OR^11c, —S(O)_mR^11c, —SF₅, a cyano group, a halogen atom, or a hydrogen atom: provided that at least one of R^2c, R^3c, and R^5crepresent a hydrogen atom;

R^4crepresents a hydrogen atom;

R^6crepresents a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or —SF₅;

R^7crepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11c, —S(O)_mR^11c, —SF₅, a cyano group, a halogen atom, or a hydrogen atom;

R^8crepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

R^9cand R^10care same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11c, —S(O)_mR^11c, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^11cand R^12care same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom; and

m represents 0, 1, or 2;

provided that: in —S(O)_mR^11c, when m is 1 or 2, R^11cis not a hydrogen atom; and when A^1cis —NR^8c—, and A^2cand A^3care a methine group, R^8cis a hydrogen atom or a methyl group (hereinafter, referred to as Compound (1C));

And examples of Compound (1C) include the following compounds:

An amide compound of the formula (1C) wherein X^cis a fluorine atom;

An amide compound of the formula (1C) wherein X^cis a chlorine atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C1-C6 alkyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C1-C3 alkyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a methyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis an ethyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a propyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis an isopropyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a methoxymethyl group or an ethoxymethyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, and R^8cis a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis an oxygen atom;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, and R^8cis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, and R^8cis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

An amide compound of the formula (1C) wherein A^2cis ═CR^9c—, and A^3cis ═CR^10c—;

An amide compound of the formula (1C) wherein A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care same or different and are independently a halogen atom or a hydrogen atom;

An amide compound of the formula (1C) wherein A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care a hydrogen atom;

An amide compound of the formula (1C) wherein A^2cis a nitrogen atom, and A^3cis ═CR^10c—;

An amide compound of the formula (1C) wherein A^2cis ═OR^9c—, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^2cis ═CR^9c—, R^9cis a halogen atom or a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^2cis ═CR^9c—, R^9cis a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^2cis a nitrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, A^2cis ═CR^9c—, and A^3cis ═CR^10c—;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis an oxygen atom, A^2cis ═OR^9c—, and A^3cis ═CR^10c—;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═OR^9c—, and A^3cis ═CR^10c—;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, A^2cis ═OR^9c—, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, A^2cis ═CR^9c—, R^9cis a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis an oxygen atom, A^2cis ═CR^9c—, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═CR^9c—, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═CR^9c—, R^9cis a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a methyl group, an ethyl group, a propyl group or an isopropyl group, A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a methyl group, A^2cis ═CR^9c—, A^3cis ═CR^10c—, and R^9cand R^10care a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a methyl group, an ethyl group, a propyl group or an isopropyl group, A^2cis ═CR^9c—, R^9cis a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a methyl group, A^2cis ═CR^9c—, R^9cis a hydrogen atom, and A^3cis a nitrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently —OR^11cor a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently —S(O)_mR^11cor a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently a cyano group, a nitro group, or a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5care same or different and are independently a halogen atom or a hydrogen atom;

An amide compound of the formula (1C) wherein R^2c, R^3c, and R^5cis a hydrogen atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, or a 3-chloro-5-trifluoromethyl-2-pyridyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 2-pyridyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 2-pyrimidyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 3-chloro-2-pyridyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 3-chloro-5-trifluoromethyl-2-pyridyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C6 alkyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C6 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C3 alkyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C3 alkyl group optionally having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a methyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis an ethyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a propyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis an isopropyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a trifluoromethyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a pentafluoroethyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a heptafluoropropyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a halogen atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a fluorine atom, a chlorine atom, or a bromine atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a fluorine atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a chlorine atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a bromine atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis —SF₅;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom;

An amide compound of the formula (1C) wherein R^2cand R^5care a hydrogen atom, and R^3cis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

An amide compound of the formula (1C) wherein R^6cis a C1-C3 alkyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethyl group;

An amide compound of the formula (1C) wherein R^6cis a pentafluoroethyl group;

An amide compound of the formula (1C) wherein R^6cis a heptafluoropropyl group;

An amide compound of the formula (1C) wherein R^6cis a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^6cis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethylsulfanyl group;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethylsulfinyl group;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethylsulfonyl group;

An amide compound of the formula (1C) wherein R^6cis —SF₅;

An amide compound of the formula (1C) wherein R^6cis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

An amide compound of the formula (1C) wherein R^7cis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein R^7cis a C1-C6 chain hydrocarbon group;

An amide compound of the formula (1C) wherein R^7cis a C1-C6 chain hydrocarbon group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a C1-C3 alkyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethyl group;

An amide compound of the formula (1C) wherein R^7cis a pentafluoroethyl group;

An amide compound of the formula (1C) wherein R^7cis a heptafluoropropyl group;

An amide compound of the formula (1C) wherein R^7cis a heptafluoroisopropyl group;

An amide compound of the formula (1C) wherein R^7cis a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

An amide compound of the formula (1C) wherein R^7cis —OR^11c;

An amide compound of the formula (1C) wherein R^7cis a C1-C6 alkoxy group having one ore more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a C1-C3 alkoxy group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethoxy group;

An amide compound of the formula (1C) wherein R^7cis —S(O)_mR^11c;

An amide compound of the formula (1C) wherein R^7cis a C1-C6 alkylsulfanyl group having one or more fluorine atoms, a C1-C6 alkylsulfinyl group having one or more fluorine atoms, or a C1-C6 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethylsulfanyl group;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethylsulfinyl group;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethylsulfonyl group;

An amide compound of the formula (1C) wherein R^7cis a cyano group or a nitro group;

An amide compound of the formula (1C) wherein R^7cis a halogen atom;

An amide compound of the formula (1C) wherein R^7cis a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1C) wherein R^7cis a chlorine atom;

An amide compound of the formula (1C) wherein R^7cis a bromine atom;

An amide compound of the formula (1C) wherein R^7cis an iodine atom;

An amide compound of the formula (1C) wherein R^7cis a hydrogen atom;

An amide compound of the formula (1C) wherein R^7cis —SF₅;

An amide compound of the formula (1C) wherein R^7cis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

An amide compound of the formula (1C) wherein R^7cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom;

An amide compound of the formula (1C) wherein m is 0;

An amide compound of the formula (1C) wherein m is 1;

An amide compound of the formula (1C) wherein m is 2;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a C1-C6 alkyl group, A^2cis ═CR^9c—, A^3cis ═CR^10c—, R^9cand R^10care a hydrogen atom, R^2cand R^5care a hydrogen atom, R^3cis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6cis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R^7cis a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c— or a sulfur atom, R^8cis a C1-C6 alkyl group, A^2cis ═CR^9c—, R^9cis a hydrogen atom, A^3cis a nitrogen atom, R^2cand R^5care a hydrogen atom, R^3cis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6cis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R^7cis a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis —NR^8c—, R^8cis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2cis ═CR^9c—, A^3cis ═CR^10c—, R^9cand R^10care a hydrogen atom, R^2cand R^5care a hydrogen atom, R^3cis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7cis a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═CR^9c—, A^3cis ═CR^10c—, R^9cand R^10care a hydrogen atom, R^2cand R^5care a hydrogen atom, R^3cis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7cis a hydrogen atom;

An amide compound of the formula wherein A^1cis —NR^8c—, R^8cis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2cis ═CR^9c—, R^9cis a hydrogen atom, A^3cis a nitrogen atom, R^2cand R^5care a hydrogen atom, R^3cis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7cis a hydrogen atom;

An amide compound of the formula (1C) wherein A^1cis a sulfur atom, A^2cis ═CR^9c—, R^9cis a hydrogen atom, A^3cis a nitrogen atom, R²and R^5care a hydrogen atom, R^3cis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom or a bromine atom, R^6cis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7cis a hydrogen atom.

Examples of Compound (24) include the following compounds:

A compound of the formula (1D):

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wherein:

A^1drepresents —NR^8d—, an oxygen atom, or a sulfur atom;

A^2drepresents a nitrogen atom or ═CR^9d—;

A^3drepresents a nitrogen atom or ═CR^10d—;

R^2d, R^3d, R^4d, and R^5dare same ore different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11d, —S(O)_mR^11d, —SF₅, a cyano group, a nitro group, a halogen atom, or a hydrogen atom: provided that at least two of R^2d, R^3d, R^4d, and R^5drepresent a hydrogen atom;

R^6drepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11d, —S(O)_mR^11d, —SF₅, a cyano group, a nitro group, or a halogen atom;

R^7drepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —S(O)_mR^11d, —SF₅, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^8drepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

R^9dand R^10dare same ore different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^11dand R^12dare same ore different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom; and

m represents 0, 1, or 2:

provided that in —S(O)_mR^11d, R^11dis not a hydrogen atom (hereinafter, referred to as Compound (1D));

And examples of Compound (1D) include the following compounds:

A compound of the formula (1D) wherein A^1dis —NR^8d—;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C1-C6 chain hydrocarbon group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C1-C6 alkyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C1-C3 alkyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a methyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis an ethyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a propyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis an isopropyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a methoxymethyl group or an ethoxymethyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d—, and R^8dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis an oxygen atom;

A compound of the formula (1D) wherein A^1dis a sulfur atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, and R^8dis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, and R^8dis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, and A^3dis ═CR^10d—;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare a hydrogen atom;

A compound of the formula (1D) wherein A^2dis a nitrogen atom, and A^3dis ═CR^10d—;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, R^9dis a halogen atom or a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^2dis ═CR^9d—, R^9dis a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^2dis a nitrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d—, A^2dis ═CR^9d—, and A^3dis ═CR^10d—;

A compound of the formula (1D) wherein A^1dis —NR^8d—, A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare a hydrogen atom;

A compound of the formula (1D) wherein A^1dis an oxygen atom, A^2dis ═CR^9d—, and A^3dis ═CR^10d—;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, and A^3dis ═CR^10d—;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d—, A^2dis ═CR^9d—, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d—, A^2dis ═CR^9d—, R^9dis a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis an oxygen atom, A^2dis ═CR^9d—, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, R^9dis a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, R^8dis a methyl group, an ethyl group, a propyl group or an isopropyl group, A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, R^8dis a methyl group, A^2dis ═CR^9d—, A^3dis ═CR^10d—, and R^9dand R^10dare a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, R^8dis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2dis ═CR^9d—, R^9dis a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^9d— or a sulfur atom, R^8dis a methyl group, A^2dis ═CR^9d—, R^9dis a hydrogen atom, and A^3dis a nitrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently —OR^11dor a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently —S(O)_mR^11dor a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently a cyano group, a nitro group, or a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^3d, R^4d, and R^5dare a hydrogen atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, or a 3-chloro-5-trifluoromethyl-2-pyridyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 2-pyridyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 2-pyrimidyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 3-chloro-2-pyridyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 3-chloro-5-trifluoromethyl-2-pyridyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C6 alkyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C6 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C3 alkyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a methyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis an ethyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a propyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis an isopropyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a trifluoromethyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a pentafluoroethyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a heptafluoropropyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a halogen atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a fluorine atom, a chlorine atom or a bromine atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a fluorine atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a chlorine atom; A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a bromine atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis —SF₅;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom;

A compound of the formula (1D) wherein R^2d, R^4d, and R^5dare a hydrogen atom, and R^3dis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1D) wherein R^6dis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^6dis a C1-C6 chain hydrocarbon group;

A compound of the formula (1D) wherein R^6dis a C1-C6 chain hydrocarbon group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^6dis a trifluoromethyl group;

A compound of the formula (1D) wherein R^6dis a pentafluoroethyl group;

A compound of the formula (1D) wherein R^6dis a heptafluoropropyl group;

A compound of the formula (1D) wherein R^6dis a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^6dis a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^6dis —OR^11d;

A compound of the formula (1D) wherein R^6dis a C1-C6 alkoxy group having one ore more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a C1-C3 alkoxy group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a trifluoromethoxy group;

A compound of the formula (1D) wherein R^6dis S(O)_mR^11d;

A compound of the formula (1D) wherein R^6dis a C1-C6 alkylsulfanyl group having one or more fluorine atoms, a C1-C6 alkylsulfinyl group having one or more fluorine atoms, or a C1-C6 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^6dis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1D) wherein R^6dis a trifluoromethylsulfanyl group;

A compound of the formula (1D) wherein R^6dis a trifluoromethylsulfinyl group;

A compound of the formula (1D) wherein R^6dis a trifluoromethylsulfonyl group;

A compound of the formula (1D) wherein R^6dis a cyano group or a nitro group;

A compound of the formula (1D) wherein R^6dis a halogen atom;

A compound of the formula (1D) wherein R^6dis a chlorine atom, a bromine atom, or an iodine atom;

A compound of the formula (1D) wherein R^6dis a chlorine atom;

A compound of the formula (1D) wherein R^6dis a bromine atom;

A compound of the formula (1D) wherein R^6dis an iodine atom;

A compound of the formula (1D) wherein R^6dis —SF₅;

A compound of the formula (1D) wherein R^6dis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1D) wherein R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom;

A compound of the formula (1D) wherein R^7dis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^7dis a C1-C6 chain hydrocarbon group;

A compound of the formula (1D) wherein R^7dis a C1-C6 chain hydrocarbon group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^7dis a trifluoromethyl group;

A compound of the formula (1D) wherein R^7dis a pentafluoroethyl group;

A compound of the formula (1D) wherein R^7dis a heptafluoropropyl group;

A compound of the formula (1D) wherein R^7dis a heptafluoroisopropyl group;

A compound of the formula (1D) wherein R^7dis a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1D) wherein R^7dis —OR^11d;

A compound of the formula (1D) wherein R^7dis a C1-C6 alkoxy group having one ore more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a C1-C3 alkoxy group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a trifluoromethoxy group;

A compound of the formula (1D) wherein R^7dis —S(O)_mR^11d;

A compound of the formula (1D) wherein R^7dis a C1-C6 alkylsulfanyl group having one or more fluorine atoms, a C1-C6 alkylsulfinyl group having one or more fluorine atoms, or a C1-C6 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1D) wherein R^7dis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1D) wherein R^7dis a trifluoromethylsulfanyl group;

A compound of the formula (1D) wherein R^7dis a trifluoromethylsulfinyl group;

A compound of the formula (1D) wherein R^7dis a trifluoromethylsulfonyl group;

A compound of the formula (1D) wherein R^7dis a cyano group or a nitro group;

A compound of the formula (1D) wherein R^7dis a halogen atom;

A compound of the formula (1D) wherein R^7dis a chlorine atom, a bromine atom, or an iodine atom;

A compound of the formula (1D) wherein R^7dis a chlorine atom;

A compound of the formula (1D) wherein R^7dis a bromine atom;

A compound of the formula (1D) wherein R^7dis an iodine atom;

A compound of the formula (1D) wherein R^7dis a hydrogen atom;

A compound of the formula (1D) wherein R^7dis —SF₅;

A compound of the formula (1D) wherein R^7dis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1D) wherein R^7dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom;

A compound of the formula (1D) wherein R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein m is 0;

A compound of the formula (1D) wherein m is 1;

A compound of the formula (1D) wherein m is 2;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, R^8dis a C1-C6 alkyl group, A^2dis ═CR^9d—, A^3dis ═CR^10d—, R^9dand R^10dare a hydrogen atom, R^2d, R^4d, R^5dare a hydrogen atom, R^3dis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6dis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d— or a sulfur atom, R^8dis a C1-C6 alkyl group, A^2dis ═CR^9d—, R^9dis a hydrogen atom, A^3dis a nitrogen atom, R^2d, R^4d, and R^5dare a hydrogen atom, R^3dis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6dis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or a halogen atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d—, R^8dis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2dis ═CR^9d—, A^3dis ═CR^10d—, R^9dand R^10dare a hydrogen atom, R^2d, R^4d, and R^5dare a hydrogen atom, R^3dis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, A^3dis ═CR^10d—, R^9dand R^10dare a hydrogen atom, R^2d, R^4d, and R^5dare a hydrogen atom, R^3dis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis —NR^8d—, R^8dis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2dis ═CR^9d—, R^9dis a hydrogen atom, A^3dis a nitrogen atom, R^2d, R^4d, and R^5dare a hydrogen atom, R^3dis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7dis a hydrogen atom;

A compound of the formula (1D) wherein A^1dis a sulfur atom, A^2dis ═CR^9d—, R^9dis a hydrogen atom, A^3dis a nitrogen atom, R^2d, R^4d, and R^5dare a hydrogen atom, R^3dis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6dis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a chlorine atom, a bromine atom, or an iodine atom, and R^7dis a hydrogen atom.

Examples of Compound (21) include the following compounds:

A compound of the formula (1E):

embedded image

wherein:

X^erepresents a fluorine atom or a chlorine atom;

A^1erepresents —NR^8e—, an oxygen atom or a sulfur atom;

A^2erepresents a nitrogen atom or ═CR^9e—;

R^2e, R^3e, and R^5eare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms —OR^11e, —S(O)_mR^11e, —SF₅, a cyano group, a halogen atom, or a hydrogen atom: provided that at least one of R^2e, R^3e, and R^5erepresent a hydrogen atom;

R^4erepresents a hydrogen atom;

R^6erepresents a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, or —SF₅;

R^7erepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11e, —S(O)_mR^11e, —SF₅, a cyano group, a halogen atom, or a hydrogen atom;

R^8erepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group, a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

R^9eand R^10eare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11e, —S(O)_mR^11e, a cyano group, a nitro group, a halogen atom, or a hydrogen atom;

R^11eand R^12eare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom; and

m represents 0, 1, or 2:

provided that; in —S(O)_mR^11e, when m is 1 or 2, R^11eis not a hydrogen atom; when A^1eis an oxygen atom, and A^2eand A^3eare a methine group, one of R^2e, R^3e, and R^5eare a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, —OR^11e, —S(O)_mR^11e, a cyano group, a nitro group, or a halogen atom, and two others are a hydrogen atom; and when A^1eis —NR^8e—, and A^2eis a methine group, R^8eis a methyl group (hereinafter, referred to as Compound (1E));

Examples of Compound (1E) include the following compounds:

A compound of the formula (1E) wherein X^eis a fluorine atom;

A compound of the formula (1E) wherein X^eis a chlorine atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C1-C6 chain hydrocarbon group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C1-C6 alkyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C1-C3 alkyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1E) wherein is —NR^8e—, and R^8eis a methyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis an ethyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a propyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis an isopropyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C1-C6 chain hydrocarbon group having one C1-C6 alkoxy group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a methoxymethyl group or an ethoxymethyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a C3-C6 alicyclic hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, or a cyclohexyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e—, and R^8eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis an oxygen atom;

A compound of the formula (1E) wherein A^1eis a sulfur atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, and R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, and R^8eis a methoxymethyl group, an ethoxymethyl group, or a hydrogen atom;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, and A^3eis ═CR^10e—;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare a hydrogen atom;

A compound of the formula (1E) wherein A^2eis a nitrogen atom, and A^3eis ═CR^10e—;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, R^9eis a halogen atom or a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^2eis ═CR^9e—, R^9eis a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^2eis a nitrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—, A^2eis ═CR^9e—, and A^3eis ═CR^10e—;

A compound of the formula (1E) wherein A^1eis —NR^8e—, A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare a hydrogen atom;

A compound of the formula (1E) wherein A^1eis an oxygen atom, A^2eis ═CR^9e—, and A^3eis ═CR^10e—;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, and A^3eis ═CR^10e—;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—, A^2eis ═CR^9e—, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—, A^2eis ═CR^9e—, R^9eis a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis an oxygen atom, A^2eis ═CR^9e—, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, R^9eis a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, R^8eis a methyl group, A^2eis ═CR^9e—, A^3eis ═CR^10e—, and R^9eand R^10eare a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2eis ═CR^9e—, R^9eis a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, R^8eis a methyl group, A^2eis ═CR^9e—, R^9eis a hydrogen atom, and A^3eis a nitrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, or a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently a phenyl group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 5-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms, or a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently —OR^11eor a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently —S(O)_mR^11eor a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently a cyano group, a nitro group, or a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare a hydrogen atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, R^3eis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, or a 3-chloro-5-trifluoromethyl-2-pyridyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 2-pyridyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 2-pyrimidyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 3-chloro-2-pyridyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 3-chloro-5-trifluoromethyl-2-pyridyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C6 alkyl group; A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C6 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C3 alkyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a methyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis an ethyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a propyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis an isopropyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a trifluoromethyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a pentafluoroethyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a heptafluoropropyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a halogen atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a fluorine atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a chlorine atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a bromine atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis —SF₅;

A compound of the formula (1E) wherein R^2e, R^3e, and R^5eare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 6-membered heterocyclic group optionally having one or more halogen atoms or C1-C3 alkyl groups optionally having one or more halogen atoms;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a halogen atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a C1-C3 alkyl group optionally having one or more fluorine atoms, or a halogen atom;

A compound of the formula (1E) wherein R^2eand R^5eare a hydrogen atom, and R^3eis a 2-pyridyl group, a 2-pyrimidyl group, a 3-chloro-2-pyridyl group, a 3-chloro-5-trifluoromethyl-2-pyridyl group, a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1E) wherein R^6eis a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^6eis a trifluoromethyl group;

A compound of the formula (1E) wherein R^6eis a pentafluoroethyl group;

A compound of the formula (1E) wherein R^6eis a heptafluoropropyl group;

A compound of the formula (1E) wherein R^6eis a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^6eis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^6eis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^6eis a trifluoromethylsulfanyl group;

A compound of the formula (1E) wherein R^6eis a trifluoromethylsulfinyl group;

A compound of the formula (1E) wherein R^6eis a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^6eis —SF₅;

A compound of the formula (1E) wherein R^6eis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^7eis a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^7eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, or a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^7eis a trifluoromethyl group;

A compound of the formula (1E) wherein R^7eis a pentafluoroethyl group;

A compound of the formula (1E) wherein R^7eis a heptafluoropropyl group;

A compound of the formula (1E) wherein R^7eis a heptafluoroisopropyl group;

A compound of the formula (1E) wherein R^7eis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^7eis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^7eis a trifluoromethylsulfanyl group;

A compound of the formula (1E) wherein R^7eis a trifluoromethylsulfinyl group;

A compound of the formula (1E) wherein R^7eis a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^7eis —SF₅;

A compound of the formula (1E) wherein R^7eis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1E) wherein R^7eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1E) wherein R^6eis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkoxy group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein m is 0;

A compound of the formula (1E) wherein m is 1;

A compound of the formula (1E) wherein m is 2;

A compound of the formula (1E) wherein A^1eis —NR^9e— or a sulfur atom, R^8eis a C1-C6 alkyl group, A^2eis ═CR^{9e—, A}^3eis ═CR^10e—, R^9eand R^10eare a hydrogen atom, R^2eand R^5eare a hydrogen atom, R^3eis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6eis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e— or a sulfur atom, R^8eis a C1-C6 alkyl group, A^2eis ═CR^9e—, R^9eis a hydrogen atom, A^3eis a nitrogen atom, R^2eand R^5eare a hydrogen atom, R^3eis a C1-C3 alkyl group optionally having one or more fluorine atoms or a halogen atom, R^6eis a C1-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—, R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2wis ═CR^9e—, A^3eis ═CR^10e—, R^9eand R^10eare a hydrogen atom, R^2eand R^5eare a hydrogen atom, R^3eis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, A^3eis ═CR^10e—, R^9eand R^10eare a hydrogen atom, R^2eand R^5eare a hydrogen atom, R^3eis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis —NR^8e—, R^8eis a methyl group, an ethyl group, a propyl group, or an isopropyl group, A^2eis ═CR^9e—, R^9eis a hydrogen atom, A^3eis a nitrogen atom, R^2eand R^5eare a hydrogen atom, R^3eis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7eis a hydrogen atom;

A compound of the formula (1E) wherein A^1eis a sulfur atom, A^2eis ═CR^9e—, R^9eis a hydrogen atom, A^3eis a nitrogen atom, R^2e, R^4eand R^5eare a hydrogen atom, R^3eis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a fluorine atom, a chlorine atom, or a bromine atom, R^6eis a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, and R^7eis a hydrogen atom.

Examples of Compound (F) include the following compounds:

A compound of the formula (M21):

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wherein, R⁶, R⁷, R⁸and A²are as defined above (referred to as Compound (M21));

A compound of the formula (1F):

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wherein:

A^2frepresents a nitrogen atom or ═CR^9f—;

A^3frepresents a nitrogen atom or ═CR^10f—;

R^6frepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11f, —S(O)_mR^11f, —SF₅, or a halogen atom;

R^7frepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11f, —S(O)_mR^11f, —SF₅, hydrogen atom, or a halogen atom;

R^8frepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

R^9fand R^10fare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom, or a hydrogen atom;

R^11fand R^12fare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

m represents 0, 1, or 2:

provided that in —S(O)_mR^11f, when m is 1 or 2, R^11fis not a hydrogen atom (hereinafter, referred to as Compound (1F));

And examples of Compound (1F) include the following compounds:

A compound of the formula (1F) wherein A^2fis ═CR^9f—, and A^3fis ═CR^10f—;

A compound of the formula (1F) wherein A^2fis a nitrogen atom, and A^3fis ═CR^10f—;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, and A^3fis a nitrogen atom;

A compound of the formula (1F) wherein A^2fis a nitrogen atom, and A^3fis a nitrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, and A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, and A^3fis a nitrogen atom;

A compound of the formula (1F) wherein R^6fis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1F) wherein R^6fis a C2-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1F) wherein R^6fis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1F) wherein R^6fis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, or an iodine atom;

A compound of the formula (1F) wherein R^6fis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1F) wherein R^6fis a pentafluoroethyl group;

A compound of the formula (1F) wherein R^6fis a trifluoromethylsulfanyl group;

A compound of the formula (1F) wherein R^6fis a trifluoromethylsulfinyl group;

A compound of the formula (1F) wherein R^6fis a trifluoromethylsulfonyl group;

A compound of the formula (1F) wherein R^6fis an iodine atom;

A compound of the formula (1F) wherein R^6fis —SF₅;

A compound of the formula (1F) wherein R^7fis a hydrogen atom;

A compound of the formula (1F) wherein R^8fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein R^8fis a C1-C3 alkyl group;

A compound of the formula (1F) wherein R^8fis a methyl group;

A compound of the formula (1F) wherein R^8fis an ethyl group;

A compound of the formula (1F) wherein R^8fis a propyl group;

A compound of the formula (1F) wherein R^8fis a hydrogen atom;

A compound of the formula (1F) wherein R^8fis a methyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a C2-C3 alkyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group or an iodine atom, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group or a hydrogen atom: provided that when R^6fis an iodine atom, R^8fis a C1-C3 alkyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R^7fis a hydrogen atom, and R^8fis a methyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a pentafluoroethyl group, R^7fis a hydrogen atom, and R^8fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a trifluoromethylsulfanyl group, R^7fis a hydrogen atom, and R^8fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis a trifluoromethylsulfonyl group, R^7fis a hydrogen atom, and R^8fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis an iodine atom, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, R^9fis a hydrogen atom, A^3fis a nitrogen atom, R^6fis an iodine atom, R^7fis a hydrogen atom, and R^8fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^8fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a C2-C3 alkyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^6fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7fis a hydrogen atom, and R^6fis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R^7fis a hydrogen atom, and R^6fis a methyl group or a hydrogen atom;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a pentafluoroethyl group, R^7fis a hydrogen atom, and R^6fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a trifluoromethylsulfanyl group, R^7fis a hydrogen atom, and R^6fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis a trifluoromethylsulfonyl group, R^7fis a hydrogen atom, and R^8fis a methyl group;

A compound of the formula (1F) wherein A^2fis ═CR^9f—, A^3fis ═CR^10f—, R^9fand R^10fare a hydrogen atom, R^6fis —SF₅, R^7fis a hydrogen atom, and R^8fis a methyl group;

And examples of Compound (M21) include the following compounds:

A compound of the formula (M21) wherein A²is ═CH—;

A compound of the formula (M21) wherein A²is nitrogen;

A compound of the formula (M21) wherein R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or hydrogen;

A compound of the formula (M21) wherein R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein R⁸is a C1-C3 alkyl group;

A compound of the formula (M21) wherein R⁸is a methyl group, an ethyl group, a propyl group, or hydrogen;

A compound of the formula (M21) wherein R⁸is a methyl group;

A compound of the formula (M21) wherein R⁸is an ethyl group;

A compound of the formula (M21) wherein R⁸is a propyl group;

A compound of the formula (M21) wherein R⁸is hydrogen;

A compound of the formula (M21) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a bromine atom, or an iodine atom;

A compound of the formula (M21) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, or a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein R⁶is a C1-C6 alkoxy group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein R⁶is a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, or a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein R⁶is a bromine atom or an iodine atom;

A compound of the formula (M21) wherein R⁶is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (M21) wherein R⁶is a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (M21) wherein R⁶is a pentafluoroethyl group;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfanyl group;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfinyl group;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfonyl group;

A compound of the formula (M21) wherein R⁶is a pentafluoroethyl group, and R⁷is hydrogen;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfanyl group, and R⁷is hydrogen;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfinyl group, and R⁷is hydrogen;

A compound of the formula (M21) wherein R⁶is a trifluoromethylsulfonyl group, and R⁷is hydrogen;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R⁷is hydrogen, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, or a trifluoromethylsulfanyl group, R⁷is hydrogen, and R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a trifluoromethyl group or pentafluoroethyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a pentafluoroethyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M21) wherein A²is ═CH—, R⁶is a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group.

Examples of Compound (G) include the following compounds:

A compound of the formula (M20):

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wherein, X^g, R⁶, R⁷, R⁸and A²are as defined above (referred to as Compound (M20));

A compound of the formula (1G):

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wherein:

X^grepresents a chlorine atom, a bromine atom, or an iodine atom;

A^2grepresents a nitrogen atom or ═CR^9g—;

A^3grepresents a nitrogen atom or ═CR^10g—;

R^6grepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11g, —S(O)_mR^11g, —SF₅, or a halogen atom;

R^7grepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11g, —S(O)_mR^11g, —SF₅, or a halogen atom;

R^8grepresents a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

R^9gand R^10gare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a halogen atom or a hydrogen atom;

R^11gand R^12gare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

m represents 0, 1, or 2:

provided that in —S(O)_mR^11g, when m is 1 or 2, R^11gis not a hydrogen atom (hereinafter, referred to as Compound (1G));

And examples of Compound (1G) include the following compounds:

A compound of the formula (1G) wherein X^gis a chlorine atom;

A compound of the formula (1G) wherein X^gis a bromine atom;

A compound of the formula (1G) wherein X^gis an iodine atom;

A compound of the formula (1G) wherein A^2gis ═CR^9g—, and A^3gis ═CR^10g—;

A compound of the formula (1G) wherein A^2gis a nitrogen atom, and A^3gis ═CR^10g—;

A compound of the formula (1G) wherein A^2gis ═CR^9g—, and A^3gis a nitrogen atom;

A compound of the formula (1G) wherein A^2gis a nitrogen atom, and A^3gis a nitrogen atom;

A compound of the formula (1G) wherein A^2gis ═CR^9g—, A^3gis ═CR^10g—, and R^9gand R^10gare a hydrogen atom;

A compound of the formula (1G) wherein A^2gis ═CR^9g—, R^9gis a hydrogen atom, and A^3gis a nitrogen atom;

A compound of the formula (1G) wherein R^6gis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1G) wherein R^6gis a C2-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1G) wherein R^6gis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms;

A compound of the formula (1G) wherein R^6gis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, or an iodine atom;

A compound of the formula (1G) wherein R^6gis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1G) wherein R^6gis a pentafluoroethyl group;

A compound of the formula (1G) wherein R^6gis a trifluoromethylsulfanyl group;

A compound of the formula (1G) wherein R^6gis a trifluoromethylsulfinyl group;

A compound of the formula (1G) wherein R^6gis a trifluoromethylsulfonyl group;

A compound of the formula (1G) wherein R^6gis an iodine atom;

A compound of the formula (1G) wherein R^6gis —SF₅;

A compound of the formula (1G) wherein R^7gis a hydrogen atom;

A compound of the formula (1G) wherein R^8gis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1G) wherein R^8gis a C1-C3 alkyl group;

A compound of the formula (1G) wherein R^8gis a methyl group;

A compound of the formula (1G) wherein R^8gis an ethyl group;

A compound of the formula (1G) wherein R^8gis a propyl group;

A compound of the formula (1G) wherein R^8gis a hydrogen atom;

A compound of the formula (1G) wherein R^8gis a methyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, or an iodine atom, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group or a hydrogen atom: provided that when R^6gis an iodine atom, R^8gis a C1-C3 alkyl group;

A compound of the formula (1G) wherein A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R^7gis a hydrogen atom, and R^8gis a methyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^8gis a pentafluoroethyl group, R^7gis a hydrogen atom, and R^8gis a methyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a trifluoromethylsulfanyl group, R^7gis a hydrogen atom, and R^8gis a methyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis a trifluoromethylsulfonyl group, R^7gis a hydrogen atom, and R^8gis a methyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, R^9gis a hydrogen atom, A^3gis a nitrogen atom, R^6gis an iodine atom, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis a C2-C3 alkyl group having one or more fluorine atoms, a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis a C1-C3 alkylsulfanyl group having one or more fluorine atoms, a C1-C3 alkylsulfinyl group having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group having one or more fluorine atoms, R^7gis a hydrogen atom, and R^8gis a C1-C3 alkyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis a pentafluoroethyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R^7gis a hydrogen atom, and R^8gis a methyl group or a hydrogen atom;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis a trifluoromethylsulfanyl group, R^7gis a hydrogen atom, and R^8gis a methyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis a trifluoromethylsulfonyl group, R^7gis a hydrogen atom, and R^8gis a methyl group;

A compound of the formula (1G) wherein X^gis a chlorine atom or a bromine atom, A^2gis ═CR^9g—, A^3gis ═CR^10g—, R^9gand R^10gare a hydrogen atom, R^6gis —SF₅, R^7gis a hydrogen atom, and R^8gis a methyl group;

And examples of Compound (M20) include the following compounds:

A compound of the formula (M20) wherein X^gis a chlorine atom;

A compound of the formula (M20) wherein X^gis a bromine atom;

A compound of the formula (M20) wherein X^gis an iodine atom;

A compound of the formula (M20) wherein A²is ═CH—;

A compound of the formula (M20) wherein A²is nitrogen;

A compound of the formula (M20) wherein R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or hydrogen;

A compound of the formula (M20) wherein R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein R⁸is a C1-C3 alkyl group;

A compound of the formula (M20) wherein R⁸is a methyl group, an ethyl group, a propyl group, or hydrogen;

A compound of the formula (M20) wherein R⁸is a methyl group;

A compound of the formula (M20) wherein R⁸is an ethyl group;

A compound of the formula (M20) wherein R⁸is a propyl group;

A compound of the formula (M20) wherein R⁸is hydrogen;

A compound of the formula (M20) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms, a bromine atom, or an iodine atom;

A compound of the formula (M20) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, a C1-C6 alkoxy group optionally having one or more halogen atoms, a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, or a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein R⁶is a C1-C6 alkoxy group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein R⁶is a C1-C6 alkylsulfanyl group optionally having one or more halogen atoms, a C1-C6 alkylsulfinyl group optionally having one or more halogen atoms, or a C1-C6 alkylsulfonyl group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein R⁶is a bromine atom or an iodine atom;

A compound of the formula (M20) wherein R⁶is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (M20) wherein R⁶is a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (M20) wherein R⁶is a pentafluoroethyl group;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfanyl group;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfinyl group;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfonyl group;

A compound of the formula (M20) wherein R⁶is a pentafluoroethyl group, and R⁷is hydrogen;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfanyl group, and R⁷is hydrogen;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfinyl group, and R⁷is hydrogen;

A compound of the formula (M20) wherein R⁶is a trifluoromethylsulfonyl group, and R⁷is hydrogen;

A compound of the formula (M20) wherein A²is ═CH—, R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R⁷is hydrogen, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein X^gis a bromine atom, A²is ═CH—, R⁶is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, R⁷is hydrogen, and R⁸is a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms;

A compound of the formula (M20) wherein A²is ═CH—, R⁶is a trifluoromethyl group, a difluoromethyl group, a fluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, or a trifluoromethylsulfanyl group, R⁷is hydrogen, and R⁸is a methyl group, an ethyl group, a propyl group, or an isopropyl group;

A compound of the formula (M20) wherein A²is ═CH—, R⁶is a trifluoromethyl group or a pentafluoroethyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M20) wherein A²is ═CH—, R⁶is a trifluoromethyl group, a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M20) wherein A²is ═CH—, R⁶is a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group;

A compound of the formula (M20) wherein X^gis a bromine atom, A²is ═CH—, R⁶is a pentafluoroethyl group, a trifluoromethoxy group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group, R⁷is hydrogen, and R⁸is a methyl group.

Examples of Compound (3), Compound (5), and Compound (M3) include the following compounds:

A compound of the formula (1H):

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wherein:

R^1hrepresents a C1-C6 alkyl group optionally having one or more halogen atoms;

R¹³represents a hydrogen atom, hydroxy group, or a chlorine atom;

R^2h, R^3h, R^4h, and R^5hare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11h, —S(O)_mR^11h, —SF₅, a halogen atom, or a hydrogen atom;

R^11hand R^12hare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom; and

n represents 0, 1, or 2 (hereinafter, referred to as Compound (1H));

And examples of Compound (1H) include the following compounds:

A compound of the formula (1H) wherein R^1his a C1-C3 alkyl group optionally having one or more halogen atoms;

A compound of the formula (1H) wherein R^1his a C1-C3 alkyl group;

A compound of the formula (1H) wherein R^1his a methyl group;

A compound of the formula (1H) wherein R^1his an ethyl group;

A compound of the formula (1H) wherein R^1his a propyl group;

A compound of the formula (1H) wherein R¹³is a hydrogen atom;

A compound of the formula (1H) wherein R¹³is hydroxy group;

A compound of the formula (1H) wherein R¹³is a chlorine atom;

A compound of the formula (1H) wherein R¹³is a hydrogen atom or hydroxy group;

A compound of the formula (1H) wherein R^2h, R^3h, R^4h, and R^5hare a hydrogen atom;

A compound of the formula (1H) wherein R^2h, R^3h, R^4h, and R^5hare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1H) wherein R^2h, R^3h, R^4h, and R^5hare same or different and are independently —OR^11hor a hydrogen atom;

A compound of the formula (1H) wherein R^2h, R^3h, R^4h, and R^5hare same or different and are independently —S(O)_mR^11hor a hydrogen atom;

A compound of the formula (1H) wherein R^2h, R^3h, R^4h, and R^5hare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11h, —S(O)_mR^11hor a halogen atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a methyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his an ethyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a propyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his an isopropyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a pentafluoroethyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a heptafluoropropyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a heptafluoroisopropyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —OR^11h;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethoxy group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —S(O)_mR^11h;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group or a trifluoromethylsulfonyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethylsulfanyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethylsulfinyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethylsulfonyl group;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a halogen atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a fluorine atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a chlorine atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a bromine atom;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —SF₅;

A compound of the formula (1H) wherein R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a fluorine atom, a chlorine atom, a bromine atom, or —SF₅;

A compound of the formula (1H) wherein n is 0;

A compound of the formula (1H) wherein n is 1;

A compound of the formula (1H) wherein n is 2;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, R^5hare same or different and are independently a halogen atom or a hydrogen atom, and R^3ha C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11h, —S(O)_mR^11h, a halogen atom, or a hydrogen atom;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a halogen atom;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a methyl group;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his an ethyl group;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethyl group;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethoxy group;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a fluorine atom;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a chlorine atom;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a bromine atom;

A compound of the formula (1H) wherein R^1his a methyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —SF₅;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare same or different and are independently a halogen atom or a hydrogen atom, and R^3ha C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^11h, —S(O)_mR^11h, a halogen atom, or a hydrogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a halogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a methyl group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a methyl group, and R¹³is hydroxy group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a methyl group, and R¹³is a chlorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a methyl group, and R¹³is a hydrogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his an ethyl group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethyl group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a trifluoromethyl group, and R¹³is hydroxy group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a trifluoromethyl group, and R¹³is a chlorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a trifluoromethyl group, and R^5his a hydrogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethoxy group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a fluorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a chlorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a chlorine atom, and R¹³is hydroxy group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a chlorine atom, and R¹³is a chlorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, R^5hare a hydrogen atom, R^3his a chlorine atom, and R¹³is a hydrogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a bromine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a bromine atom, and R¹³is hydroxy group;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a bromine atom, and R¹³is a chlorine atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, R^3his a bromine atom, and R¹³is a hydrogen atom;

A compound of the formula (1H) wherein R^1his an ethyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —SF₅;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare same or different and are independently a halogen atom or a hydrogen atom, and R^3ha C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR^1h, —S(O)_mR^11h, a halogen atom, or a hydrogen atom;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a propyl group, and R^3his a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a propyl group, and R^3his a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a halogen atom;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a methyl group;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his an ethyl group;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethyl group;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a trifluoromethoxy group;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a fluorine atom;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a chlorine atom;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his a bromine atom;

A compound of the formula (1H) wherein R^1his a propyl group, R^2h, R^4h, and R^5hare a hydrogen atom, and R^3his —SF₅.

Examples of Compound (M22) include the following compounds:

A compound of the formula (1I):

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wherein:

R¹ⁱrepresents a C1-C6 alkyl group optionally having one or more halogen atoms;

R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹ⁱ, —S(O)_mR¹¹ⁱ, —SF₅, a halogen atom, or a hydrogen atom;

R¹¹ⁱand R¹²ⁱare same or different and represent independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom; and

r represents 1 or 2 (hereinafter, referred to as Compound (1I));

And examples of Compound (1I) include the following compounds:

A compound of the formula (1I) wherein R¹ⁱis a C1-C3 alkyl group optionally having one or more halogen atoms;

A compound of the formula (1I) wherein R¹ⁱis a C1-C3 alkyl group;

A compound of the formula (1I) wherein R¹ⁱis a methyl group;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group;

A compound of the formula (1I) wherein R¹ⁱis a propyl group;

A compound of the formula (1I) wherein R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom;

A compound of the formula (1I) wherein R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms or a hydrogen atom;

A compound of the formula (1I) wherein R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently —OR¹¹ⁱor a hydrogen atom;

A compound of the formula (1I) wherein R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently —S(O)_mR¹¹ⁱor a hydrogen atom;

A compound of the formula (1I) wherein R²ⁱ, R³ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently a halogen atom or a hydrogen atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹, —S(O)_mR¹¹ⁱ, or a halogen atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group having one or more fluorine atoms;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a methyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis an ethyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a propyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis an isopropyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a pentafluoroethyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a heptafluoropropyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a heptafluoroisopropyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —OR¹¹ⁱ;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethoxy group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —S(O)_mR¹¹ⁱ;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, or a trifluoromethylsulfonyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethylsulfanyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethylsulfinyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethylsulfonyl group;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a halogen atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a fluorine atom, a chlorine atom, or a bromine atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a fluorine atom;

A compound of the formula (I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a chlorine atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a bromine atom;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —SF₅;

A compound of the formula (1I) wherein R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a methyl group, an ethyl group, a propyl group, an isopropyl group, a trifluoromethyl group, a pentafluoroethyl group, a heptafluoropropyl group, a heptafluoroisopropyl group, a trifluoromethylsulfanyl group, a trifluoromethylsulfinyl group, a trifluoromethylsulfonyl group, a fluorine atom, a chlorine atom, a bromine atom, or —SF₅;

A compound of the formula (1I) wherein r is 1;

A compound of the formula (1I) wherein r is 2;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently a halogen atom or a hydrogen atom, and R³ⁱa C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹ⁱ, —S(O)_mR¹¹ⁱ, a halogen atom, or a hydrogen atom;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a halogen atom;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a methyl group;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis an ethyl group;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethyl group;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethoxy group;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a fluorine atom;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a chlorine atom;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a bromine atom;

A compound of the formula (1I) wherein R¹ⁱis a methyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —SF₅;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently a halogen atom or a hydrogen atom, and R³ⁱa C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹ⁱ, —S(O)_mR¹¹ⁱ, a halogen atom, or a hydrogen atom;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a halogen atom;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a methyl group;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis an ethyl group;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethyl group;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethoxy group;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a fluorine atom;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a chlorine atom;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a bromine atom;

A compound of the formula (1I) wherein R¹ⁱis an ethyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —SF₅;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare same or different and are independently a halogen atom or a hydrogen atom, and R³ⁱa C1-C6 chain hydrocarbon group optionally having one or more halogen atoms, —OR¹¹ⁱ, —S(O)_mR¹¹ⁱ, a halogen atom, or a hydrogen atom;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkoxy group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a C1-C3 alkylsulfanyl group optionally having one or more fluorine atoms, a C1-C3 alkylsulfinyl group optionally having one or more fluorine atoms, or a C1-C3 alkylsulfonyl group optionally having one or more fluorine atoms;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a halogen atom;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a methyl group;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis an ethyl group;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethyl group;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a trifluoromethoxy group;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a fluorine atom;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a chlorine atom;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis a bromine atom;

A compound of the formula (1I) wherein R¹ⁱis a propyl group, R²ⁱ, R⁴ⁱ, and R⁵ⁱare a hydrogen atom, and R³ⁱis —SF₅.

Examples of the present compound are shown bellow.

A compound of the formula (A):

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wherein R², R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19:

