JP2022171124A - Agrohorticultural agent containing novel N-cyanomethylimidazopyridine-2-carboxamide derivative as active ingredient - Google Patents

Abstract

To provide a compound that is useful as an active ingredient of an agrohorticultural agent, particularly an agrohorticultural pest control agent, such as agrohorticultural insecticide and agrohorticultural acaricide.SOLUTION: As an active ingredient, an N-cyanomethylimidazopyridine-2-carboxamide derivative represented by the following formula (1), an N-oxide thereof, or a salt thereof is used. In the formula, R1 is, for example, a C1-3 alkyl group, A1, A2, A3, A4 and A5 are each independently C-R2, and R2 is, for example, a C1-3 alkyl group or a C1-3 haloalkyl group.SELECTED DRAWING: None

Description

TECHNICAL FIELD The present invention relates to a novel N-cyanomethylimidazopyridine-2-carboxamide compound and a method of using the compound as an agricultural and horticultural agent, particularly as an agricultural and horticultural insecticide.

また、特許文献２には化合物Bを包含する化合物を開示する。しかしながら、特許文献２には、本発明の化合物が有するN-シアノメチル基に関してまったく開示をしていない。

一方、酸部分が芳香族環又は芳香族ヘテロ環であり、N-シアノメチル基を有するカルボキサミド誘導体として、下記化合物Cを包含する特許文献３が開示されている。しかしながら、特許文献３には殺菌剤としての開示はあるが、殺虫剤に関する記載は全く開示をしていない。

In the field of agriculture and horticulture, plant pest control agents have been developed and put into practical use for the purpose of controlling various pests. However, conventionally used agricultural and horticultural insecticides are not necessarily satisfactory in terms of insecticidal effect or residual effect. In addition, it cannot be said that the requirements such as the number of times of application and the reduction of the amount of applied drug are satisfied.
In addition, the emergence of various mites that have acquired resistance to conventionally used acaricides has become a problem.
There is a strong need for the development of a new insecticide that exhibits a sufficient control effect at a low dosage against various pests that have acquired resistance to conventional agricultural and horticultural insecticides, and that has little adverse effect on the environment. ing.
Various new insecticides and acaricides have been proposed to meet these demands, but they do not necessarily meet the above demands.
Compound A and Compound B below are disclosed as analogous N,N-disubstituted imidazopyridine-2-carboxamide derivatives of the present invention.
Patent document 1 discloses compounds including compound A. However, Patent Document 1 does not disclose any N-cyanomethyl groups possessed by the compounds of the present invention.

Further, Patent Document 2 discloses a compound including compound B. However, Patent Document 2 does not disclose any N-cyanomethyl groups possessed by the compounds of the present invention.

On the other hand, Patent Document 3, which includes the following compound C, discloses a carboxamide derivative having an N-cyanomethyl group in which the acid moiety is an aromatic ring or an aromatic heterocyclic ring. However, although Patent Document 3 discloses that it is a fungicide, it does not disclose any description of an insecticide.

Japanese Patent Application Laid-Open No. 2018-024660 WO 2020/251013 Japanese Patent Application Laid-Open No. 56-161361

The purpose of the present invention is to provide a new substance useful for controlling various pests in the agricultural and horticultural field. To provide a highly safe substance that is effective at a low dosage and has reduced environmental problems such as residual toxicity and environmental pollution.

[式中、
R¹は、Ｃ_1-6アルキル基又はＣ_1-6ハロアルキル基を示し、
A₁、A₂、A₃、A₄ 及び A₅ は、それぞれ独立してC-R²を示し、
R²は、同一又は異なっても良く、水素原子、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルコキシ基、Ｃ_3-6アルケニルオキシ基、Ｃ_3-6アルキニルオキシ基、Ｃ_1-6ハロアルコキシ基、Ｃ_3-6ハロアルケニルオキシ基、Ｃ_3-6ハロアルキニルオキシ基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6ハロアルキルスルホニル基、ニトロ基、又はシアノ基を示し、
R³は、水素原子、ハロゲン原子、Ｃ_1-6アルキル基、Ｃ_1-6ハロアルキル基、Ｃ_3-8シクロアルキル基、Ｃ_1-6アルキルチオ基、Ｃ_1-6アルキルスルフィニル基、Ｃ_1-6アルキルスルホニル基、Ｃ_1-6ハロアルキルチオ基、Ｃ_1-6ハロアルキルスルフィニル基、Ｃ_1-6ハロアルキルスルホニル基、ニトロ基、又はシアノ基を示し、
nは、0から2の整数を示す。]
で表されるN-シアノメチルイミダゾピリジン-2-カルボキサミド誘導体、そのＮ－オキシド又はその塩、並びにその使用及びその製造方法に関するものである。 Accordingly, the present inventors have made intensive studies to solve the above problems, and as a result, have found an N-cyanomethylimidazopyridine-2-carboxamide derivative represented by the following formula (I), which is a novel compound not described in the literature. , found that it is useful as an agricultural and horticultural agent, particularly an agricultural and horticultural insecticide, that can meet the above-mentioned needs, and have completed the present invention.
That is, the present invention provides the following formula (1),

[In the formula,
R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group,
A ₁ , A ₂ , A ₃ , A ₄ and A ₅ each independently represent CR ² ,
R ² may be the same or different, hydrogen atom, halogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy group, _C3-6 alkynyloxy group, _{C1-6 haloalkoxy} group, _C3-6 haloalkenyloxy group, C3-6 haloalkynyloxy group, _C1-6 alkylthio group, _C1-6 alkyl a sulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 haloalkylthio group, a C _1-6 haloalkylsulfinyl group, a C _1-6 haloalkylsulfonyl group, a nitro group, or a cyano group,
R ³ is a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _{1- 6} alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, nitro group or cyano group,
n is an integer from 0 to 2; ]
N-cyanomethylimidazopyridine-2-carboxamide derivative represented by, its N-oxide or its salt, its use and its production method.

The compounds of the present invention exhibit excellent effects as agricultural and horticultural agents, particularly as agricultural and horticultural insecticides. In addition, the compounds of the present invention are also effective against pests parasitic on pets such as dogs and cats, or livestock such as cattle and sheep.

In the definition of the compound of the present invention represented by the above formula (1), "halogen atom" means chlorine atom, bromine atom, iodine atom or fluorine atom, and "C _1-6 alkyl group" means, for example, , methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, i-butyl group, s-butyl group, t-butyl group, n-pentyl group, isopentyl group, neopentyl group, tert- A linear or branched alkyl group having 1 to 6, preferably 1 to 3 carbon atoms such as a pentyl group, n-hexyl group, isohexyl group, etc. "C _1-6 haloalkyl" represents a straight or branched chain alkyl group having 1 to 6 carbon atoms as defined above substituted by one or more, preferably 1 to 3, halogen atoms which may be the same or different, and "C " _3-8 cycloalkyl" refers to a cyclic cycloalkyl group having 3 to 8, preferably 3 to 6 carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclooctyl, and the like.

Specific examples of the "C _1-6 haloalkyl group" include, for example, fluoromethyl group, chloromethyl group, difluoromethyl group, trifluoromethyl group, chlorodifluoromethyl group, bromodifluoromethyl group, dichlorofluoromethyl group, 1- fluoroethyl group, 2-fluoroethyl group, 2-chloroethyl group, 2-bromoethyl group, 2-iodoethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group , 1-fluoroisopropyl group, 3-fluoropropyl group, 3-chloropropyl group, 3-bromopropyl group, heptafluoropropyl group, 4-fluorobutyl group, 4-chlorobutyl, nonafluorobutyl group, 5,5,5 - 1 to 13 groups, preferably 1, such as a trifluoropentyl group, 5-chloropentyl group, undecafluoropentyl group, 6,6,6-trifluorohexyl group, 6-chlorohexyl group, and tridecafluorohexyl group Examples include straight or branched chain alkyl groups of 1 to 6 carbon atoms as defined above, substituted with up to 9 halogen atoms.
Examples of the "C _1-6 alkoxy group" include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, n- Linear or branched alkoxy groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms, such as hexyloxy groups.
Examples of the "C _1-6 haloalkoxy group" include, for example, a fluoromethoxy group, a dichloromethoxy group, a trichloromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, a chlorodifluoromethoxy group, a bromodifluoromethoxy group, a dichlorofluoromethoxy group, 1-fluoroethoxy group, 2-fluoroethoxy group, 2-chloroethoxy group, 2-bromoethoxy group, 2-iodoethoxy group, 2,2,2-trifluoroethoxy group, 2,2,2-trichloroethoxy group , pentafluoroethoxy group, 1-fluoroisopropoxy group, 3-fluoropropoxy group, 3-chloropropoxy group, 3-bromopropoxy group, 4-fluorobutoxy group, 4-chlorobutoxy group, etc., preferably 1 to 9 and straight or branched chain alkoxy groups having 1 to 6 carbon atoms as defined above substituted with 1 halogen atom.

Examples of the "C _3-6 alkenyloxy group" include allyloxy, isopropenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-pentenyloxy, 3- pentenyloxy group, 4-pentenyloxy group, 1,1-dimethyl-2-propenyloxy group, 1-ethyl-2-propenyloxy group, 1-methyl-2-butenyloxy group, 1-methyl-3-butenyloxy group, Any position of 2-hexenyloxy group, 3-hexenyloxy group, 4-hexenyloxy group, 5-hexenyloxy group, 1,1-dimethyl-2-butenyloxy group, 1,1-dimethyl-3-butenyloxy group, etc. A linear or branched alkenyloxy group having 3 to 6 carbon atoms, preferably 3 to 5 carbon atoms and having at least one double bond in .
The "C _3-6 haloalkenyloxy group" includes, for example, 3-chloro-2-propenyloxy group, 3,3-difluoro-2-allyloxy group, 3,3-dichloro-2-allyloxy group, 4,4 , 4-trifluoro-2-butenyloxy group, 4,4,4-trifluoro-3-butenyloxy group, 5-chloro-3-pentenyloxy group, 6-fluoro-2-hexenyloxy group at any position linear or branched alkenyloxy groups having 3 to 6 carbon atoms as defined above having at least one double bond and having 1 to 13, preferably 1 to 7 halogen atoms Substituted alkenyloxy groups are included.

The "C _3-6 alkynyloxy group" includes, for example, 2-propynyloxy group, 1-methyl-2-propynyloxy group, 1,1-dimethyl-2-propynyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3-pentynyloxy group, 4-pentynyloxy group, 1-methyl-2-butynyloxy group, 1-methyl-3- Any butynyloxy group, 1,1-dimethyl-2-butynyloxy group, 1,1-dimethyl-3-butynyloxy group, 1-methyl-3-pentynyloxy group, 1-methyl-4-pentynyloxy group, etc. A linear or branched alkynyloxy group having 3 to 6 carbon atoms, preferably 3 to 5 carbon atoms, having at least one triple bond at a position.
The "C _3-6 haloalkynyloxy group" includes 4,4,4-trifluoro-2-butynyloxy group, 5,5,5-trifluoro-3-pentynyloxy group, 1-methyl-3,3 ,3-trifluoro-2-butynyloxy group, 1-methyl-5,5,5-trifluoro-2-pentynyloxy group, etc., having at least one triple bond at any position and having 3 to 6 carbon atoms. Chain or branched alkynyloxy groups, as defined above, substituted with 1 to 9, preferably 1 to 6, halogen atoms are included.

