WO2011074677A1

WO2011074677A1 - Imidazopyrimidine derivative or salt thereof, and noxious organism control agent comprising same

Info

Publication number: WO2011074677A1
Application number: PCT/JP2010/072802
Authority: WO
Inventors: 一浩山元; 寿彦植木; 智裕岡本; 省吾渥美; 和久桐山; 幸太郎吉田; 直梅本; 哲也小玉
Original assignee: 石原産業株式会社
Priority date: 2009-12-18
Filing date: 2010-12-17
Publication date: 2011-06-23
Also published as: JP2011144169A

Abstract

Disclosed is a novel noxious organism control agent. Specifically disclosed is a noxious organism control agent comprising an imidazopyrimidine derivative represented by formula (I) [wherein Cy represents an aryl group substituted by X or a heteroary group substituted by X; and R1 represents an unsubstituted alkyl group, an alkyl group substituted by A, an unsubstituted cycloalkyl group, a cycloalkyl group substituted by Q, an unsubstituted alkenyl group, an alkenyl group substituted by A, an unsubstituted alkynyl group, an alkynyl group substituted by A, a halogen atom, a cyano group, an aryl group, an unsubstituted heterocyclic group, a heterocyclic group substituted by an alkyl group, CH=NOR2, CH=NNR4R5, COR2, COOR2, OR2, S(O)nR3, NR4R5 or CONR4R5] or a salt thereof as an active ingredient.

Description

Imidazopyrimidine derivatives or salts thereof, and pest control agents containing them

The present invention relates to a novel pest control agent containing an imidazopyrimidine derivative or a salt thereof as an active ingredient.

Patent Document 1 describes an imidazopyrimidine derivative that can be used as an organic electroluminescence device. Patent Document 2 describes that an imidazopyrimidine derivative can be used as a medicine. However, these documents do not specifically describe the imidazopyrimidine derivatives represented by the following general formula (I), and do not describe the use of the imidazopyrimidine derivatives as pest control agents.

Patent No. 4,025,468 US Pat. No. 5,037,980

Many pest control agents have been used for many years, but many have various problems such as insufficient efficacy, pests gaining resistance, and their use is restricted. Therefore, development of a new pest control agent with few such disadvantages, for example, a pest control agent capable of controlling various pests that are problematic in the field of agriculture and horticulture and pests parasitic on animals is desired.
An object of the present invention is to provide a pest control agent that has a high control effect on pests and has high safety for mammals and the like when used.

The present inventors have made various studies on imidazopyrimidine derivatives in order to find better pest control agents. As a result, the imidazopyrimidine derivative represented by the following formula (I) has an extremely high control effect against pests at a low dose, and is safe for crops, pest natural enemies or mammals. The present invention was completed.

That is, the present invention has the formula (I):

Wherein Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or Alkenyl substituted with A, unsubstituted or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² , COOR ² , alkoxyvinyl, S (O) _m [N (CN)] R ³ or C (R ³ ) = NNG ¹ G ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; Q is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, Alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl , alkoxyalkyl, acetyl, benzyl, or aryl; R ³ is alkyl, unsubstituted or aryl or haloalkyl substituted with a halogen atom; R ⁴ is a hydrogen atom or alkyl; R ⁵ is water Atom, alkyl, cycloalkyl, ^{^{haloalkyl, COR 2, COOR 2, S}} (O) n R 3, CH 2 CH 2 be OR ² or CH ₂ CN; G ¹ and G ² each independently represent a hydrogen atom, an alkyl or COOR ³ , G ¹ and G ² may be bonded to each other to form a ring with the adjacent nitrogen atom; n is an integer of 0 to 2; m is an integer of 0 or 1. ] The pest control agent which uses the imidazopyrimidine derivative represented by these, or its salt as an active ingredient, and the method of controlling a pest by applying them.
The present invention also relates to the imidazopyrimidine derivative of the above formula (I) or a salt thereof.

The pest control agent comprising the imidazopyrimidine derivative of the formula (I) or a salt thereof as an active ingredient has a very high control effect against pests at a low dose.

The substituents in Cy and R ¹ in formula (I) are described in detail below.
The number of substitutions for X, A and Q may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different. Further, the substitution positions of X, A and Q may be any positions.

Examples of the halogen atom include fluorine, chlorine, bromine or iodine atoms. The number of halogen atoms as a substituent may be 1 or 2 or more, and in the case of 2 or more, each halogen atom may be the same or different. Further, the halogen atom may be substituted at any position.
Alkyl may be linear or branched, and examples thereof include C _1-6 ones such as methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, pentyl and hexyl.
Examples of cycloalkyl include C _3-6 such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

The alkenyl may be linear or branched, for example C _2-6 such as vinyl, 1-propenyl, allyl, isopropenyl, 1-butenyl, 1,3-butadienyl, 1-hexenyl. Etc.
The alkynyl may be linear or branched, for example, a C such as ethynyl, 2-butynyl, 2-pentynyl, 3-methyl-1-butynyl, 2-penten-4-ynyl, 3-hexynyl. _{2-6 and} the like.
Examples of the aryl include C _6-10 such as phenyl and naphthyl.

The heteroaryl may be a monocyclic heteroaryl or a condensed heteroaryl, and may contain 1 to 4 atoms selected from the group consisting of O, S and N. Specific examples thereof include 5-membered heteroaryl such as furyl, thienyl, pyrrolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, pyrazolyl, triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl; pyridyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl Benzofuranyl, isobenzofuranyl, benzothienyl, isobenzothienyl, indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, quinolyl, isoquinolyl, phthalazinyl, quinazolinyl, quinoxalinyl, imidazopyridyl And 8- to 10-membered condensed heteroaryl such as naphthyridinyl and pteridinyl.

The heterocyclic group may be either a monocyclic heterocyclic group or a condensed heterocyclic group, and may contain 1 to 4 atoms of at least one selected from the group consisting of O, S and N. Specific examples thereof include 3-membered heterocyclic groups such as oxiranyl; furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, dioxolanyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, imidazolyl, imidazolinyl, imidazolidinyl, pyrazolyl, pyrazolinyl, pyrazolidinyl, pyrazolidinyl , Triazolyl, oxadiazolyl, thiadiazolyl, tetrazolyl and the like; 6-membered heterocyclic groups such as pyranyl, pyridyl, piperidinyl, dioxanyl, oxazinyl, morpholinyl, thiazinyl, pyridazinyl, pyrimidinyl, pyrazinyl, piperazinyl, triazinyl; benzofuranyl, iso Benzofuranyl, dihydrobenzofuranyl, dihydroisobenzofuranyl, benzothienyl, isobenzothieni , Dihydrobenzothienyl, dihydroisobenzothienyl, tetrahydrobenzothienyl, indolyl, isoindolyl, benzoxazolyl, benzothiazolyl, indazolyl, benzimidazolyl, benzodioxolanyl, benzodioxanyl, chromenyl, chromanyl, isochromanyl, chromonyl, chromanonyl, 8 ~ such as quinolyl, isoquinolyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl, indolizinyl, quinolidinyl, imidazopyridyl, naphthyridinyl, pteridinyl, dihydrobenzoxazinyl, dihydrobenzoxazolinonyl, dihydrobenzoxazinonyl, benzothioxanyl Examples thereof include a 10-membered condensed heterocyclic group.

Examples of the salt of the imidazopyrimidine derivative of the formula (I) include any salt that is acceptable in the art, for example, ammonium salts such as dimethylammonium salt and triethylammonium salt; Examples thereof include inorganic acid salts such as chlorate, sulfate and nitrate; organic acid salts such as acetate and methanesulfonate.

In the imidazopyrimidine derivative of the formula (I), there may be isomers such as optical isomers and geometric isomers, but the present invention includes both isomers and isomer mixtures. In the present invention, unless otherwise specified, isomers are described as a mixture. The present invention also includes various isomers other than those described above within the scope of technical common sense in the technical field. Further, depending on the type of isomer, there may be a chemical structure different from that of formula (I). However, since those skilled in the art can fully recognize that they are related to isomers, they are within the scope of the present invention. Obviously.

The imidazopyrimidine derivative of the formula (I) or a salt thereof (hereinafter abbreviated as the compound of the present invention) can be produced according to the following production methods [1] to [12] and usual salt production methods. The reaction flow will be described in detail below for each production method.
Manufacturing method [1]

Substituted PRODUCTION PROCESS [1], R ^1a is an alkyl substituted with an unsubstituted or A ^1, is substituted by an unsubstituted or Q ¹ cycloalkyl, alkenyl substituted with an unsubstituted or A ^1, unsubstituted or A ¹ Alkynyl, aryl or unsubstituted or alkyl-substituted heterocyclic group; each R ⁶ is independently alkyl; A ¹ is a halogen atom, OR ^2a , S (O) _n R ³ , NR ⁴ R ^5a, cyano, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ^2a, NHNR ⁴ be R ^5a or CH (CN) _2; ^{Q 1} is a halogen ^{atom, oR 2a, S (O)} n R 3, NR 4 R ^5a, cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ^2a, be NHNR ⁴ R ^5a or CH (CN) _2; R ^2a is a hydrogen atom, an alkyl, alkenyl, alkynyl, Roarukiru, alkoxyalkyl, acetyl, benzyl, or aryl; R ^5a is a hydrogen atom, alkyl, cycloalkyl, haloalkyl, COR ^2a, COOR ^2a or _{^{S (O) n R 3;}} R 3, R 4, Cy and n is as described above. Salts of formula (IV) include any salt that is acceptable in the art, for example, inorganic acid salts such as hydrochlorides and sulfates; acetates and methanesulfonates, etc. Organic acid salt; and the like.

This reaction can be performed in the presence of a base, if necessary. Examples of the base include carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; organic bases such as triethylamine and pyridine; One or more types are appropriately selected from the above.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, carboxylic acids such as acetic acid and propionic acid; alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene. Aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin, petroleum benzine; such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane Ethers; esters such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propiononitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; Dimethyl sulfo Sulfoxides such as sid; sulfones such as sulfolane; phosphoric amides such as hexamethylphosphoramide; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and These mixed solvents can be mentioned, among which carboxylic acids are desirable. The reaction temperature is usually 50 to 150 ° C., desirably 80 to 120 ° C. The reaction time is usually 0.5 to 100 hours.
Manufacturing method [2]

In the production process [2], each R ⁷ is independently alkyl, and Cy is as described above.

This reaction can usually be performed in the presence of a base and a solvent. Examples of the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide. Alkali metal alkoxides such as potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; acetates such as sodium acetate and potassium acetate; triethylamine; One or more types are appropriately selected from organic bases such as pyridine. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [1]. The reaction temperature is usually 60 to 200 ° C, preferably 80 to 120 ° C. The reaction time is usually 0.1 to 10 hours.

Manufacturing method [3]

In the production process [3], na is an integer of 1 or 2, and R ⁷ and Cy are as described above.