TABLE 1

R¹
A¹
A³
n

Me
—NMe—
═N—
0

Me
—NMe—
═N—
1

Me
—NMe—
═N—
2

Et
—NMe—
═N—
0

Et
—NMe—
═N—
1

Et
—NMe—
═N—
2

Pr
—NMe—
═N—
0

Pr
—NMe—
═N—
1

Pr
—NMe—
═N—
2

iPr
—NMe—
═N—
0

iPr
—NMe—
═N—
1

iPr
—NMe—
═N—
2

tBu
—NMe—
═N—
0

tBu
—NMe—
═N—
1

tBu
—NMe—
═N—
2

CF₃
—NMe—
═N—
0

CF₃
—NMe—
═N—
1

CF₃
—NMe—
═N—
2

CH₂CF₃
—NMe—
═N—
0

CH₂CF₃
—NMe—
═N—
1

CH₂CF₃
—NMe—
═N—
2

CH═CH₂
—NMe—
═N—
0

CH═CH₂
—NMe—
═N—
1

CH═CH₂
—NMe—
═N—
2

TABLE 2

R¹
A¹
A³
n

CH₂CH═CH₂
—NMe—
═N—
0

CH₂CH═CH₂
—NMe—
═N—
1

CH₂CH═CH₂
—NMe—
═N—
2

C≡CH
—NMe—
═N—
0

C≡CH
—NMe—
═N—
1

C≡CH
—NMe—
═N—
2

CH₂C≡CH
—NMe—
═N—
0

CH₂C≡CH
—NMe—
═N—
1

CH₂C≡CH
—NMe—
═N—
2

CyPr
—NMe—
═N—
0

CyPr
—NMe—
═N—
1

CyPr
—NMe—
═N—
2

Me
—NMe—
═CH—
0

Me
—NMe—
═CH—
1

Me
—NMe—
═CH—
2

Et
—NMe—
═CH—
0

Et
—NMe—
═CH—
1

Et
—NMe—
═CH—
2

Pr
—NMe—
═CH—
0

Pr
—NMe—
═CH—
1

Pr
—NMe—
═CH—
2

iPr
—NMe—
═CH—
0

iPr
—NMe—
═CH—
1

iPr
—NMe—
═CH—
2

TABLE 3

R¹
A¹
A³
n

tBu
—NMe—
═CH—
0

tBu
—NMe—
═CH—
1

tBu
—NMe—
═CH—
2

CF₃
—NMe—
═CH—
0

CF₃
—NMe—
═CH—
1

CF₃
—NMe—
═CH—
2

CH₂CF₃
—NMe—
═CH—
0

CH₂CF₃
—NMe—
═CH—
1

CH₂CF₃
—NMe—
═CH—
2

CH═CH₂
—NMe—
═CH—
0

CH═CH₂
—NMe—
═CH—
1

CH═CH₂
—NMe—
═CH—
2

CH₂CH═CH₂
—NMe—
═CH—
0

CH₂CH═CH₂
—NMe—
═CH—
1

CH₂CH═CH₂
—NMe—
═CH—
2

C≡CH
—NMe—
═CH—
0

C≡CH
—NMe—
═CH—
1

C≡CH
—NMe—
═CH—
2

CH₂C≡CH
—NMe—
═CH—
0

CH₂C≡CH
—NMe—
═CH—
1

CH₂C≡CH
—NMe—
═CH—
2

CyPr
—NMe—
═CH—
0

CyPr
—NMe—
═CH—
1

CyPr
—NMe—
═CH—
2

TABLE 4

R¹
A¹
A³
n

Me
—NMe—
═CBr—
0

Me
—NMe—
═CBr—
1

Me
—NMe—
═CBr—
2

Et
—NMe—
═CBr—
0

Et
—NMe—
═CBr—
1

Et
—NMe—
═CBr—
2

Pr
—NMe—
═CBr—
0

Pr
—NMe—
═CBr—
1

Pr
—NMe—
═CBr—
2

iPr
—NMe—
═CBr—
0

iPr
—NMe—
═CBr—
1

iPr
—NMe—
═CBr—
2

tBu
—NMe—
═CBr—
0

tBu
—NMe—
═CBr—
1

tBu
—NMe—
═CBr—
2

CF₃
—NMe—
═CBr—
0

CF₃
—NMe—
═CBr—
1

CF₃
—NMe—
═CBr—
2

CH₂CF₃
—NMe—
═CBr—
0

CH₂CF₃
—NMe—
═CBr—
1

CH₂CF₃
—NMe—
═CBr—
2

CH═CH₂
—NMe—
═CBr—
0

CH═CH₂
—NMe—
═CBr—
1

CH═CH₂
—NMe—
═CBr—
2

TABLE 5

R¹
A¹
A³
n

CH₂CH═CH₂
—NMe—
═CBr—
0

CH₂CH═CH₂
—NMe—
═CBr—
1

CH₂CH═CH₂
—NMe—
═CBr—
2

C≡CH
—NMe—
═CBr—
0

C≡CH
—NMe—
═CBr—
1

C≡CH
—NMe—
═CBr—
2

CH₂C≡CH
—NMe—
═CBr—
0

CH₂C≡CH
—NMe—
═CBr—
1

CH₂C≡CH
—NMe—
═CBr—
2

CyPr
—NMe—
═CBr—
0

CyPr
—NMe—
═CBr—
1

CyPr
—NMe—
═CBr—
2

Me
—N(CH₂OMe)—
═N—
0

Me
—N(CH₂OMe)—
═N—
1

Me
—N(CH₂OMe)—
═N—
2

Et
—N(CH₂OMe)—
═N—
0

Et
—N(CH₂OMe)—
═N—
1

Et
—N(CH₂OMe)—
═N—
2

Pr
—N(CH₂OMe)—
═N—
0

Pr
—N(CH₂OMe)—
═N—
1

Pr
—N(CH₂OMe)—
═N—
2

iPr
—N(CH₂OMe)—
═N—
0

iPr
—N(CH₂OMe)—
═N—
1

iPr
—N(CH₂OMe)—
═N—
2

TABLE 6

R¹
A¹
A³
n

tBu
—N(CH₂OMe)—
═N—
0

tBu
—N(CH₂OMe)—
═N—
1

tBu
—N(CH₂OMe)—
═N—
2

CF₃
—N(CH₂OMe)—
═N—
0

CF₃
—N(CH₂OMe)—
═N—
1

CF₃
—N(CH₂OMe)—
═N—
2

CH₂CF₃
—N(CH₂OMe)—
═N—
0

CH₂CF₃
—N(CH₂OMe)—
═N—
1

CH₂CF₃
—N(CH₂OMe)—
═N—
2

CH═CH₂
—N(CH₂OMe)—
═N—
0

CH═CH₂
—N(CH₂OMe)—
═N—
1

CH═CH₂
—N(CH₂OMe)—
═N—
2

CH₂CH═CH₂
—N(CH₂OMe)—
═N—
0

CH₂CH═CH₂
—N(CH₂OMe)—
═N—
1

CH₂CH═CH₂
—N(CH₂OMe)—
═N—
2

C≡CH
—N(CH₂OMe)—
═N—
0

C≡CH
—N(CH₂OMe)—
═N—
1

C≡CH
—N(CH₂OMe)—
═N—
2

CH₂C≡CH
—N(CH₂OMe)—
═N—
0

CH₂C≡CH
—N(CH₂OMe)—
═N—
1

CH₂C≡CH
—N(CH₂OMe)—
═N—
2

CyPr
—N(CH₂OMe)—
═N—
0

CyPr
—N(CH₂OMe)—
═N—
1

CyPr
—N(CH₂OMe)—
═N—
2

TABLE 7

R¹
A¹
A³
n

Me
—N(CH₂OMe)—
═CH—
0

Me
—N(CH₂OMe)—
═CH—
1

Me
—N(CH₂OMe)—
═CH—
2

Et
—N(CH₂OMe)—
═CH—
0

Et
—N(CH₂OMe)—
═CH—
1

Et
—N(CH₂OMe)—
═CH—
2

Pr
—N(CH₂OMe)—
═CH—
0

Pr
—N(CH₂OMe)—
═CH—
1

Pr
—N(CH₂OMe)—
═CH—
2

iPr
—N(CH₂OMe)—
═CH—
0

iPr
—N(CH₂OMe)—
═CH—
1

iPr
—N(CH₂OMe)—
═CH—
2

tBu
—N(CH₂OMe)—
═CH—
0

tBu
—N(CH₂OMe)—
═CH—
1

tBu
—N(CH₂OMe)—
═CH—
2

CF₃
—N(CH₂OMe)—
═CH—
0

CF₃
—N(CH₂OMe)—
═CH—
1

CF₃
—N(CH₂OMe)—
═CH—
2

CH₂CF₃
—N(CH₂OMe)—
═CH—
0

CH₂CF₃
—N(CH₂OMe)—
═CH—
1

CH₂CF₃
—N(CH₂OMe)—
═CH—
2

CH═CH₂
—N(CH₂OMe)—
═CH—
0

CH═CH₂
—N(CH₂OMe)—
═CH—
1

CH═CH₂
—N(CH₂OMe)—
═CH—
2

TABLE 8

R¹
A¹
A³
n

CH₂CH═CH₂
—N(CH₂OMe)—
═CH—
0

CH₂CH═CH₂
—N(CH₂OMe)—
═CH—
1

CH₂CH═CH₂
—N(CH₂OMe)—
═CH—
2

C≡CH
—N(CH₂OMe)—
═CH—
0

C≡CH
—N(CH₂OMe)—
═CH—
1

C≡CH
—N(CH₂OMe)—
═CH—
2

CH₂C≡CH
—N(CH₂OMe)—
═CH—
0

CH₂C≡CH
—N(CH₂OMe)—
═CH—
1

CH₂C≡CH
—N(CH₂OMe)—
═CH—
2

CyPr
—N(CH₂OMe)—
═CH—
0

CyPr
—N(CH₂OMe)—
═CH—
1

CyPr
—N(CH₂OMe)—
═CH—
2

Me
—N(CH₂OMe)—
═CBr—
0

Me
—N(CH₂OMe)—
═CBr—
1

Me
—N(CH₂OMe)—
═CBr—
2

Et
—N(CH₂OMe)—
═CBr—
0

Et
—N(CH₂OMe)—
═CBr—
1

Et
—N(CH₂OMe)—
═CBr—
2

Pr
—N(CH₂OMe)—
═CBr—
0

Pr
—N(CH₂OMe)—
═CBr—
1

Pr
—N(CH₂OMe)—
═CBr—
2

iPr
—N(CH₂OMe)—
═CBr—
0

iPr
—N(CH₂OMe)—
═CBr—
1

iPr
—N(CH₂OMe)—
═CBr—
2

TABLE 9

R¹
A¹
A³
n

tBu
—N(CH₂OMe)—
═CBr—
0

tBu
—N(CH₂OMe)—
═CBr—
1

tBu
—N(CH₂OMe)—
═CBr—
2

CF₃
—N(CH₂OMe)—
═CBr—
0

CF₃
—N(CH₂OMe)—
═CBr—
1

CF₃
—N(CH₂OMe)—
═CBr—
2

CH₂CF₃
—N(CH₂OMe)—
═CBr—
0

CH₂CF₃
—N(CH₂OMe)—
═CBr—
1

CH₂CF₃
—N(CH₂OMe)—
═CBr—
2

CH═CH₂
—N(CH₂OMe)—
═CBr—
0

CH═CH₂
—N(CH₂OMe)—
═CBr—
1

CH═CH₂
—N(CH₂OMe)—
═CBr—
2

CH₂CH═CH₂
—N(CH₂OMe)—
═CBr—
0

CH₂CH═CH₂
—N(CH₂OMe)—
═CBr—
1

CH₂CH═CH₂
—N(CH₂OMe)—
═CBr—
2

C≡CH
—N(CH₂OMe)—
═CBr—
0

C≡CH
—N(CH₂OMe)—
═CBr—
1

C≡CH
—N(CH₂OMe)—
═CBr—
2

CH₂C≡CH
—N(CH₂OMe)—
═CBr—
0

CH₂C≡CH
—N(CH₂OMe)—
═CBr—
1

CH₂C≡CH
—N(CH₂OMe)—
═CBr—
2

CyPr
—N(CH₂OMe)—
═CBr—
0

CyPr
—N(CH₂OMe)—
═CBr—
1

CyPr
—N(CH₂OMe)—
═CBr—
2

TABLE 10

R¹
A¹
A³
n

Me
O
═N—
0

Me
O
═N—
1

Me
O
═N—
2

Et
O
═N—
0

Et
O
═N—
1

Et
O
═N—
2

Pr
O
═N—
0

Pr
O
═N—
1

Pr
O
═N—
2

iPr
O
═N—
0

iPr
O
═N—
1

iPr
O
═N—
2

tBu
O
═N—
0

tBu
O
═N—
1

tBu
O
═N—
2

CF₃
O
═N—
0

CF₃
O
═N—
1

CF₃
0
═N—
2

CH₂CF₃
O
═N—
0

CH₂CF₃
O
═N—
1

CH₂CF₃
O
═N—
2

CH═CH₂
O
═N—
0

CH═CH₂
O
═N—
1

CH═CH₂
O
═N—
2

TABLE 11

R¹
A¹
A³
n

CH₂CH═CH₂
O
═N—
0

CH₂CH═CH₂
O
═N—
1

CH₂CH═CH₂
O
═N—
2

C≡CH
O
═N—
0

C≡CH
O
═N—
1

C≡CH
O
═N—
2

CH₂C≡CH
O
═N—
0

CH₂C≡CH
O
═N—
1

CH₂C≡CH
O
═N—
2

CyPr
O
═N—
0

CyPr
O
═N—
1

CyPr
O
═N—
2

Me
O
═CH—
0

Me
O
═CH—
1

Me
O
═CH—
2

Et
O
═CH—
0

Et
O
═CH—
1

Et
O
═CH—
2

Pr
O
═CH—
0

Pr
O
═CH—
1

Pr
O
═CH—
2

iPr
O
═CH—
0

iPr
O
═CH—
1

iPr
O
═CH—
2

TABLE 12

R¹
A¹
A³
n

tBu
O
═CH—
0

tBu
O
═CH—
1

tBu
O
═CH—
2

CF₃
O
═CH—
0

CF₃
O
═CH—
1

CF₃
O
═CH—
2

CH₂CF₃
O
═CH—
0

CH₂CF₃
O
═CH—
1

CH₂CF₃
O
═CH—
2

CH═CH₂
O
═CH—
0

CH═CH₂
O
═CH—
1

CH═CH₂
O
═CH—
2

CH₂CH═CH₂
O
═CH—
0

CH₂CH═CH₂
O
═CH—
1

CH₂CH═CH₂
O
═CH—
2

C≡CH
O
═CH—
0

C≡CH
O
═CH—
1

C≡CH
O
═CH—
2

CH₂C≡CH
O
═CH—
0

CH₂C≡CH
O
═CH—
1

CH₂C≡CH
O
═CH—
2

CyPr
O
═CH—
0

CyPr
O
═CH—
1

CyPr
O
═CH—
2

TABLE 13

R¹
A¹
A³
n

Me
O
═CBr—
0

Me
O
═CBr—
1

Me
O
═CBr—
2

Et
O
═CBr—
0

Et
O
═CBr—
1

Et
O
═CBr—
2

Pr
O
═CBr—
0

Pr
O
═CBr—
1

Pr
O
═CBr—
2

iPr
O
═CBr—
0

iPr
O
═CBr—
1

iPr
O
═CBr—
2

tBu
O
═CBr—
0

tBu
O
═CBr—
1

tBu
O
═CBr—
2

CF₃
O
═CBr—
0

CF₃
O
═CBr—
1

CF₃
O
═CBr—
2

CH₂CF₃
O
═CBr—
0

CH₂CF₃
O
═CBr—
1

CH₂CF₃
O
═CBr—
2

CH═CH₂
O
═CBr—
0

CH═CH₂
O
═CBr—
1

CH═CH₂
O
═CBr—
2

TABLE 14

R¹
A¹
A³
n

CH₂CH═CH₂
O
═CBr—
0

CH₂CH═CH₂
O
═CBr—
1

CH₂CH═CH₂
O
═CBr—
2

C≡CH
O
═CBr—
0

C≡CH
O
═CBr—
1

C≡CH
O
═CBr—
2

CH₂C≡CH
O
═CBr—
0

CH₂C≡CH
O
═CBr—
1

CH₂C≡CH
O
═CBr—
2

CyPr
O
═CBr—
0

CyPr
O
═CBr—
1

CyPr
O
═CBr—
2

TABLE 15

R¹
A¹
A³
n

Me
S
═N—
0

Me
S
═N—
1

Me
S
═N—
2

Et
S
═N—
0

Et
S
═N—
1

Et
S
═N—
2

Pr
S
═N—
0

Pr
S
═N—
1

Pr
S
═N—
2

iPr
S
═N—
0

iPr
S
═N—
1

iPr
S
═N—
2

tBu
S
═N—
0

tBu
S
═N—
1

tBu
S
═N—
2

CF₃
S
═N—
0

CF₃
S
═N—
1

CF₃
S
═N—
2

CH₂CF₃
S
═N—
0

CH₂CF₃
S
═N—
1

CH₂CF₃
S
═N—
2

CH═CH₂
S
═N—
0

CH═CH₂
S
═N—
1

CH═CH₂
S
═N—
2

TABLE 16

R¹
A¹
A³
n

CH₂CH═CH₂
S
═N—
0

CH₂CH═CH₂
S
═N—
1

CH₂CH═CH₂
S
═N—
2

C≡CH
S
═N—
0

C≡CH
S
═N—
1

C≡CH
S
═N—
2

CH₂C≡CH
S
═N—
0

CH₂C≡CH
S
═N—
1

CH₂C≡CH
S
═N—
2

CyPr
S
═N—
0

CyPr
S
═N—
1

CyPr
S
═N—
2

Me
S
═CH—
0

Me
S
═CH—
1

Me
S
═CH—
2

Et
S
═CH—
0

Et
S
═CH—
1

Et
S
═CH—
2

Pr
S
═CH—
0

Pr
S
═CH—
1

Pr
S
═CH—
2

iPr
S
═CH—
0

iPr
S
═CH—
1

iPr
S
═CH—
2

TABLE 17

R¹
A¹
A³
n

tBu
S
═CH—
0

tBu
S
═CH—
1

tBu
S
═CH—
2

CF₃
S
═CH—
0

CF₃
S
═CH—
1

CF₃
S
═CH—
2

CH₂CF₃
S
═CH—
0

CH₂CF₃
S
═CH—
1

CH₂CF₃
S
═CH—
2

CH═CH₂
S
═CH—
0

CH═CH₂
S
═CH—
1

CH═CH₂
S
═CH—
2

CH₂CH═CH₂
S
═CH—
0

CH₂CH═CH₂
S
═CH—
1

CH₂CH═CH₂
S
═CH—
2

C≡CH
S
═CH—
0

C≡CH
S
═CH—
1

C≡CH
S
═CH—
2

CH₂C≡CH
S
═CH—
0

CH₂C≡CH
S
═CH—
1

CH₂C≡CH
S
═CH—
2

CyPr
S
═CH—
0

CyPr
S
═CH—
1

CyPr
S
═CH—
2

TABLE 18

R¹
A¹
A³
n

Me
S
═CBr—
0

Me
S
═CBr—
1

Me
S
═CBr—
2

Et
S
═CBr—
0

Et
S
═CBr—
1

Et
S
═CBr—
2

Pr
S
═CBr—
0

Pr
S
═CBr—
1

Pr
S
═CBr—
2

iPr
S
═CBr—
0

iPr
S
═CBr—
1

iPr
S
═CBr—
2

tBu
S
═CBr—
0

tBu
S
═CBr—
1

tBu
S
═CBr—
2

CF₃
S
═CBr—
0

CF₃
S
═CBr—
1

CF₃
S
═CBr—
2

CH₂CF₃
S
═CBr—
0

CH₂CF₃
S
═CBr—
1

CH₂CF₃
S
═CBr—
2

CH═CH₂
S
═CBr—
0

CH═CH₂
S
═CBr—
1

CH═CH₂
S
═CBr—
2

TABLE 19

R¹
A¹
A³
n

CH₂CH═CH₂
S
═CBr—
0

CH₂CH═CH₂
S
═CBr—
1

CH₂CH═CH₂
S
═CBr—
2

C≡CH
S
═CBr—
0

C≡CH
S
═CBr—
1

C≡CH
S
═CBr—
2

CH₂C≡CH
S
═CBr—
0

CH₂C≡CH
S
═CBr—
1

CH₂C≡CH
S
═CBr—
2

CyPr
S
═CBr—
0

CyPr
S
═CBr—
1

CyPr
S
═CBr—
2

In the above Tables 1 to 19, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, and CyPr represents a cyclopropyl group.

A compound of the formula (A) wherein R²is a fluorine atom, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a fluorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁴are a hydrogen atom, R⁵is a fluorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a chlorine atom, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a chlorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁴are a hydrogen atom, R⁵is a chlorine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a methyl group, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a methyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁴are a hydrogen atom, R⁵is a methyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a trifluoromethyl group, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a trifluoromethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁴are a hydrogen atom, R⁵is a trifluoromethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a bromine atom, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a bromine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³and R⁴are a hydrogen atom, R⁵is a bromine atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a pentafluoroethyl group, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a pentafluoroethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³and R⁴are a hydrogen atom, R⁵is a pentafluoroethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R²is a trifluoromethoxy group, R³, R⁴, and R⁵are a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁵are a hydrogen atom, R⁴is a trifluoromethoxy group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R³, and R⁴are a hydrogen atom, R⁵is a trifluoromethoxy group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a 2-pyridyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a 3-chloro-2-pyridyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is a 2-pyrimidyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein R², R⁴, and R⁵are a hydrogen atom, R³is —SF₅, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a hydrogen atom, R⁷is a trifluoromethyl group, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a heptafluoroisopropyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a pentafluoroethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a difluoromethyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a trifluoromethoxy group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a trifluoromethylsulfanyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a trifluoromethylsulfinyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a trifluoromethylsulfonyl group, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is a bromine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is an iodine atom, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R³, R⁴, and R⁵are a hydrogen atom, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a fluorine atom, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a chlorine atom, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a bromine atom, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a methyl group, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethyl group, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a pentafluoroethyl group, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

A compound of the formula (A) wherein A²is ═CH—, R², R⁴, and R⁵are a hydrogen atom, R³is a trifluoromethoxy group, R⁶is —SF₅, R⁷is a hydrogen atom, and R¹, A¹, A³, and n are a combination shown in Tables 1-19.

Examples of pests against which the present compound has an activity include noxious arthropods such as noxious insects and noxious acarines, and nematodes. In particular, examples of the pests include the following.

Hemiptera: Delphacidae such as Laodelphax striatellus, Nilaparvata lugens, and Sogatella furcifera; Deltocephalidae such as Nephotettix cincticeps, Nephotettix virescens, and Empoasca onukii; Aphididae such as Aphis gossypii, Myzus persicae, Brevicoryne brassicae, Aphis spiraecola, Macrosiphum euphorbiae, Aulacorthum solani, Rhopalosiphum padi, Toxoptera citricidus, and Hyalopterus pruni; Pentatomidae such as Nezara antennata, Riptortus clavetus, Leptocorisa chinensis, Eysarcoris parvus, and Halyomorpha mista; Aleyrodidae such as Trialeurodes vaporariorum, Bemisia tabaci, Dialeurodes citri, and Aleurocanthus spiniferus; Coccidae such as Aonidiella aurantii, Comstockaspis perniciosa, Unaspis citri, Ceroplastes rubens, Icerya purchasi, Planococcus kraunhiae, Pseudococcus longispinis, and Pseudaulacaspis pentagona; Tingidae; Cimices such as Cimex lectularius; and Psyllidae.

Lepidoptera: Pyralidae such as Chilo suppressalis, Tryporyza incertulas, Cnaphalocrocis medinalis, Notarcha derogata, Plodia interpunctella, Ostrinia furnacalis, Hellula undalis, and Pediasia teterrellus; Noctuidae such as Spodoptera litura, Spodoptera exigua, Pseudaletia separata, Mamestra brassicae, Agrotis ipsilon, Plusia nigrisigna, Thoricoplusia spp., Heliothis spp., and Helicoverpa spp.; Pieridae such as Pieris rapae; Tortricidae such as Adoxophyes spp., Grapholita molesta, Leguminivora glycinivorella, Matsumuraeses azukivora, Adoxophyes orana fasciata, Adoxophyes honmai, Homona magnanima, Archips fuscocupreanus, and Cydia pomonella; Gracillariidae such as Caloptilia theivora and Phyllonorycter ringoneella; Carposimidae such as Carposina niponensis; Lyonetiidae such as Lyonetia spp.; Lymantriidae such as Lymantria spp. and Euproctis spp; Yponomeutidae such as Plutella xylostella; Gelechiidae such as Pectinophora gossypiella and Phthorimaea operculella; Arctiidae such as Hyphantria cunea; and Tineidae such as Tinea translucens and Tineola bisselliella.

Thysanoptera: Thripidae such as Frankliniella occidentalis, Thrips palmi, Scirtothrips dorsalis, Thrips tabaci, and Frankliniella intonsa.

Diptera: Culices such as Culex pipiens pallens, Culex tritaeniorhynchus, and Culex quinquefasciatus; Aedes spp. such as Aedes aegypti and Aedes albopictus; Anopheles spp. such as Anopheles sinensis; Chironomidae; Muscidae such as Musca domestica and Muscina stabulans; Calliphoridae; Sarcophagidae; Fanniidae; Anthomyiidae such as Delia platura and Delia antiqua; Agromyzidae such as Agromyza oryzae, Hydrellia griseola, Liriomyza sativae, Liriomyza trifolii, and Chromatomyia horticol; Chloropidae such as Chlorops oryzae; Tephritidae such as Dacus cucurbitae and Ceratitis capitata; Drosophilidae; Phoridae such as Megaselia spiracularis; Psychodidae such as Clogmia albipunctata; Simuliidae; Tabanidae such as Tabanus trigonus; and stable flies.

Coleoptera: Diabrotica spp. such as Diabrotica virgifera virgifera and Diabrotica undecimpunctata howardi; Scarabaeidae such as Anomala cuprea, Anomala rufocuprea, and Popillia japonica; weevils such as Sitophilus zeamais,

Lissorhoptrus oryzophilus, Callosobruchuys chienensis, Echinocnemus squameus, Anthonomus grandis, and Sphenophorus venatus; Tenebrionidae such as Tenebrio molitor and Tribolium castaneum; Chrysomelidae such as Oulema oryzae, Aulacophora femoralis, Phyllotreta striolata, and Leptinotarsa decemlineata; Dermestidae such as Anthrenus verbasci and Dermestes maculates; Anobiidae such as Lasioderma serricorne; Epilachna such as Epilachna vigintioctopunctata; Scolytidae such as Lyctus brunneus and Tomicus piniperda; Bostrychidae; Ptinidae; Cerambycidae such as Anoplophora malasiaca; Agriotes spp., and Paederus fuscipes.

Orthoptera: Locusta migratoria, Gryllotalpa africana, Oxya yezoensis, Oxya japonica, and Gryllidae.

Hymenoptera: Formicidae such as Monomorium pharaosis, Formica fusca japonica, Ochetellus glaber, Pristomyrmex pungens, Pheidole noda, Acromyrmex spp., and Solenopsis spp.; Vespidae; Betylidae; and Tenthredimidae such as Athalia rosae and Athalia japonica.

Nematoda: Aphelenchoides besseyi, Nothotylenchus acris, Meloidogyne incognita, Meloidogyne hapla, Meloidogyne javanica, Heterodera glycines, Globodera rostochiensis, Pratylenchus coffeae, and Pratylenchus neglectus.

Blattodea: Blattella germanica, Periplaneta fuliginosa, Periplaneta americana, Periplaneta brunnea, and Blatta orientalis.

Acarina: Tetranychidae such as Tetranychus urticae, Tetranychus kanzawai, Panonychus citri, Panonychus ulmi, and Oligonychus spp.; Eriophyidae such as Aculops pelekassi, Phyllocoptruta citri, Aculops lycopersici, Calacarus carinatus, Acaphylla theavagrans, Eriophyes chibaensis, and Aculus schlechtendali; Tarsonemidae such as Polyphagotarsonemus latus; Tenuipalpidae such as Brevipalpus phoenicis; Tuckerellidae; Ixodidae such as Haemaphysalis longicornis, Haemaphysalis flava, Dermacentor taiwanicus, Ixodes ovatus, Ixodes persulcatus, Ixodes scapularis, Boophilus microplus, and Rhipicephalus sanguineus; Acaridae such as Tyrophagus putrescentiae and Tyrophagus similis; Pyroglyphidae such as Dermatophagoides farinae and Dermatophagoides ptrenyssnus; Cheyletidae such as Cheyletus eruditus, Cheyletus malaccensis, and Cheyletus moorei; Dermanyssidae such as Ornithonyssus bacoti, Ornithonyssus sylvairum, and Dermanyssus gallinae; Trombiculidae such as Leptotrombidium akamushi; and Araneae such as Chiracanthium japonicum and Latrodectus hasseltii.

The pest controlling agent of the present invention contains the present compound and an inert carrier. Generally, the pest controlling agent of the present invention is a formulation such as an emulsion, an oil solution, a powder, a granule, a wettable powder, a flowable formulation, a microcapsule, an aerosol, a smoking agent, a poison bait, and a resin formulation which are obtained by mixing the present compound and an inert carrier such as a solid carrier, a liquid carrier and a gaseous carrier, and further adding a surfactant and other adjuvant for formulation, if necessary.

The pest controlling agent of the present invention usually contains the present compound in an amount of 0.01% to 95% by weight.

Examples of the solid carrier to be used for formulation include a fine power and a granule of clays (such as kaolin clay, diatomite, bentonite, Fubasami clay, and acid clay), synthetic hydrated silicon oxide, talc, ceramic, other inorganic minerals (such as sericite, quartz, sulfur, activated carbon, calcium carbonate, and hydrated silica), and chemical fertilizers (such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride) as well as synthetic resins (such as polypropylene, polyacrylonitrile, polyester resins such as methyl polymethacrylate and polyethylene terephthalate, nylon resins such as nylon-6, nylon-11, and nylon-66, polyamide resins, polyvinyl chloride, polyvinylidene chloride, and vinyl chloride-propylene copolymer).

Examples of the liquid carrier include water, alcohols (such as methanol, ethanol, isopropyl alcohol, butanol, hexanol, benzyl alcohol, ethylene glycol, propylene glycol, and phenoxyethanol), ketones (such as acetone, methyl ethyl ketone, and cyclohexanone), aromatic hydrocarbons (such as toluene, xylene, ethylbenzene, dodecylbenzene, phenylxylylethane, and methylnaphthalene), aliphatic hydrocarbons (such as hexane, cyclohexane, kerosine, and light oil), esters (such as ethyl acetate, butyl acetate, isopropyl mylistate, ethyl oleate, diisopropyl adipate, diisobutyl adipate, and propyleneglycol monomethyl ether acetate), nitriles (such as acetonitrile and isobutyronitrile), ethers (such as diisopropyl ether, 1,4-dioxane, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, diethylene glycol monomethyl ether, propylene glycol monomethyl ether, dipropylene glycol monomethyl ether, and 3-methoxy-3-methyl-1-butanol), acid amides (such as N,N-dimethylformamide and N,N-dimethylacetamide), halogenated hydrocarbons (such as dichloromethane, trichloroethane, and tetrachlorocarbon), sulfoxides (such as dimethylsulfoxide), propylene carbonate, and vegetable oils (such as soy bean oil and cotton seed oil).

Examples of the gaseous carrier include fluorocarbons, butane gas, liquefied petroleum gas (LPG), dimethyl ether, and carbon dioxide.

Examples of the surfactant include nonionic surfactant such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, and polyethyleneglycol fatty acid ester; and anionic surfactant such as alkylsulfonic acid salts, alkylbenzenesulfonic acid salts, and alkylsurfic acid salts.

Examples of the other adjuvant for formulation include binders, dispersants, colorants and stabilizers, and particularly for example, casein, gelatin, polysaccharides (such as starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, synthetic water-soluble polymers (such as polyvinyl alcohol, polyvinylpyrrolidone, and polyacrylic acid), PAP (acidic isopropyl phosphate), BHT (2,6-di-t-butyl-4-methylphenol), and BHA (a mixture of 2-t-butyl-4-methoxyphenol and 3-t-butyl-4-methoxyphenol).

The method for controlling pests of the present invention is applying an effective amount of the present compound to pests directly and/or habitats of pests (such as plant, soil, indoor, and in-body of animals). The present compound is usually used as the pest controlling agent of the present invention in the method for controlling pests of the present invention.

When the pest controlling agent of the present invention is used for a control of pests in agriculture, the application amount is usually 1 to 10,000 g as the present compound per 10,000 m². When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.01 to 10,000 ppm. When the pest controlling agent of the present invention is a formulation of granules or powders, they are usually applied as such.

The formulations and the dilute aqueous solutions of the formulation may be sprayed directly to the plant to be protected from pests, or may be applied to the soil to control the pests living in a soil.

Furthermore, the resin formulations of sheets or strip form can be applied by a method such as winding around plants, stretching in the vicinity of plants, and laying on the soil surface at the plant bottom.

When the pest controlling agent of the present invention is used for a control of pests in indoor, the application amount is usually 0.01 to 1,000 mg as the present compound per 1 m²in case of application for plane surface, and 0.01 to 500 mg as the present compound per 1 m³in case of application for space. When the pest controlling agent of the present invention is a formulation of emulsions, wettable powders or flowables, they are usually applied after a dilution with water to have an active ingredient concentration of 0.1 to 1,000 ppm. When the pest controlling agent of the present invention is a formulation of oil solutions, aerosols, smoking agents and poison baits, they are usually applied as such.

The pest controlling agent of the present invention could be used in farmlands on which “crops” shown below are cultivated.

Agricultural crops: corn, rice, wheat, barley, rye, oat, sorghum, cotton, soybean, peanut, sarrazin, sugar beet, rapeseed, sunflower, sugar cane, and tobacco;

Vegetables: Solanaceae vegetables (such as eggplant, tomato, green pepper, hot pepper, and potato), Cucurbitaceae vegetables (such as cucumber, pumpkin, zucchini, watermelon, and melon), Cruciferae vegetables (such as Japanese radish, turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, brown mustard, broccoli, and cauliflower), Compositae vegetables (such as burdock, garland chrysanthemum, artichoke, and lettuce), Liliaceae vegetables (such as Welsh onion, onion, garlic, and asparagus), Umbelliferae vegetables (such as carrot, parsley, celery, and parsnip), Chenopodiaceae vegetables (such as spinach, and Swiss chard), Labiatae vegetables (such as Japanese basil, mint, and basil), strawberry, sweat potato, yam, and aroid;

Fruit trees: pomaceous fruits (such as apple, common pear, Japanese pear, Chinese quince, and quince), stone fleshy fruits (such as peach, plum, nectarine, Japanese plum, cherry, apricot, and prune), citrus plants (such as Satsuma mandarin, orange, lemon, lime, and grapefruit), nuts (such as chestnut, walnut, hazel nut, almond, pistachio, cashew nut, and macadamia nut), berry fruits (such as blueberry, cranberry, blackberry, and raspberry), grape, persimmon, olive, loquat, banana, coffee, date, coconut palm, and oil palm;

Trees other fruit trees: tea, mulberry, flowering trees (such as azalea, japonica, hydrangea, sasanqua, Illicium anisatum, cherry tree, tulip poplar, crepe myetle, and orange osmanthus), street trees (such as ash tree, birch, dogwood, eucalyptus, ginkgo, lilac, maple tree, oak, poplar, cercis, Chinese sweet gum, plane tree, zelkova, Japanese arborvitae, fir tree, Japanese hemlock, needle juniper, pine, spruce, yew, elm, and horse-chestnut), sweet viburnum, Podocarpus macrophyllus, Japanese cedar, Japanese cypress, croton, spindle tree, and Chainese howthorn.

Lawn: zoysia (such as Japanese lawn grass and mascarene grass), Bermuda grass (such as Cynodon dactylon), bent grass (such as creeping bent grass, Agrostis stolonifera, and Agrostis tenuis), bluegrass (such as Kentucky bluegrass and rough bluegrass), fescue (such as tall fescue, chewing fescue, and creeping fescue), ryegrass (such as darnel and perennial ryegrass), cocksfoot, and timothy grass;

Others: flowers (such as rose, carnation, chrysanthemum, Eustoma grandiflorum Shinners, gypsophila, gerbera, pot marigold, salvia, petunia, verbena, tulip, aster, gentian, lily, pansy, cyclamen, orchid, lily of the valley, lavender, stock, ornamental kale, primula, poinsttia, gladiolus, cattleya, daisy, cymbidium, and begonia), biofuel plants (such as Jatropha, curcas, safflower, Camelina alyssum, switchgrass, miscanthus, reed canary grass, Arundo donax, kenaf, cassava, willow, and algae), and foliage plant.

The “crops” include genetically modified crops.

The pest controlling agent of the present invention can be used as a mixture with or together with other insecticides, acaricides, nematocides, fungicides, plant growth regulators, herbicides, and synergists. Examples of active ingredients of the insecticide, the acaricide, the nematocide, the fungicide, the herbicide, and the synergist are shown below.

Active Ingredients of Insecticides:

(1) Organic Phosphorus Compounds:

Acephate, Aluminium phosphide, butathiofos, cadusafos, chlorethoxyfos, chlorfenvinphos, chlorpyrifos, chlorpyrifos-methyl, cyanophos: CYAP, DCIP (diazinon, dichlorodiisopropyl ether), dichlofenthion: ECP, dichlorvos: DDVP, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, etrimfos, fenthion: MPP, fenitrothion: MEP, fosthiazate, formothion, Hydrogen phosphide, isofenphos, isoxathion, malathion, mesulfenfos, methidathion: DMTP, monocrotophos, naled: BRP, oxydeprofos: ESP, parathion, phosalone, phosmet: PMP, pirimiphos-methyl, pyridafenthion, quinalphos, phenthoate: PAP, profenofos, propaphos, prothiofos, pyraclorfos, salithion, sulprofos, tebupirimfos, temephos, tetrachlorvinphos, terbufos, thiometon, trichlorphon: DEP, vamidothion, phorate, and cadusafos.

(2) Carbamate Compounds:

Alanycarb, bendiocarb, benfuracarb, BPMC, carbaryl, carbofuran, carbosulfan, cloethocarb, ethiofencarb, fenobucarb, fenothiocarb, fenoxycarb, furathiocarb, isoprocarb: MIPC, metolcarb, methomyl, methiocarb, NAC, oxamyl, pirimicarb, propoxur: PHC, XMC, thiodicarb, xylylcarb, and aldicarb.

(3) Pyrethroid Compounds:

Acrinathrin, allethrin, benfluthrin, beta-cyfluthrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, deltamethrin, esfenvalerate, ethofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenoprox, flumethrin, fluvalinate, halfenprox, imiprothrin, permethrin, prallethrin, pyrethrins, resmethrin, sigma-cypermethrin, silafluofen, tefluthrin, tralomethrin, transfluthrin, tetramethrin, phenothrin, cyphenothrin, alpha-cypermethrin, zeta-cypermethrin, lambda-cyhalothrin, gamma-cyhalothrin, furamethrin, tau-fluvalinate, metofluthrin, profluthrin, dimefluthrin, 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, 2,3,5,6-tetrafluoro-4-methylbenzyl (EZ)-(1RS,3RS;1RS,3SR)-2,2-dimethyl-3-prop-1-enylcyclopropanecarboxylate, and 2,3,5,6-tetrafluoro-4-(methoxymethyl)benzyl (1RS,3RS;1RS,3SR)-2,2-dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylate.

(4) Nereistoxin Compounds:

Cartap, bensultap, thiocyclam, monosultap, and bisultap.

(5) Neonicotinoid Compounds:

Imidacloprid, nitenpyram, acetamiprid, thiamethoxam, thiacloprid, dinotefuran, and clothianidin.

(6) Benzoylurea Compounds:

Chlorfluazuron, bistrifluoron, diafenthiuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, and triazuron.

(7) Phenylpyrazole Compounds:

Acetoprole, ethiprole, fipronil, vaniliprole, pyriprole, and pyrafluprole.

(8) Bt Toxines:

Live spores derived from and crystal toxins produced from Bacillus thuringiesis and a mixture thereof;

(9) Hydrazine Compounds:

Chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.

(10) Organic Chlorine Compounds:

Aaldrin, dieldrin, dienochlor, endosulfan, and methoxychlor.

(11) Other Insecticidal Active Ingredients:

Mmachine oil, nicotine-sulfate; avermectin-B, bromopropylate, buprofezin, chlorphenapyr, cyantraniliprole, cyromazine, D-D (1,3-Dichloropropene), emamectin-benzoate, fenazaquin, flupyrazofos, hydroprene, methoprene, indoxacarb, metoxadiazone, milbemycin-A, pymetrozine, pyridalyl, pyriproxyfen, spinosad, sulfluramid, tolfenpyrad, triazamate, flubendiamide, lepimectin, arsenic acid, benclothiaz, calcium cyanamide, calcium polysulfide, chlordane, DDT, DSP, flufenerim, flonicamid, flurimfen, formetanate, metam-ammonium, metam-sodium, Methyl bromide, Potassium oleate, protrifenbute, spiromesifen, sulfoxaflor, sulfur, metaflumizone, spirotetramat, pyrifluquinazone, spinetoram, chlorantraniliprole, tralopyril, cyantraniliprole, a compound of the following formula (K):

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wherein:

R¹⁰⁰is chlorine, bromine, or a trifluoromethyl group,

R²⁰⁰is chlorine, bromine, or a methyl group, and

R³⁰⁰is chlorine, bromine, or a cyano group,

and a compound of the following formula (L):

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wherein:

R¹⁰⁰⁰is chlorine, bromine, or iodine.

Active Ingredients of Acardides:

Acequinocyl, amitraz, benzoximate, bifenaate, bromopropylate, chinomethionat, chlorobenzilate, CPCBS (chlorfenson), clofentezine, cyflumetofen, Kelthane (dicofol), etoxazole, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, fluproxyfen, hexythiazox, propargite: BPPS, polynactins, pyridaben, Pyrimidifen, tebufenpyrad, tetradifon, spirodiclofen, spiromesifen, spirotetramat, amidoflumet, and cyenopyrafen.

Active Ingredients of Nematocides:

DCIP, fosthiazate, levamisole hydrochloride (levamisole), methylsothiocyanate, morantel tartarate, and imicyafos.

Active Ingredients of Fungicides:

Azole fungicidal compounds such as propiconazole, prothioconazole, triadimenol, prochloraz, penconazole, tebuconazole, flusilazole, diniconazole, bromuconazole, epoxiconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, myclobutanil, fenbuconazole, hexaconazole, fluquinconazole, triticonazole, bitertanol, imazalil, and flutriafol;

Cyclic amine fungicidal compounds such as fenpropimorph, tridemorph, and fenpropidin;

Benzimidazole fungicidal compounds such as carbendezim, benomyl, thiabendazole, and thiophanate-methyl;

Procymidone; cyprodinil; pyrimethanil; diethofencarb; thiuram; fluazinam; mancozeb; iprodione; vinclozolin; chlorothalonil; captan; mepanipyrim; fenpiclonil; fludioxonil; dichlofluanid; folpet; kresoxim-methyl; azoxystrobin; trifloxystrobin; fluoxastrobin; picoxystrobin; pyraclostrobin; dimoxystrobin; pyribencarb; spiroxamine; quinoxyfen; fenhexamid; famoxadone; fenamidone; zoxamide; ethaboxam; amisulbrom; iprovalicarb; benthiavalicarb; cyazofamid; mandipropamid; boscalid; penthiopyrad; metrafenone; fluopiran; bixafen; cyflufenamid; proquinazid; isotianil, and tiadinil.

Active Ingredients of Herbicides:
(1) Phenoxyfatty Acid Herbicidal Compounds:

2,4-PA, MCP, MCPB, phenothiol, mecoprop, fluoroxypyr, triclopyr, clomeprop, and naproanilide.

(2) Benzoic Acid Herbicidal Compounds:

2,3,6-TBA, dicamba, clopyralid, picloram, aminopyralid, quinclorac, and quinmerac.

(3) Urea Herbicidal Compounds:

Diuron, linuron, chlortoluron, isoproturon, fluometuron, isouron, tebuthiuron, methabenzthiazuron, cumyluron, daimuron, and methyl-daimuron.

(4) Triazine Herbicidal Compounds:

Atrazine, ametoryn, cyanazine, simazine, propazine, simetryn, dimethametryn, prometryn, metribuzin, triaziflam, and indaziflam.

(5) Bipyridinium Herbicidal Compounds:

Paraquat and diquat.

(6) Hydroxybenzonitrile Herbicidal Compounds:

Bromoxynil and ioxynil.

(7) Dinitroaniline Herbicidal Compounds:

Pendimethalin, prodiamine, and trifluralin.

(8) Organic Phosphorus Herbicidal Compounds:

Amiprofos-methyl, butamifos, bensulide, piperophos, anilofos, glyphosate, glufosinate, glufosinate-P, and bialaphos.

(9) Carbamate Herbicidal Compounds:

Di-allate, tri-allate, EPTC, butylate, benthiocarb, esprocarb, molinate, dimepiperate, swep, chlorpropham, phenmedipham, phenisopham, pyributicarb, and asulam.

(10) Acid Amide Herbicidal Compounds:

Propanil, propyzamide, bromobutide, and etobenzanid.

(11) Chloroacetanilide Herbicidal Compounds:

Acetochlor, alachlor, butachlor, dimethenamid, propachlor, metazachlor, metolachlor, pretilachlor, thenylchlor, and pethoxamid.

(12) Diphenylether Herbicidal Compounds:

Acifluorfen-sodium, bifenox, oxyfluorfen, lactofen, fomesafen, chlomethoxynil, and aclonifen.

(13) Cyclic Imide Herbicidal Compounds:

Oxadiazon, cinidon-ethyl, carfentrazone-ethyl, surfentrazone, flumiclorac-pentyl, flumioxazin, pyraflufen-ethyl, oxadiargyl, pentoxazone, fluthiacet-methyl, butafenacil, benzfendizone, bencarbazone, and saflufenacil.

(14) Pyrazole Herbicidal Compounds:

Benzofenap, pyrazolate, pyrazoxyfen, topramezone, and pyrasulfotole.

(15) Triketone Herbicidal Compounds:

Isoxaflutole, benzobicyclon, sulcotrione, mesotrione, tembotrione, and tefuryltrione.

(16) Aryloxyphenoxypropionic Acid Herbicidal Compounds:

Clodinafop-propargyl, cyhalofop-butyl, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl, quizalofop-ethyl, and metamifop.

(17) Trioneoxime Herbicidal Compounds:

Alloxydim-sodium, sethoxydim, butroxydim, clethodim, cloproxydim, cycloxydim, tepraloxydim, tralkoxydim, and profoxydim.

(18) Sulfonylurea Herbicidal Compounds:

Chlorsulfuron, sulfometuron-methyl, metsulfuron-methyl, chlorimuron-ethyl, tribenuron-methyl, triasulfuron, bensulfuron-methyl, thifensulfuron-methyl, pyrazosulfuron-ethyl, primisulfuron-methyl, nicosulfuron, amidosulfuron, cinosulfuron, imazosulfuron, rimsulfuron, halosulfuron-methyl, prosulfuron, ethametsulfuron-methyl, triflusulfuron-methyl, flazasulfuron, cyclosulfamuron, flupyrsulfuron, sulfosulfuron, azimsulfuron, ethoxysulfuron, oxasulfuron, iodosulfuron-methyl-sodium, foramsulfuron, mesosulfuron-methyl, trifloxysulfuron, tritosulfuron, orthosulfamuron, flucetosulfuron, and propyrisulfuron.

(19) Imidazolinone Herbicidal Compounds:

Imazamethabenz-methyl, imazamethapyr, imazamox, imazapyr, imazaquin, and imazethapyr.

(20) Sulfonamide Herbicidal Compounds:

Flumetsulam, metosulam, diclosulam, florasulam, cloransulam-methyl, penoxsulam, and pyroxsulam.

(21) Pyrimidinyloxybenzoic Acid Herbicidal Compounds:

Pyrithiobac-sodium, bispyribac-sodium, pyriminobac-methyl, pyribenzoxim, pyriftalid, and pyrimisulfan.

(22) Other Herbicidal Compounds:

Bentazon, bromacil, terbacil, chlorthiamid, isoxaben, dinoseb, amitrole, cinmethylin, tridiphane, dalapon, diflufenzopyr-sodium, dithiopyr, thiazopyr, flucarbazone-sodium, propoxycarbazone-sodium, mefenacet, flufenacet, fentrazamide, cafenstrole, indanofan, oxaziclomefone, benfuresate, ACN, pyridate, chloridazon, norflurazon, flurtamone, diflufenican, picolinafen, beflubutamid, clomazone, amicarbazone, pinoxaden, pyraclonil, pyroxasulfone, thiencarbazone-methyl, aminocyclopyrachlor, ipfencarbazone, and methiozolin.

Active Ingredients of Synergists:

Piperonyl butoxide, sesamex, sulfoxide, N-(2-ethylhexyl)-8,9,10-trinorborn-5-ene-2,3-dicarboxylmide (MGK 264), N-declyimidazole, WARF-antiresistant, TBPT, TPP, IBP, PSCP, methyl iodide (CH₃I), t-phenylbutenone, diethylmaleate, DMC, FDMC, ETP, and ETN.

EXAMPLES

The present invention is described in more detail by Production Examples, Formulation Examples, and Test Examples, but the present invention is not limited to these Examples.

First, Production Examples of the present compound are shown below.

Production Example 1

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (1.34 g), 2-methylsulfanylbenzaldehyde (1.28 g), sodium hydrogen sulfite (2.19 g), and DMF (14 ml) was stirred with heating at 80° C. for 1 hour, and then heated to 120° C., and stirred with heating for further 3 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate 3 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.74 g of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 1).

Present Compound 1

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¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.33-8.32 (1H, m), 7.58-7.53 (1H, m), 7.45-7.42 (2H, m), 7.36-7.31 (1H, m), 3.79 (3H, s), 2.44 (3H, s)

Production Example 2

To a mixture of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.32 g), methanol (4 ml) and water (6 ml), sodium periodate (0.42 g) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour, and then heated to 40° C., and stirred with heating for further 1 hour. Into the reaction mixture cooled to room temperature saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform 2 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.32 g of 2-(2-methylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 2).

Present Compound 2

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.38-8.35 (1H, m), 8.33-8.32 (1H, m), 7.89-7.84 (1H, m), 7.73-7.69 (1H, m), 7.62-7.59 (1H, m), 3.92 (3H, s), 3.03 (3H, s)

Production Example 3

To a mixture of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.30 g) and chloroform (9 ml), 69% of 3-chloroperbenzoic acid (0.70 g) was added under ice-cooling, and then heated to room temperature, and stirred for 2 hours. Then, into the mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform 2 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.32 g of 2-(2-methylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 3).

Present Compound 3

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.31-8.27 (2H, m), 7.88-7.80 (2H, m), 7.59-7.55 (1H, m), 3.72 (3H, s), 3.29 (3H, s)

Production Example 4-1

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (1.0 g), 2-ethylsulfanylbenzaldehyde (0.96 g), sodium hydrogen sulfite (1.80 g), sodium hydrogen sulfite (1.80 g) and DMF (10 ml) was stirred with heating at 160° C. for 5 hours. The reaction mixture was ice-cooled, and water was added thereto. The precipitated crystal was collected by filtration, and washed with water, then hexane. The obtained crystal was dried under reduced pressure to give 1.09 g of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 4).

Present Compound 4

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¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.33-8.31 (1H, m), 7.56-7.49 (2H, m), 7.47-7.43 (1H, m), 7.39-7.34 (1H, m), 3.77 (3H, s), 2.87 (2H, q), 1.24 (3H, t)

Alternatively, Present Compound 4 can be synthesized by the following method.

Production Example 4-2

To a mixture of N-(2-methylamino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide (6.0 g) and xylene (170 ml), p-toluenesulfonic acid monohydrate (5.47 g) was added, and stirred under reflux for 9 hours. After the reaction mixture was allowed to stand to cool to room temperature, the mixture was concentrated under reduced pressure, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 5.17 g of Present Compound 4.

Production Example 5

A mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.25 g), sodium periodate (0.24 g), methanol (6 ml), water (2 ml), and THF (0.8 ml) was stirred at room temperature for 20 minutes, and then heated to 50° C., and stirred with heating for further 1.5 hours. To the ice-cooled reaction mixture, water was added. The precipitated crystal was collected by filtration. The obtained crystal was dissolved in ethyl acetate, and washed with saturated aqueous sodium thiosulfate solution, saturated aqueous sodium hydrogen carbonate solution, then saturated brine, sequentially. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was washed with hexane to give 0.20 g of 2-(2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 5).

Present Compound 5

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.32-8.30 (1H, m), 8.27-8.24 (1H, m), 7.86-7.81 (1H, m), 7.72-7.68 (1H, m), 7.62-7.59 (1H, m), 3.89 (3H, s), 3.42-3.31 (1H, m), 3.02-2.92 (1H, m), 1.31 (3H, t)

Production Example 6

To a mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.25 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.43 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1 hour. To the reaction mixture, chloroform was added under ice-cooling, and then saturated aqueous sodium thiosulfate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, then saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The obtained crystal was washed with hexane, then methyl-tert-butyl ether to give 0.27 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 6).

Present Compound 6

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¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.29-8.27 (1H, m), 8.25-8.21 (1H, m), 7.87-7.79 (2H, m), 7.58-7.55 (1H, m), 3.72 (3H, s), 3.42 (2H, q), 1.26 (3H, t)

Production Example 7

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-propylsulfanylbenzoic acid (1.08 g), WSC (0.78 g), and pyridine (10 ml) was stirred with heating at 120° C. for 1.5 hours. To the reaction mixture, HOBt (0.74 g) was added, and stirred with heating for 1.5 hours. WSC (0.38 g) was added thereto, and stirred with heating for further 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.23 g of 3-methyl-2-(2-propylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 7).

Present Compound 7

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¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.33-8.31 (1H, m), 7.53-7.51 (2H, m), 7.46-7.43 (1H, m), 7.38-7.33 (1H, m), 3.77 (3H, s), 2.81 (2H, t), 1.65-1.54 (2H, m), 0.93 (3H, t)

Production Example 8

A mixture of 3-methyl-2-(2-propylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.22 g), sodium periodate (0.27 g), methanol (2 ml), and water (4 ml) was stirred with heating at 40° C. for 1.5 hours. To the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.17 g of 3-methyl-2-(2-propylsulfinylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 8).

Present Compound 8

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¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.31-8.27 (2H, m), 7.86-7.80 (1H, m), 7.72-7.66 (1H, m), 7.63-7.59 (1H, m), 3.90 (3H, s), 3.44-3.36 (1H, m), 2.94-2.85 (1H, m), 2.02-1.87 (1H, m), 1.85-1.72 (1H, m), 1.06 (3H, t)

Production Example 9

To a mixture of 2-(2-propylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.22 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.33 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1.5 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.24 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 9).

Present Compound 9

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¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.29-8.27 (1H, m), 8.24-8.21 (1H, m), 7.86-7.78 (2H, m), 7.58-7.54 (1H, m), 3.71 (3H, s), 3.41-3.33 (2H, m), 1.76-1.65 (2H, m), 1.00 (3H, t)

Production Example 10

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-allylsulfanylbenzoic acid (1.46 g), WSC (1.06 g), and xylene (10 ml) was stirred with heating at 145° C. for 3 hours. After the mixture was evaporated to remove xylene, acetic acid (10 ml) was added thereto, and stirred with heating at 120° C. for further 1 hour. To the reaction mixture cooled to room temperature, 5 mol/l of aqueous sodium hydroxide solution was added to neutralize, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.83 g of 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 10).

Present Compound 10

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.34-8.32 (1H, m), 7.55-7.49 (2H, m), 7.48-7.45 (1H, m), 7.42-7.36 (1H, m), 5.81-5.70 (1H, m), 5.15-5.04 (2H, m), 3.77 (3H, s), 3.49-3.45 (2H, m)

Production Example 11

The procedure was performed according to the method described in Production Example 9 using 2-(2-allylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 3-methyl-2-(2-propylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-allylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 11).

Present Compound 11

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.31-8.29 (1H, m), 8.17-8.14 (1H, m), 7.86-7.76 (2H, m), 7.58-7.55 (1H, m), 5.81-5.69 (1H, m), 5.37-5.28 (2H, m), 4.21-4.14 (2H, m), 3.72 (3H, s)

Production Example 12

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-isopropylsulfanylbenzoic acid (1.47 g), WSC (1.06 g), and pyridine (10 ml) was stirred with heating at 120° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure.

A mixture of the resulting residue and acetic acid (10 ml) was stirred with heating at 118° C. for 1.5 hours, and then acetic anhydride (10 ml) was poured thereinto, and stirred with heating at 118° C. for 1.5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with tert-butyl methyl ether. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.05 g of 2-(2-isopropylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 12).

Present Compound 12

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¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.32-8.30 (1H, m), 7.61-7.58 (1H, m), 7.56-7.51 (1H, m), 7.49-7.46 (1H, m), 7.43-7.38 (1H, m), 3.75 (3H, s), 3.38-3.27 (1H, m), 1.18 (6H, d)

Production Example 13

The procedure was performed according to the method described in Production Example 8 using 2-(2-isopropylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 3-methyl-2-(2-propylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-isopropylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 13).

Present Compound 13

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¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.31-8.30 (1H, m), 8.18-8.15 (1H, m), 7.84-7.80 (1H, m), 7.72-7.67 (1H, m), 7.62-7.59 (1H, m), 3.87 (3H, s), 3.50-3.39 (1H, m), 1.33 (3H, d), 1.09 (3H, d)

Production Example 14

The procedure was performed according to the method described in Production Example 9 using 2-(2-isopropylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 3-methyl-2-(2-propylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-isopropylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 14).

Present Compound 14

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¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.28-8.27 (1H, m), 8.22-8.19 (1H, m), 7.86-7.78 (2H, m), 7.57-7.54 (1H, m), 3.85-3.74 (1H, m), 3.71 (3H, s), 1.24 (6H, d)

Production Example 15

To a mixture of tert-butylthiol (0.67 g) and DMF (12 ml), sodium hydride (60% in oil) was added under ice-cooling. The mixture was stirred under ice-cooling for 10 minutes, and then 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.09 g) was added. The mixture was stirred at room temperature for 1 hour, and then stirred with heating at 60° C. for 1.5 hours, then at 80° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.19 g of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 15).

Present Compound 15

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¹H-NMR (CDCl₃) δ: 8.73-8.70 (1H, m), 8.31-8.29 (1H, m), 7.78-7.75 (1H, m), 7.62-7.52 (3H, m), 3.72 (3H, s), 1.12 (9H, s)

Production Examples 16 and 17

To a mixture of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.87 g) and chloroform (12 ml), 3-chloroperbenzoic acid (purity: not less than 65%) (0.95 g) was added under ice-cooling, heated to room temperature, and stirred for 2 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of 2-(2-tert-butylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 16) and 0.52 g of 2-(2-tert-butylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 17).

Present Compound 16

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.33-8.31 (1H, m), 8.19-8.15 (1H, m), 7.85-7.80 (1H, m), 7.75-7.70 (1H, m), 7.63-7.59 (1H, m), 3.84 (3H, s), 1.05 (9H, s)

Present Compound 17

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.28-8.26 (1H, m), 8.17-8.12 (1H, m), 7.86-7.80 (2H, m), 7.57-7.53 (1H, m), 3.66 (3H, s), 1.31 (9H, s)

Production Example 18

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (0.86 g), 2-trifluoromethylsulfanylbenzoic acid (1.00 g), WSC (0.76 g), and pyridine (9 ml) was stirred with heating at 120° C. for 3.5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure.

A mixture of the resulting residue, tripotassium phosphate (2.87 g), and 1-pentanol (9 ml) was stirred with heating at 135° C. for 3.5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.98 g of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfanylphenyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 18).

Present Compound 18

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.35-8.33 (1H, m), 7.98-7.93 (1H, m), 7.71-7.59 (3H, m), 3.77 (3H, s)

Production Example 19

To a mixture of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfanylphenyl)-3H-imidazo[4,5-b]pyridine (0.80 g) and chloroform (7 ml), 3-chloroperbenzoic acid (purity: not less than 65%) (0.49 g) was added under ice-cooling. The mixture was heated to room temperature, stirred for 20 minutes, and then heated to 62° C., and stirred under reflux for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.44 g of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfinylphenyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 19).

Present Compound 19

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¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.46-8.41 (1H, m), 8.36-8.33 (1H, m), 7.92-7.83 (3H, m), 4.04 (3H, s)

Production Example 20

A mixture of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfanylphenyl)-3H-imidazo[4,5-b]pyridine (0.25 g) and acetic acid (7 ml) was heated to 80° C., and 30% of an aqueous solution of hydrogen peroxide (3 ml) was added dropwise thereto. The mixture was heated to 100° C., and then stirred with heating for 5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 76 mg of 3-methyl-6-trifluoromethyl-2-(2-trifluoromethylsulfonylphenyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 20).

Present Compound 20

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.35-8.32 (2H, m), 8.05-8.01 (1H, m), 7.97-7.93 (1H, m), 7.72-7.70 (1H, m), 3.71 (3H, s)

Production Example 21

To a mixture of N²-ethyl-5-trifluoromethylpyridin-2,3-diamine (700 mg), 2-ethylsulfanylbenzoic acid (690 mg), and pyridine (20 ml), WSC (720 mg) was added at room temperature, and heated to 95° C., and then stirred with heating for 10 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure.