The "C _1-6 alkylthio group" includes, for example, methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, n- A linear or branched alkylthio group having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as hexylthio group can be mentioned.
Examples of the "C _1-6 alkylsulfinyl group" include methylsulfinyl group, ethylsulfinyl group, n-propylsulfinyl group, isopropylsulfinyl group, n-butylsulfinyl group, sec-butylsulfinyl group, tert-butylsulfinyl group, Linear or branched alkylsulfinyl groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as n-pentylsulfinyl group and n-hexylsulfinyl group.
Examples of the "C _1-6 alkylsulfonyl group" include methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, Linear or branched alkylsulfonyl groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms such as n-pentylsulfonyl group and n-hexylsulfonyl group.
The "C _1-6 haloalkylthio group" includes, for example, a difluoromethylthio group, a trifluoromethylthio group, a monochloromethylthio group, a dichloromethylthio group, a trichloromethylthio group, a monobromomethylthio group, a dibromomethylthio group, a tribromomethylthio group, 1 -fluoroethylthio group, 2-fluoroethylthio group, 2,2-difluoroethylthio group, 2,2,2-trifluoroethylthio group, 2-chloro-2,2-difluoroethylthio group, 1-chloro ethylthio group, 2-chloroethylthio group, 2,2,-dichloroethylthio group, 2,2,2-trichloroethylthio group, 2-bromoethylthio group, 2,2-dibromoethylthio group, 2, 2,2-tribromoethylthio group, pentafluoroethylthio group, 3-fluoropropylthio group, 3-chloropropylthio group, 3-bromopropylthio group, 1,3-difluoro-2-propylthio group, 3, 3,3-trifluoropropylthio group, 1,3-dichloro-2-propylthio group, 1,1,1-trifluoro-2-propylthio group, 1-chloro-3-fluoro-2-propylthio group, 1, 1,1,3,3,3-hexafluoro-2-propylthio group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylthio group, 2,2,3,3, 3-pentafluoropropylthio group, heptafluoroisopropylthio group, heptafluoro-n-propylthio group, 4-fluorobutylthio group, 4,4,4-trifluorobutylthio group, nonafluoro-n-butylthio group, nonafluoro- linear or branched alkylthio groups having 1 to 6 carbon atoms, preferably 1 to 3 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms such as 2-butylthio group; be done.

The "C _1-6 haloalkylsulfinyl group" includes a difluoromethylsulfinyl group, a trifluoromethylsulfinyl group, a dichloromethylsulfinyl group, a trichloromethylsulfinyl group, a monobromomethylsulfinyl group, a dibromomethylsulfinyl group, a tribromomethylsulfinyl group, 1-fluoroethylsulfinyl group, 2-fluoroethylsulfinyl group, 2,2-difluoroethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group, 2-chloro-2,2-difluoroethylsulfinyl group, 1- chloroethylsulfinyl group, 2-chloroethylsulfinyl group, 2,2,-dichloroethylsulfinyl group, 2,2,2-trichloroethylsulfinyl group, 2-bromoethylsulfinyl group, 2,2-dibromoethylsulfinyl group, 2 ,2,2-tribromoethylsulfinyl group, pentafluoroethylsulfinyl group, 3-fluoropropylsulfinyl group, 3-chloropropylsulfinyl group, 3-bromopropylsulfinyl group, 1,3-difluoro-2-propylsulfinyl group, 3,3,3-trifluoropropylsulfinyl group, 1,3-dichloro-2-propylsulfinyl group, 1,1,1-trifluoro-2-propylsulfinyl group, 1-chloro-3-fluoro-2-propyl sulfinyl group, 1,1,1,3,3,3-hexafluoro-2-propylsulfinyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfinyl group, 2 ,2,3,3,3-pentafluoropropylsulfinyl group, heptafluoroisopropylsulfinyl group, heptafluoro-n-propylsulfinyl group, 4-fluorobutylsulfinyl group, 4,4,4-trifluorobutylsulfinyl group, nonafluoro -n-butylsulfinyl group, nonafluoro-2-butylsulfinyl group, etc. 1 to 13, preferably 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms, preferably 1 to 3 straight A chain or branched alkylsulfinyl group may be mentioned.
The "C _1-6 haloalkylsulfonyl group" includes a difluoromethylsulfonyl group, a trifluoromethylsulfonyl group, a dichloromethylsulfonyl group, a trichloromethylsulfonyl group, a monobromomethylsulfonyl group, a dibromomethylsulfonyl group, and a tribromomethylsulfonyl group. , 1-fluoroethylsulfonyl group, 2-fluoroethylsulfonyl group, 2,2-difluoroethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group, 2-chloro-2,2-difluoroethylsulfonyl group, 1 -chloroethylsulfonyl group, 2-chloroethylsulfonyl group, 2,2,-dichloroethylsulfonyl group, 2,2,2-trichloroethylsulfonyl group, 2-bromoethylsulfonyl group, 2,2-dibromoethylsulfonyl group, 2,2,2-tribromoethylsulfonyl group, pentafluoroethylsulfonyl group, 3-fluoropropylsulfonyl group, 3-chloropropylsulfonyl group, 3-bromopropylsulfonyl group, 1,3-difluoro-2-propylsulfonyl group , 3,3,3-trifluoropropylsulfonyl group, 1,3-dichloro-2-propylsulfonyl group, 1,1,1-trifluoro-2-propylsulfonyl group, 1-chloro-3-fluoro-2- propylsulfonyl group, 1,1,1,3,3,3-hexafluoro-2-propylsulfonyl group, 1,1,1,3,3,3-hexafluoro-2-chloro-2-propylsulfonyl group, 2,2,3,3,3-pentafluoropropylsulfonyl group, heptafluoroisopropylsulfonyl group, heptafluoro-n-propylsulfonyl group, 4-fluorobutylsulfonyl group, 4,4,4-trifluorobutylsulfonyl group, 1 to 6, preferably 1 to 3 carbon atoms substituted with 1 to 13, preferably 1 to 9 halogen atoms such as nonafluoro-n-butylsulfonyl group and nonafluoro-2-butylsulfonyl group A linear or branched alkylsulfonyl group may be mentioned.

Examples of the salt of the N-cyanomethylimidazopyridine-2-carboxamide derivative represented by the formula (1) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate; Organic acid salts such as acid salts, maleates, oxalates, methanesulfonates, benzenesulfonates, and p-toluenesulfonates can be exemplified.
The N-cyanomethylimidazopyridine-2-carboxamide derivative represented by the formula (1) of the present invention may contain one or more asymmetric centers in its structural formula, and has two or more optical There may be isomers and diastereomers, and the present invention includes all optical isomers and mixtures containing them in any ratio. Further, the N-cyanomethylimidazopyridine-2-carboxamide derivative represented by the formula (1) of the present invention has two geometric isomers derived from a carbon-carbon double bond in its structure. As the case may be, the present invention also includes all geometric isomers and mixtures thereof in any proportion.

Among the compounds of the present invention, compounds in which R ² represents a C _1-3 alkyl group or C _1-3 haloalkyl group are preferred, and compounds in which R ² represents a C _1-3 haloalkyl group are particularly preferred.
Among the compounds of the present invention, compounds in which R ¹ represents a C _1-3 alkyl group or a C _1-3 haloalkyl group are preferred, and compounds in which R 1 represents a C _1-3 alkyl group are particularly preferred.
Among the compounds of the present invention, compounds in which R ³ and R ⁴ are C _1-3 haloalkyl groups are preferred, and compounds in which C _1-3 haloalkyl groups are particularly preferred.

［式中、R¹、R²、R³、A₁、A₂、A₃、A₄、A₅及びnは、前記で定義した通りである。］
反応式１に示す方法においては、前記式（１）で表されるN-シアノメチルイミダゾピリジン-2-カルボキサミド誘導体(1-1)及び(1-2)は、前記式（1-0）で表されるN-シアノメチルイミダゾピリジン-2-カルボキサミド誘導体の酸化反応により製造される。 Representative methods for producing the novel N-cyanomethylimidazopyridine-2-carboxamide derivative represented by formula (1) of the present invention are shown below, but the present invention is not limited thereto.
Reaction formula 1

[wherein R ¹ , R ² , R ³ , A ₁ , A ₂ , A ₃ , A ₄ , A ₅ and n are as defined above. ]
In the method shown in Reaction Scheme 1, the N-cyanomethylimidazopyridine-2-carboxamide derivatives (1-1) and (1-2) represented by the above formula (1) are represented by the above formula (1-0). It is produced by an oxidation reaction of the represented N-cyanomethylimidazopyridine-2-carboxamide derivative.

As the solvent used in the oxidation reaction of the compound of formula (1-0), a wide range of solvents inert to the reaction can be used. For example, aliphatic or alicyclic hydrocarbon solvents such as hexane, cyclohexane, and heptane; aromatic hydrocarbon solvents such as benzene, chlorobenzene, toluene, and xylene; and halogenated solvents such as methylene chloride, 1,2-dichloroethane, and chloroform. Hydrocarbon solvents, alcohol solvents such as methanol and ethanol, ester solvents such as methyl acetate and ethyl acetate, ketone solvents such as acetone and methyl ethyl ketone, amide solvents such as N,N-dimethylformamide, acetonitrile, and propio. Examples include nitrile solvents such as nitrile, aprotic polar solvents such as N-methylpyrrolidone and N,N'-dimethylimidazolinone, and acetic acid. One of these solvents can be used alone, or two or more of them can be used in combination, if necessary.
Examples of the oxidizing agent used in the oxidation reaction of formula (1-0) include m-chloroperbenzoic acid, sodium periodate, hydrogen peroxide and the like.
Such an oxidizing agent is generally used in an amount of 1 to 3 equivalents, preferably 1 to 2.5 equivalents, relative to the N-cyanomethylimidazopyridine-2-carboxamide derivative represented by (1-0). can be used.
The reaction can usually be carried out at -78°C to the boiling point of the solvent used, preferably at 0°C to room temperature.
Although the reaction time varies depending on the reaction temperature and the like, it cannot be generalized, but the reaction is usually completed in about 0.5 to 24 hours.
The target compound obtained in each of the above reactions can be easily isolated from the reaction mixture by commonly used isolation means such as organic solvent extraction, chromatography, recrystallization, distillation, and the like. , can be further purified by conventional purification means.

［式中、R¹、R²、R³、A₁、A₂、A₃、A₄、A₅及びnは、前記で定義した通りであり、Yは、塩素原子、臭素原子、ヨウ素原子、メタンスルホニルオキシ基又はトリフルオロメタンスルホニルオキシ基を表す］
反応式２に示す方法においては、例えば特許文献３などに記載された方法に準じて、前記式（1-3）で表されるイミダゾピリジン-2-カルボキサミド誘導体とYCH₂CNで表されるアセトニトリル誘導体とを塩基存在下溶媒中で反応させることにより前記式（1-0）が製造される。 Reaction formula 2

[Wherein, R ¹ , R ² , R ³ , A ₁ , A ₂ , A ₃ , A ₄ , A ₅ and n are as defined above, Y is a chlorine atom, a bromine atom, an iodine atom , represents a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group]
In the method shown in Reaction Scheme 2, the imidazopyridine-2-carboxamide derivative represented by the above formula (1-3) and the acetonitrile represented by YCH ₂ CN are reacted, for example, according to the method described in Patent Document 3. The above formula (1-0) is produced by reacting the compound with the derivative in the presence of a base in a solvent.

As the solvent used in the reaction shown in Reaction Scheme 2, a wide variety of known solvents can be used as long as they are inert to the reaction. For example, ether solvents such as diethyl ether, tetrahydrofuran, and 1,4-dioxane; amide solvents such as N,N-dimethylformamide; solvents such as dimethylsulfoxide, N-methylpyrrolidone, and N,N'-dimethylimidazolinone; can be mentioned. One of these solvents can be used alone, or two or more of them can be used in combination, if necessary.
As the base used in the reaction, known inorganic bases and organic bases can be used. For example, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydroxides such as sodium hydroxide, potassium hydroxide and lithium hydroxide, potassium t- Alkali metal alkoxides such as butoxide, triethylamine, tributylamine, diisopropylethylamine, N-methylmorpholine, pyridine, 4-(N,N-dimethylamino)pyridine, N,N-dimethylaniline, N,N-diethylaniline, 1 ,5-diazabicyclo[4.3.0]non-5-ene, 1,4-diazabicyclo[2.2.2]octane (DABCO), 1,8-diazabicyclo[5.4.0]-7-undecene Examples include organic bases such as (DBU). Preferred are alkali metal hydrides, alkali metal carbonates, and alkali metal hydroxides, and more preferred are sodium hydride and potassium carbonate.

