Patent Application
20240190805
This application claims priority to and the benefit of Japanese Patent Application No. 2021-029651 filed Feb. 26, 2021, and Japanese Patent Application No. 2021-124464 filed Jul. 29, 2021, the entire contents of which are incorporated herein by reference.
The present invention relates to phenylacetic acid derivatives, use and production intermediate of the same.
Patent Literature 1 describes phenylacetic acid derivatives.
Patent Literature 1: EP 0422597 A2
An object of the present invention is to provide a compound having excellent efficacy for controlling pests.
The present inventor has intensively studied to find out a compound having an excellent efficacy for controlling a pest, and as a result, found that a compound represented by the following formula (I) has an excellent efficacy for controlling pests.
That is, the present invention encompasses the followings.
[1] A compound represented by formula (I):
[wherein
[3] The compound according to [2], or its N-oxide or salts thereof, wherein E represents a phenyl group, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the phenyl group, the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group H}, R5-C≡C—, R6O—, or a C5-C6 cycloalkenyl group.
[4] An agricultural composition which comprises the compound according to any one of [1] to [3] or salts thereof, and an inert carrier.
[5] A composition which comprises one or more ingredients selected from the group consisting of the following Groups (a), (b), (c) and (d), as well as the compound according to any one of [1] to [3] or its N-oxide or salts thereof:
[6] A method for controlling pests which comprises applying an effective amount of the compound according to any one of [1] to [3] or its N-oxide or salts thereof or an effective amount of the composition according to [5] to a plant or soil.
[7] A method for controlling soybean rust fungus having an amino acid substitution of F129L on mitochondrial cytochrome b protein, which comprises applying an effective amount of the compound according to any one of [1] to [3], or its N-oxide or salts thereof, or an effective amount of the composition according to [5] to a soybean or soil where the soybean grows.
[8] Use of the compound according to any one of [1] to [3], or its N-oxide or salts thereof, or the composition according to [5] for controlling a pest.
[9] A seed or vegetative reproductive organ carrying an effective amount of the compound according to any one of [1] to [3] or its N-oxide or salt thereof or an effective amount of the composition according to [5].
[10] A compound represented by formula (IT):
[wherein
The present invention can control pests.
The substituents as used herein are explained as follows.
The term “halogen atom” represents a fluorine atom, a chlorine atom, a bromine atom, or an iodine atom.
When a substituent has two or more halogen atoms, the halogen atoms may be identical to or different from each other.
When a substituent has two or more groups or atoms selected from particular groups (for example, a group selected from a C1-C3 alkyl group and a halogen atom), each of the groups or the atoms may be identical to or different from each other.
The expression of “which may be optionally substituted with one or more substituents selected from Group X (wherein X means any one of A, B, C, D, E, F, G, H, I, J, or K)” represents that when two or more of the substituents selected from Group X are existed, the substituents may be identical to or different from each other.
The expression “CX-CY” as used herein represents that the number of carbon atoms is from X to Y. For example, the expression “C1-C6” represents that the number of carbon atoms is from 1 to 6.
The term “chain hydrocarbon group” represents an alkyl group, an alkenyl group, or an alkynyl group.
Examples of the “alkyl group” include methyl group, ethyl group, propyl group, isopropyl group, 1,1-dimethylpropyl group, 1,2-dimethylpropyl group, butyl group, sec-butyl group, tert-butyl group, pentyl group, hexyl group, and decyl group.
Examples of the “alkenyl group” include vinyl group, 1-propenyl group, 2-propenyl group, 1-methyl-1-propenyl group, 1-methyl-2-propenyl group, 1,2-dimethyl-1-propenyl group, 3-butenyl group, 4-pentenyl group, 5-hexenyl group, and 9-decenyl group.
Examples of the “alkynyl group” include ethynyl group, 1-propynyl group, 2-propynyl group, 1-methyl-2-propynyl group, 1,1-dimethyl-2-propynyl group, 2-butynyl group, 4-pentynyl group, 5-hexynyl group, and 9-decynyl group.
Examples of the “alkoxy group” include methoxy group, ethoxy group, propoxy group, isopropoxy group, butoxy group, tert-butoxy group, pentyloxy group, and hexyloxy group.
Examples of the “alkylthio group” includes methylthio group, ethylthio group, propylthio group, isopropylthio group, butylthio group, tert-butylthio group, pentylthio group, and hexylthio group.
Examples of the “cycloalkyl group” include cyclopropyl group, cyclobutyl group, cyclopentyl group, and cyclohexyl group.
Examples of the “cycloalkenyl group” include cyclopentenyl group, and cyclohexenyl group.
Examples of the “aryl group” include phenyl group, indenyl group, indanyl group, naphthyl group, and tetrahydronaphthyl group.
Examples of the “aromatic heterocyclic group” include pyrrolyl group, furyl group, thienyl group, pyrazolyl group, imidazolyl group, triazolyl group, tetrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, oxadiazolyl group, thiadiazolyl group, pyridyl group, pyridazinyl group, pyrimidinyl group, pyrazinyl group, triazinyl group, tetrazinyl group, indolyl group, indazolyl group, benzimidazolyl group, imidazopyridyl group, benzothiophenyl group, benzofuranyl group, quinolyl group, isoquinolyl group, quinazolinyl group, and quinoxalinyl group.
The term(s) as described herein is/are explained.
The term of “soybean rust fungus having an amino acid substitution of F129L on mitochondrial cytochrome b protein” represents soybean rust fungus (scientific name: Phakopsora pachyrhizi) which shows a resistance against QoT fungicide by having a mutation in the mitochondrial cytochrome b gene encoding mitochondrial cytochrome protein and as a result of the mutation, causing amino acid substitution of F129L.
The present compound and the intermediate compound A may be existed as one or more stereoisomers. Examples of the stereoisomer include enantiomer, diastereoisomer, atropisomer, and geometric isomer. Each stereoisomer, and stereoisomer mixture(s) in an arbitrary ratio thereof are included in the present invention.
Examples of the geometric isomer include the below-mentioned structures.
The present compound N or its N-oxide may form an acid additional salts thereof such as hydrochloride salt, sulfate, nitrate, phosphate, acetate, and benzoate by mixing it with an acid such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, and benzoic acid.
Embodiments of the compound N of the present invention include the following compounds.
[Embodiment 1] The compound N of the present invention wherein E represents R3—O—N═C(R4)—.
[Embodiment 2] The compound according to the Embodiment 1 wherein R3 represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be optionally substituted with one or more substituents selected from C3-C4 cycloalkyl group and a halogen atom}, or R7CH2—, R4 represents a methyl group or a hydrogen atom, and R7 represents a phenyl group or a five- to six- membered aromatic heterocyclic group {the phenyl group, and the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group K},
[Embodiment 3] The compound N of the present invention wherein E represents R5-C≡C—.
[Embodiment 4] The compound according to the Embodiment 3 wherein R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
[Embodiment 5] The compound N of the present invention wherein E represents R6O—.
[Embodiment 6] The compound according to the Embodiment 5 wherein R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 7] The compound N of the present invention wherein E represents a phenyl group which may be optionally substituted with one or more substituents selected from Group A.
[Embodiment 8] The compound N of the present invention wherein E represents a phenyl group which may be optionally substituted with one or more substituents selected from Group H.
[Embodiment 9] The compound N of the present invention wherein E represents a five- to six- membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group B.
[Embodiment 10] The compound N of the present invention wherein E represents a five- to six- membered aromatic heterocyclic group which may be optionally substituted with one or more substituents selected from Group H.
[Embodiment 11] The compound N of the present invention wherein E represents a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group H}.
[Embodiment 12] The compound N of the present invention wherein E represents a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}.
[Embodiment 13] The compound N of the present invention wherein E represents a C5-C6 cycloalkenyl group.
[Embodiment 14] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}, a C5-C6 cycloalkenyl group, R3—O—N═C(R4)—, R5—C≡C—, or R6O—, R3 represents a C1-C6 chain hydrocarbon group {the C1-C6 chain hydrocarbon group may be optionally substituted with one or more substituents selected from a C3-C4 cycloalkyl group and a halogen atom}, or R7CH2—, R4 represents a methyl group or a hydrogen atom, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group, and R7 represents a phenyl group or a five- to six-membered aromatic heterocyclic group {the phenyl group, and the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group K}.
[Embodiment 15] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, a five- to six- membered aromatic heterocyclic group {the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group H}, a C3-C7 cycloalkenyl group which may be optionally substituted with one or more substituents selected from Group C, R5—C≡C—, or R6O—, and R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms}.
[Embodiment 16] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}, a C5-C6 cycloalkenyl group, a R5-C≡C—, or R6O—, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 17] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, a five- to six- membered aromatic heterocyclic group {the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group H}, R5—C≡C—, or R6O—and R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms}.
[Embodiment 18] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}, R5—C≡C—, or R6O—, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 19] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, a five- to six- membered aromatic heterocyclic group {the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group H}, or R5—C≡C—, and R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms}.
[Embodiment 20] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}, or R5—C≡C—, and R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
[Embodiment 21] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, a five- to six- membered aromatic heterocyclic group {the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group H}, or R6O—.
[Embodiment 22] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}, or R6O—, and R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 23] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, R5—C≡C—, or R6O—, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms.
[Embodiment 24] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, R5—C≡C—, or R6O—, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group, and R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 25] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, or a five- to six- membered aromatic heterocyclic group {the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group H}.
[Embodiment 26] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, a pyridyl group, a thienyl group, a thiazolyl group, or a pyrazolyl group {the pyridyl group, the thienyl group, the thiazolyl group, and the pyrazolyl group may be optionally substituted with one or more substituents selected from Group K}.
[Embodiment 27] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, or R5—C≡C—, R5 represents a C1-C6 chain hydrocarbon group or C3-C6 cycloalkyl group {the C1-C6 chain hydrocarbon group, and the C3-C6 cycloalkyl group may be optionally substituted with one or more halogen atoms}.
[Embodiment 28] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, or R5—C≡C—, R5 represents a C1-C6 chain hydrocarbon group or a C3-C6 cycloalkyl group.
[Embodiment 29] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group A}, or R6O—.
[Embodiment 30] The compound N of the present invention wherein E represents a phenyl group {the phenyl group may be optionally substituted with one or more substituents selected from Group H}, or R6O—, and R6 represents a C2-C6 chain hydrocarbon group which may be optionally substituted with one or more substituents selected from Group I, or a C3-C4 cycloalkyl group.
[Embodiment 31] The compound N of the present invention wherein X represents CH, and L represents an oxygen atom.
[Embodiment 32] The compound according to the Embodiment 1 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 33] The compound according to the Embodiment 2 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 34] The compound according to the Embodiment 3 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 35] The compound according to the Embodiment 4 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 36] The compound according to the Embodiment 5 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 37] The compound according to the Embodiment 6 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 38] The compound according to the Embodiment 7 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 39] The compound according to the Embodiment 8 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 40] The compound according to the Embodiment 9 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 41] The compound according to the Embodiment 10 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 42] The compound according to the Embodiment 11 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 43] The compound according to the Embodiment 12 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 44] The compound according to the Embodiment 13 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 45] The compound according to the Embodiment 14 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 46] The compound according to the Embodiment 15 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 47] The compound according to the Embodiment 16 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 48] The compound according to the Embodiment 17 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 49] The compound according to the Embodiment 18 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 50] The compound according to the Embodiment 19 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 51] The compound according to the Embodiment 20 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 52] The compound according to the Embodiment 21 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 53] The compound according to the Embodiment 22 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 54] The compound according to the Embodiment 23 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 55] The compound according to the Embodiment 24 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 56] The compound according to the Embodiment 25 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 57] The compound according to the Embodiment 26 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 58] The compound according to the Embodiment 27 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 59] The compound according to the Embodiment 28 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 60] The compound according to the Embodiment 29 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 61] The compound according to the Embodiment 30 wherein X represents CH, and L represents an oxygen atom.
[Embodiment 62] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom.
[Embodiment 63] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a methyl group, a methoxy group, or a halogen atom.
[Embodiment 64] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a methyl group.
[Embodiment 65] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R2 represents a C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom.
[Embodiment 66] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R2 represents a methyl group, a methoxy group, or a halogen atom.
[Embodiment 67] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R2 represents a methyl group.
[Embodiment 68] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 and R2 are identical to or different from each other and each represents a C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom.
[Embodiment 69] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a methyl group, a methoxy group, or a halogen atom, R2 represents a C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom.
[Embodiment 70] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a methyl group, and R2 represents a C1-C3 alkyl group which may be optionally substituted with one or more halogen atoms, a methoxy group, or a halogen atom.
[Embodiment 71] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 and R2 are identical to or different from each other and each represents a methyl group, a methoxy group, or a halogen atom.
[Embodiment 72] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 represents a methyl group, and R2 represents a methyl group, a methoxy group, or a halogen atom.
[Embodiment 73] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein R1 and R2 represent a methyl group.
[Embodiment 74] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein n is 1.
[Embodiment 75] The compound according to Embodiment 68 wherein n is 1.
[Embodiment 76] The compound according to Embodiment 69 wherein n is 1.
[Embodiment 77] The compound according to Embodiment 70 wherein n is 1.
[Embodiment 78] The compound according to Embodiment 71 wherein n is 1.
[Embodiment 79] The compound according to Embodiment 72 wherein n is 1.
[Embodiment 80] The compound according to Embodiment 73 wherein n is 1.
[Embodiment 81] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 82] The compound according to the Embodiments 68 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 83] The compound according to the Embodiments 69 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 84] The compound according to the Embodiments 70 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 85] The compound according to the Embodiments 71 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 86] The compound according to the Embodiments 72 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 87] The compound according to the Embodiments 73 wherein n is 1, and R2 binds at the 4-position or the 5-position.
[Embodiment 88] The compound according to any one of the Embodiments 1 to 61 or the compound N of the present invention wherein n is 1, and R2 binds at the 4-position.
[Embodiment 89] The compound according to the Embodiment 68 wherein n is 1, and R2 binds at the 4-position.
[Embodiment 90] The compound according to the Embodiment 69 wherein n is 1, and R2 binds at the 4-position.
[Embodiment 91] The compound according to the Embodiment 70 wherein n is 1, and R2 binds at the 4-position.
[Embodiment 92] The compound according to the Embodiment 71 wherein n is 1, and R2 binds at the 4-position.
[Embodiment 93] The compound according to the Embodiment 72 wherein n is 1, and R2 binds at the 4-position.
[Embodiment 94] The compound according to the Embodiment 73 wherein n is 1, and R2 binds at the 4-position.
The compound N of the present invention wherein n is 1 and R4 binds at the 4-position represents the compound represented by formula (I-4):
[wherein the symbols are the same as defined in [1]].
The compounds according to the Embodiments 88 to 94 can be described also by the formula (T-4).
Next, a process for preparing a compound of the present invention is explained.
A compound represented by formula (A1) (hereinafter, referred to as Compound (A1)) can be prepared by reacting a compound represented by formula (B1) (hereinafter, referred to as Compound (B1)) with a compound represented by formula (M1) (hereinafter, referred to as Compound (M1)) in the presence of a palladium catalyst and a base.
[wherein, E1 represents a C6-C10 aryl group, or a five- to ten- membered aromatic heterocyclic group {the C6-C10 aryl group, and the five- to ten- membered aromatic heterocyclic group each may be optionally substituted with one or more substituents selected from Group A}, M1 represents B(OH)2 or 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl group, and X1 represents a leaving group such as a chlorine atom, a bromine atom, an iodine atom and a trifuryloxy group, and the other symbols are the same as defined above].
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons such as hexane, toluene, and xylene (hereinafter, collectively referred to as hydrocarbons); methyl tert-butyl ether (hereinafter, referred to as MTBE), tetrahydrofuran (hereinafter, referred to as THE), ethers such as dimethoxyethane (hereinafter, collectively referred to as ethers); halogenated hydrocarbons such as chloroform and chlorobenzene (hereinafter, collectively referred to as halogenated hydrocarbons); amides such as dimethylformamide (hereinafter, referred to as DMF) and N-methyl pyrrolidone (hereinafter, referred to as NMP) (hereinafter, collectively referred to as amides); esters such as methyl acetate and ethyl acetate (hereinafter, collectively referred to as esters); nitriles such as acetonitrile and propionitrile (hereinafter, collectively referred to as nitriles); water, and mixed solvents of two or more kinds of the solvents.
Examples of the palladium catalyst to be used in the reaction include palladium catalysts such as tris(dibenzylideneacetone)dipalladium(O) (hereinafter, referred to as Pd2 (dba)3), tetrakis(triphenylphosphine)palladium(O) (hereinafter, referred to as Pd(PPh3)4), and {1,1′-bis(diphenylphosphino)ferrocene}palladium(II) dichloride (hereinafter, referred to as PdCl2(dppf)).
Examples of the bases to be used in the reaction include organic bases such as triethylamine and pyridine (hereinafter, referred to as organic bases); alkali metal carbonates such as sodium carbonate and potassium carbonate (hereinafter, referred to as alkali metal carbonates); alkali metal hydrocarbonates (such as sodium hydrocarbonates and potassium hydrocarbonates) (hereinafter, referred to as alkali metal hydrocarbonates); sodium fluoride and tripotassium phosphate.
In the reaction, as needed, a ligand may be used. Examples of the ligand to be used in the reaction include triphenylphosphine, Xantphos, 2,2′-bis(diphenylphoshino)-1,1′-binaphthyl, 1,1′-bis(diphenylphoshino)ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, and 1,2-bis(diphenylphosphino)ethane. When the ligand is used in the reaction, the ligand is used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (B1).
In the reaction, the compound (M1) is used within a range of 1 to 10 molar ratio(s), and the palladium catalyst is used within a range of 0.01 to 1 molar ratio(s), and the base is used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B1).
The reaction temperature is usually within a range of 0 to 150° C. The reaction period is usually within a range of 0.1 to 120 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the compound (A1).
The compound (M1) is publicly known, or can be prepared according to a publicly known method.
The compound (A1) can be prepared by reacting a compound represented by formula (B2) (hereinafter, referred to as Compound (B2)) with a compound represented by formula (M2) (hereinafter, referred to as Compound (M2)) in the presence of a palladium catalyst and a base.
[wherein the symbols are the same as defined above.]
The reaction can be carried out by using the compound (M2) in place of the Compound (B1) and by using the compound (B2) in place of the compound (M1) according to the Process A.
The compound (M2) is publicly known, or can be prepared according to a publicly known method.
A compound represented by formula (A2) (hereinafter, referred to as Compound (A2)) can be prepared by reacting the Compound (B1) with a compound represented by formula (M3) (hereinafter, referred to as Compound (M3)) in the presence of a metallic catalyst and a base.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the metallic catalysts to be used in the reaction include bis(triphenylphosphine)palladium(II) dichloride and copper(I) iodide.
Examples of the bases to be used in the reaction include organic bases.
In the reaction, the compound (M3) is used within a range of 1 to 10 molar ratio(s), and the metallic catalyst is used within a range of 0.01 to 1 molar ratio(s), and the base is used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B1).
