Patent Application
20230357232
The present invention relates to an imidazo[1,2-a]pyridine compound and a pest control agent. More specifically, the present invention relates to an imidazo[1,2-a]pyridine compound that has excellent insecticidal activity and/or acaracidal activity, is excellent in safety, and may be industrially advantageously synthesized, and a pest control agent containing the same as an active ingredient.
Various compounds having insecticidal or acaracidal activity have been proposed. For practical use of such compounds as agrochemicals, it is required not only to have sufficiently high efficacy but to be less likely to cause chemical resistance, to cause neither phytotoxicity to plants nor soil pollution, and to be low toxic to livestock, fishes, etc.
Patent document 1 discloses a compound of formula (A) etc.
Patent document 1: WO2017/104741
An object of the present invention is to provide an imidazo[1,2-a]pyridine compound that is excellent in pest control activity, particularly, insecticidal activity and/or acaracidal activity, is excellent in safety, and may be industrially advantageously synthesized. Another object of the present invention is to provide a pest control agent, an insecticide or acaracide, an ectoparasite control agent, or an endoparasite control agent or expellant containing the imidazo[1,2-a]pyridine compound as an active ingredient.
As a result of diligent studies to attain the objects, the present invention including the following form has been completed.
[1] A compound of any of formulae (I) to (III) or a salt thereof:
wherein
[2] A pest control agent comprising at least one active ingredient selected from the group consisting of a compound according to [1] and a salt thereof.
[3] An insecticide or acaracide comprising at least one active ingredient selected from the group consisting of a compound according to [1] and a salt thereof.
[4] An ectoparasite control agent comprising at least one active ingredient selected from the group consisting of a compound according to [1] and a salt thereof.
[5] An endoparasite control agent or expellant comprising at least one active ingredient selected from the group consisting of a compound according to [1] and a salt thereof.
The imidazo[1,2-a]pyridine compound of the present invention (a compound of any of formulae (I) to (III) or a salt thereof) may control pests that are problems associated with crops and hygiene. Particularly, the imidazo[1,2-a]pyridine compound of the present invention may effectively control agricultural insect pests and mites at a lower concentration. Furthermore, the imidazo[1,2-a]pyridine compound of the present invention may effectively control ectoparasites and endoparasites harmful to humans and animals.
The imidazo[1,2-a]pyridine compound of the present invention is a compound of formulae (I) to (III) (hereinafter, also referred to as compound (I) to (III) ) or a salt thereof.
In the present invention, the term “unsubstituted” means a group consisting of only a mother nucleus. Only the name of a group consisting of a mother nucleus without the term “substituted” means an “unsubstituted” group unless otherwise specified.
On the other hand, the term “substituted” means that any hydrogen atom of a group consisting of a mother nucleus is substituted with a group (substituent) having a structure that is the same as or different from that of the mother nucleus. Thus, the “substituent” means another group bonded to the group consisting of a mother nucleus. The number of the substituent may be one or more. Two or more substituents are the same or different.
Terms such as “C1-6” mean that the number of carbon atoms in the group consisting of a mother nucleus is 1 to 6, etc. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified into a C2 alkoxy C4 alkyl group.
The “substituent” is not particularly limited as long as the substituent is chemically acceptable and produces the effect of the present invention. Hereinafter, a group capable of serving as the “substituent” is exemplified:
For these “substituents”, any hydrogen atom in each substituent may be substituted with a group having a distinct structure. In this case, as the “substituent”, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group or the like may be exemplified.
The “3- to 6-membered heterocyclyl group” described above contains 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring-constituting atoms. The heterocyclyl group may be either monocyclic or polycyclic. The polycyclic heterocyclyl group has at least one hetero ring, and the remaining ring(s) may be any of a saturated alicyclic ring, an unsaturated alicyclic ring and an aromatic ring. As the “3- to 6-membered heterocyclyl group”, a 3- to 6-membered saturated heterocyclyl group, a 5- or 6-membered heteroaryl group, a 5- or 6-membered partially unsaturated heterocyclyl group or the like may be exemplified.
As the 3- to 6-membered saturated heterocyclyl group, an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, a dioxanyl group or the like may be exemplified.
As the 5-membered heteroaryl group, a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group or the like may be exemplified.
As the 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group or the like may be exemplified.
In the formulae (I) to (III), R1 represents a substituted or unsubstituted C1-6 alkylsulfonyl group.
As the “C1-6 alkylsulfonyl group” represented by R1, a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group or the like may be exemplified.
As the substituents on the “C1-6 alkylsulfonyl group” represented by R1, a halogeno group such as a fluoro group, a chloro group, a bromo group, and an iodo group may be preferably exemplified.
In the formulae (I) to (III), R2 and R3 each independently represent a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or a halogeno group.
The “C1-6 alkyl group” represented by R2 and R3 may be linear or branched. As the “C1-6 alkyl group”, a methyl group, an ethyl group, a n-propyl group, a n-butyl group, a n-pentyl group, a n-hexyl group, an i-propyl group, an i-butyl group, a s-butyl group, a t-butyl group, an i-pentyl group, a neopentyl group, a 2-methylbutyl group, an i-hexyl group or the like may be exemplified.