The resulting residue was dissolved in xylene (20 ml), and p-toluenesulfonic acid monohydrate (1.6 g) was added thereto. The mixture was heated to 170° C., and stirred with heating for 9.5 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 295 mg of 3-ethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 21).

Present Compound 21

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¹H-NMR (CDCl₃) δ: 8.70 (1H, s), 8.32 (1H, s), 7.60-7.30 (4H, m), 4.25 (2H, q), 2.89 (2H, q), 1.35-1.30 (3H, m), 1.27-1.21 (3H, m)

Production Examples 22 and 23

The procedure was performed according to the method described in Production Examples 16 and 17 using 3-ethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 140 mg of 2-(2-ethylsulfinylphenyl)-3-ethyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 22) and 60 mg of 2-(2-ethylsulfonylphenyl)-3-ethyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 23).

Present Compound 22

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¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.31 (1H, d), 8.24 (1H, dd), 7.84 (1H, dt), 7.70 (1H, dt), 7.58 (1H, dd), 4.35 (2H, q), 3.43-3.30 (1H, m), 3.06-2.94 (1H, m), 1.41 (3H, t), 1.30 (3H, t)

Present Compound 23

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¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.32 (1H, d), 7.56-7.47 (2H, m), 7.43 (1H, dd), 7.39-7.31 (1H, m), 4.25 (2H, q), 2.89 (2H, q), 1.32 (3H, t), 1.25 (3H, t)

Production Example 24

A mixture of 2-ethylsulfanyl-N-(2-propylamino-5-toluenesulfonic acid monohydrate (1.1 g), and xylene (10 ml) was stirred with heating at 160° C. for 10 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 522 mg of 2-(2-ethylsulfanylphenyl)-3-propyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 24).

Present Compound 24

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¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.31 (1H, d), 7.56-7.32 (4H, m), 4.18 (2H, t), 2.89 (2H, q), 1.78-1.73 (2H, m), 1.28-1.21 (3H, m), 0.79 (3H, t)

Production Examples 25 and 26

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-3-propyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 100 mg of 2-(2-ethylsulfinylphenyl)-3-propyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 25) and 42 mg of 2-(2-ethylsulfonylphenyl)-3-propyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 26).

Present Compound 25

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¹H-NMR (CDCl₃) δ: 8.74 (1H, d), 8.31 (1H, d), 8.24 (1H, dd), 7.84 (1H, td), 7.70 (1H, td), 7.58 (1H, dd), 4.33-4.24 (2H, m), 3.40-3.35 (1H, m), 3.03-2.98 (1H, m), 1.84-1.71 (2H, m), 1.29 (3H, t), 0.81 (3H, t)

Present Compound 26

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¹H-NMR (CDCl₃) δ: 8.65 (1H, s), 8.21-8.13 (2H, m), 7.79-7.70 (2H, m), 7.52-7.49 (1H, m), 4.12-3.92 (2H, m), 3.50-3.30 (2H, m), 1.81-1.70 (2H, m), 1.22-1.16 (3H, m), 0.84-0.76 (3H, m)

Production Example 27

The procedure was performed according to the method described in Production Example 21 using N²-isopropyl-5-trifluoromethyl-pyridin-2,3-diamine instead of N²-ethyl-5-trifluoromethyl-pyridin-2,3-diamine to give 130 mg of 2-(2-ethylsulfanylphenyl)-3-isopropyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 27).

Present Compound 27

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¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.28 (1H, d), 7.55-7.47 (2H, m), 7.39-7.31 (2H, m), 4.40-4.33 (1H, m), 2.91 (2H, q), 1.77-1.66 (6H, m), 1.25 (3H, t)

Production Examples 28 and 29

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-3-isopropyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 60 mg of 2-(2-ethylsulfinylphenyl)-3-isopropyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 28) and 55 mg of 2-(2-ethylsulfonylphenyl)-3-isopropyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 29).

Present Compound 28

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¹H-NMR (CDCl₃) δ: 8.73 (1H, d), 8.28 (1H, d), 8.22 (1H, dd), 7.83 (1H, td), 7.69 (1H, td), 7.50 (1H, dd), 4.60-4.48 (1H, m), 3.38-3.26 (1H, m), 3.05-2.95 (1H, m), 1.77-1.71 (6H, m), 1.27 (3H, t)

Present Compound 29

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¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.24-8.22 (2H, m), 7.85-7.78 (2H, m), 7.55-7.52 (1H, m), 4.33-4.26 (1H, m), 3.72-3.62 (1H, m), 3.44-3.34 (1H, m), 1.77-1.69 (6H, m), 1.28 (3H, t)

Production Example 30

The procedure was performed according to the method described in Production Example 21 using N²-cyclopropyl-5-trifluoromethyl-pyridin-2,3-diamine instead of N²-ethyl-5-trifluoromethyl-pyridin-2,3-diamine to give 280 mg of 3-cyclopropyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 30).

Present Compound 30

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¹H-NMR (CDCl₃) δ: 8.74 (1H, s), 8.31 (1H, s), 7.53-7.47 (3H, m), 7.39-7.31 (1H, m), 3.55-3.49 (1H, m), 2.90 (2H, q), 1.25 (3H, t), 1.01-0.94 (2H, m), 0.93-0.86 (2H, m)

Production Examples 31 and 32

The procedure was performed according to the method described in Production Examples 16 and 17 using 3-cyclopropyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 114 mg of 3-cyclopropyl-2-(2-ethylsulfinylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 31) and 109 mg of 3-cyclopropyl-2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 32).

Present Compound 31

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¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.29-8.26 (2H, m), 7.85-7.79 (2H, m), 7.72-7.67 (1H, m), 3.57-3.51 (1H, m), 3.49-3.39 (1H, m), 3.09-2.95 (1H, m), 1.34 (3H, t), 1.29-1.16 (1H, m), 1.09-0.92 (2H, m), 0.80-0.65 (1H, m)

Present Compound 32

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¹H-NMR (CDCl₃) δ: 8.76 (1H, s), 8.27-8.22 (2H, m), 7.87-7.78 (2H, m), 7.65 (1H, dd), 3.60 (2H, brs), 3.39-3.33 (1H, m), 1.29 (3H, t), 1.11-1.11 (2H, m), 0.93 (2H, brs).

Production Examples 33 and 34

To a mixture of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (270 mg) and DMF (10 ml), 60% of sodium hydride (in oil) (80 mg) and chloromethyl ethyl ether (118 μl) were sequentially added under ice-cooling. The mixture was heated to room temperature, and stirred for 5 hours. Into the reaction mixture, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 180 mg of 3-ethoxymethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 33) and 70 mg of 1-ethoxymethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 34)).

Present Compound 33

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¹H-NMR (CDCl₃) δ: 8.73 (1H, d), 8.35 (1H, d), 7.58-7.47 (3H, m), 7.35 (1H, td), 5.60 (2H, s), 3.50 (2H, q), 2.89 (2H, q), 1.25 (3H, t), 1.10 (3H, t)

Present Compound 34

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¹H-NMR (CDCl₃) δ: 8.90 (1H, d), 8.19 (1H, d), 7.56-7.50 (3H, m), 7.40-7.36 (1H, m), 5.45 (2H, s), 3.25 (2H, q), 2.85 (2H, q), 1.22 (3H, t), 1.04 (3H, t)

Production Examples 35 and 36

The procedure was performed according to the method described in Production Examples 16 and 17 using 3-ethoxymethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 86 mg of 2-(2-ethylsulfinylphenyl)-3-ethoxymethyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 35) and 96 mg of 2-(2-ethylsulfonylphenyl)-3-ethoxymethyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 36).

Present Compound 35

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¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.32 (1H, d), 8.29 (1H, dd), 8.04 (1H, dd), 7.82 (1H, td), 7.70 (1H, td), 5.83 (1H, d), 5.47 (1H, d), 3.80-3.70 (2H, m), 3.61-3.49 (1H, m), 3.10-3.01 (1H, m), 1.40 (3H, t), 1.25 (3H, t)

Present Compound 36

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¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.29 (1H, d), 8.21 (1H, dd), 7.86-7.78 (2H, m), 7.72 (1H, dd), 5.51 (2H, brs), 3.64 (2H, q), 3.49 (2H, q), 1.28 (3H, t), 1.17 (3H, t)

Production Example 37

To a mixture of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (98 mg) and DMF (6 ml), 60% of sodium hydride (in oil) (29 mg) and chloromethyl methyl ether (25 μl) were sequentially added under ice-cooling. The mixture was heated room temperature, and stirred for 4 hours. Then, water was poured thereinto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 72 mg of 3-methoxymethyl-2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 37).

Present Compound 37

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¹H-NMR (CDCl₃) δ: 8.74 (1H, d), 8.36 (1H, d), 7.58-7.47 (3H, m), 7.35 (1H, td), 5.55 (2H, s), 3.31 (3H, s), 2.90 (2H, q), 1.25 (3H, t)

Production Example 38

The procedure was performed according to the method described in Production Example 37 using 2-(2-ethylsulfonylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 79 mg of 2-(2-ethylsulfonylphenyl)-3-methoxymethyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 38).

Present Compound 38

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¹H-NMR (CDCl₃) δ: 8.76 (1H, d), 8.31 (1H, d), 8.21 (1H, dd), 7.87-7.78 (2H, m), 7.72 (1H, dd), 5.48 (2H, brs), 3.50 (2H, q), 3.43 (3H, s), 1.28 (3H, t)

Production Example 39

A mixture of 2-ethylsulfanyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide (1.40 g), tripotassium phosphate (1.97 g), and tert-butanol (10 ml) was stirred under reflux at 82° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.27 g of 2-(2-ethylsulfanylphenyl)-3,6-dimethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 39).

Present Compound 39

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¹H-NMR (CDCl₃) δ: 8.28-8.26 (1H, m), 7.89-7.88 (1H, m), 7.50-7.43 (3H, m), 7.35-7.30 (1H, m), 3.72 (3H, s), 2.85 (2H, q), 2.51 (3H, s), 1.22 (3H, t)

Production Examples 40 and 41

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-3,6-dimethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-ethylsulfinylphenyl)-3,6-dimethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 40) and 2-(2-ethylsulfonylphenyl)-3,6-dimethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 41).

Present Compound 40

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¹H-NMR (CDCl₃) δ: 8.32-8.31 (1H, m), 8.24-8.21 (1H, m), 7.88-7.86 (1H, m), 7.81-7.77 (1H, m), 7.69-7.64 (1H, m), 7.60-7.57 (1H, m), 3.83 (3H, s), 3.38-3.28 (1H, m), 2.97-2.87 (1H, m), 2.52 (3H, s), 1.27 (3H, t)

Present Compound 41

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¹H-NMR (CDCl₃) δ: 8.31-8.29 (1H, m), 8.23-8.20 (1H, m), 7.84-7.75 (3H, m), 7.57-7.54 (1H, m), 3.66 (3H, s), 3.45 (2H, q), 2.51 (3H, s), 1.24 (3H, t)

Production Example 42

A mixture of 5-bromo-N²-methylpyridin-2,3-diamine (0.70 g), 2-ethylsulfanylbenzoic acid (0.66 g), WSC (0.80 g), HOBt (23 mg), and pyridine (20 ml) was stirred under reflux at 120° C. for 30 minutes. After the reaction mixture was allowed to stand overnight, the mixture was stirred under reflux at 120° C. for 9.5 hours again. Into the reaction mixture cooled to room temperature, water was poured under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. A mixture of the resulting residue and acetic anhydride (7 ml) was stirred under reflux at 140° C. for 1 hour. Aqueous sodium hydroxide solution was added to the reaction mixture cooled to room temperature to neutralize, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.60 g of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 42).

Present Compound 42

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¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.22 (1H, d), 7.54-7.48 (2H, m), 7.45-7.42 (1H, m), 7.37-7.32 (1H, m), 3.71 (3H, s), 2.86 (2H, q), 1.23 (3H, t)

Production Example 43

A mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.20 g), sodium periodate (0.18 g), methanol (3 ml), water (1 ml), and THF (0.4 ml) was stirred at room temperature for 3.5 hours. Water was poured thereinto under ice-cooling, and then the precipitated solid was collected by filtration. The obtained solid was washed with water and hexane, and dried to give 0.19 g of 6-bromo-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 43).

Present Compound 43

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¹H-NMR (CDCl₃) δ: 8.52-8.51 (1H, m), 8.26-8.22 (1H, m), 8.21-8.20 (1H, m), 7.84-7.78 (1H, m), 7.71-7.65 (1H, m), 7.60-7.57 (1H, m), 3.83 (3H, s), 3.39-3.28 (1H, m), 2.99-2.88 (1H, m), 1.29 (3H, t)

Production Example 44

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.20 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%) (0.34 g) was added under ice-cooling, and then heated to room temperature, and stirred for 3.5 hours. Chloroform and saturated aqueous sodium thiosulfate solution were poured thereinto under ice-cooling, and stirred, and then, water was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting solid was washed with hexane, and dried to give 0.20 g of 6-bromo-2-(2-ethylsulfonylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 44).

Present Compound 44

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¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.23-8.20 (1H, m), 8.17 (1H, d), 7.86-7.77 (2H, m), 7.57-7.54 (1H, m), 3.66 (3H, s), 3.42 (2H, q), 1.24 (3H, t)

Production Example 45

The procedure was performed according to the method described in Production Example 21 using 5-iodo-N²-methyl-pyridin-2,3-diamine instead of N²-ethyl-5-trifluoromethyl-pyridin-2,3-diamine to give 435 mg of 2-(2-ethylsulfanylphenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 45). Present Compound 45

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¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.39 (1H, d), 7.54-7.41 (3H, m), 7.38-7.31 (1H, m), 3.71 (3H, s), 2.85 (2H, q), 1.23 (3H, t)

Production Examples 46 and 47

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 136 mg of 2-(2-ethylsulfinylphenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 46) and 107 mg of 2-(2-ethylsulfonylphenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 47).

Present Compound 46

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¹H-NMR (CDCl₃) δ: 8.63 (1H, d), 8.38 (1H, d), 8.24 (1H, dd), 7.81 (1H, td), 7.68 (1H, td), 7.59 (1H, dd), 3.83 (3H, s), 3.39-3.29 (1H, m), 2.99-2.88 (1H, m), 1.29 (3H, t)

Present Compound 47

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¹H-NMR (CDCl₃) δ: 8.63 (1H, d), 8.37 (1H, d), 8.21 (1H, dd), 7.85-7.77 (2H, m), 7.56 (1H, dd), 3.65 (3H, s), 3.41 (2H, q), 1.24 (3H, t)

Production Example 48

A mixture of zinc cyanide (0.47 g), tetrakis(triphenylphosphine)palladium (0.12 g), 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.70 g), and N-methylpyrrolidone (hereinafter referred to as NMP) (4 ml) was stirred at 90° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.59 g of 6-cyano-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 48).

Present Compound 48

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¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.35 (1H, d), 7.49-7.58 (2H, m), 7.42-7.47 (1H, m), 7.34-7.40 (1H, m), 3.77 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

Production Example 49

To a mixture of 6-cyano-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.40 g) and chloroform (5 ml), 70% of 3-chloroperbenzoic acid (0.35 g) was added under ice-cooling, and stirred at room temperature for 2 hours. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 0.40 g of 6-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 49).

Present Compound 49

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¹H-NMR (CDCl₃) δ: 8.74 (1H, d), 8.35 (1H, d), 8.26 (1H, d), 7.84 (1H, t), 7.71 (1H, t), 7.56-7.64 (1H, m), 3.89 (3H, s), 3.28-3.41 (1H, m), 2.91-3.04 (1H, m), 1.26-1.35 (3H, m)

Production Example 50

To a mixture of 6-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.25 g) and chloroform (5 ml), 70% of 3-chloroperbenzoic acid (0.35 g) was added, and stirred at 50° C. for 2 hours. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and sodium sulfite were added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.27 g of 6-cyano-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 50).

Present Compound 50

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¹H-NMR (CDCl₃) δ: 8.73 (1H, d), 8.32 (1H, d), 8.20-8.26 (1H, m), 7.80-7.89 (2H, m), 7.54-7.60 (1H, m), 3.71 (3H, s), 3.33-3.45 (2H, m), 1.25 (3H, t)

Production Example 51

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (2 g) and THF (60 ml), n-butyllithium (1.6 M in hexane) (4.3 ml) was added dropwise with cooling in dry-ice-acetone bath. The mixture was stirred for 30 minutes, and then DMF (2.2 ml) was poured. The mixture was heated to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 189 mg of 2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-carbaldehyde (hereinafter referred to as Present Compound 51).

Present Compound 51

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¹H-NMR (CDCl₃) δ: 10.20 (1H, s), 8.96 (1H, d), 8.55 (1H, d), 7.56-7.24 (4H, m), 3.79 (3H, s), 2.90-2.83 (2H, m), 1.25-1.21 (3H, m)

Production Example 52

To a mixture of 2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-carbaldehyde (122 mg) and chloroform (3 ml), bis(2-methoxyethyl)aminosulfur trifluoride (700 μl) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 3 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with chloroform and ethyl acetate, sequentially. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 49 mg of 6-difluoromethyl-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine.

Present Compound 52

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¹H-NMR (CDCl₃) δ: 8.59 (1H, s), 8.23 (1H, s), 7.56-7.43 (3H, m), 7.38-7.33 (1H, m), 6.88 (1H, t), 3.77 (3H, s), 2.87 (2H, q), 1.23 (3H, t)

Production Examples 53 and 54

The procedure was performed according to the method described in Production Examples 16 and 17 using 6-difluoromethyl-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 110 mg of 6-difluoromethyl-2-(2-ethylsulfinylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 53) and 101 mg of 6-difluoromethyl-2-(2-ethylsulfonylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 54).

Present Compound 53

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¹H-NMR (CDCl₃) δ: 8.62 (1H, s), 8.26-8.23 (2H, m), 7.83 (1H, td), 7.70 (1H, td), 7.62 (1H, dd), 6.90 (1H, t), 3.89 (3H, s), 3.42-3.32 (1H, m), 3.02-2.92 (1H, m), 1.30 (3H, t)

Present Compound 54

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¹H-NMR (CDCl₃) δ: 8.61 (1H, s), 8.24-8.19 (2H, m), 7.87-7.78 (2H, m), 7.58 (1H, dd), 6.89 (1H, t), 3.71 (3H, s), 3.43 (2H, q), 1.25 (3H, t)

Production Example 55

A mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (500 mg), NMP (24 ml), xylene (10 ml), copper iodide (1.1 g), and sodium pentafluoropropionate (1.1 g) was heated to 170° C., and stirred with heating for 3 days. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 43 mg of 2-(2-ethylsulfanylphenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 55).

Present Compound 55

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¹H-NMR (CDCl₃) δ: 8.66 (1H, d), 8.30 (1H, d), 7.56-7.49 (2H, m), 7.47-7.43 (1H, m), 7.38-7.34 (1H, m), 3.78 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

Production Example 56

A mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (0.35 g), tripotassium phosphate (0.42 g), phenylboronic acid (0.13 g), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (0.03 g), tris(dibenzylideneacetone)dipalladium(0) (0.01 g), and 1,4-dioxane (3 ml) was stirred with heating at 70° C. for 2 hours, and then heated to 90° C., and stirred with heating for further 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.37 g of 2-(2-ethylsulfanylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 56).

Present Compound 56

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¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.26 (1H, d), 7.63-7.69 (2H, m), 7.45-7.54 (5H, m), 7.38-7.43 (1H, m), 7.32-7.37 (1H, m), 3.77 (3H, s), 2.88 (2H, q), 1.25 (3H, t)

Production Example 57

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.04 g of 2-(2-ethylsulfonylphenyl)-3-methyl-6-phenyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 57).

Present Compound 57

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¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.22-8.25 (1H, m), 8.20 (1H, d), 7.77-7.86 (2H, m), 7.64-7.68 (2H, m), 7.57-7.60 (1H, m), 7.48-7.54 (2H, m), 7.38-7.44 (1H, m), 3.72 (3H, s), 3.40-3.53 (2H, m), 1.23-1.29 (3H, m)

Production Example 58

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (350 mg) and 1,4-dioxane (5 ml), 2-fluorophenylboronic acid (150 mg), tripotassium phosphate (600 mg), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (25 mg), and tris(dibenzylideneacetone)palladium(0) (14 mg) were sequentially added, heated to 80° C., and stirred with heating for 8 hours. The reaction mixture was cooled to room temperature, and then water was poured into the reaction mixture, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 349 mg of 2-(2-ethylsulfanylphenyl)-6-(2-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 58).

Present Compound 58

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¹H-NMR (CDCl₃) δ: 8.63-8.61 (1H, m), 8.27-8.25 (1H, m), 7.54-7.46 (4H, m), 7.41-7.18 (4H, m), 3.78 (3H, s), 2.88 (2H, q), 1.28-1.22 (3H, m)

Production Examples 59 and 60

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-6-(2-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 150 mg of 2-(2-ethylsulfinylphenyl)-6-(2-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 59) and 140 mg of 2-(2-ethylsulfonylphenyl)-6-(2-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 60).

Present Compound 59

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¹H-NMR (CDCl₃) δ: 8.67-8.65 (1H, m), 8.27-8.23 (2H, m), 7.81 (1H, td), 7.69 (1H, t), 7.62 (1H, dd), 7.53 (1H, td), 7.43-7.37 (1H, m), 7.31-7.21 (2H, m), 3.89 (3H, s), 3.42-3.32 (1H, m), 3.02-2.92 (1H, m), 1.29 (3H, t)

Present Compound 60

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¹H-NMR (CDCl₃) δ: 8.64 (1H, d), 8.24-8.20 (2H, m), 7.84-7.76 (2H, m), 7.60-7.57 (1H, m), 7.55-7.49 (1H, m), 7.40-7.33 (1H, m), 7.29-7.18 (2H, m), 3.72 (3H, s), 3.48 (2H, q), 1.28-1.22 (3H, m)

Production Example 61

To a mixture of 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (350 mg) and 1,4-dioxane (5 ml), 3-fluorophenylboronic acid (150 mg), sodium carbonate (320 mg), and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (22 mg) were sequentially added. The mixture was heated to 80° C., and stirred with heating for 8 hours. Into the mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 240 mg of 2-(2-ethylsulfanylphenyl)-6-(3-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 61).

Present Compound 61

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¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.29 (1H, d), 7.55-7.41 (5H, m), 7.38-7.32 (2H, m), 7.15-7.05 (1H, m), 3.77 (3H, s), 2.86 (2H, q), 1.24 (3H, t)

Production Examples 62 and 63

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-6-(3-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 120 mg of 2-(2-ethylsulfinylphenyl)-6-(3-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 62) and 34 mg of 2-(2-ethylsulfonylphenyl)-6-(3-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 63).

Present Compound 62

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¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.26 (1H, dd), 8.22 (1H, d), 7.82 (1H, td), 7.69 (1H, td), 7.62 (1H, dd), 7.51-7.42 (2H, m), 7.39-7.34 (1H, m), 7.15-7.08 (1H, m), 3.89 (3H, s), 3.43-3.33 (1H, m), 3.02-2.92 (1H, m), 1.30 (3H, t)

Present Compound 63

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¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.16 (1H, dd), 8.11 (1H, d), 7.78-7.71 (2H, m), 7.51 (1H, dd), 7.42-7.34 (2H, m), 7.28 (1H, dd), 7.06-6.99 (1H, m), 3.65 (3H, s), 3.40 (2H, q), 1.19 (3H, t)

Production Example 64

The procedure was performed according to the method described in Production Example 61 using 4-fluorophenylboronic acid instead of 3-fluorophenylboronic acid to give 140 mg of 2-(2-ethylsulfanylphenyl)-6-(4-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 64).

Present Compound 64

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¹H-NMR (CDCl₃) δ: 8.61 (1H, d), 8.22 (1H, d), 7.63-7.57 (2H, m), 7.54-7.45 (3H, m), 7.38-7.33 (1H, m), 7.23-7.16 (2H, m), 3.77 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

Production Example 65

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-6-(4-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 58 mg of 2-(2-ethylsulfonylphenyl)-6-(4-fluorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 65).

Present Compound 65

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¹H-NMR (CDCl₃) δ: 8.64 (1H, d), 8.24-8.22 (1H, m), 8.15 (1H, d), 7.86-7.78 (2H, m), 7.62-7.58 (3H, m), 7.22-7.18 (2H, m), 3.72 (3H, s), 3.47 (2H, q), 1.26 (3H, t)

Production Example 66

The procedure was performed according to the method described in Production Example 21 using N³-methyl-5-trifluoromethyl-pyridin-2,3-diamine instead of N²-ethyl-5-trifluoromethylpyridin-2,3-diamine to give 67 mg of 2-(2-ethylsulfanylphenyl)-1-methyl-6-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 66).

Present Compound 66

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¹H-NMR (CDCl₃) δ: 8.87 (1H, d), 7.99 (1H, d), 7.54-7.48 (3H, m), 7.41-7.34 (1H, m), 3.73 (3H, s), 2.84 (2H, q), 1.21 (3H, t)

Production Example 67

The procedure was performed according to the method described in Production Example 1 using N¹-methyl-4-trifluoromethylbenzene-1,2-diamine instead of N²-methyl-5-trifluoromethylpyridin-2,3-diamine to give 0.28 g of 1-methyl-2-(2-methylsulfanylphenyl)-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 67).

Present Compound 67

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¹H-NMR (CDCl₃) δ: 8.12 (1H, brs), 7.62-7.58 (1H, m), 7.55-7.48 (2H, m), 7.45-7.39 (2H, m), 7.34-7.29 (1H, m), 3.70 (3H, s), 2.41 (3H, s)

Production Example 68

A mixture of 2-ethylsulfanyl-N-(2-methylamino-5-trifluoromethylphenyl)-benzamide (1.64 g), p-toluenesulfonic acid monohydrate (1.76 g), and xylene (50 ml) was stirred under reflux at 150° C. for 1 hour. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.40 g of 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 68).

Present Compound 68

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¹H-NMR (CDCl₃) δ: 8.12-8.10 (1H, m), 7.61-7.58 (1H, m), 7.53-7.44 (4H, m), 7.38-7.32 (1H, m), 3.69 (3H, s), 2.84 (2H, q), 1.22 (3H, t)

Production Example 69

The procedure was performed according to the method described in Production Example 2 using 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.30 g of 2-(2-ethylsulfinylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 69).

Present Compound 69

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¹H-NMR (CDCl₃) δ: 8.24-8.20 (1H, m), 8.10-8.07 (1H, m), 7.83-7.78 (1H, m), 7.70-7.62 (2H, m), 7.57-7.51 (2H, m), 3.79 (3H, s), 3.36-3.26 (1H, m), 2.98-2.88 (1H, m), 1.26 (3H, t)

Production Example 70

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.24 g of 2-(2-ethylsulfonylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 70).

Present Compound 70

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¹H-NMR (CDCl₃) δ: 8.24-8.20 (1H, m), 8.07-8.05 (1H, m), 7.84-7.77 (2H, m), 7.64-7.61 (1H, m), 7.57-7.54 (1H, m), 7.53-7.49 (1H, m), 3.63 (3H, s), 3.46-3.34 (2H, m), 1.23 (3H, t)

Production Example 71

To a mixture of 3-chloro-N²-methyl-5-trifluoromethylbenzene-1,2-diamine (1.12 g) and THF (5 ml), 2-ethylsulfanylbenzoic acid hydrochloride (1.00 g) was added under ice-cooling, heated to room temperature, and stirred for 1 hour. Sodium hydrogen carbonate (0.46 g) was added thereto, and then the reaction mixture was allowed to stand overnight. The reaction mixture was heated to 66° C., and stirred under reflux for 1.5 hours. After the mixture was cooled to room temperature, 2-ethylsulfanylbenzoic acid hydrochloride (0.5 g) was added at room temperature. After the reaction mixture was allowed to stand at room temperature overnight, sodium hydrogen carbonate (1.00 g) was added, and stirred. The reaction mixture was ice-cooled, and then water was added under ice-cooling, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.48 g of 7-chloro-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 71).

Present Compound 71

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¹H-NMR (CDCl₃) δ: 7.99-7.98 (1H, m), 7.54-7.48 (3H, m), 7.44-7.41 (1H, m), 7.37-7.32 (1H, m), 3.94 (3H, s), 2.86 (2H, q), 1.24 (3H, t)

Production Example 72

The procedure was performed according to the method described in Production Example 2 using 7-chloro-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.13 g of 7-chloro-2-(2-ethylsulfinylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 72).

Present Compound 72

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¹H-NMR (CDCl₃) δ: 8.23-8.20 (1H, m), 7.97-7.95 (1H, m), 7.85-7.80 (1H, m), 7.71-7.66 (1H, m), 7.58-7.51 (2H, m), 4.04 (3H, s), 3.32-3.21 (1H, m), 2.96-2.87 (1H, m), 1.25 (3H, t)

Production Example 73

The procedure was performed according to the method described in Production Example 3 using 7-chloro-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.16 g of 7-chloro-2-(2-ethylsulfonylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 73).

Present Compound 73

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¹H-NMR (CDCl₃) δ: 8.24-8.20 (1H, m), 7.94-7.92 (1H, m), 7.86-7.78 (2H, m), 7.58-7.52 (2H, m), 3.90 (3H, s), 3.60-3.16 (2H, m), 1.24 (3H, t)

Production Example 74

A mixture of 3-bromo-N²-methyl-5-trifluoromethylbenzene-1,2-diamine (2.22 g), 2-ethylsulfanylbenzoic acid (1.80 g), WSC (1.40 g), and pyridine (10 ml) was stirred under reflux at 115° C. for 6 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.48 g of 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 74).

Present Compound 74

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¹H-NMR (CDCl₃) δ: 8.03-8.02 (1H, m), 7.71-7.70 (1H, m), 7.54-7.47 (2H, m), 7.44-7.41 (1H, m), 7.37-7.32 (1H, m), 3.95 (3H, s), 2.86 (2H, q), 1.24 (3H, t)

Production Examples 75 and 76

The procedure was performed according to the method described in Production Examples 16 and 17 using 7-bromo-2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 7-bromo-2-(2-ethylsulfinylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 75) and 7-bromo-2-(2-ethylsulfonylphenyl)-1-methyl-5-trifluoromethyl-1H-benzimidazole (hereinafter referred to as Present Compound 76).

Present Compound 75

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¹H-NMR (CDCl₃) δ: 8.24-8.20 (1H, m), 8.03-7.99 (1H, m), 7.86-7.80 (1H, m), 7.77-7.75 (1H, m), 7.72-7.66 (1H, m), 7.56-7.52 (1H, m), 4.05 (3H, s), 3.33-3.23 (1H, m), 2.98-2.88 (1H, m), 1.26 (3H, t)

Present Compound 76

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¹H-NMR (CDCl₃) δ: 8.24-8.20 (1H, m), 7.99-7.96 (1H, m), 7.86-7.78 (2H, m), 7.75-7.73 (1H, m), 7.57-7.53 (1H, m), 3.90 (3H, s), 3.58-3.19 (2H, m), 1.25 (3H, t)

Production Example 77

To a mixture of N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanylbenzamide (0.33 g), triphenylphosphine (0.34 g), and THF (7 ml), diethyl azodicarboxylate (40% in toluene) (0.57 g) was added dropwise, and stirred at room temperature for 1.5 hours. Triphenylphosphine (79 mg) and diethyl azodicarboxylate (40% in toluene, 0.13 g) were added to the mixture, and stirred for further 1 hour. The mixture was heated to 50° C., and stirred for 1.5 hours. The reaction mixture was cooled to room temperature, and then the mixture was allowed to stand at room temperature overnight. The reaction mixture was subjected to silica gel column chromatography to give 0.28 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzoxazole (hereinafter referred to as Present Compound 77).

Present Compound 77

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¹H-NMR (CDCl₃) δ: 8.22-8.19 (1H, m), 8.17-8.15 (1H, m), 7.71-7.67 (1H, m), 7.66-7.63 (1H, m), 7.55-7.50 (1H, m), 7.41-7.37 (1H, m), 7.32-7.27 (1H, m), 2.57 (3H, s)

Production Example 78

A mixture of 2-amino-4-trifluoromethyl-phenol (0.97 g), 2-ethylsulfanylbenzoic acid (1.10 g), WSC (1.27 g), HOBt (37 mg), and pyridine (5 ml) was stirred under reflux at 115° C. for 2.5 hours. After the mixture was allowed to stand overnight, the mixture was stirred under reflux at 115° C. for 6 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine, sequentially, dried over sodium sulfate, and concentrated under reduced pressure.

A mixture of the resulting residue, p-toluenesulfonic acid monohydrate (2.09 g), and xylene (50 ml) was stirred under reflux at 153° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, 10% aqueous citric acid solution, water, saturated aqueous sodium hydrogen carbonate solution, and saturated brine, sequentially, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.98 g of 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzoxazole (hereinafter referred to as Present Compound 78).

Present Compound 78

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¹H-NMR (CDCl₃) δ: 8.19-8.15 (2H, m), 7.71-7.67 (1H, m), 7.66-7.63 (1H, m), 7.52-7.47 (1H, m), 7.45-7.42 (1H, m), 7.31-7.27 (1H, m), 3.06 (2H, q), 1.44 (3H, t)

Production Example 79

The procedure was performed according to the method described in Production Example 2 using 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzoxazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.27 g of 2-(2-ethylsulfinylphenyl)-5-trifluoromethylbenzoxazole (hereinafter referred to as Present Compound 79).

Present Compound 79

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¹H-NMR (CDCl₃) δ: 8.35-8.30 (2H, m), 8.12-8.10 (1H, m), 7.85-7.79 (1H, m), 7.75-7.66 (3H, m), 3.48-3.38 (1H, m), 3.00-2.90 (1H, m), 1.41 (3H, t)

Production Example 80

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzoxazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.24 g of 2-(2-ethylsulfonylphenyl)-5-trifluoromethylbenzoxazole (hereinafter referred to as Present Compound 80).

Present Compound 80

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¹H-NMR (CDCl₃) δ: 8.28-8.24 (1H, m), 8.11-8.09 (1H, m), 7.99-7.95 (1H, m), 7.85-7.77 (2H, m), 7.72-7.70 (2H, m), 3.82 (2H, q), 1.40 (3H, t)

Production Example 81

A mixture of 2-ethylsulfanylphenyl-N-(2-hydroxy-5-trifluoromethylpyridin-3-yl)-benzamide (0.92 g) and phosphorous oxychloride (5 ml) was heated to 120° C., and stirred under reflux. The reaction mixture cooled to room temperature was allowed to stand overnight. The mixture was heated to 120° C. again, and stirred under reflux for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and then the precipitated solid was collected by filtration, washed with water and hexane, and dried to give 0.53 g of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyloxazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 81).

Present Compound 81

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¹H-NMR (CDCl₃) δ: 8.67 (1H, s), 8.40 (1H, s), 8.25 (1H, d), 7.53 (1H, t), 7.45 (1H, d), 7.32 (1H, t), 3.08 (2H, q), 1.45 (3H, t)

Production Example 82

The procedure was performed according to the method described in Production Example 2 using 2-(2-ethylsulfanylphenyl)-6-trifluoromethyloxazolo[5,4-b]pyridine instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.17 g of 2-(2-ethylsulfinylphenyl)-6-trifluoromethyloxazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 82).

Present Compound 82

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¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.41-8.38 (2H, m), 8.36-8.33 (1H, m), 7.90-7.84 (1H, m), 7.74-7.69 (1H, m), 3.45-3.35 (1H, m), 3.00-2.90 (1H, m), 1.40 (3H, t)

Production Example 83

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-6-trifluoromethyloxazolo[5,4-b]pyridine instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.19 g of 2-(2-ethylsulfonylphenyl)-6-trifluoromethyloxazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 83).

Present Compound 83

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¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.40-8.37 (1H, m), 8.29-8.26 (1H, m), 8.05-8.02 (1H, m), 7.89-7.81 (2H, m), 3.81 (2H, q), 1.43 (3H, t)

Production Example 84

A mixture of 2-amino-4-trifluoromethylbenzenethiol hydrochloride (0.50 g), 2-methylsulfanylbenzaldehyde (0.33 g), diisopropylethylamine (0.28 g), and DMSO (4 ml) was heated to 170-180° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.42 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 84).

Present Compound 84

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¹H-NMR (CDCl₃) δ: 8.42-8.40 (1H, m), 8.05-8.02 (1H, m), 7.92-7.89 (1H, m), 7.66-7.63 (1H, m), 7.50-7.42 (2H, m), 7.32-7.27 (1H, m), 2.51 (3H, s)

Production Example 85

The procedure was performed according to the method described in Production Example 71 using 2-amino-4-trifluoromethylbenzenethiol hydrochloride instead of 3-chloro-N²-methyl-5-trifluoromethylbenzene-1,2-diamine to give 0.50 g of 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 85).

Present Compound 85

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¹H-NMR (CDCl₃) δ: 8.41-8.39 (1H, m), 8.06-8.00 (2H, m), 7.66-7.62 (1H, m), 7.55-7.51 (1H, m), 7.48-7.42 (1H, m), 7.37-7.32 (1H, m), 2.96 (2H, q), 1.33 (3H, t)

Production Example 86

The procedure was performed according to the method described in Production Example 2 using 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzothiazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.25 g of 2-(2-ethylsulfinylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 86).

Present Compound 86

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¹H-NMR (CDCl₃) δ: 8.36-8.32 (1H, m), 8.32-8.30 (1H, m), 8.08-8.05 (1H, m), 7.97-7.94 (1H, m), 7.80-7.75 (1H, m), 7.71-7.68 (1H, m), 7.66-7.61 (1H, m), 3.56-3.45 (1H, m), 3.02-2.93 (1H, m), 1.46 (3H, t)

Production Example 87

The procedure was performed according to the method described in Production Example 3 using 2-(2-ethylsulfanylphenyl)-5-trifluoromethylbenzothiazole instead of 3-methyl-2-(2-methylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.30 g of 2-(2-ethylsulfonylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 87).

Present Compound 87

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¹H-NMR (CDCl₃) δ: 8.33-8.31 (1H, m), 8.26-8.23 (1H, m), 8.10-8.06 (1H, m), 7.81-7.69 (4H, m), 3.75 (2H, q), 1.36 (3H, t)

Production Example 88

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (1.14 g), 3-chloro-2-ethylsulfanylbenzoic acid (1.56 g), WSC (1.02 g), and pyridine (12 ml) was stirred under reflux at 115° C. for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure.

To the resulting residue, tripotassium phosphate (3.82 g) and pyridine (12 ml) were added, and stirred under reflux at 115° C. for 2.5 hours. The reaction mixture was cooled to room temperature, and then the solvent was evaporated. Tripotassium phosphate (3.82 g) and DMSO (12 ml) were added to the resulting residue, and stirred with heating at 150° C. for 1 hour. The mixture was heated to 165° C., and stirred with heating for further 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.96 g of 2-(3-chloro-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 88).

Present Compound 88

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¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.32-8.30 (1H, m), 7.71 (1H, dd), 7.48-7.42 (2H, m), 3.73 (3H, s), 2.73 (2H, q), 1.05 (3H, t)

Production Example 89

To a mixture of 2-(3-chloro-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.72 g) and chloroform (10 ml), 3-chloroperbenzoic acid (purity: 69-75%, 0.66 g) was added under ice-cooling, and then heated to room temperature, and stirred for 20 minutes. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform 2 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.67 g of 2-(3-chloro-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 89).

Present Compound 89

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¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.25 (1H, d), 7.64 (1H, dd), 7.58 (1H, t), 7.39 (1H, dd), 3.71 (3H, s), 3.60-3.49 (1H, m), 3.33-3.23 (1H, m), 1.33 (3H, t)

Production Example 90

A mixture of 2-(3-chloro-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.48 g) and acetic acid (12 ml) was stirred with heating at 80° C., and then 30% of an aqueous solution of hydrogen peroxide (6 ml) was added dropwise. The mixture was heated to 100° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.21 g of 2-(3-chloro-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 90).

Present Compound 90

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.25 (1H, d), 7.85-7.81 (1H, m), 7.71 (1H, t), 7.46-7.43 (1H, m), 3.75 (3H, s), 3.59-3.41 (2H, m), 1.33 (3H, t)

Production Examples 91 and 92

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 27 mg of 2-(2-ethylsulfinyl-phenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 112) and 31 mg of 2-(2-ethylsulfonylphenyl)-3-methyl-6-pentafluoroethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 113).

Present Compound 112

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¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.29 (1H, d), 8.27 (1H, d), 7.84 (1H, t), 7.71 (1H, t), 7.60 (1H, d), 3.90 (3H, s), 3.43-3.33 (1H, m), 3.04-2.94 (1H, m), 1.31 (3H, t)

Present Compound 113

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¹H-NMR (CDCl₃) δ: 8.69 (1H, s), 8.25 (1H, s), 8.23-8.22 (1H, m), 7.88-7.79 (2H, m), 7.59-7.52 (1H, m), 3.72 (3H, s), 3.43 (2H, q), 1.26 (3H, t)

Production Example 93

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (1.14 g), 2-ethylsulfanyl-4-fluorobenzoic acid (1.44 g), WSC (1.02 g), and pyridine (12 ml) was stirred with heating at 120° C. for 1.5 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure.

To the resulting residue, p-toluenesulfonic acid (3.42 g), xylene (10 ml) and NMP (2 ml) were added, and stirred under reflux at 150° C. for 4.5 hours with removing water with Dean-Stark apparatus. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.05 g of 2-(2-ethylsulfanyl-4-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 116).

Present Compound 116

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¹H-NMR (CDCl₃) δ: 8.70-8.68 (1H, m), 8.31-8.28 (1H, m), 7.43-7.38 (1H, m), 7.17-7.13 (1H, m), 7.04-6.98 (1H, m), 3.75 (3H, s), 2.89 (2H, q), 1.26 (3H, t)

Production Examples 94 and 95

To a mixture of 2-(2-ethylsulfanyl-4-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.85 g) and chloroform (12 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.81) was added under ice-cooling, heated to room temperature, and stirred for 30 minutes. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of 2-(2-ethylsulfinyl-4-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 117) and 0.52 g of 2-(2-ethylsulfonyl-4-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 118).

Present Compound 117

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¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.31-8.30 (1H, m), 8.01-7.98 (1H, m), 7.65-7.61 (1H, m), 7.41-7.36 (1H, m), 3.90 (3H, s), 3.47-3.37 (1H, m), 3.04-2.94 (1H, m), 1.33 (3H, t)

Present Compound 118

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.29-8.27 (1H, m), 7.97-7.94 (1H, m), 7.60-7.51 (2H, m), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t)

Production Example 96

To a pressure-resistant reaction container, 6-bromo-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (1.74 g), copper (II) acetylacetone (0.26 g), acetylacetone (0.50 g), cesium carbonate (3.25 g), NMP (9 ml), and 28% of aqueous ammonia (4 ml) were added, and stirred at 120° C. for 6 hours. The mixture was cooled to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.20 g of 6-amino-2-(2-ethylsulfanylphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 125).

Present Compound 125

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¹H-NMR (CDCl₃) δ: 7.99 (1H, d), 7.40-7.49 (4H, m), 7.28-7.34 (1H, m), 3.61-3.70 (5H, m), 2.85 (2H, q), 1.22 (3H, t)

Production Example 97

A mixture of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (311 mg), copper iodide (1.5 g), sodium heptafluorobutyrate (1.8 g), NMP (5 ml), and xylene (25 ml) was stirred with heating at 150° C. for 12 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution and 28% aqueous ammonia were poured, and extracted with tert-butyl methyl ether. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 118 mg of 2-(2-ethylsulfanyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 128).

Present Compound 128

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¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.29 (1H, d), 7.56-7.51 (2H, m), 7.48-7.43 (1H, m), 7.38-7.34 (1H, m), 3.78 (3H, s), 2.89 (2H, q), 1.25 (3H, t)

Production Examples 98 and 99

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-ethylsulfinyl-phenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 129) and 2-(2-ethylsulfonylphenyl)-6-heptafluoropropyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 130).

Present Compound 129

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¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.29-8.24 (2H, m), 7.87-7.81 (1H, m), 7.74-7.68 (1H, m), 7.61 (1H, dd), 3.91 (3H, s), 3.43-3.32 (1H, m), 3.05-2.94 (1H, m), 1.31 (3H, t)

Present Compound 130

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¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.26-8.22 (2H, m), 7.87-7.81 (2H, m), 7.59-7.55 (1H, m), 3.73 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

Production Example 100

To a mixture of 2-(4-chloro-2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.83 g) and DMF (5 ml), a suspension of sodium ethylmercaptide (80%, 0.26 g) was added dropwise in DMF under ice-cooling, and stirred for 1 hour under ice-cooling. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured under ice-cooling, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography. 0.20 g of the resulting product was subjected to recycle preparation liquid chromatography to give 0.12 g of 2-(2-ethylsulfanyl-4-chlorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 133).

Present Compound 133

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.33-8.31 (1H, m), 7.44 (1H, d), 7.38 (1H, d), 7.34-7.30 (1H, m), 3.77 (3H, s), 2.91 (2H, q), 1.27 (3H, t)

Production Examples 101 and 102

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanyl-4-chlorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.34 g of 2-(2-ethylsulfinyl-4-chlorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 134) and 0.17 g of 2-(2-ethylsulfanyl-4-chlorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 135).

Present Compound 134

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¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.32-8.30 (1H, m), 8.25 (1H, d), 7.68-7.65 (1H, m), 7.56 (1H, d), 3.91 (3H, s), 3.49-3.39 (1H, m), 3.05-2.95 (1H, m), 1.35 (3H, t)

Present Compound 135

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.29-8.27 (1H, m), 8.23-8.21 (1H, m), 7.83-7.80 (1H, m), 7.51 (1H, d), 3.72 (3H, s), 3.45 (2H, q), 1.28 (3H, t)

Production Example 103

To a mixture of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine (430 mg), copper iodide (229 mg), and DMF (3 ml), sodium sulfide nonahydrate (721 mg) was added at room temperature. The mixture was stirred with heating at 110° C. for 6 hours. Into the reaction mixture cooled to room temperature, saturated aqueous ammonium chloride water solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 85 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol (hereinafter referred to as Present Compound 145):

Present Compound 145

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¹H-NMR (CDCl₃) δ: 8.41 (1H, d), 8.11 (1H, d), 7.53-7.47 (2H, m), 7.46-7.42 (1H, m), 7.37-7.31 (1H, m), 3.71 (3H, s), 3.56 (1H, s), 2.85 (2H, q), 1.22 (3H, t);

and 98 mg of a compound of the following formula (hereinafter referred to as Compound (145A).

Compound (145A)

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¹H-NMR (CDCl₃) δ: 8.48 (2H, d), 8.25 (2H, d), 7.53-7.47 (4H, m), 7.47-7.43 (2H, m), 7.36-7.32 (2H, m), 3.73 (6H, s), 2.86 (4H, q), 1.23 (6H, t)

Production Example 104

To a mixture of 6-bromo-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (348 mg), [1,1-bis(diphenylphosphino)ferrocene]palladium(II) dichloride dichloromethane adduct (41 mg), and THF (5 mL), diisopropyl zinc (1 M in toluene, 2 mL) was added at room temperature. The mixture was stirred at room temperature for 4 hours, washed with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 290 mg of 2-(2-ethylsulfanyl-phenyl)-6-isopropyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 147).

Present Compound 147

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¹H-NMR (CDCl₃) δ: 8.35 (1H, s), 7.97 (1H, s), 7.51-7.42 (3H, m), 7.32-7.26 (1H, m), 3.73 (3H, s), 3.15-3.08 (1H, m), 2.83 (2H, q), 1.35 (6H, d), 1.20 (3H, t).

Production Example 105

To a mixture of copper cyanide (514 mg) and THF (20 ml), tert-butylmagnesium chloride (1 M in THF) was added with cooling at −78° C., and stirred at the temperature for hours. To the mixture, a mixture of 6-bromo-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (1 g) and THF (10 ml) was added dropwise with cooling at −78° C.

The reaction mixture was stirred for 16 hours with warming to room temperature gradually, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to 111 mg of 6-tert-butyl-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 150).

Present Compound 150

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¹H-NMR (CDCl₃) δ: 8.53 (1H, d), 8.11 (1H, d), 7.51-7.46 (2H, m), 7.45-7.40 (1H, m), 7.36-7.29 (1H, m), 3.72 (3H, s), 2.86 (2H, q), 1.45 (9H, s), 1.24 (3H, t)

Production Example 106

A mixture of N²-methyl-6-trifluoromethylpyridin-2,3-diamine (0.96 g), 2-ethylsulfanylbenzoic acid (1.01 g), WSC (1.06 g), and pyridine (5 ml) was stirred under reflux for hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the resulting residue, a mixture of tripotassium phosphate (2.65 g) and 1-propanol (10 ml) was added, and stirred under reflux for hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.98 g of 2-(2-ethylsulfanylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 151).

Present Compound 151

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¹H-NMR (CDCl₃) δ: 8.20 (1H, d), 7.67 (1H, d), 7.56-7.48 (2H, m), 7.47-7.42 (1H, m), 7.40-7.33 (1H, m), 3.78 (3H, s), 2.87 (2H, q), 1.24 (3H, t)

Production Examples 107 and 108

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.23 g of 2-(2-ethylsulfinylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 159) and 0.42 g of 2-(2-ethylsulfonylphenyl)-3-methyl-5-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 160).

Present Compound 159

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¹H-NMR (CDCl₃) δ: 8.26 (1H, dd), 8.19 (1H, dd), 7.86-7.80 (1H, m), 7.74-7.67 (2H, m), 7.60 (1H, dd), 3.90 (3H, s), 3.41-3.27 (1H, m), 3.02-2.89 (1H, m), 1.31-1.26 (3H, m)

Present Compound 160

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¹H-NMR (CDCl₃) δ: 8.25-8.21 (1H, m), 8.15 (1H, d), 7.88-7.78 (2H, m), 7.69 (1H, d), 7.59-7.54 (1H, m), 3.73 (3H, s), 3.43 (2H, q), 1.25 (3H, t)

Production Example 109

A mixture of Compound (145A) (3.3 g) and DMF (60m) was cooled to −50° C., and bubbled with trifluoroiodomethane (17 g). The mixture was kept at −50° C., and tetrakis(dimethylamino)ethylene (3.8 ml) was added dropwise. The reaction mixture was stirred for 5 hours with warming gradually. The mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 3.2 g of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 161).

Present Compound 161

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¹H-NMR (CDCl₃) δ: 8.66 (1H, d), 8.39 (1H, d), 7.57-7.49 (2H, m), 7.48-7.42 (1H, m), 7.39-7.33 (1H, m), 3.76 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

Production Example 110-a

To a mixture of 6-bromo-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (1 g) and THF (20 ml), n-butyllithium (1.5 M in hexane, 2.1 ml) was added dropwise at −78° C. The mixture was stirred at −78° C. for 30 minutes, and then methyl trifluoroacetate (577 μl) was added dropwise. The mixture was heated to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 778 mg of crude 1-[2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-2,2,2-trifluoro-ethanone (hereinafter referred to as Present Compound 91).

Present Compound 91

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Production Example 110-b

To a mixture of the crude 1-[2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-2,2,2-trifluoro-ethanone from Production Example 110-a (778 mg), methanol (5 ml), and THF (20 ml), sodium borohydride (109 mg) was added under ice-cooling. The mixture was stirred at room temperature for 12 hours, and then 1N aqueous sodium hydroxide solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 170 mg of 1-[2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-2,2,2-trifluoro-ethanol (hereinafter referred to as Present Compound 265).

Present Compound 265

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¹H-NMR (CDCl₃) δ: 8.56 (1H, s), 8.25 (1H, s), 7.58-7.35 (4H, m), 5.24 (1H, brs), 3.77 (3H, s), 2.90 (2H, q), 1.27-1.19 (3H, m)

Production Example 110-c

To a mixture of 1-[2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-2,2,2-trifluoro-ethanol (98 mg), toluene (10 ml), and pyridine (50 μl), thionyl chloride (1 ml) was added. The mixture was stirred with heating at 50° C. for 5 hours, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 66 mg of 6-(1-chloro-2,2,2-trifluoro-ethyl)-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 266).

Present Compound 266

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¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.29 (1H, d), 7.52-7.49 (2H, m), 7.44 (1H, dd), 7.37-7.33 (1H, m), 5.36 (1H, q), 3.75 (3H, s), 2.88 (2H, q), 1.24 (3H, t)

Production Example 110-d

To a mixture of 6-(1-chloro-2,2,2-trifluoro-ethyl)-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (61 mg) and methanol (5 ml), sodium borohydride (20 mg) was added under ice-cooling. The mixture was stirred at room temperature for 3 hours, and then 1N aqueous sodium hydroxide solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 40 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-(2,2,2-trifluoro-ethyl)-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 165).

Present Compound 165

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¹H-NMR (CDCl₃) δ: 8.53 (1H, s), 8.45-8.37 (1H, m), 7.78-7.31 (4H, m), 3.84 (3H, s), 3.60-3.50 (2H, m), 2.91-2.82 (2H, m), 1.23-1.16 (3H, m)

Production Example 111

A mixture of N³-methyl-6-trifluoromethylpyridin-2,3-diamine (0.38 g), 2-ethylsulfanylbenzoic acid (0.40 g), WSC (0.42 g), and pyridine (3 ml) was stirred under reflux for hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the resulting residue, tripotassium phosphate (1.06 g) and 1-propanol (4 ml) were added, and stirred under reflux for 4 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 166).