The reaction temperature is usually within a range of 0 to 150° C. The reaction period is usually within a range of 0.1 to 120 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the compound (A2).
The compound (M3) is publicly known, or can be prepared according to a publicly known method.
Process D A compound represented by formula (A3) (hereinafter, referred to as Compound (A3)) can be prepared by reacting a compound represented by formula (B3) (hereinafter, referred to as Compound (B3)) with a compound represented by formula (M4) (hereinafter, referred to as Compound (M4)) or salts thereof.
[wherein the symbols are the same as defined above.]
Examples of the salts of the compound (M4) include hydrochloride salts and sulfate salts thereof.
The reaction is usually carried out in a solvent. Examples of the solvents to be used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; alcohols such as methanol and ethanol (hereinafter, collectively referred to as alcohols); and mixed solvents of two or more kinds of these solvents.
In the reaction, as needed, a base may be added. Examples of the bases to be used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrocarbonates; sodium hydride and tripotassium phosphate. When the base is used in the reaction, the base is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B3).
In the reaction, the compound (M4) is usually used within a range of 1 to 10 molar ratio(s) as opposed to 1 mole of the compound (B3).
The reaction temperature is usually within a range of 0 to 150° C. The reaction period is usually within a range of 0.1 to 120 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the Compound (A3).
Also the compound (A3) can be prepared according to the method described in WO 98/043949 A1.
The compound (M4) is publicly known, or can be prepared according to a publicly known method.
Process E The compound (A3) can be prepared by reacting a compound represented by formula (B4) (hereinafter, referred to as Compound (B4)) with a compound represented by formula (M5) (hereinafter, referred to as Compound (M5)) in the presence of a base.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the bases include organic bases, alkali metal carbonates, alkali metal hydrocarbonates, sodium hydride, and tripotassium phosphate.
In the reaction, the compound (M5) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B4).
The reaction temperature is usually within a range of −20 to 150° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the Compound (A3).
The Compound (M5) is publicly known, or can be prepared according to a publicly known method.
A compound represented by formula (A4) (hereinafter, referred to as Compound (A4)) can be prepared by reacting the Compound (B1) with a compound represented by formula (M6) (hereinafter, referred to as Compound (M6)) in the presence of a metallic catalyst and a base.
[wherein Z1 represents a nitrogen atom or CR51, Z2 represents a nitrogen atom or CR52, Z3 represents a nitrogen atom or CR53, Z4 represents a nitrogen atom or CR54 (with the proviso that the case where all of Z1, Z2, Z3, and Z4 are a nitrogen atom is excluded), R51, R52, R53, and R54 are identical to or different from each other and each represents a C3-C6 cycloalkyl group which may be optionally substituted with one or more substituents selected from Group E, a C1-C6 chain hydrocarbon group, a C1-C3 alkylthio group (the C1-C6 chain hydrocarbon group, and the C1-C3 alkylthio group may be optionally substituted with one or more substituents selected from Group G}, a phenyl group, a five- to six-membered aromatic heterocyclic group (the phenyl group, and the five- to six- membered aromatic heterocyclic group may be optionally substituted with one or more substituents selected from Group F}, OR13, C(O)R8, C(O)OR8, C(O)NR8R9, NR8R9, C(R11)═N—OR12, a halogen atom, a cyano group, a nitro group, or a hydrogen atom, and the other symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, hydrocarbons, amides, water, and mixed solvents of two or more kinds of these solvents.
Examples of the metallic catalysts to be used in the reaction include copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, copper(I) trifluoromethanesulfonate benzene complex, tetrakis(acetonitrile) copper(I) hexafluorophosphate, and copper(I) 2-thiophenecarboxylate; and nickel catalysts such as bis(1,5-cyclooctadiene)nickel(O) and nickel(II) chloride.
Examples of the bases include organic bases, alkali metal carbonates, alkali metal hydrocarbonates, sodium fluoride and tripotassium phosphate.
In the reaction, as needed, a ligand and/or an alkali metal halide may be used.
Examples of the ligand include triphenylphosphine, Xantphos, 2,2′-bis(diphenylphoshino)-1,1′-binaphthyl, 1,1′-bis(diphenylphoshino)ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 1,2-bis(diphenylphosphino)ethane, 2,2′-bipyridine, 2-aminoethanol, 8-hydroxyquinoline, 1,10-phenanthroline, trans-1,2-cyclohexanediamine, trans-N,N′-dimethylcyclohexane-1,2-diamine, and N,N′-dimethylethylenediamine. When a ligand is used in the reaction, the ligand is usually used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (B1).
Examples of the alkali metal halides include potassium fluoride, sodium fluoride, lithium chloride, and sodium chloride. When the alkali metal halide is used in the reaction, the alkali metal halide is usually used within a range of 0.1 to 5 molar ratios as opposed to 1 mole of the compound (B1).
In the reaction, the Compound (M6) is usually used within a range of 1 to 10 molar ratio(s), the metallic catalyst is usually used within a range of 0.01 to 2 molar ratios, and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B1).
The reaction temperature of the reaction is usually within a range of −20 to 200° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the compound (A4).
The Compound (M6) is publicly known, or can be prepared according to a publicly known method.
A compound represented by formula (A5) (hereinafter, referred to as Compound (A5)) can be prepared by reacting a compound represented by formula (B5) (referred to as Compound (B5)) with a compound represented by formula (M7) (hereinafter, referred to as Compound (M7)) in the presence of phosphines and azodiesters.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; nitriles; and mixed solvents of two or more kinds of these solvents.
Examples of the phosphines include triphenylphosphine and trimethylphosphine.
Examples of the azodiesters include diethyl azodicarboxylate, diisopropyl azodicarboxylate, and bis(2-methoxyethyl) azodicarboxylate.
In the reaction, the Compound (M7) is usually used within a range of 1 to 10 molar ratio(s), the phosphines is usually used within a range of 1 to 10 molar ratio(s), and the azodiesters is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the Compound (B5).
The reaction temperature of the reaction is usually within a range of 0 to 150° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic solvents are worked up (for example, drying and concentration) to isolate the compound (A5).
The compound (M7) is publicly known, or can be prepared according to a publicly known method.
The compound (A5) can be prepared by reacting the compound (B5) with a compound represented by formula (M8) (hereinafter, referred to as Compound (M8)) in the presence of a base.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the base include organic bases, alkali metal carbonates, alkali metal hydrocarbonates, sodium hydride and tripotassium phosphate.
In the reaction, the compound (M8) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B5).
The reaction temperature is usually within a range of −20 to 150° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, the reaction mixtures are extracted with organic solvent (s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (A5).
The compound (M8) is publicly known, or can be prepared according to a publicly known method.
A compound represented by formula (A6) (hereinafter, referred to as Compound (A6)) can be prepared by a step of reacting a compound represented by formula (B6) (hereinafter, referred to as Compound (B6)) with a compound represented by formula (M9) (hereinafter, referred to as Compound (M9)) in the presence of a base to obtain a compound represented by formula (B7)) (hereinafter, referred to as Compound (B7)) (hereinafter, the step is referred to as Step (I-1)), followed by a step of reacting the compound (B7) with a compound represented by formula (M10) (hereinafter, referred to as Compound (M10)) in the presence of a base (hereinafter, the step is referred to as Step (I-2)).
[wherein R55 represents a C1-C4 alkyl group, X2 represents an iodine atom, a methoxysulfonyloxy group, a mesyloxy group, or a tosyloxy group, and the other symbols are the same as defined above.]
The Step (I-1) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, amides, and mixed solvents of two or more kinds of these solvents.
Examples of the bases to be used in the reaction include sodium hydride.
In the reaction, the compound (M9) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 0.5 to 5 molar ratio(s), as opposed to 1 mole of the compound (B6).
The reaction period is usually within a range of 5 minutes to 72 hours. The reaction temperature is usually within a range of −20 to 100° C.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (B7).
The compound (M9) is a commercially available compound, or can be prepared according to a publicly known method.
The Step (I-2) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the bases to be used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrocarbonates, and sodium hydride.
In the reaction, the compound (M10) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 20 molar ratio(s), as opposed to 1 mole of the compound (B7).
The reaction temperature is usually within a range of −20 to 100° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (A6).
The compound (M10) is a commercially available compound, or can be prepared according to a publicly known method.
A compound represented by formula (A7) (hereinafter, referred to as Compound (A7)) can be prepared by a step of reacting a compound represented by formula (B26) (hereinafter, referred to as Compound (B26)) with a compound represented by formula (M12) (hereinafter, referred to as Compound (M12)) in the presence of a base to obtain a compound represented by formula (B9)) (hereinafter, referred to as Compound (B9)) (hereinafter, the step is referred to as Step (K-1)), followed by a step of reacting the compound (B9) with the compound (B10) in the presence of a base (hereinafter, the step is referred to as Step (K-2)).
[wherein R56 represents a tert-butyl group or an isopentyl group, and the other symbols are the same as defined above.]
The Step (K-1) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include ethers, amides, alcohols, and mixed solvents of two or more kinds of these solvents.
Examples of the base to be used in the reaction include sodium hydride; and alkali metal alkoxides such as sodium methoxide, sodium ethoxide, potassium t-butoxide (hereinafter, referred to as alkali metal alkoxides).
In the reaction, the compound (M12) is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 5 molar ratio(s), as opposed to 1 mole of the compound (B6).
The reaction period is usually within a range of 5 minutes to 72 hours. The reaction temperature is usually within a range of −20 to 100° C.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (B9).
The compound (M12) is a commercially available compound, or can be prepared according to a publicly known method.
The step (K-2) can be carried out by using the compound (B9) in place of the compound (B7) according to the step (I-2) of the process I.
A compound represented by formula (A8) (hereinafter, referred to as Compound (A8)) can be prepared by reacting a compound represented by formula (B10) (hereinafter, referred to as Compound (B10)) with a compound represented by formula (M13) (hereinafter, referred to as Compound (M13)) in the presence of a catalyst and a base.
[wherein the symbols are the same as defined above.]
The reaction can be carried out by using the compound (M13) in place of the compound (B1), and using the compound (B10) in place of the compound (M1) according to the process A.
The compound (M13) is a publicly known compound, or can be prepared according to the publicly known method.
A N-oxide of the compound represented by formula (I) can be prepared by reacting the compound represented by formula (I) with an oxidizing agent. The reaction can be carried out according to the method described in U.S. 2018/0009778 A1 or WO 2016/121970 A1.
The compound (B7) can be prepared by a step of reacting the compound (B6) with a compound represented by formula (M1l) (hereinafter, referred to as Compound (M1l)) to obtain a compound represented by formula (B8) (hereinafter, referred to as Compound (B8)) (hereinafter, the step is referred to as Step (1-1)), followed by a step of subjecting the compound (M8) to a reaction in the presence of an acid to obtain the compound (B7) (hereinafter, the step is referred to as Step (1-2))
[wherein the symbols are the same as defined above.]
The step (1-1) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, halogenated hydrocarbons, ethers, amides, and mixed solvents of two or more kinds of these solvents.
In the reaction, the compound (M11) is usually used within a range of 1 to 10 molar ratio(s) as opposed to 1 mole of the compound (B6).
The reaction period is usually within a range of 5 minutes to 72 hours. The reaction temperature is usually within a range of −20 to 200° C.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to obtain the compound (B8).
The compound (M11) is a commercially available compound, or can be prepared according to a publicly known method.
The step (I-2) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixed solvents of two or more kinds of these solvents.
Examples of the acid to be used in the reaction include hydrochloric acid and acetic acid.
In the reaction, the acid is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 20 molar ratio(s), as opposed to 1 mole of the compound (B8).
The reaction temperature is usually within a range of −20 to 100° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (B7).
A compound represented by formula (B16) (hereinafter, referred to as Compound (B16)) can be prepared by a step of reacting a compound represented by formula (B11) (hereinafter, referred to as Compound (B11)) with a compound represented by formula (M14) (hereinafter, referred to as Compound (M14)) in the presence of a catalyst and a base to obtain a compound represented by formula (B12) (hereinafter, referred to as compound (B12)) (hereinafter, the step is referred to as Step (2-1)), followed by a step of subjecting the compound (B12) to a reaction in the presence of base to obtain a compound represented by formula (B13) (hereinafter, referred to as Compound (B13)) (hereinafter, the step is referred to as Step (2-2)), and a step of reacting the compound (B13) with the compound (M11) to obtain a compound represented by formula (B14) (hereinafter, referred to as Compound (B14)) (hereinafter, the step is referred to as Step (2-3)), and a step of subjecting the compound (B14) to the reaction in the presence of an acid to obtain a compound represented by formula (B15) (hereinafter, the step is referred to as Step (2-4)), and a step of reacting the compound (B15) with the compound (M10) in the presence of a base (hereinafter, the step is referred to as Step (2-5)).
[wherein the symbols are the same as defined above.]
The Step (2-1) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, water, and mixed solvents of two or more kinds of these solvents.
Examples of the catalysts to be used in the reaction include palladium catalyst such as palladium(II) acetate, Pd2(dba)2, Pd(PPh3)4, and PdCl2(dppf); and copper catalysts such as copper(I) iodide, copper(I) bromide, copper(I) chloride, copper(I) oxide, trifluoromethanesulfonate copper(I) benzene complex, tetrakis(acetonitrile) copper(I) hexafluorophosphate, and 2-thiophencarboxylate copper(I).
Examples of the base to be used in the reaction include organic bases; alkali metal carbonates; alkali metal hydrocarbonates; alkali metal phosphates such as tripotassium phosphate (hereinafter, referred to as alkali metal phosphates); and acetates such as sodium acetate (hereinafter, referred to as acetates).
In the reaction, as needed, a ligand may be used. Examples of the ligand to be used in the reaction include triphenylphosphine, Xantphos, 2,2′-bis(diphenylphoshino)-1,1′-binaphthyl, 1,1′-bis(diphenylphoshino)ferrocene, 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl, 2-di-tert-butylphoshino-2′,4′,6′-triisopropyl-1,1′-biphenyl, tri-tert-butylphosphine, 1,2-bis(diphenylphosphino)ethane, pyridine-2-carboxlic acid, (L)-proline, trans-1,2-cyclohexane diamine, trans-N,N′-dimethylcyclohexane-1,2-diamine, N,N′-dimethylethylenediamine, N,N-dimethylglycine hydrochloride salt. When the ligand is used in the reaction, the ligand is usually used within a range of 0.01 to 1 molar ratio(s) as opposed to 1 mole of the compound (B11).
In the reaction, the compound (M14) is usually used within a range of 0.1 to 10 molar ratio(s), the catalyst is usually used within a range of 0.01 to 1 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the compound (B11).
The reaction period is usually within a range of 5 minutes to 72 hours. The reaction temperature is usually within a range of −20 to 200° C.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (B12).
The compound (M14) is a publicly compound, or can be prepared according to a publicly known method.
The step (2-2) is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixed solvents of two or more kinds of these solvents.
Examples of the base to be used in the reaction include alkali metal phosphates and alkali metal alkoxides.
In the reaction, the base is usually used within a range of 1 to 20 as opposed to 1 mole of the compound (B12).
The step (2-3) can be carried out by using the compound (B13) in place of the compound (B6) according to the step (1-1) of the Reference process 1.
The step (2-4) can be carried out by using the compound (B14) in place of the compound (B8) according to the step (1-2) of the Reference process 1.
The step (2-5) can be carried out by using the compound (B15) in place of the compound (B7) according to the step (2-1) of the Process I.
A compound represented by formula (B18) (hereinafter, referred to as Compound (B18)) can be prepared by a step of reacting a compound represented by formula (B27) (hereinafter, referred to as Compound (B27)) with the compound (M12) in the presence of a base to obtain a compound represented by formula (B17) (hereinafter, referred to as Compound (B17)) (hereinafter, the step is referred to as Step (3-1)), followed by a step of reacting the compound (B17) with the compound (M10) in the presence of a base (hereinafter, the step is referred to as Step (3-2)).
[wherein the symbols are the same as defined above.]
The step (3-1) can be carried out by using the compound (B27) in place of the compound (B26) according to the step (K-1) of the Process K.
The step (3-2) can be carried out by using the compound (B17) in place of the compound (B9) according to the step (K-2) of the Process K.
The compound (B2) can be prepared by reacting the compound (B1) with diboronic acid or diboronate in the presence of a base and a palladium catalyst.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent.
Examples of the solvent to be used in the reaction include hydrocarbons; ethers; halogenated hydrocarbons; amides; esters; sulfoxides such as dimethyl sulfoxide (hereinafter, referred to as DMSO) (hereinafter, referred to as Sulfoxides); nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the base to be used in the reaction include organic bases, alkali metal carbonates, alkali metal hydrocarbonates, acetates, and tripotassium phosphate.
Examples of the palladium catalyst include PdCl2(dppf).
Examples of the diboronic acid or diboronate include bis(pinacolato)diboron, and tetrahydroxydiboron.
In the reaction, the diboronic acid or the diboronate is usually used within a range of 1 to 5 molar ratio(s), the base is usually used within a range of 1 to 5 molar ratio(s), and the palladium catalyst is usually used within a range of 0.01 to 0.5 molar ratios, as opposed to 1 mole of the compound (B1).
The reaction temperature is usually within a range of 0 to 150° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water is added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (B2).
The compound (B5) can be prepared by oxidizing the compound (B2).
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, alcohols, water, and mixed solvents of two or more kinds of these solvents.
Examples of the oxidizing agent to be used in the reaction include meta-chloroperoxybenzoic acid and hydrogen peroxide water.
When hydrogen peroxide water is used as an oxidizing agent, as needed, a base may be added.
Examples of the base include sodium hydroxide and potassium hydroxide.
In the reaction, the oxidizing agent is usually used within a range of 1 to 5 molar ratio(s) as opposed to 1 mole of the compound (B2).
When the base is used in the reaction, the base is usually used within a range of 0.1 to 5 molar ratio(s) as opposed to 1 mole of the compound (B2).
The reaction temperature is usually within a range of −20 to 120° C. The reaction period is usually within a range of 0.1 to 48 hours.
When the reaction is completed, water and a reducing agent such as sodium thiosulfate are added to the reaction mixtures, and the reaction mixtures are extracted with organic solvent(s), and the organic layers are worked up (for example, drying and concentration) to isolate the compound (B5).
The compound (B5) can be prepared by a step of reacting a compound represented by formula (B19) (hereinafter, referred to as Compound (B19)) with a diboronic acid or a diboronate in the presence of a base and a palladium catalyst to obtain a compound represented by formula (B20) (hereinafter, referred to as Compound (B20)) (hereinafter, the step is referred to as Step (6-1)), followed by a step of reacting the compound (B20) with the compound (M13) in the presence of a base and a metallic catalyst (hereinafter, the step is referred to as Step (6-2)).
[wherein the symbols are the same as defined above.]
The step (6-1) can be carried out by using the compound (B19) in place of the compound (B1) according to the Reference process 4.
The compound (B19) is a publicly known compound, or can be prepared according to the publicly known method.
The step (6-2) can be carried out by using the compound (B20) in place of the compound (M1) and using the compound (M13) in place of the compound (B1) according to the Process A.