As the substituent on the “C1-6 alkyl group” represented by each of R2 and R3, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group may be preferably exemplified.
As the “halogeno group” represented by each of R2 and R3, a fluoro group, a chloro group, a bromo group, an iodo group or the like may be exemplified.
In the formulae (I) to (III), R is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.
As the “substituted or unsubstituted C1-6 alkyl group” represented by R, the same group as exemplified for R2 and R3 above is exemplified.
The “substituted C1-6 alkyl group” represented by R is preferably a C1-6 haloalkyl group.
As the “C1-6 haloalkyl group”, a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoromethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group, a 2,4,6-trichlorohexyl group or the like may be exemplified.
As the “C2-6 alkenyl group” represented by R, a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 1-methyl-2-propenyl group, a 2-methyl-2-propenyl group, a 1-pentenyl group, a 2-pentenyl group, a 3-pentenyl group, a 4-pentenyl group, a 1-methyl-2-butenyl group, a 2-methyl-2-butenyl group, a 1-hexenyl group, a 2-hexenyl group, a 3-hexenyl group, a 4-hexenyl group, a 5-hexenyl group or the like may be exemplified.
As the substituent on the “C2-6 alkenyl group”, a halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group; and C1-6 alkoxy groups such a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group may be preferably exemplified.
The “C6-10 aryl group” represented by R means a monocyclic or polycyclic aromatic hydrocarbon group, and the polycyclic aryl group includes a partially saturated group in addition to a fully unsaturated group. For example, a phenyl group, a naphthyl group, an indenyl group, an indanyl group or the like may be exemplified.
The “5- to 6-membered heteroaryl group” represented by R means a 5- to 6-membered aromatic heterocyclic group having 1 to 4 nitrogen atoms, oxygen atoms or sulfur atoms as hetero atoms. For example, 5-membered heteroaryl groups such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group (specifically, a [1,2,3]triazolyl group or a [1,2,4]triazolyl group), an oxadiazolyl group (specifically, a [1,2,4]oxadiazolyl group or a [1,3,4]oxadiazolyl group), a thiadiazolyl group, and a tetrazolyl group; 6-membered heteroaryl groups such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group; and the like may be exemplified.
As the substituents on the “C6-10 aryl group” and the “5- to 6-membered heteroaryl group” represented by R, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group, and a trifluoromethoxy group may be exemplified.
In the formulae (I) to (III), X is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C2-6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C1-6 alkoxycarbonyl group, a substituted or unsubstituted C1-6 alkylthio group, a substituted or unsubstituted C1-6 alkylsulfinyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C3-8 cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted 5- to 6-membered heteroaryl group, a substituted or unsubstituted C6-10 aryloxy group, a substituted or unsubstituted 5- to 6-membered heteroaryloxy group, a substituted or unsubstituted amino group, a substituted or unsubstituted aminocarbonyl group, a substituted or unsubstituted hydrazinyl group, a nitro group, a cyano group or a halogeno group.
As the “substituted or unsubstituted C1-6 alkyl group” and the “halogeno group” represented by X, the same groups as exemplified for R2 and R3 above are exemplified.
As the “C1-6 alkylsulfonyl group” represented by X, the same group as exemplified for R1 above is exemplified.
As the “substituted or unsubstituted C2-6 alkenyl group”, the “substituted or unsubstituted C6-10 aryl group” and the “substituted or unsubstituted 5- to 6-membered heteroaryl group” represented by X, the same groups as exemplified for R above are exemplified.
As the “C2-6 alkynyl group” represented by X, an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 1-methyl-2-propynyl group, a 2-methyl-3-butynyl group, a 1-pentynyl group, a 2-pentynyl group, a 3-pentynyl group, a 4-pentynyl group, a 1-methyl-2-butynyl group, a 2-methyl-3-pentynyl group, a 1-hexynyl group, a 1,1-dimethyl-2-butynyl group or the like may be exemplified.
As the “C1-6 alkoxy group” represented by X, a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group, a t-butoxy group or the like may be exemplified.
As the “C1-6 alkoxycarbonyl group” represented by X, a methoxycarbonyl group, an ethoxycarbonyl group, a n-propoxycarbonyl group, an i-propoxycarbonyl group, a n-butoxycarbonyl group, a t-butoxycarbonyl group or the like may be exemplified.
As the “C1-6 alkylthio group” represented by X, a methylthio group, an ethyl thio group, a n-propylthio group, a n-butylthio group, a n-pentylthio group, a n-hexylthio group, an i-propylthio group, an i-butylthio group or the like may be exemplified.
As the “C1-6 alkylsulfinyl group” represented by X, a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group or the like may be exemplified.
As the substituent on the “C1-6 alkyl group” represented by X, a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; a C1-6 alkoxy group such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group or a t-butoxy group; or a C1-6 alkoxyimino group such as a methoxyimino group, an ethoxyimino group, a n-propoxyimino group, an i-propoxyimino group or a n-butoxyimino group may be preferably exemplified.
As the substituents on the “C2-6 alkenyl group”, the “C2-6 alkynyl group”, the “C1-6 alkoxy group”, the “C1-6 alkylthio group”, the “C1-6 alkylsulfinyl group” and the “C1-6 alkylsulfonyl group” represented by X, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; and C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group may be preferably exemplified.