Present Compound 166

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¹H-NMR (CDCl₃) δ: 7.85 (1H, d), 7.68 (1H, d), 7.58-7.47 (3H, m), 7.43-7.33 (1H, m), 3.71 (3H, s), 2.83 (2H, q), 1.20 (3H, t)

Production Examples 112 and 113

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.23 g of 2-(2-ethylsulfinylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 167) and 0.42 g of 2-(2-ethylsulfonylphenyl)-1-methyl-5-trifluoromethyl-1H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 168).

Present Compound 167

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¹H-NMR (CDCl₃) δ: 8.25 (1H, dd), 7.91 (1H, d), 7.83 (1H, td), 7.74 (1H, d), 7.69 (1H, td), 7.56 (1H, dd), 3.83 (3H, s), 3.53-3.37 (1H, m), 3.18-3.05 (1H, m), 1.30 (3H, t)

Present Compound 168

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¹H-NMR (CDCl₃) δ: 8.26-8.19 (1H, m), 7.90-7.86 (1H, m), 7.85-7.80 (2H, m), 7.72 (1H, d), 7.59-7.53 (1H, m), 3.66 (3H, s), 3.60-3.30 (2H, m), 1.24 (3H, t)

Production Example 114

To a mixture of ethylmercaptide (80%, 0.35 g) and DMF (9 ml), a solution of 2-(2-fluoro-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.0 g) in DMF was added dropwise under ice-cooling, heated to room temperature, and stirred at room temperature for 30 minutes. To the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.10 g of 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 174).

Present Compound 174

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¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.35-8.33 (1H, m), 7.70-7.68 (1H, m), 7.62-7.56 (2H, m), 3.79 (3H, s), 2.95 (2H, q), 1.28 (3H, t)

Production Examples 115 and 116

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.51 g of 2-(2-ethylsulfinyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 175) and 0.26 g of 2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 176).

Present Compound 175

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¹H-NMR (CDCl₃) δ: 8.79-8.78 (1H, m), 8.57-8.55 (1H, m), 8.35-8.34 (1H, m), 7.97-7.94 (1H, m), 7.77 (1H, d), 3.94 (3H, s), 3.53-3.43 (1H, m), 3.07-2.98 (1H, m), 1.36 (3H, t)

Present Compound 176

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¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.51-8.49 (1H, m), 8.31-8.30 (1H, m), 8.12-8.09 (1H, m), 7.74 (1H, d), 3.74 (3H, s), 3.48 (2H, q), 1.29 (3H, t)

Production Example 117

A mixture of 3-amino-5-(trifluoromethyl)pyridin-2-thiol 0.56 g, 2-ethylsulfanylbenzoic acid (0.52 g), WSC (0.80 g), HOBt (39 mg), and pyridine (6 ml) was stirred at 60° C. for 2 hours. After the reaction mixture was allowed to stand to cool, water was poured thereinto, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

A mixture of the resulting residue, p-toluenesulfonic acid monohydrate (0.65 g), and N-methylpyrrolidinone (5 ml) was stirred with heating at 150° C. for 2 hours. After the reaction mixture was allowed to cool, water was poured thereinto, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.38 g of 2-(2-ethylsulfanylphenyl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 183).

Present Compound 183

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¹H-NMR (CDCl₃) δ: 8.86 (1H, d), 8.57 (1H, d), 8.03 (1H, dd), 7.55 (1H, dd), 7.48 (1H, td), 7.36 (1H, td), 2.98 (2H, q), 1.34 (3H, t).

Production Examples 118 and 119

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanylphenyl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 0.13 g of 2-(2-ethylsulfinylphenyl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 184) and 0.14 g of 2-(2-ethylsulfonylphenyl)-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 185).

Present Compound 184

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¹H-NMR (CDCl₃) δ: 8.90 (1H, d), 8.49 (1H, d), 8.37 (1H, dd), 7.99 (1H, dd), 7.81 (1H, td), 7.67 (1H, td), 3.52-3.42 (1H, m), 3.01-2.92 (1H, m), 1.45 (3H, t).

Present Compound 185

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¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.52 (1H, d), 8.25 (1H, dd), 7.84-7.71 (3H, m), 3.73 (2H, q), 1.37 (3H, t).

Production Example 120-1

A mixture of 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (7.83 g), sodium sulfide (6.20 g), and NMP (27 ml) was stirred with heating at 150° C. for 2 hours. Into the reaction mixture cooled to room temperature, water and 12N hydrochloric acid were poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.74 g of a compound of the following formula:

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(hereinafter referred to as Compound (186A)).

¹H-NMR (CDCl₃) δ: 8.73-8.71 (2H, m), 8.31-8.29 (2H, m), 7.77-7.73 (2H, m), 7.47-7.37 (6H, m), 3.77 (6H, s)

Production Example 120-2

To a solution of sodium hydride (60% in oil, 0.12 g) in DMF, Compound (186A) (0.80 g) of the following formula:

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was added under ice-cooling, and stirred for 10 minutes under ice-cooling. To the mixture, 2,2,2-trifluoroethyl iodide (0.65 g) was added under ice-cooling, heated to room temperature, and stirred for 15 minutes. Then, the mixture was heated to 60° C., and stirred with heating for 1 hour. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.23 g of 3-methyl-2-[2-(2,2,2-trifluoroethylsulfanylphenyl)]-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 186).

Present Compound 186

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¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.34-8.32 (1H, m), 7.77-7.74 (1H, m), 7.61-7.48 (3H, m), 3.75 (3H, s), 3.37 (2H, q)

Production Examples 121 and 122

The procedure was performed according to the method described in Production Examples 16 and 17 using 3-methyl-2-[2-(2,2,2-trifluoroethylsulfanylphenyl)]-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 73 mg of 3-methyl-2-[2-(2,2,2-trifluoroethylsulfinylphenyl)]-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 187) and 68 mg of 3-methyl-2-[2-(2,2,2-trifluoroethylsulfanylphenyl)]-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 188).

Present Compound 187

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¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.47-8.44 (1H, m), 8.29-8.26 (1H, m), 7.91-7.87 (1H, m), 7.80-7.74 (2H, m), 4.85-4.73 (1H, m), 4.03 (3H, s), 3.55-3.43 (1H, m)

Present Compound 187

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¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.35-8.31 (2H, m), 7.95-7.84 (2H, m), 7.63-7.60 (1H, m), 4.61-4.47 (2H, m), 3.75 (3H, s)

Production Examples 123 and 124

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-ethylsulfonylphenyl)-6-trifluoromethylsulfanyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 209) and 2-(2-ethylsulfinyl-phenyl)-6-trifluoromethylsulfanyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 210).

Present Compound 209

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¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.36 (1H, d), 8.21 (1H, dd), 7.87-7.77 (2H, m), 7.59 (1H, dd), 3.71 (3H, s), 3.44 (2H, q), 1.24 (3H, t)

Present Compound 210

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¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.38 (1H, d), 8.25 (1H, dd), 7.86-7.80 (1H, m), 7.72-7.67 (1H, m), 7.60 (1H, dd), 3.88 (3H, s), 3.43-3.31 (1H, m), 3.03-2.92 (1H, m), 1.31 (3H, t)

Production Examples 125 and 126

The procedure was performed according to the method described in Production Examples 16 and 17 using 2-(2-ethylsulfonylphenyl)-6-trifluoromethylsulfanyl-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-tert-butylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine to give 2-(2-ethylsulfonylphenyl)-6-trifluoromethylsulfinyl-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 214) and 2-(2-ethylsulfonylphenyl)-6-trifluoromethylsulfonyl3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 215).

Present Compound 214

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¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.55 (1H, d), 8.24 (1H, dd), 7.90-7.83 (2H, m), 7.61 (1H, dd), 3.75 (3H, s), 3.43 (2H, q), 1.26 (3H, t)

Present Compound 215

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¹H-NMR (CDCl₃) δ: 9.05 (1H, d), 8.65 (1H, d), 8.26-8.23 (1H, m), 7.90-7.85 (2H, m), 7.61-7.57 (1H, m), 3.77 (3H, s), 3.41 (2H, q), 1.27 (3H, t)

Production Example 127

To a mixture of 2-[2-fluoro-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (0.18 g) and DMF (2 ml), sodium thiomethoxide (63 mg) was added under ice-cooling, and stirred at room temperature for 4 hours. Into the reaction mixture, water was poured, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.11 g of 2-[2-ethylsulfanyl-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 267).

Present Compound 267

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¹H-NMR (CDCl₃) δ: 8.90 (1H, d), 8.61 (1H, d), 8.14 (1H, d), 7.75 (1H, s), 7.58 (1H, d), 3.04 (2H, q), 1.38 (3H, t).

Production Example 128

To a mixture of 2-[2-ethylsulfanyl-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (0.11 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%) (0.13 g) was added, and stirred at room temperature for 12 hours. The reaction mixture was diluted with chloroform, washed with 10% aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution, sequentially, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.11 g of 2-[2-ethylsulfonyl-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine (hereinafter referred to as Present Compound 251).

Present Compound 251

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¹H-NMR (CDCl₃) δ: 8.95 (1H, s), 8.55 (1H, s), 8.52 (1H, s), 8.07 (1H, d), 7.88 (1H, d), 3.77 (2H, q), 1.40 (3H, t).

Production Example 129

To a mixture of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-thiol (535 mg), iodomethane (166 μl), and ethanol (5 ml), potassium hydroxide (200 mg) was added at room temperature, and stirred for 5 hours. To the reaction mixture, saturated aqueous ammonium chloride solution was added, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 515 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-methylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 253).

Present Compound 253

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¹H-NMR (CDCl₃) δ: 8.46 (1H, d), 8.10 (1H, d), 7.52-7.42 (3H, m), 7.37-7.26 (1H, m), 3.73 (3H, s), 2.86 (2H, q), 2.54 (3H, s), 1.22 (3H, t)

Production Example 130

To a mixture of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-methylsulfanyl-3H-imidazo[4,5-b]pyridine (363 mg) and chloroform (5 ml), 69-75% of 3-chloroperbenzoic acid (1.13 g) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 5 hours, and then saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 356 mg of 2-(2-ethylsulfonylphenyl)-6-methylsulfonyl3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 254).

Present Compound 254

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¹H-NMR (CDCl₃) δ: 9.02 (1H, d), 8.58 (1H, d), 8.23 (1H, dd), 7.90-7.81 (2H, m), 7.59 (1H, dd), 3.74 (3H, s), 3.42 (2H, q), 3.19 (3H, s), 1.26 (3H, t).

Production Example 131-1

A mixture of 6-bromo-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (1.02 mg), copper iodide (280 mg), 1,10-phenanthroline (268 mg), benzyl alcohol (456 μL), cesium carbonate (1.9 g), NMP (4 mL), and xylene (20 mL) was stirred with heating at 150° C. for 8 hours. After the mixture was allowed to stand to cool to room temperature, into the mixture, 28% of aqueous ammonia and saturated aqueous sodium hydrogen carbonate solution were poured, extracted with tert-butyl methyl ether. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 402 mg of 6-benzyloxy-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Compound 268A).

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¹H-NMR (CDCl₃) δ: 8.27 (1H, d), 7.67 (1H, d), 7.45-7.33 (9H, m), 5.16 (2H, s), 3.70 (3H, s), 2.85 (2H, q), 1.22 (3H, t).

Production Example 131-2

To a mixture of 6-benzyloxy-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine 262 mg, and chloroform (3 mL), boron tribromide (1M in dichloromethane) (698 μL) was added under ice-cooling, and stirred for 3 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with chloroform then ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 168 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-ol (hereinafter, Present Compound 268).

Present Compound 268

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¹H-NMR (DMSO-D₆) δ: 9.58 (1H, brs), 8.02 (1H, d), 7.60-7.54 (2H, m), 7.47 (1H, d), 7.41 (1H, d), 7.38-7.33 (1H, m), 3.54 (3H, s), 2.94 (2H, q), 1.16 (3H, t).

Production Example 132

To a mixture of 2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-ol (579 mg), chloroform (20 mL), and acetonitrile (6 mL), 69% of 3-chloroperbenzoic acid (1.05 g) was added under ice-cooling. The mixture was heated to room temperature, stirred for 3 hours, and filtered. The resulting filtered substance was washed with chloroform to give 566 mg of 2-(2-ethylsulfonyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-ol (hereinafter, Present Compound 269).

Present Compound 269

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Production Example 133-1

To a mixture of 2-(2-ethylsulfonyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-ol (566 mg) and DMF (5 mL), 60% of sodium hydride (in oil, 129 mg) was added, and stirred with heating at 50° C. for 1 hour. After the mixture was allowed to stand to cool to room temperature, to the mixture, carbon disulfide (1.08 mL) was added, and stirred at room temperature (2.5 hours). To a mixture, iodomethane (446 μL) was added, and stirred at room temperature for 1.5 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 681 mg of S-methyl O-[2-(2-ethylsulfonyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-yl]dithiocarboxylate (hereinafter referred to as Compound 270A).

Compound 270A

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¹H-NMR (CDCl₃) δ: 8.30-8.25 (1H, m), 8.24-8.18 (1H, m), 7.85-7.76 (3H, m), 7.58-7.53 (1H, m), 3.69 (3H, brs), 3.44 (2H, q), 2.71 (3H, brs), 1.26-1.22 (3H, m).

Production Example 133-2

To a mixture of S-methyl O-[2-(2-ethylsulfonyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine-6-yl]dithiocarboxylate (371 mg) and chloroform (3 mL), HF-pyridine complex (1.25 mL) and 1,3-dibromo-5,5-dimethylhydantoin (1.58 g) were added with cooling at −55° C. The mixture was stirred for 7 hours with heating to room temperature gradually, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with chloroform. The combined organic layer was washed with aqueous sodium thiosulfate solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to reversed-phase silica gel column chromatography to give 29 mg of 6-(bromo-difluoro-methoxy)-2-(2-ethylsulfonyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 270) and 76 mg of 2-(2-ethylsulfonyl-phenyl)-3-methyl-6-trifluoromethoxy-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 271).

Present Compound 270

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¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.26-8.21 (1H, m), 7.97-7.97 (1H, m), 7.87-7.80 (2H, m), 7.56 (1H, dd), 3.70 (3H, s), 3.45 (2H, q), 1.26 (3H, t).

Present Compound 271

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¹H-NMR (CDCl₃) δ: 8.42 (1H, d), 8.22 (1H, dd), 7.94-7.94 (1H, m), 7.87-7.79 (2H, m), 7.56 (1H, dd), 3.70 (3H, s), 3.44 (2H, q), 1.25 (3H, t).

Production Example 134

The procedure was performed according to the method described in Production Example 103 using 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine instead of 2-(2-ethylsulfanyl-phenyl)-6-iodo-3-methyl-3H-imidazo[4,5-b]pyridine to give Compound 301A.

A mixture of Compound 301A (0.94 g) and DMF (13 ml) was cooled to −50° C., and bubbled with excessive amounts of CF₃I gas to dissolve the compound in DMF. To the mixture, tetrakis(dimethylamino)ethylenediamine (1.2 ml) was added dropwise at a rate that the internal temperature did not exceed −40° C. Then, the mixture was heated to −10° C. over 1 hour, and stirred at −10° C. for 1 hour. Into the reaction mixture, water was poured, heated to room temperature, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.68 g of 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 301).

Present Compound 301

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¹H-NMR (CDCl₃) δ: 8.66 (1H, d) 8.39 (1H, d), 7.67-7.64 (1H, m), 7.59-7.52 (2H, m), 3.75 (3H, s), 2.94 (2H, q), 1.27 (3H, t).

Production Example 135

To a mixture of 2-(2-ethylsulfanyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine and chloroform (5 ml), 69% of 3-chloroperbenzoic acid (1.05 g) was added under ice-cooling, and then heated to room temperature, and stirred for 1.5 hours. Then, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution was poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.20 g of 2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethylsulfanyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 306).

Present Compound 306

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¹H-NMR (CDCl₃) δ: 8.71-8.70 (1H, m), 8.50-8.49 (1H, m), 8.38-8.36 (1H, m), 8.12-8.08 (1H, m), 7.74-7.71 (1H, m), 3.72 (3H, s), 3.49 (2H, q), 1.29 (3H, t).

Production Example 136

A mixture of 2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethylsulfinyl-3H-imidazo[4,5-b]pyridine (0.26 g), sodium tungstate dihydrate (36 mg), 30% of aqueous hydrogen peroxide solution (1 ml) and acetonitrile (5 ml) was stirred under reflux for 4.5 hours. The mixture was cooled to room temperature. Into the reaction mixture, water was poured, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.24 g of 2-(2-ethylsulfonyl-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethylsulfonyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 302).

Present Compound 302

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¹H-NMR (CDCl₃) δ: 9.08-9.07 (1H, m), 8.68-8.66 (1H, m), 8.52-8.50 (1H, m), 8.16-8.12 (1H, m), 7.76-7.73 (1H, m), 3.78 (3H, s), 3.46 (2H, q), 1.30 (3H, t)

Production Example 137-1

To a mixture of 4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-benzene-1,2-diamine (552 mg), 2-ethylsulfanylbenzoic acid (401 mg), and pyridine (27 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (422 mg) and 1-hydroxybenzotriazole (27 mg) were added at room temperature. The reaction mixture was stirred at room temperature for 5 hours, diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was dissolved in a mixed solution of DMF (7.5 mL) and toluene (30 mL), and then p-toluenesulfonic acid (837 mg) was added at room temperature. The mixture was stirred with heating at 130° C. for 8 hours, and allowed to stand to cool to room temperature. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 97 mg of 2-(2-ethylsulfanyl-phenyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 346).

Present Compound 346

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¹H-NMR (CDCl₃) δ: 12.08-11.87 (1H, m), 8.31 (1H, s), 8.12-7.44 (4H, m), 7.42-7.30 (2H, m), 2.86 (2H, q), 1.22 (3H, t).

Production Example 137-2

To a mixture of 2-(2-ethylsulfanyl-phenyl)-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (97 mg) and DMF (10 mL), sodium hydride (11 mg) and iodomethane (16 μL) were added under ice-cooling. The mixture was heated to room temperature, and stirred for 5 hours. The reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 35 mg of 2-(2-ethylsulfanyl-phenyl)-1-methyl-6-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 304) and 80 mg of 2-(2-ethylsulfanyl-phenyl)-1-methyl-5-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-1H-benzimidazole (hereinafter, Present Compound 305).

Present Compound 304

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¹H-NMR (CDCl₃) δ: 7.93 (1H, d), 7.68 (1H, s), 7.55-7.44 (4H, m), 7.37-7.29 (1H, m), 3.71 (3H, s), 2.87 (2H, q), 1.24 (3H, t).

Present Compound 305

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¹H-NMR (CDCl₃) δ: 8.12 (1H, s), 7.61-7.41 (5H, m), 7.36-7.30 (1H, m), 3.68 (3H, s), 2.86 (2H, q), 1.23 (3H, t).

Production Example 138-1

To a mixture of 2-nitro-4-(pentafluorosulphur)-phenylamine (2.0 g) and DMF (15 mL), sodium hydride (313 mg) and iodomethane (447 μL) were added under ice-cooling. The mixture was heated to room temperature, and stirred for 5 hours. The reaction mixture was diluted with water, and then the precipitated powder was collected by filtration. The resulting powder was washed with hexane to give 2.0 g of methyl-(2-nitro-4-(pentafluorosulphur)-phenyl)-amine.

methyl-[2-nitro-4-(pentafluorosulphur)-phenyl]-amine

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¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.29 (1H, brs), 7.78 (1H, dd), 6.89 (1H, d), 3.10 (3H, d).

Production Example 138-2

To a mixture of methyl-[2-nitro-4-(pentafluorosulphur)-phenyl]-amine (2.0 g), acetic acid (1.9 mL), ethanol (80 mL), and water (20 mL), iron powder (1.5 g) was added with stirring with heating at 80° C. The reaction mixture was stirred with heating at 80° C. for 6 hours, and filtered through Celite®. The resulting filtrate was concentrated under reduced pressure, and diluted with 1N aqueous sodium hydroxide solution. The mixed solution was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.6 g of N¹-methyl-4-(pentafluorosulphur)-benzene-1,2-diamine (Compound (1F)-35). N¹-methyl-4-(pentafluorosulphur)-benzene-1,2-diamine

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Production Example 138-3

To a mixture of W-methyl-4-(pentafluorosulphur)-benzene-1,2-diamine (575 mg), 2-fluoro-4-trifluoromethyl-benzaldehyde (348 μL), and DMF (5 mL), sodium hydrogen sulfite (290 mg) was added at room temperature. The mixture was heated to 100° C., and stirred with heating for 10 hours. After the mixture was allowed to stand to cool to room temperature, the mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was dissolved in DMF, and then and sodium ethanethiolate (175 mg) was added at room temperature thereto. The mixture was stirred at room temperature for 8 hours, and then into the mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 537 mg of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-1-methyl-5-(pentafluorosulphur)-1H-benzimidazole (hereinafter, Present Compound 314).

Present Compound 314

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¹H-NMR (CDCl₃) δ: 8.28 (1H, d), 7.79 (1H, dd), 7.67 (1H, s), 7.57 (2H, s), 7.46 (1H, d), 3.70 (3H, s), 2.93 (2H, q), 1.27 (3H, t).

Production Example 139

To a mixture of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-1-methyl-5-(pentafluorosulphur)-1H-benzimidazole (370 mg) and chloroform (10 mL), 69-75% of 3-chloroperbenzoic acid (335 mg) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 0.5 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 115 mg of 2-(2-ethylsulfinyl-4-trifluoromethyl-phenyl)-1-methyl-5-(pentafluorosulphur)-1H-benzimidazole(hereinafter, Present Compound 315) and 244 mg of 2-(2-ethylsulfonyl-4-trifluoromethyl-phenyl)-1-methyl-5-(pentafluorosulphur)-1H-benzimidazole (hereinafter, Present Compound 316).

Present Compound 315

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¹H-NMR (CDCl₃) δ: 8.54-8.49 (1H, m), 8.26-8.21 (1H, m), 7.95-7.89 (1H, m), 7.85-7.80 (1H, m), 7.74-7.68 (1H, m), 7.52-7.47 (1H, m), 3.82 (3H, s), 3.48-3.36 (1H, m), 3.06-2.94 (1H, m), 1.35-1.27 (3H, m).

Present Compound 316

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¹H-NMR (CDCl₃) δ: 8.50-8.41 (1H, m), 8.24-8.16 (1H, m), 8.09-8.02 (1H, m), 7.83-7.65 (2H, m), 7.50-7.39 (1H, m), 3.64 (3H, s), 3.49-3.37 (2H, m), 1.30-1.24 (3H, m).

Production Example 140

A mixture of 2-ethylsulfanylbenzoic acid (1.0 g), oxalyl chloride (0.7 ml), DMF (1 drop) and chloroform (4 ml) was stirred at room temperature for 1 hour, and concentrated under reduced pressure.

A mixture of the resulting residue, 2-amino-3-chloro-5-trifluoromethylpyridine (1.08 g) and N-ethyldiisopropylamine (0.85 g) was stirred at 140° C. for 2 hours. After the reaction mixture was allowed to stand to cool, into the mixture, water was poured, and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure.

A mixture of the resulting residue, Lawesson's reagent (2.1 g), and chlorobenzene (10 ml) was refluxed for 3 hours. After the reaction mixture was allowed to stand to cool, the reaction mixture was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.14 g of 2-(2-ethylsulfanylphenyl)-6-(trifluoromethyl)thiazolo[4,5-b]pyridine (hereinafter, Present Compound 328).

Present Compound 328

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¹H-NMR (CDCl₃) δ: 9.02 (1H, d), 8.55 (1H, d), 8.35 (1H, dd), 7.60 (1H, dd), 7.49 (1H, td), 7.40 (1H, td), 2.99 (2H, q), 1.33 (3H, t).

Production Example 141

To a mixture of 2-(2-ethylsulfanylphenyl)-6-(trifluoromethyl)thiazolo[4,5-b]pyridine (0.14 g) and chloroform (3 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.21 g) was added, and stirred at room temperature for 12 hours. The reaction mixture was diluted with chloroform, washed with 10% of aqueous sodium thiosulfate solution then saturated aqueous sodium hydrogen carbonate solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 57 mg of 2-(2-ethylsulfonylphenyl)-6-(trifluoromethyl)thiazolo[4,5-b]pyridine (hereinafter, Present Compound 329).

Present Compound 329

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¹H-NMR (CDCl₃) δ: 9.04 (1H, d), 8.62 (1H, d), 8.26 (1H, dd), 7.84-7.77 (2H, m), 7.71 (1H, dd), 3.81 (2H, q), 1.36 (3H, t).

Production Example 142

To a mixture of sodium ethyl mercaptide (80%, 0.63 g) and DMF (10 ml), a solution of 2-(4-bromo-2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (2.08 g) in DMF was added dropwise under ice-cooling, then heated to room temperature, and stirred for 30 minutes. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.57 g of 2-(4-bromo-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 238).

Present Compound 238

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Production Example 143

To a mixture of 2-(4-bromo-2-ethylsulfanylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.40 g) and chloroform (5 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.29 g) was added under ice-cooling, then heated to room temperature, and stirred for 2 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.26 g of 2-(4-bromo-2-ethylsulfinylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 239) and 0.17 g of 2-(4-bromo-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 240).

Present Compound 239

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Present Compound 240

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Production Example 144

A mixture of 2-(4-bromo-2-ethylsulfonylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.20 g), 2-tributylstannylpyrimidine (0.17 g), tetrakis(triphenylphosphine)palladium (27 mg) and toluene (5 ml) was heated at reflux under nitrogen atmosphere for 5.5 hours. After the mixture was cooled to room temperature, to the mixture, 2-tributylstannylpyrimidine (0.17 g) and tetrakis(triphenylphosphine)palladium (27 mg) were added, and stirred under reflux for further 8 hours. After the mixture was cooled to room temperature, water was poured thereinto, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.20 g of 2-[2-ethylsulfonyl-4-(pyrimidine-2-yl)-phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 333).

Present Compound 333

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¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.38-8.36 (1H, m), 8.30-8.27 (1H, m), 8.00-7.95 (1H, m), 7.63-7.55 (1H, m), 7.43 (1H, d), 7.41-7.30 (2H, m), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t).

Production Example 145-1

To a mixture of 2-chloro-1,3-dinitro-5-trifluoromethyl-benzene (20 g) and DMF (30 mL), 40% of aqueous methylamine solution (15 mL) was added dropwise under ice-cooling. The mixture was stirred for 6 hours under ice-cooling, and then the reaction mixture was added to iced water. The precipitated powder was collected by filtration, and washed with water to give 20 g of (2,6-dinitro-4-trifluoromethyl-phenyl)-methyl-amine.

(2,6-dinitro-4-trifluoromethyl-phenyl)-methyl-amine

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Production Example 145-2

To a mixture of (2,6-dinitro-4-trifluoromethyl-phenyl)-methyl-amine (5.0 g), acetic acid (11 mL), ethanol (100 mL), and ice (20 g), iron powder (6.4 g) was added under ice-cooling. The reaction mixture was stirred at 0° C. for 3.5 hours, and filtered through Celite®. The resulting filtrate was concentrated under reduced pressure, and diluted with 1N aqueous sodium hydroxide solution. The solution was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 3.1 g of N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine. N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine

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Production Example 145-3

To a mixture of N′-methyl-5-trifluoromethyl-benzene-1,2,3-triamine (1.3 g), 2-ethylsulfanylbenzoic acid (1.3 g), and pyridine (12 mL), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (1.4 g) and 1-hydroxybenzotriazole (86 mg) were added at room temperature. The mixture was stirred at room temperature for 5 hours, then heated to 110° C., and stirred with heating for 8 hours. After the reaction mixture was allowed to cool to room temperature, the reaction mixture was diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 339 mg of 2-(2-ethylsulfanyl-phenyl)-3-methyl-6-trifluoromethyl-3H-benzimidazole-4-ylamine (hereinafter, Present Compound 336).

Present Compound 336

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¹H-NMR (CDCl₃) δ: 7.55 (1H, s), 7.50-7.36 (3H, m), 7.33-7.28 (1H, m), 6.77 (1H, d), 4.04 (2H, brs), 3.91 (3H, s), 2.83 (2H, q), 1.21 (3H, t).

Production Example 146

To a mixture of sodium ethyl mercaptide (80%, 0.33 g) and DMF (4 ml), a solution of 2-(2-fluoro-4-(pentafluorosulphur)phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (1.19 g) in DMF was added dropwise under ice-cooling, then heated to room temperature, and stirred at room temperature for 2 hours. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.21 g of 2-(2-ethylsulfanyl-4-(pentafluorosulphur)phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 341).

Present Compound 341

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¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.36-8.34 (1H, m), 7.81 (1H, d), 7.73 (1H, dd), 7.58-7.54 (1H, m), 3.80 (3H, s), 2.95 (2H, q), 1.29 (3H, t).

Production Example 147

To a mixture of 2-(2-ethylsulfanyl-4-(pentafluorosulphur)phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (0.90 g) and chloroform (6 ml), 3-chloroperbenzoic acid (purity: not less than 65%, 0.68 g) was added under ice-cooling, then heated to room temperature, and stirred for 1 hour. Into the reaction mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.45 g of 2-(2-ethylsulfinyl-4-(pentafluorosulphur)phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 342) and 0.44 g of 2-(2-ethylsulfonyl-4-(pentafluorosulphur)phenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 343).

Present Compound 342

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¹H-NMR (CDCl₃) δ: 8.80-8.78 (1H, m), 8.65 (1H, d), 8.35-8.34 (1H, m), 8.07 (1H, dd), 7.78-7.75 (1H, m), 3.95 (3H, s), 3.55-3.45 (1H, m), 3.10-3.00 (1H, m), 1.36 (3H, t).

Present Compound 343

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¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.61 (1H, d), 8.32-8.30 (1H, m), 8.22 (1H, dd), 7.74-7.70 (1H, m), 3.75 (3H, s), 3.50 (2H, q), 1.30 (3H, t).

Production Example 148-1

To a mixture of 5-trifluoromethyl-pyridine-2-ylamine (65 g) and chloroform (100 mL), N-bromosuccinimide (71 g) was added in 5 parts under ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour, then heated to 80° C., and stirred with heating for 30 minutes. After the mixture was allowed to cool to room temperature, into the mixture, saturated aqueous sodium thiosulfate solution and saturated aqueous sodium hydrogen carbonate solution were poured, and extracted with chloroform. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 96 g of 3-bromo-5-trifluoromethyl-pyridine-2-ylamine.

3-bromo-5-trifluoromethyl-pyridine-2-ylamine

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¹H-NMR (CDCl₃) δ: 8.27 (1H, d), 7.86 (1H, d), 5.38 (2H, brs).

Production Example 148-2

To an autoclave reactor, 3-bromo-5-trifluoromethyl-pyridine-2-ylamine (40 g), acetylacetone copper(II) (2.2 g), acetylacetone (6.6 g), cesium carbonate (59 g), and NMP (105 mL) were added, and then 28% of aqueous ammonia solution (25 mL) was added under ice-cooling. After the reactor was sealed, the mixture heated to 110° C., and stirred with heating for 12 hours. The mixture was ice-cooled to room temperature, then diluted with water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 15 g 5-trifluoromethyl-pyridine-2,3-diamine (Compound (1F)-22).

5-trifluoromethyl-pyridine-2,3-diamine

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¹H-NMR (CDCl₃) δ: 7.93 (1H, d), 7.04 (1H, d), 4.71 (2H, brs), 3.46 (2H, brs).

Production Example 148-3

To a mixture of 5-trifluoromethyl-pyridine-2,3-diamine (8.6 g), 2-formyl-5-trifluoromethylphenylethylsulfide (11 g), and DMF (67 mL), sodium hydrogen sulfite (6.1 g) was added at room temperature. After the mixture was stirred with heating at 100° C. for 3 hours, to the mixture, copper (II) chloride dihydrate (1 g) was added, and stirred at 100° C. for further 1 hour. After the reaction mixture was allowed to cool to room temperature, the reaction mixture was added to water, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give a yellow powdered solid. The solid was washed with hot hexane to give 12 g of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 344).

Present Compound 344

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¹H-NMR (CDCl₃) δ: 12.79 (1H, brs), 8.72 (1H, brs), 8.49-8.34 (2H, m), 7.79 (1H, s), 7.64 (1H, d), 3.00 (2H, q), 1.31 (3H, t).

Production Example 149

To a mixture of 2-(2-ethylsulfanyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (12 g) and chloroform (111 mL), 69-75% of 3-chloroperbenzoic acid (8.0 g) was added under ice-cooling. The mixture was heated to room temperature, and stirred for 0.5 hours. Into the mixture, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were poured, and extracted with chloroform. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 9.1 g of 2-(2-ethylsulfonyl-4-trifluoromethyl-phenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 345).

Present Compound 345

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¹H-NMR (DMSO-D₆) δ: 14.15 (1H, brs), 8.83 (1H, s), 8.58 (1H, s), 8.41 (1H, d), 8.37 (1H, s), 8.19 (1H, d), 3.97 (2H, q), 1.23 (3H, t).

Production Example 150

A mixture of N-(2-amino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide (200 mg), tert-butylalcohol (1 ml), and THF (9 ml) was stirred with heating at 80° C., then 60% of sodium hydride (in oil, 56 mg) was added thereto. The mixture was stirred with heating at 80° C. for 2 hours, and then 60% of sodium hydride (in oil, 56 mg) was added. The mixture was further stirred with heating at the same temperature for 2 hours, and then to the mixture, 60% of sodium hydride (in oil, 56 mg) was added, and stirred with heating at the same temperature for 2 hours. The reaction mixture was cooled to room temperature, and evaporated to remove the solvent, and then to the mixture, saturated ammonium chloride solution was added, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 132 mg of 2-(2-ethylsulfanylphenyl)-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (hereinafter, Present Compound 351).

Present Compound 351

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¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.51-8.48 (1H, m), 8.33 (1H, d), 7.66-7.61 (1H, m), 7.51-7.46 (2H, m), 2.93 (2H, q), 1.27 (3H, t)

The above present compounds and present compounds produced by a similar production method to those of the above present compounds are shown in the following tables.

The compound of the formula (1-2):

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wherein, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, A¹, A², A³, and n represent a combination shown in Tables 20-34.