A compound represented by formula (B21) (hereinafter, referred to as compound (B21)) can be prepared by reacting the compound (B5) with a trifluoroacetic anhydride in the presence of a base.
[wherein the symbols are the same as defined above.]
The reaction is usually carried out in a solvent. Examples of the solvent to be used in the reaction include hydrocarbons, ethers, halogenated hydrocarbons, amides, esters, nitriles, and mixed solvents of two or more kinds of these solvents.
Examples of the base include organic bases.
In the reaction, the trifluoroacetic anhydride is usually used within a range of 1 to 10 molar ratio(s), and the base is usually used within a range of 1 to 10 molar ratio(s), as opposed to 1 mole of the Compound (B5).
The reaction temperature is usually within a range of −20 to 100° C. The reaction period is usually within a range of 0.1 to 48 hours.
The compound (B22) can be prepared by reacting the compound (B1) with a compound represented by formula (M15) (hereinafter, referred to as Compound (M15)).
[wherein R57 represents a methyl group or an ethyl group, and the other symbols are the same as defined above.]
The reaction can be carried out, for example, according to the method described in WO 2016/123253 A1.
The compound (M15) is a commercially available compound, or can be prepared according to a publicly known method.
The compound (B4) can be prepared by reacting the compound (B3) with hydroxylamine or salts thereof.
[wherein the symbols are the same as defined above.]
Examples of a salt of the hydroxylamine include hydrochloride salt and sulfate.
The reaction can be carried out by using hydroxylamine or salts thereof in place of the compound (M4) according to the Process D.
A compound represented by formula (B23) can be prepared by reacting the compound (B1) with N-formylsaccharin in the presence of a palladium catalyst, a ligand, triethylsilane, and a base.
[wherein the symbols are the same as defined above.]
The reaction can be carried out according to the method described in Angew. Chem. Int. Ed., 2013, 52, 8611-8615 and the others.
A compound represented by formula (B24) can be prepared by reacting the compound (B27) with the compound (M1) in the presence of a palladium catalyst and a base.
[wherein the symbols are the same as defined above.]
The reaction can be carried out by using the compound (B27) in place of the compound (B1) according to the Process A.
A compound represented by formula (B25) can be prepared by reacting the compound (B27) with the compound (M3) in the presence of a metallic catalyst and a base.
[wherein the symbols are the same as defined above.]
The reaction can be carried out by using the compound (B27) in place of the compound (B1) according to the Process C.
The Present compound may be mixed with or used in combination with one or more ingredient(s) selected from the group consisting of the following Group (a), Group (b), Group (c), and Group (d) (hereinafter referred to as “Present ingredient”).
When the Present compound is mixed with or used in combination with the Present ingredient, they are used simultaneously, separately, or at time intervals with each other.
When the Present compound is used simultaneously with the Present ingredient, the Present compound and the Present ingredient may be contained in separate formulations or contained in one formulation.
One aspect of the present invention provides a composition comprising one or more ingredient(s) selected from the group consisting of Group (a), Group (b), Group (c), and Group (d), and the Present compound (hereinafter referred to as “Composition A”).
Group (a) is a group consisting of acetylcholinesterase inhibitors (for example, carbamate insecticides and organophosphate insecticides), GABA-gated chloride channel blockers (for example, phenylpyrazole insecticides), sodium channel modulators (for example, pyrethroid insecticides), nicotinic acetylcholine receptor competitive modulators (for example, neonicotinoid insecticides), nicotinic acetylcholine receptor allosteric modulators, glutamate-gated chloride channel allosteric modulators (for example, macrolide insecticides), juvenile hormone mimics, multisite inhibitors, chordotonal organ TRPV channel modulators, mite growth inhibitors, microbial disruptors of insect midgut membranes, inhibitors of mitochondrial ATP synthase, uncouplers of oxidative phosphorylation, nicotinic acetylcholine receptor channel blockers (for example, nereistoxin insecticides), inhibitors of chitin biosynthesis, moulting disruptors, ecdysone receptor agonists, octopamine receptor agonists, mitochondrial complexes I, II, III, and IV electron transport inhibitors, voltage-dependent sodium channel blockers, inhibitors of acetyl CoA carboxylase, ryanodine receptor modulators (for example, diamide insecticides), chordotonal organ modulators, and microbial insecticides, and other insecticidal active ingredients, miticidal active ingredients, and nematicidal active ingredients. These ingredients are described in the classification on the basis of action mechanism by IRAC.
Group (b) is a group consisting of nucleic acids synthesis inhibitors (for example, phenylamide fungicides and acylamino acid fungicides), cell division and cytoskeleton inhibitors (for example, MBC fungicides), respiration inhibitors (for example, QoI fungicides, and QiI fungicides), amino acids synthesis and protein synthesis inhibitors (for example, anilino-pyrimidine fungicides), signal transduction inhibitors, lipid synthesis and membrane synthesis inhibitors, sterol biosynthesis inhibitors (for example, DMI fungicides such as triazole fungicides), cell wall biosynthesis inhibitors, melanin synthesis inhibitors, plant defense inducers, fungicides with multi-site contact activity, microbial fungicides, and other fungicidal active ingredients. These ingredients are described in the classification on the basis of action mechanism by FRAC.
Group (c) is a group of plant growth regulatory ingredients (including mycorrhizal fungi and root nodule bacteria).
Group (d) is a group of repellent ingredients.
Hereinafter, examples of the combination of the Present ingredient and the Present compound are described. For example, “alanycarb+SX” indicates a combination of alanycarb and SX.
The abbreviation of “SX” indicates any one of the Present compound selected from the Compound groups SX1 to SX259 described in Examples. Also, all of the following Present ingredient are known ingredients, and may be obtained from commercially available formulations, or may be prepared by known methods. When the Present ingredient is a microorganism, it may also be available from a bacterial authority depository. Further, the number in parentheses represents the CAS RN (registered trademark).
Combinations of the Present ingredient in the above Group (a) and the Present compound:
Combination of the Present ingredient in the above Group (b) and the Present compound:
Combination of the Present ingredient in the above Group (c) and the Present compound:
Combination of the Present ingredient in the above Group (d) and the Present compound:
The ratio of the Present compound to the Present ingredient includes, but not limited thereto, as a ratio by weight (the Present compound: the Present ingredient) 1,000:1 to 1:1,000, 500:1 to 1:500, 100:1 to 1:100, 50:1, 20:1, 10:1, 9:1, 8:1, 7:1, 6:1, 5:1, 4:1, 3:1, 2:1, 1:1, 1:2, 1:3, 1:4, 1:5, 1:6, 1:7, 1:8, 1:9, 1:10, 1:20, and 1:50, and the others.
The Present compound has an efficacy against pests. Examples of the pests include plant phytopathogenic microorganism, harmful arthropods such as harmful insects and harmful mites, harmful nematicides, and harmful mollusks.
The Present compound can control plant diseases caused by plant pathogenic microorganisms such as fungi, Oomycete, Phytomyxea, and bacteria. Examples of the fungi include Ascomycota, Basidiomycota, Blastocladiomycota, Chytridiomycota, Mucoromycota, and Olpidiomycota. Specific examples thereof include the followings. The scientific name of plant pathogenic microorganism which causes each disease is shown in parentheses.
Rice diseases:
The Present compound has control effect on harmful arthropods such as harmful insects and harmful mites, harmful nematodes, and harmful mollusks. Examples of the harmful arthropods, harmful nematodes, and harmful mollusks include the followings.
Lepidoptera:
Thysanura:
The harmful arthropods such as harmful insects and harmful mites, harmful mollusks and harmful nematodes may be those having a reduced susceptibility to or a developed resistance to an insecticide, a mitecide, a molluscicide or a nematicide.
The method for controlling pests of the present invention is carried out by applying an effective amount of the Present compound or the Composition A to a harmful pest directly and/or a habitat where the harmful pest lives (for example, plant, soil, an interior of a house, and animal).
Examples of a method for controlling pests of the present invention include foliar application, soil application, root application, shower application, smoking application, water-surface application, and seed application.
The Present compound or the Composition A is usually used by mixing it with inert carrier(s) such as solid carrier(s), liquid carrier(s), and gaseous carrier(s), surfactant(s), and the like, and as needed, adding thereto auxiliary agent(s) for formulation such as binder(s), dispersant(s), and stabilizer(s) to be formulated into an aqueous suspension formulation, an oily suspension formulation, an oil solution, an emulsifiable concentrate, an emulsion formulation, a microemulsion formulation, a microcapsule formulation, a wettable powder, a granular wettable powder, a dust formulation, a granule, a tablet, an aerosol formulation, a resin formulation, or the like. In addition to these formulations, the Present compound or the Composition A may be used by formulating it into a dosage form described in Manual on development and use of FAO and WHO Specifications for pesticides, FAO Plant Production and Protection Papers- 271-276, prepared by the FAO/WHO Joint Meeting on Pesticide Specifications, 2016, ISSN:0259-2517.
These formulations usually comprise 0.0001 to 99% by weight ratio of the Present compound or the Composition A.
Examples of the solid carrier include fine powders and granules of clays (for example, pyrophyllite clay and kaolin clay), talc, calcium carbonate, diatomaceous earth, zeolite, bentonite, acid white clay, attapulgite, white carbon, ammonium sulfate, vermiculite, perlite, pumice, silica sand, chemical fertilizers (for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, and ammonium chloride), and the others; as well as resins (for example, polyethylene, polypropylene, polyester, polyurethane, polyamide, and polyvinyl chloride).
Examples of the liquid carrier include water, alcohols (for example, ethanol, cyclohexanol, benzyl alcohol, propylene glycol, and polyethylene glycol), ketones (for example, acetone and cyclohexanone), aromatic hydrocarbons (for example, xylene, phenyl xylyl ethane, and methylnaphthalene), aliphatic hydrocarbons (for example, hexane and cyclohexane), esters (for example, ethyl acetate, methyl oleate, and propylene carbonate), nitriles (for example, acetonitrile), ethers (for example, ethylene glycol dimethyl ether), amides (for example, N,N-dimethylformamide and N,N-dimethyloctanamide), sulfoxides (for example, dimethyl sulfoxide), lactams (for example, N-methylpyrrolidone and N-octylpyrrolidone), fatty acids (for example, oleic acid), and vegetable oils (for example, soybean oil).
Examples of the gaseous carrier include fluorocarbon, butane gas, LPG (liquefied petroleum gas), dimethyl ether, nitrogen, and carbon dioxide.
Examples of the surfactant include nonionic surfactants (for example, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, and polyethylene glycol fatty acid esters), and anionic surfactants (for example, alkyl sulfonates, alkyl aryl sulfonates, and alkyl sulfates).
Examples of the other auxiliary agent for formulation include binders, dispersants, colorants, and stabilizers, and the specific examples thereof include polysaccharides (for example, starch, gum arabic, cellulose derivatives, and alginic acid), lignin derivatives, water-soluble synthetic polymers (for example, polyvinyl alcohol, polyvinyl pyrrolidone, and polyacrylic acids), acidic isopropyl phosphate, and dibutylhydroxytoluene.
Moreover, some adjuvants can be employed to improve or help the efficacy of the Present compound. The specific examples thereof include Nimbus (registered trademark), Assist (registered trademark), Aureo (registered trademark), Iharol (registered trademark), Silwet L-77 (registered trademark), BreakThru (registered trademark), SundancelI (registered trademark), Induce (registered trademark), Penetrator (registered trademark), AgriDex (registered trademark), Lutensol A8 (registered trademark), NP-7 (registered trademark), Triton (registered trademark), Nufilm (registered trademark), Emulgator NP7 (registered trademark), Emulad (registered trademark), TRITON X 45 (registered trademark), AGRAL 90 (registered trademark), AGROTIN (registered trademark), ARPON (registered trademark), EnSpray N (registered trademark), and BANOLE (registered trademark).
As used herein, examples of the plant include whole plant, stem and leaf, flower, ear, fruit, tree stem, branch, crown, seed, vegetative reproductive organ, and seedling.
A vegetative reproduction organ means a part of plant such as root, stem, and leaf which has a growth capability even when said part is separated from the plant body and placed into soil. Examples of the vegetative reproduction organ include tuberous root, creeping root, bulb, corm or solid bulb, tuber, rhizome, stolon, rhizophore, cane cuttings, propagule, and vine cutting. Stolon is also referred to as “runner”, and propagule is also referred to as “propagulum” and categorized into broad bud and bulbil.
Vine cutting means a shoot (collective term of leaf and stem) of sweet potato, glutinous yam, or the like. Bulb, corm or solid bulb, tuber, rhizome, cane cuttings, rhizophore, and tuberous root are also collectively referred to as “bulb”.
For example, cultivation of potato starts with planting a tuber into soil, and the tuber to be used is generally referred to as “seed potato”.
Examples of a method for controlling pests by applying an effective amount of the Present compound or the Composition A to soils include a method of applying an effective amount of the Present compound or the Composition A to soils before planting plants or after planting plants, a method of applying an effective amount of the Present compound or the Composition A to a root part of a crop to be protected from damage such as ingestion by harmful arthropods, and a method of controlling harmful arthropods that ingest a plant by permeating and transferring an effective amount of the Present compound or the Composition A from a root into the interior of the plant body. Specifically, examples of the application method include planting hole treatment (spraying into planting holes, soil mixing after planting hole treatment), plant foot treatment (plant foot spraying, soil mixing after plant foot treatment, irrigation at plant foot, plant foot treatment at a later seeding raising stage), planting furrow treatment (planting furrow spraying, soil mixing after planting furrow treatment), planting row treatment (planting row spraying, soil mixing after planting row treatment, planting row spraying at a growing stage), planting row treatment at the time of sowing (planting row spraying at the time of sowing, soil mixing after planting row treatment at the time of sowing), broadcast treatment (overall soil surface spraying, soil mixing after broadcast treatment), side-article treatment, treatment of water surface (application to water surface, application to water surface after flooding), other soil spraying treatment (spraying of a granular formulation on leaves at a growing stage, spraying under a canopy or around a tree stem, spraying on the soil surface, mixing with surface soil, spraying into seed holes, spraying on the ground surfaces of furrows, spraying between plants), other irrigation treatment (soil irrigation, irrigation at a seedling raising stage, chemical solution injection treatment, irrigation of a plant part just above the ground, chemical solution drip irrigation, chemigation), seedling raising box treatment (spraying into a seedling raising box, irrigation of a seedling raising box, flooding into a seedling raising box with chemical solution), seedling raising tray treatment (spraying on a seedling raising tray, irrigation of a seedling raising tray, flooding into a seedling raising tray with chemical solution), seedbed treatment (spraying on a seedbed, irrigation of a seedbed, spraying on a lowland rice nursery, immersion of seedlings), seedbed soil incorporation treatment (mixing with seedbed soil, mixing with seedbed soil before sowing, spraying at sowing before covering with soils, spraying at sowing after covering with soils, mixing with covering with soils), and other treatment (mixing with culture soil, plowing under, mixing with surface soil, mixing with soil at the place where raindrops fall from a canopy, treatment at a planting position, spraying of a granule formulation on flower clusters, mixing with a paste fertilizer).
Examples of the application to seeds (or seed treatments) include an application of the Present compound or the Composition A to seeds or vegetative reproductive organs, and specific examples thereof include spraying treatment in which a suspension of the Present compound or the Composition A is sprayed onto seed surface or the vegetative reproductive organ surface in the form of mist; smearing treatment in which the Present compound or the Composition A is coated a surface of seeds or the vegetative reproductive organ; a soaking treatment in which the seeds are soaked into the solution of the Present compound or the Composition A for a certain time; and a method for coating the seeds or the vegetative reproductive organ with a carrier containing the Present compound or the Composition A (film coating treatment, pellet coating treatment). Examples of the above-described vegetative reproductive organ include particularly seed potato.
When the Composition A is applied to seeds or vegetative reproductive organs, the Composition A may be also applied to seeds or vegetative reproductive organs as a single formulation, or the Composition A may be applied to seeds or vegetative reproductive organs as multiple different formulations by multiple times. Examples of the method in which the Composition A is applied as multiple different formulations by multiple times include, for example, a method in which the formulations comprising as an active component the Present compound only are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredient: and a method in which the formulations comprising as an active component the present compound and the Present ingredients are applied, and seeds or vegetative reproductive organs are air dried, followed by applying the formulations comprising the Present ingredients other than the already-applied Present ingredients, are included.
As used herein, seeds or vegetative reproductive organs carrying the present compound or the Composition A means seeds or vegetative reproductive organs in the state where the present compound or the Composition A is adhered to a surface of the seeds or the vegetative reproductive organ.
The above-described seeds or vegetative reproductive organs carrying the present compound or the Composition A may be adhered by any other materials that are different from the present compound or the Composition A before or after being adhered the present compound or the Composition A to the seeds or vegetative reproductive organs.
Also, when the Composition A is adhered in a form of layer(s) to a surface of seeds or vegetative reproductive organ, the layer(s) is/are composed of one layer or a multiple layers. Also, when multiple layers are formed, each of the layer may be composed of a layer comprising one or more active ingredients, or a combination of a layer comprising one or more active ingredients and a layer not comprising an active ingredient.
Seeds or vegetative reproductive organs carrying the present compound or the Composition A can be obtained, for example, by applying the formulations comprising the present compound or the Composition A by the above-described application method to seeds to seeds or vegetative reproductive organs.
When the Present compound or the Composition A is applied for controlling pests in agricultural fields, the application dose thereof is usually within a range of 1 to 10,000 g of the Present compound per 10,000 m2. In the case of being applied to seeds or vegetative reproductive organs, the dose of application dose thereof is usually within a range of 0.001 to 100 g of the Present compound per 1 Kg of seeds. When the Present compound or the Composition A is formulated into an emulsifiable concentrate, a wettable powder or a flowable etc., they are usually applied by diluting them with water so as to make an effective concentration of the active ingredients 0.01 to 10,000 ppm, and the dust formulation or the granular formulation, etc., is usually applied as itself without diluting them.
Also, the resin preparation which is processed into a sheet or a string may be applied by winding a plant with a sheet or a string of the resin preparation, putting a string of the resin preparation around a crop so that the plant is surrounded by the string, or laying a sheet of the resin preparation on the soil surface near the root of a plant.
When the Present compound or the Composition A is used to control harmful arthropods that live inside a house, the application dose as an amount of the Present compound is usually within a range from 0.01 to 1,000 mg per 1 m2 of an area to be treated, in the case of using it on a planar area.
In the case of using it spatially, the application dose as an amount of the Present compound is usually within a range from 0.01 to 500 mg per 1 m3 of the space to be treated.
When the Present compound or the Composition A is formulated into emulsifiable concentrates, wettable powders, flowables or the others, such formulations are usually applied after diluting it with water in such a way that a concentration of the active ingredient is within a range from 0.1 to 10,000 ppm. In the case of being formulated into oil solutions, aerosols, smoking agents, poison baits and the others, such formulations are used as itself without diluting it.
