WO2012096137A1 - Quinazoline-derived pest-control agent for use in agriculture and horticulture - Google Patents

Abstract

The following novel quinazoline derivative is useful as a pest-control agent. Formula (I) (In the formula, n represents an integer from 0 to 4; R¹ represents phenyl or the like; R² represents a hydrogen atom or the like; R³ represents methyl, benzyl, or the like; and R⁴ represents a hydrogen atom, a fluorine atom, or the like.)

Description

Quinazoline derivatives as pest control agents for agriculture and horticulture

The present invention relates to a novel quinazoline derivative that is useful as a pest control agent, particularly a pest control agent for agriculture and horticulture.

So far, various aminopyrimidine derivatives having pesticidal activity have been known. For example, see the following prior art documents.

However, in recent years, due to the development of drug resistance against pest control agents, a decrease in drug efficacy has become a serious problem. For this reason, there is still a need for the development of new compounds that replace the aminopyrimidine compounds having conventional pest control activity. The quinazoline derivative of the present invention is a novel compound and is not known to have agricultural and horticultural pest control activities.

JP-A-5-230036 JP-A-6-25187 JP-A-8-113564 JP-A-11-302261 JP-A-11-158161 JP 2006-8542 A WO2007 / 135029 WO2007 / 46809 WO2006 / 47397

An object of the present invention is to provide a novel quinazoline derivative, a production method thereof, and an agricultural and horticultural pest control agent comprising the same as an active ingredient.

As a result of intensive studies to solve the above problems, the present inventors have found that a novel quinazoline derivative, which is a novel compound, has remarkable agricultural and horticultural insecticidal, acaricidal, nematicidal and bactericidal activities, Based on this finding, the present invention has been completed.

That is, the present invention is as follows.

The first invention relates to a quinazoline derivative represented by the following formula [I].

[Wherein n represents an integer of 0 to 4, R ¹ is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, Group consisting of quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl A monocyclic or bicyclic ring optionally containing 0 to 3 heteroatoms, selected from
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, and 1 to 3 carbon atoms substituted by one halogen atom) Linear or branched haloalkyl, linear or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl substituted by one cyano group, and all of which two or all are the same substituents May be different substituents),
d) selected from hydrogen atoms and in the case of a) b) R ¹ is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O ) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, — NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or carbon cycloalkyl of atoms ^{3 ~ 8), - SiR 5} R 6 R 7, -OSiR 5 R 6 R 7 (R 5, R 6, R It is substituted linear or branched alkyl of 1 to 6 carbon atoms, straight-chain or branched haloalkyl having 1 to 3 carbon atoms which is substituted by one halogen atom, by one cyano radical Straight or branched cyanoalkyl and phenyl having 1 to 3 carbon atoms, two or all of which may be the same or all different substituents, and haloalkyl (identical or different, the number of halogen atoms A linear or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9), haloalkenyl (identical or different, and having 2 to 4 carbon atoms substituted with 1 to 4 halogen atoms) 6 linear or branched alkenyl groups), haloalkoxy (same or different, linear or branched alkoxy groups having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), Reed Direct alkoxy having 1 to 3 carbon atoms substituted by 1 or 2 acyl groups represented by rualkoxy (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO— 1 or 2 acyloxy groups represented by a chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O—) Substituted by a linear or branched alkyl group having 1 to 3 carbon atoms and alkylsulfonylalkyl substituted by 1 or 2 alkylsulfonyl groups having 1 to 8 carbon atoms Straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (—OSiR ⁵ R ⁶ R ^{7, where} R ⁵ , R ⁶ , and R ⁷ are linear chains having 1 to 6 carbon atoms) Or branched alkyl, one halogen atom Straight-chain or branched haloalkyl having 1 to 3 carbon atoms substituted, straight-chain or branched cyanoalkyl having 1 to 3 carbon atoms substituted by one cyano group, and phenyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted by two or all of which may be the same substituent or all different substituents), hydroxyalkyl (one or two hydroxyl groups) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), alkoxyalkyl (substituted by 1 or 2 linear or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, linear or branched having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Straight chain or branched alkyl group having 1 to 3 carbon atoms substituted by a branched 1 or 2 haloalkoxy group), alkylthioalkyl (straight chain or branched chain having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkylthio groups), a dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms). A dialkoxymethyl group substituted with two methyl groups), an alkoxyalkoxy (a straight chain having 1 to 3 carbon atoms substituted with 1 or 2 straight or branched alkoxy groups having 1 to 8 carbon atoms) Or a branched alkoxy group), cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 cyano groups), halogen, cyano, nitro, amino, Roxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (-CHO), carboxyl Optionally substituted with (—COOH), formamide (—NHCHO), cyclic ether, and cyclic amine,
R ² is a hydrogen atom, —R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a linear or branched group having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms), hydroxyalkyl ( A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), an alkoxyalkyl (a linear or branched 1 or 2 carbon atom having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an alkoxy group of the above, and a haloalkoxyalkyl (identical or different, and having 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms) 4 linear or branched 1 or A linear or branched alkyl group having 1 to 3 carbon atoms substituted by one haloalkoxy group), phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, and having 1 to 9 halogen atoms) Substituted or straight chain or branched alkyl group having 1 to 4 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Represents a branched or branched alkoxy group),
R ³ is —R, —C (O) R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or a branched alkyl, a linear or branched alkenyl having 2 to 8 carbon atoms, a linear or branched alkynyl having 2 to 8 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms) Hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl (a linear or branched group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkoxy groups), a haloalkoxyalkyl (identical or different, carbons substituted with 1 to 9 halogen atoms) 1 to 4 straight or branched 1 atom Is a linear or branched alkyl group having 1 to 3 carbon atoms substituted by two haloalkoxy groups), benzyl, phenethyl, phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms or haloalkoxy (same or different, substituted with 1 to 9 halogen atoms) A linear or branched 1 or 2 alkoxy group having 1 to 4 carbon atoms),
(R ⁴⁾ R ⁴ in the _n represents a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, a propargyloxy group , A benzyl group, a benzyloxy group, a heteroaryl group or a phenyl group, and when n is 2 to 4, each R ⁴ may be the same or different. n is as defined above. ]
The second invention is a method for producing a quinazoline derivative represented by the formula [I].