The amount of the base used is generally 1 to 3 equivalents, preferably 1 to 2.5 equivalents, per 1 mol of the compound of formula (1-3).
The reaction is preferably carried out at 0°C to the boiling point of the solvent used, more preferably 0°C to 80°C.
The reaction is usually completed within about 0.5 to 24 hours.
After completion of the reaction, the target product can be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography, or the like, if necessary. It is also possible to subject the target product to the next reaction step without isolating it from the reaction system.

The imidazopyridine-2-carboxamide derivative represented by the general formula (1-3) used in this reaction is synthesized, for example, according to the method described in JP-A-2018-24660 (Patent Document 1). be able to.
Representative compounds of the N-cyanomethylimidazopyridine-2-carboxamide derivative represented by formula (1) are shown in Table 1, but the scope of the present invention is not limited to these compounds.
The physical properties in the table indicate properties and melting points (° C.), "Me" indicates a methyl group, and "Et" indicates an ethyl group.

表１

General formula (1)

Table 1

The compounds of the present invention can be used for the prevention or control of harmful organisms in agriculture, indoors or forests, on livestock or in a variety of situations such as hygiene. Specific usage scenes, target pests, and usage methods are shown below, but the scope of the present invention is not limited to these aspects.
The compound of the present invention represented by the formula (1) is used in crops such as food crops (rice, barley, wheat, rye, wheat such as oats, corn, potatoes, sweet potatoes, taro, soybeans, adzuki beans, broad beans, beans, kidney beans, peanuts, etc.), vegetables (cabbage, Chinese cabbage, radish, turnip, broccoli, cauliflower, cruciferous crops such as Komatsuna, pumpkin, cucumber, watermelon, melon, melon, etc.) , eggplants, tomatoes, green peppers, peppers, okra, spinach, lettuce, lotus root, carrots, burdock, garlic, onions, green onions, etc.), mushrooms (shiitake mushrooms, mushrooms, etc.), fruit trees and fruits (apples, citrus fruits) , pears, grapes, peaches, plums, cherries, walnuts, chestnuts, almonds, bananas, strawberries, etc.), fragrances and other ornamental crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), special crops (tobacco, tea, sugar beets, sugar cane, hops, cotton, hemp, olives, rubber, coffee, etc.), grass and feed crops (timothy, clover, alfalfa, corn, sorghum, orchard grass, gramineous grass, leguminous grass, etc.), Lawns (Korai turf, bentgrass, etc.), forest trees (Todomatsu, Ezo spruce, pine, Hiba, cedar, cypress, etc.), ornamental plants (Chrysanthemum, roses, carnations, orchids and other herbs and flowers, ginkgo, cherry blossoms) pests such as arthropods, molluscs, and nematodes, as well as fungi and bacteria such as fungi, dysmycota, bacteria, and actinomycetes can also be used to control Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example Helicoverpa armigera of the family Noctuidae, Heliothis spp., Agrotis segetum, Autographa nigrisigna, Trichoplusia ni ), Mamestra brassicae, Spodoptera exigua, Spodoptera litura, etc., Plutella xylostella, etc. of the sedge family, Adoxophyes orana fasciata, Adoxophyes honmai), Archips fuscocupreanus, Homona magnanima, Caloptilia theivora, Grapholita molesta, Eumeta minuscula, etc., Lyonetia prunifoliella malinella), Lyonetia clerkella, etc., Phyllocnistis citrella, etc., Phyllonorycter ringoniella, etc., Acrolepiopsis sapporensis, etc., Synantedin hector, etc. , Stathmopoda masinissa, etc., Pectinophora gossypiella, etc., Carposina niponensis, etc., Cossus jezoensis, etc., Nemapogon granella, etc. , Monema flavecens, Parasa lepida, Scopelodes con tracus), etc., Chilo suppressalis of the Tsutoga family, Scirpophaga incertulas, Cnaphalocrocis medialis, Hellulla undalis, Conogethes punctiferlis, Diaphania indica, Parapedia teterrella, etc., Locastra muscosalis, etc., Parnara guttata, etc., Papilio xuthus, etc., Papilio xuthus, etc., Pieris rapae crucivora, etc. Lampides boeticus of the family Lycaenidae, Ascotis selenaria of the Geometridae family, Agrius convolvuli of the family Phalera flavescens, etc., Malacosoma of the family Malacosoma neustrium testaceum), etc., Saturnia japonica, etc., Euproctis pseudoconspersa, Orgyia thyellina, Telochurus recens approximans, etc., Spilosoma imparilis, Adults, larvae and eggs such as Hyphantria cunea, Grapeberry moss (Endopiza viteana), Codling moth (Laspeyresia pomonella);

Coleoptera, for example, Anomala cuprea, Popillia japonica, Oxycetonia jucunda, Anomala geniculata, etc. of Scarabaeidae, Agrilus auriventris of Buprestidae, etc. , Melanotus fortnumi, etc., Epilachna vigintioctopunctata, Epilachna vigintioctopunctata, Anoplophora malasiaca, Xylotrechus pyrrhoderus, etc. Aulacophora femoralis), Rootworm species (Diabrotica spp.), Phyllotreta striolata, Cassida nebulosa, Phaedon brassicae, Oulema oryzae, Mexican beetle (Epilachna varivestis), Colorado potato beetle (Leptinotarsa decemlineata) ), etc., Rhynchites heroes, etc., Cylas formicarius, etc., Curculio sikkimensis, Lissorhoptrus oryzophilus, Boll weevil (Anthonomus gradis grandis), Sphenophrus venatus vestitus, etc., adults, larvae and eggs such as Epuraea domina of the family Pelargonium;

Heteroptera of the order Hemiptera, such as Eurydema rugosum, Eysarcoris lewisi, Eysarcoris parvus, Nezara viridula, Germania Stink bug (Plautia stali), brown stink bug (Halymorpha mista), etc., pear stink bug (Urochela luteovoria), etc. , Cletus punctiger, etc., Leptocorisa chinensis, etc., Dysdeercus cingulatus, etc., Stephanitis nashi, Stephanitis pyrioides etc., adults, larvae, and eggs such as Apolygus spinolai (Apolygus spinolai), Stenotus rubrovittalus, Trigonotylus coelestialium (Trigonotylus coelestialium), etc.

Homoptera of the order Hemiptera, such as Platypleura kaempferi of the family Cicada, Arboridia apicalis of the family Leafhopper, Empoasca onukii, Nephotettix cincticeps , Nephotettix virescens, etc., Laodelphax striatellus, Nilaparvata lugens, Sogatella furcifera, etc., Geisha distinctissima pyrus, etc., Psyllasisuga, Psyllasisuga Citrus whitefly (Diaphorina citri), etc., Aleurocanthus spiniferus of the family Whitefly, various biotypes of silver leaf whitefly (Bemisia argentifolii), tobacco whitefly (Bemisia tabaci), orange whitefly (Dialeurodes citri), whitefly (Trialeurodes vaporariorum), etc. Aphis citricola, Aphis craccivora, Aphis gossypii, Aulacorthum solani, Brevicoryne brassicae ), Toxoptera aurantii, Toxoptera citricidus, Aulacorthum magnoliae, Schizaphis piricola, Nippolachnus piri, Lipaphis erysimi, Peach aphid (Hyalopterus pruni), Chrysanthemum aphid (Pleotrichophorus chrysanthemi), Macrosiphoniella sanborni, Megoura crassicauda, Sitobion ibarae, Macrosiphum euphorbiae, Myzus varians, Myzus persicae), Rhopalosiphum rufiabdominalis, Rhopalosiphum padi, Sitobion akebiae, Eriosoma lanigerum, etc. Pseudococcus comstocki, Phenacoccus viburnae, Phenacoccus kraunhiae, etc., Ceroplastes ceriferus, Ceroplastes rubens, etc. Adults, larvae and eggs such as Aonidiella aurantii, Comstockaspis perniciosa, Pseudaulacaspis pentagoa, and Unaspis yanonensis;

Thysanoptera, for example Scirtothrips dorsalis of the family Thrips, Thrips palmi, Thrips tabaci, Thrips setosus, Frankliniella intonsa, citrus Adults, larvae and eggs of Frankliniella occidentalis, Heliothrips haemorrhoidalis, etc., Ponticulothrips diospyrosi, Haplothrips aculeatus, etc. of the family Thrips family;

Hymenoptera, for example, Athalia rosae ruficornis, Arge pagana, etc. of the family Athalia rosae ruficornis, Arge mali, etc. Adults and larvae of Megachile nipponica nipponica, Formica japonica, Camponotus kiusiuensis, Lasius fuliginosus, Solenopsis richteri, S. invicta, S. geminata, etc. and eggs;
Diptera, for example, Asphondylia yushimai of the family Asphondylia, Rhacochlaena japonica of the family Tephritidae, Bactrocera cucurbitae, etc., Hydrellia griseola of the family Drosophila, etc. Drosophila suzukii, etc., Liriomyza trifolii, Liriomyza sativae, Chromatomyia horticola, Agromyza oryzae, Liriomyza bryoniae, etc. Adults, larvae and eggs such as Delia platura and Delia antiqua;

Orthoptera, for example Locusta migratoria of the Locustidae family, Ruspolia lineosa of the katydid family, Teleogryllus emma of the cricket family, Truljalia hibinonis, etc., Gryllotalpa orientalis of the family Mothidae ), adults, larvae and eggs such as Oxya yezoensis of the locust family;
Adults, larvae and eggs of the order Isoptera, for example Odontotermes formosanus of the family Termites;
Adults, larvae and eggs of the order Dermaptera, such as Labidura riparia of the family Dermaptera;

Adults, larvae and eggs of the order Collembola of the phylum Arthropod Insecta, such as Sminthurus viridis of the family Sminthurus viridis, and Onychiurus matsumotoi of the family Shirotobimidae; Adults, larvae and eggs of the class Isopada, such as Armadillidium vulgare of the family Armadillidium vulgare;
Arachnids of the phylum Arachnid (Acari), such as Polyphagotarsonemus latus and Phytonemus pallidus of the family Pyropodidae, etc., Penthaleus major of the family of Cutworms, etc., and Brevipalpus of the family Acaridae lewisi), Brevipalpus phoenicis, etc., Panonychus citri, Panonychus ulmi, Tetranychus urticae, Tetranychus kanzawai, Amphitetranychus viennensis, Totomatsuno spider mite ( Oligonychus ununguis, Bryobia eharai, Eotetranychus kankitus, Bryobia praetiosa, etc., Aculus Schlechtendali, Aculops pelekassi, Phyllocoptruta citri ), Eriophyes chibaensis, Aceria tulipae, Colomerus vitis, Aculus fockeui, Calacarus carinatus, etc. Tyrophagus putrescentiae, Rhizoglyphus robini), etc., adults, larvae and eggs;

Architaenioglossa of the phylum Gastropoda Mollusca, for example, Pomacea canaliculata of the family Snail, etc., Plumonata, for example, Achatina fulica of the family Achatina fulica, of the family Slug Slugs (Meghimatium bilineatum), Milax gagates of the family Slugidae, Chakoura slugs of the family Slug (Lehmannina valentiana), Acusta despecta sieboldiana of the family Acusta despecta sieboldiana, etc.;
Tylenchida of the phylum Nematoda Phantomia, for example, Ditylenchus destructor of the family Anguinidae, Tylenchorhynchus claytoni of the family Tylenchorhynchus, etc., Platylenchus penetrans ), Pratylenchus coffeae, etc., Helicotylenchus dihystera, etc. of the family Hoprolymus, Globodera rostochiensis, etc. of the family Globodera rostochiensis, Meloidogyne incognita of the family Meloidogyne, etc. Nematodes (Criconema jaejuense), etc., Strawberry Nematodes (Nothotylenchus acris) of the family Anguinaceae, etc., Strawberry Nematodes (Aphelecchoides fragarriae) of the family Aphelenkoides, etc.; ), Trichodorus sp., etc.;
Fungi and bacteria such as Eumycota, Myxomycota, Bacteriomycota, and Actinomycota.