When the Present compound or the composition A is used for controlling external parasites of livestock such as cows, horses, pigs, sheep, goats and chickens and small animals such as dogs, cats, rats and mice, the composition of the present invention may be applied to the animals by a known method in the veterinary field. Specifically, when systemic control is intended, the composition of the present invention is administered to the animals as a tablet, a mixture with feed or a suppository, or by injection (including intramuscular, subcutaneous, intravenous and intraperitoneal injections). On the other hand, when non-systemic control is intended, the composition of the present invention is applied to the animals by means of spraying of the oil solution or aqueous solution, pour-on or spot-on treatment, or washing of the animal with a shampoo formulation, or by putting a collar or ear tag made of the resin formulations to the animal. In the case of being administered to an animal body, the dose of the compound of the Present compound is usually within a range from 0.1 to 1,000 mg per 1 kg of an animal body weight.
Also, the composition of the Present compound or the Composition A may be used as an agent for controlling pests in agricultural lands such as paddy fields, fields, turfs, and orchards. Examples of the plants include the followings.
corn (dent corn, flint corn, flour corn, popcorn, waxy corn, sweet corn, and field corn), rice (long grain rice, short grain rice, medium grain rice, japonica rice, tropical japonica rice, indica rice, javanica rice, paddy rice, upland rice, floating rice, direct-seeded rice, transplanted rice, and glutinous rice), wheat (bread wheat (hard wheat, soft wheat, medium wheat, red wheat, and white wheat), durum wheat, spelt wheat, and club wheat, winter wheat and spring wheat of them), barley (two-rowed barley (=barley for brewery), six-rowed barley, hull-less barley, and pearl barley, winter barley and spring barley of them), rye (winter rye and spring rye), triticale (winter triticale and spring triticale), oat (winter oat and spring oat), sorghum, cotton (upland cotton and Pima cotton), soybean (ripe seed harvest soybean, green soybeans, and early harvest soybeans, indeterminate type, determinate type, and semi-determinate type of them), peanut, buckwheat, beet (beets for sugar production, beets for feed, beets for root vegetable, beets for leaf vegetable, and beets for fuel), rapeseed (winter rapeseed and spring rapeseed), canola (winter canola and spring canola), sunflower (sunflowers for oil extraction, edible sunflowers, and sunflowers for ornamental purpose), sugar cane, tobacco, tea, mulberry, solanaceous vegetables (for example, eggplant, tomato, pimento, pepper, and potato), cucurbitaceous vegetables (for example, cucumber, pumpkin, zucchini, water melon, and melon), cruciferous vegetables (for example, Japanese radish, white turnip, horseradish, kohlrabi, Chinese cabbage, cabbage, leaf mustard, broccoli, and cauliflower), asteraceous vegetables (for example, burdock, crown daisy, artichoke, and lettuce), liliaceous vegetables (for example, welsh onion, onion, garlic, and asparagus), ammiaceous vegetables (for example, carrot, parsley, celery, and parsnip), chenopodiaceous vegetables (for example, spinach and Swiss chard), lamiaceous vegetables (for example, perilla, mint, and basil), strawberry, sweet potato, glutinous yam, eddoe, pomaceous fruits (for example, apple, pear, Japanese pear, Chinese white pear, Chinese quince, and quince), stone fleshy fruits (for example, peach, plum, nectarine, Japanese apricot (Prunus mume), cherry fruit, apricot, and prune), citrus fruits (for example, Citrus unshiu, orange, lemon, lime, and grapefruit), nuts (for example, chestnuts, walnuts, hazelnuts, almond, pistachio, cashew nuts, and macadamia nuts), berry fruits (for example, blueberry, cranberry, blackberry, and raspberry), grapes, Japanese persimmon, fig, olive, Japanese plum, banana, coffee, date palm, coconuts, ornamental plants, forest plants, turfs, grasses, and the others.
The above plants are not specifically limited as long as they are generally cultivated cultivars. The above plants also include plants which may be produced by natural breeding, plants which may be generated by mutation, F1 hybrid plants, and genetically modified crops. Examples of the genetically modified crops include plants which have resistance to HPPD (4-hydroxyphenylpyruvate dioxygenase enzyme) inhibitors such as isoxaflutole, ALS (acetolactate synthase) inhibitors such as imazethapyr and thifensulfuron-methyl, EPSP (5-enolpyruvylshikimate-3-phosphate synthase) inhibitors, glutamine synthetase inhibitors, PPO (protoporphyrinogen oxidase) inhibitors, or herbicide such as bromoxynil and dicamba; plants which can synthesize a selective toxin known in Bacillus spp. such as Bacillus thuringiensis or the like; and plants which can synthesize a gene fragment or the like which is partially identical to an endogenous gene derived from a harmful insect, and induce a gene silencing (RNAi; RNA interference) in the target harmful insect to achieve a specific insecticidal activity.
Hereinafter, the present invention is explained in more detail by Preparation Examples, Reference Preparation Examples, Formulation Examples, and Test Examples, however, the present invention should not be limited to the these Examples.
As used herein, Me represents methyl group, Et represents ethyl group, Pr represents propyl group, i-Pr represents isopropyl group, Bu represents butyl group, i-Bu represents isobutyl group, t-Bu represents tert-butyl group, Pen represents pentyl group, c-Pr represents cyclopropyl group, c-Bu represents cyclobutyl group, c-Pen represents cyclopentyl group, c-Hex represents cyclohexyl group, and Ph represents phenyl group.
Firstly, Preparation examples of the compound of the present invention are described.
When a physical property of a compound is measured by a liquid chromatography/mass spectrometry analysis (hereinafter, referred to as LCMS), a measured molecular ion value [M+H]+ or [M−H]− and a retention time (hereinafter, referred to as RT) is described. The measured condition for liquid chromatography (hereinafter, referred to as LC) and mass spectrometry (hereinafter, referred to as MS) is described below.
[LC condition]
[MS condition]
Under nitrogen atmosphere, a mixture of 1,5-dibromo-2.4-dimethylbenzene 1.06 g, methyl acetoacetate 1.03 g, palladium (II) acetate 0.09 g, 2-di-tert-buthylphosphino-2′,4′,6′-triisopropylbiphenyl 0.17 g, tripotassium phosphate 2.55 g, and toluene 20 mL was stirred under reflux for 2 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 1-1 represented by the following formula 0.71 g.
Intermediate compound 1-1: 1H-NMR (CDCl3) δ: 12.95 (1H, s), 7.23 (1H, s), 7.10 (1H, s), 3.68 (3H, s), 2.37 (3H, s), 2.07 (3H, s), 1.77 (3H, s).
To a mixture of the intermediate compound 1-1 0.30 g, THE 2 mL, and methanol 2 mL was added 28% solution of sodium methoxide in methanol 0.3 mL, and the mixture was stirred at 60° C. for 3 hours. To the resulting mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure, to obtain the intermediate compound 1-2 represented by the following formula 0.22 g.
Intermediate compound 1-2: 1H-NMR (CDCl3) δ: 7.35 (1H, s), 7.05 (1H, s), 3.69 (3H, s), 3.57 (2H, s), 2.33 (3H, s), 2.22 (3H, s).
A mixture of the intermediate compound 1-2 3.72 g, N,N-dimethylformamide dimethylacetal 3.45 g, and DMF 15 mL was stirred under reflux for one and a half days. Water was added to the resulting mixture, and the mixture was extracted with MTBE. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound 1-3 represented by the following formula 3.10 g.
Intermediate compound 1-3: 1H-NMR (CDCl3) δ: 7.56 (1H, s), 7.28 (1H, s), 7.03 (1H, s), 3.61 (3H, s), 2.67 (6H, s), 2.35 (3H, s), 2.10 (3H, s).
To a mixture of the intermediate compound 1-3 0.27 g, and methanol 10 mL was added 2N hydrochloric acid 5 mL under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound 1-4 represented by the following formula 0.23 g.
To a mixture of the intermediate compound 1-4 0.23 g, cesium carbonate 0.34 g, and NMP 4 mL was added dimethyl sulfate 0.15 g, and the mixture was stirred at room temperature for 3 hours. To the resulting mixture was added saturated brine, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 1-5 represented by the following formula 0.19 g.
Intermediate compound 1-5: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.27 (1H, s), 7.10 (1H, s), 3.84 (3H, s), 3.70 (3H, s), 2.35 (3H, s), 2.09 (3H, s).
Under nitrogen atmosphere, mixture of the intermediate compound 1-5 1.0 g, bis(pinacolato)diboron 1.1 g, PdCl2(dppf) 0.24 g, tripotassium phosphate 0.66 g, and dimethoxyethane 30 mL were stirred at 80° C. for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 2-1 represented by the following formula 1.0 g.
Intermediate compound 2-1: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 7.50 (1H, s), 7.04 (1H, s), 3.80 (3H, s), 3.68 (3H, s), 2.50 (3H, s), 2.14 (3H, s), 1.31 (12H, s).
Under nitrogen atmosphere, mixtures of the intermediate compound 1-5 2.0 g, bis(triphenylphosphine)palladium (II) dichloride 0.47 g, tributyl (1-ethoxyvinyl)stannate 4.4 mL and 1,4-dioxane 20 mL were stirred at 110° C. for 4 hours. To the resulting mixture was added 1N hydrochloric acid, and the mixture was stirred at room temperature for 1 hour.
Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 3-1 represented by the following formula 1.4 g.
Intermediate compound 3-1: 1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.50 (1H, s), 7.11 (1H, s), 3.85 (3H, s), 3.72 (3H, s), 2.55 (3H, s), 2.52 (3H, s), 2.18 (3H, s).
A mixture of the intermediate compound 2-1 0.54 g, m-chloroperoxybenzoic acid 0.50 g, acetonitrile 5 mL, ethanol 5 mL, and water 5 mL was stirred at room temperature for 2.5 hours. To the resulting mixture were added aqueous sodium thiosulfate solution and aqueous sodium bicarbonate solution, and the mixtures were stirred at room temperature for 2 hours. The resulting mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 4-1 represented by the following formula 0.37 g.
Intermediate compound 4-1: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.98 (1H, s), 6.55 (1H, s), 4.51 (1H, s), 3.83 (3H, s), 3.70 (3H, s), 2.21 (3H, s), 2.07 (3H, s).
Under nitrogen atmosphere, a mixture of 3-bromo-4,5-dimethylphenol 2.0 g, bis(pinacolato)diboron 3.8 g, PdCl2(dppf) 0.36 g, potassium acetate 2.0 g, and DMSO 25 mL were stirred at 80° C. for 7 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 5-1 represented by the following formula 2.6 g.
Intermediate compound 5-1: 1H-NMR (CDCl3) δ: 7.05 (1H, d), 6.75 (1H, d), 4.62 (1H, br s), 2.38 (3H, s), 2.22 (3H, s), 1.34 (12H, s).
The compounds which were prepared according to the Reference Preparation Example 5 and their physical property value are shown below.
A compound represented by formula (C5-a):
wherein R1, R2a, R2b, and Rx represents any combination described in [Table A}].
Intermediate compound 5-2: 1H-NMR (CDCl3) δ: 7.38 (1H, d), 6.87 (1H, d), 4.83 (1H, d), 2.45 (3H, s), 1.33 (12H, s).
Intermediate compound 5-3: 1H-NMR (CDCl3) δ: 7.31 (1H, s), 6.66 (1H, s), 5.29 (1H, s), 3.88 (3H, s), 2.48 (3H, s), 1.32 (12H, s).
Under nitrogen atmosphere, a mixture of the intermediate compound 5-1 2.5 g, methyl (Z)-2-iodo-3-methoxy acrylate 2.9 g, 2-(dicyclohexylphoshino)-2′,6′-dimethoxybiphenyl 0.21 g, Pd2(dba)3 0.23 g, tripotassium phosphate 4.22 g, toluene 25 mL and water 5 mL were stirred at 110° C. for 4 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 6-1 represented by the following formula 1.6 g.
Intermediate compound 6-1: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.64 (1H, d), 6.46 (1H, d), 4.82-4.78 (1H, br m), 3.82 (3H, s), 3.70 (3H, s), 2.24 (3H, s), 1.99 (3H, s).
The compounds which were prepared according to the Reference Preparation Example 6 and their physical property value are shown below.
A compound represented by formula (C6-a):
wherein R1, R2a, R2b, Ea, X and L represent any combination described in [Table A2].
Intermediate compound 6-2: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.93 (1H, d), 6.76 (1H, d), 4.96 (1H, d), 3.84 (3H, s), 3.71 (3H, s), 2.08 (3H, s).
Intermediate compound 6-3: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.72 (1H, s), 6.70 (1H, s), 5.40 (1H, s), 3.87 (3H, s), 3.83 (3H, s), 3.70 (3H, s), 2.11 (3H, s).
Under nitrogen atmosphere, to a mixture of the intermediate compound 6-1 0.6 g and chloroform 6 mL were added triethylamine 0.46 mL and trifluoroacetic anhydride 0.50 mL successively at 0° C. and the mixture was stirred for 30 minutes. To the resulting mixture was added aqueous sodium bicarbonate solution, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain the intermediate compound 7-1 represented by the following formula 0.70 g.
Intermediate compound 7-1: 1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.02 (1H, d), 6.89 (1H, d), 3.85 (3H, s), 3.71 (3H, s), 2.32 (3H, s), 2.07 (3H, s).
The compounds which were prepared according to the Reference Preparation Example 7 and their physical property value are shown below.
A compound represented by formula (C7-a):
wherein R1, R2a, R2b, X and L represent any combination described in [Table A3].
Intermediate compound 7-2: 1H-NMR (CDCl3) δ: 7.59 (1H, s), 7.12-7.05 (2H, m), 3.86 (3H, s), 3.71 (3H, s), 2.18 (3H, s). intermediate compound 7-3: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 6.97 (1H, s), 6.87 (1H, s), 3.90 (3H, s), 3.85 (3H, s), 3.71 (3H, s), 2.19 (3H, s).
Under nitrogen atmosphere, to a mixture of 1,5-dibromo-2.4-dimethylbenzene 5 g and THF 30 mL was added butyl lithium (1.6 M hexane solution) 12 mL dropwise at −78° C., and the mixture was stirred at −78° C. for 1 hour. To the resulting mixture was added dimethyl oxalate 2.5 g and the mixture was stirred at 0° C., for 3 hours. To the resulting mixture was added saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The resulting mixture was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 8-1 represented by the following formula 3.9 g.
Intermediate compound 8-1: 1H-NMR (CDCl3) δ: 7.83 (1H, s), 7.18 (1H, s), 3.97 (3H, s), 2.51 (3H, s), 2.42 (3H, s).
The compounds which were prepared according to the Reference Preparation Example 8 and their physical property value are shown below.
Intermediate compound 8-2: 1H-NMR (CDCl3) δ: 7.79-7.72 (1H, m), 6.96 (1H, m), 3.97 (3H, s).
A mixture of the intermediate compound 8-1 3.5 g, O—methyl hydroxylamine hydrochloride salt 2.3 g, and ethanol 80 mL was stirred at 55° C. for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography to obtain the intermediate compound 9-1 represented by the following formula 1.3 g.
Intermediate compound 9-1: 1H-NMR (CDCl3) δ: 7.26 (1H, s), 7.13 (1H, s), 4.06 (3H, s), 3.88 (3H, s), 2.37 (3H, s), 2.10 (3H, s).
The compounds which were prepared according to the Reference Preparation Example 9 and their physical property value are shown below.
Intermediate compound 9-2: 1H-NMR (CDCl3) δ: 7.64-7.57 (1H, m), 6.92-6.86 (1H, m), 4.14 (3H, s), 3.91 (3H, s).
To a mixture of the intermediate compound 3-1 0.20 g, o-methyl hydroxylamine hydrochloride salt 0.13 g, and ethanol 5 mL was added pyridine 0.10 mL at room temperature, and the mixture was stirred at room temperature overnight. The resulting mixture was diluted with ethyl acetate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=3:7) to obtain the present compound 1-1 represented by the following formula 0.22 g.
Present compound 1-1: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.06 (1H, s), 6.98 (1H, s), 3.95 (3H, s), 3.81 (3H, s), 3.68 (3H, s), 2.33 (3H, s), 2.15 (3H, s), 2.14 (3H, s).
The compounds which were prepared according to the Preparation Example 1 and their physical property value are shown below.
A compound represented by formula (1-1):
wherein R1, R2a, R2b, R3, R4, X and L represent any combination described in [Table A4].
Present compound 1-2: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.06 (1H, s), 6.98 (1H, s), 4.19 (2H, q), 3.80 (3H, s), 3.68 (3H, s), 2.34 (3H, s), 2.16 (3H, s), 2.14 (3H, s), 1.31 (3H, t).
Present compound 1-3: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.06 (1H, s), 6.99 (1H, s), 3.96 (2H, d), 3.81 (3H, s), 3.68 (3H, s), 2.35 (3H, s), 2.19 (3H, s), 2.14 (3H, s), 1.25-1.15 (1H, m), 0.58-0.52 (2H, m), 0.33-0.28 (2H, m).
Present compound 1-4: 1H-NMR (CDCl3) δ: 7.58 (11H, s), 7.33-7.27 (2H, m), 7.25-7.21 (2H, m), 7.13 (1H, s), 7.09 (1H, s), 7.02-6.98 (1H, m), 3.83 (3H, s), 3.71 (3H, s), 2.43 (3H, s), 2.39 (3H, s), 2.18 (3H, s).
Present compound 1-5: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.43-7.32 (5H, m), 7.04 (1H, s), 6.97 (1H, s), 5.19 (2H, s), 3.80 (3H, s), 3.68 (3H, s), 2.25 (3H, s), 2.20 (3H, s), 2.13 (3H, s).
Present compound 1-6: 1H-NMR (CDCl3) δ: 7.56 (1H, s), 7.07 (1H, s), 6.98 (1H, s), 4.74 (1H, t), 4.62 (1H, t), 4.41 (1H, t), 4.34 (1H, t), 3.82 (3H, s), 3.69 (3H, s), 2.34 (3H, s), 2.20 (3H, s), 2.14 (3H, s).
Present compound 1-7: 1H-NMR (CDCl3) δ: 8.29 (1H, s), 7.56 (1H, s), 7.44 (1H, s), 7.05 (1H, s), 4.21 (2H, q), 3.82 (3H, s), 3.69 (3H, s), 2.38 (3H, s), 2.15 (3H, s), 1.32 (3H, t).
Present compound 1-8: 1H-NMR (CDCl3) δ: 8.35 (1H, s), 7.56 (1H, s), 7.43-7.40 (2H, m), 7.38-7.30 (4H, m), 7.05 (1H, s), 5.19 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
Present compound 1-9: 1H-NMR (CDCl3) δ: 8.33 (1H, s), 7.56 (1H, s), 7.40 (1H, s), 7.37-7.30 (4H, m), 7.05 (1H, s), 5.14 (2H, s), 3.82 (3H, s), 3.69 (3H, s), 2.36 (3H, s), 2.15 (3H, s).
Under nitrogen atmosphere, a mixture of the intermediate compound 1-5 0.10 g, PdCl2(PPh3)4 0.02 g, cyclopropyl acetylene 0.15 mL, tetrabutylammonium fluoride (1 mol/L THE solution) 1.0 mL, and THE 3 mL was stirred at 80° C. for 6 hours. Aqueous sodium bicarbonate solution was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=1:3) to obtain the present compound 2-1 represented by the following formula 0.09 g.