Examples of the oxidizing agent include hydrogen peroxide, peracetic acid, m-chloroperbenzoic acid, and the like. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include carboxylic acids such as acetic acid and propionic acid; diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane, and the like. Ethers; ketones such as acetone and methyl ethyl ketone; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. The reaction temperature is usually −10 ° C. to the reflux temperature of the reaction mixture, preferably 0 to 40 ° C. The reaction time is usually 1 to 24 hours.
Manufacturing method [4]

Substituted in production process [4], R ^1b is an alkyl substituted with an unsubstituted or A ^1, is substituted by an unsubstituted or Q ¹ cycloalkyl, alkenyl substituted with an unsubstituted or A ^1, unsubstituted or A ¹ Alkynyl, halogen atom, cyano, aryl, unsubstituted or alkyl-substituted heterocyclic group, SR ³ , OR ^2a or NR ⁴ R ^5a ; R ^2a , R ^5a , R ³ , R ⁴ , R ⁷ , A ¹ , Q ¹ , Cy and na are as described above.

Examples of the nucleophile include alkali metal alkoxides such as sodium methoxide and sodium ethoxide; alkali metal thiolates such as sodium thiomethoxide; general formula HNR ⁴ R ^5a [formula such as methylamine, dimethylamine and piperidine Wherein R ⁴ and R ^5a are as described above]; alkali metal cyanides such as sodium cyanide and potassium cyanide; organometallics such as methylmagnesium bromide, ethylmagnesium bromide and phenylmagnesium bromide Reagents; fluorinating agents such as potassium fluoride, cesium fluoride, tetrabutylammonium fluoride; and the like.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane and petroleum ether Aliphatic hydrocarbons such as ligroin and petroleum benzine; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane; methyl acetate, ethyl acetate, etc. Nitriles such as acetonitrile and propiononitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; Such a mixed solvent thereof. The reaction temperature is usually −100 to 50 ° C., desirably −70 to 30 ° C. The reaction time is usually 1 minute to 48 hours.
Manufacturing method [5]

In production method [5], Y is a halogen atom; M is B (OH) ₂ , B (OR ⁸ ) ₂ , MgY ¹ or ZnY ¹ ; R ⁸ is each independently alkyl; Y ¹ is chlorine An atom, a bromine atom or an iodine atom; Cy is as described above. Examples of the halogen atom for Y include fluorine, chlorine, bromine and iodine atoms. In B (OR ⁸ ) ₂ , R ⁸ may be bonded to each other to form a ring containing a boron atom.

This reaction can be performed in the presence of a base, if necessary. Examples of the base include metal hydroxides such as sodium hydroxide, potassium hydroxide and calcium hydroxide; carbonates such as sodium carbonate, potassium carbonate, cesium carbonate and calcium carbonate; sodium bicarbonate and potassium bicarbonate. 1 type or 2 types or more are appropriately selected from the following: metal bicarbonates; metal fluorides such as cesium fluoride and potassium fluoride; organic bases such as triethylamine, pyridine and 4- (N, N-dimethylamino) pyridine; Selected.

This reaction can be carried out in the presence of a metal catalyst, if necessary. Examples of the metal catalyst include a copper compound, a tin compound, and a palladium compound. Among these, a palladium compound is preferable. Moreover, when using a metal catalyst, a co-catalyst is used together as needed. Examples of the cocatalyst include alkali metal halides such as lithium chloride. Examples of the combination of the metal catalyst and the promoter include a palladium compound such as tetrakis (triphenylphosphine) palladium and lithium chloride.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, water; alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; pentane, hexane, heptane, Aliphatic hydrocarbons such as petroleum ether, ligroin, petroleum benzine; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane; acetonitrile, propiononitrile Nitriles such as N; N-dimethylformamide, N, N-dimethylacetamide, acid amides such as N-methylpyrrolidinone; halogenated carbonization such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane hydrogen ; And the like mixed solvents thereof. The reaction temperature is usually 40 ° C. to 150 ° C., desirably 60 to 120 ° C. The reaction time is usually 10 to 96 hours. When the compound of the formula (VII) is a boron compound, it is commercially available or can be synthesized by a conventional method. For example, Cy-B (OH) ₂ can be synthesized by reacting a halide such as CyI, CyBr or CyCl with trimethyl borate in the presence of a base such as tert-butyllithium.
Manufacturing method [6]

Substituted PRODUCTION PROCESS [6], R ^1c is alkyl substituted with an unsubstituted or A ^1, is substituted by an unsubstituted or Q ¹ cycloalkyl, alkenyl substituted with an unsubstituted or A ^1, unsubstituted or A ¹ Alkynyl, cyano, aryl, unsubstituted or alkyl-substituted heterocyclic group, OR ^2a , SR ³ or NR ⁴ R ^5a ; R ^2a , R ³ , R ⁴ , R ^5a , A ¹ , Q ¹ , Y and Cy are as described above.

Examples of the nucleophilic reagent include those other than the fluorinating agent in the nucleophilic reagent used in the above production method [4].

This reaction can be performed in the presence of a base, if necessary. Examples of the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; sodium methoxide, sodium ethoxide and potassium tertiary butoxide. 1 type or 2 types or more are suitably selected from alkali metal alkoxides; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; organic bases such as triethylamine and pyridine; The

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [4]. The reaction temperature is usually −30 ° C. to the reflux temperature of the reaction mixture, preferably 20 to 120 ° C. The reaction time is usually 10 to 96 hours.
Manufacturing method [7]

PRODUCTION PROCESS [7], Cy ¹ is an heteroaryl substituted with aryl or Y ¹ substituted with Y ^1; Cy ² is heteroaryl substituted with aryl or X ¹ substituted with X ^1; X ¹ is alkoxyvinyl; M ¹ is B (OH) ₂ , B (OR ⁸ ) ₂ , SnR ⁸ ₃ , MgY ¹ , ZnY ¹ or Li; R ¹ , R ⁸ and Y ¹ are as described above It is. Aryl or heteroaryl in Cy ¹ and Cy ² is optionally substituted at each ^{X a.} The substitution number of X ^a may be at each one or more, and if more, may be the same or different. The substitution position of X ^a may each be any positions. X ^a is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, chlorine, haloalkyl, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) nR ³ , OR ² or CO ₂ R ² .

This reaction can be performed in the presence of a base, if necessary. Examples of the base include those similar to the above production method [5].

This reaction can be performed in the presence of a metal catalyst, if necessary. Examples of the metal catalyst include those similar to the above production method [5], and among them, a palladium compound is preferable.
Moreover, when using a metal catalyst, a co-catalyst is used together as needed. Examples of the cocatalyst include those similar to the above production method [5]. Examples of the combination of the metal catalyst and the promoter include a palladium compound such as tetrakis (triphenylphosphine) palladium and lithium chloride.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [5]. The reaction temperature is usually from 50 ° C. to the reflux temperature of the reaction mixture, preferably from 80 ° C. to the reflux temperature of the reaction mixture. The reaction time is usually 1 to 96 hours.
Manufacturing method [8]

In production method [8], Cy ³ is aryl substituted with acetyl or heteroaryl substituted with acetyl; Cy ² and R ¹ are as described above. Aryl or heteroaryl in cy ³ may be substituted with X ^a. The substitution number of X ^a may be one or more, and if more, may be the same or different. The substitution position of X ^a may be any positions. ^Xa is as described above.

Examples of the acid include hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, acetic acid, p-toluenesulfonic acid and the like. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, water; alcohols such as methanol, ethanol, propanol and butanol; diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2 Ethers such as dimethoxyethane; esters such as methyl acetate and ethyl acetate; ketones such as acetone and methyl ethyl ketone; nitriles such as acetonitrile and propiononitrile; N, N-dimethylformamide, N, N -Acid amides such as dimethylacetamide and N-methylpyrrolidinone; and mixed solvents thereof. The reaction temperature is usually from room temperature to the reflux temperature of the reaction mixture, preferably from room temperature to 70 ° C. The reaction time is usually from 1 to 24 hours.
Manufacturing method [9]

PRODUCTION PROCESS [9], Cy ⁴ is an C (CH ₃₎ = ^NNG 1 is substituted with ^{G 2} aryl or C (CH ₃₎ = ^NNG heteroaryl substituted with ^{^{^{1 G 2; Cy 3, R}}} 1, G ¹ and G ² are as described above. Aryl or heteroaryl in cy ⁴ may be substituted with X ^a. The substitution number of X ^a may be one or more, and if more, may be the same or different. The substitution position of X ^a may be any positions. ^Xa is as described above. Salts of formula (XVI) include any salt that is acceptable in the art, for example, inorganic acid salts such as hydrochlorides, sulfates; acetates, methanesulfonates, etc. Organic acid salt; and the like.

This reaction can be performed in the presence of a base, if necessary. Examples of the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide. Alkali metal alkoxides such as potassium tertiary butoxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; amines such as monomethylamine, dimethylamine and triethylamine One or two or more kinds are suitably selected from pyridines such as pyridine and 4-dimethylaminopyridine;

This reaction can be carried out in the presence of a catalytic amount of an acid, if necessary. Examples of the acid include hydrochloric acid, sulfuric acid, para-toluenesulfonic acid and the like.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, water; alcohols such as methanol, ethanol, propanol and butanol; aromatic hydrocarbons such as benzene, toluene and xylene; hexane, heptane and petroleum Aliphatic hydrocarbons such as ether, ligroin and cyclohexane; ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane and 1,2-dimethoxyethane; methyl acetate and ethyl acetate Nitriles such as acetonitrile and propiononitrile; acid amides such as N, N-dimethylformamide, N, N-dimethylacetamide and N-methylpyrrolidinone; sulfoxides such as dimethyl sulfoxide; sulfolane Una sulfones; phosphoric acid amides such as hexamethylphosphoramide; and and mixtures of these solvents. In addition, amines or pyridines can also be used as a solvent among the above bases that can be used in the production method [9]. The reaction temperature is usually from room temperature to the reflux temperature of the reaction mixture, preferably from 50 ° C. to the reflux temperature of the reaction mixture. The reaction time is usually 1 to 24 hours.
Manufacturing method [10]

PRODUCTION PROCESS [10], Cy ⁵ is heteroaryl substituted with aryl or SR ³ substituted with SR ^3; Cy ⁶ is S (O) substituted with NAR ³ aryl or S (O) NAR ³ Substituted heteroaryl; R ¹ , R ³ and na are as described above. The aryl or heteroaryl in Cy ⁵ and Cy ⁶ may each be substituted with ^Xb . The number of substitutions of ^Xb may be 1 or 2 or more, and in the case of 2 or more, they may be the same or different. Further, the substitution position of ^Xb may be any position. X ^b is alkyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) ₂ R ³ , OR ² or CO ₂ R ² .