Specific diseases to which the compound of the present invention represented by the formula (1) can be applied include rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), and sheath blight (Rhizoctonia solani). ), Pantoea ananatis, Acidovorax avene subsp. avenae, Pseudomonas fuscovaginae, Xanthomonas oryzae pv. oryzae, Burkholderia plantarii, etc. ; Powdery mildew of wheat (Erysiphe graminis), Fusarium head blight (Gibberella zeae), Fusarium rust (Puccinia striiformis, P.graminis, P. recondita, P. hordei), Snow rot (Typhula sp. , Micronectriella nivalis) , Ustilago tritici, U. nuda, Tilletia caries, Pseudocercosporella herpotrichoides, Rhynchosporium secalis, Septoria tritici, Leptosphaeria nodorum ), Pyrenophora teres, Helminthosporium zonatum Ikata, Pseudomonas syringae pv. disease (Penicillium digitatum, P. italicum), brown rot (Phytophthora citrophthora, P. nicotianae), scab (Phyllosticta citricarpa), etc.; (Podosphaera leucotricha), leaf spot (Alternaria mali), scab (Venturia inaequa) lis), Mycospherella pomi, Colletotrichum acutatum, Botryosphaeria berengeriana, Gymnosporangium yamadae, Monilinia fructicola, etc.; V. pirina), Alternaria kikuchiana, Gymnosporangium haraeanum, Monilinia fructigena, etc; Phomopsis sp. ), Brenneria nigrifluens, etc.; Elsinoe ampelina, Colletotrichum acutatum,

Powdery mildew (Uncinula necator), rust (Phakopsora ampelopsidis), blacklot (Guignardia bidwellii), downy mildew (Plasmopara viticola), ash star (Monilinia fructigena), scab (Cladosporium viticolum), gray mold ( Botrytis cinerea), Agrobacterium vitis, etc.; Sphaerotheca fuliginea, Oidiopsis taurica, Didymella bryoniae, Fusarium oxysporum, Pseudoperonospora cubensis, Phytophthora sp., Pythium sp. etc.; Pseudomonas syringae pv. lochrymans, Pseudomonas viridiflava, Xanthomonas campestris pv. cucurbitae, etc.; Xanthomonas campestris pv. cucurbitae of melons , hair root disease (Agrobacterium rhizogens), cancer (Streptomyces sp.), etc.; fruit stain bacterial disease of watermelon (Acidovorax avenae pv. citrulli), etc.; Alternaria solani, Cladosporium fulvum, Phytophthora infestans, Clavibacter michiganense subsp. michiganense, Pseudomonas corrugata, Pectobacterium carotovorum subsp Carotovorum), etc.; Phomopsis vexans, Erysiphe cichoracearum, etc.; Alternaria japonica, White spot (Cercosporella brassicae) of cruciferous vegetables, ), etc.; cabbage rot (Pseudomonas syringae pv. marginalis), black rot (Xanthomonas campestris pv. campestris), etc.; lettuce rot (Pseudomonas cichorii, Pseudomonas viridiflava), bacterial spot disease (Xanthomonas campestris pv. vitians) green onions rust (Puccinia allii), etc.; soybean purpura (Cercospora kikuchii),

Elsinoe glycines, Diaporthe phaseolorum var. sojae, etc.; Colletotrichum lindemthianum, etc.; Cercospora personata, Cercospora arachidicola, etc. Powdery mildew of peas (Erysiphe pisi), etc.; summer plague of potatoes (Alternaria solani), late blight (Phytophthora infestans), leaf rot fungus (Rhizoctonia solani), etc.; powdery mildew of strawberries (Sphaerotheca humuli), etc.; Exobasidium reticulatum, Elsinoe leucospira, Pseudomonas syringae pv. theae, Xanthomonas campestris pv. (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tabacina), late blight (Phytophthora nicotianae), damping off (Ralstonia solanacearum), cavity disease (Pectobacterium carotovorum subsp. carotovorum), etc.; disease (Cercospora beticola), seedling wilt (Aphanomyces cochliodes), etc.; rose scab (Diplocarpon rosae), powdery mildew (Sphaerotheca pannosa), etc.; Puccinia horiana), Agrobacterium tumefaciens, etc.; Botrytis cinerea and Sclerotinia sclerotiorum on various crops such as eggplants, cucumbers and lettuce; Snow rot on lawns (Pythium) Iwayamai, Tyohula incarnate, Fu sarium nivale, Sclerotinia borealis), powdery mildew (Erysiphe graminis), Falling disease (Lycoperdon perlatum, Lepista subnudo, Marasmius oreades), false leaf rot (Ceratobasidium spp.), damping off (Gaemannomyces graminis), Curvularia leaf blight Curvularia geniculata, Rhizoctonia solani, Pythium periplocum, Pythium vanterpoolii, Puccinia spp., Sclerotinia homoeocarpa, etc.; Pythium aphanidermatum of bentgrass , Anthracnose (Colletotrichum sp.).

The compound of the present invention represented by the above formula (1) is active indoors in buildings including general houses, and damages or spoils wood and its processed products such as wooden furniture, stored food, clothing, books, etc. It can also be used to control arthropods and fungi that damage our lives. Specific pests include the following.

Termites of the phylum Arthropoda Insecta, such as Coptotermes formosanus, Reticulitermes speratus, other Reticulitermes hesperus, R. tibialis, R. flavipes, R. lucifugus, R. santonensis, etc.), Incisitermes minor, Odontotermes formosanus, Hodotermopsis jzponica, Cryptotermes domesticus, adults, larvae and egg;
Coleoptera, for example, Sitophilus zeamais, Sitophilus zeamais, etc., Sitophilus zeamais, Callosobruchus chinensis, Bruchus pisorum, Bruchus rufimanus, etc. Tribolium castaneum, Tribolium confusum, etc., Oryzaephilus surinamensis, Cryptolestes pusillus, etc., Lasioderma serricorne, Ginseng beetle (Stegobium paniceum), etc., Attagenus unicolor japonicus, Anthrenus verbasci, Dermestes maculatus, Gibbium aequinnoctiale, etc. Dinoderus minutus, Rhizopertha dominica, etc. Adults, larvae and eggs such as Lyctus brunneus of the family Lyctus brunneus;

Lepidoptera, for example, Cadra cautella, Ephestia kuehniella, Plodia interpunctella, etc., Sitotroga cerealella, etc., Tinea translucens), Tineola bisselliella, etc. adults, larvae and eggs;
Adults, larvae and eggs such as Cockroaches, for example, Blattella germanica, Periplaneta fuliginosa, Periplaneta japonica; Hymenoptera, for example, Monomorium pharaoni), adults, larvae and eggs such as monomorium nipponense;

Adults, larvae and eggs such as Ctenolepisma villosa, Lepisma saccharina, etc.
Adults, larvae and eggs of Diptera, such as Drosophila melangogaster of the family Drosophila, Piophila casei of the family Cheesefly, etc.;
Adults, larvae and eggs of Carpoglyphus lactis of the family Carpoglyphus;
Fungal wood-rotting fungi Tyromyces palustris, Coriolus versicolor, etc.;
Aspergillus niger, Aspergillus terreus, Aureobasidium pullulans, Chaetomium globosum, Cladosporium cladosporioides, Eurotium tonophilus, Fusarium moniliforme, Gliocladium virens, Myrothecium verrucaria, Penicillium citrinum, Penicillium funiculosum, Rhizopus oryzae, etc., which are degrading microorganisms of materials.

The compound of the present invention represented by the above formula (1) can also be used to control pests that damage or weaken trees in natural forests, artificial forests and urban green spaces. Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example, Calliteara argentata, Euproctis pseudoconspersa, Orygia recens approximans, Euproctis subflava, Lymantria dispar, etc. Malacosoma neustria testacea, Dendrolimus spectabilis, Dendrolimus superans, etc., Crytoblabes loxiella, etc., Agrotis segetum, etc. (Ptycholoma lecheana circumclusana), Cydia kurokoi, Cydia cryptomeriae, etc., Spilosoma imparilis, Hyphantria cunea, etc., Stigmella castanopsiella, etc. Adults, larvae and eggs of Parasa lepida, Scopelodes contracus, Microleon longipalpis, etc.; Agrilus spinipennis of the family, etc., Monochamus alternatus of the family Longhorn beetle, etc., Basilepta pallidula of the family Chrysomelidae, etc., Scepticus griseus of the weevil family, Shirahoshizo insidiosus ), etc., Sipalinus gigas, etc., of the family Barkworm (Tomicus piniperda), Indocryphalu s aceris), etc., adults, larvae and eggs such as Rhizopertha dominica of the family Rhizopertha;

Stink bugs, for example, Cinara todocola of the family Aphididae, Adelges japonicus of the family Aphididae, etc., Aspidiotus cryptomeriae of the family Aspidiotus, etc., Ceroplastes of the family ceriferus), adults, larvae and eggs;
Hymenoptera, e.g. Pachynematus itoi of the family Sawfly, etc., Neodiprion sertifer of the family Pine bee, etc., Adults, larvae and eggs of Dryocosmus kuriohilus of the family Bee, etc.; Diptera, e.g. Adults, larvae and eggs such as Tipula aino, etc., Strobilomyia laricicola, etc., Contarinia inouyei, Contarinia matsusintome, etc.;
Adults, larvae and eggs such as Oligonichus hondoensis and Oligonichus ununguis of Acarina of the phylum Arachnid of Arthropoda;
Nematozoa Phantomia Tylenx order, for example, Bursaphelenchus xylophilus of the family Parasitapherencidae.

The compound of the present invention represented by the above formula (1) is endogenous to vertebrates, particularly warm-blooded vertebrates such as cows, sheep, goats, horses, pigs, poultry, dogs, cats, fish, and other livestock and pets. It can also be used for the prophylaxis, treatment or control of arthropods, nematodes, flukes, tapeworms and protozoa that parasitize externally or externally. In addition to the above, target animal species include rodents such as mice, rats, hamsters and squirrels, carnivora such as ferrets, and pets and experimental animals such as birds such as ducks and pigeons. Specific pests include the following.

Diptera of the phylum Arthropoda Insecta, for example, Tabanus rufidens, Tabanus chrysurus, etc., Musca bezzii, Musca domestica, Stomoxys calcitrans, etc. Gasterophilus intestinalis, etc., Hypoderma bovis, etc., Oestrus ovis, etc., Aldrichina grahami, etc., Megaselia spiracularis, etc. Etc., Sepsis punctum, etc., Telmatoscopus albipunctatus, Psychoda alternata, etc., Culex pipiens molestus, Culex pipiens pallens , Anopheles sinensis, Culex pipiens triaeniorhynchus summorosus, Ades albopictus, etc., Simulium iwatense, Prosimulium yezoense, etc., Culicoides schulzei, Chicken midge ( Culicoides arakawae) and other adults, larvae and eggs;
Adults, larvae and eggs of the order Fleas, for example Pulex irritans of the family Pulex irritans, Ctenocephalides canis, etc.;

Louses, for example, pig lice (Haematopinidae suis) of the family Haematopinidae, bovine lice (Haematopinidae eurysternus), etc., horse lice (Damalinia bovis) of the family Amphipodidae, etc., bovine head lice (Linognathus vituli), etc. Adults, larvae and eggs such as (Menopon gallinae);
Acarina of the phylum Arachnid of Arthropoda, for example, Varroa jacobsoni of Varroa jacobsoni, Haemaphysalis longicornis of Haemaphysalis longicornis, Ixodes ovatus, Boophilus microplus, Amblyomma testudinarium), etc., Ornithonyssus sylvialum, etc., Dermanyssus gallinae, etc., Demodex phylloides, etc., Sarcoptes scabiei bovis, Trichymites Adults, larvae and eggs such as (Knemidocoptes mutans), Otodectes cynotis of the family Myroptera, and Psoroptes communis;
Nematoda Bilinear cocterosa, such as hookworm, pig kidneyworm, pig lungworm, hairy nematode, bovine tuberculosis, etc.:
Ascaris order, for example, pig roundworm, chicken roundworm, etc.;
Platyhelminthia fluke, for example, Schistosoma japonicum, Liver tetsu, Deer doublet fluke, Westermann lung fluke, Japanese chicken egg fluke, etc.;
Taenia, for example, tapeworms, tapeworms, tapeworms, tapeworms of Beneden, tapeworms, tapeworms, tapeworms, etc.:
Rhizomastigotes of the Protozoa phylum Flagellata, for example, Histomonas, etc., Protoflagellates, for example, Leishmania, Trypanosoma, etc., Polyflagellates, for example, Giardia, etc. Trichomonads, for example, Trichomonas, etc.:
Amoebiales of the Sarcophyte class, such as Entamoeba;
Subclass Piroplasma of the class Sporozoa, such as Theilaria, Babesia, etc., Subclass Latex, such as Eimeria, Plasmodium, Toxoplasma, etc.