Furthermore, the third invention is a pest control agent comprising one or more quinazoline derivatives represented by the formula [I] as active ingredients.

The novel quinazoline derivative of the present invention represented by the formula [I] has an excellent control effect against pests, particularly agricultural and horticultural pests.

Hereinafter, the present invention will be described in detail.

In the quinazoline derivative in the present invention, in addition to the quinazoline derivative represented by the formula [I], a salt (sodium salt, potassium salt, magnesium salt, calcium salt, aluminum salt, etc.), hydrate, solvate of the derivative. And polymorphic substances are also included. Furthermore, all possible stereoisomers or optical isomers present in the compound of the present invention, and a mixture containing two or more kinds of the isomers in any ratio are also represented by the compound of the present invention (quinazoline derivative represented by the formula [I]). Included in the range.

The various substituents represented by the above compound [I] are as follows.

R ¹ is a substituent selected from any of the following a) to d).
a) Phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl Optionally containing 0 to 3 heteroatoms selected from the group consisting of, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl A group having an arbitrary ring atom (carbon atom or heteroatom) constituting a monocyclic or bicyclic ring as a bond.
b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, A cycloalkyl having 3 to 8 carbon atoms or a cycloalkenyl having 3 to 8 carbon atoms.
c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, and 1 to 3 carbon atoms substituted by one halogen atom) Linear or branched haloalkyl, linear or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl substituted by one cyano group, and all of which two or all are the same substituents May be different substituents).
d) A hydrogen atom.