Examples of the oxidizing agent include those similar to the above production method [3]. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [3]. The reaction temperature is usually −10 ° C. to the reflux temperature of the reaction mixture, preferably −10 to 50 ° C. The reaction time is usually 1 to 24 hours.
Manufacturing method [11]

PRODUCTION PROCESS [11], Cy ⁷ is an S [N (CN)] ^{R 3} substituted aryl or S [N (CN)] heteroaryl substituted with ^{^R ^3;} Cy 5, ^R ¹ and ^{R 3} Is as described above. The aryl or heteroaryl in Cy ⁷ may be substituted with ^Xb . The number of substitution of ^Xb may be 1 or 2 or more, and when 2 or more, they may be the same or different. Further, the position of substitution of ^Xb may be any position. ^Xb is as described above.

This reaction can usually be performed in the presence of an oxidizing agent. Examples of the oxidizing agent include iodobenzene diacetate and hypochlorite.

This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, water; tertiary alcohols such as tert-butyl alcohol; diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1, Ethers such as 2-dimethoxyethane; nitriles such as acetonitrile and propiononitrile; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. Can be mentioned. The reaction temperature is usually −40 to 80 ° C., desirably −10 to 50 ° C. The reaction time is usually 0.5 to 25 hours.
Manufacturing method [12]

PRODUCTION PROCESS [12], Cy ⁸ is an S (O) [N (CN )] R 3 substituted aryl or S (O) [N (CN )] heteroaryl substituted with ^{R 3;} Cy ⁷ , R ¹ and R ³ are as described above. The aryl or heteroaryl in Cy ⁸ may be substituted with ^Xb . The number of substitution of ^Xb may be 1 or 2 or more, and when 2 or more, they may be the same or different. Further, the substitution position of ^Xb may be any position. ^Xb is as described above.

This reaction can usually be performed in the presence of a base. Examples of the base include metal hydroxides such as sodium hydroxide and potassium hydroxide; carbonates such as sodium carbonate and potassium carbonate; bicarbonates such as sodium bicarbonate and potassium bicarbonate; Two or more kinds are appropriately selected.

Examples of the oxidizing agent include m-chloroperbenzoic acid, ruthenium tetroxide, permanganate and the like. This reaction can usually be performed in the presence of a solvent. Examples of the solvent include water; alcohols such as methanol, ethanol, propanol and butanol; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride and 1,2-dichloroethane; and mixed solvents thereof. Can be mentioned. The reaction temperature is usually −10 to 50 ° C., desirably −10 to 30 ° C. The reaction time is usually 0.5 to 24 hours.

The compound of formula (II) used in the production method [1] can be produced according to the following production method [A].
Manufacturing method [A]

In the production process [A], R ^1a , R ⁶ , R ⁷ and Cy are as described above.

This reaction can be performed in the presence of a solvent, if necessary. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include the same as in the above production method [2]. The reaction temperature is usually 80 to 200 ° C., preferably 100 to 150 ° C. The reaction time is usually 6 to 48 hours. After the completion of the reaction of the production method [A], the reaction of the production method [1] can be continued without isolating the compound of the formula (II).

The compound of the formula (III) used in the production method [1] can be produced according to the following production method [B] or production method [C].
Manufacturing method [B]

In the production process [B], R ^1a , R ⁷ and Cy are as described above.

This reaction can usually be performed in the presence of a base and a solvent. Examples of the base include metal hydrides such as sodium hydride and potassium hydride; metal hydroxides such as sodium hydroxide and potassium hydroxide; alkali metals such as sodium and potassium; sodium methoxide and sodium ethoxide 1 type, or 2 or more types are suitably selected from alkali metal alkoxides such as potassium tertiary butoxide; The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; aliphatic hydrocarbons such as pentane, hexane, heptane, petroleum ether, ligroin and petroleum benzine. Ethers such as diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2-dimethoxyethane; like N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidinone Sulfoxides such as dimethyl sulfoxide; sulfones such as sulfolane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, 1,2-dichloroethane; and mixed solvents thereof. But ate Kind is desirable. The reaction temperature is usually 0 to 70 ° C., preferably 0 to 50 ° C. The reaction time is usually 5 minutes to 24 hours. After completion of the production method [B], the reaction of the production method [1] can be carried out without isolating the compound of the formula (III).
Manufacturing method [C]

In the production process [C], R ^1a , R ⁷ and Cy are as described above.

This reaction can usually be performed in the presence of a base and a solvent. Examples of the base include those similar to the above production method [B]. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [B], and ethers are particularly preferable. The reaction temperature is usually 0 to 70 ° C., preferably 0 to 50 ° C. The reaction time is usually 5 minutes to 80 hours. After completion of the production process [C], the reaction of the production process [1] can be continued without isolating the compound of the formula (III).

The compound of the formula (XI) is commercially available or can be produced by a conventional method. For example, as shown in Synthesis Example 5 (1) below, it can be produced by an esterification reaction starting from a carboxylic acid derivative.

The compound of the formula (III) produced according to the above production method [B] or the production method [C] can be used for the reaction of the production method [1] after further carrying out a substituent conversion reaction in Cy. For example, a compound of the formula (III-2) which is a sulfoxy derivative or a sulfone derivative can be produced from a compound of the formula (III-1) according to the production method [C-1] shown below. It can be used as a raw material for the reaction.
Manufacturing method [C-1]

In the production process [C-1], R ^1a , Cy ⁵ and Cy ⁶ are as described above.

Examples of the oxidizing agent include those similar to the above production method [3]. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [3]. The reaction temperature is usually from −10 ° C. to the reflux temperature of the reaction mixture, preferably from −10 to 50 ° C. The reaction time is usually 1 to 24 hours. After completion of the production process [C-1], the reaction of the production process [1] can be carried out without isolating the compound of the formula (III-2).

The compound of the formula (V) used in the production method [2] can be produced according to the following production method [D].
Manufacturing method [D]

In the production method [D], R ⁷ , Y and Cy are as described above.

This reaction can usually be performed in the presence of a base and a solvent. Examples of the base include those similar to the above production method [B]. The solvent is not particularly limited as long as the reaction proceeds, and examples thereof include those similar to the above production method [2]. The reaction temperature is usually 0 to 100 ° C., preferably 10 to 50 ° C. The reaction time is usually 6 to 48 hours.

The compound of the formula (VI) used in the production method [5] can be produced according to the following production method [E].
Manufacturing method [E]

In the production method [E], Y is as described above.

The production method [E] is classified according to the type of Y in formula (VI). That is, (a) when Y in formula (VI) is a chlorine atom or bromine atom, reacting a compound of formula (XIV) with a chlorinating agent or brominating agent; (b) Y in formula (VI) is In the case of a fluorine atom, reacting the compound of formula (VI) obtained in (a) above with a fluorinating agent; or (c) one Y in formula (VI) is an iodine atom and the other is a chlorine atom In the case of a bromine atom or an iodine atom, it can be produced by reacting the compound of the formula (VI) obtained in (a) with NH ₃ and then reacting with diiodomethane in the presence of a diazotizing agent. The production methods in the cases (a) to (c) will be described in detail below.

(A) Examples of the chlorinating agent include phosphorus oxychloride, phosphorus trichloride, and phosphorus pentachloride. Examples of the brominating agent include phosphorus oxybromide, phosphorus tribromide, and phosphorus pentabromide. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as toluene and xylene; nitriles such as acetonitrile and propiononitrile; sulfones such as sulfolane; halogen such as dichloromethane Hydrocarbons; and mixed solvents thereof. An excessive amount of chlorinating agent or brominating agent may be used as a solvent. The reaction temperature is usually 0 ° C. to the reflux temperature of the reaction mixture, desirably 20 to 100 ° C. The reaction time is usually 1 to 24 hours.

(B) Examples of the fluorinating agent include alkali metal fluorides such as potassium fluoride; antimony pentafluoride; diethylaminosulfur trifluoride; This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; nitriles such as acetonitrile and propiononitrile; ethers such as crown ether; N, Examples thereof include acid amides such as N-dimethylformamide and N, N-dimethylacetamide; sulfones such as sulfolane; and mixed solvents thereof. When sulfolane or N, N-dimethylformamide is used as a solvent, it is advantageous to use toluene as a co-solvent to assist dehydration of the fluorinating agent. The reaction temperature is usually about 15 ° C. to the reflux temperature of the reaction mixture, desirably 40 ° C. to the reflux temperature of the reaction mixture. The reaction time is 1 to 24 hours.

(C) The reaction with NH ₃ can usually be carried out in the presence of a base, but it is desirable to use an excess amount of NH ₃ as the base. This reaction can usually be performed in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, aromatic hydrocarbons such as benzene, toluene and xylene; diethyl ether, diisopropyl ether, dibutyl ether, tetrahydrofuran, 1,4-dioxane, 1,2- And ethers such as dimethoxyethane; halogenated hydrocarbons such as chloroform, dichloromethane, carbon tetrachloride, and 1,2-dichloroethane; and mixed solvents thereof. The reaction temperature is usually from 20 ° C. to the reflux temperature of the reaction mixture, preferably from 40 ° C. to the reflux temperature of the reaction mixture. The reaction time is usually 1 to 24 hours.

Examples of diazotizing agents include alkyl esters of nitrous acid, among which isopentyl nitrite is preferable. The reaction with diiodomethane can usually be carried out in the presence of a solvent. The solvent is not particularly limited as long as the reaction proceeds. For example, when an alkyl ester of nitrous acid is used as the diazotizing agent, it can be used as a cosolvent with diiodomethane. The reaction temperature is usually −30 ° C. to 100 ° C., desirably −10 to 80 ° C., and the reaction time is usually 1 to 48 hours. Each reaction of (c) can be carried out continuously in one container without isolation and purification of the intermediate product.

The desirable mode of the pest control agent containing the compound of the present invention is described below. The pest control agent containing the compound of the present invention includes, for example, various pest control agents that are problematic in the field of agriculture and horticulture, that is, agricultural and horticultural pest control agents, and pest control agents that parasitize animals, that is, animal parasitics. It is particularly useful as a biocontrol agent.

As the agricultural and horticultural pest control agent, for example, it is useful as an insecticide, acaricide, nematicide or soil insecticide, specifically, a spider mite, a spider mite, a spider mite, a spider mite, an apple spider mite, Plant parasitic mites such as mite dust mites, citrus mites, mites, etc .; aphids such as peach aphids, cotton aphids, etc .; diamond moths, weevil, scallops, codling moths, ball worms, tobacco bad worms, maiiga, kobinomeiga, chanococa Agriculture such as spider anemone, Colorado potato beetle, cucumber potato beetle, ball weevil, leafhoppers, leafhoppers, scale insects, stink bugs, whitefly, thrips, grasshoppers, fly flies, scarab beetles, Tamanaga, Kaburayaga, ants Pests; Plant parasitic nematodes such as root-knot nematodes, cyst nematodes, papaver nematodes, rice scallop nematodes, strawberry nematodes, pinewood nematodes; gastropods such as slugs and maimai; Soil pests such as mosquitoes, hygiene pests such as house dust mites, cockroaches, house flies, mosquitoes, etc .; cereal storage pests such as bark moths, azuki beetles, mosquito moths, bark beetles; It is effective for controlling clothes, house pests such as termites, and indoor dust mites such as white mite, white leopard mite, and southern mite. The agricultural and horticultural pest control agent containing the compound of the present invention is particularly effective for controlling plant parasitic mites, agricultural pests, plant parasitic nematodes and the like. Among them, it is useful as an insecticide or an acaricide because it shows a further excellent effect in controlling plant parasitic mites and agricultural pests. Moreover, the agricultural and horticultural pest control agent containing the compound of the present invention is also effective in controlling various resistant pests against drugs such as organic phosphorus agents, carbamate agents, synthetic pyrethroid agents, and neonicotinoid agents. Furthermore, since the compound of the present invention has excellent osmotic transfer properties, soil harmful insects, mites, nematodes by treating agricultural and horticultural pesticides containing the compound of the present invention on the soil It is possible to control pests on the foliage at the same time as the control of gastropods and isopods.