As the “C3-8 cycloalkyl group” represented by X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group or the like may be exemplified.
As the “C6-10 aryloxy group” represented by X, a phenoxy group, a naphthyloxy group or the like may be exemplified.
As the “5- to 6-membered heteroaryloxy group” represented by X, a pyridyloxy group, a pyrimidyloxy group or the like may be exemplified.
As the substituents on the “C3-8 cycloalkyl group”, the “C6-10 aryloxy group” and the “5- to 6-membered heteroaryloxy group” represented by X, halogeno groups such as a fluoro group, a chloro group, a bromo group and an iodo group; C1-6 alkyl groups such as a methyl group, an ethyl group, a n-propyl group, an i-propyl group, a n-butyl group, a s-butyl group, an i-butyl group, a t-butyl group, a n-pentyl group and a n-hexyl group; C1-6 haloalkyl groups such as a fluoromethyl group, a difluoromethyl group, a trifluoromethyl group, a 2,2,2-trifluoroethyl group, a pentafluoroethyl group, a 3,3,3-trifluoropropyl group, a 2,2,3,3,3-pentafluoropropyl group, a perfluoropropyl group, a 2,2,2-trifluoro-1-trifluoromethylethyl group, a perfluoroisopropyl group, a 4-fluorobutyl group, a 2,2,3,3,4,4,4-heptafluorobutyl group, a perfluorobutyl group, a perfluoropentyl group, a perfluorohexyl group, a chloromethyl group, a bromomethyl group, a dichloromethyl group, a dibromomethyl group, a trichloromethyl group, a tribromomethyl group, a 1-chloroethyl group, a 2,2,2-trichloroethyl group, a 4-chlorobutyl group, a perchlorohexyl group and a 2,4,6-trichlorohexyl group; C1-6 alkoxy groups such as a methoxy group, an ethoxy group, a n-propoxy group, an i-propoxy group, a n-butoxy group, a s-butoxy group, an i-butoxy group and a t-butoxy group; and C1-6 haloalkoxy groups such as a 2-chloro-n-propoxy group, a 2,3-dichlorobutoxy group and a trifluoromethoxy group may be preferably exemplified.
The “substituted or unsubstituted amino group” represented by X is a group represented by “—NRaRb”. As Ra and Rb in the formula, each independently, a hydrogen atom, a C1-6 alkyl group, a formyl group, a C1-6 alkylcarbonyl group, a substituted or unsubstituted aminocarbonyl group or the like may be exemplified.
As the “C1-6 alkyl group” represented by each of Ra and Rb, the same group as exemplified for R2 and R3 above is exemplified.
As the “C1-6 alkylcarbonyl group” represented by each of Ra and Rd, an acetyl group, a propionyl group or the like may be exemplified.
As the “substituted or unsubstituted aminocarbonyl group” represented by each of Ra and Rd, an aminocarbonyl group, a methylaminocarbonyl group, an ethylaminocarbonyl group, a dimethylaminocarbonyl group or the like may be exemplified.
As the “substituted or unsubstituted aminocarbonyl group” represented by X, the same group as exemplified for Ra and Rb above is exemplified.
The “substituted or unsubstituted hydrazinyl group” represented by X is a group represented by the formula (a).
In the formula (a), * represents a binding position, Rc, Rd and Re each independently represent a hydrogen atom, a C1-6 alkyl group or a substituted or unsubstituted phenylsulfonyl group.
As the “C1-6 alkyl group” represented by each of Rc, Rd and Re, the same group as exemplified for X above is exemplified.
As the “substituted phenylsulfonyl group” represented by each of Rc, Rd and Re, a paratoluenesulfonyl group or the like may be exemplified.
In the formula (I), n represents a number of chemically acceptable Xs, and is an integer of 0 to 4. Xs are the same or different when n is 2 or more.
In the formula (III), A represents a nitrogen atom or CR2.
As R2 in CR2, the same group as exemplified for R2 above is exemplified.
The salt of each of the compounds (I) to (III) is not particularly limited as long as the salt is agriculturally or horticulturally acceptable. As the salt of each of the compounds (I) to (III), for example, a salt of an inorganic acid such as hydrochloric acid and sulfuric acid; a salt of an organic acid such as acetic acid and lactic acid; a salt of an alkali metal such as lithium, sodium and potassium; a salt of an alkaline earth metal such as calcium and magnesium; a salt of a transition metal such as iron and copper; ammonia; a salt of an organic base such as triethylamine, tributylamine, pyridine and hydrazine; or the like may be exemplified.
The method for producing the compounds (I) to (III) or salts thereof is not particularly limited. For example, the compounds (I) to (III) of the present invention or salts thereof may be obtained by known methods described in Examples, etc. Alternatively, the salts of the compounds (I) to (III) may be obtained by known approaches from the compounds (I) to (III).
The imidazo[1,2-a]pyridine compound of the present invention is excellent in control effect on pests such as various agricultural insect pests and mites affecting the growth of plants.