In the case of a) or b), R ¹ is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O ) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, — NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a carbon atom number of 1 to 8) Linear or branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cyclocarbon having 3 to 8 carbon atoms. ^{alkyl), - SiR 5 R 6 R} 7, -OSiR 5 R 6 R 7 (R 5, R 6, R 7 is C 1 -C ~ A linear or branched alkyl, a linear or branched haloalkyl having 1 to 3 carbon atoms substituted by one halogen atom, or a carbon atom having 1 to 3 carbon atoms substituted by one cyano group Linear or branched cyanoalkyl and phenyl, two or all of which may be the same or all different substituents, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) Linear or branched alkyl group having 1 to 4 carbon atoms), haloalkenyl (same or different, linear or branched having 2 to 6 carbon atoms substituted with 1 to 4 halogen atoms) Alkenyl group), haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((carbon Linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) linear or branched having 1 to 3 carbon atoms substituted by 1 or 2 acyl groups represented by —CO— Substituted with one or two acyloxy groups represented by -CO-O- (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms). Straight chain or branched alkyl group having 1 to 3 carbon atoms), alkylsulfonylalkyl (carbon atom substituted by 1 or 2 straight chain or branched alkylsulfonyl group having 1 to 8 carbon atoms) A linear or branched alkyl group of 1 to 3), siloxyalkyl (—OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched having 1 to 6 carbon atoms) Alkyl, substituted by one halogen atom Straight-chain or branched haloalkyl having 1 to 3 atoms, straight-chain or branched cyanoalkyl having 1 to 3 carbon atoms substituted by one cyano group, and phenyl, two or all A linear or branched alkyl group having 1 to 3 carbon atoms substituted by the same substituent or all different substituents), hydroxyalkyl (carbon substituted by 1 or 2 hydroxyl groups) Straight chain or branched alkyl group having 1 to 3 atoms), alkoxyalkyl (1 to 2 carbon atoms substituted by 1 or 2 straight chain or branched alkoxy groups having 1 to 8 carbon atoms) 3 linear or branched alkyl groups), haloalkoxyalkyl (same or different, linear or branched 1 or 2 of 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Pieces A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a haloalkoxy group of the above, alkylthioalkyl (a linear or branched alkyl group having 1 to 8 carbon atoms or 1 or 2 alkylthio groups) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1) or dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms substituted with two methyl groups) Dialkoxymethyl group), alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by a linear or branched alkoxy group having 1 to 8 carbon atoms) ), Cyanoalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentaha Sulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (—CHO), carboxyl (—COOH) , Formamide (—NHCHO), cyclic ethers, and cyclic amines.