TABLE 20

Present

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

1
Me
H
H
H
H
CF₃
H
NMe
CH
N
0

2
Me
H
H
H
H
CF₃
H
NMe
CH
N
1

3
Me
H
H
H
H
CF₃
H
NMe
CH
N
2

4
Et
H
H
H
H
CF₃
H
NMe
CH
N
0

5
Et
H
H
H
H
CF₃
H
NMe
CH
N
1

6
Et
H
H
H
H
CF₃
H
NMe
CH
N
2

7
Pr
H
H
H
H
CF₃
H
NMe
CH
N
0

8
Pr
H
H
H
H
CF₃
H
NMe
CH
N
1

9
Pr
H
H
H
H
CF₃
H
NMe
CH
N
2

10
CH₂═CHCH₂
H
H
H
H
CF₃
H
NMe
CH
N
0

11
CH₂═CHCH₂
H
H
H
H
CF₃
H
NMe
CH
N
2

12
iPr
H
H
H
H
CF₃
H
NMe
CH
N
0

13
iPr
H
H
H
H
CF₃
H
NMe
CH
N
1

14
iPr
H
H
H
H
CF₃
H
NMe
CH
N
2

15
tBu
H
H
H
H
CF₃
H
NMe
CH
N
0

16
tBu
H
H
H
H
CF₃
H
NMe
CH
N
1

17
tBu
H
H
H
H
CF₃
H
NMe
CH
N
2

18
CF₃
H
H
H
H
CF₃
H
NMe
CH
N
0

19
CF₃
H
H
H
H
CF₃
H
NMe
CH
N
1

20
CF₃
H
H
H
H
CF₃
H
NMe
CH
N
2

21
Et
H
H
H
H
CF₃
H
NEt
CH
N
0

22
Et
H
H
H
H
CF₃
H
NEt
CH
N
1

23
Et
H
H
H
H
CF₃
H
NEt
CH
N
2

24
Et
H
H
H
H
CF₃
H
NPr
CH
N
0

25
Et
H
H
H
H
CF₃
H
NPr
CH
N
1

TABLE 21

Present

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

26
Et
H
H
H
H
CF₃
H
NPr
CH
N
2

27
Et
H
H
H
H
CF₃
H
NiPr
CH
N
0

28
Et
H
H
H
H
CF₃
H
NiPr
CH
N
1

29
Et
H
H
H
H
CF₃
H
NiPr
CH
N
2

30
Et
H
H
H
H
CF₃
H
NCycPr
CH
N
0

31
Et
H
H
H
H
CF₃
H
NCycPr
CH
N
1

32
Et
H
H
H
H
CF₃
H
NCycPr
CH
N
2

33
Et
H
H
H
H
CF₃
H
NCH₂OEt
CH
N
0

34
Et
H
H
H
H
H
CF₃
NCH₂OEt
N
CH
0

35
Et
H
H
H
H
CF₃
H
NCH₂OEt
CH
N
1

36
Et
H
H
H
H
CF₃
H
NCH₂OEt
CH
N
2

37
Et
H
H
H
H
CF₃
H
NCH₂OMe
CH
N
0

38
Et
H
H
H
H
CF₃
H
NCH₂OMe
CH
N
2

39
Et
H
H
H
H
Me
H
NMe
CH
N
0

40
Et
H
H
H
H
Me
H
NMe
CH
N
1

41
Et
H
H
H
H
Me
H
NMe
CH
N
2

42
Et
H
H
H
H
Br
H
NMe
CH
N
0

43
Et
H
H
H
H
Br
H
NMe
CH
N
1

44
Et
H
H
H
H
Br
H
NMe
CH
N
2

45
Et
H
H
H
H
I
H
NMe
CH
N
0

46
Et
H
H
H
H
I
H
NMe
CH
N
1

47
Et
H
H
H
H
I
H
NMe
CH
N
2

48
Et
H
H
H
H
CN
H
NMe
CH
N
0

49
Et
H
H
H
H
CN
H
NMe
CH
N
1

50
Et
H
H
H
H
CN
H
NMe
CH
N
2

TABLE 22

Present

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

51
Et
H
H
H
H
CHO
H
NMe
CH
N
0

52
Et
H
H
H
H
CF₂H
H
NMe
CH
N
0

53
Et
H
H
H
H
CF₂H
H
NMe
CH
N
1

54
Et
H
H
H
H
CF₂H
H
NMe
CH
N
2

55
Et
H
H
H
H
C₂F₅
H
NMe
CH
N
0

56
Et
H
H
H
H
Ph
H
NMe
CH
N
0

57
Et
H
H
H
H
Ph
H
NMe
CH
N
2

58
Et
H
H
H
H
2-F-Ph
H
NMe
CH
N
0

59
Et
H
H
H
H
2-F-Ph
H
NMe
CH
N
1

60
Et
H
H
H
H
2-F-Ph
H
NMe
CH
N
2

61
Et
H
H
H
H
3-F-Ph
H
NMe
CH
N
0

62
Et
H
H
H
H
3-F-Ph
H
NMe
CH
N
1

63
Et
H
H
H
H
3-F-Ph
H
NMe
CH
N
2

64
Et
H
H
H
H
4-F-Ph
H
NMe
CH
N
0

65
Et
H
H
H
H
4-F-Ph
H
NMe
CH
N
2

66
Et
H
H
H
H
H
CF₃
NMe
N
CH
0

67
Me
H
H
H
H
CF₃
H
NMe
CH
CH
0

68
Et
H
H
H
H
CF₃
H
NMe
CH
CH
0

69
Et
H
H
H
H
CF₃
H
NMe
CH
CH
1

70
Et
H
H
H
H
CF₃
H
NMe
CH
CH
2

71
Et
H
H
H
H
CF₃
H
NMe
CH
CCl
0

72
Et
H
H
H
H
CF₃
H
NMe
CH
CCl
1

73
Et
H
H
H
H
CF₃
H
NMe
CH
CCl
2

74
Et
H
H
H
H
CF₃
H
NMe
CH
CBr
0

75
Et
H
H
H
H
CF₃
H
NMe
CH
CBr
1

TABLE 23

Pre-

sent

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

76
Et
H
H
H
H
CF₃
H
NMe
CH
CBr
2

77
Me
H
H
H
H
CF₃
H
O
CH
CH
0

78
Et
H
H
H
H
CF₃
H
O
CH
CH
0

79
Et
H
H
H
H
CF₃
H
O
CH
CH
1

80
Et
H
H
H
H
CF₃
H
O
CH
CH
2

81
Et
H
H
H
H
CF₃
H
O
CH
N
0

82
Et
H
H
H
H
CF₃
H
O
CH
N
1

83
Et
H
H
H
H
CF₃
H
O
CH
N
2

84
Me
H
H
H
H
CF₃
H
S
CH
CH
0

85
Et
H
H
H
H
CF₃
H
S
CH
CH
0

86
Et
H
H
H
H
CF₃
H
S
CH
CH
1

87
Et
H
H
H
H
CF₃
H
S
CH
CH
2

88
Et
Cl
H
H
H
CF₃
H
NMe
CH
N
0

89
Et
Cl
H
H
H
CF₃
H
NMe
CH
N
1

90
Et
Cl
H
H
H
CF₃
H
NMe
CH
N
2

91
Et
H
H
H
H
C(O)CF₃
H
NMe
CH
N
0

92
Me
H
H
H
SMe
CF₃
H
NMe
CH
N
0

93
Me
H
H
H
SOMe
CF₃
H
NMe
CH
N
1

94
Me
H
H
H
SO₂Me
CF₃
H
NMe
CH
N
2

95
Et
H
H
H
SEt
CF₃
H
NMe
CH
N
0

96
Et
H
H
H
SOEt
CF₃
H
NMe
CH
N
1

97
Et
H
H
H
SO₂Et
CF₃
H
NMe
CH
N
2

98
Et
H
H
H
H
Cl
H
NMe
CH
N
0

99
Et
H
H
H
H
Cl
H
NMe
CH
N
1

100
Et
H
H
H
H
Cl
H
NMe
CH
N
2

TABLE 24

Present

Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

101
Et
H
H
H
H
Br
H
NMe
CCHO
N
0

102
Et
H
H
SEt
H
CF₃
H
NMe
CH
N
0

103
Et
H
H
H
H
CF₃
H
NCH₂OEt
CH
CH
0

104
Et
H
H
H
H
H
CF₃
NCH₂OEt
N
CH
0

105
Et
H
H
H
H
CF₃
H
NCH₂CO₂Me
CH
N
0

106
Et
H
H
H
H
CF₃
H
NCH₂CO₂Et
CH
N
0

107
Et
H
H
H
H
CF₃
H
N(CH₂)₂OMe
CH
N
0

108
Et
H
H
H
H
CF₃
H
NCH₂SMe
CH
N
0

109
Et
H
H
H
H
CF₃
H
N(CH₂)₂SMe
CH
N
0

110
Et
H
H
H
H
CF₃
H
NBu
CH
N
0

111
Et
H
H
H
H
CF₃
H
NCO₂tBu
CH
N
0

112
Et
H
H
H
H
C₂F₅
H
NMe
CH
N
1

113
Et
H
H
H
H
C₂F₅
H
NMe
CH
N
2

114
Et
H
H
H
H
CH(OH)CF₃
H
NMe
CH
N
0

115
Et
H
H
H
H
CHFCF₃
H
NMe
CH
N
0

116
Et
H
F
H
H
CF₃
H
NMe
CH
N
0

117
Et
H
F
H
H
CF₃
H
NMe
CH
N
1

118
Et
H
F
H
H
CF₃
H
NMe
CH
N
2

119
Et
OMe
H
H
H
CF₃
H
NMe
CH
N
0

120
Et
OMe
H
H
H
CF₃
H
NMe
CH
N
1

121
Et
H
OMe
H
H
CF₃
H
NMe
CH
N
0

122
Et
H
OMe
H
H
CF₃
H
NMe
CH
N
1

123
Et
H
OMe
H
H
CF₃
H
NMe
CH
N
2

124
Et
H
OH
H
H
CF₃
H
NMe
CH
N
0

125
Et
H
H
H
H
NH₂
H
NMe
CH
N
0

TABLE 25

Present

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

126
Et
H
H
H
H
CHFCF₃
H
NMe
CH
N
1

127
Et
H
H
H
H
CHFCF₃
H
NMe
CH
N
2

128
Et
H
H
H
H
C₃F₇
H
NMe
CH
N
0

129
Et
H
H
H
H
C₃F₇
H
NMe
CH
N
1

130
Et
H
H
H
H
C₃F₇
H
NMe
CH
N
2

131
Et
Cl
H
H
H
C₂F₅
H
NMe
CH
N
1

132
Et
Cl
H
H
H
C₂F₅
H
NMe
CH
N
2

133
Et
H
Cl
H
H
CF₃
H
NMe
CH
N
0

134
Et
H
Cl
H
H
CF₃
H
NMe
CH
N
1

135
Et
H
Cl
H
H
CF₃
H
NMe
CH
N
2

136
Et
H
H
Cl
H
CF₃
H
NMe
CH
N
0

137
Et
H
H
Cl
H
CF₃
H
NMe
CH
N
1

138
Et
H
H
Cl
H
CF₃
H
NMe
CH
N
2

139
Et
H
H
H
Cl
CF₃
H
NMe
CH
N
0

140
Et
H
H
H
Cl
CF₃
H
NMe
CH
N
1

141
Et
H
H
H
Cl
CF₃
H
NMe
CH
N
2

142
Et
H
H
OMe
H
CF₃
H
NMe
CH
N
0

143
Et
H
H
OMe
H
CF₃
H
NMe
CH
N
1

144
Et
H
H
OMe
H
CF₃
H
NMe
CH
N
2

145
Et
H
H
H
H
SH
H
NMe
CH
N
0

146
Et
H
H
H
H
Et
H
NMe
CH
N
0

147
Et
H
H
H
H
iPr
H
NMe
CH
N
0

148
Et
H
H
H
H
NHEt
H
NMe
CH
N
0

149
Et
H
H
H
H
NEt₂
H
NMe
CH
N
0

150
Et
H
H
H
H
tBu
H
NMe
CH
N
0

TABLE 26

Present

Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

151
Et
H
H
H
H
H
CF₃
NMe
CH
N
0

152
Et
H
H
H
OMe
CF₃
H
NMe
CH
N
0

153
Et
H
H
H
OMe
CF₃
H
NMe
CH
N
1

154
Et
H
H
H
OMe
CF₃
H
NMe
CH
N
2

155
Et
H
H
H
OH
CF₃
H
NMe
CH
N
0

156
Et
F
H
H
H
CF₃
H
NMe
CH
N
0

157
Et
F
H
H
H
CF₃
H
NMe
CH
N
1

158
Et
F
H
H
H
CF₃
H
NMe
CH
N
2

159
Et
H
H
H
H
H
CF₃
NMe
CH
N
1

160
Et
H
H
H
H
H
CF₃
NMe
CH
N
2

161
Et
H
H
H
H
SCF₃
H
NMe
CH
N
0

162
Et
H
H
H
H
NMe₂
H
NMe
CH
N
0

163
Et
H
H
H
H
pyrrolidin-1-yl
H
NMe
CH
N
0

164
Et
H
H
H
H
NHCOMe
H
NMe
CH
N
0

165
Et
H
H
H
H
CH₂CF₃
H
NMe
CH
N
0

166
Et
H
H
H
H
CF₃
H
NMe
N
CH
0

167
Et
H
H
H
H
CF₃
H
NMe
N
CH
1

168
Et
H
H
H
H
CF₃
H
NMe
N
CH
2

169
Et
H
H
H
F
CF₃
H
NMe
CH
N
0

170
Et
H
H
H
F
CF₃
H
NMe
CH
N
1

171
Et
H
H
H
F
CF₃
H
NMe
CH
N
2

172
Et
H
H
H
H
N(Me)COMe
H
NMe
CH
N
0

173
Et
H
H
H
H
NH2
H
NMe
CH
N
1

174
Et
H
CF₃
H
H
CF₃
H
NMe
CH
N
0

175
Et
H
CF₃
H
H
CF₃
H
NMe
CH
N
1

TABLE 27

Pre-

sent

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

176
Et
H
CF₃
H
H
CF₃
H
NMe
CH
N
2

177
Et
H
H
H
H
NHCOCF₃
H
NMe
CH
N
0

178
Et
H
H
H
H
NHCOCF₃
H
NMe
CH
N
1

179
Et
H
H
H
H
NHCOCF₃
H
NMe
CH
N
2

180
Et
H
H
H
H
2-CF₃-Ph
H
NMe
CH
N
0

181
Et
H
H
H
H
3-CF₃-Ph
H
NMe
CH
N
0

182
Et
H
H
H
H
4-CF₃-Ph
H
NMe
CH
N
0

183
Et
H
H
H
H
CF₃
H
S
CH
N
0

184
Et
H
H
H
H
CF₃
H
S
CH
N
1

185
Et
H
H
H
H
CF₃
H
S
CH
N
2

186
CH₂CF₃
H
H
H
H
CF₃
H
NMe
CH
N
0

187
CH₂CF₃
H
H
H
H
CF₃
H
NMe
CH
N
1

188
CH₂CF₃
H
H
H
H
CF₃
H
NMe
CH
N
2

189
Et
Me
H
H
H
CF₃
H
NMe
CH
N
0

190
Et
Me
H
H
H
CF₃
H
NMe
CH
N
1

191
Et
Me
H
H
H
CF₃
H
NMe
CH
N
2

192
Et
H
Me
H
H
CF₃
H
NMe
CH
N
0

193
Et
H
Me
H
H
CF₃
H
NMe
CH
N
1

194
Et
H
Me
H
H
CF₃
H
NMe
CH
N
2

195
Et
H
H
H
H
2-CF₃-Ph
H
NMe
CH
N
1

196
Et
H
H
H
H
2-CF₃-Ph
H
NMe
CH
N
2

197
Et
H
H
H
H
3-CF₃-Ph
H
NMe
CH
N
1

198
Et
H
H
H
H
3-CF₃-Ph
H
NMe
CH
N
2

199
Et
H
H
H
H
4-CF₃-Ph
H
NMe
CH
N
1

200
Et
H
H
H
H
4-CF₃-Ph
H
NMe
CH
N
2

TABLE 28

Present

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

201
Et
H
H
CF₃
H
CF₃
H
NMe
CH
N
0

202
Et
H
H
CF₃
H
CF₃
H
NMe
CH
N
1

203
Et
H
H
CF₃
H
CF3
H
NMe
CH
N
2

204
Et
H
H
H
H
2-Cl-Ph
H
NMe
CH
N
0

205
Et
H
H
H
H
3-Cl-Ph
H
NMe
CH
N
0

206
Et
H
H
H
H
4-Cl-Ph
H
NMe
CH
N
0

207
Et
H
H
H
H
6-Cl-3-Py
H
NMe
CH
N
0

208
Et
H
H
H
H
5-F-3-Py
H
NMe
CH
N
0

209
Et
H
H
H
H
SCF₃
H
NMe
CH
N
2

210
Et
H
H
H
H
SCF₃
H
NMe
CH
N
1

211
Et
H
H
H
H
3-Py
H
NMe
CH
N
0

212
Et
H
H
H
H
4-Py
H
NMe
CH
N
0

213
Et
H
H
H
H
4-Cl-Pyrazole
H
NMe
CH
N
0

214
Et
H
H
H
H
SOCF₃
H
NMe
CH
N
2

215
Et
H
H
H
H
SO₂CF₃
H
NMe
CH
N
2

216
Et
H
H
H
H
2-Cl-Ph
H
NMe
CH
N
1

217
Et
H
H
H
H
2-Cl-Ph
H
NMe
CH
N
2

218
Et
H
H
H
H
3-Cl-Ph
H
NMe
CH
N
1

219
Et
H
H
H
H
3-Cl-Ph
H
NMe
CH
N
2

220
Et
H
H
H
H
4-Cl-Ph
H
NMe
CH
N
2

221
Et
H
H
H
H
4-Py
H
NMe
CH
N
1

222
Et
H
H
H
H
4-Py
H
NMe
CH
N
2

223
Et
H
H
H
H
6-Cl-3-Py
H
NMe
CH
N
2

224
Et
H
H
H
H
5-F-3-Py
H
NMe
CH
N
1

225
Et
H
H
H
H
5-F-3-Py
H
NMe
CH
N
2

TABLE 29

Pre-

sent

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

226
Et
H
H
H
H
4-Cl-
H
NMe
CH
N
2

Pyrazole

227
Et
H
H
H
H
3-Cl-
H
NMe
CH
N
0

triazole

228
Et
H
H
H
H
4-CF₃-
H
NMe
CH
N
0

imidazole

229
Et
H
H
H
H
2-NO₂—Ph
H
NMe
CH
N
0

230
Et
H
H
H
H
3-NO₂—Ph
H
NMe
CH
N
0

231
Et
H
H
H
H
2-CN—Ph
H
NMe
CH
N
0

232
Et
H
H
H
H
3-CN—Ph
H
NMe
CH
N
0

233
Et
H
H
H
H
4-CN—Ph
H
NMe
CH
N
0

234
Et
H
H
H
H
3-CF₃-
H
NMe
CH
N
0

triazole

235
Et
H
H
H
H
3-CF₃-5-Me-
H
NMe
CH
N
0

triazole

236
Et
H
H
H
H
3-Cl-
H
NMe
CH
N
2

triazole

237
Et
H
H
H
H
4-CF₃-
H
NMe
CH
N
1

imidazole

238
Et
H
Br
H
H
CF₃
H
NMe
CH
N
0

239
Et
H
Br
H
H
CF₃
H
NMe
CH
N
1

240
Et
H
Br
H
H
CF₃
H
NMe
CH
N
2

241
Et
H
CN
H
H
CF₃
H
NMe
CH
N
0

242
Et
H
CN
H
H
CF₃
H
NMe
CH
N
1

243
Et
H
CN
H
H
CF₃
H
NMe
CH
N
2

246
Et
H
C₂F₅
H
H
CF₃
H
NMe
CH
N
0

247
Et
H
C₂F₅
H
H
CF₃
H
NMe
CH
N
1

248
Et
H
C₂F₅
H
H
CF₃
H
NMe
CH
N
2

249
Et
H
CHO
H
H
CF₃
H
NMe
CH
N
0

250
Et
H
Ph
H
H
CF₃
H
NMe
CH
N
0

TABLE 30

Present Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

251
Et
H
CF³
H
H
CF₃
H
S
CH
N
2

253
Et
H
H
H
H
SMe
H
NMe
CH
N
0

254
Et
H
H
H
H
SO₂Me
H
NMe
CH
N
2

255
Et
H
H
H
H
SEt
H
NMe
CH
N
0

256
Et
H
H
H
H
SO₂Et
H
NMe
CH
N
2

257
Et
H
H
H
H
SiPr
H
NMe
CH
N
0

258
Et
H
H
H
H
SO₂iPr
H
NMe
CH
N
2

259
Et
H
H
H
H
SCH₂CF₃
H
NMe
CH
N
0

260
Et
H
H
H
H
SO₂CH2CF₃
H
NMe
CH
N
2

261
Et
H
H
H
H
SCH₂CH═CH₂
H
NMe
CH
N
0

262
Et
H
H
H
H
SCF₂CF₃
H
NMe
CH
N
0

263
Et
H
H
H
H
SCF₂CF₂CF₃
H
NMe
CH
N
0

264
Et
H
H
H
H
SCF(CF₃)₂
H
NMe
CH
N
0

265
Et
H
H
H
H
CH(OH)CF₃
H
NMe
CH
N
0

266
Et
H
H
H
H
CH(Cl)CF₃
H
NMe
CH
N
0

267
Et
H
CF₃
H
H
CF₃
H
S
CH
N
0

268
Et
H
H
H
H
OH
H
NMe
CH
N
0

269
Et
H
H
H
H
OH
H
NMe
CH
N
2

270
Et
H
H
H
H
OCF₂Br
H
NMe
CH
N
2

271
Et
H
H
H
H
OCF₃
H
NMe
CH
N
2

272
Et
H
H
H
H
SCF₂CF₃
H
NMe
CH
N
1

273
Et
H
H
H
H
SCF₂CF₃
H
NMe
CH
N
2

274
Et
H
H
H
H
SCF₂CF₂CF₃
H
NMe
CH
N
1

275
Et
H
H
H
H
SCF₂CF₂CF₃
H
NMe
CH
N
2

TABLE 31

Present Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

276
Et
H
H
H
H
SC(CH₃)₃
H
NMe
CH
N
0

277
Et
H
H
H
H
SO₂C(CH₃)₃
H
NMe
CH
N
2

278
Et
H
CF₃
H
H
Br
H
NMe
CH
N
0

279
Et
H
CF₃
H
H
Br
H
NMe
CH
N
1

280
Et
H
CF₃
H
H
Br
H
NMe
CH
N
2

281
Et
H
H
H
H
SCH═C═CH₂
H
NMe
CH
N
0

282
Et
H
H
H
H
SO₂CH═C═CH₂
H
NMe
CH
N
2

283
Et
H
H
H
H
SO₂CH₂CH═CH₂
H
NMe
CH
N
2

284
Et
H
H
H
H
NHSO₂CH₃
H
NMe
CH
N
2

285
Et
H
NO₂
H
H
CF₃
H
NMe
CH
N
0

286
Et
H
NO₂
H
H
CF₃
H
NMe
CH
N
1

287
Et
H
NO₂
H
H
CF₃
H
NMe
CH
N
2

289
Et
H
H
H
H
NHSO₂CF₃
H
NMe
CH
N
2

290
Et
H
H
H
H
NCH₃SO₂CF₃
H
NMe
CH
N
2

291
Et
H
H
H
H
NCH₃SO₂CH₃
H
NMe
CH
N
2

292
Et
H
CF₃
H
H
CF₂CF₃
H
NMe
CH
N
0

293
Et
H
Cl
H
H
CF₃
H
S
CH
N
0

294
Et
H
Cl
H
H
CF₃
H
S
CH
N
2

295
Et
H
H
H
H
C(OH)(CF₃)₂
H
NMe
CH
N
0

296
Et
H
H
H
H
C(Cl)(CF₃)₂
H
NMe
CH
N
0

297
Et
H
H
H
H
C(Cl)(CF₃)₂
H
NMe
CH
N
1

298
Et
H
H
H
H
C(Cl)(CF₃)₂
H
NMe
CH
N
2

299
Et
H
CF₃
H
H
CF₂CF₃
H
NMe
CH
N
2

300
Et
H
CF₃
H
H
I
H
NMe
CH
N
0

TABLE 32

Present Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

301
Et
H
CF₃
H
H
SCF₃
H
NMe
CH
N
0

302
Et
H
CF₃
H
H
SO₂CF₃
H
NMe
CH
N
2

303
Et
H
H
H
H
I
H
NMe
CH
CH
0

304
Et
H
H
H
H
H
CF(CF₃)₂
NMe
CH
CH
0

305
Et
H
H
H
H
CF(CF₃)₂
H
NMe
CH
CH
0

306
Et
H
CF₃
H
H
SCF₃
H
NMe
CH
N
2

307
Et
H
CF₃
H
H
I
H
NMe
CH
N
2

308
Et
H
H
H
H
CF₂CF₃
H
NMe
CH
CH
0

309
Et
H
H
H
H
CF₂CF₃
H
NMe
CH
CH
1

310
Et
H
H
H
H
CF₂CF₃
H
NMe
CH
CH
2

311
Et
H
H
H
H
SF₅
H
NMe
CH
CH
0

312
Et
H
H
H
H
SF₅
H
NMe
CH
CH
1

313
Et
H
H
H
H
SF₅
H
NMe
CH
CH
2

314
Et
H
CF₃
H
H
SF₅
H
NMe
CH
CH
0

315
Et
H
CF₃
H
H
SF₅
H
NMe
CH
CH
1

316
Et
H
CF₃
H
H
SF₅
H
NMe
CH
CH
2

317
Et
H
Me
H
H
CF₂CF₃
H
NMe
CH
N
0

318
Et
H
Me
H
H
CF₂CF₃
H
NMe
CH
N
1

319
Et
H
Me
H
H
CF₂CF₃
H
NMe
CH
N
2

320
Et
H
H
H
H
I
H
S
CH
N
0

321
Et
H
CF₃
H
H
I
H
S
CH
N
0

322
Et
H
H
H
H
CF₂CF₃
H
S
CH
N
0

323
Et
H
CF₃
H
H
CF₂CF₃
H
S
CH
N
0

324
Et
H
H
H
H
CF₂CF₃
H
S
CH
N
2

325
Et
H
CF₃
H
H
CF₂CF₃
H
S
CH
N
2

TABLE 33

Present

Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

326
Et
H
H
H
Cl
CF₃
H
S
CH
N
0

327
Et
H
H
H
Cl
CF₃
H
S
CH
N
2

328
Et
H
H
H
H
H
CF₃
S
N
CH
0

329
Et
H
H
H
H
H
CF₃
S
N
CH
2

330
Et
H
CH═CH₂
H
H
CF₃
H
NMe
CH
N
2

331
Et
H
Et
H
H
CF₃
H
NMe
CH
N
2

332
Et
H
CF₂CF₂CF₃
H
H
CF₃
H
NMe
CH
N
2

333
Et
H
2-
H
H
CF₃
H
NMe
CH
N
2

pyrimidyl

334
Et
H
H
H
H
SO₂NMe₂
H
NMe
CH
N
1

335
Et
H
H
H
H
SO₂NMe₂
H
NMe
CH
N
2

336
Et
H
H
H
H
CF₃
H
NMe
CH
CNH₂
0

337
Et
H
H
H
H
CF₃
H
NMe
CH
CNHCOCH₃
0

338
Et
H
H
H
H
CF₃
H
NMe
CH
CNMe₂
0

339
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CNH₂
0

340
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CNMe₂
0

341
Et
H
SF₅
H
H
CF₃
H
NMe
CH
N
0

342
Et
H
SF₅
H
H
CF₃
H
NMe
CH
N
1

343
Et
H
SF₅
H
H
CF₃
H
NMe
CH
N
0

344
Et
H
CF₃
H
H
CF₃
H
NH
CH
N
0

345
Et
H
CF₃
H
H
CF₃
H
NH
CH
N
2

346
Et
H
H
H
H
CF(CF₃)₂
H
NH
CH
CH
0

347
Et
H
H
H
H
Br
H
NMe
CCF₂H
N
0

348
Et
H
H
H
H
Br
H
NMe
CCF₂H
N
1

349
Et
H
H
H
H
Br
H
NMe
CCF₂H
N
2

350
Et
H
H
H
H
Br
H
NMe
CCH(CH₃)₂
N
0

TABLE 34

Present Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

351
Et
H
H
H
H
CF₃
H
NH
CH
N
0

352
Et
H
H
H
H
CF₃
H
NH
CH
N
1

353
Et
H
H
H
H
CF₃
H
NH
CH
N
2

354
Et
H
H
H
H
CF₃
H
NH
CH
CH
0

355
Et
H
CF₃
H
H
CF₃
H
NEt
CH
N
2

356
Et
H
CF₃
H
H
CF₃
H
NCH₂CH═CH₂
CH
N
2

357
Et
H
CF₃
H
H
CF₃
H
NCH₂CCH
CH
N
2

358
Et
H
CF₃
H
H
CF₃
H
NCH₂CN
CH
N
2

359
Et
H
CF₃
H
H
H
CF₃
NCH₂CN
N
CH
2

360
Et
H
CF₃
H
H
CF₃
H
NCH₂OEt
CH
N
2

361
Et
H
CF₃
H
H
H
CF₃
NCH₂OEt
N
CH
2

362
Et
H
CF₃
H
H
CF₃
H
NCH₂SMe
CH
N
2

363
Et
H
CF₃
H
H
CF₃
H
NPr
CH
N
2

364
Et
H
CF₃
H
H
CF₃
H
N(CH₂)₃CH₃
CH
N
2

365
Et
H
CF₃
H
H
CF₃
H
NCH₂CO₂Me
CH
N
2

366
Et
H
CF₃
H
H
H
CF₃
NCH₂CO₂Me
N
CH
2

367
Et
H
CF₃
H
H
CF₃
H
NCH₂CH═CCl₂
CH
N
2

368
Et
H
CF₃
H
H
CF₃
H
NCO₂tBu
CH
N
2

369
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CH
0

370
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CH
1

371
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CH
2

372
Et
H
CF₃
H
H
CF₃
H
NCO₂Me
CH
N
2

373
Et
H
CF₃
H
H
CF₃
H
NCOMe
CH
N
2

374
Et
H
OCF₃
H
H
CF₃
H
NMe
CH
N
0

375
Et
H
OCF₃
H
H
CF₃
H
NMe
CH
N
1

TABLE 35

Present

Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

376
Et
H
OCF₃
H
H
CF₃
H
NMe
CH
N
2

377
Et
H
CF₂CF₂CF₂CF₃
H
H
CF₃
H
NMe
CH
N
2

378
Et
H
2-pyridyl
H
H
CF₃
H
NMe
CH
N
2

379
Et
H
NH₂
H
H
CF₃
H
NMe
CH
N
2

380
Et
H
NHCOCF₃
H
H
CF₃
H
NMe
CH
N
2

381
Et
H
iPr
H
H
CF₃
H
NMe
CH
N
2

382
Et
H
CHO
H
H
CF₃
H
NMe
CH
N
2

383
CH₂CH₂CH₂CH₃
H
H
H
H
CF₃
H
NMe
CH
N
0

384
CH₂CO₂CH₃
H
H
H
H
CF₃
H
NMe
CH
N
0

385
CH₂CH═CCl₂
H
H
H
H
CF₃
H
NMe
CH
N
0

386
CH₂CCCH₃
H
H
H
H
CF₃
H
NMe
CH
N
0

387
CH₂CN
H
H
H
H
CF₃
H
NMe
CH
N
0

388
CH₂C(CH₃)₃
H
H
H
H
CF₃
H
NMe
CH
N
0

389
CH₂CH₂CN
H
H
H
H
CF₃
H
NMe
CH
N
0

390
CH₂CyBu
H
H
H
H
CF₃
H
NMe
CH
N
0

391
CF₂Br
H
H
H
H
CF₃
H
NMe
CH
N
0

392
Et
H
CF₂H
H
H
CF₃
H
NMe
CH
N
2

393
Et
H
CH₂OH
H
H
CF₃
H
NMe
CH
N
2

394
(CH₂)₃CH₃
H
H
H
H
CF₃
H
NMe
CH
N
2

395
CH₂CO₂CH₃
H
H
H
H
CF₃
H
NMe
CH
N
2

396
CH₂CH═CCl₂
H
H
H
H
CF₃
H
NMe
CH
N
2

397
CH₂CCCH₃
H
H
H
H
CF₃
H
NMe
CH
N
2

398
CH₂CN
H
H
H
H
CF₃
H
NMe
CH
N
2

399
CH₂C(CH₃)₃
H
H
H
H
CF₃
H
NMe
CH
N
2

400
CH₂CH₂CN
H
H
H
H
CF₃
H
NMe
CH
N
2

TABLE 36

Present Compound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

401
CH₂CyBu
H
H
H
H
CF₃
H
NMe
CH
N
2

402
CF₂Br
H
H
H
H
CF₃
H
NMe
CH
N
2

403
Et
H
CH₂F
H
H
CF₃
H
NMe
CH
N
2

404
CH═CH₂
H
H
H
H
CF₃
H
NMe
CH
N
0

405
CH═CH₂
H
H
H
H
CF₃
H
NMe
CH
N
1

406
CH═CH₂
H
H
H
H
CF₃
H
NMe
CH
N
2

407
Et
H
H
H
H
H
CF₃
S
CH
N
0

408
Et
H
H
H
H
H
CF₃
S
CH
N
2

409
Et
H
OCF₃
H
H
CF₂CF₃
H
NMe
CH
N
0

410
Et
H
OCF₃
H
H
CF₂CF₃
H
NMe
CH
N
1

411
Et
H
OCF₃
H
H
CF₂CF₃
H
NMe
CH
N
2

412
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CCH₃
0

413
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CCH₃
1

414
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CCH₃
2

415
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CF
0

416
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CF
1

417
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CF
2

418
Et
H
CF₃
H
H
CF₂CF₃
H
NMe
CH
CH
0

419
Et
H
CF₃
H
H
CF₂CF₃
H
NMe
CH
CH
1

420
Et
H
CF₃
H
H
CF₂CF₃
H
NMe
CH
CH
2

421
CH₂CyPr
H
H
H
H
CF₃
H
NMe
CH
N
0

422
CH₂CyPr
H
H
H
H
CF₃
H
NMe
CH
N
1

423
CH₂CyPr
H
H
H
H
CF₃
H
NMe
CH
N
2

424
Et
H
CF₃
H
H
CF₃
H
O
CH
CH
0

425
Et
H
CF₃
H
H
CF₃
H
O
CH
CH
2

TABLE 37

Pre-

sent

Com-

pound
R¹
R²
R³
R⁴
R⁵
R⁶
R⁷
A¹
A²
A³
n

426
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CBr
0

427
Et
H
CF₃
H
H
CF₃
H
NMe
CH
CSCH₂CH₃
0

In the above Tables 20-37, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, iPr represents an isopropyl group, tBu represents a tert-butyl group, CyPr represents a cyclopropyl group, CyBu represents a cyclobutyl group, 2-F-Ph represents a 2-fluorophenyl group, 3-F-Ph represents a 3-fluorophenyl group, 4-F-Ph represents a 4-fluorophenyl group, 2-CF₃-Ph represents a 2-trifluoromethylphenyl group, 3-CF₃-Ph represents a 3-trifluoromethylphenyl group, 4-CF₃-Ph represents a 4-trifluoromethylphenyl group, 2-Cl-Ph represents a 2-chlorophenyl group, 3-Cl-Ph represents a 3-chlorophenyl group, 4-Cl-Ph represents a 4-chlorophenyl group, 2-NO₂-Ph represents a 2-nitrophenyl group, 3-NO₂-Ph represents a 3-nitrophenyl group, 2-CN-Ph represents a 2-cyanophenyl group, 3-CN-Ph represents a 3-cyanophenyl group, 4-CN-Ph represents a 4-cyanophenyl group, 3-Py represents a pyridin-3-yl group, 4-Py represents a pyridin-4-yl group, 6-Cl-3-Py represents a 6-chloropyridin-3-yl group, 5-F-3-Py represents a 6-fluoropyridin-3-yl group, 4-Cl-pyrazole represents a 4-chloropyrazol-1-yl group, 3-Cl-triazole represents a 3-chloro-(1H-1,2,4-triazol)-1-yl group, 3-CF₃-triazole represents a 3-trifluoromethyl-(1H-1,2,4-triazol)-1-yl group, 3-CF₃-5-Me-triazole represents a 3-trifluoromethyl-5-methyl-(1H-1,2,4-triazol)-1-yl group, and 4-CF₃-imidazole represents a 4-trifluoromethylimidazol-1-yl group.

The ¹H-NMR data of the present compounds listed in Tables 20-37 are shown below.

Present Compound 92

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.36-8.35 (1H, m), 7.49 (1H, t), 7.17 (2H, d), 3.70 (3H, s), 2.41 (6H, s).

Present Compound 94

¹H-NMR (CDCl₃) δ: 8.80-8.78 (1H, m), 8.60 (2H, d), 8.30-8.28 (1H, m), 8.08 (1H, t), 3.70 (3H, s), 3.09 (6H, s).

Present Compound 95

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.35-8.34 (1H, m), 7.47-7.43 (1H, m), 7.28-7.25 (2H, m), 3.69 (3H, s), 2.97-2.79 (4H, m), 1.24 (6H, t).

Present Compound 96

¹H-NMR (CDCl₃) δ: 8.85-8.75 (1H, m), 8.38-7.96 (4H, m), 3.81-3.71 (3H, m), 3.15-2.65 (4H, m), 1.22-1.03 (6H, m).

Present Compound 97

¹H-NMR (CDCl₃) δ: 8.79 (1H, d), 8.54 (2H, d), 8.27 (1H, d), 8.06 (1H, t), 3.71 (3H, s), 3.32-3.07 (4H, m), 1.19 (6H, t).

Present Compound 98

¹H-NMR (CDCl₃) δ: 8.39 (1H, d), 8.07 (1H, d), 7.54-7.48 (2H, m), 7.45-7.43 (1H, m), 7.37-7.32 (1H, m), 3.72 (3H, s), 2.86 (2H, q), 1.23 (3H, t).

Present Compound 99

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.26-8.22 (1H, m), 8.06 (1H, d), 7.84-7.79 (1H, m), 7.71-7.65 (1H, m), 7.60-7.57 (1H, m), 3.84 (3H, s), 3.39-3.29 (1H, m), 2.99-2.89 (1H, m), 1.29 (3H, t).

Present Compound 100

¹H-NMR (CDCl₃) δ: 8.42 (1H, d), 8.23-8.20 (1H, m), 8.02 (1H, d), 7.86-7.77 (2H, m), 7.57-7.54 (1H, m), 3.67 (3H, s), 3.42 (2H, q), 1.25 (3H, t).

Present Compound 101

¹H-NMR (CDCl₃) δ: 10.83 (1H, s), 8.63 (1H, s), 7.55-7.43 (3H, m), 7.38-7.32 (1H, m), 3.76 (3H, s), 2.89 (2H, q), 1.24 (3H, t).

Present Compound 102

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.33-8.31 (1H, m), 7.47-7.42 (2H, m), 7.39-7.38 (1H, m), 3.77 (3H, s), 2.97 (2H, q), 2.82 (2H, q), 1.34 (3H, t), 1.21 (3H, t).

Present Compound 103

¹H-NMR (CDCl₃) δ: 8.12 (1H, s), 7.69 (1H, d), 7.62-7.57 (1H, m), 7.53-7.45 (3H, m), 7.36-7.31 (1H, m), 5.43 (2H, s), 3.26 (2H, q), 2.84 (2H, q), 1.22 (3H, t), 1.04 (3H, t).

Present Compound 104

¹H-NMR (CDCl₃) δ: 7.94-7.88 (2H, m), 7.61-7.56 (1H, m), 7.54-7.44 (3H, m), 7.37-7.30 (1H, m), 5.44 (2H, s), 3.27 (2H, q), 2.84 (2H, q), 1.22 (3H, t), 1.05 (3H, t).

Present Compound 107

¹H-NMR (CDCl₃) δ: 8.72-8.69 (1H, m), 8.33-8.30 (1H, m), 7.55-7.45 (3H, m), 7.37-7.32 (1H, m), 4.40 (2H, t), 3.65 (2H, t), 3.14 (3H, s), 2.87 (2H, q), 1.24 (3H, t).

Present Compound 108

¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.26 (1H, d), 7.50-7.39 (3H, m), 7.33-7.26 (1H, m), 5.23 (2H, s), 2.81 (2H, q), 1.98 (3H, s), 1.17 (3H, t).

Present Compound 109

¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.32 (1H, d), 7.56-7.46 (3H, m), 7.39-7.33 (1H, m), 4.40 (2H, t), 2.92-2.80 (4H, m), 1.85 (3H, s), 1.24 (3H, t).

Present Compound 110

¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.31 (1H, d), 7.55-7.47 (2H, m), 7.45-7.41 (1H, m), 7.38-7.32 (1H, m), 4.21 (2H, t), 2.89 (2H, q), 1.75-1.63 (2H, m), 1.28-1.11 (5H, m), 0.78 (3H, t).

Present Compound 111

¹H-NMR (CDCl₃) δ: 8.84-8.81 (1H, m), 8.65-8.61 (1H, m), 7.48-7.37 (3H, m), 7.35-7.27 (1H, m), 2.74-2.64 (2H, m), 1.26 (9H, s), 1.10-1.04 (3H, m).

Present Compound 114

¹H-NMR (CDCl₃) δ: 8.59-8.52 (1H, m), 8.31-8.17 (1H, m), 7.61-7.32 (4H, m), 5.24 (1H, brs), 3.77 (3H, s), 2.97-2.82 (2H, m), 1.31-1.15 (3H, m).

Present Compound 115

¹H-NMR (CDCl₃) δ: 8.51 (1H, s), 8.22 (1H, s), 7.55-7.50 (2H, m), 7.47-7.43 (1H, m), 7.38-7.32 (1H, m), 5.81 (1H, dq), 3.76 (3H, s), 2.88 (2H, q), 1.24 (3H, t).

Present Compound 119

¹H-NMR (CDCl₃) δ: 8.71-8.70 (1H, m), 8.31-8.29 (1H, m), 7.49-7.45 (1H, m), 7.14-7.09 (2H, m), 4.00 (3H, s), 3.71 (3H, s), 2.74 (2H, q), 1.04 (3H, t).

Present Compound 121

¹H-NMR (CDCl₃) δ: 8.68-8.66 (1H, m), 8.28-8.27 (1H, m), 7.35 (1H, d), 6.99 (1H, d), 6.86-6.83 (1H, m), 3.88 (3H, s), 3.74 (3H, s), 2.84 (2H, q), 1.22 (3H, t).

Present Compound 122

¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.29-8.27 (1H, m), 7.77 (1H, d), 7.53 (1H, d), 7.19-7.15 (1H, m), 4.00 (3H, s), 3.89 (3H, s), 3.46-3.36 (1H, m), 3.00-2.90 (1H, m), 1.33 (3H, t).

Present Compound 123

¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.27-8.25 (1H, m), 7.71 (1H, d), 7.46 (1H, d), 7.32-7.28 (1H, m), 3.99 (3H, s), 3.70 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

Present Compound 124

¹H-NMR (CDCl₃) δ: 9.12 (1H, brs), 8.72-8.70 (1H, m), 8.33-8.30 (1H, m), 7.15 (1H, d), 6.88 (1H, d), 6.63-6.60 (1H, m), 3.77 (3H, s), 2.77 (2H, q), 1.19 (3H, t).

Present Compound 126

¹H-NMR (CDCl₃) δ: 8.55 (1H, d), 8.26 (1H, d), 8.21 (1H, d), 7.83 (1H, t), 7.69 (1H, t), 7.60 (1H, d), 5.84 (1H, dq), 3.88 (3H, s), 3.42-3.30 (1H, m), 3.03-2.91 (1H, m), 1.33-1.25 (3H, m).

Present Compound 127

¹H-NMR (CDCl₃) δ: 8.53 (1H, s), 8.26-8.16 (2H, m), 7.88-7.78 (2H, m), 7.59-7.53 (1H, m), 5.82 (1H, dq), 3.70 (3H, s), 3.44 (2H, q), 1.26 (3H, t).

Present Compound 131

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.29 (1H, d), 7.74-7.68 (1H, m), 7.49-7.40 (2H, m), 3.73 (3H, s), 2.74 (2H, q), 1.06 (3H, t).

Present Compound 132

¹H-NMR (CDCl₃) δ: 8.64 (1H, s), 8.24 (1H, s), 7.65 (1H, d), 7.58 (1H, t), 7.39 (1H, d), 3.72 (3H, s), 3.63-3.47 (1H, m), 3.37-3.22 (1H, m), 1.38-1.30 (3H, m).

Present Compound 136

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.33-8.32 (1H, m), 7.52-7.49 (1H, m), 7.47-7.43 (2H, m), 3.79 (3H, s), 2.85 (2H, q), 1.23 (3H, t).

Present Compound 137

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.33-8.31 (1H, m), 8.20 (1H, d), 7.81-7.78 (1H, m), 7.60 (1H, d), 3.93 (3H, s), 3.42-3.32 (1H, m), 3.02-2.92 (1H, m), 1.31 (3H, t).

Present Compound 138

¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.29-8.28 (1H, m), 8.16 (1H, d), 7.80-7.77 (1H, m), 7.57 (1H, d), 3.75 (3H, s), 3.40 (2H, q), 1.26 (3H, t).

Present Compound 139

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.37-8.35 (1H, m), 7.48-7.44 (1H, m), 7.38-7.34 (2H, m), 3.72 (3H, s), 3.00-2.83 (2H, m), 1.26 (3H, t).

Present Compound 140

¹H-NMR (CDCl₃) δ: 8.80-8.78 (1H, m), 8.35-8.34 (1H, m), 8.11-8.08 (1H, m), 7.79 (1H, t), 7.73-7.71 (1H, m), 3.77 (3H, s), 3.37-3.27 (1H, m), 3.09-2.99 (1H, m), 1.25 (3H, t).

Present Compound 141

¹H-NMR (CDCl₃) δ: 8.77-8.76 (1H, m), 8.32-8.30 (1H, m), 8.16-8.13 (1H, m), 7.89-7.87 (1H, m), 7.77 (1H, t), 3.73 (3H, s), 3.61-3.49 (1H, m), 3.34-3.24 (1H, m), 1.26 (3H, t).

Present Compound 142

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.32-8.30 (1H, m), 7.54 (1H, d), 7.10-7.06 (1H, m), 7.03 (1H, d), 3.85 (3H, s), 3.77 (3H, s), 2.68 (2H, q), 1.12 (3H, t).

Present Compound 143

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.31-8.30 (1H, m), 8.14 (1H, d), 7.34-7.30 (1H, m), 7.08 (1H, d), 3.93 (3H, s), 3.89 (3H, s), 3.29-3.19 (1H, m), 2.97-2.86 (1H, m), 1.26 (3H, t).

Present Compound 144

¹H-NMR (CDCl₃) δ: 8.74-8.73 (1H, m), 8.28-8.27 (1H, m), 8.13 (1H, d), 7.25-7.21 (1H, m), 7.03 (1H, d), 3.94 (3H, s), 3.74 (3H, s), 3.34 (2H, q), 1.24 (3H, t).

Present Compound 146

¹H-NMR (CDCl₃) δ: 8.30 (1H, s), 7.93 (1H, s), 7.49-7.42 (3H, m), 7.33-7.27 (1H, m), 3.72 (3H, s), 2.89-2.78 (4H, m), 1.33 (3H, t), 1.22 (3H, t).

Present Compound 148

¹H-NMR (CDCl₃) δ: 7.94 (1H, d), 7.48-7.39 (3H, m), 7.34-7.25 (2H, m), 3.67 (3H, s), 3.26-3.16 (2H, m), 2.89-2.80 (2H, m), 1.34-1.27 (3H, m), 1.26-1.19 (3H, m).

Present Compound 149

¹H-NMR (CDCl₃) δ: 8.09 (1H, d), 7.50-7.41 (4H, m), 7.34-7.27 (1H, m), 3.68 (3H, s), 3.38 (4H, q), 2.86 (2H, q), 1.23 (3H, t), 1.17 (6H, t).

Present Compound 152

¹H-NMR (CDCl₃) δ: 8.71-8.69 (1H, m), 8.33-8.31 (1H, m), 7.47 (1H, t), 7.06 (1H, d), 6.86 (1H, d), 3.76 (3H, s), 3.69 (3H, s), 2.98-2.82 (2H, m), 1.25 (3H, t).

Present Compound 153

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.30-8.29 (1H, m), 7.79-7.76 (2H, m), 7.22-7.18 (1H, m), 3.86 (3H, s), 3.73 (3H, s), 3.42-3.30 (1H, m), 3.09-2.97 (1H, m), 1.29 (3H, t).

Present Compound 154

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.27-8.25 (1H, m), 7.82-7.73 (2H, m), 7.37-7.34 (1H, m), 3.83 (3H, s), 3.68 (3H, s), 3.67-3.56 (1H, m), 3.36-3.26 (1H, m), 1.26 (3H, t).

Present Compound 155

¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.29-8.27 (1H, m), 7.93 (1H, brs), 7.36 (1H, t), 7.09-7.06 (1H, m), 6.95-6.92 (1H, m), 3.85 (3H, s), 2.87-2.78 (2H, m), 1.21 (3H, t).

Present Compound 156

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.33-8.31 (1H, m), 7.51-7.45 (1H, m), 7.36-7.31 (2H, m), 3.75 (3H, s), 2.78 (2H, q), 1.10 (3H, t).

Present Compound 157

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.29-8.27 (1H, m), 7.70-7.64 (1H, m), 7.44-7.38 (1H, m), 7.33 (1H, d), 3.81 (3H, s), 3.53-3.43 (1H, m), 3.42-3.31 (1H, m), 1.33 (3H, t).

Present Compound 158

¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.28-8.26 (1H, m), 7.84-7.78 (1H, m), 7.55-7.49 (1H, m), 7.38-7.35 (1H, m), 3.77 (3H, s), 3.50-3.34 (2H, m), 1.34 (3H, t).

Present Compound 162

¹H-NMR (CDCl₃) δ: 8.14 (1H, d), 7.51-7.40 (4H, m), 7.35-7.27 (1H, m), 3.69 (3H, s), 3.00 (6H, s), 2.90-2.81 (2H, m), 1.26-1.19 (3H, m).

Present Compound 163

¹H-NMR (CDCl₃) δ: 7.92 (1H, d), 7.48-7.43 (3H, m), 7.34-7.28 (1H, m), 7.26 (1H, d), 3.68 (3H, s), 3.40-3.32 (4H, m), 2.84 (2H, q), 2.08-2.05 (4H, m), 1.22 (3H, t).

Present Compound 164

¹H-NMR (CDCl₃) δ: 9.72 (1H, s), 8.41 (1H, d), 8.23 (1H, d), 7.37-7.28 (3H, m), 7.18-7.13 (1H, m), 3.58 (3H, s), 2.74 (2H, q), 2.02 (3H, s), 1.09 (3H, t).

Present Compound 169

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.37-8.35 (1H, m), 7.54-7.48 (1H, m), 7.27-7.24 (1H, m), 7.09-7.03 (1H, m), 3.77 (3H, d), 2.93 (2H, q), 1.28 (3H, t).

Present Compound 170

¹H-NMR (CDCl₃) δ: 8.79-8.76 (1H, m), 8.35-8.32 (1H, m), 8.03 (1H, d), 7.87-7.80 (1H, m), 7.43 (1H, t), 3.84 (3H, d), 3.51-3.40 (1H, m), 3.13-3.02 (1H, m), 1.33 (3H, t).

Present Compound 171

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.32-8.30 (1H, m), 8.07-8.04 (1H, m), 7.86-7.80 (1H, m), 7.62-7.57 (1H, m), 3.76 (3H, s), 3.69-3.58 (1H, m), 3.41-3.31 (1H, m), 1.29 (3H, t).

Present Compound 172

¹H-NMR (CDCl₃) δ: 8.32 (1H, d), 7.94 (1H, d), 7.57-7.48 (2H, m), 7.47-7.43 (1H, m), 7.39-7.33 (1H, m), 3.77 (3H, s), 3.36 (3H, s), 2.91 (2H, q), 1.93 (3H, s), 1.27 (3H, t).

Present Compound 173

¹H-NMR (CDCl₃) δ: 8.21 (1H, dd), 8.03 (1H, d), 7.77 (1H, td), 7.65 (1H, td), 7.57 (1H, dd), 7.37 (1H, d), 3.78 (3H, s), 3.36-3.24 (1H, m), 2.96-2.83 (1H, m), 1.26 (3H, t).

Present Compound 177

¹H-NMR (CDCl₃) δ: 8.55 (1H, d), 8.39 (1H, d), 8.21 (1H, brs), 7.55-7.42 (3H, m), 7.38-7.31 (1H, m), 3.74 (3H, s), 2.86 (2H, q), 1.23 (3H, t).

Present Compound 178

¹H-NMR (DMSO-D₆) δ: 11.57 (1H, brs), 8.68-8.64 (1H, m), 8.45-8.42 (1H, m), 8.10 (1H, d), 7.90 (2H, dd), 7.78 (1H, t), 3.83 (3H, s), 3.41-3.30 (1H, m), 2.94-2.81 (1H, m), 1.16 (3H, t).

Present Compound 179

¹H-NMR (CDCl₃) δ: 9.18 (1H, brs), 8.52-8.48 (1H, m), 8.38-8.34 (1H, m), 8.25-8.17 (1H, m), 7.87-7.76 (2H, m), 7.59-7.52 (1H, m), 3.65 (3H, s), 3.47 (2H, q), 1.26 (3H, t).

Present Compound 180

¹H-NMR (CDCl₃) δ: 8.40 (1H, d), 8.06 (1H, d), 7.82 (1H, d), 7.66-7.59 (1H, m), 7.58-7.46 (4H, m), 7.44-7.39 (1H, m), 7.38-7.31 (1H, m), 3.79 (3H, s), 2.90 (2H, q), 1.26 (3H, t).

Present Compound 181

¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.26 (1H, d), 7.89 (1H, s), 7.83 (1H, d), 7.69-7.60 (2H, m), 7.53-7.46 (3H, m), 7.38-7.33 (1H, m), 3.78 (3H, s), 2.88 (2H, q), 1.25 (3H, t).

Present Compound 182

¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.27 (1H, d), 7.78-7.75 (4H, m), 7.56-7.44 (3H, m), 7.39-7.32 (1H, m), 3.78 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 189

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.30-8.28 (1H, m), 7.50-7.47 (1H, m), 7.40 (1H, t), 7.35-7.32 (1H, m), 3.71 (3H, s), 2.64 (3H, s), 2.53 (2H, q), 1.00 (3H, t).

Present Compound 190

¹H-NMR (CDCl₃) δ: 8.71-8.70 (1H, m), 8.26-8.24 (1H, m), 7.53 (1H, t), 7.47-7.44 (1H, m), 7.31-7.28 (1H, m), 3.73 (3H, s), 3.54-3.43 (1H, m), 3.27-3.17 (1H, m), 2.66 (3H, s), 1.29 (3H, t).

Present Compound 191

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.24-8.22 (1H, m), 7.65 (1H, t), 7.60-7.56 (1H, m), 7.34-7.31 (1H, m), 3.73 (3H, s), 3.52-3.32 (2H, m), 2.85 (3H, s), 1.32 (3H, t).

Present Compound 192

¹H-NMR (CDCl₃) δ: 8.71-8.69 (1H, m), 8.31-8.30 (1H, m), 7.35-7.31 (2H, m), 7.19-7.15 (1H, m), 3.76 (3H, s), 2.85 (2H, q), 2.46 (3H, s), 1.22 (3H, t).

Present Compound 193

¹H-NMR (CDCl₃) δ: 8.74-8.73 (1H, m), 8.30-8.28 (1H, m), 8.06-8.05 (1H, m), 7.49-7.48 (2H, m), 3.88 (3H, s), 3.42-3.32 (1H, m), 3.00-2.90 (1H, m), 2.58 (3H, s), 1.32 (3H, t).

Present Compound 194

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.27-8.26 (1H, m), 8.03-8.02 (1H, m), 7.64-7.61 (1H, m), 7.44 (1H, d), 3.70 (3H, s), 3.41 (2H, q), 2.59 (3H, s), 1.26 (3H, t).

Present Compound 195

¹H-NMR (CDCl₃) δ: 8.45 (1H, d), 8.26 (1H, d), 8.05 (1H, d), 7.85-7.78 (2H, m), 7.73-7.61 (3H, m), 7.56 (1H, t), 7.44 (1H, d), 3.91 (3H, s), 3.46-3.32 (1H, m), 3.03-2.91 (1H, m), 1.29 (3H, t).

Present Compound 196

¹H-NMR (CDCl₃) δ: 8.43 (1H, d), 8.28-8.20 (1H, m), 8.06-8.00 (1H, m), 7.90-7.75 (3H, m), 7.67-7.59 (2H, m), 7.54 (1H, t), 7.44 (1H, d), 3.74 (3H, s), 3.49 (2H, q), 1.25 (3H, t).

Present Compound 197

¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.29-8.23 (2H, m), 7.92-7.78 (3H, m), 7.74-7.60 (4H, m), 3.90 (3H, s), 3.47-3.33 (1H, m), 3.06-2.93 (1H, m), 1.32 (3H, t).

Present Compound 198

¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.26-8.19 (2H, m), 7.92-7.89 (1H, m), 7.87-7.76 (3H, m), 7.69-7.57 (3H, m), 3.73 (3H, s), 3.50 (2H, q), 1.27 (3H, t).

Present Compound 199

¹H-NMR (CDCl₃) δ: 8.71 (1H, d), 8.29-8.23 (2H, m), 7.85-7.79 (1H, m), 7.78-7.75 (4H, m), 7.70 (1H, td), 7.63 (1H, dd), 3.90 (3H, s), 3.44-3.32 (1H, m), 3.05-2.92 (1H, m), 1.31 (3H, t).

Present Compound 200

¹H-NMR (CDCl₃) δ: 8.70 (1H, d), 8.27-8.19 (2H, m), 7.87-7.78 (2H, m), 7.77-7.75 (4H, m), 7.62-7.57 (1H, m), 3.73 (3H, s), 3.48 (2H, d), 1.26 (3H, t).

Present Compound 201

¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.35-8.34 (1H, m), 7.78-7.74 (1H, m), 7.71-7.69 (1H, m), 7.54 (1H, d), 3.80 (3H, s), 2.98 (2H, q), 1.31 (3H, t).

Present Compound 202

¹H-NMR (CDCl₃) δ: 8.79-8.78 (1H, m), 8.44-8.41 (1H, m), 8.35-8.33 (1H, m), 8.10-8.06 (1H, m), 7.89-7.87 (1H, m), 3.94 (3H, s), 3.50-3.40 (1H, m), 3.07-2.97 (1H, m), 1.34 (3H, t).

Present Compound 203

¹H-NMR (CDCl₃) δ: 8.78-8.77 (1H, m), 8.40-8.37 (1H, m), 8.31-8.30 (1H, m), 8.10-8.06 (1H, m), 7.86-7.84 (1H, m), 3.75 (3H, s), 3.45 (2H, q), 1.28 (3H, t).

Present Compound 204

¹H-NMR (CDCl₃) δ: 8.53 (1H, d), 8.19 (1H, d), 7.56-7.26 (8H, m), 3.79 (3H, s), 2.88 (2H, q), 1.24 (3H, t).

Present Compound 205

¹H-NMR (CDCl₃) δ: 8.63 (1H, d), 8.23 (1H, d), 7.65-7.29 (8H, m), 3.77 (3H, s), 2.87 (2H, q), 1.23 (3H, t).

Present Compound 206

¹H-NMR (CDCl₃) δ: 8.62 (1H, d), 8.22 (1H, d), 7.59-7.53 (2H, m), 7.51-7.40 (5H, m), 7.36-7.29 (1H, m), 3.77 (3H, s), 2.87 (2H, q), 1.23 (3H, t).

Present Compound 207

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.62 (1H, d), 8.24 (1H, d), 7.93 (1H, dd), 7.56-7.42 (4H, m), 7.40-7.34 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 208

¹H-NMR (CDCl₃) δ: 8.78-8.74 (1H, m), 8.67-8.64 (1H, m), 8.52 (1H, d), 8.27 (1H, d), 7.73-7.65 (1H, m), 7.57-7.46 (3H, m), 7.41-7.34 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 211

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 8.69-8.62 (2H, m), 8.27 (1H, d), 8.00-7.92 (1H, m), 7.55-7.31 (5H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 212

¹H-NMR (CDCl₃) δ: 8.75-8.69 (3H, m), 8.33 (1H, d), 7.63-7.57 (2H, m), 7.56-7.44 (3H, m), 7.40-7.32 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 213

¹H-NMR (CDCl₃) δ: 8.79 (1H, d), 8.28 (1H, d), 7.97 (1H, s), 7.70 (1H, s), 7.55-7.43 (3H, m), 7.40-7.30 (1H, m), 3.77 (3H, s), 2.87 (2H, q), 1.23 (3H, t).

Present Compound 216

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.26 (1H, dd), 8.16 (1H, d), 7.84-7.78 (1H, m), 7.69 (1H, td), 7.62 (1H, dd), 7.56-7.52 (1H, m), 7.46-7.43 (1H, m), 7.42-7.33 (2H, m), 3.90 (3H, s), 3.44-3.31 (1H, m), 3.03-2.91 (1H, m), 1.30 (3H, t).

Present Compound 217

¹H-NMR (CDCl₃) δ: 8.55 (1H, d), 8.24-8.20 (1H, m), 8.14 (1H, d), 7.85-7.76 (2H, m), 7.59 (1H, dd), 7.53 (1H, dd), 7.44 (1H, dd), 7.40-7.29 (2H, m), 3.73 (3H, s), 3.49 (2H, q), 1.25 (3H, t).

Present Compound 218

¹H-NMR (CDCl₃) δ: 8.68-8.64 (1H, m), 8.28-8.23 (1H, m), 8.22-8.19 (1H, m), 7.84-7.78 (1H, m), 7.71-7.66 (1H, m), 7.65-7.59 (2H, m), 7.56-7.49 (1H, m), 7.46-7.41 (1H, m), 7.40-7.34 (1H, m), 3.89 (3H, s), 3.45-3.33 (1H, m), 3.04-2.92 (1H, m), 1.31 (3H, t).

Present Compound 219

¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.22 (1H, dd), 8.18 (1H, d), 7.86-7.76 (2H, m), 7.64-7.62 (1H, m), 7.59 (1H, dd), 7.52 (1H, dt), 7.42 (1H, t), 7.36 (1H, dt), 3.72 (3H, s), 3.48 (2H, q), 1.26 (3H, t).

Present Compound 220

¹H-NMR (CDCl₃) δ: 8.66-8.62 (1H, m), 8.24-8.20 (1H, m), 8.19-8.17 (1H, m), 7.86-7.75 (2H, m), 7.62-7.54 (3H, m), 7.48-7.42 (2H, m), 3.71 (3H, s), 3.56-3.41 (2H, m), 1.25 (3H, t).

Present Compound 221

¹H-NMR (CDCl₃) δ: 8.76 (1H, d), 8.74 (2H, dd), 8.30 (1H, d), 8.26 (1H, dd), 7.83 (1H, td), 7.71 (1H, td), 7.65-7.59 (3H, m), 3.91 (3H, s), 3.44-3.32 (1H, m), 3.05-2.93 (1H, m), 1.31 (3H, t).

Present Compound 222

¹H-NMR (CDCl₃) δ: 9.07-8.56 (3H, m), 8.28 (1H, d), 8.25-8.20 (1H, m), 7.89-7.78 (2H, m), 7.66-7.56 (3H, m), 3.73 (3H, s), 3.47 (2H, q), 1.26 (3H, t).

Present Compound 223

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.64 (1H, d), 8.26-8.21 (1H, m), 8.18 (1H, d), 7.92 (1H, dd), 7.89-7.78 (2H, m), 7.60 (1H, dd), 7.47 (1H, d), 3.73 (3H, s), 3.52-3.41 (2H, m), 1.26 (3H, t).

Present Compound 224

¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.69 (1H, d), 8.53 (1H, d), 8.29-8.23 (2H, m), 7.87-7.80 (1H, m), 7.74-7.67 (2H, m), 7.66-7.61 (1H, m), 3.91 (3H, s), 3.45-3.31 (1H, m), 3.05-2.93 (1H, m), 1.31 (3H, t).

Present Compound 225

¹H-NMR (CDCl₃) δ: 8.77-8.74 (1H, m), 8.67 (1H, d), 8.53 (1H, d), 8.26-8.23 (1H, m), 8.22-8.20 (1H, m), 7.89-7.79 (2H, m), 7.71-7.66 (1H, m), 7.64-7.59 (1H, m), 3.74 (3H, s), 3.48 (2H, q), 1.27 (3H, t).

Present Compound 226

¹H-NMR (DMSO-D₆) δ: 8.96 (1H, d), 8.89 (1H, s), 8.54 (1H, d), 8.14 (1H, dd), 8.02-7.87 (4H, m), 3.60 (3H, s), 3.55 (2H, q), 1.12 (3H, t).

Present Compound 227

¹H-NMR (CDCl₃) δ: 8.74 (1H, d), 8.48 (1H, s), 8.28 (1H, d), 7.57-7.50 (2H, m), 7.49-7.45 (1H, m), 7.40-7.34 (1H, m), 3.79 (3H, s), 2.88 (2H, q), 1.24 (3H, t).

Present Compound 228

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.10 (1H, d), 7.89 (1H, s), 7.66-7.63 (1H, m), 7.58-7.43 (3H, m), 7.41-7.33 (1H, m), 3.80 (3H, s), 2.90 (2H, q), 1.25 (3H, t).

Present Compound 229

¹H-NMR (CDCl₃) δ: 8.38 (1H, d), 8.05 (1H, d), 7.98 (1H, dd), 7.70 (1H, td), 7.60-7.43 (5H, m), 7.39-7.31 (1H, m), 3.78 (3H, s), 2.89 (2H, q), 1.26 (3H, t).

Present Compound 230

¹H-NMR (CDCl₃) δ: 8.69 (1H, d), 8.54-8.51 (1H, m), 8.31-8.29 (1H, m), 8.27 (1H, dd), 7.98 (1H, d), 7.69 (1H, t), 7.57-7.46 (3H, m), 7.40-7.34 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.26 (3H, t).

Present Compound 231

¹H-NMR (CDCl₃) δ: 8.62 (1H, d), 8.25 (1H, d), 7.83 (1H, dd), 7.71 (1H, td), 7.59 (1H, dd), 7.55-7.46 (4H, m), 7.39-7.32 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 232

¹H-NMR (CDCl₃) δ: 8.63 (1H, d), 8.24 (1H, d), 7.93 (1H, s), 7.89 (1H, d), 7.74-7.58 (2H, m), 7.56-7.45 (3H, m), 7.40-7.33 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 233

¹H-NMR (CDCl₃) δ: 8.66 (1H, d), 8.27 (1H, d), 7.83-7.73 (4H, m), 7.56-7.45 (3H, m), 7.40-7.32 (1H, m), 3.79 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 234

¹H-NMR (CDCl₃) δ: 8.78 (1H, d), 8.68 (1H, s), 8.34 (1H, d), 7.54-7.26 (4H, m), 3.80 (3H, s), 2.93-2.82 (2H, m), 1.28-1.19 (3H, m).

Present Compound 235

¹H-NMR (CDCl₃) δ: 8.55 (1H, d), 8.17 (1H, d), 7.57-7.24 (4H, m), 3.81 (3H, s), 2.93-2.86 (2H, m), 2.60 (3H, s), 1.28-1.23 (3H, m).

Present Compound 236

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.49 (1H, s), 8.27 (1H, d), 8.25-8.22 (1H, m), 7.89-7.78 (2H, m), 7.63-7.57 (1H, m), 3.73 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

Present Compound 237

¹H-NMR (CDCl₃) δ: 8.57 (1H, d), 8.27 (1H, d), 8.11 (1H, d), 7.92 (1H, s), 7.88-7.82 (1H, m), 7.75-7.68 (2H, m), 7.65 (1H, d), 3.93 (3H, s), 3.46-3.32 (1H, m), 3.06-2.94 (1H, m), 1.32 (3H, t).

Present Compound 238

¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.33-8.32 (1H, m), 7.59 (1H, d), 7.50-7.47 (1H, m), 7.30 (1H, d), 3.77 (3H, s), 2.91 (2H, q), 1.27 (3H, t).

Present Compound 239

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.39 (1H, d), 8.32-8.31 (1H, m), 7.84-7.81 (1H, m), 7.49 (1H, d), 3.91 (3H, s), 3.50-3.40 (1H, m), 3.06-2.96 (1H, m), 1.35 (3H, t).

Present Compound 240

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.37 (1H, d), 8.31-8.29 (1H, m), 7.99-7.96 (1H, m), 7.44 (1H, d), 3.72 (3H, s), 3.44 (2H, q), 1.28 (3H, t).

Present Compound 241

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.35-8.34 (1H, m), 7.70-7.69 (1H, m), 7.63-7.60 (1H, m), 7.57-7.54 (1H, m), 3.79 (3H, s), 2.95 (2H, q), 1.30 (3H, t).

Present Compound 242

¹H-NMR (CDCl₃) δ: 8.80-8.78 (1H, m), 8.59-8.57 (1H, m), 8.36-8.34 (1H, m), 7.99-7.96 (1H, m), 7.78 (1H, d), 3.96 (3H, s), 3.57-3.46 (1H, m), 3.10-3.00 (1H, m), 1.37 (3H, t).

Present Compound 243

¹H-NMR (CDCl₃) δ: 8.79-8.77 (1H, m), 8.53-8.51 (1H, m), 8.32-8.30 (1H, m), 8.14-8.10 (1H, m), 7.74-7.71 (1H, m), 3.74 (3H, s), 3.49 (2H, q), 1.29 (3H, t).

Present Compound 246

¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.35-8.34 (1H, m), 7.66-7.65 (1H, m), 7.61-7.55 (2H, m), 3.80 (3H, s), 2.95 (2H, q), 1.28 (3H, t).

Present Compound 247

¹H-NMR (CDCl₃) δ: 8.80-8.78 (1H, m), 8.54-8.53 (1H, m), 8.35-8.34 (1H, m), 7.95-7.91 (1H, m), 7.79 (1H, d), 3.95 (3H, s), 3.52-3.41 (1H, m), 3.09-2.99 (1H, m), 1.33 (3H, t).

Present Compound 248

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.47-8.46 (1H, m), 8.31-8.30 (1H, m), 8.10-8.07 (1H, m), 7.76 (1H, d), 3.76 (3H, s), 3.48 (2H, q), 1.28 (3H, t).

Present Compound 249

¹H-NMR (CDCl₃) δ: 10.12 (1H, s), 8.75-8.74 (1H, m), 8.36-8.34 (1H, m), 7.97-7.96 (1H, m), 7.83-7.81 (1H, m), 7.64 (1H, d), 3.80 (3H, s), 3.00 (2H, q), 1.30 (3H, t).

Present Compound 250

¹H-NMR (CDCl₃) δ: 8.74-8.71 (1H, m), 8.35-8.33 (1H, m), 7.72-7.64 (3H, m), 7.59-7.42 (5H, m), 3.83 (3H, s), 2.92 (2H, q), 1.27 (3H, t).

Present Compound 255

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.19 (1H, d), 7.53-7.42 (3H, m), 7.38-7.29 (1H, m), 3.73 (3H, s), 2.97-2.83 (4H, m), 1.33-1.19 (6H, m).

Present Compound 256

¹H-NMR (CDCl₃) δ: 8.96 (1H, d), 8.54 (1H, d), 8.28-8.18 (1H, m), 7.91-7.80 (2H, m), 7.63-7.55 (1H, m), 3.74 (3H, s), 3.43 (2H, q), 3.24 (2H, q), 1.38 (3H, t), 1.26 (3H, t).

Present Compound 257

¹H-NMR (CDCl₃) δ: 8.53 (1H, d), 8.23 (1H, d), 7.54-7.42 (3H, m), 7.38-7.29 (1H, m), 3.74 (3H, s), 3.33-3.22 (1H, m), 2.87 (2H, q), 1.30 (6H, d), 1.24 (3H, t).

Present Compound 258

¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.51 (1H, d), 8.22 (1H, dd), 7.92-7.81 (2H, m), 7.62 (1H, dd), 3.75 (3H, s), 3.43 (2H, q), 3.36-3.26 (1H, m), 1.38 (6H, d), 1.26 (3H, t).