The compound of the present invention represented by the above formula (1) is used to exterminate pests that directly harm or discomfort the human body, or to maintain public health conditions against pests that carry or mediate pathogens. can also be used for Specific pests include the following.

Lepidoptera of the phylum Arthropoda Insecta, for example, Sphageidus similis of the family Sphageidus similis, etc., Kunugia undans of the family Coleidae, etc., Parasa consocia of the family Parasa consociace, etc., Artona martini adults, larvae and eggs, etc.;
Coleoptera, for example, Xanthochroa waterhousei of the family Longhorn (Xanthochroa waterhousei), etc., Epicauta gohani (Epicauta gohani), etc. of the family Beetle family, adults, larvae, and eggs such as Paederus fuscipes (Paederus fuscipes);
Hymenoptera, for example Vespa simillima xanthoptera of the family Vespa simillima xanthoptera, etc., Brachyponera chinensis of the ant family, adults, larvae and eggs of the family Batozonellus annulatus, etc.;
Diptera, for example, Armigeres subalbatus of Mosquito family, Culicoides nipponensis of Culicoides family, Chironomus yoshimatsui of Chironomidae family, Simulium nikkoense of Blackfly family family, etc. such as Hirosia humilis of the family Housefly (Musca domestica), etc., Fannia canicularis of the family Himefly (Fannia canicularis), etc. adults, larvae and eggs;
Adults, larvae and eggs of the order Fleas, e.g. Pulex irritans of the family Pulex irritans;
Adults, larvae and eggs such as Cockroaches, for example, Blattella germanica of the family Cockroach family, Periplaneta americana of the family Cockroach family, Periplaneta americana, Black cockroach (Periplaneta fuliginosa), Yamato cockroach (Periplaneta japonica);
Adults, larvae and eggs such as Orthoptera (Orthoptera), for example, Diestrammena japonica and Diestrmmena apicalis of the family Cologgiaceae;
Adults, larvae and eggs of the order of the order Larvae, such as Pediculus humanus humanus, Phthirius pubis;
Adults, larvae and eggs of Isyndus obscurus of the family Reduviidae, such as Cimex lectularius, of the order Stink Bug, for example, Cimex lectularius;

Adults, larvae and eggs of the order Collembola of the phylum Arthropod Insecta, such as the Hypogastrura communis of the family Boraginidae;
Acarina of the phylum Arachnididae, for example, Ixodes persulcatus of the family Tick family, Ornithonyssus bacoti of the family Ornithonyssus bacoti, etc., Chelacaropsis moorei of the family Chelacaropsis moorei, etc., Pyemotes of the family Pyemotes Ventricosus), Demodex folliculorum, etc., Dermotophagoides pteronyssinus, etc., Sarcoptes scabiei, etc. Adults, larvae, and eggs of Trombicula akamushi, etc. ;
Eleganea, for example, Chiracanthium japonicum of the family Osmanthidae, etc., Heteropoda venatoria, etc. of the family Spermidae, Spermophora senoculata of the family Pholcus phalangioides, etc., Uroctea compactilis of the family Uroctea compactilis ), adults, larvae and eggs such as Plexippus paykulli and Plexippus adansoni of the family Jumping Spider;
Adults, larvae and eggs of the Scorpion order, such as the spotted scorpion (Isometrus europaeus) of the family Arctic Scorpion;
Adults, larvae and eggs such as Scolopendra subspinipes mutilans and Scolopendra subspinipes japonica of the family Scolopendra subspinipes japonica;
Adults, larvae and eggs, such as the order of the Lagoonia family, for example Thereuronema hilgendofi;
Adults, larvae and eggs, such as Oxidus gracilis of the family Oxidus gracilis, of the order Arthropoda Diopoda;
Adults, larvae and eggs of the order Isopoda of the phylum Crustacea of the phylum Arthropoda, for example Porcellio scaber of the family Woodlouse;
Annelid phylum Verniercidae, for example, Yamabiru (Haemadipsa zeylanica japonica) of the family Yamabiru, etc.;
Trichophyton rubrum, Trichophyton mentagrophytes, etc., which are trichophyton fungi, Candida albicans, etc., which are candida fungi, Aspergillus fumigatus, etc., fungi such as Aspergillus fumigatus, Escherichia coli, Gram-negative bacteria such as Pseudomonas aeruginosa, Staphylococcus aureus Gram-positive bacteria such as aureus and the like.

The compound of the present invention represented by the above formula (1) is a pest that damages trees and ornamental plants in agricultural crops, natural forests, artificial forests, and urban green spaces, such as arthropods, gastropods, nematodes, It is of particular value in controlling fungi. In such situations, the compounds of the present invention, in their commercially useful formulations and use forms prepared by those formulations, can be combined with other active compounds such as insecticides, acaricides, nematicides, fungicides. It can also be present as an admixture with agents, synergists, plant regulators, baits or herbicides.
Usable forms include wettable powders, wettable granules, dry flowables, water solutions, emulsions, liquids, oils, water suspensions, water emulsions and other flowables, capsules, powders, granules, and fine powders. It can take granules, baits, tablets, sprays, aerosols, aerosols and the like. In order to obtain these dosage forms, various pesticide adjuvants conventionally used in the technical field of agricultural and horticultural agents can be used as appropriate. Such an agricultural chemical adjuvant can be used, for example, for the purpose of improving the effects of agricultural and horticultural agents, stabilizing them, and improving their dispersibility.

Agrochemical adjuvants include, for example, carriers (diluents), emulsifiers, wetting agents, dispersants, disintegrants and the like. Liquid carriers include water, aromatic hydrocarbons such as toluene and xylene, alcohols such as methanol, butanol and glycol, ketones such as acetone, amides such as dimethylformamide, sulfoxides such as dimethylsulfoxide, and methylnaphthalene. , cyclohexane, animal and vegetable oils, fatty acids and the like. As solid carriers, clay, kaolin, talc, diatomaceous earth, silica, calcium carbonate, montmorillonite, bentonite, feldspar, quartz, alumina, sawdust, nitrocellulose, starch, gum arabic and the like can be used.
Usual surfactants can be used as emulsifiers and dispersants, for example, anionic surfactants such as higher alcohol sodium sulfate, stearyltrimethylammonium chloride, polyoxyethylene alkylphenyl ether, and lauryl betaine. , cationic surfactants, nonionic surfactants, amphoteric surfactants and the like can be used.
Wetting agents such as dialkyl sulfosuccinate, sticking agents such as carboxymethyl cellulose and polyvinyl alcohol, and dispersing agents such as sodium ligninsulfonate and sodium lauryl sulfate can also be used.
Of course, one or a combination of two or more of the compounds of the present invention can be blended as an active ingredient. The content of the compound of the present invention as an active ingredient in these formulations is, for example, 0.01 to 99.5% by mass, preferably selected from the range of 0.5 to 90% by mass. It may be determined appropriately depending on various conditions, but for example, about 0.5 to 20% by mass, preferably 1 to 10% by mass, for powders, and about 1 to 90%, preferably 10% by mass for wettable powders. ~80% by mass, for emulsions, about 1~90% by mass, preferably 10~40% by mass.

For the control of arthropods, gastropods, nematodes, and fungi, foliage of plants is usually applied to areas where damage by these pests is occurring or is likely to occur. In addition to spraying on the soil, it can be applied to the soil, etc. by applying it to the soil, etc., such as mixing all layers of the soil, applying it to the soil, applying it to the bed soil, treating the cell seedling, treating the planting hole, treating the root of the plant, top dressing, treating the rice box, applying it to the surface of the water, etc. It can also be used after being absorbed from It can also be used by immersing seeds in chemicals, seed dressing, seed treatment such as Culper treatment, application to nutrient solution in nutrient solution (hydroponics) cultivation, smoking or trunk injection. When used, it varies depending on the type and amount of pests, the type of target crops/trees, cultivation mode, and growth conditions, but in general, the amount of active ingredient is 0.1 to 1000 g, preferably 1 to 100 g, per 10 ares. apply. In order to process this, wettable powders, wettable granules, dry flowables, water solutions, emulsions, liquids, water suspensions, water emulsions and other flowables, capsules, etc. should be diluted with water, Although it varies depending on the type of target plant, cultivation mode, and growth state, it is generally sufficient to spray crops at an application rate of 10 to 1,000 liters per 10 ares. In the case of powders, sprays, or aerosols, crops or the like may be treated in the form of the formulation.
When the target pests mainly damage plants in the soil, or when the target pests are controlled by absorbing the chemical from the roots, for example, the formulation is diluted with water or not diluted. method of applying to the root of the plant or the nursery for raising seedlings, etc., method of spraying granules to the root of the plant or the nursery for raising seedlings, powder, wettable powder, water granules before sowing or transplanting A method of spraying blends, granules, etc. and mixing them with the entire soil, before sowing or before planting plants, applying powders, wettable powders, wettable granules, granules, fine granules, etc. to planting holes, rows, etc. and the like. Wettable powders, water dispersible granules, water solutions, emulsions, liquids, suspensions in water, emulsions in water, and other flowable agents, capsules, etc. are diluted with water. It can be sprayed on the surface of the soil or irrigated into the soil so that it is evenly spread over the entire area to be treated. In the case of powders, granules, fine granules, baits, etc., the formulation state is evenly spread over the entire area to be treated. It should be sprayed on the soil surface as much as possible. Spraying or irrigation may be done around seeds or crops/trees to be protected from damage. The active ingredient can also be mechanically dispersed by tilling during or after application.

As for the method of application to nursery boxes for paddy rice, the dosage form may differ depending on the application period, such as application at the time of sowing, application during the greening period, and application at the time of transplantation. It may be applied in a dosage form such as granules. It can also be applied by mixing with potting soil, and mixing potting soil with powders, wettable granules, granules or fine granules, for example, mixing with bed soil, mixing with covering soil, mixing with the whole potting soil, etc. can. Alternatively, the culture soil and various formulations may simply be layered alternately and applied.
As for the method of application to paddy fields, solid formulations such as jumbo formulations, pack formulations, granules and wettable granules, and liquid formulations such as flowables and emulsions are usually sprayed over flooded paddy fields. In addition, at the time of rice planting, a suitable formulation can be sprayed or injected into the soil as it is or mixed with fertilizer or the like. In addition, by using chemical solutions such as emulsions and flowables at water outlets, irrigation systems, and other sources of water flowing into paddy fields, it is possible to apply the chemicals in a labor-saving manner along with the supply of water.
Seed treatment methods include, for example, a method of immersing seeds in a liquid state with or without diluting a liquid or solid formulation to adhere and permeate the drug, mixing a solid or liquid formulation with seeds, Examples include a method of applying powder coating to the surface of seeds, a method of coating seeds by mixing with a binder such as resin or polymer, and a method of spraying near seeds at the same time as planting. The "seed" to be subjected to the seed treatment means a plant body in the early stage of cultivation used for plant propagation. Plants for propagation can be mentioned. In addition, the "soil" or "cultivation carrier" of the plant when applied refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited, but the plant Any material can be used as long as it can grow, and so-called soil, seedling mat, water, etc. may be used. rock wool, glass wool, wood chips, bark and the like.
As for the sowing of cultivated plants to be transplanted and the treatment during the seedling-raising period, in addition to the direct treatment of the seeds, the irrigation treatment of liquid chemicals or the spraying treatment of granules to the nursery bed for raising seedlings is preferable. It is also preferable to treat the granules in the planting holes at the time of planting, or to mix them with cultivation carriers in the vicinity of the place of transplantation.