R ² is a hydrogen atom, —R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a linear or branched group having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms), hydroxyalkyl ( A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), an alkoxyalkyl (a linear or branched 1 or 2 carbon atom having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an alkoxy group of the above, and a haloalkoxyalkyl (identical or different, and having 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms) 4 linear or branched 1 or A linear or branched alkyl group having 1 to 3 carbon atoms substituted by one haloalkoxy group), phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, and having 1 to 9 halogen atoms) Substituted or straight chain or branched alkyl group having 1 to 4 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Or a branched alkoxy group).
R ³ is —R, —C (O) R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or a branched alkyl, a linear or branched alkenyl having 2 to 8 carbon atoms, a linear or branched alkynyl having 2 to 8 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms) Hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl (a linear or branched group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkoxy groups), a haloalkoxyalkyl (identical or different, carbons substituted with 1 to 9 halogen atoms) 1 to 4 straight or branched 1 atom Is a linear or branched alkyl group having 1 to 3 carbon atoms substituted by two haloalkoxy groups), benzyl, phenethyl, phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms), haloalkoxy (identical or different, carbon atoms substituted with 1 to 9 halogen atoms) 1 to 4 linear or branched alkoxy groups).
(R ⁴⁾ R ⁴ in the _n represents a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, a propargyloxy group , A benzyl group, a benzyloxy group, a heteroaryl group or a phenyl group, and when n is 2 to 4, each R ⁴ may be the same or different.
Monocyclic or bicyclic rings optionally containing 0 to 3 heteroatoms in R ¹ include phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl , Isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazolyl, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzoisoxazolyl, thienyl, benzothienyl, imidazolyl, Benzimidazolyl, pyrazolyl, and pyridonyl groups can be mentioned, but phenyl, oxazolyl, thiazolyl, pyridyl, and thienyl groups are preferable, and phenyl, pyridyl, and thiazolyl are more preferable. Groups are preferred. In addition, examples of the substituent include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, — C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or a branched alkyl, a linear or branched alkenyl having 2 to 8 carbon atoms, a linear or branched alkynyl having 2 to 8 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms) , -SiR ⁵ R ⁶ R ⁷ , -OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , and R ⁷ are linear ones having 1 to 6 carbon atoms) Or branched alkyl, straight-chain or branched haloalkyl having 1 to 3 carbon atoms substituted by one halogen atom, or straight-chain having 1 to 3 carbon atoms substituted by one cyano group Or branched cyanoalkyl and phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms, haloalkenyl (the same or different, a linear or branched alkenyl group having 2 to 6 carbon atoms and substituted with 1 to 4 halogen atoms) ), Haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((number of carbon atoms Linear or branched aliphatic hydrocarbon group having 8 to 8 linear or branched alkoxy groups having 1 to 3 carbon atoms substituted by 1 or 2 acyl groups represented by -CO- ), Acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O—, which is substituted with 1 or 2 acyloxy groups. 1 to 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 3 carbon atoms substituted by 1 or 2 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) Linear or branched alkyl group), siloxyalkyl (—OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, halogen atom) Number of carbon atoms replaced by one 1 to 3 linear or branched haloalkyl, 1 to 3 linear or branched cyanoalkyl and phenyl substituted by one cyano group, two or all of which are the same substituted A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a group or all different substituents), hydroxyalkyl (1 carbon atom substituted by 1 or 2 hydroxyl groups) Straight chain or branched alkyl group having 3 to 3 carbon atoms, alkoxyalkyl (a straight chain having 1 to 3 carbon atoms substituted by 1 or 2 straight chain or branched alkoxy group having 1 to 8 carbon atoms). A linear or branched alkyl group), a haloalkoxyalkyl (same or different, linear or branched 1 or 2 haloalkyls having 1 to 4 carbon atoms and substituted with 1 to 9 halogen atoms) C1-C3 linear or branched alkyl group substituted by a alkoxy group), alkylthioalkyl (C1-C8 linear or branched alkyl group substituted by 1 or 2 alkylthio groups) Straight-chain or branched alkyl groups having 1 to 3 carbon atoms) and dialkoxyacetals (dialkoxy in which two straight-chain or branched alkoxy groups having 1 to 8 carbon atoms are substituted with methyl groups) Methyl group), alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by a linear or branched 1 or 2 alkoxy group having 1 to 8 carbon atoms), Cyanoalkyl (C1-C3 linear or branched alkyl group substituted with 1 or 2 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfur Nyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (—CHO), carboxyl (—COOH) , Formamide (—NHCHO), cyclic ether, and cyclic amine, but alkyl (eg, methyl group, ethyl group, n-propyl group, isopropyl group), alkoxy (eg, methoxy group, ethoxy group, n -Propoxy group, isopropoxy group), acylalkoxy (for example, acetylmethoxy group, propionylmethoxy group, acetylethoxy group), halogen (for example, fluorine atom, chlorine atom, bromine atom), cyano, haloalkyl (for example, monophenyl group) Fluoromethyl group, difluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), hydroxyalkyl (eg, hydroxymethyl group, hydroxyethyl group), cyanoalkyl (eg, cyanomethyl group, cyanoethyl group) alkoxyalkyl (eg, methoxymethoxy) Group, ethoxymethoxy group, methoxyethoxy group), haloalkoxyalkyl (for example, monofluoromethoxymethyl group, difluoromethoxymethyl group, trifluoromethoxymethyl group), haloalkoxy (for example, monofluoromethoxy group, difluoromethoxy group, trimethyl group) A fluoromethoxy group), a benzyloxy group, and a phenoxy group are preferred.