As another desirable aspect of the pest control agent containing the compound of the present invention, the above-mentioned plant parasitic mites, agricultural pests, plant parasitic nematodes, gastropods, soil pests and the like are comprehensively controlled. Examples include horticultural pest control agents.

The agricultural and horticultural pest control agent containing the compound of the present invention is usually a powder, granule, granule wettable powder, wettable powder, aqueous suspension, by mixing the compound with various agricultural adjuvants, It is used in various forms such as oily suspensions, granular aqueous solvents, aqueous solvents, emulsions, solutions, pastes, aerosols, microdispersions, etc. Any formulation used in the art can be used. Adjuvants used in the formulation include solid carriers such as diatomaceous earth, slaked lime, calcium carbonate, talc, white carbon, kaolin, bentonite, kaolinite, sericite, clay, sodium carbonate, sodium bicarbonate, sodium sulfate, zeolite, starch; water, Solvents such as toluene, xylene, solvent naphtha, dioxane, acetone, isophorone, methyl isobutyl ketone, chlorobenzene, cyclohexane, dimethyl sulfoxide, N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-2-pyrrolidone, alcohol Fatty acid salts, benzoates, alkylsulfosuccinates, dialkylsulfosuccinates, polycarboxylates, alkyl sulfates, alkyl sulfates, alkylaryl sulfates, alkyl diglycol ether sulfates, al Sulfuric acid ester salt, alkyl sulfonate, alkyl aryl sulfonate, aryl sulfonate, lignin sulfonate, alkyl diphenyl ether disulfonate, polystyrene sulfonate, alkyl phosphate ester salt, alkyl aryl phosphate, Styryl aryl phosphate, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl aryl ether sulfate, polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl aryl phosphate Anionic surfactants such as ester salts and naphthalenesulfonate formaldehyde condensates; sorbitan fatty acid esters, glycerin fatty acid esters, fatty acid polyglycerides , Fatty acid alcohol polyglycol ether, acetylene glycol, acetylene alcohol, oxyalkylene block polymer, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene glycol alkyl ether, polyethylene glycol, polyoxy Nonionic surfactants such as ethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycerin fatty acid ester, polyoxyethylene hydrogenated castor oil, polyoxypropylene fatty acid ester; olive oil, kapok oil, castor oil, palm oil , Coconut oil, coconut oil, sesame oil, corn oil, rice bran oil, peanut oil, cottonseed oil, soybean oil, rapeseed oil, linseed , Tung oil, vegetable oil or mineral oil such as liquid paraffin; and the like. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the art. For example, a bulking agent, a thickening agent, an anti-settling agent, an antifreezing agent, a dispersion stabilizer, a phytotoxicity reduction. Various commonly used adjuvants such as agents, antifungal agents and the like can also be used. The compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is 0.001: 99.999 to 95: 5, preferably 0.005: 99.995 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

Application of the agricultural and horticultural pest control agent containing the compound of the present invention cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, type of pests and occurrence, etc., but generally 0.05 to 800,000 ppm The active ingredient concentration is preferably 0.5 to 500,000 ppm, and the application amount per unit area is 0.05 to 50,000 g, preferably 1 to 30,000 g of the compound of the present invention per hectare. The present invention also includes a method for controlling pests by such an application method, particularly a method for controlling plant parasitic mites, agricultural pests, and plant parasitic nematodes.

The application of various preparations or dilutions of agricultural and horticultural pesticides containing the compound of the present invention is usually performed by a commonly used application method, that is, spraying (for example, spraying, misting, atomizing). ), Dusting, water surface application, etc.), soil application (mixing, irrigation, etc.), surface application (application, powder coating, coating, etc.), immersion poison bait, etc. It is also possible to feed livestock with the above-mentioned active ingredient mixed with feed to inhibit the occurrence and growth of harmful insects, particularly harmful insects, in the excreta. It can also be applied by the so-called ultra-low volume application method. In this method, it is possible to contain 100% of the active ingredient.

In addition, the agricultural and horticultural pest control agent containing the compound of the present invention can be mixed or used in combination with other agricultural chemicals, fertilizers, safeners, etc. There is. Other pesticides include herbicides, insecticides, acaricides, nematicides, soil insecticides, fungicides, antiviral agents, attractants, antibiotics, plant hormones, plant growth regulators, etc. It is done. In particular, a mixed pest control composition in which the compound of the present invention and one or more active compound compounds of other agricultural chemicals are used in combination or in combination is preferred in terms of application range, timing of chemical treatment, control activity, etc. It is possible to improve. The compound of the present invention and the other active ingredient compounds of other agricultural chemicals may be prepared separately and mixed at the time of spraying, or both may be used together. The present invention includes such a composition for controlling mixed pests.

The mixing ratio (weight ratio) between the compound of the present invention and the active ingredient compound of other pesticides cannot be defined unconditionally due to differences in weather conditions, formulation form, application time, application location, pest type and occurrence, etc. 1: 300 to 300: 1, preferably 1: 100 to 100: 1. The appropriate amount to be applied is 0.1 to 50,000 g, preferably 1 to 30,000 g as the total amount of active ingredient compounds per hectare. The present invention also includes a method for controlling pests by a method for applying such a composition for controlling mixed pests.

Examples of active ingredient compounds (generic name; including some pending applications or test codes) of insecticides, acaricides, nematicides or soil pesticides in the above other pesticides include, for example, profenofos , Dichlorvos, fenamiphos, fenitrothion, EPN, diazinon, chlorpyrifos, chlorpyrifos-methyl, acephate, prothiofos, fothiaz , Cadusafos, disulfoton, isoxathion, isofenphos, ethion, etrimfos, quinalphos, dimethylvinphos, dimethoate, sulfophos ( sulprofos), thiometon, bamidthione (vamidot) hion), pyraclofos, pyridaphenthion, pirimiphos-methyl, propaphos, phosalone, formothion, malathion, tetrachlorvinphos, chlorfen Chlorfenvinphos, cyanophos, trichlorfon, methidathion, phenthoate, ESP, azinphos-methyl, fenthion, heptenophos, methoxychlor, Parathion, phosphocarb, demeton-S-methyl, monocrotophos, methamidophos, imicyafos, parathion-methyl, terbufos ( terbufos), phosphamidon (phos) organophosphate compounds such as phamidon, phosmet, phorate;
Carbaryl, propoxur, aldicarb, carbofuran, thiodicarb, methomyl, oxamyl, ethiofencarb, pirimicarb, fenobucarb, fenobucarb Carbamates such as carbosulfan, benfuracarb, bendiocarb, furathiocarb, isoprocarb, metolcarb, xylylcarb, XMC, fenothiocarb Compound;
Nereistoxin derivatives such as cartap, thiocyclam, bensultap, sodium thiosultap-sodium;
Organochlorine compounds such as dicohol, tetradifon, endosulfan, dienochlor, dieldrin;

Organometallic compounds such as fenbutatin oxide and cyhexatin;
Fenvalerate, permethrin, cypermethrin, deltamethrin, cyhalothrin, tefluthrin, etofenprox, flufenprox, cyfluthrin , Fenpropathrin, flucytrinate, fluvalinate, cycloprothrin, lambda-cyhalothrin, pyrethrins, esfenvalerate, tetramethrin (Tetramethrin), resmethrin, protrifenbute, bifenthrin, zeta-cypermethrin, acrinathrin, alpha-cypermet hrin), allethrin, gamma-cyhalothrin, theta-cypermethrin, tau-fluvalinate, tralomethrin, profluthrin, beta-si Pyrethroid compounds such as per-methrin (beta-cypermethrin), beta-cyfluthrin, mettofluthrin, phenothrin, flumethrin;
Diflubenzuron, chlorfluazuron, teflubenzuron, flufenoxuron, triflumuron, hexaflumuron, lufenuron, novaluron, novaluron, ), Bistrifluron, benzoylurea compounds such as fluazuron;
Juvenile hormone-like compounds such as metoprene, pyriproxyfen, phenoxycarb, diofenolan;
Pyrazole compounds such as fenpyroximate, fipronil, tebufenpyrad, etiprole, tolfenpyrad, acetoprole, pyrafluprole, pyriprole;
Neonicotioids such as imidacloprid, nitenpyram, acetamiprid, thiacloprid, thiamethoxam, clothianidin, dinotefuran, nithiazine;
Hydrazine compounds such as tebufenozide, methoxyfenozide, chromafenozide, halofenozide;

Pyridine compounds such as pyridalyl and flonicamid;
Cyclic ketoenol compounds such as spirodiclofen, spiromesifen, spirotetramat;
Strobilurin-based compounds such as fluacrypyrim;
Pyrimidinamine compounds such as flufenerim;
Dinitro compounds; organic sulfur compounds; urea compounds; triazine compounds; hydrazone compounds; and other compounds such as buprofezin, hexythiazox, amitraz, chlordimeform, silafluofen ), Triazamate, pymetrozine, pyrimidifen, chlorfenapyr, indoxacarb, acequinocyl, etoxazole, cyromazine, 1,3-dichloropropene (1,3-dichloropropene), diafenthiuron, benclothiaz, bifenazate, propargite, clofentezine, metaflumizone (me taflumizone), flubendiamide, cyflumetofen, chlorantraniliprole, cyantraniliprole, cyenopyrafen, cyenopyrafen, pyrifluquinazon, fenazapy, fenazapy , Amidoflumet, sulfluramid, hydramethylnon, metaldehyde, HGW 86, ryanodine, verbutin, cypropene, and the like; . Furthermore, Bacillus thuringiensis aizawai, Bacillus thuringiensis kurstaki, Bacillus thuringiensis israelensis, Bacillus thuringiensis japonensis, Bacillus thuringiensis tenebrionis or crystal protein toxins produced by Bacillus thuringiensis, entomopathogenic fungi, nematopathogenic fungi, etc. Microbial pesticides such as: avermectin, emamectin-benzoate, milbemectin, milbemycin, spinosad, ivermectin, lepimectin, DE-175, abamectin Antibiotics and semi-synthetic antibiotics such as abamectin, emamectin, spinetoram; natural products such as azadirachtin, rotenone; repellents such as deet; Etc. It is done.