The compound of the present invention represented by the formula (1) protects wood (standing tree, fallen tree, processed wood, stored wood or structural wood) from damage by insects such as termites or coleoptera and fungi. Also worth it. In such a situation, it is possible to control the wood or the soil around it by spraying, injecting, irrigating, or applying oil, emulsion, wettable powder, or sol, or by spraying powder, granules, etc. can. Also, the oils, emulsions, wettable powders, powders, etc. used in this context may be mixed with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists. In these formulations, the total amount of active ingredient compounds is 0.0001 to 95% by mass, preferably 0.005 to 10% by mass for oil solutions, powders and granules, emulsions, wettable powders and sols. can be contained in an amount of 0.01 to 50% by mass. When controlling arthropods, fungi, etc., 0.01 to 100 g of the active ingredient compound per 1 m ² is sprayed on the soil or wood surface.

The compound of the present invention represented by the above formula (1) is useful in storing products such as cereals, fruits, nuts, spices and tobacco as they are, powdered or mixed in products. It can be used to protect against damage by orders, coleoptera, mites and fungi. Animal products (skins, wool, wool and feathers, etc.) and plant products (cotton, paper, etc.) are also protected from attack by Lepidoptera, Coleoptera, Spots and Cockroaches when stored in their natural or transformed state. It can also protect against attack by Lepidoptera, Coleoptera, Flies and Mites when storing foods such as meat and fish. In such situations, spraying oil solutions, emulsions, wettable powders, powders, etc., installing resin transpiration agents, etc., treating fumigants and aerosols, installing granules, tablets and poison baits, spraying aerosols, etc. can be prevented by These formulations can also be present as admixtures with other active compounds such as insecticides, acaricides, nematicides, fungicides, repellents or synergists, in these formulations can contain 0.0001 to 95% by mass of active ingredient compounds in total.

The compound of the present invention represented by the above formula (1) is parasitic on the body surface of humans and domestic animals and directly harms arthropods and fungi such as skin feeding and blood sucking, and diseases of humans and domestic animals. value in the control or prevention of arthropods, nematodes, trematodes, tapeworms, protozoa, and arthropods that cause discomfort to humans that are vectors of such diseases. There is In such situations, the compounds of the present invention may be incorporated in small amounts in food or feed, or in suitable orally ingestible compounded pharmaceutical compositions, such as tablets, pills, and the like, containing pharmaceutically acceptable carriers and coating materials. Capsules, pastes, gels, beverages, medicated feeds, medicated drinking water, medicated feeds, slow-release large pills, other slow-release devices designed to be retained in the gastrointestinal tract, etc. Orally administered, or as sprays, powders, It can be administered transdermally as greases, creams, ointments, emulsions, lotions, spot-ons, pour-ons, shampoos and the like. In order to achieve effects in such applications, the formulation generally contains 0.0001 to 0.1% by mass, preferably 0.001 to 0.01% by mass, of the active ingredient compound. As a method of transdermal or topical administration, a device (eg, collar, medallion, ear tag, etc.) attached to the animal for local or systemic control of arthropods can also be used.

Specific oral administration methods and transdermal administration methods when the compound of the present invention represented by the above formula (1) is used as an anthelmintic for animals such as livestock and pets, or humans are shown, but are not necessarily limited to these. not something.
When administered orally as a medicated drink, the drink is usually dissolved, suspended or dispersed in a suitable non-toxic solvent or water with suspending or wetting agents such as bentonite or other excipients. be. Beverage formulations generally contain 0.01-1.0% by weight of active compound, preferably 0.01-0.1% by weight.
When it is desired to administer orally in a dry solid unit dose form, capsules, pills or tablets usually containing predetermined amounts of the active ingredient are employed. These use forms are obtained by intimately blending the active ingredient with suitable finely divided diluents, fillers, disintegrants and/or binders such as starch, lactose, talc, magnesium stearate, vegetable gums and the like. manufactured. Such unit dose formulations can vary widely in mass and content of anthelmintic depending on the species of host animal to be treated, the degree of infection and type of parasite and the body weight of the host.

When administered via animal feed, it can be dispersed homogeneously in the feed, used as a top dressing, or used in the form of pellets. Usually 0.0001 to 0.05%, preferably 0.0005 to 0.01% by weight of the active ingredient compound is included in the final feed to achieve the desired antiparasitic effect.
Dissolved or dispersed in a liquid carrier vehicle, they can be administered to animals parenterally by intraforestomatric, intramuscular, intratracheal or subcutaneous injection. For parenteral administration, the active compound is preferably mixed with a suitable vegetable oil such as peanut oil, cottonseed oil. Such formulations generally contain from 0.05 to 50% by weight of active compound, preferably from 0.1 to 5.0% by weight.
It can also be administered topically by mixing with a suitable carrier such as dimethylsulfoxide or a hydrocarbon solvent. The formulation is applied directly to the external surface of the animal by spraying or direct pouring.
In addition, the compounds of the present invention represented by the above formula (1) can be used as anthelmintic agents for arthropods that directly harm them or arthropods that act as disease vectors when their pests are latent. Spraying, injecting, irrigating, and applying oil solutions, emulsions, wettable powders, etc., spraying powders, etc., fumigants, mosquito coils, self-burning fumigants, chemically reactive fumigants against the surrounding environment that is wet Heated aerosols, fumigants such as fogging, treatment of ULV agents, etc., installation of granules, tablets and poison baits, or floating powders, granules, etc. in waterways, wells, reservoirs, water tanks and other running or standing water It can also be used by a method such as dropwise addition to. In addition, it is possible to control worms and the like, which are also agricultural and forest pests, in the same manner as described above, and for worms, etc., it is possible to mix them in livestock feed and mix them with feces. For mosquitoes, it is also effective to use an electric mosquito trap to volatilize it into the air. It should be noted that these use forms formulations can also be present as admixtures with other active compounds such as pesticides, acaricides, nematodes, disease controllers, repellents or synergists. , the total amount of active ingredient compounds contained in these preparations is 0.0001 to 95% by mass.

The compounds of the invention of formula (1) above may also be present as admixtures with other active compounds. Especially for controlling pests such as arthropods, gastropods, and nematodes that damage plants when used in combination with compounds (insecticides) having pest control activity, mite control activity or nematode control activity On the other hand, it becomes possible to expand the pests to be controlled, and a synergistic effect such as a reduction in the amount of chemicals can be expected. Specific examples of active compounds include the following.

organophosphorus agents such as acephate, azinphos-methyl, chlorpyrifos, daizinon, dichlorvos, dimeton-S-methyl, dimethoate, dimethylvinphos, disulfoton, ethion, fenitrothion, fenthion, isoxathion, malathion, methamidophos, methidathion, monocrotophos ( monocrotophos, naled, oxideprofos, parathion, phenthoate, phosalone, pirimiphos-methyl, piridafenthion, profenofos, prothiofos ), propaphos, pyraclofos, salition, sulprofos, thiometon, tetrachlorvinfos, trichlorphon, vamidothion, etc.;
Carbamates, such as alanycarb, bendiocarb, benfuracarb, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, furatiocarb (furathiocarb), isoprocarb, methomyl, metolcarb, pirimicarb, propoxur, thiodicarb, etc.;
organochlorine agents such as aldrin, chlordane, DDT (p,p'-DDT), endosulfan, lindane, etc.;

Pyrethroid agents such as acrinathrin, allethrin, bifenthrin, cycloprothrin, cyfluthrin, cyhalothrin, cyphenothrin, cypermethrin, deltamethrin ( deltamethrin, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flufenprox, fluvalinate, furamethrin, halofen halfenprox, imiprothrin, permethrin, phenothrin, prallethrin, pyrethrins, resmethrin, silafluofen, tefluthrin, tralomethrin, trans transfluthrin, etc.;
Neonicotinoid agents such as acetamiprid, clothianidin, dinotefran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, etc.;
Diamide agents such as chlorantraniliprole, cyantraniliprole, cyclaniliprole, flubenziamide, tetraniliprole, etc.;
Phenylpyrazole agents such as ethiprole, fipronil, acetoprole, pyrafluoprole, pyriplore, etc.;
nereistoxin agents such as bensultap, cartap, thiocyclam, thiosultap, etc.;
Insect growth regulators such as phenylbenzoyl ureas and diacylhydrazines, e.g. chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron (novaluron), teflubenzuron, triflumuron, buprofezin, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, cyromazine, etc.;
Juvenile hormone agents such as diofenolan, fenoxycarb, hydroprene, methoprene, pyriproxyfen, etc.;

insecticidal substances produced by microorganisms, such as abamectin, emamectin-benzoate, ivermectin, lepimectin, milbemectin, nemadectin, Nikkomycin , polyoxin complex (polioxin), spinetram (spinetram), spinosad (spinosad), BT agents, etc.;
Naturally derived insecticidal substances, such as anabasine, azadiractin, deguelin, decanolyoctanoylglycerol, hydroxypropyl starch, soybean lecithin, nicotine ), nornicotine, oreic acid sodium salt, petroleum oil, propylene glycol monolaurate, rape oil, rotenone, sorbitan fatty acid ester ( Sorbitan fatty acid ester), starch, etc.;
Other insecticides such as aphidpyropen, benzpyrimoxan, broflanilide, chlorfenapyr, diafenthiuron, dicloromezotiaz, dimpropyridaz , DBEDC (dodecylbenzenesulphonic acidbisethylenediamine copper [II] salt), flonicamid, flometoquin, flufenerim, flupyradifurone, flupyrimin, fluralaner, fluhexafon, fluxametamide ), hydramethylnon, indoxacarb, isocycloseram, metaflumizone, metaldehyde, nicotin sulfate, oxazosulfyl, pymetrozine pymetrozine, pyridalyl, pyrifluquinqzon, spirotetramat, sulfoxaflor, tolfenpyrad, triazamate, triflumezopyrim, tyclopyrazoflor etc;

Acaricides such as acequinocyl, acinonapyr, amidoflumet, amitraz, azocyclotin, benzoximate, bifenazate, binapacryl, phenisobromo bromopropylate, chinomethionat, clofentezine, cyenopyrafen, cyflumetofen, cyhexatin, dicofol, dienochlor, ethoxazole , fenazaflor, fenazaquin, fenbutatin oxide, fenothiocarb, fenpyroximate, fluacrypyrim, hexythiazox, pirimidifen, polynactins, propargite, pyflubumide, pyridaben, spirodiclofen, spiropidion, spiromesifen, tebufenpyrad, tetradifon and flupentiofenox )etc:
Nematicides such as aluminum phosphide, benclothiaz, cadusafos, ethoprophos, fluazaindolizine, fluensulfone, fosthiazate, furfural ( furfural, imicyafos, levamisol hydrochloride, mesulfenfos, metam-ammonium, methyl isothiocyanate, morantel tartrate, oxamyl, thioxazafen, etc. ;
Poison baits such as chlorphacinone, coumatetralyl, diphacinone, sodium fluoracetate, warfarin, and the like.

The compounds of the present invention represented by formula (1) above can also be present in admixture with other active compounds other than the compounds having pesticidal, acaricidal or nematicidal activity. In order to control diseases and / or weeds that occur at the same time during the use period, by using it in combination with a compound having fungicidal activity, herbicidal activity or plant growth regulating activity, it is possible to reduce control effort and reduce the amount of medicine. A synergistic effect can also be expected. In addition, when used in combination with repellents, synergists, etc., a more effective control effect such as a synergistic effect can be expected.