Straight chain or branched alkyl having 1 to 6 carbon atoms, straight chain or branched alkenyl having 2 to 8 carbon atoms, straight chain or branched alkynyl having 2 to 8 carbon atoms in R ¹ As cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms, n-butyl group, s-butyl group, t-butyl group, n-hexyl group, 1-propenyl group, 2- Examples thereof include a propenyl group and an isopropenyl group, and an n-butyl group, an s-butyl group, a t-butyl group, a 1-propenyl group and an isopropenyl group are preferable. The substituents include —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC (O) R, —C (O) NHR, —C. (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR , —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (wherein R is a straight chain having 1 to 8 carbon atoms or Branched alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms), —SiR ⁵ R ⁶ R ⁷ , —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or 1 to 6 carbon atoms Is a branched alkyl, a straight or branched haloalkyl having 1 to 3 carbon atoms substituted by one halogen atom, or a straight chain having 1 to 3 carbon atoms substituted by one cyano group Or branched cyanoalkyl and phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, substituted with 1 to 9 halogen atoms) A linear or branched alkyl group having 1 to 4 carbon atoms, haloalkenyl (the same or different, a linear or branched alkenyl group having 2 to 6 carbon atoms and substituted with 1 to 4 halogen atoms) ), Haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms), acylalkoxy ((1 carbon atom) 8 linear or branched aliphatic hydrocarbon group) 1- to 3-carbon linear or branched alkoxy group substituted by 1 or 2 acyl groups represented by —CO— An acyloxyalkyl ((a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— represented by 1 or 2 acyloxy groups substituted by 1 to 2 carbon atoms. 3 linear or branched alkyl groups), alkylsulfonylalkyl (1 to 3 carbon atoms substituted by 1 or 2 linear or branched alkylsulfonyl groups having 1 to 8 carbon atoms) Linear or branched alkyl group), siloxyalkyl (—OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, halogen atom 1) Number of carbon atoms substituted by 1 1 to 3 linear or branched haloalkyl, linear or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl substituted by one cyano group, and two or all are the same substituents A linear or branched alkyl group having 1 to 3 carbon atoms substituted by all or different substituents), hydroxyalkyl (1 to 2 carbon atoms substituted by 1 or 2 hydroxyl groups) 3 straight-chain or branched alkyl groups), alkoxyalkyl (straight-chain or straight-chain 1 to 3 carbon atoms substituted by 1 or 2 straight-chain or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group), haloalkoxyalkyl (same or different, linear or branched haloal having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) 1- to 3-carbon linear or branched alkyl group substituted by a xy group), alkylthioalkyl (substituted by 1- to 8-carbon linear or branched alkylthio group) Straight-chain or branched alkyl groups having 1 to 3 carbon atoms) and dialkoxyacetals (dialkoxy in which two straight-chain or branched alkoxy groups having 1 to 8 carbon atoms are substituted with methyl groups) Methyl group), alkoxyalkoxy (a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by a linear or branched 1 or 2 alkoxy group having 1 to 8 carbon atoms), Cyanoalkyl (C1-C3 linear or branched alkyl group substituted by 1 or 2 cyano groups), halogen, cyano, nitro, amino, hydroxy, pentahalosulfa Benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (—CHO), carboxyl (—COOH) , Formamide (—NHCHO), cyclic ether, and cyclic amine, but alkoxycarbonyl (eg, methoxycarbonyl group, ethoxycarbonyl group), halogen (eg, fluorine atom, chlorine atom, bromine atom), cyano, Hydroxyalkyl (eg, hydroxymethyl, hydroxyethyl), alkoxyalkyl (eg, methoxymethyl, ethoxymethyl, methoxyethyl), haloalkyl (eg, monofluoromethyl, di Fluoromethyl group, trifluoromethyl group, heptafluoroisopropyl group), haloalkoxy (eg, monofluoromethoxy group, difluoromethoxy group, trifluoromethoxy group), haloalkoxyalkyl (eg, monofluoromethoxymethyl group, difluoromethoxymethyl) Group, trifluoromethoxymethyl group), cyanoalkyl (for example, cyanomethyl group, cyanoethyl group), phenyl group, pyridyl group, furyl group, thiazolyl group, and pyrimidinyl group are preferable.

—SiR ⁵ R ⁶ R ⁷ in R ¹ (R ⁵ , R ⁶ , R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, and having 1 to 6 carbon atoms substituted by one halogen atom. 3 linear or branched haloalkyl, linear or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl substituted by one cyano group, and two or all of them may be the same substituent Examples of the substituents may be trimethylsilyl group, triethylsilyl group, triisopropylsilyl group, t-butyldimethylsilyl group, t-butyldiphenylsilyl group, chloromethyldimethylsilyl group, and cyanopropyldimethylsilyl group. However, a trimethylsilyl group and a triethylsilyl group are preferable.

R ² is preferably a hydrogen atom or a cyano group, and the linear or branched alkyl having 1 to 8 carbon atoms is preferably a methyl group or an ethyl group, and a linear or branched group having 2 to 8 carbon atoms. As the alkenyl, ethynyl group and propenyl group are preferable.

R ² includes —C (O) OR, —C (O) NHR, —CONR ₂ (wherein R is a linear or branched alkyl having 1 to 6 carbon atoms, 2 to 8 linear or branched alkenyl, linear or branched alkynyl having 2 to 8 carbon atoms or cycloalkyl having 3 to 8 carbon atoms), phenyl group, and heteroaryl group. A phenyl group is preferred.