In the above-mentioned other agricultural chemicals, as an active ingredient compound (generic name; including partial application, or Japan Plant Protection Association test code), for example, mepanipyrim, pyrimethanil, cyprodinil Anilinopyrimidine compounds such as (cyprodinil);
Such as 5-chloro-7- (4-methylpiperidin-1-yl) -6- (2,4,6-trifluorophenyl)-[1,2,4] triazolo [1,5-a] pyrimidine Triazolopyrimidine compounds;
Pyridinamine compounds such as fluazinam;
Triadimefon, bitertanol, triflumizole, etaconazole, propiconazole, penconazole, flusilazole, microbutanil, cyproconazole cyproconazole), tebuconazole, hexaconazole, furconazole-cis, prochloraz, metconazole, epoxiconazole, tetraconazole, o Oxpoconazole fumarate, sipconazole, prothioconazole, triadimenol, flutriafol, difenoconazole , Fluquinconazole, fenbuconazole, bromuconazole, diniconazole, tricyclazole, probenazole, cimeconazole, pefurazoate, ipconazole, ipconazole ), Azole compounds such as imibenconazole;

Quinoxaline compounds such as quinomethionate;
Dithiocarbamate compounds such as maneb, zineb, mancozeb, polycarbamate, metiram, propineb, thiram;
Organochlorine compounds such as fthalide, chlorothalonil, quintozene;
Imidazole compounds such as benomyl, thiophanate-methyl, carbendazim, thiabendazole, fuberiazole, cyazofamid;
Cyanoacetamide compounds such as cymoxanil;
Metalaxyl, metalaxyl-M, mefenoxam, oxadixyl, offurace, benalaxyl, benalaxyl-M, also known as kiralaxyl, chiax ), Fluralaxyl, cyprofuram, carboxyxin, oxycarboxin, thifluzamide, boscalid, isothianil, bixafen, thiadinyl, Anilide compounds such as sedaxane;

Sulfamide-type compounds such as dichlofluanid;
Copper-based compounds such as cupric hydroxide and oxine copper;
Isoxazole compounds such as hymexazol;
Fosetyl aluminum (fosetyl-Al), tolclofos-methyl, edifenphos, iprobenfos, S-benzyl O, O-diisopropyl phosphorothioate, O-ethyl S, S-diphenyl phosphorodithioate, aluminum Organophosphorus compounds such as ethyl hydrogen phosphonate;
Phthalimide compounds such as captan, captafol, folpet;
Dicarboximide compounds such as procymidone, iprodione, vinclozolin;

Benzanilide compounds such as flutolanil and mepronil;
Penthiopyrad, 3- (difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9RS) -1,2,3,4-tetrahydro-9-isopropyl-1,4-methanonaphthalen-5-yl ] Two syn isomers of pyrazole-4-carboxamide and 3- (difluoromethyl) -1-methyl-N-[(1RS, 4SR, 9SR) -1,2,3,4-tetrahydro-9-isopropyl-1 Amido compounds such as a mixture of two anti-isomers of (, 4-methanonaphthalen-5-yl] pyrazole-4-carboxamide (isopyrazam), silthiopham, fenoxanil;
Benzamide compounds such as fluopyram and zoxamid;
Piperazine compounds such as triforine;
Pyridine compounds such as pyrifenox;
Carbinol compounds such as fenarimol;
Piperidine-based compounds such as fenpropidine;
Morpholine compounds such as fenpropimorph and tridemorph;

Organotin compounds such as fentin hydroxide and fentin acetate;
Urea-based compounds such as pencycuron;
Synamic acid compounds such as dimethomorph, flumorph;
Phenyl carbamate compounds such as dietofencarb;
Cyanopyrrole compounds such as fludioxonil and fenpiclonil;
Azoxystrobin, kresoxim-methyl, metominofen, trifloxystrobin, picoxystrobin, oryzastrobin, dimoxystrobin Strobilurin-based compounds such as pyraclostrobin, fluoxastrobin;

Oxazolidinone compounds such as famoxadone;
Thiazole carboxamide compounds such as ethaboxam;
Valinamide compounds such as iprovalicarb, benchthiavalicarb-isopropyl;
Acylamino acid compounds such as methyl N- (isopropoxycarbonyl) -L-valyl- (3RS) -3- (4-chlorophenyl) -β-valaniphenate;
Imidazolinone compounds such as fenamidone;
Hydroxyanilide compounds such as fenhexamid;
Benzenesulfonamide compounds such as flusulfamide;
Oxime ether compounds such as cyflufenamid;
Anthraquinone compounds;
Crotonic acid compounds;
Antibiotics such as validamycin, kasugamycin, polyoxins;
Guanidine compounds such as iminoctadine and dodine;
Quinoline-based compounds such as 6-tertiarybutyl-8-fluoro-2,3-dimethylquinolin-4-yl acetate (tebufloquin);
Thiazolidines such as (Z) -2- (2-fluoro-5- (trifluoromethyl) phenylthio) -2- (3- (2-methoxyphenyl) thiazolidine-2-ylidene) acetonitrile (flutianil) Compound;

Other compounds include isoprothiolane, pyroquilon, diclomezine, quinoxyfen, propamocarb hydrochloride, chloropicrin, dazomet, and metam sodium salt. metam-sodium, nicobifen, metrafenone, UBF-307, diclocymet, proquinazid, amisulbrom, pyriofenone, pyribencarb, mandipropamide, mandipropamide (mandipropamide) (fluopicolide), carpropamid, meptyldinocap, ferimzone, spiroxamine, S-2188 (fenpyrazamine), S-2200, ZF-9646, BCF-051, BCM-061 , BCM-062;

Other agrochemicals that can be used in combination with or combined with the compounds of the present invention include, for example, active compound compounds of herbicides such as those described in The Pesticide Manual (15th edition), particularly those of soil treatment type. There is.

Examples of animal parasite control agents include ectoparasites that parasitize on the body surface of the host animal (back, armpit, lower abdomen, inner thigh, etc.) and the host animal body (stomach, intestinal tract, lung, heart, liver). , Vascular, subcutaneous, lymphoid tissue, etc.) are effective in controlling endoparasites, and in particular, are effective in controlling ectoparasites.

Examples of ectoparasites include animal parasitic mites and fleas. There are so many of these types that it is difficult to list them all.

The animal parasitic mites, for example Boophilus microplus (Boophilus microplus), Rhipicephalus sanguineus (Rhipicephalus sanguineus), Haemaphysalis longicornis (Haemaphysalis longicornis), Haemaphysalis flava (Haemaphysalis flava), Adenophora chima tick (Haemaphysalis campanulata), Isukachimadani (Haemaphysalis concinna), Yamatochimadani (Haemaphysalis japonica), H. kitaokai (Haemaphysalis kitaokai), Iyasuchimadani (Haemaphysalis ias), Ixodes ovatus (Ixodes ovatus), I. nipponensis (Ixodes nipponensis), Schulze ticks (Ixodes persulcatus), Takasago testudinarium (Amblyomma testudinarium), Ootogechimadani (Haemaphysalis megaspinosa ), tick such as Dermacentor reticulatus , Dermacentor taiwanesis ; duck ( Dermanyssus gallinae ); Shidani (Ornithonyssus sylviarum), Torisashidani, such as Southern tri sand mite (Ornithonyssus bursa); Nan iodine tsutsugamushi (Eutrombicula wichmanni), red mites (Leptotrombidium akamushi), L. pallidum (Leptotrombidium pallidum), Fuji chiggers (Leptotrombidium fuji), Tosa mites ( Leptotrombidium tosa), Europe Aki mites (Neotrombicula autumnalis), the United States chiggers (Eutrombicula alfreddugesi), chiggers, such as Miyagawa Tama chiggers (Helenicula miyagawai); Inutsumedani (Cheyletiella yasguri), rabbit Tsumedani (Cheyletiella parasitivorax), Nekotsumedani (Cheyletiella blakei) Tsumedani, such as; rabbits 9,000 mite (Psoroptes cuniculi), Ushishokuhidani (Chorioptes bovis), dog ear mites (Otodectes cynotis), mange mites (Sar coptes scabiei ), mite mites like Notoedres cati ; mite mites like Demodex canis , and the like. Among them, the animal parasite control agent containing the compound of the present invention is particularly effective for controlling ticks and the like.

Examples of animal parasitic fleas include ectoparasite worms belonging to the order Flea ( Siphonaptera ), and more specifically, fleas belonging to the family Flea family ( Pulicidae ), Nagano family ( Ceratephyllus ), and the like. Examples of fleas belonging to the family flea family include, for example, dog fleas ( Ctenocephalides canis ), cat fleas ( Ctenocephalides felis ), human fleas ( Purex irritans ), elephant fleas ( Echidnophaga gallinacea ), keops mouse fleas ( Xenopsylla cheopis ) Leptopsylla segnis ), European mouse minnow ( Nosopsyllus fasciatus ), and Yamamoto mouse ( Monopsyllus anisus ); Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling fleas belonging to the family Flea, particularly dog fleas and cat fleas.

Other ectoparasites include, for example, lice such as bovine lice, foal lice, sheep lice, bovine white lice, head lice; lice such as dog lice; blood-sucking dipterous pests such as bovine abs, quail sharks, . In addition, examples of endoparasites include nematodes such as lungworms, benthic worms, tuberous worms, gastric parasites, roundworms, and filamentous worms; Tapeworms such as real tapeworms, multi-headed tapeworms, single-banded tapeworms, multi-banded tapeworms; Japanese schistosomiasis, fluke such as liver cirrhosis; coccidium, malaria parasite, intestinal granulocyst, toxoplasma Protozoa such as Ptosporidium, and the like.

Examples of host animals include various pet animals, livestock, poultry, etc., and more specifically dogs, cats, mice, rats, hamsters, guinea pigs, squirrels, rabbits, ferrets, birds (eg, pigeons, parrots, (E.g., nine-bird, bird, parakeet, juvenile pine, canary, etc.), cattle, horses, pigs, sheep, ducks, chickens, etc. Among them, the animal parasite control agent containing the compound of the present invention is effective for controlling pests parasitic on pet animals or livestock, particularly ectoparasites. Among pet animals or domestic animals, it is particularly effective for dogs, cats, cows or horses.