Also, the imidazo[1,2-a]pyridine compound of the present invention is a highly safe substance because of less phytotoxicity to crops and low toxicity to fishes and warm-blooded animals. Hence, the imidazo[1,2-a]pyridine compound of the present invention is useful as an active ingredient for insecticides or acaracides.
Furthermore, in recent years, many insect pests such as diamondback moth, white-backed plant hopper, leafhopper, and aphid have developed resistance to various existing chemicals, causing problems of insufficient efficacy of these chemicals. Thus, chemicals effective for insect pests of resistant strains have been desired. The imidazo[1,2-a]pyridine compound of the present invention exhibits an excellent control effect not only on sensitive strains but also on insect pests of various resistant strains and even mites of miticide-resistant strains.
The imidazo[1,2-a]pyridine compound of the present invention is excellent in control effect on ectoparasites and endoparasites harmful to humans and animals. Also, the imidazo[1,2-a]pyridine compound of the present invention is a highly safe substance because of low toxicity to fishes and warm-blooded animals. Hence, the imidazo [1, 2-a]pyridine compound of the present invention is useful as an active ingredient for ectoparasite and endoparasite control agents.
The imidazo[1,2-a]pyridine compound of the present invention exhibits efficacy at every developmental stage of organisms to be controlled, and exhibits an excellent control effect on, for example, eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.
The pest control agent of the present invention contains at least one active ingredient selected from the imidazo[1,2-a]pyridine compounds of the present invention. The amount of the imidazo[1,2-a]pyridine compound contained in the pest control agent of the present invention is not particularly limited as long as its pest control effect is exhibited. The pest control agent is an agent controlling pests and includes an insecticide or acaracide, an ectoparasite control agent, or an endoparasite control agent or expellant, or the like.
The insecticide or acaracide of the present invention contains at least one active ingredient selected from the imidazo[1,2-a]pyridine compounds of the present invention. The amount of the imidazo[1,2-a]pyridine compound contained in the insecticide or acaracide of the present invention is not particularly limited as long as its insecticidal or acaracidal effect is exhibited.
The pest control agent or the insecticide or acaracide of the present invention is preferably used for plants such as cereals; vegetables; root vegetables; tubers and roots; flowers and ornamental plants; fruit trees; ornamental foliage plants and trees of tea, coffee, cacao, and the like; feed crops; lawn grasses; and cotton.
In the application to plants, the pest control agent or the insecticide or acaracide of the present invention may be used for any site such as a leaf, a stem, a stalk, a flower, a bud, a fruit, a seed, a sprout, a root, a tuber, a tuberous root, a shoot, or a slip.
The pest control agent or the insecticide or acaracide of the present invention is not particularly limited by the species of the plant to which the pest control agent or the insecticide or acaracide is applied. As the plant species, for example, an original species, a variant species, an improved variety, a cultivar, a mutant, a hybrid, a genetically modified organism (GMO) or the like may be exemplified.
The pest control agent of the present invention may be used in seed treatment, foliage application, soil application, submerged application, or the like in order to control various agricultural insect pests and mites.
Specific examples of various agricultural insect pests and mites controllable with the pest control agent of the present invention will be shown below.
The pest control agent of the present invention may be used as a mixture or in combination with another active ingredient such as a fungicide, an insecticide or acaracide, a nematicide, or a pesticide for soil insect pests; a plant regulating agent, a synergist, a fertilizer, a soil improvement agent, animal feed, or the like.
The combination of the compound of the present invention with another active ingredient may be expected to have synergistic effects on insecticidal, acaracidal, or nematicidal activity. The synergistic effects may be confirmed by the equation of Colby (Colby. S.R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, p. 20-22, 1967) according to a standard method.
Specific examples of the insecticide or acaracide, the nematicide, the pesticide for soil insect pests, the anthelmintic agent, and the like that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.
(1) Acetylcholinesterase inhibitors:
(2) GABAergic chloride ion channel antagonists: acetoprole, chlordene, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, and dienochlor.
Sodium channel modulators: acrinathrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin,β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin, α-cypermethrin, β-cypermethrin, θ-cypermethrin, ζ-cypermethrin, cyphenothrin [(1R)-trans isomer], deltamethrin, empenthrin [(EZ)-(1R)-Isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, τ-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrins, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, metofluthrin, protrifenbute, pyresmethrin, and terallethrin.
(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, and flupyrimine.
Nicotinic acetylcholine receptor allosteric modulators: spinetoram and spinosad.
Chloride channel activators: abamectin, emamectin -benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, and nemadectin.
Juvenile hormone-like substances: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, diofenolan, epofenonane, and triprene.
Other nonspecific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, and tartar emetic.
Homoptera selective feeding inhibitors: flonicamid, pymetrozine, and pyrifluquinazon.
(10) Mite growth inhibitors: clofentezine, diflovidazin, hexythiazox, and etoxazole.
Insect midgut inner membrane disrupting agents derived from microorganisms: bacillus thuringiensis subsp. Israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki, bacillus thuringiensis subsp. tenebrionis, and Bt crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, and Cry34Ab1, Cry35Ab1.
Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, and tetradifon.
Oxidative phosphorylation uncouplers: chlorfenapyr, sulfluramid, DNOC, binapacryl, dinobuton, and dinocap.
Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium, and thiocyclam.
Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, and fluazuron.
Diptera molting disrupting agents: cyromazine.
Molting hormone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, and tebufenozide.
Octopamine receptor agonists: amitraz, demiditraz, and chlordimeform.
Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, and hydramethylnon.
Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, and rotenone.
(21) Voltage-gated sodium channel blockers: indoxacarb and metaflumizone.
Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, and spirotetramat.
Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, and cyanide.
Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, and pyflubumide.
Ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, and tetraniliprole.
Mixed function oxidase inhibitor compounds: piperonyl butoxide.
Latrophilin receptor agonists: depsipeptide, cyclodepsipeptide, 24 membered cyclodepsipeptide, and emodepside.
Other agents (based on an unknown mechanism of action): azadirachtin, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, japonilure, metoxadiazone, oil, potassium oleate, tetrasul, triarathene, afidopyropen, flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitrile (CAS: 943137-49-3), broflanilide, and other m-diamides.
(29) Anthelmintic agents:
Specific examples of the fungicide that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.
Nucleic acid biosynthesis inhibitors:
(2) Mitotic inhibitors and cell division inhibitors:
(3) Respiration inhibitors:
(4) Amino acid and protein synthesis inhibitors
(5) Signal transduction inhibitors:
(6) Lipid and cell membrane synthesis inhibitors:
(7) Cell membrane sterol biosynthesis inhibitors:
(8) Cell wall synthesis inhibitors
(9) Melanin biosynthesis inhibitors
(10) Host plant resistance inducers:
(11) Agents with unknown mode of action: cymoxanil, fosetyl-aluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, flusulfamide, diclomezine, methasulfocarb, cyflufenamid, metrafenone, pyriofenone, dodine, dodine free base, and flutianil.
(12) Agents having multiple active sites: copper (copper salt), bordeaux mixture, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, ferbam, mancozeb, maneb, mancopper, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlofluanid, tolylfluanid, guazatine, iminoctadine triacetate, iminoctadine trialbesilate, anilazine, dithianon, quinomethionate, and fluoroimide.
(13) Other agents: DBEDC, fluorofolpet, guazatine acetate, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, cyprofuram, agrobacterium, bethoxazin, diphenylamine, methyl isothiocyanate (MITC), mildiomycin, capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate flumetover, fosetyl-calcium, fosetyl-sodium, irumamycin, natamycin, nitrothal isopropyl, oxamocarb, propamocin-sodium, pyrrolnitrin, tebufloquin, tolnifanide, zarilamide, Algophase, Amicarthiazol, Oxathiapiprolin, metiram zinc, benthiazole, trichlamide, uniconazole, mildiomycin, Oxyfenthiin, and picarbutrazox.
Specific examples of the plant regulating agent that may be used as a mixture or in combination with the pest control agent of the present invention will be shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl aminoethoxyvinyl glycine (also called aviglycine), aminooxyacetate, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyrate, dichlorprop, phenothiol, 1-naphthyl acetamide, ethychlozate, cloxyfonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxystrigol, (+)-orobanchol, (+)-sorgolactone, 4-oxo-4-(2-phenylethyl)aminobutyric acid, ethephon, chlormequat, mepiquat chloride, benzyladenine, and 5-amino levulinic acid.
The ectoparasite control agent of the present invention contains at least one active ingredient selected from the imidazo[1,2-a]pyridine compounds of the present invention. The amount of the imidazo[1,2-a]pyridine compound contained in the ectoparasite control agent of the present invention is not particularly limited as long as its ectoparasite control effect is exhibited.
As the host animal to be treated with the ectoparasite control agent of the present invention, a warm-blooded animal such as a human and a livestock mammal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as salmon, trout, and koi may be exemplified. In addition, a bee, a stag beetle and a beetle may be exemplified.
The ectoparasite control agent of the present invention may be applied by a known veterinary approach (local, oral, parenteral or subcutaneous administration). As the method therefor, a method of orally administering tablets, capsules, feed or the like containing the ectoparasite control agent to animals; a method of administering the ectoparasite control agent through dipping liquids, suppositories, injection (intramuscular, subcutaneous, intravenous, or intraperitoneal injection, etc.) or the like to animals; a method of locally administering oily or aqueous liquid formulations by spraying, pour-on, spot-on or the like; and a method of kneading the ectoparasite control agent into a resin, shaping the kneaded product into a suitable shape such as a collar or an ear tag, and attaching it to animals for local administration; or the like may be exemplified.
Ectoparasites parasitize the inside or the body surface of host animals, particularly, warm-blooded animals. Specifically, the ectoparasites parasitize the backs, armpits, lower abdomens, inner thighs, or the like of host animals and live by obtaining nutrients such as blood or dandruff from the animals. As the ectoparasite, mites, lice, fleas, a mosquito, a stable fly, a flesh fly or the like may be exemplified. Specific examples of the ectoparasite controllable with the ectoparasite control agent of the present invention will be shown below.
(1) Acari mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Ixodidae, mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae, and insect parasitic mites such as mites of the family Canestriniidae.