Present compound 2-1: 1H-NMR (CDCl3) δ: 7.53 (1H, s), 7.10 (1H, s), 7.02 (1H, s), 3.81 (3H, s), 3.68 (3H, s), 2.34 (3H, s), 2.11 (3H, s), 1.49-1.42 (1H, m), 0.88-0.82 (2H, m), 0.79-0.74 (2H, m).
The compounds which were prepared according to the Preparation Example 2 and their physical property value are shown below.
A compound represented by formula (2-1):
wherein R1, R2a, R2b, R5, X and L represent any combination described in [Table B1].
Present compound 2-2: 1H-NMR (CDCl3) δ: 7.09 (1H, s), 7.06 (1H, s), 4.04 (3H, s), 3.86 (3H, s), 2.37 (3H, s), 2.12 (3H, s), 1.31 (9H, s).
Present compound 2-3: LCMS: 301 [M+H]+, RT=2.33 min.
Present compound 2-4: 1H-NMR (CDCl3) δ: 7.62-7.51 (3H, m), 7.38-7.34 (3H, m), 6.98-6.92 (1H, m), 4.14 (3H, s), 3.91 (3H, s).
A Mixture of the intermediate compound 4-1 0.18 g, butanol 0.06 mL, bis(2-methoxyethyl) azodicarboxylate 0.13 g, triphenylphosphine 0.13 g, and chloroform 4 mL was stirred a room temperature for 4 hours. To the resulting mixture was added hydrobicarbonate water, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=1:3) to obtain the present compound 3-1 represented by the following formula 0.13 g.
Present compound 3-1: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.98 (1H, s), 6.56 (1H, s), 3.92 (2H, t), 3.82 (3H, s), 3.70 (3H, s), 2.18 (3H, s), 2.07 (3H, s), 1.79-1.70 (2H, m), 1.54-1.44 (2H, m), 0.96 (3H, t).
The compounds which were prepared according to the Preparation Example 3 and their physical property value are shown below.
A compound represented by formula (3-1):
wherein R1, R2a, R2b, R6, X and L represent any combination described in [Table A5].
Present compound 3-2: 1H-NMR (CDCl3) δ: 7.54 (1H, s), 6.70 (1H, d), 6.52 (1H, d), 3.91 (2H, t), 3.82 (3H, s), 3.70 (3H, s), 2.26 (3H, s), 2.00 (3H, s), 1.77-1.69 (2H, m), 1.52-1.41 (2H, m), 0.96 (3H, t).
Present compound 3-3: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.93 (1H, d), 6.70 (1H, d), 3.99 (2H, t), 3.84 (3H, s), 3.71 (3H, s), 2.08 (3H, s), 1.82-1.73 (2H, m), 1.53-1.43 (2H, m), 0.96 (3H, t).
Present compound 3-4: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 6.73 (1H, s), 6.63 (1H, s), 3.97 (2H, t), 3.85 (3H, s), 3.84 (3H, s), 3.71 (3H, s), 2.12 (3H, s), 1.84-1.74 (2H, m), 1.52-1.41 (2H, m), 0.95 (3H, t).
Under nitrogen atmosphere, a mixture of the intermediate compound 7-2 0.20 g, 3-methoxyphenylboronic acid 0.11 g, PdCl2(dppf) 0.02 g, tripotassium phosphate 0.23 g, dimethoxyethane 4 mL, and water 0.4 mL was stirred at 80° C. for 3 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=1:3) to obtain the present compound 4-1 represented by the following formula 0.16 g.
Present compound 4-1: 1H-NMR (CDCl3) δ: 7.59 (1H, s), 7.33 (1H, t), 7.19 (1H, d), 7.16-7.09 (2H, m), 7.02 (1H, d), 6.91-6.87 (1H, m), 3.84 (3H, s), 3.84 (3H, s), 3.72 (3H, s), 2.20 (3H, s).
The compounds which were prepared according to the Preparation Example 4 and their physical property value are shown below.
A compound represented by formula (4-1):
wherein R1, R2a, R2b, R3a, R4a, R5a, R6a, R7a, X and L represent any combination described in [Table A6].
Present compound 4-2: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.40-7.30 (5H, in), 7.15 (1H, s), 7.01 (1H, s), 3.83 (3H, s), 3.71 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
Present compound 4-3: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.30 (1H, t), 7.14 (1H, s), 7.01 (1H, s), 6.95-6.92 (1H, m), 6.90-6.84 (2H, in), 3.83 (3H, s), 3.82 (3H, s), 3.71 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
Present compound 4-4: 1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.28-7.20 (4H, m), 7.10 (1H, s), 6.97 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.34 (3H, s), 2.31 (3H, s), 2.13 (3H, s).
Present compound 4-5: 1H-NMR (CDCl3) δ: 7.60 (1H, s), 7.35 (1H, d), 7.32 (1H, t), 7.20 (1H, d), 7.19-7.15 (1H, m), 7.11 (1H, t), 6.87-6.83 (1H, m), 3.85 (3H, s), 3.83 (3H, s), 3.71 (3H, s), 2.36 (3H, s), 2.12 (3H, s).
Present compound 4-6: 1H-NMR (CDCl3) δ: 7.83 (1H, s), 7.81-7.77 (1H, m), 7.64-7.59 (2H, m), 7.52 (1H, t), 7.16 (1H, d), 7.06 (1H, d), 3.86 (3H, s), 3.73 (3H, s), 2.22 (3H, s).
Present compound 4-7: 1H-NMR (CDCl3) δ: 7.42-7.31 (5H, m), 7.17 (1H, s), 7.00 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.20 (3H, s).
Present compound 4-8: 1H-NMR (CDCl3) δ: 7.35-7.29 (3H, m), 7.23-7.19 (1H, m), 7.17 (1H, s), 6.96 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.20 (3H, s).
Present compound 4-9: 1H-NMR (CDCl3) δ: 7.34-7.28 (1H, m), 7.17 (1H, s), 7.00 (1H, s), 6.93-6.86 (3H, m), 4.07 (3H, s), 3.87 (3H, s), 3.82 (3H, s), 2.28 (3H, s), 2.20 (3H, s).
Present compound 4-10: 1H-NMR (CDCl3) δ: 7.45-7.39 (1H, m), 7.28-7.25 (1H, m), 7.21-7.17 (3H, m), 6.98 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.27 (3H, s), 2.21 (3H, s).
Present compound 4-11: 1H-NMR (CDCl3) δ: 7.61-7.57 (2H, m), 7.53-7.50 (2H, m), 7.21-7.19 (1H, m), 6.98 (1H, s), 4.07 (3H, s), 3.88 (3H, s), 2.26 (3H, s), 2.21 (3H, s).
Present compound 4-12: 1H-NMR (CDCl3) δ: 7.41-7.28 (5H, m), 7.16 (1H, s), 6.99 (1H, s), 6.78 (1H, s), 3.97 (3H, s), 2.93 (3H, d), 2.26 (3H, s), 2.20 (3H, s).
Present compound 4-13: 1H-NMR (CDCl3) δ: 7.34-7.32 (1H, m), 7.31-7.27 (2H, m), 7.23-7.20 (1H, m), 7.15 (1H, s), 6.95 (1H, s), 6.79 (1H, br s), 3.98 (3H, s), 2.93 (3H, d), 2.25 (3H, s), 2.19 (3H, s).
Present compound 4-14: LCMS: 311 [M+H]+, RT=2.19 min.
Present compound 4-15: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.31-7.25 (1H, m), 7.17-7.10 (4H, m), 7.00 (1H, s), 3.82 (3H, s), 3.71 (3H, s), 2.38 (3H, s), 2.26 (3H, s), 2.19 (3H, s).
Present compound 4-16: LCMS: 311 [M+H]+, RT=2.20 min.
Present compound 4-17: LCMS: 315 [M+H]+, RT=2.09 min.
Present compound 4-18: 1H-NMR (CDCl3) δ: 7.58 (1H, s), 7.37-7.31 (1H, m), 7.16-7.10 (2H, m), 7.08-6.97 (3H, m), 3.84 (3H, s), 3.71 (3H, s), 2.25 (3H, s), 2.20 (3H, s).
Present compound 4-19: LCMS: 315 [M+H)+, RT=2.12 min.
Present compound 4-20: LCMS: 327 [M+H]+, RT=2.07 min.
Present compound 4-21: LCMS: 327 [M+H]+, RT=2.08 min.
Present compound 4-22: LCMS: 331 [M+H]+, RT=2.22 min.
Present compound 4-23: LCMS: 343 [M+H]+, RT=2.18 min.
Present compound 4-24: 1H-NMR (CDCl3) δ: 7.56 (1H, s), 7.37-7.31 (3H, m), 7.13-7.03 (5H, m), 7.00-6.94 (3H, m), 3.82 (3H, s), 3.70 (3H, s), 2.24 (3H, s), 2.18 (3H, s).
Present compound 4-25: 1H-NMR (CDCl3) δ: 7.57 (1H, s), 7.47-7.27 (6H, m), 7.13 (1H, s), 7.00 (1H, s), 6.97-6.92 (3H, m), 5.08 (2H, s), 3.82 (3H, s), 3.71 (3H, s), 2.21 (3H, s), 2.19 (3H, s).
Present compound 4-26: LCMS: 342 [M+H]+, RT=2.11 min.
Present compound 4-27: LCMS: 337 [M+H]+, RT=2.31 min.
Present compound 4-28: LCMS: 345 [M+H]+, RT=2.04 min.
Present compound 4-29: LCMS: 333 [M+H]+, RT=2.16 min.
Present compound 4-30: LCMS: 324 [M+H]+, RT=2.04 min.
Under nitrogen atmosphere, a mixture of the intermediate compound 2-1 0.18 g, 2-bromo-3-fluoropyridine 0.09 mL, PdCl2(dppf) 0.02 g, tripotassium phosphate 0.24 g, dimethoxyethane 4 mL, and water 1 mL was stirred at 80° C. for 8 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=2: 3) to obtain the present compound 5-1 represented by the following formula 0.10 g.
Present compound 5-1: 1H-NMR (CDCl3) δ: 8.51-8.49 (1H, m), 7.57 (1H, s), 7.49-7.43 (1H, m), 7.31-7.25 (1H, m), 7.17 (1H, d), 7.14 (1H, s), 3.81 (3H, s), 3.68 (3H, s), 2.24 (3H, s), 2.20 (3H, s).
The compounds which were prepared according to the Preparation Example 5 and their physical property value are shown below.
A compound represented by formula (5-1):
wherein R1, R2a, R2b, Eb, X and L represent any combination described in [Table B2] (where • represents a binding site to a benzene ring).
Present compound 5-2: 1H-NMR (CDCl3) δ: 7.89 (1H, t), 7.63-7.57 (3H, m), 7.19 (1H, s), 7.17 (1H, s), 3.83 (3H, s), 3.70 (3H, s), 2.40 (3H, s), 2.20 (3H, s).
Present compound 5-3: 1H-NMR (CDCl3) δ: 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
Present compound 5-4: 1H-NMR (CDCl3) δ: 7.18 (1H, s), 7.13 (1H, d), 7.01 (1H, s), 6.90 (1H, d), 4.07 (3H, s), 3.87 (3H, s), 2.22 (3H, s), 2.20 (3H, s).
Present compound 5-5: 1H-NMR (CDCl3) δ: 7.87 (1H, s), 7.84 (1H, s), 7.58 (1H, s), 7.16 (1H, s), 7.07 (1H, s), 3.84 (3H, s), 3.72 (3H, s), 2.35 (3H, s), 2.18 (3H, s).
Under nitrogen atmosphere, a mixture of the intermediate compound 1-5 0.10 g, 1-cyclopentenyl boronic acid 0.08 g, PdCl2(dppf) 0.02 g, tripotassium phosphate 0.21 g, dimethoxyethane 4 mL, and water 1 mL was stirred at 80° C. for 6 hours. Water was added to the resulting mixture, and the mixture was extracted with ethyl acetate. The resulting organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to a silica gel column chromatography (ethyl acetate: hexane=1:3) to obtain the present compound 6-1 represented by the following formula 0.08 g.
Present compound 6-1: 1H-NMR (CDCl3) δ: 7.55 (1H, s), 7.02 (1H, s), 6.82 (1H, s), 5.58-5.54 (1H, m), 3.81 (3H, s), 3.70 (3H, s), 2.24 (3H, s), 2.21-2.16 (2H, m), 2.16-2.11 (5H, m), 1.76-1.69 (2H, m), 1.69-1.62 (2H, m).
The compounds which were prepared according to the Preparation Example 6 and their physical property value are shown below.
Present compound 6-2: LCMS: 287 [M+H]+, RT=2.25 min.
Next, examples of the present compounds and intermediate compounds which are prepared according to either the Preparation Examples described in the Working Examples or the processes described in the Description of the present application are indicated below.
A compound represented by formula (1A):
(hereinafter, referred to as Compound (1A))
Combination A consists of substituent numbers ZA1 to ZA364. Substituent numbers ZA1 to ZA364 represent any combination of R3 and R4 in the compound (1A), which is hereinafter referred to as [Substituent No.; R3, R4]. For example, Substituent No. ZA2 represents a combination wherein R3 represents an ethyl group, and R4 represents a hydrogen atom.
[ZA1;Me,H], [ZA2;Et,H], [ZA3;Pr,H], [ZA4;Bu,H], [ZA5;Pen,H], [ZA 6;Hex,H], [ZA7;i-Pr,H], [ZA8;i-Bu,H], [ZA9;t-Bu,H], [ZA10;c-Pr, H], [ZA11;c-Bu,H], [ZA12;c-Pen,-H], [ZA13;c-Hex,H], [ZA14;CH2c-P r,H], [ZA15;CH2c-Pen,H], [ZA16;CH2c-Hex,H], [ZA17;CH2CH═CH2,H), [ZA18;CH2CH═CHMe,H), [ZA19;CH2CH═CMe2,H], [ZA20;CH2C≡CH,H], [Z A21;CH2C═CMe,H], [ZA22;CH2Ph,H], [ZA23;CH2 (2-F-Ph),H], [ZA24;C H2 (3-F-Ph),H], [ZA25;CH2 (4-F-Ph),H], [ZA26;CH2 (2-C1-Ph),H], [Z A27;CH2 (3-C1-Ph),H], [ZA28;CH2 (4-C1-Ph),H], [ZA29;CH2 (2-Br-P h),H], [ZA30;CH2 (3-Br-Ph),H], [ZA31;CH2 (4-Br-Ph),H], [ZA32;CH2 (2-Me-Ph),H], [ZA33;CH2 (3-Me-Ph),H], [ZA34;CH2 (4-Me-Ph),H], [Z A35;CH2 (2-Et-Ph),H], [ZA36;CH2 (3-Et-Ph),H], [ZA37;CH2 (4-Et-P h), H], [ZA38;CH2 (2-t-Bu-Ph),H], [ZA39;CH2 (3-t-Bu-Ph), H], [ZA4 0;CH2 (4-t-Bu-Ph),H], [ZA41;CH2 (2-CF3-Ph),H], [ZA42;CH2 (3-CF3-Ph),H], [ZA43;CH2 (4-CF3-Ph),H], [ZA44;CH2 (2-OMe-Ph),H], [ZA45; CH2 (3-OMe-Ph),H], [ZA46;CH2 (4-OMe-Ph),H], [ZA47;CH2 (2-SMe-Ph), H], [ZA48;CH2 (3-SMe-Ph),H], [ZA49;CH2 (4-SMe-Ph),H], [ZA50;CH2 (2-CN-Ph), H], [ZA51; CH2 (3-CN-Ph), H], [ZA52; CH2 (4-CN-Ph), H], [Z A53;CH2 (2,4-F2-Ph),H], [ZA54;CH2 (2,5-F2-Ph),H], [ZA55;CH2 (3,4-F2-Ph),H], [ZA56;CH2 (3,5-F2-Ph),H], [ZA57;CH2 (2,4-Cl2-Ph),H], [ZA58;CH2 (2,5-Cl2-Ph),H], [ZA59;CH2 (3,4-C12-Ph),H], [ZA60;CH2 (3,5-Cl2-Ph), H], [ZA61;CH2 (2,4-Me2-Ph),H], [ZA62; CH2 (2,5-Me2-Ph),H], [ZA63;CH2 (3,4-Me2-Ph),H], [ZA64;CH2 (3,5-Me2-Ph),H], [Z A65;CH2 (2-F-4-C1-Ph),H], [ZA66;CH2 (2-C1-4-F-Ph),H], [ZA67;CH2 (2-F-4-Me-Ph),H], [ZA68;CH2 (2-Me-4-F-Ph),H], [ZA69;CH2 (2-F-4-OMe-Ph),H], [ZA70;CH2 (2-OMe-4-F-Ph),H], [ZA71;CCH2 (2-Me-4-C1-P h),H], [ZA72;CH2 (2-C1-4-Me-Ph),H], [ZA73;CH2 (2-Me-4-OMe-Ph), H], [ZA74;CH2 (2-OMe-4-Me-Ph),H], [ZA75;CH2 (2-C1-4-OMe-Ph),H], [ZA76;CH2 (2-OMe-4-C1-Ph),H], [ZA77;CH2 (2,4,6-F3-Ph),H], [ZA7 8;CH2 (3,4,5-F3-Ph),H], [ZA79;CH2 (2-pyridyl),H], [ZA80;CH2 (3-p yridyl),H), [ZA81;CH2 (4-pyridyl),H], [ZA82;CH2 (3-F-pyridin-2-yl),H], [ZA83;CH2 (4-F-pyridin-2-yl),H], [ZA84;CH2 (5-F-pyridin-2-yl),H], [ZA85;CH2 (6-F-pyridin-2-yl),H], [ZA86;CH2 (3-C1-pyr idin-2-yl),H], [ZA87;CH2 (4-C1-pyridin-2-yl),H], [ZA88;CH2 (5-C 1-pyridin-2-yl),H], [ZA89;CH2 (6-C1-pyridin-2-yl),H], [ZA90;CH 2 (3-Me-pyridin-2-yl),H], [ZA91;CH2 (4-Me-pyridin-2-yl),H], [ZA 92;CH2 (5-Me-pyridin-2-yl),H], [ZA93;CH2 (6-Me-pyridin-2-yl), H], [ZA94;CH2 (3-OMe-pyridin-2-yl),H], [ZA95;CH2 (4-OMe-pyridin-2-yl),H], [ZA96;CH2 (5-OMe-pyridin-2-yl),H], [ZA97;CH2 (6-OMe-pyridin-2-yl),H], [ZA98;CH2 (3-CF3-pyridin-2-yl),H], [ZA99;CH2 (4-CF3-pyridin-2-yl),H], [ZA100;CH2 (5-CF3-pyridin-2-yl),H], [ZA101;CH2 (6-CF3-pyridin-2-yl),H], [ZA102;CH2 (3-CN-pyridin-2-yl),H], [ZA103;CH2 (4-CN-pyridin-2-yl),H], [ZA104;CH2 (5-CN-py ridin-2-yl),H], [ZA105;CH2 (6-CN-pyridin-2-yl),H],[ZA106;CH2 (2-F-pyridin-3-yl),H], [ZA107;CH2 (4-F-pyridin-3-yl),H], [ZA10 8;CH2 (5-F-pyridin-3-yl),H], [ZA109;CH2 (6-F-pyridin-3-yl),H], [ZA110;CH2 (2-C1-pyridin-3-yl),H], [ZA111;CH2 (4-C1-pyridin-3-yl),H], [ZA112;CH2 (5-C1-pyridin-3-yl),H], [ZA113;CH2 (6-C1-pyr idin-3-yl),H], [ZA114;CH2 (2-Me-pyridin-3-yl),H], [ZA115;CH2 (4-Me-pyridin-3-yl),H], [ZA116;CH2 (5-Me-pyridin-3-yl),H], [ZA11 7;CH2 (6-Me-pyridin-3-yl),H], [ZA118;CH2 (2-OMe-pyridin-3-yl), H], [ZA119;CH2 (4-OMe-pyridin-3-yl),H],[ZA120;CH2 (5-OMe-pyrid in-3-yl),H], [ZA121;CH2 (6-OMe-pyridin-3-yl),H], [ZA122;CH2 (2-CF3-pyridin-3-yl),H], [ZA123;CH2 (4-CF3-pyridin-3-yl),H], [ZA1 24;CH2 (5-CF3-pyridin-3-yl),H], [ZA125;CH2 (6-CF3-pyridin-3-y 1),H], [ZA126;CH2 (2-CN-pyridin-3-yl),H], [ZA127;CH2 (4-CN-pyri din-3-yl),H], [ZA128;CH2 (5-CN-pyridin-3-yl),H], [ZA129;CH2 (6-CN-pyridin-3-yl),H], [ZA130;CH2 (2-F-pyridin-4-yl),H], [ZA131; CH2 (3-F-pyridin-4-yl),H], [ZA132;CH2 (2-C1-pyridin-4-yl),H], [ZA133;CH2 (3-C1-pyridin-4-yl),H], [ZA134;CH2 (2-Me-pyridin-4-yl),H], [ZA135;CH2 (3-Me-pyridin-4-yl),H], [ZA136;CH2 (2-OMe-py ridin-4-yl),H], [ZA137;CH2 (3-OMe-pyridin-4-yl),H], [ZA138;CH2 (2-CF3-pyridin-4-yl),H], [ZA139;CH2 (3-CF3-pyridin-4-yl),H], [ZA140;CH2 (2-CN-pyridin-4-yl),H], [ZA141;CH2 (3-CN-pyridin-4-yl),H], [ZA142;CH2 (2-Thienyl),H], [ZA143;CH2 (3-Thienyl),H], [Z A144;CH2 (2-pyrimidinyl),H], [ZA145;CH2 (4-pyrimidinyl),H], [ZA 146;CH2 (5-pyrimidinyl),H], [ZA147;CH2 (3-pyridazinyl),H], [ZA1 48;CH2 (4-pyridazinyl),H],[ZA149;CH2 (4-Me-thiazol-2-yl),H], [ZA150;CH2 (4-C1-thiazol-2-yl),H], [ZA151;CH2 (5-Me-thiazol-2-yl),H], [ZA152;CH2 (5-C1-thiazol-2-yl),H], [ZA153;(CH22Ph,H], [ZA154;(CH23Ph,H], [ZA155;CH2OMe,H], [ZA156;CH2OEt,H], [ZA15 7;CH2OPr,H], [ZA158;CH2OPh,H], [ZA159;CH2CN,H], [ZA160;Ph,H], [ZA161;2-F-Ph,H], [ZA162;3-F-Ph,H], [ZA163;4-F-Ph,H], [ZA164;2-C1-Ph,H], [ZA165;3-C1-Ph,H],[ZA166;4-C1-Ph,H], [ZA167;2-Me-P h,H],[ZA168;3-Me-Ph,H], [ZA169;4-Me-Ph,H], [ZA170;2-OMe-Ph,H], [ZA171;3-OMe-Ph,H], [ZA172;4-OMe-Ph,H], [ZA173;2-Pyridyl,H], [ZA174;3-Pyridyl,H], [ZA175;4-Pyridyl,H], [ZA176;2-Thienyl,H], [ZA177;3-Thienyl,H], [ZA178;2-pyrimidinyl,H], [ZA179;4-pyrimi dinyl,H], [ZA180;5-pyrimidinyl,H], [ZA181;3-pyridazinyl,H], [Z A182;4-pyridazinyl,H],[ZA183;Me,Me],[ZA184;Et,Me], [ZA185;P r,Me], [ZA186;Bu,Me], [ZA187;Pen,Me], [ZA188;Hex,Me], [ZA189;i-Pr,Me],[ZA190;i-Bu,Me], [ZA191;t-Bu,Me],[ZA192;c-Pr,Me], [ZA1 93;c-Bu,Me], [ZA194;c-Pen,Me], [ZA195;c-Hex,Me],[ZA196;CH2c-P r,Me], [ZA197;CH2c-Pen,Me], [ZA198;CH2c-Hex,Me], [ZA199;CH2CH═CH2,Me], [ZA200;CH2CH═CHMe,Me],
[ZA201;CH2CH═CMe2,Me], [ZA202;CH2C═CH, Me], [ZA203;CH2C═CMe,M e], [ZA204;CH2Ph,Me], [ZA205;CH2 (2-F-Ph),Me], [ZA206;CH2 (3-F-P h),Me], [ZA207;CH2 (4-F-Ph),Me], [ZA208;CH2 (2-C1-Ph),Me], [ZA20 9;CH2 (3-C1-Ph),Me], [ZA210;CH2 (4-C1-Ph),Me], [ZA211;CH2 (2-Br-Ph),Me], [ZA212;CH2 (3-Br-Ph),Me], [ZA213;CH2 (4-Br-Ph),Me], [ZA 214;CH2 (2-Me-Ph),Me], [ZA215;CH2 (3-Me-Ph),Me], [ZA216;CH2 (4-M e-Ph),Me], [ZA217;CH2 (2-Et-Ph),Me], [ZA218;CH2 (3-Et-Ph),Me], [ZA219;CH2 (4-Et-Ph),Me], [ZA220;CH2 (2-t-Bu-Ph),Me], [ZA221;CH 2 (3-t-Bu-Ph),Me], [ZA222;CH2 (4-t-Bu-Ph),Me], [ZA223;CH2 (2-CF3-Ph),Me], [ZA224;CH2 (3-CF3-Ph),Me], [ZA225;CH2 (4-CF3-Ph),Me], [ZA226;CH2 (2-OMe-Ph),Me], [ZA227;CH2 (3-OMe-Ph),Me], [ZA228;CH 2 (4-OMe-Ph),Me], [ZA229;CH2 (2-SMe-Ph),Me], [ZA230;CH2 (3-SMe-P h),Me], [ZA231;CH2 (4-SMe-Ph),Me], [ZA232;CH2 (2-CN-Ph),Me], [ZA 233;CH2 (3-CN-Ph),Me], [ZA234;CH2 (4-CN-Ph),Me], [ZA235;CH2 (2,4-F2-Ph),Me], [ZA236;CH2 (2,5-F2-Ph),Me], [ZA237;CH2 (3,4-F2-Ph), Me], [ZA238;CH2 (3,5-F2-Ph),Me], [ZA239;CH2 (2,4-C12-Ph),Me], [Z A240;CH2 (2,5-Cl2-Ph),Me], [ZA241;CH2 (3,4-Cl2-Ph),Me], [ZA242; CH2 (3,5-Cl2-Ph),Me], [ZA243;CH2 (2,4-Me2-Ph),Me], [ZA244;CH2 (2,5-Me2-Ph),Me], [ZA245;CH2 (3,4-Me2-Ph),Me], [ZA246;CH2 (3,5-Me2-Ph),Me], [ZA247;CH2 (2-F-4-C1-Ph),Me], [ZA248;CH2 (2-C1-4-F-P h),Me], [ZA249;CH2 (2-F-4-Me-Ph),Me], [ZA250;CH2 (2-Me-4-F-Ph), Me], [ZA251;CH2 (2-F-4-OMe-Ph),Me], [ZA252;CH2 (2-OMe-4-F-Ph),M e], [ZA253;CH2 (2-Me-4-C1-Ph),Me], [ZA254;CH2 (2-C1-4-Me-Ph),M e], [ZA255;CH2 (2-Me-4-OMe-Ph),Me], [ZA256;CH2 (2-OMe-4-Me-Ph), Me], [ZA257;CH2 (2-C1-4-OMe-Ph),Me], [ZA258;CH2 (2-OMe-4-C1-Ph), Me], [ZA259;CH2 (2,4,6-F3-Ph),Me], [ZA260;CH2 (3,4,5-F3-Ph),Me], [ZA261;CH2 (2-pyridyl),Me], [ZA262;CH2 (3-pyridyl),Me], [ZA263; CH2 (4-pyridyl),Me], [ZA264;CH2 (3-F-pyridin-2-yl),Me], [ZA265; CH2 (4-F-pyridin-2-yl),Me], [ZA266;CH2 (5-F-pyridin-2-yl),Me], [ZA267;CH2 (6-F-pyridin-2-yl),Me], [ZA268;CH2 (3-C1-pyridin-2-yl),Me], [ZA269;CH2 (4-C1-pyridin-2-yl),Me], [ZA270;CH2 (5-C1-p yridin-2-yl),Me], [ZA271;CH2 (6-C1-pyridin-2-yl),Me], [ZA272;C H2 (3-Me-pyridin-2-yl),Me],[ZA273;CH2 (4-Me-pyridin-2-yl),Me], [ZA274;CH2 (5-Me-pyridin-2-yl),Me], [ZA275;CH2 (6-Me-pyridin-2-yl),Me], [ZA276;CH2 (3-OMe-pyridin-2-yl),Me], [ZA277;CH2 (4-OM e-pyridin-2-yl),Me], [ZA278;CH2 (5-OMe-pyridin-2-yl),Me], [ZA2 79;CH2 (6-OMe-pyridin-2-yl),Me], [ZA280;CH2 (3-CF3-pyridin-2-y 1),Me], [ZA281;CH2 (4-CF3-pyridin-2-yl),Me], [ZA282;CH2 (5-CF3-pyridin-2-yl),Me], [ZA283;CH2 (6-CF3-pyridin-2-yl),Me], [ZA28 4;CH2 (3-CN-pyridin-2-yl),Me], [ZA285;CH2 (4-CN-pyridin-2-yl), Me], [ZA286;CH2 (5-CN-pyridin-2-yl),Me], [ZA287;CH2 (6-CN-pyrid in-2-yl),Me], [ZA288;CH2 (2-F-pyridin-3-yl),Me], [ZA289;CH2 (4-F-pyridin-3-yl),Me], [ZA290;CH2 (5-F-pyridin-3-yl),Me],[ZA29 1;CH2 (6-F-pyridin-3-yl),Me], [ZA292;CH2 (2-C1-pyridin-3-yl),M e], [ZA293;CH2 (4-C1-pyridin-3-yl),Me], [ZA294;CH2 (5-C1-pyridi n-3-yl),Me], [ZA295;CH2 (6-C1-pyridin-3-yl),Me], [ZA296;CH2 (2-Me-pyridin-3-yl),Me], [ZA297;CH2 (4-Me-pyridin-3-yl),Me], [ZA2 98;CH2 (5-Me-pyridin-3-yl),Me], [ZA299;CH2 (6-Me-pyridin-3-yl), Me], [ZA300;CH2 (2-OMe-pyridin-3-yl),Me],
[ZA301;CH2 (4-OMe-pyridin-3-yl),Me], [ZA302;CH2 (5-OMe-pyridin-3-yl),Me], [ZA303;CH2 (6-OMe-pyridin-3-yl),Me], [ZA304;CH2 (2-CF3-pyridin-3-yl),Me], [ZA305;CH2 (4-CF3-pyridin-3-yl),Me], [Z A306;CH2 (5-CF3-pyridin-3-yl),Me], [ZA307;CH2 (6-CF3-pyridin-3 -yl),Me], [ZA308;CH2 (2-CN-pyridin-3-yl),Me], [ZA309;CH2 (4-CN-pyridin-3-yl),Me], [ZA310;CH2 (5-CN-pyridin-3-yl),Me], [ZA311; CH2 (6-CN-pyridin-3-yl),Me], [ZA312;CH2 (2-F-pyridin-4-yl),Me], [ZA313;CH2 (3-F-pyridin-4-yl),Me], [ZA314;CH2 (2-C1-pyridin-4-yl),Me], [ZA315;CH2 (3-C1-pyridin-4-yl),Me], [ZA316;CH2 (2-Me-p yridin-4-yl),Me], [ZA317;CH2 (3-Me-pyridin-4-yl),Me], [ZA318;C H2 (2-OMe-pyridin-4-yl),Me], [ZA319;CH2 (3-OMe-pyridin-4-yl),M e], [ZA320;CH2 (2-CF3-pyridin-4-yl),Me], [ZA321;CH2 (3-CF3-pyri din-4-yl),Me], [ZA322;CH2 (2-CN-pyridin-4-yl),Me], [ZA323;CH2 (3-CN-pyridin-4-yl),Me], [ZA324;CH2 (2-Thienyl),Me], [ZA325;CH2 (3-Thienyl),Me], [ZA326;CH2 (2-pyrimidinyl),Me], [ZA327;CH2 (4-pyrimidinyl),Me], [ZA328;CH2 (5-pyrimidinyl),Me], [ZA329;CH2 (3-pyridazinyl),Me], [ZA330;CH2 (4-pyridazinyl),Me], [ZA331;CH 2 (4-Me-thiazol-2-yl),Me], [ZA332;CH2 (4-C1-thiazol-2-yl),Me], [ZA333;CH2 (5-Me-thiazol-2-yl),Me], [ZA334;CH2 (5-C1-thiazol-2-yl),Me], [ZA335; (CH22Ph,Me], [ZA336; (CH23Ph,Me], [ZA337;CH2OM e,Me], [ZA338;CH2OEt,Me], [ZA339;CH2OPr,Me], [ZA340;CH2OPh,Me], [ZA341;CH2CN,Me],[ZA342;Ph,Me],[ZA343;2-F-Ph,Me], [ZA344;3-F -Ph,Me], [ZA345;4-F-Ph,Me], [ZA346;2-C1-Ph,Me], [ZA347;3-C1-P h,Me],[ZA348;4-C1-Ph,Me], [ZA349;2-Me-Ph,Me], [ZA350;3-Me-Ph, Me], [ZA351;4-Me-Ph,Me], [ZA352;2-OMe-Ph,Me], [ZA353;3-OMe-Ph, Me], [ZA354;4-OMe-Ph,Me], [ZA355;2-Pyridyl,Me], [ZA356;3-Pyrid yl,Me], [ZA357;4-Pyridyl,Me], [ZA358;2-Thienyl,Me], [ZA359;3-T hienyl,Me], [ZA360;2-pyrimidinyl,Me], [ZA361;4-pyrimidinyl,M e], [ZA362;5-pyrimidinyl,Me], [ZA363;3-pyridazinyl,Me], [ZA36 4;4-pyridazinyl,Me]
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX2).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX3).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX4).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methoxy group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX5).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX6).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX7).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX8).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX9).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX10).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX11).
The Compound (1A) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX12).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX13).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX14).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX15).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX16).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX17).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a cyclopropyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX18).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX19).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX20).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX21).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX22).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX23).
The Compound (1A) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX24).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX25).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents an ethyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX26).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX27).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX28).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methoxy group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX29).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a cyclopropyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX30).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX31).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX32).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX33).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a methyl group, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX34).
The Compound (TA) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX35).
The Compound (1A) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R3 and R4 represent any combination described in Combination A (hereinafter, referred to as Compound Class SX36).
A compound represented by formula (1B):
(hereinafter, referred to as Compound (1B))
Group V is a group consisting of Me,Et,Pr,i-Pr,c-Pr,c-Bu,c-Pen,c-Hex, (CH2)3CH3,CH2CH(CH3)2,CH(CH3)CH2CH3,t-Bu,CH2c-Pr, (CH2)4CH3, (CH2)2CH(CH3)2,CH(CH3) (CH2)2CH3, CH(CH2CH3)C H2 CH3, CH2 CH(CH3) CH2 CH3, C(CH3) 2 CH2 CH3, CH2 t-Bu, CH2c-Bu, CH2c-P en, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopro pyl)methyl,1-cyclopropylethyl, (CH2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3) 2, (CH2) 2 CH(CH3) CH2CH3, CH2CH(CH3) (CH2) 2 CH3, CH(CH3) (CH2) 3 CH3, CH2CH(CH2CH3) 2, heptyl, CH2CH═CH2, CH2CH═CHCH3, CH2CH═C(CH 3) 2, CH2CH═CF2, CH2CH═CCl2,CH2CH═CHCH2CH3, CH2CH═CH(CH2) 2 CH3, C H2C(CH3)═CH2, CH2C(CH3)═CHCH3, CH2C(CH3)═C(CH3) 2,CH2C(CH3)═CH CH2CH3, CH2CF═CH2, CH2CF═CHCH3, CH2CF═C(CH3) 2,CH2CF═CF2, CH2CF═CHCH2CH3,CH2CF═CH(CH2)2CH3, CH2CCl═CH2,CH2CCl═CHCH3, CH2CCl═C(CH3)2,Cl2CC1═CC12,CH2CC═CHCH2CH3,CH2CCl═CH(CH2)2CH3, (CH2)2CH═CH2, (CH2)2CH═CHCH3, (CH2)2CH═CHCH2CH3, (CH2)2CH═C(CH3)2, (CH2)2C(CH3)═CH2, (CH2)2C(CH3)═CHCH3, (CH2)3CH═CH2, (CH2)3C(CH 3)═CH2, (CH2) 4 CH═CH2, CH2C≡CH, CH2C≡CCH3, CH2C≡CCH2CH3, CH2C≡Cc-Pr, (CH2)2C° CH, (CH2)2C≡CCH3, (CH2)2C° CCH2CH3, (CH2)3C≡CH, (CH2) 3C≡CCH3,CH2Cl, CH2Br, CH2OCH3, CH2OCH2CH3, CH2O(CH2) 2 CH3, CHF2, C F3,CH2CF3,CH2CHF2,CH2CH2CHF2,CH2CH2CF3,CH2CF2CF3, (CH2)2CF2C F3,CH2 (CF2)2CF3, (CH2)2CF(CF3)2, (CH2)2 (CF2)5CF3,CF3,CF2CHF(C F3),CF2CHF(OCF3),CH2CF2CF2H,Ph,2-F-Ph,3-F-Ph,4-F-Ph,2-C1-Ph, 3-C1-Ph, 4-C1-Ph,2-Me-Ph,3-Me-Ph,4-Me-Ph,2-OMe-Ph,3-OMe-Ph,4-OMe-Ph,2-Pyridyl,3-Pyridyl,4-Pyridyl,2-Thienyl,3-Thienyl,2-pyrimidinyl,4-pyrimidinyl,5-pyrimidinyl,3-pyridazinyl,and 4-pyridazinyl.