Present Compound 259

¹H-NMR (CDCl₃) δ: 8.64-8.58 (1H, m), 8.33-8.29 (1H, m), 7.53-7.30 (4H, m), 3.75-3.73 (3H, m), 3.45-3.38 (2H, m), 2.89-2.82 (2H, m), 1.27-1.21 (3H, m).

Present Compound 260

¹H-NMR (CDCl₃) δ: 9.01 (1H, d), 8.59 (1H, d), 8.25-8.21 (1H, m), 7.91-7.82 (2H, m), 7.63-7.58 (1H, m), 4.07 (2H, q), 3.75 (3H, s), 3.41 (2H, q), 1.26 (3H, t).

Present Compound 261

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 8.18 (1H, d), 7.53-7.41 (3H, m), 7.38-7.28 (1H, m), 5.95-5.81 (1H, m), 5.06-4.92 (2H, m), 3.73 (3H, s), 3.51 (2H, d), 2.86 (2H, q), 1.23 (3H, t).

Present Compound 262

¹H-NMR (CDCl₃) δ: 8.65-8.60 (1H, m), 8.40-8.35 (1H, m), 7.55-7.48 (2H, m), 7.47-7.41 (1H, m), 7.37-7.31 (1H, m), 3.76 (3H, s), 2.92-2.83 (2H, m), 1.27-1.18 (3H, m).

Present Compound 263

¹H-NMR (CDCl₃) δ: 8.64 (1H, d), 8.39 (1H, d), 7.56-7.49 (2H, m), 7.47-7.43 (1H, m), 7.38-7.32 (1H, m), 3.76 (3H, s), 2.89 (2H, q), 1.24 (3H, t).

Present Compound 264

¹H-NMR (CDCl₃) δ: 8.63 (1H, d), 8.37 (1H, d), 7.56-7.42 (3H, m), 7.38-7.32 (1H, m), 3.76 (3H, s), 2.88 (2H, q), 1.24 (3H, t).

Present Compound 272

¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.37 (1H, d), 8.26 (1H, dd), 7.83 (1H, td), 7.70 (1H, td), 7.61 (1H, dd), 3.88 (3H, s), 3.40-3.35 (1H, m), 3.01-2.95 (1H, m), 1.31 (3H, t).

Present Compound 273

¹H-NMR (CDCl₃) δ: 8.66 (1H, d), 8.34 (1H, d), 8.24-8.22 (1H, m), 7.89-7.78 (2H, m), 7.59-7.56 (1H, m), 3.71 (3H, s), 3.43 (2H, q), 1.25 (3H, t).

Present Compound 274

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.37 (1H, d), 8.26 (1H, dd), 7.83 (1H, td), 7.70 (1H, td), 7.61 (1H, dd), 3.89 (3H, s), 3.43-3.32 (1H, m), 3.04-2.93 (1H, m), 1.31 (3H, t).

Present Compound 275

¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.35 (1H, d), 8.23 (1H, dd), 7.89-7.77 (2H, m), 7.57 (1H, dd), 3.71 (3H, s), 3.43 (2H, q), 1.25 (3H, t).

Present Compound 276

¹H-NMR (CDCl₃) δ: 8.56 (1H, d), 8.27 (1H, d), 7.53-7.41 (3H, m), 7.39-7.25 (1H, m), 3.74 (3H, s), 2.89 (2H, q), 1.33 (9H, s), 1.24 (3H, t).

Present Compound 277

¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.52 (1H, d), 8.25-8.20 (1H, m), 7.89-7.84 (2H, m), 7.63-7.58 (1H, m), 3.75 (3H, s), 3.41 (2H, q), 1.43 (9H, s), 1.26 (3H, t).

Present Compound 278

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.24 (1H, d), 7.68-7.66 (1H, m), 7.60-7.54 (2H, m), 3.73 (3H, s), 2.94 (2H, q), 1.28 (3H, t).

Present Compound 279

¹H-NMR (CDCl₃) δ: 8.56-8.54 (2H, m), 8.23 (1H, d), 7.95-7.91 (1H, m), 7.77-7.74 (1H, m), 3.88 (3H, s), 3.50-3.40 (1H, m), 3.04-2.94 (1H, m), 1.34 (3H, t).

Present Compound 280

¹H-NMR (CDCl₃) δ: 8.53 (1H, d), 8.49-8.48 (1H, m), 8.19 (1H, d), 8.10-8.07 (1H, m), 7.74-7.71 (1H, m), 3.68 (3H, s), 3.48 (2H, q), 1.28 (3H, t).

Present Compound 281

¹H-NMR (CDCl₃) δ: 8.50 (1H, d), 8.20 (1H, d), 7.51-7.48 (2H, m), 7.46-7.43 (1H, m), 7.37-7.31 (1H, m), 5.96 (1H, t), 4.97 (2H, d), 3.73 (3H, s), 2.90-2.83 (2H, m), 1.23 (3H, t).

Present Compound 282

¹H-NMR (CDCl₃) δ: 8.99 (1H, d), 8.54 (1H, d), 8.26-8.20 (1H, m), 7.88-7.80 (2H, m), 7.58-7.11 (1H, m), 6.36 (1H, t), 5.53 (2H, d), 3.76-3.68 (3H, m), 3.46-3.35 (2H, m), 1.30-1.21 (3H, m).

Present Compound 283

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 8.51 (1H, d), 8.25-8.22 (1H, m), 7.88-7.81 (2H, m), 7.59-7.57 (1H, m), 5.95-5.84 (1H, m), 5.42 (1H, d), 5.23 (1H, dd), 3.93 (2H, d), 3.73 (3H, s), 3.42 (2H, q), 1.26 (3H, t).

Present Compound 284

¹H-NMR (CDCl₃) δ: 8.26-8.15 (1H, m), 8.05-7.97 (1H, m), 7.87-7.74 (2H, m), 7.62-7.55 (1H, m), 7.40-7.32 (1H, m), 3.70-3.57 (6H, m), 3.54-3.42 (2H, m), 1.30-1.19 (3H, m).

Present Compound 285

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.37-8.35 (1H, m), 8.28-8.27 (1H, m), 8.18-8.14 (1H, m), 7.65-7.62 (1H, m), 3.81 (3H, s), 3.04 (2H, q), 1.34 (3H, t).

Present Compound 286

¹H-NMR (CDCl₃) δ: 9.13-9.11 (1H, m), 8.81-8.79 (1H, m), 8.54-8.51 (1H, m), 8.37-8.34 (1H, m), 7.87 (1H, d), 3.98 (3H, s), 3.60-3.49 (1H, m), 3.13-3.02 (1H, m), 1.40 (3H, t).

Present Compound 287

¹H-NMR (CDCl₃) δ: 9.08-9.05 (1H, m), 8.80-8.77 (1H, m), 8.68 (1H, dd), 8.34-8.31 (1H, m), 7.81 (1H, d), 3.75 (3H, s), 3.52 (2H, q), 1.32 (3H, t).

Present Compound 289

¹H-NMR (CDCl₃) δ: 8.19 (1H, dd), 8.01 (1H, d), 7.83-7.73 (2H, m), 7.55 (1H, dd), 7.35 (1H, d), 3.61 (3H, s), 3.46 (2H, q), 1.23 (3H, t).

Present Compound 290

¹H-NMR (CDCl₃) δ: 8.51 (1H, d), 8.21 (1H, dd), 8.07 (1H, d), 7.90-7.81 (2H, m), 7.59 (1H, dd), 3.69 (3H, s), 3.50-3.42 (5H, m), 1.25 (3H, t).

Present Compound 291

¹H-NMR (CDCl₃) δ: 8.21 (1H, dd), 8.16 (1H, d), 7.83-7.72 (2H, m), 7.55 (1H, dd), 7.40 (1H, d), 3.63 (3H, s), 3.48 (2H, q), 3.01 (6H, s), 1.24 (3H, t).

Present Compound 292

¹H-NMR (CDCl₃) δ: 8.69-8.68 (1H, m), 8.33-8.31 (1H, m), 7.70-7.68 (1H, m), 7.62-7.55 (2H, m), 3.79 (3H, s), 2.97 (2H, q), 1.29 (3H, t).

Present Compound 293

¹H-NMR (CDCl₃) δ: 8.86 (1H, d), 8.56 (1H, d), 7.96 (1H, d), 7.48 (1H, d), 7.32 (1H, dd), 3.02 (2H, t), 1.37 (3H, d).

Present Compound 294

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 8.52 (1H, d), 8.25 (1H, d), 7.78 (1H, dd), 7.67 (1H, d), 3.76 (2H, q), 1.40 (3H, t).

Present Compound 295

¹H-NMR (CDCl₃) δ: 8.74 (1H, s), 8.59 (1H, d), 7.56-7.49 (2H, m), 7.41 (1H, dd), 7.37-7.31 (1H, m), 6.84 (1H, brs), 3.75 (3H, s), 2.88 (2H, q), 1.23 (3H, t).

Present Compound 296

¹H-NMR (CDCl₃) δ: 8.89 (1H, d), 8.56 (1H, d), 7.56-7.42 (3H, m), 7.39-7.33 (1H, m), 3.77 (3H, s), 2.89 (2H, q), 1.25 (3H, t).

Present Compound 297

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 8.53 (1H, d), 8.26 (1H, dd), 7.84 (1H, td), 7.71 (1H, td), 7.60 (1H, dd), 3.89 (3H, s), 3.42-3.32 (1H, m), 3.05-2.96 (1H, m), 1.31 (3H, t).

Present Compound 298

¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.50 (1H, d), 8.23 (1H, dd), 7.87-7.80 (2H, m), 7.56 (1H, dd), 3.71 (3H, s), 3.45 (2H, q), 1.26 (3H, t).

Present Compound 299

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.51-8.49 (1H, m), 8.29-8.27 (1H, m), 8.13-8.09 (1H, m), 7.74-7.71 (1H, m), 3.74 (3H, s), 3.49 (2H, q), 1.29 (3H, t).

Present Compound 300

¹H-NMR (CDCl₃) δ: 8.60 (1H, d), 8.39 (1H, d), 7.65-7.64 (1H, m), 7.58-7.51 (2H, m), 3.70 (3H, s), 2.91 (2H, q), 1.25 (3H, t).

Present Compound 303

¹H-NMR (CDCl₃) δ: 8.09 (1H, s), 7.52 (1H, d), 7.46-7.35 (3H, m), 7.25 (1H, t), 7.12 (1H, d), 3.56 (3H, s), 2.78 (2H, q), 1.17 (3H, t).

Present Compound 307

¹H-NMR (CDCl₃) δ: 8.65 (1H, d), 8.49-8.47 (1H, m), 8.37 (1H, d), 8.10-8.06 (1H, m), 7.74-7.71 (1H, m), 3.67 (3H, s), 3.47 (2H, q), 1.28 (3H, t).

Present Compound 308

¹H-NMR (CDCl₃) δ: 8.09 (1H, s), 7.59-7.42 (5H, m), 7.37-7.31 (1H, m), 3.69 (3H, s), 2.85 (2H, q), 1.23 (3H, t).

Present Compound 309

¹H-NMR (CDCl₃) δ: 8.22 (1H, d), 8.07 (1H, s), 7.80 (1H, t), 7.67 (1H, t), 7.62-7.52 (3H, m), 3.79 (3H, s), 3.37-3.26 (1H, m), 3.01-2.89 (1H, m), 1.27 (3H, t).

Present Compound 310

¹H-NMR (CDCl₃) δ: 8.20-8.18 (1H, m), 8.06 (1H, s), 7.82-7.74 (2H, m), 7.59-7.52 (3H, m), 3.61 (3H, s), 3.43 (2H, brs), 1.22 (3H, t).

Present Compound 311

¹H-NMR (CDCl₃) δ: 7.83 (1H, d), 7.69 (1H, d), 7.60 (1H, dd), 7.54-7.49 (1H, m), 7.48-7.42 (1H, m), 7.41-7.35 (1H, m), 6.69 (1H, d), 3.00 (2H, q), 2.93 (3H, s), 1.32 (3H, t).

Present Compound 312

¹H-NMR (CDCl₃) δ: 8.25-8.19 (2H, m), 7.83-7.78 (2H, m), 7.68 (1H, t), 7.55 (1H, d), 7.47 (1H, d), 3.79 (3H, s), 3.36-3.26 (1H, m), 3.00-2.90 (1H, m), 1.27 (3H, t).

Present Compound 313

¹H-NMR (CDCl₃) δ: 8.23-8.20 (2H, m), 7.85-7.76 (3H, m), 7.57-7.53 (1H, m), 7.46 (1H, d), 3.62 (3H, s), 3.39 (2H, brs), 1.24 (3H, t).

Present Compound 317

¹H-NMR (CDCl₃) δ: 8.65-8.64 (1H, m), 8.29-8.28 (1H, m), 7.35-7.31 (2H, m), 7.18-7.15 (1H, m), 3.76 (3H, s), 2.86 (2H, q), 2.46 (3H, s), 1.23 (3H, t).

Present Compound 318

¹H-NMR (CDCl₃) δ: 8.69-8.68 (1H, m), 8.28-8.26 (1H, m), 8.07-8.05 (1H, m), 7.50-7.48 (2H, m), 3.89 (3H, s), 3.44-3.33 (1H, m), 3.01-2.92 (1H, m), 2.58 (3H, s), 1.32 (3H, t).

Present Compound 319

¹H-NMR (CDCl₃) δ: 8.68-8.66 (1H, m), 8.25-8.23 (1H, m), 8.04-8.02 (1H, m), 7.65-7.61 (1H, m), 7.45-7.42 (1H, m), 3.71 (3H, s), 3.47-3.38 (2H, m), 2.59 (3H, s), 1.26 (3H, t).

Present Compound 320

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.68 (1H, d), 8.00-7.94 (1H, m), 7.55-7.51 (1H, m), 7.48-7.43 (1H, m), 7.36-7.31 (1H, m), 2.97 (2H, q), 1.33 (3H, t).

Present Compound 321

¹H-NMR (CDCl₃) δ: 8.81 (1H, d), 8.71 (1H, d), 8.08 (1H, d), 7.72 (1H, s), 7.56 (1H, d), 3.03 (2H, q), 1.37 (3H, t).

Present Compound 322

¹H-NMR (CDCl₃) δ: 8.81 (1H, d), 8.55 (1H, d), 8.07-8.00 (1H, m), 7.59-7.53 (1H, m), 7.52-7.45 (1H, m), 7.41-7.33 (1H, m), 2.99 (2H, q), 1.35 (3H, t).

Present Compound 323

¹H-NMR (CDCl₃) δ: 8.85 (1H, d), 8.59 (1H, d), 8.15 (1H, d), 7.75 (1H, s), 7.59 (1H, d), 3.05 (2H, q), 1.38 (3H, t).

Present Compound 324

¹H-NMR (CDCl₃) δ: 8.87 (1H, d), 8.50 (1H, d), 8.28-8.22 (1H, m), 7.85-7.76 (2H, m), 7.74-7.70 (1H, m), 3.74 (2H, q), 1.37 (3H, t).

Present Compound 325

¹H-NMR (CDCl₃) δ: 8.90 (1H, s), 8.57-8.49 (2H, m), 8.07 (1H, d), 7.88 (1H, d), 3.77 (2H, q), 1.40 (3H, t).

Present Compound 326

¹H-NMR (CDCl₃) δ: 8.93 (1H, d), 8.61 (1H, d), 7.45-7.34 (3H, m), 2.91 (2H, q), 1.27 (3H, t).

Present Compound 327

¹H-NMR (CDCl₃) δ: 8.95 (1H, d), 8.55 (1H, d), 8.14 (1H, dd), 7.86 (1H, dd), 7.73 (1H, t), 3.40 (2H, q), 1.28 (3H, t).

Present Compound 330

¹H-NMR (CDCl₃) δ: 8.74-8.73 (1H, m), 8.28-8.27 (1H, m), 8.22 (1H, d), 7.82 (1H, dd), 7.51 (1H, d), 6.86 (1H, dd), 6.03 (1H, d), 5.58 (1H, d), 3.72 (3H, s), 3.44 (2H, q), 1.27 (3H, t).

Present Compound 331

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.28-8.26 (1H, m), 8.05-8.03 (1H, m), 7.67-7.64 (1H, m), 7.46 (1H, d), 3.71 (3H, s), 3.41 (2H, q), 2.88 (2H, q), 1.37 (3H, t), 1.26 (3H, t).

Present Compound 332

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.46-8.44 (1H, m), 8.31-8.30 (1H, m), 8.09-8.05 (1H, m), 7.76 (1H, d), 3.75 (3H, s), 3.48 (2H, q), 1.27 (3H, t).

Present Compound 334

¹H-NMR (CDCl₃) δ: 8.89 (1H, d), 8.46 (1H, d), 8.27 (1H, dd), 7.85 (1H, td), 7.71 (1H, td), 7.62 (1H, dd), 3.92 (3H, s), 3.45-3.34 (1H, m), 3.04-2.94 (1H, m), 2.18 (6H, s), 1.32 (3H, t).

Present Compound 335

¹H-NMR (CDCl₃) δ: 8.87 (1H, d), 8.44 (1H, d), 8.26-8.19 (1H, m), 7.93-7.81 (2H, m), 7.64-7.60 (1H, m), 3.74 (3H, s), 3.43 (2H, q), 2.80 (6H, s), 1.26 (3H, t).

Present Compound 337

¹H-NMR (CDCl₃) δ: 9.26 (1H, s), 7.80 (1H, s), 7.43-7.36 (1H, m), 7.34-7.30 (1H, m), 7.27-7.21 (2H, m), 7.17 (1H, td), 3.66 (3H, s), 2.77 (2H, q), 2.12 (3H, s), 1.15 (3H, t).

Present Compound 338

¹H-NMR (CDCl₃) δ: 7.82-7.80 (1H, m), 7.50-7.43 (3H, m), 7.37-7.30 (1H, m), 7.19 (1H, s), 3.93 (3H, s), 2.87-2.82 (8H, m), 1.22 (3H, t).

Present Compound 339

¹H-NMR (CDCl₃) δ: 7.65 (1H, s), 7.60-7.53 (3H, m), 6.82 (1H, s), 4.01 (2H, brs), 3.94 (3H, s), 2.92 (2H, q), 1.27 (3H, t).

Present Compound 340

¹H-NMR (CDCl₃) δ: 7.82 (1H, s), 7.67 (1H, s), 7.61-7.53 (2H, m), 7.23 (1H, s), 3.96 (3H, s), 2.93 (2H, q), 2.86 (6H, s), 1.28 (3H, t).

Present Compound 347

¹H-NMR (CDCl₃) δ: 8.58 (1H, s), 7.56-7.29 (5H, m), 3.73 (3H, s), 2.88 (2H, q), 1.24 (3H, t).

Present Compound 348

¹H-NMR (CDCl₃) δ: 8.61 (1H, s), 8.28 (1H, dd), 7.81 (1H, td), 7.68 (1H, td), 7.62 (1H, dd), 7.27 (1H, t), 3.91 (3H, s), 3.68-3.58 (1H, m), 3.12-3.02 (1H, m), 1.37 (3H, t).

Present Compound 349

¹H-NMR (CDCl₃) δ: 8.59 (1H, s), 8.21 (1H, dd), 7.86-7.77 (2H, m), 7.60 (1H, dd), 7.27 (1H, t), 3.71 (3H, s), 3.54 (2H, q), 1.27 (3H, t).

Present Compound 350

¹H-NMR (CDCl₃) δ: 8.46 (1H, s), 7.51-7.32 (4H, m), 3.86-3.71 (1H, m), 3.68 (3H, s), 2.86 (2H, q), 1.61 (3H, s), 1.59 (3H, s), 1.22 (3H, t).

Present Compound 352

¹H-NMR (CDCl₃) δ: 8.69 (1H, s), 8.33 (1H, s), 8.25 (1H, dd), 8.21 (1H, dd), 7.73-7.58 (2H, m), 3.47-3.36 (1H, m), 3.13-3.01 (1H, m), 1.57-0.71 (3H, m).

Present Compound 355

¹H-NMR (CDCl₃) δ: 8.76 (1H, d), 8.51 (1H, d), 8.29 (1H, d), 8.10 (1H, dd), 7.74 (1H, d), 4.22 (2H, q), 3.55 (2H, q), 1.42 (3H, t), 1.30 (3H, t).

Present Compound 356

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.48 (1H, s), 8.31 (1H, d), 8.05 (1H, d), 7.73 (1H, d), 6.02-5.90 (1H, m), 5.19 (1H, d), 4.96 (1H, d), 4.79 (2H, s), 3.51 (2H, q), 1.29 (3H, t).

Present Compound 357

¹H-NMR (CDCl₃) δ: 8.81 (1H, d), 8.49 (1H, s), 8.33 (1H, d), 8.11 (1H, d), 7.94 (1H, d), 4.95 (2H, brs), 3.46 (2H, q), 2.34-2.31 (1H, m), 1.29 (3H, t).

Present Compound 358

¹H-NMR (CDCl₃) δ: 8.83 (1H, d), 8.50 (1H, d), 8.37 (1H, d), 8.18 (1H, dd), 7.93 (1H, d), 5.10 (2H, brs), 3.35 (2H, q), 1.27 (3H, t).

Present Compound 359

¹H-NMR (CDCl₃) δ: 8.98 (1H, d), 8.50 (1H, d), 8.21-8.17 (2H, m), 7.89 (1H, d), 4.97 (1H, brs), 4.85 (1H, brs), 3.47 (1H, brs), 3.34 (1H, brs), 1.28-1.20 (3H, m).

Present Compound 360

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.47 (1H, d), 8.32 (1H, d), 8.08 (1H, dd), 7.90 (1H, d), 5.53 (2H, s), 3.67 (2H, q), 3.58 (2H, q), 1.31 (3H, t), 1.18 (3H, t).

Present Compound 361

¹H-NMR (CDCl₃) δ: 8.91 (1H, d), 8.48 (1H, d), 8.21 (1H, d), 8.09 (1H, dd), 7.81 (1H, d), 5.36 (2H, s), 3.60-3.49 (4H, m), 1.28 (3H, t), 1.19 (3H, t).

Present Compound 362

¹H-NMR (CDCl₃) δ: 8.76 (1H, d), 8.47 (1H, d), 8.31 (1H, d), 8.10 (1H, dd), 7.98 (1H, d), 5.23 (2H, brs), 3.45 (2H, q), 2.26 (3H, s), 1.28 (3H, t).

Present Compound 363

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.50 (1H, d), 8.29 (1H, d), 8.09 (1H, dd), 7.74 (1H, d), 4.12 (2H, q), 3.53 (2H, q), 1.89-1.79 (2H, m), 1.29 (3H, t), 0.90 (3H, t).

Present Compound 364

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.51 (1H, d), 8.29 (1H, d), 8.09 (1H, dd), 7.74 (1H, d), 4.17-4.10 (2H, m), 3.53 (2H, q), 1.82-1.75 (2H, m), 1.34-1.24 (5H, m), 0.86 (3H, t).

Present Compound 365

¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.46 (1H, d), 8.33 (1H, d), 8.05 (1H, dd), 7.87 (1H, d), 4.91 (2H, brs), 3.77 (3H, s), 3.41 (2H, q), 1.27 (3H, t).

Present Compound 366

¹H-NMR (CDCl₃) δ: 8.92 (1H, d), 8.47 (1H, d), 8.07 (1H, dd), 7.96 (1H, d), 7.83 (1H, d), 4.82 (1H, brs), 4.69 (1H, brs), 3.81 (3H, s), 3.54 (1H, brs), 3.40 (1H, brs), 1.26 (3H, t).

Present Compound 367

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.50 (1H, d), 8.32 (1H, d), 8.11 (1H, dd), 7.73 (1H, d), 6.12 (1H, t), 4.92 (2H, d), 3.48 (2H, q), 1.29 (3H, t).

Present Compound 368

¹H-NMR (CDCl₃) δ: 8.76 (1H, d), 8.42 (1H, d), 8.21 (1H, d), 7.99 (1H, dd), 7.67 (1H, d), 3.60-3.50 (1H, m), 3.40-3.30 (1H, m), 1.70 (9H, s), 1.28 (3H, t).

Present Compound 369

¹H-NMR (CDCl₃) δ: 8.13 (1H, s), 7.67 (1H, s), 7.62 (1H, d), 7.59-7.57 (2H, m), 7.52 (1H, d), 3.70 (3H, s), 2.92 (2H, q), 1.27 (3H, t).

Present Compound 370

¹H-NMR (CDCl₃) δ: 8.53 (1H, s), 8.10 (1H, s), 7.93 (1H, d), 7.75 (1H, d), 7.65 (1H, d), 7.57 (1H, d), 3.85 (3H, s), 3.52-3.41 (1H, m), 3.05-2.95 (1H, m), 1.32 (3H, t).

Present Compound 371

¹H-NMR (CDCl₃) δ: 8.48 (1H, s), 8.10-8.05 (2H, m), 7.74 (1H, d), 7.62 (1H, d), 7.53 (1H, d), 3.63 (3H, s), 3.47 (2H, q), 1.25 (3H, t).

Present Compound 372

¹H-NMR (CDCl₃) δ: 8.77 (1H, d), 8.50 (1H, d), 8.30 (1H, d), 8.10 (1H, dd), 7.73 (1H, d), 3.74 (3H, s), 3.48 (2H, q), 1.29 (3H, t).

Present Compound 373

¹H-NMR (CDCl₃) δ: 8.83 (1H, d), 8.37-8.34 (2H, m), 8.04 (1H, dd), 7.72 (1H, d), 3.30-3.11 (2H, brm), 3.04 (3H, s), 1.24 (3H, t).

Present Compound 374

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.33-8.32 (1H, m), 7.48 (1H, d), 7.29-7.27 (1H, m), 7.21-7.17 (1H, m), 3.79 (3H, s), 2.92 (2H, q), 1.29 (3H, t).

Present Compound 375

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.33-8.31 (1H, m), 8.14-8.12 (1H, m), 7.68 (1H, d), 7.54-7.50 (1H, m), 3.93 (3H, s), 3.49-3.39 (1H, m), 3.06-2.96 (1H, m), 1.33 (3H, t).

Present Compound 376

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.30-8.28 (1H, m), 8.09-8.07 (1H, m), 7.70-7.66 (1H, m), 7.63 (1H, d), 3.74 (3H, s), 3.46 (2H, q), 1.28 (3H, t).

Present Compound 377

¹H-NMR (CDCl₃) δ: 8.78-8.77 (1H, m), 8.47-8.45 (1H, m), 8.32-8.30 (1H, m), 8.09-8.06 (1H, m), 7.76 (1H, d), 3.75 (3H, s), 3.48 (2H, q), 1.27 (3H, t).

Present Compound 378

¹H-NMR (CDCl₃) δ: 8.83-8.74 (3H, m), 8.54 (1H, dd), 8.31-8.29 (1H, m), 7.95-7.86 (2H, m), 7.68 (1H, d), 7.41-7.37 (1H, m), 3.75 (3H, s), 3.49 (2H, q), 1.30 (3H, t).

Present Compound 379

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.27-8.25 (1H, m), 7.43 (1H, d), 7.29 (1H, d), 6.99 (1H, dd), 4.28 (2H, brs), 3.70 (3H, s), 3.40 (2H, q), 1.26 (3H, t).

Present Compound 380

¹H-NMR (DMSO-D₆) δ: 11.94 (1H, brs), 8.86-8.84 (1H, m), 8.62-8.60 (1H, m), 8.53 (1H, d), 8.28 (1H, dd), 7.95 (1H, d), 3.64 (3H, s), 3.56 (2H, q), 1.14 (3H, t).

Present Compound 381

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.28-8.25 (1H, m), 8.07-8.05 (1H, m), 7.69-7.66 (1H, m), 7.47 (1H, d), 3.72 (3H, s), 3.41 (2H, q), 3.18-3.10 (1H, m), 1.37 (6H, d), 1.26 (3H, t).

Present Compound 382

¹H-NMR (CDCl₃) δ: 10.23 (1H, s), 8.78-8.76 (1H, m), 8.71 (1H, d), 8.35 (1H, dd), 8.31 (1H, d), 7.77 (1H, d), 3.74 (3H, s), 3.49 (2H, q), 1.30 (3H, t).

Present Compound 383

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.32-8.31 (1H, m), 7.55-7.49 (2H, m), 7.46-7.43 (1H, m), 7.38-7.33 (1H, m), 3.77 (3H, s), 2.84 (2H, t), 1.58-1.50 (2H, m), 1.39-1.29 (2H, m), 0.85 (3H, t).

Present Compound 384

¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.33-8.31 (1H, m), 7.66-7.63 (1H, m), 7.58-7.53 (1H, m), 7.49-7.41 (2H, m), 3.79 (3H, s), 3.66 (3H, s), 3.60 (2H, s).

Present Compound 385

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.34-8.32 (1H, m), 7.61-7.55 (2H, m), 7.52-7.44 (2H, m), 5.85 (1H, t), 3.77 (3H, s), 3.54 (2H, d).

Present Compound 386

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.32-8.31 (1H, m), 7.68-7.65 (1H, m), 7.59-7.54 (1H, m), 7.47 (1H, dd), 7.44-7.39 (1H, m), 3.78 (3H, s), 3.55 (2H, q), 1.75 (3H, t).

Present Compound 387

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.33-8.31 (1H, m), 7.87-7.84 (1H, m), 7.70-7.64 (1H, m), 7.63-7.58 (1H, m), 7.56 (1H, dd), 3.78 (3H, s), 3.61 (2H, s).

Present Compound 388

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.33-8.31 (1H, m), 7.57-7.48 (2H, m), 7.45-7.42 (1H, m), 7.37-7.32 (1H, m), 3.78 (3H, s), 2.82 (2H, s), 0.91 (9H, s).

Present Compound 389

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.33-8.31 (1H, m), 7.71-7.68 (1H, m), 7.63-7.58 (1H, m), 7.55-7.51 (2H, m), 3.76 (3H, s), 2.97 (2H, t), 2.52 (2H, t).

Present Compound 390

¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.33-8.31 (1H, m), 7.53-7.49 (2H, m), 7.46-7.42 (1H, m), 7.39-7.33 (1H, m), 3.76 (3H, s), 2.90 (2H, d), 2.50-2.37 (1H, m), 2.06-1.96 (2H, m), 1.87-1.71 (2H, m), 1.67-1.56 (2H, m).

Present Compound 391

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.35-8.34 (1H, m), 7.98-7.94 (1H, m), 7.71-7.67 (2H, m), 7.63-7.60 (1H, m), 3.78 (3H, s).

Present Compound 392

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.38-8.36 (1H, m), 8.31-8.29 (1H, m), 8.02-7.99 (1H, m), 7.69 (1H, d), 6.85 (1H, t), 3.73 (3H, s), 3.54-3.33 (2H, m), 1.28 (3H, t).

Present Compound 393

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.29-8.27 (1H, m), 8.21-8.19 (1H, m), 7.88-7.84 (1H, m), 7.56 (1H, d), 4.97-4.93 (2H, m), 3.71 (3H, s), 3.43 (2H, q), 1.26 (3H, t).

Present Compound 394

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.28-8.26 (1H, m), 8.25-8.22 (1H, m), 7.87-7.79 (2H, m), 7.58-7.55 (1H, m), 3.72 (3H, s), 3.43-3.37 (2H, m), 1.70-1.60 (2H, m), 1.45-1.35 (2H, m), 0.90 (3H, t).

Present Compound 395

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.33-8.29 (2H, m), 7.91-7.81 (2H, m), 7.60-7.57 (1H, m), 4.68 (2H, br s), 3.74 (3H, s), 3.72 (3H, s).

Present Compound 396

¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.29-8.27 (1H, m), 8.22-8.20 (1H, m), 7.92-7.82 (2H, m), 7.61-7.58 (1H, m), 5.92 (1H, t), 4.40 (2H, d), 3.73 (3H, s).

Present Compound 397

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.32-8.28 (2H, m), 7.89-7.80 (2H, m), 7.60-7.57 (1H, m), 4.35 (2H, br s), 3.73 (3H, s), 1.78 (3H, t).

Present Compound 398

¹H-NMR (CDCl₃) δ: 8.78-8.76 (1H, m), 8.43-8.40 (1H, m), 8.30-8.29 (1H, m), 8.00-7.95 (1H, m), 7.94-7.89 (1H, m), 7.68-7.65 (1H, m), 4.83 (2H, br s), 3.78 (3H, s).

Present Compound 399

¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.27-8.24 (2H, m), 7.83-7.80 (2H, m), 7.55-7.52 (1H, m), 3.71 (3H, s), 3.45 (2H, br s), 1.06 (9H, s).

Present Compound 400

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.33-8.32 (1H, m), 8.29-8.26 (1H, m), 7.95-7.90 (1H, m), 7.89-7.84 (1H, m), 7.64-7.61 (1H, m), 3.87 (2H, t), 3.73 (3H, s), 2.78 (2H, t).

Present Compound 401

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.32-8.30 (1H, m), 8.22-8.19 (1H, m), 7.86-7.78 (2H, m), 7.57-7.54 (1H, m), 3.70 (3H, s), 3.51 (2H, d), 2.75-2.63 (1H, m), 2.06-1.96 (2H, m), 1.94-1.70 (4H, m).

Present Compound 402

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.33-8.30 (2H, m), 8.03-7.98 (1H, m), 7.95-7.90 (1H, m), 7.70-7.68 (1H, m), 3.70 (3H, s).

Present Compound 403

¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.29-8.28 (1H, m), 8.21-8.19 (1H, m), 7.87-7.84 (1H, m), 7.63-7.60 (1H, m), 5.61 (2H, d), 3.72 (3H, s), 3.54-3.32 (2H, m), 1.27 (3H, t).

Present Compound 404

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.33-8.31 (1H, m), 7.61-7.50 (3H, m), 7.47-7.42 (1H, m), 6.42 (1H, dd), 5.37 (1H, d), 5.35 (1H, d), 3.79 (3H, s).

Present Compound 405

¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.35-8.33 (1H, m), 8.17-8.14 (1H, m), 7.82-7.77 (1H, m), 7.69-7.61 (2H, m), 7.42 (1H, dd), 6.17 (1H, d), 5.86 (1H, d), 3.97 (3H, s).

Present Compound 406

¹H-NMR (CDCl₃) δ: 8.75-8.74 (1H, m), 8.30-8.29 (1H, m), 8.25-8.22 (1H, m), 7.84-7.80 (2H, m), 7.57-7.54 (1H, m), 7.10 (1H, dd), 6.31 (1H, d), 6.03 (1H, d), 3.74 (3H, s).

Present Compound 407

¹H-NMR (CDCl₃) δ: 8.47 (1H, d), 8.04 (1H, dd), 7.84 (1H, d), 7.56 (1H, dd), 7.48 (1H, td), 7.37 (1H, td), 2.98 (2H, q), 1.34 (3H, t).

Present Compound 408

¹H-NMR (CDCl₃) δ: 8.44 (1H, d), 8.25 (1H, dd), 7.89 (1H, d), 7.84-7.71 (3H, m), 3.72 (2H, q), 1.37 (3H, t).

Present Compound 409

¹H-NMR (CDCl₃) δ: 8.68-8.66 (1H, m), 8.31-8.30 (1H, m), 7.48 (1H, d), 7.29-7.26 (1H, m), 7.21-7.17 (1H, m), 3.80 (3H, s), 2.93 (2H, q), 1.29 (3H, t).

Present Compound 410

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.30-8.29 (1H, m), 8.14-8.12 (1H, m), 7.68 (1H, d), 7.55-7.51 (1H, m), 3.93 (3H, s), 3.50-3.40 (1H, m), 3.08-2.98 (1H, m), 1.33 (3H, t).

Present Compound 411

¹H-NMR (CDCl₃) δ: 8.71-8.69 (1H, m), 8.27-8.26 (1H, m), 8.09-8.07 (1H, m), 7.70-7.66 (1H, m), 7.62 (1H, d), 3.74 (3H, s), 3.47 (2H, q), 1.28 (3H, t).

Present Compound 412

¹H-NMR (DMSO-D₆) δ: 7.88 (1H, s), 7.81 (1H, s), 7.73 (1H, d), 7.69 (1H, d), 7.39 (1H, s), 3.84 (3H, s), 3.09 (2H, q), 2.84 (3H, s), 1.19 (3H, t).

Present Compound 413

¹H-NMR (CDCl₃) δ: 8.50 (1H, s), 7.94-7.89 (2H, m), 7.69 (1H, d), 7.35 (1H, s), 3.99 (3H, s), 3.42-3.32 (1H, m), 3.01-2.90 (1H, m), 2.85 (3H, s), 1.28 (3H, t).

Present Compound 414

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 8.07 (1H, dd), 7.88 (1H, s), 7.72 (1H, d), 7.32 (1H, s), 3.82 (3H, s), 3.45 (2H, br s), 2.82 (3H, s), 1.26 (3H, t).

Present Compound 415

¹H-NMR (DMSO-D₆) δ: 8.13 (1H, d), 7.96 (1H, d), 7.82 (1H, s), 7.77-7.71 (2H, m), 3.65 (3H, s), 3.09 (2H, q), 1.18 (3H, t).

Present Compound 416

¹H-NMR (CDCl₃) δ: 8.52 (1H, d), 8.06 (1H, d), 7.93 (1H, dd), 7.72 (1H, d), 7.28 (1H, d), 3.80 (3H, s), 3.49-3.39 (1H, m), 3.05-2.95 (1H, m), 1.33 (3H, t).

Present Compound 417

¹H-NMR (CDCl₃) δ: 8.48 (1H, d), 8.09 (1H, dd), 8.02 (1H, d), 7.74 (1H, d), 7.25 (1H, d), 3.60 (3H, s), 3.45 (2H, q), 1.26 (3H, t).

Present Compound 418

¹H-NMR (CDCl₃) δ: 8.11 (1H, s), 7.67 (1H, s), 7.61-7.56 (3H, m), 7.53 (1H, d), 3.70 (3H, s), 2.93 (2H, q), 1.28 (3H, t).

Present Compound 419

¹H-NMR (CDCl₃) δ: 8.53 (1H, d), 8.09 (1H, s), 7.93 (1H, dd), 7.74 (1H, d), 7.64 (1H, d), 7.59 (1H, d), 3.85 (3H, s), 3.51-3.40 (1H, m), 3.06-2.97 (1H, m), 1.32 (3H, t).

Present Compound 420

¹H-NMR (CDCl₃) δ: 8.49 (1H, d), 8.10-8.04 (2H, m), 7.73 (1H, d), 7.60 (1H, d), 7.55 (1H, d), 3.64 (3H, s), 3.47 (2H, q), 1.25 (3H, t).

Present Compound 421

¹H-NMR (CDCl₃) δ: 8.72-8.71 (1H, m), 8.32-8.31 (1H, m), 7.57-7.49 (2H, m), 7.47-7.44 (1H, m), 7.39-7.34 (1H, m), 3.78 (3H, s), 2.78 (2H, d), 0.99-0.89 (1H, m), 0.54-0.48 (2H, m), 0.18-0.14 (2H, m).

Present Compound 422

¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.34-8.31 (1H, m), 8.28-8.26 (1H, m), 7.85-7.80 (1H, m), 7.71-7.67 (1H, m), 7.61-7.58 (1H, m), 3.91 (3H, s), 3.27 (1H, dd), 3.04 (1H, dd), 1.33-1.22 (1H, m), 0.71-0.62 (2H, m), 0.43-0.31 (2H, m).

Present Compound 423

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.31-8.26 (2H, m), 7.88-7.79 (2H, m), 7.57-7.54 (1H, m), 3.72 (3H, s), 3.34 (2H, d), 1.05-0.94 (1H, m), 0.57-0.50 (2H, m), 0.26-0.20 (2H, m).

Present Compound 424

¹H-NMR (CDCl₃) δ: 8.30 (1H, d), 8.20 (1H, s), 7.78-7.67 (2H, m), 7.63 (1H, s), 7.52 (1H, d), 3.11 (2H, q), 1.47 (3H, t).

Present Compound 425

¹H-NMR (CDCl₃) δ: 8.53 (1H, s), 8.18-8.12 (2H, m), 8.08 (1H, d), 7.77-7.72 (2H, m), 3.91 (2H, q), 1.44 (3H, t).

Present Compound 426

¹H-NMR (CDCl₃) δ: 8.12 (1H, s), 7.66 (1H, s), 7.62 (1H, dd), 7.57 (1H, br s), 7.52 (1H, d), 3.70 (3H, s), 2.92 (2H, q), 1.26 (3H, t).

Present Compound 427

¹H-NMR (CDCl₃) δ: 7.95 (1H, d), 7.64 (1H, s), 7.57-7.51 (3H, m), 4.03 (3H, s), 3.04 (2H, q), 2.93 (2H, q), 1.37 (3H, t), 1.29-1.20 (3H, m).

The productions of the intermediates of the present compound are shown in the following Reference Production Examples.

Reference Production Example 1

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (1.91 g), 2-fluorobenzaldehyde (1.86 g), sodium hydrogen sulfite (1.56 g), and DMF (10 ml) was stirred with heating under reflux at 153° C. for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.89 g of 2-(2-fluorophenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine (Compound (1E)-F1).

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¹H-NMR (CDCl₃) δ: 8.73-8.72 (1H, m), 8.33-8.32 (1H, m), 7.76-7.72 (1H, m), 7.64-7.58 (1H, m), 7.41-7.36 (1H, m), 7.32-7.27 (1H, m), 3.89 (3H, d)

Reference Production Example 2-a

To a mixture of 2-chloro-5-trifluoromethylpyridine (18.2) and N-methylpyrrolidone (100 ml), 40% of aqueous methylamine solution (23.3 g) was added, and stirred at room temperature for 3 hours. Water was poured thereinto, and extracted with ethyl acetate 3 times. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 17.3 g of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine.

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¹H-NMR (CDCl₃) δ: 8.34 (s, 1H), 7.60 (dd, 1H), 6.40 (d, 1H), 4.89 (brs, 1H), 2.97 (d, 3H)

Reference Production Example 2-b

To a mixture of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine (17.3 g) and sulfuric acid (100 ml), nitric acid (12.3 g) was added dropwise, and stirred with heating at 80° C. for 2 hours. The mixture was cooled to room temperature, and then the reaction mixture was poured into water. The precipitate was collected by filtration, washed with water, and dried under reduced pressure to give 18.8 g of N-methyl-(3-nitro-5-trifluoromethyl-pyridin-2-yl)-amine.

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¹H-NMR (CDCl₃) δ: 8.66-8.64 (m, 2H), 8.43 (brs, 1H), 3.23 (d, 3H)

Reference Production Example 2-c

A mixture of N-methyl-(3-nitro-5-trifluoromethyl-pyridin-2-yl)-amine (6.93 g), 5% of palladium-carbon (0.69 g), and ethanol was stirred under about 1 atm of hydrogen at room temperature for 10 hours. The reaction mixture was filtered through Celite®, and then the filtrate was concentrated under reduced pressure to give 5.02 g of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-1).

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¹H-NMR (CDCl₃) δ: 8.04 (s, 1H), 6.98 (d, 1H), 4.56 (brs, 1H), 3.25 (brs, 2H), 3.06 (d, 3H)

The compound of Reference Production Example 2-c can also be produced by the following production method.

Reference Production Example 2-d

To a mixture of N-methyl-(5-trifluoromethyl-pyridin-2-yl)-amine (3.48 g) and DMF (20 ml), N-bromosuccinimide (4.27 g) was added, and stirred at room temperature for 1 hour. Into the reaction mixture, saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 4.8 g of N-methyl-(3-bromo-5-trifluoromethyl-pyridin-2-yl)-amine.

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¹H-NMR (CDCl₃) δ: 3.08 (3H, d), 5.40 (1H, brs), 7.78 (1H, d), 8.34 (1H, s).

Reference Production Example 2-e

To a pressure-resistant reaction container, N-methyl-(3-bromo-5-trifluoromethyl-pyridin-2-yl)-amine (0.51 g), copper (II) acetylacetone (0.11 g), acetylacetone (0.20 g), cesium carbonate (1.30 g), NMP (2 ml), and 28% of aqueous ammonia (1 ml) were added, and stirred at 120° C. for 7 hours, then at 130° C. for 3 hours. The mixture was allowed to cool to room temperature, and then saturated aqueous ammonium chloride solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.28 g of N²-methyl-5-trifluoromethylpyridin-2,3-diamin.

Reference Production Example 3-a

A mixture of 2-chloro-5-trifluoromethylpyridine (12 g), 70% of aqueous ethylamine solution (16 ml), and NMP (7 ml) was stirred with heating at 70° C. for 1 day. Into the reaction mixture cooled to room temperature, water was poured, and then the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried to give 6.3 g of N-ethyl-(5-trifluoromethylpyridin-2-yl)-amine.

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¹H-NMR (CDCl₃) δ: 8.25 (1H, s), 7.51 (1H, d), 6.31 (1H, d), 4.84 (1H, brs), 3.32-3.25 (2H, m), 1.27-1.11 (3H, m)

Reference Production Example 3-b

A mixture of N-methyl-(5-trifluoromethylpyridin-2-yl)-amine (1.0 g) and sulfuric acid (7 ml) was stirred with heating at 95° C., and then a mixture of fuming nitric acid (0.45 ml) and sulfuric acid (3 ml) were added thereto, and stirred with heating for 1 hour. The reaction mixture cooling to room temperature was poured into ice, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel chromatography to give 600 mg of N-ethyl-(3-nitro-5-trifluoromethylpyridin-2-yl)-amine.

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Reference Production Example 3-c

A mixture of iron powder (700 mg), acetic acid (60 μl), ethanol (5 ml), and water (3 ml) was stirred with heating at 70° C., and then a mixture of N-ethyl-(3-nitro-5-trifluoromethylpyridin-2-yl)-amine (490 mg) and ethanol (10 ml) was added dropwise. The mixture was stirred with heating at 70° C. for 3 hours. The reaction mixture cooled to room temperature was filtered through Celite®, and the resulting filtrate was concentrated under reduced pressure. The resulting residue was diluted with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.29 g of N²-ethyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-8).

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¹H-NMR (CDCl₃) δ: 8.01 (1H, d), 6.97 (1H, d), 3.51 (2H, q), 1.27 (3H, t)

Reference Production Example 4-a

The procedure was performed according to the method described in Reference Production Example 3-a using n-propylamine instead of 70% of aqueous ethylamine solution to give 10 g of N-propyl-(5-trifluoromethylpyridin-2-yl)-amine.

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Reference Production Example 4-b

A mixture of N-propyl-(5-trifluoromethylpyridin-2-yl)-amine (3.0 g) and sulfuric acid (20 ml) was stirred with heating at 95° C., and then a mixture of fuming nitric acid (1.3 ml) and sulfuric acid (10 ml) was added dropwise, and stirred with heating for 1 hour. The reaction mixture was poured into ice, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure.

To a mixture of the resulting residue, ethanol (12 ml) and water (8 ml), iron powder (2.5 g) and acetic acid (0.5 ml) were added, heated to 70° C., and stirred with heating for 2 hours. The reaction mixture cooled to room temperature was filtered through Celite®, and then the resulting filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.5 g of N²-propyl-5-trifluoromethylpyridin-2,3-diamine.

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Reference Production Example 4-c

A mixture of N-propyl-5-trifluoromethylpyridin-2,3-diamine (770 mg), 2-ethylsulfanyl-benzoic acid (700 mg), WSC (740 mg), and pyridine (20 ml) was stirred with heating at 95° C. for 7 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 422 mg of 2-ethylsulfanyl-N-(2-propylamino-5-trifluoromethylpyridin-3-yl)-benzamide (Compound (1B)-513).

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Reference Production Example 5-a

The procedure was performed according to the method described in Reference Production Example 3-b using 5-trifluoromethylpyridin-2-ol instead of N-methyl-(5-trifluoromethylpyridin-2-yl)-amine to give 3.3 g of 3-nitro-5-trifluoromethylpyridin-2-ol.

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¹H-NMR (DMSO-d₆) δ: 13.54 (1H, brs), 8.67 (1H, d), 8.46 (1H, d)

Reference Production Example 5-b

To a mixture of 3-nitro-5-trifluoromethylpyridin-2-ol (3.2 g) and DMF (1 drop), phosphorous oxychloride (8.2 ml) was added at room temperature. The mixture was heated to 105° C., and stirred with heating for 2 days. The reaction mixture was cooled to room temperature, and then the reaction mixture was poured into ice, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 2.5 g of 2-chloro-3-nitro-5-trifluoromethylpyridine.

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Reference Production Example 5-c

To a mixture of 2-chloro-3-nitro-5-trifluoromethylpyridine (1.5 g) and ethanol (15 ml), isopropylamine (1.8 ml) was added under ice-cooling, heated to room temperature, and stirred with heating for 3 hours. Into the reaction mixture, 2 mol/l of aqueous solution of hydrochloric acid was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure.

To the resulting residue, ethanol (30 ml), water (20 ml), ammonium chloride (0.7 g), iron powder (445 mg), and ammonium chloride (0.7 g) were sequentially added at room temperature. The mixture was heated to 70° C., and stirred with heating for 1 day. Into the reaction mixture cooled to room temperature, aqueous sodium hydroxide solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure to give 970 mg of N²-isopropyl-5-trifluoromethylpyridin-2,3-diamine (Compound (1F)-15).

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Reference Production Example 6

The procedure was performed according to the method described in Reference Production Example 5-c using cyclopropylamine instead of isopropylamine to give 750 mg of N²-cyclopropyl-5-trifluoromethylpyridin-2,3-diamine.

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Reference Production Example 7

The procedure was performed according to the method described in Reference Production Example 3-c using 5-trifluoromethyl-pyridin-2,3-diamine instead of N²-propyl-5-trifluoromethylpyridin-2,3-diamine to give 4.7 g of N-(2-amino-5-trifluoromethylpyridin-3-yl)-2-ethylsulfanyl-benzamide (Compound (1B)-512).

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¹H-NMR (DMSO-D₆) δ: 9.75 (1H, s), 8.17 (1H, s), 8.09 (1H, s), 7.64 (1H, d), 7.53-7.45 (2H, m), 7.34-7.28 (1H, m), 6.71 (2H, s), 2.97 (2H, q), 1.22 (3H, t)

Reference Production Example 8

A mixture of 5,N²-dimethylpyridin-2,3-diamine (1.13 g), 2-ethylsulfanylbenzoic acid (1.79 g), WSC (1.38 g), and pyridine (20 ml) was stirred with heating under reflux at 120° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.58 g of 2-ethylsulfanylphenyl-N-(5-methyl-2-methylaminopyridin-3-yl)-benzamide (Compound (1B)-514).

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¹H-NMR (CDCl₃) δ: 8.18 (1H, brs), 7.97-7.93 (1H, m), 7.85-7.80 (1H, m), 7.54-7.42 (3H, m), 7.39-7.33 (1H, m), 3.03-2.93 (5H, m), 1.32 (3H, t)

Reference Production Example 9

To a mixture of 5-iodo-3-nitropyridin-2-ylamine (1.0 g) and DMF (20 ml), 60% of sodium hydride (in oil, 180 mg) and methyl iodide (240 μl) were sequentially added under ice-cooling. The mixture was heated to room temperature, and stirred for 1 hour. Into the reaction mixture, water was poured, and then the precipitated solid was collected by filtration, and dried.

The obtained solid was dissolved in THF. The solution was added dropwise to a mixture of iron powder (633 mg), acetic acid (1 ml), ethanol (30 ml), and water (20 ml) with heating at 70° C. The mixture was stirred with heating at 70° C. for 3.5 hours. The reaction mixture cooled to room temperature was filtered through Celite®. The resulting filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 980 mg of 5-iodo-N²-methylpyridin-2,3-diamine (Compound (1F)-6).

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Reference Production Example 10-a

To a mixture of 5-trifluoromethylpyridin-2,3-diamine (1.2 g) and pyridine (20 ml), methyl chloroformate (0.63 ml) was added under ice-cooling. The mixture was heated to room temperature, stirred for 8 hours, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 628 mg of methyl (2-amino-5-trifluoromethylpyridin-3-yl)-carbamate.

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¹H-NMR (CDCl₃) δ: 8.65 (1H, brs), 8.18-7.99 (2H, m), 5.75 (2H, brs), 3.79 (3H, s)

Reference Production Example 10-b

To a mixture of methyl (2-amino-5-trifluoromethylpyridin-3-yl)-carbamate (100 mg) and THF (15 ml), lithium aluminum hydride (26 mg) was added under ice-cooling. The mixture was stirred for 15 minutes under ice-cooling, heated to 90° C., and stirred with heating for 1.5 hours. Into the reaction mixture cooled to room temperature, aqueous sodium hydroxide solution was poured, and extracted with tert-butyl methyl ether. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 77 mg of N³-methyl-5-trifluoromethylpyridin-2,3-diamine.

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Reference Production Example 11-a

To a mixture of methyl-(2-nitro-4-trifluoromethylphenyl)-amine (4.40 g) and DMF (20 ml), N-chlorosuccinimide (3.67 g) was added under ice-cooling, and stirred for 3 hours. The mixture was heated to room temperature, and allowed to stand. Water was poured thereinto under ice-cooling, and then the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried to give 3.96 g of (2-chloro-6-nitro-4-trifluoromethylphenyl)-methylamine.