The order Phthiraptera lice of the family Haematopinidae, lice of the family Linognathidae, bird lice of the family Menoponidae, bird lice of the family Philopteridae, and bird lice of the family Trichodectidae.
The order Siphonaptera fleas of the family Pulicidae, for example, Ctenocephalides canis and Ctenocephalides felis of Ctenocephalides spp.; fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae.
The order Hemiptera
Insect pests of the order Diptera mosquitos of the family Culicidae, black flies of the family Simuliidae, biting midges of the family Ceratopogonidae, horseflies of the family Tabanidae, flies of the family Muscidae, tsetse flies of the family Glossinidae, flesh flies of the family Sarcophagidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.
The endoparasite control agent or expellant of the present invention contains at least one active ingredient selected from the imidazo[1,2-a]pyridine compounds of the present invention. The amount of the imidazo[1,2-a]pyridine compound contained in the endoparasite control agent or expellant of the present invention is not particularly limited as long as its endoparasite control effect is exhibited.
The parasite targeted by the endoparasite control agent or expellant of the present invention parasitizes the inside of host animals, particularly, warm-blooded animals or fishes (endoparasite). As the host animal for which the endoparasite control agent or expellant of the present invention is effective, a warm-blooded animal such as a human and a livestock mammal (e.g., a cow, a horse, a pig, sheep, and a goat), a laboratory animal (e.g., a mouse, a rat, and a sand rat), a pet animal (e.g., a hamster, a guinea pig, a dog, a cat, a horse, a squirrel, a rabbit, and a ferret), wild and zoo mammals (e.g., a monkey, a fox, a deer, and a buffalo), a fowl (e.g., a turkey, a duck, a chicken, a quail, and a goose), and a pet bird (e.g., a pigeon, a parrot, a myna bird, a Java sparrow, a parakeet, a Bengalese finch, and a canary bird); and fishes such as salmon, trout, and koi may be exemplified. Parasitic diseases mediated by parasites may be prevented or treated by controlling and expelling the parasites.
As the parasite to be controlled or expelled, the following may be exemplified.
Nematodes of the order Dioctophymatida
(2) Nematodes of the order Trichocephalida
(3) Nematodes of the order Rhabditida threadworms of the family Strongyloididae, for example, Strongyloides papillosus, Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, and Strongyloides ratti of Strongyloides spp.
(4) Nematodes of the order Strongylida hookworms of the family Ancylostomatidae, for example, Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, and Ancylostoma tubaeforme of Ancylostoma spp.; Uncinaria stenocephala of Uncinaria spp.; and Bunostomum phlebotomum and Bunostomum trigonocephalum of Bunostomum spp.
(5) Nematodes of the order Strongylida
(6) Nematodes of the order Strongylida
(7) Nematodes of the order Strongylida
(8) Nematodes of the order Oxyurida nematodes of the family Oxyuridae, for example, Enterobius anthropopitheci and Enterobius vermicularis of Enterobius spp.; Oxyuris equi of Oxyuris spp.; and Passalurus ambiguus of Passalurus spp.
(9) Nematodes of the order Ascaridida
(10) Nematodes of the order Spirurida
(11) Nematodes of the order Spirurida
The imidazo[1,2-a]pyridine compound of the present invention is additionally excellent in control effect on insect pests that have a stinger or venom and harm humans and animals, insect pests that mediate various pathogens or disease-causing microbes, or insect pests that cause discomfort to humans (toxic pests, hygienic pests, and obnoxious pests, etc.).
Specific examples thereof will be shown below.
Insect pests of the order Hymenoptera bees of the family Argidae, bees of the family Cynipidae, bees of the family Diprionidae, ants of the family Formicidae, bees of the family Mutillidae, and bees of the family Vespidae.
(2) Other insect pests Blattodea, termites, Araneae, centipedes, millipedes, crustacea, and Cimex lectularius.
Some pharmaceutical formulations of the pest control agent, the insecticide or acaracide, the ectoparasite control agent or the endoparasite control agent or expellant of the present invention will be shown. However, additives and addition ratios should not be limited by these examples and may be changed in wide ranges. The term “part” in the pharmaceutical formulations represents part by weight.
Hereinafter, the pharmaceutical formulations for agriculture or horticulture and for paddy rice will be shown.
40 parts of the imidazo[1,2-a]pyridine compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkyl naphthalenesulfonate are uniformly mixed and finely milled to obtain a wettable powder containing 40% of the active ingredient.
30 parts of the imidazo[1,2-a]pyridine compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.
5 parts of the imidazo[1,2-a]pyridine compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed, finely milled, and then granulated into a granular shape of 0.5 to 1.0 mm in diameter to obtain a granular formulation containing 5% of the active ingredient.
5 parts of the imidazo[1,2-a]pyridine compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are well milled and mixed, and after addition of water, the mixture is well kneaded, then granulated, and dried to obtain a granular formulation containing 5% of the active ingredient.
10 parts of the imidazo[1,2-a]pyridine compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 parts of xanthan gum, and 73.8 parts of water are mixed and wet-milled until the particle size becomes 3 microns or smaller to obtain a suspension containing 10% of the active ingredient.
Hereinafter, the pharmaceutical formulations of the ectoparasite control agent or the endoparasite control agent or expellant will be shown.