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents methyl group, Rx2 represents an ethyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX38).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX39).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX40).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methoxy group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX41).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX42).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX43).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX44).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX45).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX46).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX47).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX48).
A compound (1B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX49).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX50).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX51).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX52).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methoxy group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX53).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX54).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX55).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX56).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX57).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX58).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX59).
A compound (1B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX60).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX61).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents an ethyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX62).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX63).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX64).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methoxy group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX65).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX66).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX67).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX68).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX69).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX70).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, RX2 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX71).
A compound (1B) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX72).
A compound represented by formula (2B):
(hereinafter, referred to as Compound (2B))
A compound (2B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx28 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX74).
A compound (2B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx28 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX75).
A compound (2B) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx28 represents a methoxy group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX76).
A compound (2B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX77).
A compound (2B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx28 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX78).
A compound (2B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx28 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX79).
A compound (2B) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methyl group, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX80).
A compound (2B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx28 represents a fluorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX81).
A compound (2B) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx28 represents a chlorine atom, and R5 represents any substituent selected from Group V (hereinafter, referred to as Compound Class SX82).
A compound represented by formula (lC):
(hereinafter, referred to as Compound (1C))
Group Y is a group consisting of Et,Pr,i-Pr, (CH2)3CH3, CH2CH(CH3)2,CH(CH3)CH2CH3,C(CH3)3,CH2c-Pr, (CH2)4CH3, (CH2)2C H(CH3)2,CH(CH3) (CH2)2CH3,CH(CH2CH3)CH2CH3,CH2CH(CH3)CH2CH3, C(CH3)2CH2CH3,CH2C(CH3)3,CH2c-Bu,CH2c-Pen,CH2c-Hex, (CH2)2c-Pr, (1-methylcyclopropyl)methyl, (2-methylcyclopropyl)methyl, 1-cyclopropylethyl, (CH2)3c-Pr, (CH2)5CH3, (CH2)3CH(CH3)2, (CH 2)2CH(CH3) CH2CH3, CH2CH(CH3) (CH2)2CH3, CH(CH3) (CH2)3CH3, CH2CH(CH2CH3) 2, heptyl, octyl, nonyl, decyl, CH2CH═CH2,CH2CH═CHCH3,CH2CH═C(CH3) 2, CH2CH═CF2, CH2CH═CCl2, CH2CH═CHCH2CH3, CH2CH═CH(CH 2) 2 CH3,CH2C(CH3)═CH2, CH2C(CH3)═CHCH3,CH2C(CH3)═C(CH3) 2, CH2C(CH3)═CHCH2CH3, CH2C(CH3)═CH(CH2)2CH3,CH2CF═CH2, CH2CF═CHCH3, CH2CF═C(CH3) 2,CH2CF═CF2, CH2CF═CHCH2CH3,CH2CF═CH(CH2)2CH3,CH 2 CC1═CH2, CH2CCl═CHCH3, CH2CC1═C(CH3) 2,CH2CC1═CC12, CH2CCl═CHC H2CH3,CH2CCl═CH(CH2)2CH3, (CH2)2CH═CH2, (CH2)2CH═CHCH3, (CH2)2CH═CHCH2CH3, (CH2)2CH═C(CH3)2, (CH2)2C(CH3)═CH2, (CH2)2C(CH3)═CHCH3, (CH2)2C(CH3)═CHCH2CH3, (CH2)2C(CH3)═C(CH3)2, (CH2)3CH═C H2, (CH2)3C(CH3)═CH2, (CH2)4CH═CH2, (CH2)4C(CH3)═CH2,CH2C≡CH,C H2C≡CCH3,CH2C≡CCH2CH3,CH2C=Cc-Pr, CH2C═CPh, (CH2)2C≡CH, (CH2)2C≡CCH3, (CH2)2C≡CCH2CH3, (CH2)2C=Cc-Pr, (CH2)2C° CPh, (CH2)3C CCH, (CH2)3C≡CCH3, (CH2)3C≡CCH2CH3, (CH2)3C≡Cc-Pr, (CH2)3C≡CPh,CH2C 1, CH2Br, CH2CN, CH2OCH3, CH2OCH2CH3,CH2C(CH2) 2 CH3,CH2SCH3, CH2S CH2CH3,CH2S(CH2)2CH3,CH2C(C) CH3, CH2C(C) CH2CH3, CH2C(C) Ph, CH2C(O)NH2,CH2C(O)NHCH3,CH2C(O)N(CH3)2,CH2C(O)NHPh,CH2C(O)N(CH 3) Ph, CH2C(C) OCH3, CH2C(C) OCH2CH3, CH2CC(C) Ph, CH2OC(C) OCH3,CH2OC(C) OCH2CH3,CH2OC(C) OPh, CH2OC(O) NHCH3, CH2OC(C) NHCH2CH3,CH2OC(C) NHPh, CH2CC(O) N(CH3) 2, CH2CC(C) N(CH3) CH2CH3,CH2CC(C) N(CH3)Ph,CH2OC(O)N(CH2CH3)2,CH2 (2-oxiranyl),CH2 (2-tetrahydrofur anyl),CH2 (2-tetrahydropyranyl),
CH2CH═NOCH3, CH2CH═NOCH2CH3, CH2CH═NOCH2Ph, CH2C(CH3)═NOCH3, CH 2 C(CH3)═NOCH2CH3,CH2C(CH3)═NOCH2Ph, (CH2) 2 F, CH2CF3, (CH2) 2 Cl, CH2CC13, (CH2)2Br, (CH2)2I, (CH2)2CF3, (CH2)2CN, (CH2)2NO2, (CH2)2OCH3, (CH2)2OCH2CH3, (CH2)2SCH3, (CH2)2SCH2CH3, (CH2)2SPh, (CH2)2NHCH3, (CH2)2N(CH3)2, (CH2)2NHPh, (CH2)2NHCH2Ph, (CH2)2N(CH3) CH2Ph, (CH2)2C(O)CH3, (CH2)2C(O)CH2CH3, (CH2)2C(O)Ph, (CH2)2C(O )NH2, (CH2)2C(O)NHCH3, (CH2)2C(C)N(CH3)2, (CH2)2C(C)NHPh, (CH2)2C(O)N(CH3) Ph, (CH2)2C(C)OCH3, (CH2)2C(O)OCH2CH3, (CH2)2NHC(C) CH3, (CH2)2NHC(O)CH2CH3, (CH2)2NHC(O)Ph, (CH2)2NCH3C(O)CH3, (CH 2)2NCH3C(O)CH2CH3, (CH2)2NCH3C(O) Ph, (CR2)2NHC(O)OCH3, (CH2)2N HC(C)OCH2CH3, (CH2)2NHC(C) OPh, (CH2)2NCH3C(O)OCH3, (CH2)2NCH3C(O)OCH2CH3, (CH2)2NCH3C(C)OPh, (CH2)2NHC(O)NHCH3, (CH2)2NHC(O) NHCH2CH3, (CH2)2NHC(C)NHPh, (CH2)2NHC(C)N(CH3)2, (CH2)2NHC(C)N(CH3)CH2CH3, (CH2)2NHC(O)N(CH3)Ph, (CH2)2NHC(C)N(CH2CH3)2, (CH 2)2NCH3C(O) NHCH3, (CH2) 2 NCH3C(O) NHCH2CH3, (CH2) 2NCH3C(O) NHPh, (CH)2NCH3C(O)N(CH3)2, (CH)2NCH3C(O)N(CH3)CH2CH3, (CH2)2NCH3C(O)N(CH3)Ph, (CH2)2NCH3C(O)N(CH2CH3)2, (CH2)2OC(O)CH3, (CH2)2OC(O) CH2CH3, (CH2) 2 OC(O) Ph, (CH2) 2 OC(O)OCH3, (CH2)2C(O)OCH2CH3, (CH2)2OC(O)OPh, (CH2)2OC(O)NHCH3, (CH2)2OC(O)NHCH2CH3, (CH2)2OC(O) NHPh, (CH2) 2 OC(O) N(CH3) 2, (CH2) 2 OC(O) N(CH3) CH2CH3, (CH2) 2 OC(O) N(CH3) Ph, (CH2) 2 OC(O) N(CH2CH3) 2, (CH2) 3 F, (CH2) 3 Cl, (CH2)3Br, (CH2)31, (CH2)3CF3, (CH2)3CN, (CH2)3N02, (CH2)3OCH3, (CH2)30CH2CH3, (CH2)3SCH3, (CH2)3SCH2CH3, (CH2)3NHCH3, (CH2)3N(CH3)2, (CH2)4F, (CH2)4Cl, (CH2)4CF3, (CH2)4CN, (CH2)4N02, (CH2)4Ph, (CH2)4OCH3, (CH2)4SCH3, (CH2)4NHCH3, (CH2)4N(CH3)2, (CH2)5F, (CH2)5Cl , (CH2)5CF3, (CH2)5CN, (CH2)5N02, (CH2)5Ph, (CH2)50CH3, (CH2)5SCH 3, (CH2)5NHCH3, (CH2) N(CH3) 2, (CH2) 6 F, (CH2)6Cl, (CH2)6CF3, (CH2)6CN, (CH2)6N02, (CH2)6Ph, (CH2)60CH3, (CH2)6SCH3, (CH2)6NHCH3 (CH2)6N(CH3)2,CH2CF2CF3, (CH2)2CF2CF3,CH2 (CF2)2CF3, (CH2)2CF(C F3) 2, (CH2) 2 (CF2) 5 CF3, CF3, CHF2, and CH2F.
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents an ethyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX84).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX85).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX86).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX87).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX88).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX89).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX90).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX91).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX92).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX93).
A compound (1C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX94).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX95).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX96).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX97).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX98).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methoxy group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX99).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX100).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX101).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX102).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX103).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX104).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX105).
A compound (1C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX106).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX107).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents an ethyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX108).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX109).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX110).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a methoxy group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX111).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX112).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX113).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX114).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX115).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, RX2 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX116).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX117).
A compound (1C) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX118).
A compound represented by formula (2C):
(hereinafter, referred to as Compound (2C))
A combination B consists of Substituent No. ZB1 to ZB306. The substituent No. ZB1 to ZB306 represent a combination of RX3, RX4, RX5, RX6, and RX7 in the compound (2C), a compound represented by formula (1D) and a compound represented by formula (2D), which is hereinafter as described as [Substituent No.; RX3, RX4, RX5, RX6, RX7]. For example, the Substituent No. ZB2 represents a combination wherein R3X represents a methyl group, and RX4, RX5, RX6, and RX7 represent a hydrogen atom.
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, m is 2, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX120).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a chlorine atom, m is 2, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX121).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, m is 2, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX122).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, m is 2, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX123).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methyl group, m is 3, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX124).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, m is 3, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX125).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a chlorine atom, m is 3, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX126).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, m is 3, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX127).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, m is 3, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX128).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methyl group, m is 4, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX129). an oxygen atom, R1 represents a methyl group, RX2 represents A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, m is 4, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX130).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a chlorine atom, m is 4, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX131).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, m is 4, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX132).
A compound (2C) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, m is 4, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX133).
A compound represented by formula (3C):
(hereinafter, referred to as Compound (3C))
A compound (3C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX135).
A compound (3C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX136).
A compound (3C) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methoxy group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX137).
A compound (3C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX138).
A compound (3C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX139).
A compound (3C) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX140).
A compound (3C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX28 represents a methyl group, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX141).
A compound (3C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX28 represents a fluorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX142).
A compound (3C) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX28 represents a chlorine atom, and R6 represents any substituent selected from Group Y (hereinafter, referred to as Compound Class SX143)
A compound represented by formula (1D):
(hereinafter, referred to as Compound (1D))
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents an ethyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX145).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX146).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX147).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX148).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a cyclopropyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX149).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX150).
A compound (iD) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX151).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX152).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX153).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX154).
A compound (1D) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX155).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX156).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents an ethyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX157).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX158).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX159).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX160). A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a cyclopropyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX161).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX162).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a fluorine atom, and RX3, RX4, RXs, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX163).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX164).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX165). A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX166).
A compound (1D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX167).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX168).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents an ethyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX169).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX170).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX171).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a methoxy group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX172).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a cyclopropyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX173).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX174).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, RX2 represents a fluorine group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX175).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, RX2 represents a chlorine group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX176).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, RX2 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX177).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, RX2 represents a fluorine atom, and RX3, RX4, RX5, RXE, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX178).
A compound (1D) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, RX2 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX179).
A compound represented by formula (2D):
(hereinafter, referred to as Compound (2D))
A compound (2D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX181).
A compound (2D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX182).
A compound (2D) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methoxy group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX183).
A compound (2D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX184).
A compound (2D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX185).
A compound (2D) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX28 represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX186).
A compound (2D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX28 represents a methyl group, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX187).
A compound (2D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX28 represents a fluorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX188).
A compound (2D) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2e represents a chlorine atom, and RX3, RX4, RX5, RX6, and RX7 represent any combination described in Combination B (hereinafter, referred to as Compound Class SX189).
A compound represented by formula (lE):
wherein G represents any one of formulae G1 to G36.
(hereinafter, referred to as Compound (1E))
Combination C consists of the Substituent No. ZC1 to ZC1459. The Substituent No. ZC1 to ZC1459 represent a combination of the structure of G and the substituents of RX8, RX9, RX10 and RX11 applied to the structure of G in the Compound (1E) and the compounds represented by formula (2E), which hereinafter, is described as [Substituent No.; G, RX8, RX9, RX10, RX11]. For example, the Substituent No. ZC2 represents a combination wherein G represents G1, RX8 represents a methyl group, and RX9, RX10, and RX11 represent a hydrogen atom.
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX191).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX192).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX193).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methoxy group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX194).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a cyclopropyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX195).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX196).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX197).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX198).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX199).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX200).
A compound (1E) wherein X represents CH, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX201).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX202).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents an ethyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX203).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX204).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX205).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and a combination of structure of G and substituent of RX5, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX206).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a cyclopropyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX207).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX208).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX209).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX210).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX211).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX212).
A compound (1E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX213).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a methyl group, and a combination of structure of G and substituent of RX9, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX214).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, Rx2 represents an ethyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX215).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX216).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX217).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a methoxy group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX218).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a cyclopropyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX219).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, RX2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX220).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX221).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a fluorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX222).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX223).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a fluorine atom, and a combination of structure of G and substituent of RX9, RX9, RX10 and RXI1 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX224).
A compound (1E) wherein X represents a nitrogen atom, L represents NH, R1 represents a chlorine atom, Rx2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX225).
A compound represented by formula (2E):
wherein G represents any one of formulae G1 to G36.
A compound (2E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX227).
A compound (2E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX228).
A compound (2E) wherein X represents CH, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methoxy group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX229).
A compound (2E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX230).
A compound (2E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX231).
A compound (2E) wherein X represents a nitrogen atom, L represents an oxygen atom, R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX232).
A compound (2E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a methyl group, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX233).
A compound (2E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX234).
A compound (2E) wherein X represents a nitrogen atom, L represents NH, R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of structure of G and substituent of RX8, RX9, RX10 and RX11 applied to the structure of G represents any combination described in Combination C (hereinafter, referred to as Compound Class SX235).
A compound represented by formula (1F):
(hereinafter, referred to as Compound (1F))
The combination D consists of the Substituents No. ZD1 to ZD30. The Substituent No. ZD1 to ZD30 represent the combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 in the compound (1F), which hereinafter is described as [Substituent No.; RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, RX20]. For example, the Substituent No. ZD2 represents a combination wherein RX12 represents a methyl group, and RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represent a hydrogen].
A compound (1F) wherein R1 represents a methyl group, RX2 represents an ethyl group, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX237).
A compound (1F) wherein R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX238).
A compound (1F) wherein R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX239).
A compound (1F) wherein R1 represents a methyl group, RX2 represents a methoxy group, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX240).
A compound (1F) wherein R1 represents a methyl group, RX2 represents a cyclopropyl group, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX241).
A compound (1F) wherein R1 represents a fluorine atom, RX2 represents a methyl group, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX242).
A compound (1F) wherein R1 represents a fluorine atom, RX2 represents a fluorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX243).
A compound (1F) wherein R1 represents a fluorine atom, RX2 represents a chlorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX244).
A compound (1F) wherein R1 represents a chlorine atom, RX2 represents a methyl group, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX245).
A compound (1F) wherein R1 represents a chlorine atom, RX2 represents a fluorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX246).
A compound (1F) wherein R1 represents a chlorine atom, Rx2 represents a chlorine atom, and a combination of RX12, RX13, RX14, RX15, RX16, RX17, RX18, RX19, and RX20 represents any combination described in Combination D (hereinafter, referred to as Compound Class SX247).
A compound represented by formula (2F):
(hereinafter, referred to as Compound (2F))
The Combination E consists of the Substituent No. ZE1 to ZE20. The Substituent No. ZE1 to ZE20 represent a combination of RX21, RX22, RX23, RX24, RX25, RX26 and RX27 in the Compound (2F), which is hereinafter described as [Substituent No.; RX21, RX22, RX23, RX24, RX25, RX26, RX27]. For example, the Substituent No. ZE2 represents a combination wherein Rx21 represents a methyl group, and Rx22, RX23, RX24, RX25, RX26 and Rx27 represent a hydrogen atom.
A compound (2F) wherein R1 represents a methyl group, RX2 represents an ethyl group, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX249).
A compound (2F) wherein R1 represents a methyl group, RX2 represents a fluorine atom, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX250).
A compound (2F) wherein R1 represents a methyl group, RX2 represents a chlorine atom, and a combination of Rx21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX251).
A compound (2F) wherein R1 represents a methyl group, RX2 represents a methoxy group, and a combination of Rx21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX252).
A compound (2F) wherein R1 represents a methyl group, RX2 represents a cyclopropyl group, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX253).
A compound (2F) wherein R1 represents a fluorine atom, RX2 represents a methyl group, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX254).
A compound (2F) wherein R1 represents a fluorine atom, RX2 represents a fluorine atom, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX255).
A compound (2F) wherein R1 represents a fluorine atom, RX2 represents a chlorine atom, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX256).
A compound (2F) wherein R1 represents a chlorine atom, RX2 represents a methyl group, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX257).
A compound (2F) wherein R1 represents a chlorine atom, RX2 represents a fluorine atom, and a combination of Rx21, RX22, RX23, RX24, RX25, RX26, and RX22 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX258).
A compound (2F) wherein R1 represents a chlorine atom, RX2 represents a chlorine atom, and a combination of RX21, RX22, RX23, RX24, RX25, RX26, and RX27 represents any combination described in Combination E (hereinafter, referred to as Compound Class SX259).
Next, the formulation examples of the compounds of the present invention are shown below. In the formulation examples, the “parts” represents “part by weight” unless otherwise specified. The present compound S represents the compounds described in the Compound Classes SX1 to SX259.
Thirty five (35) parts of a mixture of ammonium polyoxyethylene alkyl ether sulfate and wet silica (weight ratio: 1:1), 10 parts of any one of the present compound S, and 55 parts of water are mixed, and the mixture is then finely-ground by a wet grinding method to obtain a formulation.