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¹H-NMR (CDCl₃) δ: 8.19 (1H, d), 7.68 (1H, d), 7.17 (1H, brs), 3.19 (3H, d)

Reference Production Example 11-b

To a mixture of (2-chloro-6-nitro-4-trifluoromethylphenyl)-methylamine (3.70 g) and ethanol (60 ml), Raney® nickel (slurry in water, 0.5 ml) was added, and stirred under about 1 atm of hydrogen at room temperature for 1.5 hours. The reaction mixture was filtered. The filtrate was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.95 g of 3-chloro-N²-methyl-5-trifluoromethylbenzene-1,2-diamine.

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¹H-NMR (CDCl₃) δ: 7.02 (1H, d), 6.82 (1H, d), 4.09 (2H, brs), 3.49 (1H, brs), 2.74 (3H, d)

Reference Production Example 12

A mixture of 2-amino-4-trifluoromethylphenol (1.00 g), 2-methylsulfanylbenzoic acid (0.95 g), WSC (1.41 g), and pyridine (10 ml) was stirred with heating at 80° C. for 2.5 hours. Into the reaction mixture cooled to room temperature, 1 mol/l of hydrochloric acid was poured, and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate solution, water, and saturated brine, sequentially, dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.33 g of N-(2-hydroxy-5-trifluoromethylphenyl)-2-methylsulfanyl-benzamide (Compound (1B)-515).

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¹H-NMR (DMSO-D₆) δ: 9.50 (1H, brs), 8.24 (1H, s), 7.61 (1H, d), 7.50 (1H, t), 7.42 (1H, d), 7.37 (1H, dd), 7.27 (1H, t), 7.06 (1H, d), 2.45 (3H, s)

Reference Production Example 13

To a mixture of 3-amino-5-trifluoromethylpyridin-2-ol (0.75 g) and THF (5 ml), 2-ethylsulfanylbenzoic acid hydrochloride (0.93 g) was added under ice-cooling, heated to room temperature, and stirred for 2 hours. After the mixture was allowed to stand overnight, the mixture was heated to 50° C., and stirred with heating for 6 hours. To the mixture, sodium hydrogen carbonate (0.35 g) was added, and stirred with heating for further 2.5 hours. After the mixture was allowed to stand, water was poured thereinto, and the precipitated solid was collected by filtration. The obtained solid was washed with water, and dried to give 1.37 g of 2-ethylsulfanyl-N-(2-hydroxy-5-trifluoromethylpyridin-3-yl)-benzamide (Compound (1B)-506).

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¹H-NMR (CDCl₃) δ: 11.68 (1H, brs), 9.35 (1H, brs), 8.87 (1H, d), 7.75-7.71 (1H, m), 7.49-7.43 (3H, m), 7.33-7.29 (1H, m), 2.99 (2H, q), 1.34 (3H, t)

Reference Production Example 14

To a mixture of 3-chloroanthranilic acid (3.43 g) and 1 mol/l of hydrochloric acid (20 ml), sodium nitrite (1.38 g) was added portionwise at room temperature, and stirred for 10 minutes. The reaction mixture was added dropwise to a mixture of potassium butylxanthogenate (5.65 g) and water (20 ml) at room temperature, and stirred for 1 hour. 3N aqueous sodium hydroxide solution (20 ml) and diethylsulfuric acid (2.9 ml) were added thereto, heated to 100° C., and stirred under reflux for 1 hour. To the reaction mixture cooled to room temperature, 12 mol/l of hydrochloric acid was added dropwise under ice-cooling until the reaction mixture reached pH 1-2. The precipitated solid was collected by filtration, and dried under reduced pressure.

To the obtained solid, 3N aqueous sodium hydroxide solution (10 ml), ethanol (10 ml), and ethyl iodide (6.86 g) were added, heated to 80° C., and stirred under reflux for 2 hours. To the reaction mixture cooled to room temperature, 12 mol/l of hydrochloric acid was added dropwise under ice-cooling until the reaction mixture reached pH 1-2, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.79 g of 3-chloro-2-ethylsulfanylbenzoic acid.

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¹H-NMR (CDCl₃) δ: 8.10-8.05 (1H, m), 7.68 (1H, dd), 7.43 (1H, t), 3.00 (2H, q), 1.26 (3H, t)

Reference Production Example 15

To a pressure-resistant reaction container, 3-amino-2-chloro-5-trifluoromethylpyridine (5 g), copper (II) acetylacetone (1.31 g), acetylacetone (2.50 g), cesium carbonate (16.25 g), NMP (20 ml), and 40% of aqueous methylamine solution (15 ml) were added, and stirred at 100° C. for 3 hours, at 120° C. for 3 hours, then at 140° C. for 5 hours. After the mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was poured thereinto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.09 g of N²-methyl-6-trifluoromethylpyridin-2,3-diamine.

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¹H-NMR (CDCl₃) δ: 3.04 (3H, s), 3.41 (2H, brs), 4.22 (1H, brs), 6.84 (1H, d), 6.91 (1H, d).

Reference Production Example 16-a

To a mixture of 3-amino-2-chloro-6-trifluoromethylpyridine (3.93 g) and chloroform (30 ml), pivaloyl chloride (2.65 g) and triethylamine (4.04 g) were added under ice-cooling, and stirred at room temperature for 2 hours, then at 60° C. for 2 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 6.59 g of N-(2-chloro-6-trifluoromethylpyridin-3-yl)-2,2-dimethylpropionamide.

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¹H-NMR (CDCl₃) δ: 1.36 (9H, s), 7.65 (1H, d), 8.17 (1H, brs), 8.97 (1H, d).

Reference Production Example 16-b

To a mixture of N-(2-chloro-6-trifluoromethylpyridin-3-yl)-2,2-dimethylpropionamide (6.59 g) and THF (30 ml), sodium hydride (60% in oily, 1 g) was added under ice-cooling, and stirred at room temperature for 30 minutes. The reaction mixture was ice-cooled, and then methyl iodide (10 g) was added, and stirred at room temperature for 4 hours. Into the reaction mixture, water was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. To the resulting residue, acetonitrile (40 ml), concentrated hydrochloric acid (40 ml), and isopropanol (40 ml) were added, and stirred at room temperature for 2 hours, at 60° C. for 2 hours, then at 80° C. for 2 hours. Into the reaction mixture cooled to room temperature, saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.60 g of (2-chloro-6-trifluoromethylpyridin-3-yl)-methylamine.

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¹H-NMR (CDCl₃) δ: 7.49 (1H, d), 6.89 (1H, d), 4.82 (1H, brs), 2.96 (3H, d).

Reference Production Example 16-c

To a pressure-resistant reaction container, (2-chloro-6-trifluoromethylpyridin-3-yl)-methylamine (2.60 g), copper (II) acetylacetone (0.64 g), acetylacetone (1.23 g), cesium carbonate (7.99 g), NMP (10 ml), and 28% of aqueous ammonia (7 ml) were added, and stirred at 140° C. for 8 hours. After the mixture was allowed to cool to room temperature, saturated aqueous ammonium chloride solution was poured thereinto, and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 2.09 g of N³-methyl-6-trifluoromethylpyridin-2,3-diamine.

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¹H-NMR (CDCl₃) δ: 2.89 (3H, d), 3.56 (1H, brs), 4.29 (2H, brs), 6.77 (1H, d), 7.13 (1H, d).

Reference Production Example 17

A mixture of 3-amino-5-(trifluoromethyl)pyridin-2-thiol (0.20 g), 2-ethylsulfanylbenzaldehyde (0.20 g), sodium hydrogen sulfite (0.13 g), copper (II) chloride (0.41 g), and DMF (2.5 ml) was stirred at 120° C. for 8 hours. After the reaction mixture was allowed to cool, water was added thereto, and ethyl acetate was poured. The mixture was filtered, and the resulting filtrate was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 0.18 g of 2-[2-fluoro-4-(trifluoromethyl)phenyl]-6-(trifluoromethyl)thiazolo[5,4-b]pyridine ((1E)-F57).

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¹H-NMR (CDCl₃) δ: 7.58 (1H, d), 7.64 (1H, d), 8.57-8.63 (2H, m), 8.92 (1H, s).

Reference Production Example 18

A mixture of N²-methyl-5-trifluoromethylpyridin-2,3-diamine (5.37 g), 2-fluoro-4-trifluorobenzaldehyde (6.92 g), sodium hydrogen sulfite (3.75 g), and DMF (30 ml) was stirred at 150° C. for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 7.83 g of 2-(2-fluoro-4-trifluoromethylphenyl)-3-methyl-6-trifluoromethyl-3H-imidazo[4,5-b]pyridine ((1E)-F6).

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¹H-NMR (CDCl₃) δ: 8.75 (1H, d), 8.35 (1H, d), 7.91 (1H, t), 7.67 (1H, d), 7.59 (1H, d), 3.92 (3H, d).

Reference Production Example 19-a

To a mixture of 2-chloro-5-iodppyridine (7.2 g), NMP (75 mL), and xylene (75 mL), pentafluorosodium propionate (28 g) and copper iodide (14 g) were added at room temperature, heated to 150° C., and stirred with heating for 5.5 hours. After the mixture was cooled to 80° C., to the mixture, 40% of aqueous methylamine solution (180 mL) was added in parts 4 every 2 hours, and stirred with heating for 8.5 hours. The mixture was ice-cooled to 0° C., and then 28% of aqueous ammonia and saturated aqueous sodium hydrogen carbonate solution were poured thereinto, and extracted with MTBE. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 4.6 g of methyl-(5-pentafluoroethyl-pyridine-2-yl)-amine.

methyl-(5-pentafluoroethyl-pyridine-2-yl)-amine

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¹H-NMR (CDCl₃) δ: 8.28 (1H, d), 7.56 (1H, dd), 6.41 (1H, d), 5.74 (1H, brs), 2.95 (3H, d).

Reference Production Example 19-b

To a mixture of methyl-(5-pentafluoroethyl-pyridine-2-yl)-amine (4.6 g) and acetonitrile (70 mL), N-bromosuccinimide (5.0 g) was added under ice-cooling, and stirred at room temperature for 8 hours. Into a mixture, saturated aqueous sodium thiosulfate solution and aqueous sodium hydrogen carbonate solution were poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 6.3 g of (3-bromo-5-pentafluoroethyl-pyridine-2-yl)-methyl-amine.

(3-bromo-5-pentafluoroethyl-pyridine-2-yl)-methyl-amine

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¹H-NMR (CDCl₃) δ: 8.29 (1H, d), 7.74 (1H, d), 5.45 (1H, brs), 3.09 (3H, d).

Reference Production Example 19-c

To an autoclave reactor, (3-bromo-5-pentafluoroethyl-pyridine-2-yl)-methyl-amine (2.0 g), acetylacetone copper(II) (86 mg), acetylacetone (263 mg), cesium carbonate (3.2 g), and NMP (13 mL) were added, and then 28% of aqueous ammonia (5 mL) was added under ice-cooling. After the reactor was sealed, the mixture was heated to 110° C., and stirred with heating for 15 hours. After the mixture was cooled to room temperature, the reaction mixture was diluted with water, and extracted with MTBE. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 623 mg of N²-methyl-5-pentafluoroethyl-2,3-diamine (Compound (1F)-2).

N²-methyl-5-pentafluoroethyl-2,3-diamine

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¹H-NMR (CDCl₃) δ: 7.99 (1H, d), 6.94 (1H, d), 4.64 (1H, brs), 3.30 (2H, brs), 3.06 (3H, d).

Reference Production Example 20-a

A mixture of 2-chloro-5-iodppyridine (23.9 g), thiobenzoic acid (14 ml), copper iodide (1.90 g), 1,10-phenanthroline (3.60 g), diisopropylethylamine (35 ml), and toluene (200 ml) was stirred at 110° C. for 4 hours. After the reaction mixture was cooled to room temperature, water was poured thereinto. The insoluble material was filtered through Celite®, and then the filtered material was washed with ethyl acetate, and the filtrate was extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 21.2 g of S-(6-chloropyridine-3-yl)thiobenzoate.

S-(6-chloropyridine-3-yl)thiobenzoate

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¹H-NMR (CDCl₃) δ: 8.43-8.42 (1H, m), 8.01-7.98 (2H, m), 7.79-7.76 (1H, m), 7.66-7.61 (1H, m), 7.52-7.47 (2H, m), 7.44-7.41 (1H, m).

Reference Production Example 20-b

A mixture of S-(6-chloropyridine-3-yl)thiobenzoate (21.2 g), potassium carbonate (17.6 g), and methanol (170 ml) was stirred at room temperature for 2 hours. The reaction mixture was filtered, and then the filtered material was washed with methanol, and filtrate was concentrated under reduced pressure. To the resulting crude, 1N aqueous sodium hydroxide solution (170 ml) was added, and then an aqueous solution of potassium ferricyanide (56.0 g) was added dropwise, and stirred at room temperature for 2 hours. The reaction mixture was extracted with methyl-tert-butyl ether. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 11.5 g of a compound of the following formula:

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¹H-NMR (CDCl₃) δ: 8.41 (2H, d), 7.74 (2H, dd), 7.29 (2H, d).

Reference Production Example 20-c

A mixture of a compound (11.5 g) of the following formula:

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and

DMF (133 ml) was cooled to −50° C., and bubbled with excessive amounts of CF₃I gas to dissolve the compound in DMF. To the mixture, tetrakis(dimethylamino)ethylenediamine (37.0 ml) was added dropwise at a rate that the internal temperature did not exceed −40° C. Then, the mixture was heated to −10° C. over 1 hour, and stirred at −10° C. for 2 hour. Into the reaction mixture, water was poured, heated to room temperature, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 7.25 g of 2-chloro-5-trifluoromethylsulfanylpyridine.

2-chloro-5-trifluoromethylsulfanylpyridine

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¹H-NMR (CDCl₃) δ: 8.62 (1H, d), 7.93 (1H, dd), 7.43 (1H, d).

Reference Production Example 20-d

To a mixture of 2-chloro-5-trifluoromethylsulfanylpyridine (1.71 g) and NMP (16 ml), 40% of aqueous methylamine solution (1.86 g) was added dropwise, and then the mixture was heated to 60° C., and stirred with heating for 2 hours. After the mixture was cooled to room temperature, potassium carbonate (1.66 g) was added thereto, and 40% of aqueous methylamine solution (1.86 g) was added dropwise. The mixture was heated to 60° C., and stirred with heating for further 2 hours. After the mixture was cooled to room temperature, water was poured, and extracted with ethyl acetate. The combined organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.52 g of methyl-(5-trifluoromethylsulfanylpyridine-2-yl)-amine.

methyl-(5-trifluoromethylsulfanylpyridine-2-yl)-amine

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¹H-NMR (CDCl₃) δ: 8.28 (1H, d), 7.63 (1H, dd), 6.41-6.38 (1H, m), 4.90 (1H, brs), 2.96 (3H, d,).

Reference Production Example 20-e

To a mixture of methyl-(5-trifluoromethylsulfanylpyridine-2-yl)-amine (1.52 g) and chloroform (24 mL), N-bromosuccinimide (1.43 g) was added, and stirred at room temperature for 1 hour. Into the reaction mixture, water was poured, and extracted with chloroform. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.96 g of (3-bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine.

(3-bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine

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¹H-NMR (CDCl₃) δ: 8.28 (1H, d), 7.83 (1H, d), 5.40 (1H, brs), 3.07 (3H, d).

Reference Production Example 20-f

To a pressure-resistant reaction container, (3-bromo-5-trifluoromethylsulfanylpyridine-2-yl)-methylamine (1.96 g), acetylacetone copper (II) (89 mg), acetylacetone (0.27 g), cesium carbonate (2.34 g), and NMP (7 ml), 28% of aqueous ammonia (5 ml) was added, and stirred at 110° C. for 8.5 hours. After the mixture was cooled to room temperature, into the reaction mixture, water was poured. The insoluble material was filtered through Celite®, and then the filtered material was washed with ethyl acetate, and filtrate was extracted with ethyl acetate. The combined organic layer was dried over sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 1.18 g of N²-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine (Compound (1F)-3).

N²-methyl-5-trifluoromethylsulfanylpyridine-2,3-diamine

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¹H-NMR (CDCl₃) δ: 8.01-7.99 (1H, m), 7.07-7.05 (1H, m), 4.60 (1H, brs), 3.22 (2H, brs), 3.05 (3H, d).

Reference Production Example 21-a

To a mixture of 2-ethylsulfanylbenzoic acid (9.11 g), chloroform (100 ml), and oxalyl chloride (9.72 g), DMF (2 drops) was added, and stirred at room temperature for 6 hours. The reaction mixture was concentrated under reduced pressure to give 10.03 g of 2-ethylsulfanylbenzoic acid chloride (Compound (1H)-241).

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¹H-NMR (CDCl₃) δ: 8.31 (1H, dd), 7.57-7.50 (1H, m), 7.42-7.32 (1H, m), 7.28-7.21 (1H, m), 3.00 (2H, q), 1.41 (3H, t).

Reference Production Example 21-b

To a mixture of N²-methyl-5-trifluoromethylpyridine-2,3-diamine (3.82 g) and THF (40 ml), 2-ethylsulfanylbenzoic acid chloride (4.42 g) was added, stirred at 50° C. for 2 hours, then stirred under reflux for hours. After the mixture was allowed to cool to room temperature, sodium hydrogen carbonate (1.85 g) was added thereto, and stirred at 50° C. for 2 hours. After the mixture was allowed to cool to room temperature, water was poured thereinto, and then the precipitated solid was collected by the filtration. The resulting solid was washed with water and hexane, and dried to give 7.15 g of N-(2-methylamino-5-trifluoromethylpyridine-3-yl)-2-ethylsulfanyl-benzamide (Compound ((1B)-19).

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¹H-NMR (CDCl₃) δ: 8.36 (1H, S), 8.26 (1H, S), 7.85 (1H, d), 7.76 (1H, S), 7.53 (1H, d), 7.47 (1H, t), 7.39 (1H, t), 5.55 (1H, brs), 3.08 (3H, d), 3.01 (2H, q), 1.32 (3H, t).

The above intermediate, Compounds (1B)-(1E) are shown in the following tables.

A compound of the formula (1B):

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wherein, A^2brepresents ═CH—, R^2b, R^4b, R^5b, R^7brepresents a hydrogen atom, and R^1b, R^3b, R^6b, A^1b, A^3b, and n represent a combination of R^1x, R^3x, R^6x, A^1x, A^3x, and n, respectively, shown in Tables 38-58 (Compounds ((1B)-1)-((1B)-504)).

A compound of the formula (1C):

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wherein, X^Crepresents a fluorine atom, A^2Crepresents ═CH—, R^2C, R^4C, R^5C, R^7Crepresents a hydrogen atom, and R^3C, R^6C, A^1C, and A^3Crepresent a combination of R^3x, R^6x, A^1x, and A^3x, respectively, shown in Tables 38-52 (Compound (1C)-F1 to Compound (1C)-F9, Compound (1C)-F37 to Compound (1C)-F45, Compound (1C)-F55 to Compound (1C)-F63, Compound (1C)-F73 to Compound (1C)-F81, Compound (1C)-F109 to Compound (1C)-F117, Compound (1C)-F127 to Compound (1C)-F135, Compound (1C)-F145 to Compound (1C)-F153, Compound (1C)-F181 to Compound (1C)-F189, Compound (1C)-F199 to Compound (1C)-F207, Compound (1C)-F217 to Compound (1C)-F225, Compound (1C)-F253 to Compound (1C)-F261, Compound (1C)-F271 to Compound (1C)-F279, Compound (1C)-F289 to Compound (1C)-F297, Compound (1C)-F325 to Compound (1C)-F333, and Compound (1C)-F343 to Compound (1C)-F351).

A compound of the formula (1C) wherein X^Cis a chlorine atom, A^2Cis ═CH—, R^2C, R^4C, R^5C, R^7Cis a hydrogen atom, R^3C, R^6C, A^1Cand A^3C, represent a combination of R^3x, R^6x, A^1xand A^3x, respectively, shown in Tables 38-52 (Compound (1C)-C1 to Compound (1C)-C9, Compound (1C)-C37 to Compound (1C)-C45, Compound (1C)-C55 to Compound (1C)-C63, Compound (1C)-C73 to Compound (1C)-C81, Compound (1C)-C109 to Compound (1C)-C117, Compound (1C)-C127 to Compound (1C)-C135, Compound (1C)-C145 to Compound (1C)-C153, Compound (1C)-C181 to Compound (1C)-C189, Compound (1C)-C199 to Compound (1C)-C207, Compound (1C)-C217 to Compound (1C)-C225, Compound (1C)-C253 to Compound (1C)-C261, Compound (1C)-C271 to Compound (1C)-C279, Compound (1C)-C289 to Compound (1C)-C297, Compound (1C)-C325 to Compound (1C)-C333, and Compound (1C)-C343 to Compound (1C)-C351).

A compound of the formula (1D):

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wherein, A^2drepresents ═CH—, R^2d, R^4d, R^5d, R^7drepresents a hydrogen atom, and R^3d, R^6d, A^1dand A^3d, represent a combination of R^3x, R^6x, A^1xand A^3x, respectively, shown in Tables 38-58 (Compound (1D)-1 to Compound (1D)-9, Compound (1D)-37 to Compound (1D)-45, Compound (1D)-55 to Compound (1D)-63, Compound (1D)-73 to Compound (1D)-81, Compound (1D)-109 to Compound (1D)-117, Compound (1D)-127 to Compound (1D)-135, Compound (1D)-145 to Compound (1D)-153, Compound (1D)-181 to Compound (1D)-189, Compound (1D)-199 to Compound (1D)-207, Compound (1D)-217 to Compound (1D)-225, Compound (1D)-253 to Compound (1D)-261, Compound (1D)-271 to Compound (1D)-279, Compound (1D)-289 to Compound (1D)-297, Compound (1D)-325 to Compound (1D)-333, Compound (1D)-343 to Compound (1D)-351, Compound (1D)-361 to Compound (1D)-369, Compound (1D)-397 to Compound (1D)-405, Compound (1D)-415 to Compound (1D)-423, Compound (1D)-433 to Compound (1D)-441, Compound (1D)-469 to Compound (1D)-477, and Compound (1D)-487 to Compound (1D)-495).

A compound of the formula (1E):

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wherein, X^erepresents a fluorine atom, A^2erepresents ═CH—, R^2e, R^4e, R^5e, R^7erepresents a hydrogen atom, R^3e, R^6e, A^1e, and A^3erepresent a combination of R^3x, R^6x, and A^3x, respectively, shown in Tables 38-52 (Compound (1E)-F1 to Compound (1E)-F9, Compound (1E)-F37 to Compound (1E)-F45, Compound (1E)-F55 to Compound (1E)-F63, Compound (1E)-F73 to Compound (1E)-F81, Compound (1E)-F109 to Compound (1E)-F117, Compound (1E)-F127 to Compound (1E)-F135, Compound (1E)-F145 to Compound (1E)-F153, Compound (1E)-F181 to Compound (1E)-F189, Compound (1E)-F199 to Compound (1E)-F207, Compound (1E)-F217 to Compound (1E)-F225, Compound (1E)-F253 to Compound (1E)-F261, Compound (1E)-F271 to Compound (1E)-F279, Compound (1E)-F289 to Compound (1E)-F297, Compound (1E)-F325 to Compound (1E)-F333, and Compound (1E)-F343 to Compound (1E)-F351).

A compound of the formula (1E) wherein, X^erepresents a chlorine atom, A^2erepresents ═CH—, R^2e, R^4e, R^5e, R^7erepresents a hydrogen atom, R^3e, R^6e, A^1e, and A^3erepresent a combination of R^3x, R^6x, A^1x, and A^3x, respectively, shown in Tables 38-52 (Compound (1E)-C1 to Compound (1E)-C9, Compound (1E)-C37 to Compound (1E)-C45, Compound (1E)-C55 to Compound (1E)-C63, Compound (1E)-C73 to Compound (1E)-C81, Compound (1E)-C109 to Compound (1E)-C117, Compound (1E)-C127 to Compound (1E)-C135, Compound (1E)-C145 to Compound (1E)-C153, Compound (1E)-C181 to Compound (1E)-C189, Compound (1E)-C199 to Compound (1E)-C207, Compound (1E)-C217 to Compound (1E)-C225, Compound (1E)-C253 to Compound (1E)-C261, Compound (1E)-C271 to Compound (1E)-C279, Compound (1E)-C289 to Compound (1E)-C297, Compound (1E)-C325 to Compound (1E)-C333, and Compound (1E)-C343 to Compound (1E)-C351).

TABLE 38

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

1
Me
H
CF₃
NMe
N
0

2
Me
F
CF₃
NMe
N
0

3
Me
Cl
CF₃
NMe
N
0

4
Me
Br
CF₃
NMe
N
0

5
Me
Me
CF₃
NMe
N
0

6
Me
CF₃
CF₃
NMe
N
0

7
Me
OCF₃
CF₃
NMe
N
0

8
Me
C₂F₅
CF₃
NMe
N
0

9
Me
SF₅
CF₃
NMe
N
0

10
Me
H
CF₃
NMe
N
2

11
Me
F
CF₃
NMe
N
2

12
Me
Cl
CF₃
NMe
N
2

13
Me
Br
CF₃
NMe
N
2

14
Me
Me
CF₃
NMe
N
2

15
Me
CF₃
CF₃
NMe
N
2

16
Me
OCF₃
CF₃
NMe
N
2

17
Me
C₂F₅
CF₃
NMe
N
2

18
Me
SF₅
CF₃
NMe
N
2

19
Et
H
CF₃
NMe
N
0

20
Et
F
CF₃
NMe
N
0

21
Et
Cl
CF₃
NMe
N
0

22
Et
Br
CF₃
NMe
N
0

23
Et
Me
CF₃
NMe
N
0

24
Et
CF₃
CF₃
NMe
N
0

25
Et
OCF₃
CF₃
NMe
N
0

TABLE 39

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

26
Et
C₂F₅
CF₃
NMe
N
0

27
Et
SF₅
CF₃
NMe
N
0

28
Et
H
CF₃
NMe
N
2

29
Et
F
CF₃
NMe
N
2

30
Et
Cl
CF₃
NMe
N
2

31
Et
Br
CF₃
NMe
N
2

32
Et
Me
CF₃
NMe
N
2

33
Et
CF₃
CF₃
NMe
N
2

34
Et
OCF₃
CF₃
NMe
N
2

35
Et
C₂F₅
CF₃
NMe
N
2

36
Et
SF₅
CF₃
NMe
N
2

37
Et
H
CF₃
NMe
CH
0

38
Et
F
CF₃
NMe
CH
0

39
Et
Cl
CF₃
NMe
CH
0

40
Et
Br
CF₃
NMe
CH
0

41
Et
Me
CF₃
NMe
CH
0

42
Et
CF₃
CF₃
NMe
CH
0

43
Et
OCF₃
CF₃
NMe
CH
0

44
Et
C₂F₅
CF₃
NMe
CH
0

45
Et
SF₅
CF₃
NMe
CH
0

46
Et
H
CF₃
NMe
CH
2

47
Et
F
CF₃
NMe
CH
2

48
Et
Cl
CF₃
NMe
CH
2

49
Et
Br
CF₃
NMe
CH
2

50
Et
Me
CF₃
NMe
CH
2

TABLE 40

Intermediate
R^1x
R^3x
R^6x
A^1x
A^1x
n

51
Et
CF₃
CF₃
NMe
CH
2

52
Et
OCF₃
CF₃
NMe
CH
2

53
Et
C₂F₅
CF₃
NMe
CH
2

54
Et
SF₅
CF₃
NMe
CH
2

55
Et
H
CF₃
S
N
0

56
Et
F
CF₃
S
N
0

57
Et
Cl
CF₃
S
N
0

58
Et
Br
CF₃
S
N
0

59
Et
Me
CF₃
S
N
0

60
Et
CF₃
CF₃
S
N
0

61
Et
OCF₃
CF₃
S
N
0

62
Et
C₂F₅
CF₃
S
N
0

63
Et
SF₅
CF₃
S
N
0

64
Et
H
CF₃
S
N
2

65
Et
F
CF₃
S
N
2

66
Et
Cl
CF₃
S
N
2

67
Et
Br
CF₃
S
N
2

68
Et
Me
CF₃
S
N
2

69
Et
CF₃
CF₃
S
N
2

70
Et
OCF₃
CF₃
S
N
2

71
Et
C₂F₅
CF₃
S
N
2

72
Et
SF₅
CF₃
S
N
2

73
Me
H
CF₂CF₃
NMe
N
0

74
Me
F
CF₂CF₃
NMe
N
0

75
Me
Cl
CF₂CF₃
NMe
N
0

TABLE 41

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

76
Me
Br
CF₂CF₃
NMe
N
0

77
Me
Me
CF₂CF₃
NMe
N
0

78
Me
CF₃
CF₂CF₃
NMe
N
0

79
Me
OCF₃
CF₂CF₃
NMe
N
0

80
Me
C₂F₅
CF₂CF₃
NMe
N
0

81
Me
SF₅
CF₂CF₃
NMe
N
0

82
Me
H
CF₂CF₃
NMe
N
2

83
Me
F
CF₂CF₃
NMe
N
2

84
Me
Cl
CF₂CF₃
NMe
N
2

85
Me
Br
CF₂CF₃
NMe
N
2

86
Me
Me
CF₂CF₃
NMe
N
2

87
Me
CF₃
CF₂CF₃
NMe
N
2

88
Me
OCF₃
CF₂CF₃
NMe
N
2

89
Me
C₂F₅
CF₂CF₃
NMe
N
2

90
Me
SF₅
CF₂CF₃
NMe
N
2

91
Et
H
CF₂CF₃
NMe
N
0

92
Et
F
CF₂CF₃
NMe
N
0

93
Et
Cl
CF₂CF₃
NMe
N
0

94
Et
Br
CF₂CF₃
NMe
N
0

95
Et
Me
CF₂CF₃
NMe
N
0

96
Et
CF₃
CF₂CF₃
NMe
N
0

97
Et
OCF₃
CF₂CF₃
NMe
N
0

98
Et
C₂F₅
CF₂CF₃
NMe
N
0

99
Et
SF₅
CF₂CF₃
NMe
N
0

100
Et
H
CF₂CF₃
NMe
N
2

TABLE 42

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

101
Et
F
CF₂CF₃
NMe
N
2

102
Et
Cl
CF₂CF₃
NMe
N
2

103
Et
Br
CF₂CF₃
NMe
N
2

104
Et
Me
CF₂CF₃
NMe
N
2

105
Et
CF₃
CF₂CF₃
NMe
N
2

106
Et
OCF₃
CF₂CF₃
NMe
N
2

107
Et
C₂F₅
CF₂CF₃
NMe
N
2

108
Et
SF₅
CF₂CF₃
NMe
N
2

109
Et
H
CF₂CF₃
NMe
CH
0

110
Et
F
CF₂CF₃
NMe
CH
0

111
Et
Cl
CF₂CF₃
NMe
CH
0

112
Et
Br
CF₂CF₃
NMe
CH
0

113
Et
Me
CF₂CF₃
NMe
CH
0

114
Et
CF₃
CF₂CF₃
NMe
CH
0

115
Et
OCF₃
CF₂CF₃
NMe
CH
0

116
Et
C₂F₅
CF₂CF₃
NMe
CH
0

117
Et
SF₅
CF₂CF₃
NMe
CH
0

118
Et
H
CF₂CF₃
NMe
CH
2

119
Et
F
CF₂CF₃
NMe
CH
2

120
Et
Cl
CF₂CF₃
NMe
CH
2

121
Et
Br
CF₂CF₃
NMe
CH
2

122
Et
Me
CF₂CF₃
NMe
CH
2

123
Et
CF₃
CF₂CF₃
NMe
CH
2

124
Et
OCF₃
CF₂CF₃
NMe
CH
2

125
Et
C₂F₅
CF₂CF₃
NMe
CH
2

TABLE 43

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

126
Et
SF₅
CF₂CF₃
NMe
CH
2

127
Et
H
CF₂CF₃
S
N
0

128
Et
F
CF₂CF₃
S
N
0

129
Et
Cl
CF₂CF₃
S
N
0

130
Et
Br
CF₂CF₃
S
N
0

131
Et
Me
CF₂CF₃
S
N
0

132
Et
CF₃
CF₂CF₃
S
N
0

133
Et
OCF₃
CF₂CF₃
S
N
0

134
Et
C₂F₅
CF₂CF₃
S
N
0

135
Et
SF₅
CF₂CF₃
S
N
0

136
Et
H
CF₂CF₃
S
N
2

137
Et
F
CF₂CF₃
S
N
2

138
Et
Cl
CF₂CF₃
S
N
2

139
Et
Br
CF₂CF₃
S
N
2

140
Et
Me
CF₂CF₃
S
N
2

141
Et
CF₃
CF₂CF₃
S
N
2

142
Et
OCF₃
CF₂CF₃
S
N
2

143
Et
C₂F₅
CF₂CF₃
S
N
2

144
Et
SF₅
CF₂CF₃
S
N
2

145
Me
H
SCF₃
NMe
N
0

146
Me
F
SCF₃
NMe
N
0

147
Me
Cl
SCF₃
NMe
N
0

148
Me
Br
SCF₃
NMe
N
0

149
Me
Me
SCF₃
NMe
N
0

150
Me
CF₃
SCF₃
NMe
N
0

TABLE 44

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

151
Me
OCF₃
SCF₃
NMe
N
0

152
Me
C₂F₅
SCF₃
NMe
N
0

153
Me
SF₅
SCF₃
NMe
N
0

154
Me
H
SCF₃
NMe
N
2

155
Me
F
SCF₃
NMe
N
2

156
Me
Cl
SCF₃
NMe
N
2

157
Me
Br
SCF₃
NMe
N
2

158
Me
Me
SCF₃
NMe
N
2

159
Me
CF₃
SCF₃
NMe
N
2

160
Me
OCF₃
SCF₃
NMe
N
2

161
Me
C₂F₅
SCF₃
NMe
N
2

162
Me
SF₅
SCF₃
NMe
N
2

163
Et
H
SCF₃
NMe
N
0

164
Et
F
SCF₃
NMe
N
0

165
Et
Cl
SCF₃
NMe
N
0

166
Et
Br
SCF₃
NMe
N
0

167
Et
Me
SCF₃
NMe
N
0

168
Et
CF₃
SCF₃
NMe
N
0

169
Et
OCF₃
SCF₃
NMe
N
0

170
Et
C₂F₅
SCF₃
NMe
N
0

171
Et
SF₅
SCF₃
NMe
N
0

172
Et
H
SCF₃
NMe
N
2

173
Et
F
SCF₃
NMe
N
2

174
Et
Cl
SCF₃
NMe
N
2

175
Et
Br
SCF₃
NMe
N
2

TABLE 45

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

176
Et
Me
SCF₃
NMe
N
2

177
Et
CF₃
SCF₃
NMe
N
2

178
Et
OCF₃
SCF₃
NMe
N
2

179
Et
C₂F₅
SCF₃
NMe
N
2

180
Et
SF₅
SCF₃
NMe
N
2

181
Et
H
SCF₃
NMe
CH
0

182
Et
F
SCF₃
NMe
CH
0

183
Et
Cl
SCF₃
NMe
CH
0

184
Et
Br
SCF₃
NMe
CH
0

185
Et
Me
SCF₃
NMe
CH
0

186
Et
CF₃
SCF₃
NMe
CH
0

187
Et
OCF₃
SCF₃
NMe
CH
0

188
Et
C₂F₅
SCF₃
NMe
CH
0

189
Et
SF₅
SCF₃
NMe
CH
0

190
Et
H
SCF₃
NMe
CH
2

191
Et
F
SCF₃
NMe
CH
2

192
Et
Cl
SCF₃
NMe
CH
2

193
Et
Br
SCF₃
NMe
CH
2

194
Et
Me
SCF₃
NMe
CH
2

195
Et
CF₃
SCF₃
NMe
CH
2

196
Et
OCF₃
SCF₃
NMe
CH
2

197
Et
C₂F₅
SCF₃
NMe
CH
2

198
Et
SF₅
SCF₃
NMe
CH
2

199
Et
H
SCF₃
S
N
0

200
Et
F
SCF₃
S
N
0

TABLE 46

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

201
Et
Cl
SCF₃
S
N
0

202
Et
Br
SCF₃
S
N
0

203
Et
Me
SCF₃
S
N
0

204
Et
CF₃
SCF₃
S
N
0

205
Et
OCF₃
SCF₃
S
N
0

206
Et
C₂F₅
SCF₃
S
N
0

207
Et
SF₅
SCF₃
S
N
0

208
Et
H
SCF₃
S
N
2

209
Et
F
SCF₃
S
N
2

210
Et
Cl
SCF₃
S
N
2

211
Et
Br
SCF₃
S
N
2

212
Et
Me
SCF₃
S
N
2

213
Et
CF₃
SCF₃
S
N
2

214
Et
OCF₃
SCF₃
S
N
2

215
Et
C₂F₅
SCF₃
S
N
2

216
Et
SF₅
SCF₃
S
N
2

217
Me
H
SOCF₃
NMe
N
0

218
Me
F
SOCF₃
NMe
N
0

219
Me
Cl
SOCF₃
NMe
N
0

220
Me
Br
SOCF₃
NMe
N
0

221
Me
Me
SOCF₃
NMe
N
0

222
Me
CF₃
SOCF₃
NMe
N
0

223
Me
OCF₃
SOCF₃
NMe
N
0

224
Me
C₂F₅
SOCF₃
NMe
N
0

225
Me
SF₅
SOCF₃
NMe
N
0

TABLE 47

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

226
Me
H
SOCF₃
NMe
N
2

227
Me
F
SOCF₃
NMe
N
2

228
Me
Cl
SOCF₃
NMe
N
2

229
Me
Br
SOCF₃
NMe
N
2

230
Me
Me
SOCF₃
NMe
N
2

231
Me
CF₃
SOCF₃
NMe
N
2

232
Me
OCF₃
SOCF₃
NMe
N
2

233
Me
C₂F₅
SOCF₃
NMe
N
2

234
Me
SF₅
SOCF₃
NMe
N
2

235
Et
H
SOCF₃
NMe
N
0

236
Et
F
SOCF₃
NMe
N
0

237
Et
Cl
SOCF₃
NMe
N
0

238
Et
Br
SOCF₃
NMe
N
0

239
Et
Me
SOCF₃
NMe
N
0

240
Et
CF₃
SOCF₃
NMe
N
0

241
Et
OCF₃
SOCF₃
NMe
N
0

242
Et
C₂F₅
SOCF₃
NMe
N
0

243
Et
SF₅
SOCF₃
NMe
N
0

244
Et
H
SOCF₃
NMe
N
2

245
Et
F
SOCF₃
NMe
N
2

246
Et
Cl
SOCF₃
NMe
N
2

247
Et
Br
SOCF₃
NMe
N
2

248
Et
Me
SOCF₃
NMe
N
2

249
Et
CF₃
SOCF₃
NMe
N
2

250
Et
OCF₃
SOCF₃
NMe
N
2

TABLE 48

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

251
Et
C₂F₅
SOCF₃
NMe
N
2

252
Et
SF₅
SOCF₃
NMe
N
2

253
Et
H
SOCF₃
NMe
CH
0

254
Et
F
SOCF₃
NMe
CH
0

255
Et
Cl
SOCF₃
NMe
CH
0

256
Et
Br
SOCF₃
NMe
CH
0

257
Et
Me
SOCF₃
NMe
CH
0

258
Et
CF₃
SOCF₃
NMe
CH
0

259
Et
OCF₃
SOCF₃
NMe
CH
0

260
Et
C₂F₅
SOCF₃
NMe
CH
0

261
Et
SF₅
SOCF₃
NMe
CH
0

262
Et
H
SOCF₃
NMe
CH
2

263
Et
F
SOCF₃
NMe
CH
2

264
Et
Cl
SOCF₃
NMe
CH
2

265
Et
Br
SOCF₃
NMe
CH
2

266
Et
Me
SOCF₃
NMe
CH
2

267
Et
CF₃
SOCF₃
NMe
CH
2

268
Et
OCF₃
SOCF₃
NMe
CH
2

269
Et
C₂F₅
SOCF₃
NMe
CH
2

270
Et
SF₅
SOCF₃
NMe
CH
2

271
Et
H
SOCF₃
S
N
0

272
Et
F
SOCF₃
S
N
0

273
Et
Cl
SOCF₃
S
N
0

274
Et
Br
SOCF₃
S
N
0

275
Et
Me
SOCF₃
S
N
0

TABLE 49

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

276
Et
CF₃
SOCF₃
S
N
0

277
Et
OCF₃
SOCF₃
S
N
0

278
Et
C₂F₅
SOCF₃
S
N
0

279
Et
SF₅
SOCF₃
S
N
0

280
Et
H
SOCF₃
S
N
2

281
Et
F
SOCF₃
S
N
2

282
Et
Cl
SOCF₃
S
N
2

283
Et
Br
SOCF₃
S
N
2

284
Et
Me
SOCF₃
S
N
2

285
Et
CF₃
SOCF₃
S
N
2

286
Et
OCF₃
SOCF₃
S
N
2

287
Et
C₂F₅
SOCF₃
S
N
2

288
Et
SF₅
SOCF₃
S
N
2

289
Me
H
SO₂CF₃
NMe
N
0

290
Me
F
SO₂CF₃
NMe
N
0

291
Me
Cl
SO₂CF₃
NMe
N
0

292
Me
Br
SO₂CF₃
NMe
N
0

293
Me
Me
SO₂CF₃
NMe
N
0

294
Me
CF₃
SO₂CF₃
NMe
N
0

295
Me
OCF₃
SO₂CF₃
NMe
N
0

296
Me
C₂F₅
SO₂CF₃
NMe
N
0

297
Me
SF₅
SO₂CF₃
NMe
N
0

298
Me
H
SO₂CF₃
NMe
N
2

299
Me
F
SO₂CF₃
NMe
N
2

300
Me
Cl
SO₂CF₃
NMe
N
2

TABLE 50

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

301
Me
Br
SO₂CF₃
NMe
N
2

302
Me
Me
SO₂CF₃
NMe
N
2

303
Me
CF₃
SO₂CF₃
NMe
N
2

304
Me
OCF₃
SO₂CF₃
NMe
N
2

305
Me
C₂F₅
SO₂CF₃
NMe
N
2

306
Me
SF₅
SO₂CF₃
NMe
N
2

307
Et
H
SO₂CF₃
3NMe
N
0

308
Et
F
SO₂CF₃
NMe
N
0

309
Et
Cl
SO₂CF₃
NMe
N
0

310
Et
Br
SO₂CF₃
NMe
N
0

311
Et
Me
SO₂CF₃
NMe
N
0

312
Et
CF₃
SO₂CF₃
NMe
N
0

313
Et
OCF₃
SO₂CF₃
NMe
N
0

314
Et
C₂F₅
SO₂CF₃
NMe
N
0

315
Et
SF₅
SO₂CF₃
NMe
N
0

316
Et
H
SO₂CF₃
NMe
N
2

317
Et
F
SO₂CF₃
NMe
N
2

318
Et
Cl
SO₂CF₃
NMe
N
2

319
Et
Br
SO₂CF₃
NMe
N
2

320
Et
Me
SO₂CF₃
NMe
N
2

321
Et
CF₃
SO₂CF₃
NMe
N
2

322
Et
OCF₃
SO₂CF₃
NMe
N
2

323
Et
C₂F₅
SO₂CF₃
NMe
N
2

324
Et
SF₅
SO₂CF₃
NMe
N
2

325
Et
H
SO₂CF₃
NMe
CH
0

TABLE 51

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

326
Et
F
SO₂CF₃
NMe
CH
0

327
Et
Cl
SO₂CF₃
NMe
CH
0

328
Et
Br
SO₂CF₃
NMe
CH
0

329
Et
Me
SO₂CF₃
NMe
CH
0

330
Et
CF₃
SO₂CF₃
NMe
CH
0

331
Et
OCF₃
SO₂CF₃
NMe
CH
0

332
Et
C₂F₅
SO₂CF₃
NMe
CH
0

333
Et
SF₅
SO₂CF₃
NMe
CH
0

334
Et
H
SO₂CF₃
NMe
CH
2

335
Et
F
SO₂CF₃
NMe
CH
2

336
Et
Cl
SO₂CF₃
NMe
CH
2

337
Et
Br
SO₂CF₃
NMe
CH
2

338
Et
Me
SO₂CF₃
NMe
CH
2

339
Et
CF₃
SO₂CF₃
NMe
CH
2

340
Et
OCF₃
SO₂CF₃
NMe
CH
2

341
Et
C₂F₅
SO₂CF₃
NMe
CH
2

342
Et
SF₅
SO₂CF₃
NMe
CH
2

343
Et
H
SO₂CF₃
S
N
0

344
Et
F
SO₂CF₃
S
N
0

345
Et
Cl
SO₂CF₃
S
N
0

346
Et
Br
SO₂CF₃
S
N
0

347
Et
Me
SO₂CF₃
S
N
0

348
Et
CF₃
SO₂CF₃
S
N
0

349
Et
OCF₃
SO₂CF₃
S
N
0

350
Et
C₂F₅
SO₂CF₃
S
N
0

TABLE 52

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

351
Et
SF₅
SO₂CF₃
S
N
0

352
Et
H
SO₂CF₃
S
N
2

353
Et
F
SO₂CF₃
S
N
2

354
Et
Cl
SO₂CF₃
S
N
2

355
Et
Br
SO₂CF₃
S
N
2

356
Et
Me
SO₂CF₃
S
N
2

357
Et
CF₃
SO₂CF₃
S
N
2

358
Et
OCF₃
SO₂CF₃
S
N
2

359
Et
C₂F₅
SO₂CF₃
S
N
2

360
Et
SF₅
SO₂CF₃
S
N
2

TABLE 53

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

361
Me
H
Br
NMe
N
0

362
Me
F
Br
NMe
N
0

363
Me
Cl
Br
NMe
N
0

364
Me
Br
Br
NMe
N
0

365
Me
Me
Br
NMe
N
0

366
Me
CF₃
Br
NMe
N
0

367
Me
OCF₃
Br
NMe
N
0

368
Me
C₂F₅
Br
NMe
N
0

369
Me
SF₅
Br
NMe
N
0

370
Me
H
Br
NMe
N
2

371
Me
F
Br
NMe
N
2

372
Me
Cl
Br
NMe
N
2

373
Me
Br
Br
NMe
N
2

374
Me
Me
Br
NMe
N
2

375
Me
CF₃
Br
NMe
N
2

376
Me
OCF₃
Br
NMe
N
2

377
Me
C₂F₅
Br
NMe
N
2

378
Me
SF₅
Br
NMe
N
2

379
Et
H
Br
NMe
N
0

380
Et
F
Br
NMe
N
0

381
Et
Cl
Br
NMe
N
0

382
Et
Br
Br
NMe
N
0

383
Et
Me
Br
NMe
N
0

384
Et
CF₃
Br
NMe
N
0

385
Et
OCF₃
Br
NMe
N
0

TABLE 54

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

386
Et
C₂F₅
Br
NMe
N
0

387
Et
SF₅
Br
NMe
N
0

388
Et
H
Br
NMe
N
2

389
Et
F
Br
NMe
N
2

390
Et
Cl
Br
NMe
N
2

391
Et
Br
Br
NMe
N
2

392
Et
Me
Br
NMe
N
2

393
Et
CF₃
Br
NMe
N
2

394
Et
OCF₃
Br
NMe
N
2

395
Et
C₂F₅
Br
NMe
N
2

396
Et
SF₅
Br
NMe
N
2

397
Et
H
Br
NMe
CH
0

398
Et
F
Br
NMe
CH
0

399
Et
Cl
Br
NMe
CH
0

400
Et
Br
Br
NMe
CH
0

401
Et
Me
Br
NMe
CH
0

402
Et
CF₃
Br
NMe
CH
0

403
Et
OCF₃
Br
NMe
CH
0

404
Et
C₂F₅
Br
NMe
CH
0

405
Et
SF₅
Br
NMe
CH
0

406
Et
H
Br
NMe
CH
2

407
Et
F
Br
NMe
CH
2

408
Et
Cl
Br
NMe
CH
2

409
Et
Br
Br
NMe
CH
2

410
Et
Me
Br
NMe
CH
2

TABLE 55

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

411
Et
CF₃
Br
NMe
CH
2

412
Et
OCF₃
Br
NMe
CH
2

413
Et
C₂F₅
Br
NMe
CH
2

414
Et
SF₅
Br
NMe
CH
2

415
Et
H
Br
S
N
0

416
Et
F
Br
S
N
0

417
Et
Cl
Br
S
N
0

418
Et
Br
Br
S
N
0

419
Et
Me
Br
S
N
0

420
Et
CF₃
Br
S
N
0

421
Et
OCF₃
Br
S
N
0

422
Et
C₂F₅
Br
S
N
0

423
Et
SF₅
Br
S
N
0

424
Et
H
Br
S
N
2

425
Et
F
Br
S
N
2

426
Et
Cl
Br
S
N
2

427
Et
Br
Br
S
N
2

428
Et
Me
Br
S
N
2

429
Et
CF₃
Br
S
N
2

430
Et
OCF₃
Br
S
N
2

431
Et
C₂F₅
Br
S
N
2

432
Et
SF₅
Br
S
N
2

433
Me
H
I
NMe
N
0

434
Me
F
I
NMe
N
0

435
Me
Cl
I
NMe
N
0

TABLE 56

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

436
Me
Br
I
NMe
N
0

437
Me
Me
I
NMe
N
0

438
Me
CF₃
I
NMe
N
0

439
Me
OCF₃
I
NMe
N
0

440
Me
C₂F₅
I
NMe
N
0

441
Me
SF₅
I
NMe
N
0

442
Me
H
I
NMe
N
2

443
Me
F
I
NMe
N
2

444
Me
Cl
I
NMe
N
2

445
Me
Br
I
NMe
N
2

446
Me
Me
I
NMe
N
2

447
Me
CF₃
I
NMe
N
2

448
Me
OCF₃
I
NMe
N
2

449
Me
C₂F₅
I
NMe
N
2

450
Me
SF₅
I
NMe
N
2

451
Et
H
I
NMe
N
0

452
Et
F
I
NMe
N
0

453
Et
Cl
I
NMe
N
0

454
Et
Br
I
NMe
N
0

455
Et
Me
I
NMe
N
0

456
Et
CF₃
I
NMe
N
0

457
Et
OCF₃
I
NMe
N
0

458
Et
C₂F₅
I
NMe
N
0

459
Et
SF₅
I
NMe
N
0

460
Et
H
I
NMe
N
2

TABLE 57

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

461
Et
F
I
NMe
N
2

462
Et
Cl
I
NMe
N
2

463
Et
Br
I
NMe
N
2

464
Et
Me
I
NMe
N
2

465
Et
CF₃
I
NMe
N
2

466
Et
OCF₃
I
NMe
N
2

467
Et
C₂F₅
I
NMe
N
2

468
Et
SF₅
I
NMe
N
2

469
Et
H
I
NMe
CH
0

470
Et
F
I
NMe
CH
0

471
Et
Cl
I
NMe
CH
0

472
Et
Br
I
NMe
CH
0

473
Et
Me
I
NMe
CH
0

474
Et
CF₃
I
NMe
CH
0

475
Et
OCF₃
I
NMe
CH
0

476
Et
C₂F₅
I
NMe
CH
0

477
Et
SF₅
I
NMe
CH
0

478
Et
H
I
NMe
CH
2

479
Et
F
I
NMe
CH
2

480
Et
Cl
I
NMe
CH
2

481
Et
Br
I
NMe
CH
2

482
Et
Me
I
NMe
CH
2

483
Et
CF₃
I
NMe
CH
2

484
Et
OCF₃
I
NMe
CH
2

485
Et
C₂F₅
I
NMe
CH
2

TABLE 58

Intermediate
R^1x
R^3x
R^6x
A^1x
A^3x
n

486
Et
SF₅
I
NMe
CH
2

487
Et
H
I
S
N
0

488
Et
F
I
S
N
0

489
Et
Cl
I
S
N
0

490
Et
Br
I
S
N
0

491
Et
Me
I
S
N
0

492
Et
CF₃
I
S
N
0

493
Et
OCF₃
I
S
N
0

494
Et
C₂F₅
I
S
N
0

495
Et
SF₅
I
S
N
0

496
Et
H
I
S
N
2

497
Et
F
I
S
N
2

498
Et
Cl
I
S
N
2

499
Et
Br
I
S
N
2

500
Et
Me
I
S
N
2

501
Et
CF₃
I
S
N
2

502
Et
OCF₃
I
S
N
2

503
Et
C₂F₅
I
S
N
2

504
Et
SF₅
I
S
N
2

In the above Tables 38-58, Me represents a methyl group, and Et represents an ethyl group.

The ¹H-NMR data of Compound (1B) are shown below. Compound (1B)-505

embedded image

¹H-NMR (CDCl₃) δ: 8.76 (1H, S), 8.33 (1H, s), 8.04 (1H, S), 7.88-7.76 (2H, m), 7.78-7.60 (2H, m), 6.30 (1H, brs), 3.30-3.20 (1H, m), 3.10 (3H, d), 3.10-2.98 (1H, m), 1.26 (3H, t).

Compound (1B)-28

¹H-NMR (CDCl₃) δ: 8.39 (1H, S), 8.08 (1H, d), 7.85-7.55 (4H, m), 7.26-7.20 (1H, m), 6.29 (1H, brs), 3.51 (2H, q), 3.05 (3H, d), 1.33 (3H, t).

Compound (1B)-379

embedded image

¹H-NMR (CDCl₃) δ: 8.28 (1H, brs), 8.14 (1H, d), 7.90-7.75 (2H, m), 7.58-7.35 (3H, m), 5.06 (1H, brs), 3.20-2.96 (5H, m), 1.32 (3H, q).