5 parts of the imidazo[1,2-a]pyridine compound of the present invention are dissolved in an organic solvent to obtain a solution. The solution is sprayed onto 94 parts of kaolin and 1 part of white carbon. Then, the solvent is evaporated under reduced pressure. This type of granules may be mixed with animal feed.
0.1 to 1 parts of the imidazo[1,2-a]pyridine compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed and then sterilized by filtration through a sterilizing filter.
5 parts of the imidazo[1,2-a]pyridine compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol are uniformly mixed to obtain a pore-on formulation.
10 to 15 parts of the imidazo[1,2-a]pyridine compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on formulation.
1 part of the imidazo[1,2-a]pyridine compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol are uniformly mixed to obtain a spray formulation.
Next, the present invention will be more specifically described with reference to Examples. However, the present invention is not limited by the following Examples by any means.
(Step 1) Synthesis of 2-bromo-3-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine
2-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine (1.98 g) was dissolved in N,N-dimethylformamide (15 ml). N- chlorosuccinimide (1.1 g) was added thereto, and the mixture was stirred at 50° C. for 1 hour. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.6 g of the title compound (yield: 71%).
1H-NMR of the obtained title compound will be shown below.
1H-NMR (400 MHz, CDCl3) δ: 8.41 (1H, s), 7.69 (1H, d), 7.43 (1H, dd).
(Step 2) Synthesis of 3-Chloro-2-(1-methyl-1H-imidazol-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine
1-Methyl-1H-imidazole (0.33 g) was dissolved in tetrahydrofuran (14 ml), and the reaction vessel was purged with nitrogen, followed by cooling to -70° C. A solution of 2.75 M n-butyllithium in n-hexane solution (1.5 ml) was added dropwise thereto, and the mixture was stirred at -70° C. for 30 minutes. A 1 M zinc chloride (II) tetrahydrofuran solution (8 ml) was added thereto, and the mixture was heated to room temperature, and stirred for 1 hour. Thereafter, a solution of 2-bromo-3-chloro-6-(trifluoromethyl)imidazo[1,2-a]pyridine (1.2 g) in toluene (27 ml) and tetrakis(triphenylphosphine)palladium (0) (0.16 g) were added, and the reaction vessel was purged with nitrogen, followed by stirring overnight under heating to reflux. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.70 g of the title compound (yield: 58%).
1H-NMR of the obtained title compound will be shown below.
1H-NMR (400 MHz, CDCl3) δ: 8.56-8.51 (1H, m), 7.72 (1H, d), 7.43 (1H, dd), 7.27-7.25 (1H, m), 7.02 (1H, d), 4.13 (3H, s) .
(Step 3) Synthesis of 3-(ethylthio)-2-(1-methyl-1H-imidazol-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine
3-Chloro-2-(1-methyl-1H-imidazol-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine (0.70 g) was dissolved in tetrahydrofuran (10 ml), and mixture was stirred at room temperature. 80% Ethylmercaptan sodium (1.2 g) was added thereto, and the mixture was stirred for 4 hours under heating to reflux. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.29 g of the title compound (yield: 38%).
1H-NMR of the obtained title compound will be shown below.
1H-NMR (400 MHz, CDCl3) δ: 8.95 (1H, s), 7.72 (1H, d), 7.44 (1H, dd), 7.25 (1H, d), 7.03 (1H, d), 4.05 (3H, s), 3.01 (2H, q), 1.16 (3H, t).
(Step 4) Synthesis of 2-(5-bromo-1-methyl-1H-imidazol-2-yl)-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine
3-(Ethylthio)-2-(1-methyl-1H-imidazol-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine (0.29 g) was dissolved in dichloromethane (10 ml), and the mixture was cooled to 0° C. N-bromosuccinimide (0.87 g) was added thereto, and the mixture was stirred at room temperature for 3 hours. The obtained solution was poured to water, followed by extraction with dichloromethane. The obtained organic layer was washed with a saturated solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was used for the next step without being purified.
(Step 5) Synthesis of 2-(5-bromo-1-methyl-1H-imidazol-2-yl)-3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine
The 2-(5-bromo-1-methyl-1H-imidazol-2-yl)-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine obtained in step 4 was dissolved in dichloromethane (10 ml), and the mixture was cooled to 0° C., and stirred. 70% m-Chloroperbenzoic acid (0.48 g) was added thereto, and the mixture was stirred overnight at room temperature. The obtained solution was poured to a mixed solution of a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium thiosulfate, followed by extraction with dichloromethane. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.35 g of the title compound (yield: 90%, two steps) .
1H-NMR of the obtained title compound will be shown below.
1H-NMR (400 MHz, CDCl3) δ: 9.62 (1H, s), 7.85 (1H, d), 7.67-7.62 (1H, m), 7.20 (1H, s), 4.02 (2H, q), 3.89 (3H, s), 1.40 (3H, t).