Specific active compounds thereof include disease control agents such as D-D (1,3-dichloropropene), acibenzolar-S-methyl, aldimorph, ametoctradin, amisulbrom, and andoprim, anilazine, azaconazole, azoxystrobin, basic copper sulfate, benodanil, benomyl, benthiavalicarb -isopropyl), benthiazole, bitertanol, bixafen, blasticidin S, boscalid, bromuconazole, calcium carbonate, butiobate ( buthiobate, calcium polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, chinomethionat, chlorfenazole , chloroneb, chloropicrin, chlorothalonil, chlorozolinate, DBEDC (complex of bis(ethylenediamine) copper-bis-(dodecylbenzenesulfonic acid)), cupric hydroxide, nonylphenol sulfone copper nonylphenol sulfonate, copper oxychloride, cyazofamid, cyflufenamid, cymoxanil, cyproconazole oconazole), cyprodinil, dazomet, diclobutrazol, dichlofluanid, dichlone, diclocymet, diclomezine, diethofencarb, difenoconazole ( difenoconazole), diflumetorim, dimethomorph,

dimoxystrobin, diniconazole, diniconazole-M, dithane-stainless, dithianon, dodine, eclomezole, edifenphos , enestrobin, epoxiconazole, etaconazole, ethaboxam, extract from mushroom, famoxadone, fenamidone, fenarimol, fen buconazole, fenfuram, fenhexamid, fenoxanol, fenpiclonil, fenpropidin, fenpyrazamine, ferimzone, fluazinam , flumetover, flumorph, fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusulfamide, flutolanil, fluxapyroxad, folpet, fosetyl-AL, fthalide, fuberidazole, fludioxonil, flusilazole ), flutianil, flutriafol, furametpyr, fluconazole, guazatine, hexaconazole (h exaconazole, hydroxyioxazole, hymexazol, imazalil, imazalil sulfate,

imibenconazole, iminoctadine acetate, iminoctadine-DBS, ipconazole, IBP (iprobenfos), iprodione, iprovalicarb, isofetamide , isoprothiolane, isopyrazam, isotianil, kasugamycin, kresoxim-methyl, mancozeb, mandipropamid, maneb, manzeb, mepanipyrim, mepronil, metalaxyl, metam-ammonium, metam-sodium, metconazole, methasulfocarb, methyl bromide , methylisothiocyanate, metominostrobin, metrafenone, mildiomycin, myclobutanil, nickel dimethyldithiocarbamate, nuarimol, orysastrobin , oxadixyl, oxathiapiprolin, oxine-copper, oxolinic acid, oxpoconazole fumarate, oxycarboxin, oxytetracycline (oxytetracycline), pebulate, pefurazoate, penconazole,

pencycuron, penflufen, penthiopyrad, picarbutrazox, picoxystrobin, piperalin, polycarbamate, polyoxin-B, polyoxins, potassium hydrogen carbonate, probenazole, prochloraz, procymidone, propamocarb, propiconazole, propineb, proquinazid ( proquinazid, prothioconazole, pyraclostrobin, pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril, pyrifenox ), pyrimethanil, pyriofenone, pyroquilon, quinoxyfen, quintozene, sedaxane, silver, simeconazole, sodium hydrogen carbonate , sodium hypochlorite, spiroxamine, streptomycin, sulfur, tebfloquin, tebuconazole, tecloftalam, terbinafine, tetraconazole ( tetraconazole, thiabendazole, thiadiazin, thifluzamid e), thiophanate, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolprocarb, tolylfluanid, triadimefon, triadimenol, triclopyricarb, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole , uniconazole-P, validamycin (-A), vinclozolin, zarilamid, zinc sulfate, zineb, ziram, zoxamide etc. can be exemplified.

Compounds having herbicidal activity include, for example, acronifen, acifluofen-sodium, alachlor, alloxydim, amicarbazone, amidosulfuron, anilofos ), aslam, atrazine, azimsulfuron, benfuresate, bensulfuron-methyl, bentazone, benthiocarb, benzobicyclon, benzo benzofenap, bialaphos, bifenox, bromobutide, bromoxynil, butamifos, caffenstrole, calcium peroxide, carbetamide, cinosulfuron (cinosulfuron), clomeprop, cyclosulfamuron, cyhalofop-butyl, daimuron, desmedipham, diclofop-methyl, diflufenican ( diflufenican, dimefuron, dimethametryn, dinoterb, diquat, diuron,

esprocarb, ethiozin, ethofumesate, ethoxysulfuron, etobenzanid, fenoxaprop-P-ethyl, fentrazamide, flucarbazone, flufenacet, flurtamone, fluthiacet-methyl, foramsulfuron, glufosinate-ammonium, glyphosate-isopropyl amine, glyphosate trimesium (glyphosate-trimesium), imazapyr, imazosulfuron, indanofan, iodosufluron, ioxynil-octanoate, isoproturon, isoxadifen, isoxaflutole ( isoxaflutole, lactofen, linuron, mefenacet, mesosulfuron, metamitron, methabenzthiazuron, metosulam, metribuzin, napropamide ), neburon, oxadiargyl, oxadiazon, oxaziclomefone, paraquat, pendimethalin, pentoxazone, phenmedipham, pretilachlor , propoxycarbazone, prosulfocarb, pyracloni l), pyraflufen-ethyl, pyrazolate, pyrazosulfuron-ethyl, pyributicarb, pyriftalid, pyriminobac-methyl, quizalofop exemplify quizalofop-ethyl, sethoxydim, simazine, sulcotrione, sulfentrazone, thenylchlor, triaziflam, tribufos, etc. can be done.

In addition, compounds having a plant growth regulating action include, for example, 1-naphthylacetic acid, 4-CPA (4-CPA), benzylaminopurine, butralin, calcium chloride ( calcium chloride, calcium formate, calcium peroxide, calcium sulfate, chlormequat chloride, choline, cyanamide, cyclanilide, daminozide ), decyl alcohol, dichjoprop, ethephon, ethychlozate, flurprimidol, forclorfenuron, gibberellic acid, indole butyric acid (indolebutyric acid), maleic hydrazide potassium salt, mefenpyr, mepiquat chloride, oxine sulfate, 8-hydroxyquinoline sulfate, paclobutrazol , paraffin, prohexadione-calcium, prohydrojasmon, thidiazuron, trinexapac, uniconazole-P, wax, It can also be used by mixing with the like.
Repellents such as capsaicin, carane-3,4-diol, citronellal, deet, dimethyl phthalate, hinokitiol, limonene ( limonene, linalool, menthol, menthone, naphthalene, thiram and the like.
Examples of synergists include methylenedioxynaphthalene, naphthyl propynyl ether, nitrobenzyl thiocyanate, octachlorodipropyl ether, pentynyl phthalimide ( pentynyl phthalimide, phenyl sarioxon, piperonyl butoxide, safrole, sesamex, sesamin, sulfoxide, triphenyl phosphate, verbutin ) etc. can be mentioned.

The compounds of the present invention can be used as biopesticides, for example, cytoplasmic polyhedrosis virus (CPV), entomopox virus (EPV), granulosis virus (GV), nuclear polyhedrosis virus ( Virus preparations such as nuclear polyhedrosis virus (NPV), Beauveria bassiana, Beauveria brongniartii, Monacrosporium phymatophagum, Paecilomyces fumosoroseus, Pasteuria penetrans ), Steinernema carpocapsae, Steinernema glaseri, Steinernema kushidai, Verticillium lecanii, etc. microbial pesticides, Agrobacterium radiobacter, Bacillus subtilis, non-pathogenic Erwinia carotovora, non-pathogenic Fusarium oxysporum, Pseudomonas CAB-02 ( Pseudomonas CAB-02), Pseudomonas fluorescens, Talaromyces flavus, Trichoderma atroviride, Trichoderma lignorum, microbial pesticides used as fungicides, Xanthomonas・Similar effects can be expected by mixing with biopesticides such as Xanthomonas campestris, which are used as herbicides.

Furthermore, as biological pesticides, for example, Amblyseius californicus, Amblyseius cucumeris, Amblyseius degenerans, Aphidius colemani, Aphidoletes aphidimyza, Yamato lacewing ( Chrysoperia carnea, Dacnusa sibirica, Diglyphus isaea, Encarsia formosa, Eretmocerus eremicus, Franklinothrips vespiformis, Harmonia axyridis, Crested wasp (Hemiptarsenus varicornis), Leafless leaflet (Neochrysocharis formosa), Small-spotted stink bug (Orius sauteri), Orius strigicollis, Chilean tick (Phytoseiulus persimilis), Black gourd mistletoe (Pilophorus typicus), Stink bug (Piocoris) varius), natural enemy organisms such as codrelure, cuelure, geraniol, gyptol, liblure, looplure, methyl eugenol, orfralure, Pheromone agents such as peachflure, phycilure, pyrimalure and turpentine can also be used in combination.

Hereinafter, the present invention will be further described in detail with reference to Examples, Formulation Examples and Test Examples, but the scope of the present invention is not limited by these Examples, Formulation Examples and Test Examples.

Example 1. N-(Cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (Compound No.: A -7 ) synthesis
N,N-dimethylformamide (12 mL ) of N-{4-(cyanomethyl)-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (1.28 g ) 60% Sodium hydride (0.13 g) was added to the solution and stirred at room temperature for 6 minutes. After that, bromoacetonitrile (216 μL) was added, and the mixture was stirred at room temperature for 6 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give N-(cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2- a]pyridine-2-carboxamide 0.30 g (mp: 147-149°C) was obtained.

Example 2. N-(Cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylsulfinyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (Compound No.: A-8 ) Synthesis
of N-(cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (0.075 g) 65% 3-chloroperbenzoic acid (0.040 g) was added to a chloroform (3 mL) solution, and the mixture was stirred at room temperature for 7 hours. Saturated sodium bicarbonate water was added to the reaction solution, and the organic layer was separated with chloroform. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give N-(cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylsulfinyl)-6-(trifluoromethyl)imidazo[1,2 -a]pyridine-2-carboxamide 0.056 g (mp: 182-183°C) was obtained.

Example 3. N-(Cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (Compound No.: A-9 ) synthesis
of N-(cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylthio)-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (0.15 g) 65% 3-Chloroperbenzoic acid (0.18 g) was added to a chloroform (3 mL) solution, and the mixture was stirred at room temperature for 7 hours. Saturated sodium bicarbonate water was added to the reaction solution, and the organic layer was separated with chloroform. The obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to give N-(cyanomethyl)-N-{4-(trifluoromethyl)phenyl}-3-(ethylsulfonyl)-6-(trifluoromethyl)imidazo[1,2 -a]pyridine-2-carboxamide 0.14 g (mp: 190-193°C) was obtained.

^*1：回転異性体A及びBの約５：１の比の混合物を示す。 Table 2 below shows the ¹ H-NMR data of compounds prepared in the same manner as in the above examples.
Table 2

^*1 : indicates a mixture of rotamers A and B in a ratio of about 5:1.

Formulations containing the compound of the present invention will be specifically described below with reference to formulation examples, but the compounds of the present invention, auxiliary components and their addition amounts are not limited only to the following formulation examples. In addition, all the parts in the formulation examples represent parts by mass.

Formulation Example 1 Emulsion compound of the present invention (10 parts), N-methyl-2-pyrrolidone (reagent) (10 parts), xylene (reagent) (70 parts), Sorpol 3005X (nonionic surfactant and anionic interface A mixture of activators (Toho Chemical Industry Co., Ltd.) (10 parts) was uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 2 Wettable powder Compound of the present invention (20 parts), Toxil GU-N (white carbon, Oriental Silicas Corporation) (20 parts), Sorpol 5096 (polyoxyethylene styrylphenyl ether sulfate, Toho Chemical Industry Co., Ltd.) ( 10 parts) and SS clay (clay, Showa KDE Co., Ltd.) (50 parts) were mixed and pulverized using a pulverizer to obtain a wettable powder.

Formulation Example 3 Aqueous solvent The compound of the present invention (5 parts), Lunox P-65L (sodium alkylbenzenesulfonate, Toho Chemical Industry Co., Ltd.) (3 parts), and sodium hydrogen carbonate (reagent) (92 parts) were uniformly mixed. After that, it was pulverized using a pulverizer to obtain a water solvent.

Formulation Example 4 Flowable agent Compound of the present invention (20 parts), Sorpol 7948 (polyoxyalkylene tristyrylphenyl ether sodium sulfate, Toho Chemical Industry Co., Ltd.) (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance and wet pulverized with a bead mill to obtain a slurry. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was well mixed and dispersed in water (24.8 parts) to prepare a gel-like product, which was thoroughly mixed with the slurry to obtain a flowable agent. .