Compound (1B)-507

embedded image

¹H-NMR (CDCl₃) δ: 8.39-8.38 (1H, m), 7.80 (1H, brs), 7.70-7.68 (1H, m), 7.67-7.61 (2H, m), 7.44-7.39 (1H, m), 5.80 (1H, brs), 3.10-3.07 (3H, m), 3.00 (2H, q), 1.26 (3H, t).

Compound (1B)-508

embedded image

¹H-NMR (CDCl₃) δ: 8.41-8.38 (1H, m), 8.29-8.26 (1H, m), 8.16-8.12 (1H, m), 7.93-7.89 (1H, m), 7.86 (1H, brs), 7.76-7.73 (1H, m), 5.39-5.33 (1H, brm), 3.14 (2H, q), 3.08 (3H, d), 1.42 (3H, t).

Compound (1B)-24

¹H-NMR (CDCl₃) δ: 8.39 (1H, brs), 7.96 (1H, brs), 7.92 (1H, d), 7.77-7.71 (2H, m), 7.62 (1H, d), 5.42 (1H, brs), 3.12-3.03 (5H, m), 1.37 (3H, t).

Compound (1B)-509

embedded image

¹H-NMR (CDCl₃) δ: 8.38 (1H, brs), 7.89 (1H, d), 7.80 (1H, d), 7.57-7.51 (1H, m), 7.50-7.44 (1H, m), 7.43-7.36 (1H, m), 7.05-6.99 (1H, m), 5.22 (1H, brs), 3.06 (3H, s), 3.00 (2H, q), 1.32 (3H, t).

Compound (1B)-451

¹H-NMR (CDCl₃) δ: 8.26 (1H, brs), 7.87 (1H, s), 7.84 (1H, d), 7.52 (1H, d), 7.49-7.42 (1H, m), 7.41-7.35 (1H, m), 7.20-7.15 (1H, m), 5.12 (1H, brs), 3.02-2.97 (5H, m), 1.32 (3H, t).

Compound (1B)-511

embedded image

¹H-NMR (CDCl₃) δ: 8.30 (1H, s), 8.10 (1H, brs), 7.76-7.76 (2H, m), 7.50 (1H, d), 7.45 (1H, t), 7.36 (1H, t), 5.41 (1H, d), 4.37-4.27 (1H, m), 2.99 (2H, q), 1.30-1.28 (9H, m).

Compound (1B)-37

¹H-NMR (CDCl₃) δ: 8.18 (1H, brs), 7.84 (1H, d), 7.60-7.30 (5H, m), 6.77 (1H, d), 4.85 (1H, brs), 3.01 (2H, q), 2.93 (3H, d), 1.32 (3H, t).

Compound (1B)-33

¹H-NMR (Acetone-d₆) δ: 9.56 (1H, brs), 8.36-8.35 (1H, m), 8.30-8.23 (3H, m), 7.87-7.85 (1H, m), 6.44 (1H, brs), 3.65 (2H, q), 3.03 (3H, d), 1.31 (3H, t).

Compound (1B)-516

embedded image

¹H-NMR (CDCl₃) δ: 9.35 (1H, s), 8.92 (1H, s), 8.03 (1H, d), 7.74 (1H, s), 7.62 (1H, d), 7.57 (1H, s), 7.44 (1H, d), 7.14 (1H, d), 3.05 (2H, q), 1.36 (3H, t).

The ¹H-NMR data of Compound (1C) are shown below.

Compound (1C)-F505

embedded image

¹H-NMR (CDCl₃) δ: 8.40 (1H, s), 7.73-7.71 (1H, m), 7.29-7.24 (3H, m), 4.99 (1H, brs), 3.08 (3H, d).

Compound (1C)-F3

¹H-NMR (CDCl₃) δ: 8.40 (1H, s), 8.14 (1H, dd), 7.93 (1H, d), 7.72 (1H, s), 7.36 (1H, d), 7.32-7.27 (1H, m), 4.99 (1H, brs), 3.08 (3H, d).

Compound (1C)-F4

¹H-NMR (CDCl₃) δ: 8.39 (1H, s), 8.06 (1H, dd), 7.93 (1H, d), 7.72 (1H, s), 7.51 (1H, d), 7.44 (1H, d), 4.99 (1H, brs), 3.07 (3H, d).

Compound (1C)-F5

¹H-NMR (CDCl₃) δ: 8.38 (1H, s), 8.15-7.94 (2H, m), 7.73 (1H, s), 7.15 (1H, d), 7.03 (1H, d), 5.06 (1H, brs), 3.07 (3H, d), 2.45 (3H, s).

Compound (1C)-F6

¹H-NMR (CDCl₃) δ: 8.41 (1H, brs), 8.33 (1H, t), 7.99 (1H, d), 7.75 (1H, d), 7.64 (1H, d), 7.53 (1H, d), 4.97 (1H, brs), 3.08 (3H, d).

Compound (1C)-F37

¹H-NMR (CDCl₃) δ: 8.25-8.06 (2H, m), 7.64-7.53 (2H, m), 7.47 (1H, d), 7.34 (1H, t), 7.24-7.15 (1H, m), 6.80 (1H, d), 4.38 (1H, brs), 2.93 (3H, d).

Compound (1C)-C37

¹H-NMR (CDCl₃) δ: 7.85 (1H, d), 7.64 (1H, brs), 7.56 (1H, s), 7.52-7.38 (4H, m), 6.80 (1H, d), 4.49 (1H, brs), 2.93 (3H, s).

Compound (1C)-F42

¹H-NMR (CDCl₃) δ: 8.33 (1H, t), 8.10 (1H, d), 7.66-7.57 (2H, m), 7.55-7.45 (2H, m), 6.82 (1H, d), 4.29 (1H, brs), 2.93 (3H, d).

Compound (1C)-F145

¹H-NMR (CDCl₃) δ: 8.35 (1H, s), 8.19 (1H, t), 8.02 (1H, d), 7.76 (1H, s), 7.64-7.54 (1H, m), 7.36 (1H, t), 7.25-7.20 (1H, m), 5.06 (1H, brs), 3.07 (3H, d).

Compound (1C)-C145

¹H-NMR (CDCl₃) δ: 8.35 (1H, brs), 7.86 (1H, d), 7.77-7.71 (1H, m), 7.63-7.39 (4H, m), 5.19 (1H, brs), 3.08 (3H, d).

Compound (1C)-F150

¹H-NMR (CDCl₃) δ: 8.40-8.28 (2H, m), 7.98 (1H, d), 7.77 (1H, s), 7.64 (1H, d), 7.53 (1H, d), 4.98 (1H, brs), 3.08 (3H, d).

Compound (1C)-F73

¹H-NMR (CDCl₃) δ: 8.34 (1H, brs), 8.24-8.15 (1H, m), 8.05 (1H, d), 7.68 (1H, s), 7.65-7.54 (1H, m), 7.40-7.32 (1H, m), 7.25-7.18 (1H, m), 5.09 (1H, brs), 3.09 (3H, d).

Compound (1C)-C73

¹H-NMR (CDCl₃) δ: 8.35 (1H, s), 7.87 (1H, d), 7.65 (1H, s), 7.62 (1H, brs), 7.54-7.40 (3H, m), 5.21 (1H, brs), 3.09 (3H, d).

Compound (1C)-F78

¹H-NMR (CDCl₃) δ: 8.40-8.29 (2H, m), 8.01 (1H, d), 7.69 (1H, s), 7.64 (1H, d), 7.53 (1H, d), 5.00 (1H, brs), 3.09 (3H, d).

Compound (1C)-F1

¹H-NMR (CDCl₃) δ: 8.39 (1H, s), 8.19 (1H, t), 8.03 (1H, d), 7.74 (1H, s), 7.66-7.55 (1H, m), 7.36 (1H, t), 7.25-7.19 (1H, m), 5.05 (1H, brs), 3.08 (3H, d).

Compound (1C)-C1

¹H-NMR (CDCl₃) δ: 8.40 (1H, s), 7.86 (1H, d), 7.72 (1H, s), 7.59 (1H, brs), 7.54-7.40 (3H, m), 5.15 (1H, brs), 3.08 (3H, d).

Compound (1C)-F506

embedded image

¹H-NMR (DMSO-D₆) δ: 9.59 (1H, d), 8.50 (1H, s), 7.91 (1H, t), 7.70-7.60 (1H, m), 7.45-7.33 (4H, m), 7.07 (1H, d).

The ¹H-NMR data of Compound (1D) are shown below.

Compound (1D)-1

¹H-NMR (CDCl₃) δ: 8.75-8.72 (1H, m), 8.35-8.33 (1H, m), 7.55-7.51 (1H, m), 7.47-7.41 (2H, m), 7.37-7.32 (1H, m), 4.12 (1H, brs), 3.84 (3H, s).

The ¹H-NMR data of Compound (1E) are shown below.

Compound (1E)-F505

embedded image

¹H-NMR (CDCl₃) δ: 8.29 (1H, d), 7.90 (1H, t), 7.81 (1H, dd), 7.66 (1H, d), 7.57 (1H, d), 7.48 (1H, d), 3.82 (3H, d).

Compound (1E)-F9

¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.37-8.35 (1H, m), 7.93-7.87 (1H, m), 7.80 (1H, dd), 7.74 (1H, dd), 3.92 (3H, d).

Compound (1E)-F7

¹H-NMR (CDCl₃) δ: 8.75-8.73 (1H, m), 8.34-8.32 (1H, m), 7.81 (1H, t), 7.29-7.25 (1H, m), 7.22-7.18 (1H, m), 3.91 (3H, d).

Compound (1E)-F42

¹H-NMR (CDCl₃) δ: 8.13 (1H, s), 7.91 (1H, t), 7.67-7.61 (2H, m), 7.58-7.51 (2H, m), 3.82 (3H, d).

Compound (1E)-C1

¹H-NMR (CDCl₃) δ: 8.73 (1H, dd), 8.33 (1H, dd), 7.61-7.51 (3H, m), 7.51-7.45 (1H, m), 3.81 (3H, s)

Compound (1E)-F1

¹H-NMR (CDCl₃) δ: 8.72 (1H, d), 8.32 (1H, d), 7.79-7.65 (1H, m), 7.63-7.58 (1H, m), 7.42-7.36 (1H, m), 7.33-7.25 (1H, m), 3.89 (3H, d)

Compound (1E)-F506

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.37-8.35 (1H, m), 7.63-7.55 (1H, m), 7.15 (2H, t), 3.86 (3H, s).

Compound (1E)-F507

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¹H-NMR (CDCl₃) δ: 8.76-8.73 (1H, m), 8.35-8.33 (1H, m), 7.53-7.40 (2H, m), 7.37-7.30 (1H, m), 3.92 (3H, d).

Compound (1E)-F508

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.33-8.31 (1H, m), 7.33-7.18 (3H, m), 3.99 (3H, s), 3.89 (3H, d).

Compound (1E)-F509

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¹H-NMR (CDCl₃) δ: 8.70-8.69 (1H, m), 8.30-8.28 (1H, m), 7.66 (1H, t), 6.91 (1H, dd), 6.81 (1H, dd), 3.91 (3H, s), 3.88 (3H, d).

Compound (1E)-F3

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.33-8.31 (1H, m), 7.70 (1H, t), 7.39 (1H, dd), 7.34 (1H, dd), 3.89 (3H, d).

Compound (1E)-C505

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.38-8.36 (1H, m), 7.58-7.51 (1H, m), 7.43 (1H, d), 7.23 (1H, t), 3.80 (3H, s).

Compound (1E)-F510

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¹H-NMR (CDCl₃) δ: 8.72-8.70 (1H, m), 8.33-8.31 (1H, m), 7.56-7.49 (1H, m), 6.93-6.86 (2H, m), 3.84 (3H, s), 3.77 (3H, s).

Compound (1E)-F511

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¹H-NMR (CDCl₃) δ: 10.78 (1H, brs), 8.76-8.74 (1H, m), 8.33-8.31 (1H, m), 7.46-7.39 (1H, m), 6.98 (1H, d), 6.84-6.78 (1H, m), 3.96 (3H, d).

Compound (1E)-C506

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¹H-NMR (CDCl₃) δ: 8.79-8.77 (1H, m), 8.48 (1H, d), 8.38-8.36 (1H, m), 8.34 (1H, dd), 7.82 (1H, d), 3.84 (3H, s).

Compound (1E)-C507

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¹H-NMR (CDCl₃) δ: 8.73-8.71 (1H, m), 8.33-8.31 (1H, m), 7.48-7.43 (2H, m), 7.32 (1H, dd), 3.81 (3H, s), 3.06 (2H, q), 1.41 (3H, t).

Compound (1E)-F512

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¹H-NMR (CDCl₃) δ: 8.73-8.70 (1H, m), 8.32-8.30 (1H, m), 7.55-7.49 (1H, m), 7.47-7.41 (1H, m), 7.31-7.22 (1H, m), 3.88 (3H, d), 2.40 (3H, d).

Compound (1E)-F5

¹H-NMR (CDCl₃) δ: 8.71-8.69 (1H, m), 8.31-8.30 (1H, m), 7.61 (1H, t), 7.18 (1H, d), 7.10 (1H, d), 3.88 (3H, d), 2.48 (3H, s).

Compound (1E)-F4

¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.33-8.32 (1H, m), 7.63 (1H, t), 7.56-7.48 (2H, m), 3.88 (3H, d).

Compound (1E)-F513

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¹H-NMR (CDCl₃) δ: 8.70-8.68 (1H, m), 8.35-8.33 (1H, m), 7.64-7.55 (1H, m), 7.18-7.12 (2H, m), 3.86 (3H, s).

Compound (1E)-F514

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¹H-NMR (CDCl₃) δ: 8.77-8.75 (1H, m), 8.40-8.38 (1H, m), 6.96-6.90 (2H, m), 6.75 (1H, t), 3.86-3.85 (3H, m).

Compound (1E)-F515

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¹H-NMR (CDCl₃) δ: 8.76-8.74 (1H, m), 8.37-8.35 (1H, m), 7.38-7.33 (2H, m), 3.85 (3H, s).

Compound (1E)-F516

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¹H-NMR (CDCl₃) δ: 8.74-8.73 (1H, m), 8.35-8.33 (1H, m), 7.81 (1H, t), 7.69-7.65 (2H, m), 7.63-7.60 (1H, m), 7.55-7.49 (3H, m), 7.48-7.43 (1H, m), 3.94 (3H, d).

Compound (1E)-F517

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¹H-NMR (CDCl₃) δ: 8.79-8.77 (1H, m), 8.40-8.38 (1H, m), 7.47-7.42 (2H, m), 3.87 (3H, s).

Compound (1E)-F518

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¹H-NMR (CDCl₃) δ: 7.90 (1H, t), 7.63 (1H, dd), 7.59 (1H, d), 7.54 (1H, d), 6.84 (1H, d), 4.05 (3H, d), 4.02 (2H, brs).

Compound (1E)-C508

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¹H-NMR (CDCl₃) δ: 8.74-8.72 (1H, m), 8.35-8.33 (1H, m), 7.50-7.47 (1H, m), 7.41-7.34 (2H, m), 3.79 (3H, s), 2.50 (3H, s).

Compound (1E)-F519

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¹H-NMR (CDCl₃) δ: 8.76-8.75 (1H, m), 8.36-8.34 (1H, m), 7.99-7.94 (1H, m), 7.91-7.86 (1H, m), 7.54-7.49 (1H, m), 3.92 (3H, d).

Compound (1E)-F78

¹H-NMR (CDCl₃) δ: 8.71-8.69 (1H, m), 8.34-8.33 (1H, m), 7.93-7.88 (1H, m), 7.69-7.66 (1H, m), 7.61-7.57 (1H, m), 3.92 (3H, d).

Compound (1E)-F77

¹H-NMR (CDCl₃) δ: 8.65 (1H, s), 8.29 (1H, s), 7.64-7.58 (1H, m), 7.20-7.17 (1H, m), 7.13-7.08 (1H, m), 3.90-3.87 (3H, m), 2.49 (3H, s).

Compound (1E)-F149

¹H-NMR (CDCl₃) δ: 8.66-8.64 (1H, m), 8.39-8.37 (1H, m), 7.60 (1H, t), 7.20-7.16 (1H, m), 7.12-7.08 (1H, m), 3.86 (3H, d), 2.48 (3H, s).

Compound (1E)-F73

¹H-NMR (CDCl₃) δ: 8.67 (1H, d), 8.30 (1H, d), 7.74 (1H, td), 7.66-7.57 (1H, m), 7.39 (1H, td), 7.34-7.27 (1H, m), 3.90 (3H, d).

Compound (1E)-C73

¹H-NMR (CDCl₃) δ: 8.68 (1H, d), 8.31 (1H, d), 7.62-7.53 (3H, m), 7.48 (1H, td), 3.81 (3H, s).

Compound (1E)-F79

¹H-NMR (CDCl₃) δ: 8.70-8.68 (1H, m), 8.33-8.30 (1H, m), 7.81 (1H, t), 7.30-7.25 (1H, m), 7.22-7.18 (1H, m), 3.91 (3H, d).

The above intermediate, Compounds (1F)-(1G) are shown in the following tables.

A compound of the formula (1F):

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wherein A^2frepresents ═CH—, R^7frepresents a hydrogen atom, and R^6f, R^8f, and A^3frepresent a combination of R^6x, R^8x, and A^3x, respectively, shown in Tables 59-61 (Compounds ((1F)-1)-((1F)-56)).

A compound of the formula (1G):

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wherein X^grepresents a chlorine atom, A^2grepresents ═CH—, R^7grepresents a hydrogen atom, and R^6g, R^8g, and A^3grepresent a combination of R^6x, R^8x, and A^3x, respectively, shown in Tables 59-61 (Compounds ((1G)-C1)-((1G)-C56)).

A compound of the formula (1G) wherein X^grepresents a bromine atom, A^2grepresents ═CH—, R^7grepresents a hydrogen atom, and R^6g, R^8g, and A^3grepresent a combination of R^6x, R^8x, and A^3x, respectively, shown in Tables 59-61 (Compounds ((1G)-B1)-((1G)-B56)).

TABLE 59

Intermediate
R^6x
R^8x
A^3x

1
CF₃
CH₃
N

2
CF₂CF₃
CH₃
N

3
SCF₃
CH₃
N

4
SOCF₃
CH₃
N

5
SO₂CF₃
CH₃
N

6
I
CH₃
N

7
SF₅
CH₃
N

8
CF₃
CH₂CH₃
N

9
CF₂CF₃
CH₂CH₃
N

10
SCF₃
CH₂CH₃
N

11
SOCF₃
CH₂CH₃
N

12
SO₂CF₃
CH₂CH₃
N

13
I
CH₂CH₃
N

14
SF₅
CH₂CH₃
N

15
CF₃
CH(CH₃)₂
N

16
CF₂CF₃
CH(CH₃)₂
N

17
SCF₃
CH(CH₃)₂
N

18
SOCF₃
CH(CH₃)₂
N

19
SO₂CF₃
CH(CH₃)₂
N

20
I
CH(CH₃)₂
N

21
SF₅
CH(CH₃)₂
N

22
CF₃
H
N

23
CF₂CF₃
H
N

24
SCF₃
H
N

25
SOCF₃
H
N

TABLE 60

Intermediate
R^6x
R^8x
A^3x

26
SO₂CF₃
H
N

27
I
H
N

28
SF₅
H
N

29
CF₃
CH₃
CH

30
CF₂CF₃
CH₃
CH

31
SCF₃
CH₃
CH

32
SOCF₃
CH₃
CH

33
SO₂CF₃
CH₃
CH

34
I
CH₃
CH

35
SF₅
CH₃
CH

36
CF₃
CH₂CH₃
CH

37
CF₂CF₃
CH₂CH₃
CH

38
SCF₃
CH₂CH₃
CH

39
SOCF₃
CH₂CH₃
CH

40
SO₂CF₃
CH₂CH₃
CH

41
I
CH₂CH₃
CH

42
SF₅
CH₂CH₃
CH

43
CF₃
CH(CH₃)₂
CH

44
CF₂CF₃
CH(CH₃)₂
CH

45
SCF₃
CH(CH₃)₂
CH

46
SOCF₃
CH(CH₃)₂
CH

47
SO₂CF₃
CH(CH₃)₂
CH

48
I
CH(CH₃)₂
CH

49
SF₅
CH(CH₃)₂
CH

50
CF₃
H
CH

TABLE 61

Intermediate
R^6x
R^8x
A^3x

51
CF₂CF₃
H
CH

52
SCF₃
H
CH

53
SOCF₃
H
CH

54
SO₂CF₃
H
CH

55
I
H
CH

56
SF₅
H
CH

The above intermediate, Compounds (1H)-(1I) are shown in the following tables.

A compound of the formula (1H):

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wherein, R^1h, R^2h, R^3h, R^4h, R^5h, R^13h, and n represent a combination of R^1x, R^2x, R^3x, R^4x, R^5x, R^13x, and n, respectively, shown in Tables 62-75 (Compounds ((1H)-1)-((1H)-288).

A compound of the formula (1I):

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wherein, R¹ⁱ, R²ⁱ, R³ⁱ, R⁴ⁱ, R⁵ⁱ, and r represent a combination of R^1x, R^2x, R^3x, R^4x, R^5x, and n, respectively, shown in Tables 63, 64, 66, and 67 (Compounds ((1I)-17)-((1I)-48) and Compounds ((1I)-65)-((1I)-96).

TABLE 62

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

1
Me
H
H
H
H
H
0

2
Me
H
F
H
H
H
0

3
Me
H
Cl
H
H
H
0

4
Me
H
Br
H
H
H
0

5
Me
H
Me
H
H
H
0

6
Me
H
Et
H
H
H
0

7
Me
H
Pr
H
H
H
0

8
Me
H
CF₃
H
H
H
0

9
Me
H
C₂F₅
H
H
H
0

10
Me
H
SF₅
H
H
H
0

11
Me
H
OCH₃
H
H
H
0

12
Me
H
OC₂H₅
H
H
H
0

13
Me
H
OCF₃
H
H
H
0

14
Me
H
SCF₃
H
H
H
0

15
Me
H
SOCF₃
H
H
H
0

16
Me
H
SO₂CF₃
H
H
H
0

TABLE 63

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

17
Me
H
H
H
H
H
1

18
Me
H
F
H
H
H
1

19
Me
H
Cl
H
H
H
1

20
Me
H
Br
H
H
H
1

21
Me
H
Me
H
H
H
1

22
Me
H
Et
H
H
H
1

23
Me
H
Pr
H
H
H
1

24
Me
H
CF₃
H
H
H
1

25
Me
H
C₂F₅
H
H
H
1

TABLE 64

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

26
Me
H
SF₅
H
H
H
1

27
Me
H
OCH₃
H
H
H
1

28
Me
H
OC₂H₅
H
H
H
1

29
Me
H
OCF₃
H
H
H
1

30
Me
H
SCF₃
H
H
H
1

31
Me
H
SOCF₃
H
H
H
1

32
Me
H
SO₂CF₃
H
H
H
1

33
Me
H
H
H
H
H
2

34
Me
H
F
H
H
H
2

35
Me
H
Cl
H
H
H
2

36
Me
H
Br
H
H
H
2

37
Me
H
Me
H
H
H
2

38
Me
H
Et
H
H
H
2

39
Me
H
Pr
H
H
H
2

40
Me
H
CF₃
H
H
H
2

41
Me
H
C₂F₅
H
H
H
2

42
Me
H
SF₅
H
H
H
2

43
Me
H
OCH₃
H
H
H
2

44
Me
H
OC₂H₅
H
H
H
2

45
Me
H
OCF₃
H
H
H
2

46
Me
H
SCF₃
H
H
H
2

47
Me
H
SOCF₃
H
H
H
2

48
Me
H
SO₂CF₃
H
H
H
2

TABLE 65

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

49
Et
H
H
H
H
H
0

50
Et
H
F
H
H
H
0

51
Et
H
Cl
H
H
H
0

52
Et
H
Br
H
H
H
0

53
Et
H
Me
H
H
H
0

54
Et
H
Et
H
H
H
0

55
Et
H
Pr
H
H
H
0

56
Et
H
CF₃
H
H
H
0

57
Et
H
C₂F₅
H
H
H
0

58
Et
H
SF₅
H
H
H
0

59
Et
H
OCH₃
H
H
H
0

60
Et
H
OC₂H₅
H
H
H
0

61
Et
H
OCF₃
H
H
H
0

62
Et
H
SCF₃
H
H
H
0

63
Et
H
SOCF₃
H
H
H
0

64
Et
H
SO₂CF₃
H
H
H
0

TABLE 66

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

65
Et
H
H
H
H
H
1

66
Et
H
F
H
H
H
1

67
Et
H
Cl
H
H
H
1

68
Et
H
Br
H
H
H
1

69
Et
H
Me
H
H
H
1

70
Et
H
Et
H
H
H
1

71
Et
H
Pr
H
H
H
1

72
Et
H
CF₃
H
H
H
1

73
Et
H
C₂F₅
H
H
H
1

74
Et
H
SF₅
H
H
H
1

75
Et
H
OCH₃
H
H
H
1

76
Et
H
OC₂H₅
H
H
H
1

77
Et
H
OCF₃
H
H
H
1

78
Et
H
SCF₃
H
H
H
1

79
Et
H
SOCF₃
H
H
H
1

80
Et
H
SO₂CF₃
H
H
H
1

81
Et
H
H
H
H
H
2

82
Et
H
F
H
H
H
2

83
Et
H
Cl
H
H
H
2

84
Et
H
Br
H
H
H
2

85
Et
H
Me
H
H
H
2

86
Et
H
Et
H
H
H
2

87
Et
H
Pr
H
H
H
2

88
Et
H
CF₃
H
H
H
2

89
Et
H
C₂F₅
H
H
H
2

TABLE 67

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

90
Et
H
SF₅
H
H
H
2

91
Et
H
OCH₃
H
H
H
2

92
Et
H
OC₂H₅
H
H
H
2

93
Et
H
OCF₃
H
H
H
2

94
Et
H
SCF₃
H
H
H
2

95
Et
H
SOCF₃
H
H
H
2

96
Et
H
SO₂CF₃
H
H
H
2

TABLE 68

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

97
Me
H
H
H
H
OH
0

98
Me
H
F
H
H
OH
0

99
Me
H
Cl
H
H
OH
0

100
Me
H
Br
H
H
OH
0

101
Me
H
Me
H
H
OH
0

102
Me
H
Et
H
H
OH
0

103
Me
H
Pr
H
H
OH
0

104
Me
H
CF₃
H
H
OH
0

105
Me
H
C₂F₅
H
H
OH
0

106
Me
H
SF₅
H
H
OH
0

107
Me
H
OCH₃
H
H
OH
0

108
Me
H
OC₂H₅
H
H
OH
0

109
Me
H
OCF₃
H
H
OH
0

110
Me
H
SCF₃
H
H
OH
0

111
Me
H
SOCF₃
H
H
OH
0

112
Me
H
SO₂CF₃
H
H
OH
0

113
Me
H
H
H
H
OH
1

114
Me
H
F
H
H
OH
1

115
Me
H
Cl
H
H
OH
1

116
Me
H
Br
H
H
OH
1

117
Me
H
Me
H
H
OH
1

118
Me
H
Et
H
H
OH
1

119
Me
H
Pr
H
H
OH
1

120
Me
H
CF₃
H
H
OH
1

TABLE 69

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

121
Me
H
C₂F₅
H
H
OH
1

122
Me
H
SF₅
H
H
OH
1

123
Me
H
OCH₃
H
H
OH
1

124
Me
H
OC₂H₅
H
H
OH
1

125
Me
H
OCF₃
H
H
OH
1

126
Me
H
SCF₃
H
H
OH
1

127
Me
H
SOCF₃
H
H
OH
1

128
Me
H
SO₂CF₃
H
H
OH
1

129
Me
H
H
H
H
OH
2

130
Me
H
F
H
H
OH
2

131
Me
H
Cl
H
H
OH
2

132
Me
H
Br
H
H
OH
2

133
Me
H
Me
H
H
OH
2

134
Me
H
Et
H
H
OH
2

135
Me
H
Pr
H
H
OH
2

136
Me
H
CF₃
H
H
OH
2

137
Me
H
C₂F₅
H
H
OH
2

138
Me
H
SF₅
H
H
OH
2

139
Me
H
OCH₃
H
H
OH
2

140
Me
H
OC₂H₅
H
H
OH
2

141
Me
H
OCF₃
H
H
OH
2

142
Me
H
SCF₃
H
H
OH
2

143
Me
H
SOCF₃
H
H
OH
2

144
Me
H
SO₂CF₃
H
H
OH
2

145
Et
H
H
H
H
OH
0

TABLE 70

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

146
Et
H
F
H
H
OH
0

147
Et
H
Cl
H
H
OH
0

148
Et
H
Br
H
H
OH
0

149
Et
H
Me
H
H
OH
0

150
Et
H
Et
H
H
OH
0

151
Et
H
Pr
H
H
OH
0

152
Et
H
CF₃
H
H
OH
0

153
Et
H
C₂F₅
H
H
OH
0

154
Et
H
SF₅
H
H
OH
0

155
Et
H
OCH₃
H
H
OH
0

156
Et
H
OC₂H₅
H
H
OH
0

157
Et
H
OCF₃
H
H
OH
0

158
Et
H
SCF₃
H
H
OH
0

159
Et
H
SOCF₃
H
H
OH
0

160
Et
H
SO₂CF₃
H
H
OH
0

161
Et
H
H
H
H
OH
1

162
Et
H
F
H
H
OH
1

163
Et
H
Cl
H
H
OH
1

164
Et
H
Br
H
H
OH
1

165
Et
H
Me
H
H
OH
1

166
Et
H
Et
H
H
OH
1

167
Et
H
Pr
H
H
OH
1

168
Et
H
CF₃
H
H
OH
1

169
Et
H
C₂F₅
H
H
OH
1

170
Et
H
SF₅
H
H
OH
1

TABLE 71

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

171
Et
H
OCH₃
H
H
OH
1

172
Et
H
OC₂H₅
H
H
OH
1

173
Et
H
OCF₃
H
H
OH
1

174
Et
H
SCF₃
H
H
OH
1

175
Et
H
SOCF₃
H
H
OH
1

176
Et
H
SO₂CF₃
H
H
OH
1

177
Et
H
H
H
H
OH
2

178
Et
H
F
H
H
OH
2

179
Et
H
Cl
H
H
OH
2

180
Et
H
Br
H
H
OH
2

181
Et
H
Me
H
H
OH
2

182
Et
H
Et
H
H
OH
2

183
Et
H
Pr
H
H
OH
2

184
Et
H
CF₃
H
H
OH
2

185
Et
H
C₂F₅
H
H
OH
2

186
Et
H
SF₅
H
H
OH
2

187
Et
H
OCH₃
H
H
OH
2

188
Et
H
OC₂H₅
H
H
OH
2

189
Et
H
OCF₃
H
H
OH
2

190
Et
H
SCF₃
H
H
OH
2

191
Et
H
SOCF₃
H
H
OH
2

192
Et
H
SO₂CF₃
H
H
OH
2

193
Me
H
H
H
H
Cl
0

194
Me
H
F
H
H
Cl
0

195
Me
H
Cl
H
H
Cl
0

TABLE 72

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

196
Me
H
Br
H
H
Cl
0

197
Me
H
Me
H
H
Cl
0

198
Me
H
Et
H
H
Cl
0

199
Me
H
Pr
H
H
Cl
0

200
Me
H
CF₃
H
H
Cl
0

201
Me
H
C₂F₅
H
H
Cl
0

202
Me
H
SF₅
H
H
C1
0

203
Me
H
OCH₃
H
H
Cl
0

204
Me
H
OC₂H₅
H
H
Cl
0

205
Me
H
OCF₃
H
H
Cl
0

206
Me
H
SCF₃
H
H
Cl
0

207
Me
H
SOCF₃
H
H
Cl
0

208
Me
H
SO₂CF₃
H
H
Cl
0

209
Me
H
H
H
H
Cl
1

210
Me
H
F
H
H
Cl
1

211
Me
H
Cl
H
H
Cl
1

212
Me
H
Br
H
H
Cl
1

213
Me
H
Me
H
H
Cl
1

214
Me
H
Et
H
H
Cl
1

215
Me
H
Pr
H
H
Cl
1

216
Me
H
CF₃
H
H
Cl
1

217
Me
H
C₂F₅
H
H
Cl
1

218
Me
H
SF₅
H
H
Cl
1

219
Me
H
OCH₃
H
H
Cl
1

220
Me
H
OC₂H₅
H
H
Cl
1

TABLE 73

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

221
Me
H
OCF₃
H
H
Cl
1

222
Me
H
SCF₃
H
H
Cl
1

223
Me
H
SOCF₃
H
H
Cl
1

224
Me
H
SO₂CF₃
H
H
Cl
1

225
Me
H
H
H
H
Cl
2

226
Me
H
F
H
H
Cl
2

227
Me
H
Cl
H
H
Cl
2

228
Me
H
Br
H
H
Cl
2

229
Me
H
Me
H
H
Cl
2

230
Me
H
Et
H
H
Cl
2

231
Me
H
Pr
H
H
Cl
2

232
Me
H
CF₃
H
H
Cl
2

233
Me
H
C₂F₅
H
H
Cl
2

234
Me
H
SF₅
H
H
Cl
2

235
Me
H
OCH₃
H
H
Cl
2

236
Me
H
OC₂H₅
H
H
Cl
2

237
Me
H
OCF₃
H
H
Cl
2

238
Me
H
SCF₃
H
H
Cl
2

239
Me
H
SOCF₃
H
H
C1
2

240
Me
H
SO₂CF₃
H
H
Cl
2

241
Et
H
H
H
H
Cl
0

242
Et
H
F
H
H
Cl
0

243
Et
H
Cl
H
H
Cl
0

244
Et
H
Br
H
H
Cl
0

245
Et
H
Me
H
H
Cl
0

TABLE 74

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

246
Et
H
Et
H
H
Cl
0

247
Et
H
Pr
H
H
Cl
0

248
Et
H
CF₃
H
H
Cl
0

249
Et
H
C₂F₅
H
H
Cl
0

250
Et
H
SF₅
H
H
Cl
0

251
Et
H
OCH₃
H
H
Cl
0

252
Et
H
OC₂H₅
H
H
Cl
0

253
Et
H
OCF₃
H
H
Cl
0

254
Et
H
SCF₃
H
H
Cl
0

255
Et
H
SOCF₃
H
H
Cl
0

256
Et
H
SO₂CF₃
H
H
Cl
0

257
Et
H
H
H
H
Cl
1

258
Et
H
F
H
H
Cl
1

259
Et
H
Cl
H
H
Cl
1

260
Et
H
Br
H
H
Cl
1

261
Et
H
Me
H
H
Cl
1

262
Et
H
Et
H
H
Cl
1

263
Et
H
Pr
H
H
Cl
1

264
Et
H
CF₃
H
H
Cl
1

265
Et
H
C₂F₅
H
H
Cl
1

266
Et
H
SF₅
H
H
Cl
1

267
Et
H
OCH₃
H
H
Cl
1

268
Et
H
OC₂H₅
H
H
Cl
1

269
Et
H
OCF₃
H
H
Cl
1

270
Et
H
SCF₃
H
H
Cl
1

TABLE 75

Intermediate
R^1x
R^2x
R^3x
R^4x
R^5x
R^13x
n

271
Et
H
SOCF₃
H
H
C1
1

272
Et
H
SO₂CF₃
H
H
C1
1

273
Et
H
H
H
H
Cl
2

274
Et
H
F
H
H
Cl
2

275
Et
H
Cl
H
H
Cl
2

276
Et
H
Br
H
H
Cl
2

277
Et
H
Me
H
H
Cl
2

278
Et
H
Et
H
H
C1
2

279
Et
H
Pr
H
H
Cl
2

280
Et
H
CF₃
H
H
C1
2

281
Et
H
C₂F₅
H
H
Cl
2

282
Et
H
SF₅
H
H
Cl
2

283
Et
H
OCH₃
H
H
Cl
2

284
Et
H
OC₂H₅
H
H
Cl
2

285
Et
H
OCF₃
H
H
Cl
2

286
Et
H
SCF₃
H
H
Cl
2

287
Et
H
SOCF₃
H
H
C1
2

288
Et
H
SO₂CF₃
H
H
Cl
2

In the above Tables 62-75, Me represents a methyl group, and Et represents an ethyl group.

The ¹H-NMR data of Compound (1H) are shown below.

Compound (1H)-184

¹H-NMR (CDCl₃) δ: 9.23 (1H, brs), 8.37 (1H, brs), 8.03-7.98 (2H, m), 3.63 (2H, q), 1.39 (3H, t)

Compound (1H)-280

¹H-NMR (CDCl₃) δ: 8.33 (1H, brs), 8.09-7.98 (2H, m), 3.43 (2H, q), 1.38 (3H, t)

Compound (1H)-177

¹H-NMR (CDCl₃) δ: 8.12 (1H, dd), 7.87 (1H, dd), 7.77-7.68 (2H, m), 3.59 (2H, q), 1.35 (3H, t).

Compound (1H)-248

¹H-NMR (CDCl₃) δ: 8.22 (1H, d), 7.55 (1H, s), 7.43 (1H, d), 3.02 (2H, q), 1.43 (3H, t).

The ¹H-NMR data of Compound (1I) are shown below.

Compound (1I)-88

¹H-NMR (CDCl₃) δ: 8.43-8.42 (1H, m), 8.10-8.03 (2H, m), 3.45 (2H, q), 1.38 (3H, t)

Formulation Example 1

Any one of Present Compounds 1-427 (10 parts) is dissolved in a mixture of xylene (35 parts) and N,N-dimethylformamide (35 parts), and to the mixture is added polyoxyethylene styryl phenyl ether (14 parts) and calcium dodecylbenzenesulfonate (6 parts), and stirred to give emulsions of each compound.

Formulation Example 2

Sodium lauryl sulfate (4 parts), calcium lignin sulfonate (2 parts), synthetic hydrated silicone oxide powder (20 parts) and diatomite (54 parts) are mixed, then to the mixture is added any one of Present Compounds 1-427 (20 parts), and mixed to give wettable powders of each compound.

Formulation Example 3

To any one of Present Compounds 1-427 (2 parts) is added synthetic hydrated silicone oxide powder (1 part), calcium lignin sulfonate (2 parts), bentonite (30 parts), and kaolin clay (65 parts), and mixed. Then, to the mixture is added an appropriate amount of water, further stirred, granulated with a granulator, and draft-dried to give granules of each compound.

Formulation Example 4

Any one of Present Compounds 1-427 (1 part) is dissolved in an appropriate amount of acetone. To the mixture is added synthetic hydrated silicone oxide powder (5 parts), PAP (0.3 parts), and Fubasami clay (93.7 parts), and well stirred. Then, acetone is removed by evaporation to give powders of each compound.

Formulation Example 5

A mixture (ratio by weight=1:1) of polyoxyethylene alkyl ether sulfate ammonium salt and white carbon (35 parts), any one of Present Compounds 1-427 (10 parts), and water (55 parts) are mixed, pulverized by a wet grinding method to give formulations of each compounds.

Formulation Example 6

Any one of Present Compounds 1-427 (0.1 parts) is dissolved in xylene (5 parts) and trichloroethane (5 parts), and mixed with deodorized kerosine (89.9 parts) to give oil solutions of each compounds.

Formulation Example 7

Any one of Present Compounds 1-427 (10 mg) is dissolved in acetone (0.5 ml). The mixture is added to animal powdered solid feed (powdered solid feed for breeding, CE-2, from CLEA Japan, Inc.), (5 g) and mixed uniformly. Then, acetone is removed by evaporation to give poison baits of each compound.

Formulation Example 8

Any one of Present Compounds 1-427 (0.1 parts) and Neothiosol (Chuo Kasei Co. Ltd.) (49.9 parts) are charged into an aerosol container. After an aerosol valve is attached to the container, dimethyl ether (25 parts) and LPG (25 parts) are charged into the container. The container is vibrated, and attaching an actuator to give oily aerosols of each compound.

Formulation Example 9

Any one of Present Compounds 1-427 (0.6 parts), BHT (2,6-di-tert-butyl-4-methylphenol) (0.01 parts), xylene (5 parts), deodorized kerosine (3.39 parts), and an emulsifier (Atmos 300 (a registered trade name for Atmos Chemical Ltd.)) (1 part) are mixed and dissolved. The mixture and distilled water (50 parts) are charged into an aerosol container, and attaching a valve. Then, propellant (LPG) (40 parts) is pressure-charged into the container through the valve to give aqueous aerosols of each compound.

The effects of the present compounds to control pests are shown in Test Examples.

Test Example 1

The test spray solutions were prepared by diluting the formulations of each of Present Compounds 1-7, 10-14, 18-23, 33-38, 46, 53, 55, 66, 68-70, 72, 75, 81-83, 88-90, 98-99, 102-104, 112-113, 115-118, 121-123, 126-142, 144, 151, 156-159, 161, 167-171, 174-176, 183, 185-186, 188, 192-194, 209-210, 214-215, 235, 238-243, 246-256, 259, 262, 264, 270-273, 279-280, 285, 291-292, 294, 297-299, 301-302, 306-313, 316-319, 324-325, 327, 330-331, 333, 343, 345, 353, 357-361, 371 and 374-379 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, on a cucumber seedling (the first true leaf stage) planted in a plastic cup was inoculated with about 30 Aphis gossypii, and leaving it for a day. Twenty ml of each of the above test spray solutions was sprayed on this seedling.

Six days after spraying, the number of the surviving Aphis gossypii parasitized on the leaves of the cucumber was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

wherein the non-treated section represents a section where the test spray solution prepared by diluting the formulation without the present compound in Formulation Example 5 with the same amount of water as in the treated-section was sprayed.

As a result, in the treated-section of the test spray solution of each of Present Compounds 1-7, 10-14, 18-23, 33-38, 46, 53, 55, 66, 68-70, 72, 75, 81-83, 88-90, 98-99, 102-104, 112-113, 115-118, 121-123, 126-142, 144, 151, 156-159, 161, 167-171, 174-176, 183, 185-186, 188, 192-194, 209-210, 214-215, 235, 238-243, 246-256, 259, 262, 264, 270-273, 279-280, 285, 291-292, 294, 297-299, 301-302, 306-313, 316-319, 324-325, 327, 330-331, 333, 343, 345, 353, 357-361, 371 and 374-379, the control value of 90% or more was shown.

Test Example 2

The test diluted solutions were prepared by diluting the formulations of each of Present Compounds 1-6, 13, 14, 16, 21-23, 33, 34, 36, 43, 46, 48-50, 53, 55, 66, 69, 70, 82, 83, 88, 89, 98-100, 116-118, 122-123, 133-135, 137, 139-140, 142-143, 156-159, 167, 169, 171, 175-176, 192-194, 224, 237-239, 241-243, 247, 254, 256, 280, 299, 306, 317-319, 330-331, 333, 353, 376 and 379 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

A root part of a cucumber seedling (the first true leaf stage) from which soil had been washed off was immersed in 5 ml of each of the diluted solutions, and one day after treatment, on the cucumber leaf surface was inoculated with 30 Aphis gossypii (whole stage). After further seven days, the number of insect of living Aphis gossypii parasitized on the leaves of the cucumber was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

wherein the non-treated section represents a section where the test diluted solution prepared by diluting the formulation without the present compound in Formulation Example 5 with the same amount of water as in the treated-section was used.

As a result, in the treated-section of the test diluted solution of each of Present Compounds 1-6, 13, 14, 16, 21-23, 33, 34, 36, 43, 46, 48-50, 53, 55, 66, 69, 70, 82, 83, 88, 89, 98-100, 116-118, 122-123, 133-135, 137, 139-140, 142-143, 156-159, 167, 169, 171, 175-176, 192-194, 224, 237-239, 241-243, 247, 247, 254, 256, 280, 299, 306, 317-319, 330-331, 333, 353, 376 and 379, the control value of 90% or more was shown.

Test Example 3

The test diluted solutions were prepared by diluting the formulations of each of Present Compounds 2-6, 35-38, 50, 55, 89, 90, 112-113, 116-118, 123, 130, 132, 134-135, 157-158, 169-171, 175-176, 194, 209-210, 214-215, 239-240, 242-243, 248, 254, 270-273, 280, 299, 302, 306, 309, 318-319, 330-331, 333, 345, 359, 361 and 375-376 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, a cucumber seedling (the second true leaf stage) planted in a plastic cup was drenched at its foot with 5 ml of each of the diluted solutions, and kept in a greenhouse of 25° C. for 7 days. On the cucumber leaf surface was inoculated with 30 Aphis gossypii (whole stage), and further kept in the greenhouse for 6 days, then the number of insect of living Aphis gossypii parasitized on the leaves of this cucumber was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

As a result, in the treated-section of the test diluted solution of each of Present Compounds 2-6, 35-38, 50, 55, 89, 90, 112-113, 116-118, 123, 130, 132, 134-135, 157-158, 169-171, 175-176, 194, 209-210, 214-215, 239-240, 242-243, 248, 254, 270-273, 280, 299, 302, 306, 309, 318-319, 330-331, 333, 345, 359, 361 and 375-376, the control value of 90% or more was shown.

Test Example 4

The test spray solutions were prepared by diluting the formulations of each of Present Compounds 1, 3-7, 12, 14, 21, 33-38, 46, 55, 68, 69, 83, 84, 88-90, 102, 112-113, 116-118, 128, 130-133, 136-139, 142-143, 152, 156-158, 161, 169-171, 174-176, 183-186, 188, 201, 209-210, 214-215, 238, 246, 248, 251, 262, 292, 298-299, 301-302, 306, 308-309, 314, 324-325, 327, 343, 353, 360, 374 and 376 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, a rice seedling (the second leaf stage) planted in a polyethylene cup was sprayed with 10 ml of each of the above test spray solutions. After air-drying, third-fourth instar larvae of Nilaparvata lugens were released, and kept in the greenhouse of 25° C. After 6 days, the number of insect of living Nilaparvata lugens parasitized on the rice was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

As a result, in the treated-section of the test spray solution of each of Present Compounds 1, 3-7, 12, 14, 21, 33-38, 46, 55, 68, 69, 83, 84, 88-90, 102, 112-113, 116-118, 128, 130-133, 136-139, 142-143, 152, 156-158, 161, 169-171, 174-176, 183-186, 188, 201, 209-210, 214-215, 238, 246, 248, 251, 262, 292, 298-299, 301-302, 306, 308-309, 314, 324-325, 327, 343, 353, 360, 374 and 376, the control value of 90% or more was shown.

Test Example 5

The test diluted solutions were prepared by diluting the formulations of each of Present Compounds 4-6, 33-36, 38, 55, 89, 90, 112-113, 117-118, 123, 130, 132, 137-138, 143, 156-158, 169-171, 174-176, 185, 214, 248, 251, 272, 292, 294, 297-299, 301-302, 306, 324, 327, 343, 345, 353, 357, 359-361 and 374-376 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, a rice seedling (2 weeks after sowing, the second leaf stage) planted in a plastic cup was drenched at its foot with 5 ml of each of the diluted solutions, and kept in a greenhouse of 25° C. for 7 days. Twenty third-fourth instar larvae of Nilaparvata lugens were released, and further kept in the greenhouse for 6 days, then the number of insect of living Nilaparvata lugens parasitized on the rice was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

As a result, in the treated-section of the test diluted solution of each of Present Compounds 4-6, 33-36, 38, 55, 89, 90, 112-113, 117-118, 123, 130, 132, 137-138, 143, 156-158, 169-171, 174-176, 185, 214, 248, 251, 272, 292, 294, 297-299, 301-302, 306, 324, 327, 343, 345, 353, 357, 359-361 and 374-376, the control value of 90% or more was shown.

Test Example 6

The test spray solutions were prepared by diluting the formulations of each of Present Compounds 4-6, 21, 22, 49, 50, 55, 75, 88, 112-113, 116-118, 128-132, 161, 169-171, 174-176, 188, 209-210, 214-215, 238-240, 247-248, 255, 259, 262, 270-273, 280, 291-292, 296-299, 301-302, 306-311, 317, 319, 331, 333, 343, 345, 357, 360, 374 and 376 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, Bemisia tabaci adult was released on a tomato seedling (the third true leaf stage) planted in a polyethylene cup, and made to lay eggs for about 72 hours. The tomato seedling was kept in a greenhouse for 8 days. When instar larvae hatched from the eggs, the above test spray solution was sprayed in the amount of 20 ml/cup. The cup was kept in a greenhouse at 25° C. After the keeping for 7 days, the number of surviving instar larvae on the tomato leaves was examined, and a control value was calculated according to the following equation:

Control value (%)={1−(Cb×Tai)/(Cai×Tb))×100

wherein symbols represent as follows:

Cb: the number of insects in a non-treated section before treatment,

Cai: the number of insects in a non-treated section in observation,

Tb: the number of insects in a treated-section before treatment,

Tai: the number of insects in a treated-section in observation;

As a result, in the treated-section of the test spray solution of each of Present Compounds 4-6, 21, 22, 49, 50, 55, 75, 88, 112-113, 116-118, 128-132, 161, 169-171, 174-176, 188, 209-210, 214-215, 238-240, 247-248, 255, 259, 262, 270-273, 280, 291-292, 296-299, 301-302, 306-311, 317, 319, 331, 333, 343, 345, 357, 360, 374 and 376, the control value of 90% or more was shown.

Test Example 7

The test spray solutions were prepared by diluting the formulations of each of Present Compounds 1-14, 16-23, 25, 28-36, 42-47, 49, 50, 53-55, 59, 64, 66, 68-76, 80, 81-83, 85-90, 97-98, 100, 116-118, 123, 133-142, 144, 151-154, 156-160, 169-171, 174-176, 181, 183-188, 190-191, 193-194, 197-198, 201-203, 209-210, 214-215, 230, 238-243, 246-248, 262-264, 278-281, 285-287, 292, 294, 299-303, 306-307, 311, 313-316, 318-319, 327, 330-333, 335, 341-343, 345, 348-349, 353, 358, 360, 365, 369-371 and 374-378 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, Cabbage (the third leaf stage) planted in a polyethylene cup was sprayed with 20 mL/cup of each of the test spray solution. After the test solution was dried, the aerial part was cut off, and then placed in a 50 mL volume cup. Five second instar larvae of Plutella xylostella were released into the cup, and the cup was sealed with a lid. After the cup was kept at 25° C. for 5 days, the number of living insects was counted. A death rate was calculated according to the following equation:

Death rate (%)=(Number of dead insects/Number of tested insects)×100

As a result, in the treated-section of the test spray solution of each of Present Compounds 1-14, 16-23, 25, 28-36, 42-47, 49, 50, 53-55, 59, 64, 66, 68-76, 80-83, 85-90, 97-98, 100, 116-118, 123, 133-142, 144, 151-154, 156-160, 169-171, 174-176, 181, 183-188, 190-191, 193-194, 197-198, 201-203, 209-210, 214-215, 230, 238-243, 246-248, 262-264, 278-281, 285-287, 292, 294, 299-303, 306-307, 311, 313-316, 318-319, 327, 330-333, 335, 341-343, 345, 348-349, 353, 358, 360, 365, 369-371 and 374-378, the death rate of 80% or more was shown.

Test Example 8

The test spray solutions were prepared by diluting the formulations of each of Present Compounds 2-9, 11, 13, 14, 17-20, 22, 23, 28, 29, 31, 35-37, 43-47, 54-55, 68-83, 86-90, 106, 112-113, 117-118, 128-129, 131-138, 140-142, 157-158, 161, 164, 169-171, 174-176, 183-185, 187-188, 191, 194, 201-203, 209-210, 214-215, 230, 238-240, 242-243, 246-248, 251, 262-263, 270-275, 278-281, 285-287, 290, 292, 294, 296-302, 305-316, 318-319, 324-325, 327, 329-333, 335, 341-343, 345, 349, 355-357, 360, 369-371 and 374-378 obtained in Formulation Example 5 with water so as to give 500 ppm of an active ingredient concentration.

On the other hand, an apple tree was planted in a plastic cup, and grown until the seventh-eighth leaf was spread. The apple tree was sprayed with 20 mL/cup of each of the test spray solution. After the test solution was dried, 60 first-instar Adoxophyes orana fasciata were released, and the cup was covered with a plastic cup upside-down which the bottom was cut off and a filter paper was put thereon. After 7 days, the number of living insects was counted, and a death rate was calculated according to the following equation:

Death rate (%)=(Number of dead insects/Number of tested insects)×100

As a result, in the treated-section of the test spray solution of each of Present Compounds 2-9, 11, 13, 14, 17-20, 22, 23, 28, 29, 31, 35-37, 43-47, 54-55, 68-83, 86-90, 106, 112-113, 117-118, 128-129, 131-138, 140-142, 157-158, 161, 164, 169-171, 174-176, 183-185, 187-188, 191, 194, 201-203, 209-210, 214-215, 230, 238-240, 242-243, 246-248, 251, 262-263, 270-275, 278-281, 285-287, 290, 292, 294, 296-302, 305-316, 318-319, 324-325, 327, 329-333, 335, 341-343, 345, 349, 355-357, 360, 369-371 and 374-378, the death rate of 90% or more was shown.

INDUSTRIAL APPLICABILITY

The present compound has an activity of controlling pests and is useful as an active ingredient of a pest controlling agent.

Number	Date	Country	Kind
2010-287412	Dec 2010	JP	national
2011-166768	Jul 2011	JP	national
2011-263374	Dec 2011	JP	national

FUSED HETEROCYCLIC COMPOUND AND USE FOR PEST CONTROL THEREOF

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