(Step 6) Synthesis of 3-(ethylsulfonyl)-2-(1-methyl-5-(4-(trifluoromethoxy)phenyl)-1H-imidazol-2-yl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine
2-(5-Bromo-1-methyl-1H-imidazol-2-yl)-3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine (0.10 g) and dioxane (4 ml) were added to a microwave synthesis reaction vessel. 4-Trifluoromethoxyphenylboronic acid (0.061 g), tetrakis(triphenylphosphine)palladium (0) (0.013 g), potassium carbonate (0.048 g) and water (0.5 ml) were added thereto, and the mixture was reacted at 120° C. for 1 hour using a microwave synthesis apparatus. The obtained solution was poured to water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.050 g of the title compound (yield: 42%).
1H-NMR of the obtained title compound will be shown below.
1H-NMR (400 MHz, CDCl3) δ: 9.65 (1H, s), 7.87 (1H, d), 7.65 (1H, dd), 7.53-7.47 (2H, m), 7.34 (2H, d), 7.28-7.25 (1H, m), 4.11 (2H, q), 3.86 (3H, s), 1.43 (3H, t).
Examples of the imidazo[1,2-a]pyridine compounds of the present invention produced in the same way as in Examples described above are shown in Table 1. The physical property data of the compounds is described in the columns of “physical properties”. Properties or melting points (m.p.) are described as physical property data.
Test Examples given below show that the imidazo[1,2-a]pyridine compound of the present invention is useful as an active ingredient for pest control agents and ectoparasite control agents. The term “part” is based on weight.
5 parts of the imidazo[1,2-a]pyridine compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (I) containing 5% of the active ingredient.
For a control, 98.5 parts of dimethylformamide and 1.5 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare emulsion (II).
An insecticidal rate was calculated according to the following expression:
The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were dipped in the dilution for 30 seconds. The resulting cabbage leaves were placed in a petri dish. Five second instar larvae of Plutella xylostella were released thereto. The petri dish was placed in a thermostat chamber having a temperature of 25° C. and a humidity of 60%. Life and death were determined after 3 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.
Compounds of compound Nos. a-1 to a-13, a-17 and a-19 to a-24 were tested for their efficacy on Plutella xylostella. All the compounds exhibited an insecticidal rate of 80% or more for Plutella xylostella.
The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm to prepare a test chemical. The test chemical was sprayed to Qing geng cai seedlings (at the seventh true leaf stage) planted in 10-cm pots. The Qing geng cai seedlings were dried in air and then placed in a plastic cup. Ten Phyllotreta striolata adults were released thereto. The plastic cup was stored in a thermostat chamber having a temperature of 25° C. and a humidity of 65%. Life and death were determined after 7 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.
Compounds of compound Nos. a-2, a-3, a-5 to a-7, a-10 to a-13, a-16, a-17, and a-19 to a-23 were tested for their efficacy on Phyllotreta striolata adults. All the compounds exhibited an insecticidal rate of 80% or more for Phyllotreta striolata adults.
Cucumber seeds were planted in 10-cm pots. Aphis gossypii female adults were released to the cucumbers 10 days after their germination. On the following day, the female adults were removed while the born first instar larvae were saved.
The emulsion (I) was diluted with water such that the concentration of the compound of the present invention was 125 ppm, and the dilution was sprayed to the cucumbers.
Thereafter, the cucumbers were stored in a thermostat chamber having a temperature of 25° C. and a humidity of 60% during the test period, life and death were determined after 5 days, and the insecticidal rate was calculated. The test was conducted in duplicate.
Compounds of compound Nos. a-3, a-5, a-7, a-11, a-13, a-16, a-17 and a-20 were tested for their efficacy on Aphis gossypii adults. All the compounds exhibited an insecticidal rate of 80% or more for Aphis gossypii adults.
The compound of the present invention was dissolved in isopropanol to prepare a chemical at 20 ppm. 100 µL of the chemical was applied to the bottom surface of the inside of a glass vial (φ330 mm), and the isopropanol was volatilized by air drying to form a thin film of the benzoimidazole compound of the present invention on the bottom surface.
Five adults (mixed males and females) of cat flea (Ctenocephalides felis) were released to a vial. The vial was lidded, and placed in a thermostat chamber at 25° C. Life and death of the cat flea were determined after 4 days from the release of the insects, and the insecticidal rate was calculated. The test was conducted in duplicate.
Compounds of compound Nos. a-3, a-5, a-9, a-13 and a-17 to a-20 were tested for their efficacy on cat flea adults. All the compounds exhibited an insecticidal rate of 80% or more for cat flea adults.
All the compounds selected at random from among the imidazo[1,2-a]pyridine compounds of the present invention exerted the effect as described above. It may therefore be understood that the imidazo[1,2-a]pyridine compound of the present invention, including unillustrated compounds, is a compound having an effect such as a pest control effect, particularly, a acaracidal or insecticidal effect. It may also be understood that the imidazo[1,2-a]pyridine compound of the present invention is a compound also having an effect on parasites harmful to humans and animals, such as ectoparasites.
| Number | Date | Country | Kind |
|---|---|---|---|
| 2020-161237 | Sep 2020 | JP | national |
| 2021-090020 | May 2021 | JP | national |
| Filing Document | Filing Date | Country | Kind |
|---|---|---|---|
| PCT/JP2021/034331 | 9/17/2021 | WO |