When the compound of the present invention is used as an animal parasite control agent, it may be used as it is, and together with suitable adjuvants, powders, granules, tablets, powders, capsules, liquid agents, emulsions, aqueous suspensions, It can also be used in various forms such as an oily suspension. In addition to the above-mentioned preparation forms, any preparation forms used in the normal field can be used as long as the object of the present invention is met. Examples of the adjuvant used in the preparation include anionic surfactants and nonionic surfactants exemplified as the aforementioned preparation adjuvants for agricultural and horticultural pesticides; positive agents such as cetyltrimethylammonium bromide. Ionic surfactants: water, acetone, acetonitrile, N-methylacetamide, N, N-dimethylacetamide, N, N-dimethylformamide, 2-pyrrolidone, N-methyl-2-pyrrolidone, kerosene, triacetin, methanol, Ethanol, isopropanol, benzyl alcohol, ethylene glycol, propylene glycol, polyethylene glycol, liquid polyoxyethylene glycol, butyl diglycol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monoethyl Solvents such as ether, diethylene glycol normal butyl ether, dipropylene glycol monomethyl ether, dipropylene glycol normal butyl ether; oxidations such as butylhydroxyanisole, butylhydroxytoluene, ascorbic acid, sodium metabisulfite, propyl gallate, sodium thiosulfate Inhibitors; Film forming agents such as polyvinylpyrrolidone, polyvinyl alcohol, vinyl acetate and vinylpyrrolidone copolymers; vegetable oils and mineral oils exemplified as preparations for the aforementioned agricultural and horticultural pest control agents; lactose, sucrose, glucose , Starch, wheat flour, corn flour, soybean oil cake, defatted rice bran, calcium carbonate, and other carriers such as commercially available feed materials. Each component of these adjuvants can be used by appropriately selecting one or two or more types without departing from the object of the present invention. In addition to the above-mentioned adjuvants, it can be used by appropriately selecting from those known in the field, and further, selected from various adjuvants used in the above-mentioned agricultural and horticultural fields. You can also

The compounding ratio (weight ratio) of the compound of the present invention and various adjuvants is usually about 0.1: 99.9 to 90:10. In actual use of these preparations, use them as they are, or dilute them to a predetermined concentration with a diluent such as water, and add various spreading agents (surfactants, vegetable oils, mineral oils, etc.) as necessary. Can be used.

Administration of the compound of the present invention to the host animal is performed orally or parenterally. Examples of the oral administration method include a method of administering tablets, liquid agents, capsules, wafers, biscuits, minced meat, and other feeds containing the compound of the present invention. As a parenteral administration method, for example, the compound of the present invention is prepared into an appropriate preparation and then taken into the body by intravenous administration, intramuscular administration, intradermal administration, subcutaneous administration, etc .; spot-on A method of administering to the body surface by treatment, pour-on treatment, spray treatment, etc .; a method of embedding a resin piece containing the compound of the present invention under the skin of a host animal, and the like.

The dose of the compound of the present invention to the host animal varies depending on the administration method, administration purpose, disease symptoms, etc., but is usually in the range of 0.01 mg to 100 g, preferably 0.1 mg to 10 g, relative to 1 kg body weight of the host animal. Is suitable for administration.

The present invention includes a method for controlling pests according to the administration method or dosage as described above, particularly a method for controlling ectoparasites or endoparasites.

Further, in the present invention, there are cases where various diseases of host animals caused by them can be prevented or treated by controlling animal parasitic pests as described above. As described above, the present invention includes a prophylactic or therapeutic agent for parasitic animal diseases containing the compound of the present invention as an active ingredient, and a method for preventing or treating parasitic animal diseases.

When the compound of the present invention is used as an animal parasite control agent, various vitamins, minerals, amino acids, nutrients, enzyme preparations, antipyretics, sedatives, anti-inflammatory agents, bactericides, coloring agents, fragrances, It can be mixed with or used in combination with preservatives and the like. Also, if necessary, mix or use with other animal drugs and pesticides such as anthelmintics, anticoccidials, insecticides, acaricides, fleas, nematicides, fungicides, antibacterials, etc. In this case, a more excellent effect may be exhibited. The present invention includes a composition for controlling mixed pests in which various components as described above are mixed or used together, and a method for controlling pests using the composition, particularly a method for controlling ectoparasites or endoparasites. Is also included.

Next, although an example of the desirable aspect of the present invention is described, the present invention is not limited to these.
(1) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or alkyl substituted with A, unsubstituted or cyclosubstituted with Q Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , cyano, ^{^{^{nitro, NR 4 R 5, CONR 4}}} R 5, S (O) n R 3, it is oR ^2, COR ² or COOR ^2; A is a halogen ^{atom, oR 2, S (O)} n R 3, _{^{S (O) n R 3,}} NR 4 R 5, cyano, cycloalkyl, aryl, heterocyclic _{^{^{group, SCH 2 COOR 2, NHNR 4}}} R 5, COOR 2, a nitro or CH (CN) _2; Q is a halogen Atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl; R ⁴ is a hydrogen atom or alkyl; R ⁵ is a hydrogen atom, an alkyl, cycloalkyl, ^{^{haloalkyl, COR 2, COOR 2, S}} (O) n R 3, CH 2 CH 2 oR 2 or CH ₂ CN Ri; n is an integer of 0 to 2, imidazo pyrimidine derivative or pesticide containing a salt thereof as an active ingredient.

(2) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or alkyl substituted with A, unsubstituted or substituted with Q Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , cyano, ^{^{^{nitro, NR 4 R 5, CONR 4}}} R 5, S (O) n R 3, it is oR ^2, COR ² or COOR ^2; A is a halogen ^{atom, oR 2, S (O)} n R 3, _{^{S (O) n R 3,}} NR 4 R 5, cyano, cycloalkyl, aryl, heterocyclic _{^{^{group, SCH 2 COOR 2, NHNR 4}}} R 5, COOR 2, a nitro or CH (CN) _2; Q is a halogen Atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl; R ⁴ is a hydrogen atom or alkyl; R ⁵ is a hydrogen atom, an alkyl, cycloalkyl, ^{^{haloalkyl, COR 2, COOR 2, S}} (O) n R 3, CH 2 CH 2 oR 2 or CH ₂ CN Ri; n is an integer of 0-2, a method for controlling pests applying an effective amount of imidazo pyrimidine derivative or a salt thereof.

(3) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or substituted with alkyl substituted with A, unsubstituted or substituted with Q Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , Cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² , COOR ² , alkoxyvinyl, S (O) _m [N (CN)] R ³ or C (R ³ ) = NNG ¹ G ² ; A is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; Q is a halogen atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , Cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl , Cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl, unsubstituted or aryl or haloalkyl substituted with a halogen atom; R ⁴ is a hydrogen atom or alkyl R ⁵ is a hydrogen atom, alkyl, cycloalkyl, haloalkyl, COR ² , COOR ² , S (O) _n R ³ , CH ₂ CH ₂ OR ² or CH ₂ CN; G ¹ and G ² are each independently A hydrogen atom, alkyl or COOR ³ , G ¹ and G ² may be bonded to each other to form a ring with the adjacent nitrogen atom; n is an integer of 0 to 2; m is 0 or 1 An imidazopyrimidine derivative or a salt thereof, which is an integer of

(4) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or substituted with alkyl substituted with A, unsubstituted or substituted with Q substituted cyclo Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , cyano, ^{^{^{nitro, NR 4 R 5, CONR 4}}} R 5, S (O) n R 3, it is oR ^2, COR ² or COOR ^2; A is a halogen ^{atom, oR 2, S (O)} n R 3, _{^{S (O) n R 3,}} NR 4 R 5, cyano, cycloalkyl, aryl, heterocyclic _{^{^{group, SCH 2 COOR 2, NHNR 4}}} R 5, COOR 2, a nitro or CH (CN) _2; Q is a halogen Atom, OR ² , S (O) _n R ³ , OS (O) _n R ³ , NR ⁴ R ⁵ , cyano, alkyl, cycloalkyl, aryl, heterocyclic group, SCH ₂ COOR ² , NHNR ⁴ R ⁵ , COOR ² , nitro or CH (CN) ₂ ; R ² is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl, alkoxyalkyl, acetyl, benzyl or aryl; R ³ is alkyl; R ⁴ is a hydrogen atom or alkyl; R ⁵ is a hydrogen atom, an alkyl, cycloalkyl, ^{^{haloalkyl, COR 2, COOR 2, S}} (O) n R 3, CH 2 CH 2 oR 2 or CH ₂ CN Ri; n is an integer of 0 to 2, imidazo pyrimidine derivative or a salt thereof described in (1).

(5) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or substituted with alkyl substituted with A, unsubstituted or substituted with Q Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , Cyano, nitro, NR ⁴ R ⁵ , CONR ⁴ R ⁵ , S (O) _n R ³ , OR ² , COR ² , COOR ² , alkoxyvinyl, S (O) _m [N (CN)] R ³ or C (R ³ ) = NNG ¹ G ² ; provided that when Cy is aryl substituted with X, R ¹ is not unsubstituted alkyl, or the imidazopyrimidine derivative or a salt thereof according to (3) above.

(6) In formula (I), Cy is aryl substituted with X or heteroaryl substituted with X; R ¹ is unsubstituted or substituted with alkyl substituted with A, unsubstituted or substituted with Q substituted cyclo Alkyl, unsubstituted or substituted with alkenyl, unsubstituted or substituted with alkynyl, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR ² , CH = NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl , cyano, ^{^{^{nitro, NR 4 R 5, CONR 4}}} R 5, S (O) n R 3, be oR ^2, COR ² or COOR ^2; however when Cy is aryl substituted with X , R ¹ is not unsubstituted alkyl, imidazo pyrimidine derivative or a salt thereof described in (4).

(7) The imidazopyrimidine derivative or a salt thereof according to (5), wherein in formula (I), Cy is heteroaryl substituted with X.

(8) The imidazopyrimidine derivative or a salt thereof according to (6), wherein in formula (I), Cy is heteroaryl substituted with X.

(9) In formula (I), Cy is aryl substituted by X, R ¹ is alkyl substituted by A, unsubstituted or substituted by Q, cycloalkyl, unsubstituted or substituted by A , Unsubstituted or A-substituted alkynyl, halogen atom, cyano, aryl, unsubstituted or alkyl-substituted heterocyclic group, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ , the imidazopyrimidine derivative or a salt thereof according to (5) above.

(10) In formula (I), Cy is aryl substituted with X, and R ¹ is alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or alkenyl substituted with A , Unsubstituted or A-substituted alkynyl, halogen atom, cyano, aryl, unsubstituted or alkyl-substituted heterocyclic group, CH═NOR ² , CH═NNR ⁴ R ⁵ , COR ² , COOR ² , OR ² , S (O) _n R ³ , NR ⁴ R ⁵ or CONR ⁴ R ⁵ , the imidazopyrimidine derivative or a salt thereof according to (6) above.

(11) An agricultural and horticultural pest control agent comprising an imidazopyrimidine derivative represented by the formula (I) or a salt thereof as an active ingredient.
(12) An insecticide, acaricide, nematicide or soil-killing insecticide containing the imidazopyrimidine derivative represented by the formula (I) or a salt thereof as an active ingredient.
(13) An insecticide or acaricide containing the imidazopyrimidine derivative represented by the formula (I) or a salt thereof as an active ingredient.
(14) A method for controlling pests by applying an effective amount of an imidazopyrimidine derivative represented by the formula (I) or a salt thereof.

Next, examples of the present invention will be described, but the present invention is not limited thereto. First, the synthesis example of this invention compound is described.
The ratio (/) of the eluent used in silica gel column chromatography in the synthesis examples is a volume ratio.