Formulation Example 5 EW-1
After mixing and homogenizing the compound of the present invention (20 parts) and Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (15 parts), water (59.8 parts) is gradually added while stirring. In addition, a dispersion was obtained. This dispersion was dispersed in propylene glycol (reagent) (5.0 parts), and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) was added to obtain an emulsion preparation.

Formulation Example 6 EW-2
The compound of the present invention (10 parts) was dissolved in xylene (10 parts) and mixed with Rheodol 430V (polyoxyethylene sorbitol tetraoleate, Kao Corporation) (24 parts) to obtain a dispersion. This dispersion and water (50.8 parts) were dispersed with a homogenizer, and KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) dispersed in propylene glycol (reagent) (5.0 parts) was added. to obtain an emulsion formulation.

Formulation Example 7 Microemulsion Compound of the present invention (10 parts), xylene (reagent) (20 parts), Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (20 parts), Airol CT-1L (dioctyl Sodium sulfosuccinate (Toho Chemical Industry Co., Ltd.) (2.0 parts) and water (48 parts) were uniformly mixed to obtain a microemulsion.

Formulation Example 8 Liquid formulation The compound of the present invention (20 parts), Н-methyl-2-pyrrolidone (reagent) (70 parts), Nucalgen D-230 (polyoxyethylene castor oil, Takemoto Oil Co., Ltd.) (10 parts) and dissolved to obtain a liquid agent.

Formulation Example 9 Granules-1
Compound of the present invention (5 parts), Airol CT-1L (sodium dioctyl sulfosuccinate, Toho Chemical Industry Co., Ltd.) (2 parts), bentonite Sado (bentonite, Kunimine Industry Co., Ltd.) (30 parts), NK-300 (clay , Showa KDE Co., Ltd.) (63 parts) were uniformly mixed, water was added, and the mixture was kneaded well.

Formulation Example 10 Granules-2
The compound of the present invention (5 parts) was dissolved in methanol (reagent), adsorbed to Ishikawa Light No. 2 (95 parts) using a tumbling granulator, and dried to obtain granules.

Formulation Example 11 Microgranules-1
The compound of the present invention (2 parts) was dissolved in methanol (reagent), adsorbed on Ishikawa Light No. 4 (98 parts) using a tumbling granulator, and dried to obtain fine granules.

Formulation Example 12 Microgranules-2
The compound of the present invention (5 parts) and Tokusil GU-N (5 parts) were mixed, pulverized using a fine pulverizer, and uniformly mixed with Iide silica sand (silica sand, JFE Mineral Co., Ltd.) (80 parts). This mixture was further mixed while spraying an aqueous solution obtained by diluting Toxanon GR-31A (polycarboxylic acid type surfactant, Sanyo Chemical Industries, Ltd.) (10 parts) to obtain a granular composition. This granular composition was dried to obtain fine granules.

Formulation Example 13 Dust agent The compound of the present invention (5 parts), Tokusil GU-N (5 parts) and Omori fine powder clay (clay, Taisei Sangyo Co., Ltd.) (90 parts) were uniformly mixed and then ground using a pulverizer. It was pulverized to obtain a powder.

Formulation Example 14 DL powder A compound of the present invention (5 parts), propylene glycol (0.5 part) and DL clay (94.5 parts) were uniformly mixed and pulverized using a pulverizer to obtain a powder.

Formulation Example 15 Seed Coating Powder The compound of the present invention (10 parts), Poval PVA-117 (polyvinyl alcohol, Kuraray Trading Co., Ltd.) (1 part) and Omori fine clay (89 parts) are uniformly mixed and milled. to obtain a powder. The pre-moistened seeds were mixed with this powder and air-dried to obtain coated seeds.

Formulation Example 16 Seed-coated flowable agent The compound of the present invention (10 parts), Sorpol 7948 (5 parts), propylene glycol (reagent) (10 parts), and water (40 parts) were mixed in advance, and wet pulverized with a bead mill. and a slurry was obtained. Next, KELZAN (xanthan gum, Sansho Co., Ltd.) (0.2 parts) and water (29.8 parts) were thoroughly mixed and dispersed, and AMECOAT HCA/83 (acrylic acid polymer, SOLVAY) (5 parts) was mixed into a gel. prepared. The slurry and the prepared gel were thoroughly mixed to obtain a flowable agent. This flowable agent and seeds were mixed and air-dried to obtain coated seeds.

Next, the effects and usefulness of the compound of the present invention will be described with reference to examples. The compounds of the present invention are indicated by compound numbers listed in Table 1.

Test Example 1: Insecticidal effect test on Chinese diamondback moth (Plutella xylostella) On the leaves of pot-planted Chinese cabbage seedlings raised two weeks after sowing, an emulsion diluted with water (500 ppm) prepared according to Formulation Example 1 was applied with an air brush. A sufficient amount was sprayed using After the chemical solution was air-dried, 5 third instar larvae of diamondback moth were inoculated per pot and kept in a constant temperature room at 25°C. Five days after release, the larvae were examined for life and death and writhing, and the killing rate (%) was determined by regarding writhing larvae as dead. The test was conducted with one seedling in each group.

Insecticide rate (%) = (number of dead larvae/number of test larvae) x 100

As a result, compound numbers A-6, A-7, A-8, A-9, A-12, A-15, A-16, A-17, A-18, A-19, A-21, A Compounds -22, A-24 and A-28 gave 100% kill.

Test Example 2: Killing larvae test against tomato rust mite (Aculops lycopersici Masssee) A 430 ml capacity polyethylene cup containing water was placed on a lid with a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm and a notch with a width of about 5 mm was placed on the lid so as to form a strip-shaped filter paper piece, and the filter paper piece extended downward from the hole in the lid. The tip of the filter paper is immersed in the water in the cup. On the other hand, absorbent cotton is placed on the filter paper. Three leaf discs (1 cm x 1 cm) prepared from early leaflets were placed with the underside of the disc-shaped leaf facing up, and a small piece of leaf infested with tomato rust mite was inoculated on the disc-shaped leaf. . 24 hours after inoculation, the small pieces were removed, the cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and 2.0 ml per cup of a water-diluted emulsion (500 ppm) of the emulsion prepared according to Formulation Example 1 was added. It was sprayed using an airbrush. After spraying, it was kept in a constant temperature room at 25°C. 3 days after treatment, control rate is evaluated in 4 stages of 100 (control rate: 100%), 80 (same: 99-80%), 50 (same: 79-50%), 0 (same: less than 50%) Based on the results, the control rate was calculated using the following formula. The test was carried out using 1 cup for each section.

Control rate = (A x 100 + B x 80 + C x 50) / (A + B + C + D)

A: 100 discs, B: 80 discs, C: 50 discs, D: 0 discs

As a result, the compounds of compound numbers A-6, A-12, A-15, A-18, A-21, A-23 and A-27 exhibited a control rate of 100%.

Test Example 3: Density inhibition test against tomato rust mite (Aculops lycopersici Masssee) A 430 ml polyethylene cup filled with water was covered with a lid with a hole (approximately 5 mm in diameter) in the center. A circular filter paper with a diameter of 6.5 cm was cut with a width of about 5 mm, and the strip-shaped part hanging downward was inserted through the hole in the lid so as to be immersed in the water in the cup, and absorbent cotton was placed on the filter paper. In this way, three leaf discs (1 cm x 1 cm) made from small leaves in the early stages of tomato true leaf development were placed on the absorbent cotton in a state where the cup was constantly replenished with water. The discs were then inoculated with leaf pieces infested with Tomato rust mite. 24 hours after inoculation, the small pieces were removed, the cup was placed in an acrylic cylinder with a height of 50 cm and a diameter of 10 cm, and diluted with water (500 ppm) of the emulsion prepared according to Formulation Example 1, 2.0 ml per cup, It was sprayed using an airbrush. After spraying, it was kept in a constant temperature room at 25°C. 7 days after treatment, it was evaluated in four stages of 100 (density suppression rate: 100%), 80 (same: 99-80%), 50 (same: 79-50%), 0 (same: less than 50%). Based on the results, the density suppression rate was calculated using the following formula. The test was carried out using 1 cup for each section.

Density suppression rate = (A x 100 + B x 80 + C x 50) / (A + B + C + D)
A: 100 discs, B: 80 discs, C: 50 discs, D: 0 discs

As a result, the compounds of compound numbers A-6, A-9, A-16, A-18 and A-24 exhibited a control rate of 100%.

Claims (11)

the following formula (1),

[In the formula,
R ¹ represents a C _1-6 alkyl group or a C _1-6 haloalkyl group,
A ₁ , A ₂ , A ₃ , A ₄ and A ₅ each independently represent CR ² ,
R ² may be the same or different, hydrogen atom, halogen atom, C _1-6 alkyl group, C _1-6 haloalkyl group, C _3-8 cycloalkyl group, C _1-6 alkoxy group, C _3-6 alkenyloxy group, _C3-6 alkynyloxy group, _{C1-6 haloalkoxy} group, _C3-6 haloalkenyloxy group, C3-6 haloalkynyloxy group, _C1-6 alkylthio group, _C1-6 alkyl a sulfinyl group, a C _1-6 alkylsulfonyl group, a C _1-6 haloalkylthio group, a C _1-6 haloalkylsulfinyl group, a C _1-6 haloalkylsulfonyl group, a nitro group, or a cyano group,
R ³ is a hydrogen atom, a halogen atom, a C _1-6 alkyl group, a C _1-6 haloalkyl group, a C _3-8 cycloalkyl group, a C _1-6 alkylthio group, a C _1-6 alkylsulfinyl group, a C _{1- 6} alkylsulfonyl group, C _1-6 haloalkylthio group, C _1-6 haloalkylsulfinyl group, C _1-6 haloalkylsulfonyl group, nitro group or cyano group,
n is an integer from 0 to 2; ]
An N-cyanomethylimidazopyridine-2-carboxamide derivative, its N-oxide, or its salt, characterized by being represented by The N-cyanomethylimidazopyridine-2-carboxamide derivative, its N-oxide or its salt according to claim 1, wherein R ¹ represents a C _1-6 alkyl group. the following formula (1-1) or (1-2),

[wherein R ¹ , R ² , R ³ , A ₁ , A ₂ , A ₃ , A ₄ , A ₅ and n are as defined above. ]
A method for producing an N-cyanomethylimidazopyridine-2-carboxamide derivative represented by
A production method characterized by oxidizing an N-cyanomethylimidazopyridine-2-carboxamide derivative represented by formula (1-0). the following formula (1-0),

[Wherein, R ¹ , R ² , R ³ , A ₁ , A ₂ , A ₃ , A ₄ , A ₅ and n are as defined above, Y is a chlorine atom, a bromine atom, an iodine atom , represents a methanesulfonyloxy group or a trifluoromethanesulfonyloxy group]
A method for producing an N-cyanomethylimidazopyridine-2-carboxamide derivative represented by
A method characterized by reacting an imidazopyridine-2-carboxamide derivative represented by formula (1-3) with an acetonitrile derivative represented by YCH ₂ CN in the presence of a base in a solvent. 3. An agricultural and horticultural agent comprising the N-cyanomethylimidazopyridine-2-carboxamide derivative, its N-oxide or its salt according to claim 1 or 2. 3. An agricultural and horticultural acaricide comprising the N-cyanomethylimidazopyridine-2-carboxamide derivative, N-oxide thereof or salt thereof according to claim 1 or 2. 3. An agricultural and horticultural pest control agent comprising the N-cyanomethylimidazopyridine-2-carboxamide derivative, its N-oxide or its salt according to claim 1 or 2. 3. An agricultural and horticultural disease preventive agent comprising the N-cyanomethylimidazopyridine-2-carboxamide derivative, its N-oxide or its salt according to claim 2. A step of treating pests and/or their habitats and/or seeds and/or plant propagation material attacked by pests with the agricultural and horticultural agent according to claim 5, characterized in that A method for controlling plant pests. A plant harmfulness characterized by comprising a step of treating a place where useful crops are to be grown, a place where useful crops are grown, or growing crops with the agricultural and horticultural agent according to claim 5. A method for controlling organisms. A method for preparing an agrochemical composition, comprising the step of mixing the agricultural and horticultural agent according to claim 5 with an extender and/or a surfactant.