Fifty (50) parts of any one of the present compound S, 3 parts of calcium lignin sulfonate, 2 parts of sodium lauryl sulfate, and 45 parts of silica are well mixed-grinding to obtain a formulation.
Five (5) parts of any one of the present compound S, 9 parts of polyoxyethylene styryl phenyl ether, 5 parts of polyoxyethylene decyl ether (Number of ethylene oxide additions: 5), 6 parts of calcium dodecylbenzene sulfonate and 75 parts of xylene are well mixed to obtain a formulation.
Two (2) parts of any one of the present compound S, 1 part of silica, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are mixed-grinding, and thereto is added an appropriate amount of water, and the mixture is well kneaded and is then granulated with a granulator and dried to obtain a formulation.
Ten (10) parts of any one of the present compound S is mixed with a mixture of 18 parts of benzyl alcohol and 9 parts of DMSO, and thereto are added 6.3 parts of GERONOL (registered trademark) TE250, 2.7 parts of Ethylan (registered trademark)NS-500LQ, and 54 parts of Solvent naphtha, and the mixture is mixed to obtain a formulation.
Zero point one (0.1) parts of any one of the present compound S is dissolved by mixing with 39.9 parts of kerosene, and the mixture is placed in an aerosol container, and 60 parts of liquefied petroleum gas (mixture of propane, butane and isobutane; saturated vapor pressure: 0.47 MPa (25° C.)) is filled in the container to obtain a formulation.
Zero point two (0.2) parts of any one of the present compound S, 50 parts of pyrethrum extract dreg powder, 30 parts of Machilus thunbergii powder, and 19.8 parts of wood powder are mixed, and an appropriate amount of water is added thereto, and the mixture is well kneaded, and is extructed with an extruder into a plate-like sheet, and the resulting sheet is made a spiral-like form thereof with a punching machine to obtain a formulation.
Next, Test Examples are described.
The untreated groups in Test Example 1 to Test Example 8 represent tested groups in which the same conditions as those of each of the Test Examples were conducted except that DMSO was dispensed in the place of a DMSO diluted solution comprising the present compound. Also the untreated groups in Test Example 9 to Test Example 19 represent tested groups in which an aqueous diluted solution of a formulation comprising the present compound is not applied. Further the untreated groups in Test
Example 20 and Test Example 23 represent tested groups in which an aqueous diluted solution of a formulation comprising the present compound is not applied.
The present compound 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 2-1, 3-1, 3-2, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 5-1, 6-1, 1-7, 1-8, 1-9, 2-2, 2-3, 3-3, 3-4, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of YBG medium to which conidia of Septoria tritici were inoculated in advance. This plate was cultured at 18° C. for 3 days, thereby allowing Septoria tritici to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of Septoria tritici. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 1-7, 1-8, 1-9, 2-3, 4-7, 4-9, 4-13, 4-14, 4-15, 4-16, 4-18, 4-19, or 4-20 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which spores of Phytophthora capsici were inoculated in advance. This plate was cultured at 27° C. for 3 days, thereby allowing Phytophthora capsici to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Phytophthora capsici. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-3, 1-5, 1-6, 1-7, 1-8, 1-9, 2-3, 3-1, 3-2, 3-4, 4-7, 4-8, 4-9, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-1, or 5-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of Czapek medium to which spores of Pythium ultimum were inoculated in advance. This plate was cultured at 23° C. for days, thereby allowing Pythium ultimum to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Pythium ultimum. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-5, 1-7, 1-8, 1-9, 2-3, 4-1, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-19, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, or 6-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Ustilago maydis were inoculated in advance. This plate was cultured at 18° C. for 4 days, thereby allowing Ustilago maydis to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Ustilago maydis. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Rhynchosporium secalis were inoculated in advance. This plate was cultured at 18° C. for 7 days, thereby allowing Rhynchosporium secalis to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Rhynchosporium secalis. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of complete medium to which conidia of Botrytis cinerea were inoculated in advance. This plate was cultured at 18° C. for 4 days, thereby allowing Botrytis cinerea to undergo proliferation, and the absorbance at 550 rim of each well of the titer plate was then measured to determine a degree of growth of the Botrytis cinerea. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, or 6-2 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of a potato dextrose broth (PDB broth) to which conidia of Cladosporium carpophilum were inoculated in advance. This plate was cultured at 18° C. for 5 days, thereby allowing Cladosporium carpophilum to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Cladosporium carpophilum. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
The present compound 1-2, 2-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-24, 4-25, 4-26, 4-27, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, or 5-5 was diluted with DMSO so as to contain 150 ppm, and 1 μL of the dilution solutions were dispensed into titer plate (96 well), and thereafter, thereto was then dispensed 150 μL of YB liquid medium to which conidia of Cochliobolus miyabeanus were inoculated in advance. This plate was cultured at 23° C. for 3 days, thereby allowing Cochliobolus miyabeanus to undergo proliferation, and the absorbance at 550 nm of each well of the titer plate was then measured to determine a degree of growth of the Cochliobolus miyabeanus. As a result, every of the growth in the well in treated groups treated with each of the present compounds showed 50% or less compared to the growth in an untreated well.
Soybean leaf (cv; Kurosengoku) was punched out to 1 cm diameter to prepare a leaf disk. Each 1 mL of an agar medium (agar concentration 1.2%) was dispensed in each well of 24 well microplate. A piece of the leaf disk was placed on agar medium on each well. To a mixture of 0.5 μL of Sorpol (registered trademark) 1200KX, 4.5 μL of DMSO, and 5 μL of xylene was added 20 μL of a solution containing 10000 ppm of the test compound in DMSO. The resulting mixture was diluted with ion exchange water to prepare a mixture containing a predetermined concentration of the test compound. The resulting mixture was sprayed in 10 μL per one leaf disk. After 1 day, an aqueous suspension of conidia of Phakopsora pachyrhizi having an amino acid substitution of F129L on mitochondrial cytochrome b protein (1.0×105/mL) was inoculated onto the leaf disks. After the inoculation, the microplate was placed in a growth chamber (light on for 6 hours, light off for 18 hours, 23° C. temperature, 60% humidity). After 1 day, the leaf disks were air-dried to disappear water droplets on the surface of the leaf disk, and the microplate was placed again in the growth chamber for 12 days. Thereafter, a lesion area of soybean rust disease was assessed. As a result, lesion areas in the leaf disk treated with any one of the present compounds 1-2, 2-1, 3-1, 3-2, 4-1, 4-2, 4-3, 4-4, 4-5, 4-6, 5-1, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 2-3, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 5-5, and 6-2 as a tested compound at a prescribed concentration of 50 ppm showed 30% or less compared to the lesion areas in an untreated leaf disk.
Each of plastic pots was filled with soil and thereto barley (cv; NISHINOHOSHI) seeds were sown and the barleys were grown in a greenhouse for 7 days. Thereafter, the present compound 1-2, 4-2, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 4-1, 4-6, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, or 5-4, each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be a prescribed concentration (200 ppm). The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned barley. After spraying the mixtures, the barleys were air-dried and after 1 day, an aqueous suspension of the conidia of Pyrenophora teres was spraying-inoculated. After the inoculation, the barleys were placed at 23° C. during daytime and 20° C. during nighttime under a high humidity for 3 day and then cultivated in a greenhouse for 7 days, and a lesion area was observed. As a result, every of the lesion areas in barleys treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated barley.
Each of plastic pots was filled with soil and thereto wheat (cv; SHIROGANE) seeds were sown and the wheats were grown in a greenhouse for 9 days. The present compound 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 3-1, 3-2, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 5-5, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm, and the mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and were then cultivated at 20° C. under lighting for 5 to 7 days. The conidia of Puccinia recondita were sprinkling-inoculated. After the inoculation, the wheats were placed under a dark and humid condition at 23° C. for 1 day and were then cultivated at 20° C. under lighting for 8 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.
Each of plastic pots was filled with soil and thereto wheat (cv; Apogee) seeds were sown and the wheats were grown in a greenhouse for 10 days. Thereafter, the present compound 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 3-1, 3-2, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and after 4 days, an aqueous suspension of the conidia of Septoria tritici was spraying-inoculated. After the inoculation, the wheats were placed at 18° C. under a high humidity for 3 days and then under lighting for 14 to 18 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.
Each of plastic pots was filled with soil and thereto wheat (cv; Apogee) seeds were sown and the wheats were grown in a greenhouse for 10 days. An aqueous suspension of the conidia of Septoria tritici was spraying-inoculated. After the inoculation, the wheats were placed at 18° C. under a high humidity for 3 days. Thereafter, the present compound 1-2, 2-1, 3-1, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 3-1, 4-1, 4-6, 4-7, 4-10, 4-12, 4-13, 4-14, 4-15, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-27, 4-28, 4-29, 5-1, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned wheat. After spraying the mixtures, the wheats were air-dried and were placed under lighting for 14 to 18 days, and a lesion area was observed. As a result, every of the lesion areas in wheats treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated wheat.
Each of plastic pots was filled with soils and thereto tomato (cv; PATIO) seeds were sown and the tomatoes were grown in a greenhouse for 20 days. Thereafter, the present compound 2-1, 3-2, 4-2, 4-3, 4-5, 1-1, 1-3, 1-4, 1-5, 1-6, 1-8, 1-9, 3-2, 4-1, 4-6, 4-7, 4-8, 4-9, 4-12, 4-13, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-28, 4-29, 5-1, 5-2, or 5-4, each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned tomato. After spraying the mixtures, the tomatoes were air-dried and after 1 day, an aqueous suspension of the spores of Phytophthora infestans were spraying-inoculated. After the inoculation, the tomatoes were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 day, and were then cultivated in a greenhouse for 4 days, and a lesion area was observed. As a result, every of the lesion areas in tomatoes treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated tomato.
Each of plastic pots was filled with soil and thereto soybean (cv: Kurosengoku) seeds were sown and the soybeans were grown in a greenhouse for 10 to 14 days. Thereafter, the present compound 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 3-1, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-1, 5-2, 5-3, 5-4, 5-5, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and after 2 to 5 days, an aqueous suspension of the conidia of Phakopsora pachyrhizi was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 to 2 days, and were then cultivated in the greenhouse for 12 days, and a lesion area was observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.
Each of plastic pots was filled with soil and thereto soybean (cv: Kurosengoku) seeds were sown and the soybeans were grown in a greenhouse for 10 days, and an aqueous suspension containing the conidia of Phakopsora pachyrhizi was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 1 day, and were then cultivated in the greenhouse for 2 days, and thereafter, the present compound 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-1, 1-3, 1-5, 1-6, 1-7, 1-8, 1-9, 3-1, 3-2, 3-3, 3-4, 4-1, 4-7, 4-8, 4-9, 4-10, 4-12, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-20, 4-22, 4-24, 4-29, 5-1, 5-4, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm, and the resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and cultivated in a greenhouse for 8 days, and a lesion area was then observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.
Each of plastic pots was filled with soil and thereto soybean (cv: Tachinagaha) seeds were sown and the soybeans were grown in a greenhouse for 13 days. Thereafter, the present compound 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-7, 1-8, 1-9, 3-1, 3-2, 4-14, 4-16, 4-17, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-27, 4-28, 4-29, 5-4, 5-5, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned soybean. After spraying the mixtures, the soybeans were air-dried and after 1 day, an aqueous suspension of the conidia of Cercospora sojina was spraying-inoculated. After the inoculation, the soybeans were placed in a greenhouse of 23° C. during daytime and 20° C. during nighttime under a high humidity for 3 days, and were then cultivated in the greenhouse for 16 days, and a lesion area was observed. As a result, every of the lesion areas in soybean treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated soybean.
Each of plastic pots was filled with soils and thereto tomato (cv; PATIO) seeds were sown and the tomatoes were grown in a greenhouse for 20 days. Thereafter, the present compound 2-1, 3-1, 3-2, 4-2, 4-3, 6-1, 1-5, 1-6, 1-7, 1-8, 1-9, 2-2, 3-1, 3-2, 3-3, 4-1, 4-6, 4-7, 4-8, 4-9, 4-10, 4-11, 4-12, 4-13, 4-14, 4-15, 4-16, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-24, 4-25, 4-26, 4-28, 4-29, 4-30, 5-1, 5-2, 5-3, 5-4, 5-5, 6-2, or 2-3 each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to foliar parts so as to adhere adequately on the leaves of the above-mentioned tomato. After spraying the mixtures, the tomatoes were air-dried and after 1 day, an aqueous suspension of the conidia of Alternaria solani were spraying-inoculated. After the inoculation, the tomatoes were placed at 18° C. under a high humidity for 6 days, and a lesion area was observed. As a result, every of the lesion areas in tomatoes treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated tomato.
Each of plastic pots was filled with soil and thereto Kidney bean (cv; NAGAUZURA SAITO) seeds were sown and the kidney beans were grown in a greenhouse for 8 days. Thereafter, the present compound 1-2, 2-1, 3-2, 4-2, 4-3, 4-4, 4-5, 6-1, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 3-2, 3-3, 3-4, 4-1, 4-6, 4-7, 4-9, 4-10, 4-12, 4-13, 4-14, 4-15, 4-17, 4-18, 4-19, 4-20, 4-21, 4-22, 4-23, 4-28, 4-29, 5-1, or 5-2, each of which was made to a formulation according to the similar method to that of Formulation Example 1, was mixed with water so as to be 200 ppm. The resulting mixtures were sprayed to the foliar parts so as to adhere adequately on the leaves of the above-mentioned kidney bean. After spraying the mixtures, the kidney beans were air-dried and a PDA medium containing hyphae of Sclerotinia sclerotiorum was placed on the leaves of the kidney bean. After the inoculation, all kidney beans were placed under a high humidity during only night and after 4 days, a lesion area was observed. As a result, every of the lesion areas in kidney beans treated with each of the present compounds showed 30% or less compared to the lesion area in an untreated kidney beans.
Test Method 20: Tests against cotton aphids
The test compounds is made to a formulation according to a similar method to that described in the Formulation Example 1, and thereto is added water containing 0.03 v/v % of a spreader to prepare a diluted solution containing a prescribed concentration of the test compound.
Cucumber (Cucumis sativus) seedling (on the developmental stage of the second true leaf) is planted in a container and approximately 30 cotton aphids (Aphis gossypii) (all stages of life) are released onto the leaves of the cucumber. After 1 day, the diluted solutions are sprayed into the seedling in a ratio of 10 mL/seedling.
Further, after 5 days, the number of the surviving insects is examined and the controlling value is calculated by the following equation.
Controlling value (%)={1-(CbxTai)/(CaixTb)}×100 wherein the symbols in the formula represent the following descriptions.
The test was conducted by making the prescribed concentration 500 ppm and using the below-mentioned compounds of the present invention as a test compound according to the test method 20. As a result of the test, the below-mentioned compounds of the present invention showed 90% or greater as the controlling value.
Compound of the present invention: 1-2, 2-1, 3-1, 3-2, 4-2, 4-3, 6-1, 1-1, 1-6, 1-7, 1-9, 4-1, 4-7, 4-9, 4-10, 4-11, 4-12, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-23, 4-24, 4-25, 4-29, 5-1, and 6-2.
Test Method 21: Tests against brown planthoppers
The test compounds are made to a formulation according to a similar method to that described in the Formulation Example 1, and thereto is added water containing 0.03 v/v % of Shindain (registered trademark) to prepare a diluted solution containing a prescribed concentration of the test compound.
Rice (Oryza sativa) seedling (on the developmental stage of the second true leaf) is planted in a container, and the diluted solutions are sprayed into the seedling in a ratio of 10 mL/seedling. Thereafter, 20 of 3rd instar larvae of brown planthoppers (Nilaparvata lugens) are released onto the rice leaves. After 6 days, the morality is calculated by the following equation.
Morality(%)={1−the number of the surviving insects/20}×100
The test was conducted by making the prescribed concentration 500 ppm and using the below-mentioned compounds of the present invention as a test compound according to the test method 21. As a result of the test, the below-mentioned compound of the present invention showed 90% or greater as the mortality.
Compound of the present invention: 1-2, 2-1, 3-1, 3-2, 6-1, 1-6, 1-7, 1-9, 2-2, 3-3, 4-7, 4-14, 4-15, 4-16, 4-17, 4-18, 4-19, 4-22, 4-29, and 6-2
Test compounds are made to a formulation according to a similar method to that described in the Formulation example 1, and thereto is added water containing 0.03 v/v % of Shindain (registered trademark) to prepare a diluted solution containing a prescribed concentration of the test compound.
Cabbage (Brassicae oleracea) seedling (on the developmental stage of the second to third true leaf) is planted in a cup, and the diluted solutions are sprayed into the seedling at a ratio of 20 mL/seedling. Thereafter, the stem and leaf thereof is cut out and then is installed into a cup that is covered with filter paper on the bed of the cup. Five (5) diamondback moth (Plutella xylostella) at the second instar larval stage are released into the cup. After 5 days, the number of the surviving insects is counted, and the mortality of insects is calculated by the following equation.
Mortality(%)=(1−Number of surviving insects/5)×100
The test was conducted by making the prescribed concentration 500 ppm and using the below-mentioned compounds of the present invention as a test compound according to the test method 22. As a result of the test, the below-mentioned compound of the present invention showed 80% or greater as the mortality.
Compound of the present invention: 3-1, 3-2, 4-2, 6-1, 4-7, 4-15, 4-18, 4-13, 1-7, 1-8, 1-9, 4-14, 4-17, 4-29, 4-22, 4-23, 4-24, and 4-25
The test compounds is made to a formulation according to a similar method to that described in the Formulation Example 1, and thereto is added water containing 0.03 v/v % of Shindain (registered trademark) to prepare a diluted solution containing a prescribed concentration of the test compound.
Kidney bean (Phaseolus vulgaris) seedling (on the developmental stage of the first true leaf) is planted in a container and approximately 40 adult female of common red spider mites (Tetranychus urticae) are released onto the leaves of the kidney bean. After 1 day, the diluted solutions are sprayed into the seedling in a ratio of 10 mL/seedling. Further, after 13 days, the number of the surviving insects is examined and the controlling value is calculated by the following equation.
Controlling value(%)={1−(Cb×Tai)/(Cai×Tb)}×100
wherein the symbols in the formula represent the following descriptions.
The test was conducted by making the prescribed concentration 500 ppm and using the below-mentioned compounds of the present invention as a test compound according to the test method 23. As a result of the test, the below-mentioned compound of the present invention showed 90% or greater as the controlling value.
Compound of the present invention: 1-2, 2-1, 3-1, 3-2, 4-2, 6-1, 1-3, 1-6, 2-2, 2-3, 3-3, 4-7, 4-9, 4-10, 4-11, 4-15, 4-16, 4-17, 4-18, 4-19, 4-21, 4-22, 4-24, 4-25, 4-27, 4-29, and 5-5.
The compound of the present invention has efficacies for controlling pests and can be used to control pests.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2021-029651 | Feb 2021 | JP | national |
| 2021-124464 | Jul 2021 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2022/008031 | 2/25/2022 | WO |