Synthesis example 1
Synthesis of 5- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) -7-methylimidazo [1,2-a] pyrimidine (Compound No. 1) (1) 3-Chloro-2- A mixed solution of 4.0 g of ethoxycarbonyl-5- (trifluoromethyl) pyridine, 1.01 g of acetone and 20 mL of tetrahydrofuran was ice-cooled, and 1.29 g of sodium ethoxide was added little by little. The reaction mixture was then warmed to room temperature and stirred for 7 hours. After completion of the reaction, the reaction mixture was acidified with 1 mol / L hydrochloric acid and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, concentrated under reduced pressure, and crude 1- [3-chloro-5- (trifluoromethyl) pyridin-2-yl] butane-1 , 3-dione was obtained.
(2) To the mixed solution of crude 1- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) butane-1,3-dione obtained in (1) and 30 mL of acetic acid, add 2 -Aminoimidazole sulfate 2.29 g and sodium acetate 1.56 g were added and heated at 80 ° C. for 2 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, added with 50 mL of water, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / hexane = 7/3) to obtain 2.51 g of the desired product.

Synthesis example 2
Synthesis of 5- (5-bromo-2-chlorophenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 96) (1) Methyl 5-bromo-2-chlorobenzoate 14.4 g, cyclo A mixed solution of 5.9 g of propyl methyl ketone and 120 mL of tetrahydrofuran was ice-cooled, and 4.8 g of sodium methoxide was added little by little. The reaction mixture was then warmed to room temperature and stirred for 5 hours. After completion of the reaction, the reaction mixture was acidified with 1 mol / L hydrochloric acid and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude 1- (5-bromo-2-chlorophenyl) -3-cyclopropylpropane-1,3-dione. 15.7 g was obtained.
(2) To a mixed solution of the crude 1- (5-bromo-2-chlorophenyl) -3-cyclopropylpropane-1,3-dione obtained in (1) and 100 mL of acetic acid, add 2-aminoimidazole. Sulfate 4.9 g and sodium acetate 3.1 g were added and heated at 100 ° C. for 4 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, neutralized with a saturated aqueous sodium bicarbonate solution, and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/1) to obtain 0.8 g of the desired product.

Synthesis example 3
5- (2-Chloro-5- (1-ethoxyvinyl) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 170) and 1- (4-Chloro-3- (7- Synthesis of cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) ethanone (Compound No. 97) (1) 5- (5-Bromo-2-chlorophenyl) -7-cyclopropylimidazo [1, To a mixed solution of 2-a] pyrimidine (Compound No. 96) 720 mg and toluene 40 mL, tetrakis (triphenylphosphine) palladium 230 mg and tributyl (1-ethoxyvinyl) tin 845 mg were added. Heated to reflux for hours. After completion of the reaction, the reaction mixture was filtered under reduced pressure, and the filtrate was concentrated under reduced pressure to give crude 5- (2-chloro-5- (1-ethoxyvinyl) phenyl) -7-cyclopropylimidazo [1,2-a Pyrimidine (Compound No. 170) was obtained.
(2) Total amount of crude 5- (2-chloro-5- (1-ethoxyvinyl) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 170) obtained in (1) To a mixed solution of 50 mL of tetrahydrofuran and 1 mL of 12 mol / L hydrochloric acid and 5 mL of water were added and heated at 40 ° C. for 14 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was washed 3 times with ethyl acetate. The aqueous layer was concentrated under reduced pressure, and the precipitated crystals were filtered under reduced pressure and washed with heptane to obtain 279 mg of the desired product.

Synthesis example 4
Synthesis of N- (1- (4-chloro-3- (7-cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) ethylidene) pyrrolidin-1-amine (Compound No. 101) 1- To a mixed solution of (4-chloro-3- (7-cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) ethanone (Compound No. 97) and 30 mL of methanol, add N-aminopyrrolidine. Hydrochloride 48 mg and pyridine 38 mg were added, and the mixture was heated to reflux for 6 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate / heptane = 1/2) to obtain 24 mg of the desired product.

Synthesis example 5
Synthesis of 5- (2-chloro-5- (methylthio) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 127) (1) 2-Chloro-5- (methylthio) benzoic acid A mixed solution of 10.0 g, 18 mol / L sulfuric acid 3.0 mL and methanol 100 mL was heated to reflux for 6 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 10.3 g of crude methyl 2-chloro-5- (methylthio) benzoate. It was measured by The ¹ H-NMR data ^[1 H- nuclear magnetic resonance spectroscopy of this compound (Nuclear Magnetic Resonance Spectroscopy). δ is a chemical shift value. ] Is as follows.
¹ H-NMR _{(solvent: CDCl 3 / 500MHz) δ (} ppm): 2.49 (3H, s), 3.95 (3H, s), 7.27 (1H, d), 7.35 (1H, d), 7.65 (1H, s ).
(2) A mixed solution of 5.0 g of crude methyl 2-chloro-5- (methylthio) benzoate obtained in (1), 2.2 g of cyclopropyl methyl ketone and 80 mL of tetrahydrofuran was ice-cooled, and 1.5 g of sodium methoxide was added. Was added little by little. The reaction mixture was then warmed to room temperature and stirred for 3 days. After completion of the reaction, the reaction mixture was acidified with 1 mol / L hydrochloric acid and extracted twice with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give crude 1- (2-chloro-5- (methylthio) phenyl) -3-cyclpropylpropane-1, 3.8 g of 3-dione was obtained.
(3) To a mixed solution of crude 1- (2-chloro-5- (methylthio) phenyl) -3-cyclpropylpropane-1,3-dione obtained in (2) and 50 mL of acetic acid, 2 -3.8 g of aminoimidazole sulfate and 2.3 g of sodium acetate were added and heated at 100 ° C for 3 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, water was added, and the mixture was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain 0.5 g of the desired product.

Synthesis Example 6
Synthesis of 5- (2-chloro-5- (methylsulfinyl) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 139) (1) 1- (2-Chloro-5- ( A mixed solution of 1.9 g of methylthio) phenyl) -3-cyclpropylpropane-1,3-dione and 50 mL of chloroform was ice-cooled, and 1.5 g of 3-chloroperbenzoic acid was added little by little. The reaction mixture was then warmed to room temperature and stirred for 20 hours. After completion of the reaction, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted once with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 1- (2-chloro-5- (methylsulfinyl) phenyl) -3-cyclpropylpropane-1,3-dione (1.7 g). Got.
(2) To a mixed solution of 1- (2-chloro-5- (methylsulfinyl) phenyl) -3-cyclpropylpropane-1,3-dione obtained in (1) and 50 mL of acetic acid, 3.2 g of aminoimidazole sulfate and 2.0 g of sodium acetate were added and heated at 100 ° C. for 3 days. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, neutralized with a saturated aqueous sodium bicarbonate solution, and extracted four times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: methanol / ethyl acetate = 1/10) to obtain 0.3 g of the desired product.

Synthesis example 7
Synthesis of 5- (2-chloro-5- (methylsulfonyl) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 147) 5- (2-chloro-5- (methylthio) phenyl ) A mixed solution of 150 mg of 7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 127) and 25 mL of chloroform was ice-cooled, and 171 mg of 3-chloroperbenzoic acid was added little by little. The reaction mixture was then warmed to room temperature and stirred for 19 hours. After completion of the reaction, saturated aqueous sodium bicarbonate solution was added to the reaction mixture. After separation, the organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: ethyl acetate) to obtain 40 mg of the desired product.

Synthesis example 8
Synthesis of 1- (4-chloro-3- (7-cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) (methyl) -λ ⁴ -sulfanilidenecyanamide (Compound No. 155) 5 -(2-Chloro-5- (methylthio) phenyl) -7-cyclopropylimidazo [1,2-a] pyrimidine (Compound No. 127) 61 mg, cyanamide 18 mg and acetonitrile 20 ml were mixed with ice. Then, 135 mg of iodobenzene diacetate was added little by little. The reaction mixture was then warmed to room temperature and stirred for 24 hours. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (eluent: methanol / ethyl acetate = 1/10) to obtain 35 mg of the desired product.

Synthesis Example 9
1- (4-Chloro-3- (7-cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) (methyl) -oxide-λ ⁴ -sulfanilidenecyanamide (Compound No. 163) Synthesis 1- (4-Chloro-3- (7-cyclopropylimidazo [1,2-a] pyrimidin-5-yl) phenyl) (methyl) -λ ⁴ -sulfanilidenecyanamide (Compound No. 155) 255 mg A mixed solution of 148 mg of 3-chloroperbenzoic acid and 50 mL of ethanol was ice-cooled, and 299 mg of potassium carbonate was dissolved in 10 ml of water and added little by little. The reaction mixture was then warmed to room temperature and stirred for 40 minutes. After completion of the reaction, a saturated aqueous sodium bicarbonate solution was added to the reaction mixture, and the mixture was extracted once with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent: methanol / ethyl acetate = 1/10) to obtain 141 mg of the desired product.

Representative examples of the compounds of formula (I) are listed in Table 1 (Tables 1 to 6). These compounds can be produced based on Synthesis Example 1 or the various production methods described above. In Tables 1 to 5, No. represents compound No., Me represents methyl, c-Pr represents cyclopropyl, i-Pr represents isopropyl, Ac represents acetyl, Ph represents phenyl, and physical properties The temperature shown as is the melting point. Further, ¹ H-NMR data [ ¹ H-nuclear magnetic resonance spectroscopy was used to measure the compounds whose properties in Table 1 are oily or amorphous. δ is a chemical shift value] is shown in Tables 2-5.

Next, test examples are described.
Test Example 1 Effect test on peach aphid Japanese radish leaves were inserted into a test tube containing water, and about 20 first-instar larvae were released on the leaves. The next day, after counting the number of larvae parasitic on the radish leaves, the parasitic radish leaves were immersed for about 10 seconds in a chemical solution adjusted so that the concentration of the compound of the present invention was 200 ppm. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Five days after the treatment, the viability of the peach aphid was determined, and the mortality rate was determined by the following formula. The detached insects and abnormal insects were regarded as dead insects. When the compounds No. 1, 11 and 139 were tested, all the compounds showed a death rate of 80% or more.
Death rate (%) = (1− (number of surviving insects / number of treated insects)) × 100

Test Example 2 Effect test on green planthopper Rice seedlings were immersed in a chemical solution adjusted to have a concentration of the present compound of 200 ppm for about 10 seconds. After the chemical solution was air-dried, the root was wrapped with wet absorbent cotton and placed in a test tube. Ten 10-year-old larvae of the green planthopper were released into this, and the tube opening was covered with gauze and left in a temperature-controlled room at 25 ° C. Five days after the insect release, the dead planthopper was judged to be alive or dead, and the mortality rate was determined by the following formula. When the compound No. 1, 3, 11, 12, 15, 46, 51, 95, 110, 113, 122, 127, 138, 139, 146, 147, 155 and 163 were tested, all the compounds were 80. % Mortality was more than 50%.
Death rate (%) = (Number of dead insects / Number of dead insects) × 100

Test Example 3 Effect test on silver leaf whitefly A potted cucumber seedling infested with silver leaf whitefly 1-2 instar larvae was sprayed with a chemical solution adjusted to a concentration of 200 ppm of the compound of the present invention using a hand spray. After the chemical solution was air-dried, it was left in a constant temperature room at 25 ° C. with illumination. Seven days after the treatment, the number of old larvae was examined, and the control value (%) was determined by the following formula. When said compound No.3, 12 and 46 were tested, all the compounds showed the control value of 80% or more.