Examples of the halogen atom for R ² include a chlorine atom, an iodine atom, a bromine atom, and a fluorine atom, with a chlorine atom and a fluorine atom being preferred.

Examples of the alkoxy group for R ² include a methoxy group, an ethoxy group, an n-propoxy group, and an isopropoxy group, and a methoxy group and an ethoxy group are preferable.

As the haloalkyl group in R ² , a monofluoromethyl group, a difluoromethyl group, and a trifluoromethyl group are preferable, and as the haloalkoxy group, a monofluoromethoxy group, a difluoromethoxy group, and a trifluoromethoxy group are preferable.

R ³ is preferably a methyl group or an ethyl group as the linear or branched alkyl having 1 to 8 carbon atoms.

R ³ includes —C (O) R, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a linear or branched group having 1 to 6 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms), a benzyl group, Although a phenethyl group, a phenyl group, and a heteroaryl group can be mentioned, an acetyl group is preferable.

(R ⁴⁾ a hydrogen atom as R ⁴ in _n, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, propargyloxy Group, benzyl group, benzyloxy group, heteroaryl group or phenyl group can be mentioned, and a quinazoline ring in which R ⁴ is a hydrogen atom or a fluorine atom is preferred.

In the present invention, the term “alkyl” represents a linear or branched alkyl group having 1 to 8 carbon atoms, such as a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, Examples thereof include an isobutyl group, a s-butyl group, a t-butyl group, an n-pentyl group, an isopentyl group, a neopentyl group, an n-hexyl group, an n-heptyl group, and an n-octyl group.

In the present invention, the term “alkenyl” refers to a linear or branched alkenyl group having 2 to 8 carbon atoms, such as ethenyl group, 1-propenyl group, 2-propenyl group, isopropenyl group, 1- Examples thereof include a butenyl group, a 2-butenyl group, and a 3-butenyl group.

In the present invention, the term “alkynyl” refers to a linear or branched alkynyl group having 2 to 8 carbon atoms, such as an ethynyl group, a 2-propynyl group, a 2-butynyl group, or a 3-butynyl group. Etc.

In the present invention, the term “cycloalkyl” refers to a cycloalkyl group having 3 to 8 carbon atoms, and examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, and a cyclohexyl group.

In the present invention, the term “cycloalkenyl” refers to a cycloalkenyl group having 3 to 8 carbon atoms, such as 1-cyclopentyl group, 2-cyclopentyl group, 3-cyclopentyl group, 1-cyclohexyl group, 2-cyclohexyl group. And a 3-cyclohexyl group.

In the present invention, the term “heteroatom” includes a nitrogen atom, an oxygen atom and a sulfur atom.

In the present invention, the term “halogen” includes fluorine, chlorine, bromine and iodine.

In the present invention, the term “halo” in “halo...” (For example, “haloalkyl”) includes fluorine, chlorine, bromine and iodine.

In the present invention, the term “haloalkyl” is the same or different and represents a linear or branched alkyl group having 1 to 4 carbon atoms which is substituted with 1 to 9 halogen atoms. Examples thereof include a methyl group, a monochloromethyl group, a monobromomethyl group, a difluoromethyl group, a trifluoromethyl group, a pentafluoroethyl group, an n-heptafluoropropyl group, and an isoheptafluoropropyl group.

In the present invention, the term “haloalkenyl” refers to a linear or branched alkenyl group having 2 to 6 carbon atoms which is the same or different and is substituted with 1 to 4 halogen atoms. A 2-difluoroethenyl group, a 2,2-difluoroethenyl group, a 3,3-difluoro-2-propenyl group, and the like can be given.

In the present invention, the term “alkoxy” refers to an (alkyl) -O— group in which the alkyl moiety has the above meaning, for example, a methoxy group, an ethoxy group, an n-propoxy group, an isopropoxy group, an n-butoxy group. , S-butoxy group, t-butoxy group and the like.

In the present invention, the term “haloalkoxy” refers to a (haloalkyl) -O— group in which the haloalkyl moiety has the above meaning, for example, a monofluoromethoxy group, a difluoromethoxy group, a trifluoromethoxy group, 2,2-difluoro An ethoxy group, a 2,2,2-trifluoroethoxy group, etc. can be mentioned.