Control value (%) = (1− (Ta × Cb) / (Tb × Ca)) × 100
Ta: old larvae after treatment in treated cucumber seedlings
Tb: Number of 1-2 instar larvae before treatment in treated cucumber seedlings
Ca: number of old larvae after treatment in untreated cucumber seedlings
Cb: Number of 1-2 instar larvae before treatment in untreated cucumber seedlings

Test Example 4 Medicinal Efficacy Test Using Dogs Against Phytophyllum Tick A dog (beagle, 8 months old) was administered a gelatin capsule containing 10 mg / kg body weight of the compound of the present invention. Immediately thereafter, about 50 young mites were collected from the ear of the dog. Let go through and artificially infest. After the treatment, observe the number of infestations, the number of drops, and the life and death of the fallen spider mites. As a result, the compound of the present invention drops or kills the parasitic spider mite.

Test Example 5 Medicinal Efficacy Test Using a Dog against a Cat Flea A gelatin capsule containing 10 mg / kg body weight of the compound of the present invention was administered to a dog (beagle, 8 months old), and immediately after that about 100 cat flea non-blood-sucking adults were covered in the back Let go on and let it infest. After the treatment, collect the cat fleas using a flea removal comb and count the number of fixings. As a result, the compound of the present invention suppresses cat flea infestation.

Next, formulation examples are described.
Formulation Example 1
(1) Compound of the present invention 20 parts by weight (2) Clay 70 parts by weight (3) White carbon 5 parts by weight (4) Sodium polycarboxylate 3 parts by weight (5) Sodium alkylnaphthalenesulfonate 2 parts by weight or more To make a wettable powder.

Formulation Example 2
(1) Compound of the present invention 5 parts by weight (2) 60 parts by weight of talc (3) 34.5 parts by weight of calcium carbonate (4) Liquid paraffin 0.5 parts by weight or more are uniformly mixed to obtain a powder.

Formulation Example 3
(1) Compound of the present invention 20 parts by weight (2) N, N-dimethylacetamide 20 parts by weight (3) Polyoxyethylene tristyryl phenyl ether 10 parts by weight (4) Calcium dodecylbenzenesulfonate 2 parts by weight (5) Xylene 48 A mixture of more than parts by weight is uniformly mixed and dissolved to obtain an emulsion.

Formulation Example 4
(1) Clay 68 parts by weight (2) Sodium lignin sulfonate 2 parts by weight (3) Polyoxyethylene alkylaryl sulfate 5 parts by weight (4) White carbon 25 parts by weight A mixture of each component and the compound of the present invention Mix at a weight ratio of 4: 1 to make a wettable powder.

Formulation Example 5
(1) Compound of the present invention 50 parts by weight (2) Sodium alkylnaphthalene sulfonate formaldehyde condensate 2 parts by weight (3) Silicone oil 0.2 parts by weight (4) Water 47.8 parts by weight or more uniformly mixed (5) 5 parts by weight of sodium polycarboxylate (6) 42.8 parts by weight of anhydrous sodium sulfate are further added to the crushed stock solution, and the mixture is uniformly mixed, granulated and dried to obtain a granulated wettable powder.

Formulation Example 6
(1) Compound of the present invention 5 parts by weight (2) Polyoxyethylene octylphenyl ether 1 part by weight (3) Polyoxyethylene alkyl ether phosphate 0.1 part by weight (4) Granular calcium carbonate 93.9 parts by weight (1 ) To (3) are mixed uniformly in advance and diluted with an appropriate amount of acetone, and then sprayed onto (4) to remove acetone and form granules.

Formulation Example 7
(1) Compound of the present invention 2.5 parts by weight (2) N, N-dimethylacetamide 2.5 parts by weight (3) Soybean oil 95.0 parts by weight or more are uniformly mixed and dissolved to give a trace amount of spray ( ultra low volume formulation).

Formulation Example 8
(1) Compound of the present invention 40 parts by weight (2) Polyoxyethylene tristyryl phenyl ether potassium phosphate 4 parts by weight (3) Silicone oil 0.2 parts by weight (4) Xanthan gum 0.1 parts by weight (5) Ethylene glycol 5 Part by weight (6) Water 50.7 parts by weight or more are uniformly mixed and pulverized to obtain an aqueous suspension.

Formulation Example 9
(1) Compound of the present invention 10 parts by weight (2) Diethylene glycol monoethyl ether 80 parts by weight (3) Polyoxyethylene alkyl ether 10 parts by weight or more of ingredients are mixed uniformly to obtain a liquid agent.

The pest control agent comprising the imidazopyrimidine derivative of the present invention or a salt thereof as an active ingredient has a low dose and a very high control effect on pests, and various pests and animals that are problematic in the field of agriculture and horticulture It is extremely useful because it can control pests parasitizing the plant, and has safety against crops, pest natural enemies or mammals.
The entire contents of the specification, claims, and abstract of Japanese Patent Application No. 2009-288224 filed on Dec. 18, 2009 are incorporated herein as the disclosure of the specification of the present invention. Is.

Claims

Formula (I):

Wherein Cy is aryl substituted with X or heteroaryl substituted with X; R 1 is unsubstituted or alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or Alkenyl substituted with A, unsubstituted or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR 2 , CH = NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , CONR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 , COOR 2 , alkoxyvinyl, S (O) m [N (CN)] R 3 or C (R 3 ) = NNG 1 G 2 ; A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; Q is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, Alkyl, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; R 2 is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl , alkoxyalkyl, acetyl, benzyl, or aryl; R 3 is alkyl, unsubstituted or aryl or haloalkyl substituted with a halogen atom; R 4 is a hydrogen atom or alkyl; R 5 is water Atom, alkyl, cycloalkyl, haloalkyl, COR 2, COOR 2, S (O) n R 3, CH 2 CH 2 be OR 2 or CH 2 CN; G 1 and G 2 each independently represent a hydrogen atom, an alkyl or COOR 3 , G 1 and G 2 may be bonded to each other to form a ring with the adjacent nitrogen atom; n is an integer of 0 to 2; m is an integer of 0 or 1. ] The pest control agent which contains the imidazopyrimidine derivative represented by these, or its salt as an active ingredient.
An agricultural and horticultural pest control agent comprising the imidazopyrimidine derivative or a salt thereof according to claim 1 as an active ingredient.
Formula (I):

Wherein Cy is aryl substituted with X or heteroaryl substituted with X; R 1 is unsubstituted or alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or Alkenyl substituted with A, unsubstituted or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR 2 , CH = NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , CONR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 , COOR 2 , alkoxyvinyl, S (O) m [N (CN)] R 3 or C (R 3 ) = NNG 1 G 2 ; A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; Q is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, Alkyl, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; R 2 is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl , alkoxyalkyl, acetyl, benzyl, or aryl; R 3 is alkyl, unsubstituted or aryl or haloalkyl substituted with a halogen atom; R 4 is a hydrogen atom or alkyl; R 5 is water Atom, alkyl, cycloalkyl, haloalkyl, COR 2, COOR 2, S (O) n R 3, CH 2 CH 2 be OR 2 or CH 2 CN; G 1 and G 2 each independently represent a hydrogen atom, an alkyl or COOR 3 , G 1 and G 2 may be bonded to each other to form a ring with the adjacent nitrogen atom; n is an integer of 0 to 2; m is an integer of 0 or 1. A method for controlling pests by applying an effective amount of an imidazopyrimidine derivative represented by the formula:
Formula (I):

Wherein Cy is aryl substituted with X or heteroaryl substituted with X; R 1 is unsubstituted or alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or Alkenyl substituted with A, unsubstituted or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR 2 , CH = NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , CONR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 , COOR 2 , alkoxyvinyl, S (O) m [N (CN)] R 3 or C (R 3 ) = NNG 1 G 2 ; A is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; Q is a halogen atom, OR 2 , S (O) n R 3 , OS (O) n R 3 , NR 4 R 5 , cyano, Alkyl, cycloalkyl, aryl, heterocyclic group, SCH 2 COOR 2 , NHNR 4 R 5 , COOR 2 , nitro or CH (CN) 2 ; R 2 is a hydrogen atom, alkyl, alkenyl, alkynyl, haloalkyl, cyanoalkyl , alkoxyalkyl, acetyl, benzyl, or aryl; R 3 is alkyl, unsubstituted or aryl or haloalkyl substituted with a halogen atom; R 4 is a hydrogen atom or alkyl; R 5 is water Atom, alkyl, cycloalkyl, haloalkyl, COR 2, COOR 2, S (O) n R 3, CH 2 CH 2 be OR 2 or CH 2 CN; G 1 and G 2 each independently represent a hydrogen atom, an alkyl or COOR 3 , G 1 and G 2 may be bonded to each other to form a ring with the adjacent nitrogen atom; n is an integer of 0 to 2; m is an integer of 0 or 1. ] The imidazopyrimidine derivative represented by these, or its salt.
Formula (I):

Wherein Cy is aryl substituted with X or heteroaryl substituted with X; R 1 is unsubstituted or alkyl substituted with A, unsubstituted or cycloalkyl substituted with Q, unsubstituted or Alkenyl substituted with A, unsubstituted or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or substituted with alkyl, CH = NOR 2 , CH = NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S (O) n R 3 , NR 4 R 5 or CONR 4 R 5 ; X is alkyl, alkenyl, alkynyl, aryl, heterocyclic group, halogen atom, haloalkyl, cyano, nitro, NR 4 R 5 , CONR 4 R 5 , S (O) n R 3 , OR 2 , COR 2 , COOR 2 , alkoxyvinyl, S (O) m [N (CN)] R 3 or C (R 3 ) = NNG 1 G 2 ; provided that when Cy is aryl substituted with X, R 1 is not unsubstituted alkyl. The imidazopyrimidine derivative or its salt represented by Claim 4 represented by these.
The imidazopyrimidine derivative or a salt thereof according to claim 5, wherein in formula (I), Cy is heteroaryl substituted with X.
In formula (I), Cy is aryl substituted with X, R 1 is alkyl substituted with A, unsubstituted or Q-substituted cycloalkyl, unsubstituted or A-substituted alkenyl, unsubstituted Or alkynyl substituted with A, halogen atom, cyano, aryl, unsubstituted or alkyl-substituted heterocyclic group, CH═NOR 2 , CH═NNR 4 R 5 , COR 2 , COOR 2 , OR 2 , S ( O) n R 3, NR 4 R 5 or CONR a 4 R 5, imidazo pyrimidine derivative or a salt thereof according to claim 5.