In the present invention, the term “acyl”, or the term “acyl” in acylalkoxy, the term “acyl” in acyloxyalkyl, and the term “acyl” in acyloxy are all (directly having 1 to 8 carbon atoms). A chain or branched aliphatic hydrocarbon group) -CO-, and examples thereof include an acetyl group, a propionyl group, a butyryl group, and an isobutyryl group. In the present application, the aliphatic hydrocarbon group means alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, and cycloalkynyl.

In the present invention, the term “acylalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 2 acyl groups as described above. Group, acetylethoxy group, acetylpropoxy group and the like.

In the present invention, the term “acyloxy” represents (a linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O— group, for example, an acetoxy group, a propionyloxy group, Examples thereof include an isopropionyloxy group and a pivaloyloxy group.

In the present invention, the term “acyloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 acyloxy groups shown above, for example, acetoxymethyl A group, an acetoxyethyl group, an acetoxypropyl group, and the like.

In the present invention, the term “alkylsulfonyl” refers to an (alkyl) -SO ₂ — group in which the alkyl moiety has the above meaning, for example, methylsulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, or isopropylsulfonyl Groups and the like.

In the present invention, the term “alkylsulfonylalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 alkylsulfonyl groups shown above, for example, A methylsulfonylmethyl group, a methylsulfonylethyl group, or a methylsulfonylpropyl group can be exemplified.

In the present invention, the term “siloxy” refers to —OSiR ⁵ R ⁶ R ^{7, where} R ⁵ , R ⁶ , and R ⁷ are substituted with a straight or branched alkyl group having 1 to 6 carbon atoms and one halogen atom. Straight-chain or branched haloalkyl having 1 to 3 carbon atoms, straight-chain or branched cyanoalkyl having 1 to 3 carbon atoms substituted by one cyano group, and phenyl, For example, trimethylsiloxy group, triethylsiloxy group, triisopropylsiloxy group, t-butyldimethylsiloxy group, t-butyldiphenylsiloxy group, etc. be able to.

In the present invention, the term “siloxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by the above-mentioned siloxy group, such as trimethylsiloxymethyl group, trimethylsiloxy Examples thereof include an ethyl group, a trimethylsiloxypropyl group, a triethylsiloxymethyl group, and a t-butyldimethylsiloxy group.

In the present invention, the term “hydroxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 hydroxyl groups, such as hydroxymethyl group, hydroxyethyl group, Group, or a hydroxypropyl group.

In the present invention, the term “alkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 alkoxy groups as described above, for example, methoxymethyl A group, an ethoxymethyl group, a propoxymethyl group, or an isopropoxymethyl group.

In the present invention, the term “alkylthio” refers to an (alkyl) -S— group in which the alkyl moiety has the above meaning, and examples include a methylthio group, an ethylthio group, or a propylthio group.

In the present invention, the term “alkylthioalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 alkylthio groups as described above, for example, methylthiomethyl A group, an ethylthiomethyl group, a methylthioethyl group, or an ethylthioethyl group.

In the present invention, the term “dialkoxyacetal” refers to a dialkoxymethyl group in which the above-mentioned alkoxy group is substituted by two methyl groups, such as a dimethoxymethyl group, a diethoxymethyl group, or a dipropoxymethyl group. Can be mentioned.

In the present invention, the term “alkoxyalkoxy” refers to a linear or branched alkoxy group having 1 to 3 carbon atoms substituted by 1 to 2 alkoxy groups as described above, for example, methoxymethoxy Group, methoxyethoxy group, methoxypropoxy group and the like.

In the present invention, the term “haloalkoxyalkyl” refers to a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 haloalkoxy groups as described above. A monofluoromethoxymethyl group, a difluoromethoxymethyl group, a trifluoromethoxymethyl group, etc. can be mentioned.

In the present invention, the term “cyanoalkyl” represents a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 cyano groups, such as a cyanomethyl group, a cyanoethyl group, Or a cyanopropyl group etc. can be mentioned.

In the present invention, “phenyl”, “thienyl”, “pyridyl”, “oxazolyl”, “furanyl”, “thiazolyl”, “naphthyl”, “pyrimidinyl”, “benzothiazolyl”, “benzoxazolyl”, “benzodi” “Oxolyl” may have one or more substituents which may be the same or different, and may not have a substituent.

In the present invention, the term “phenoxy” includes a phenoxy group having one or more substituents which may be the same or different, and an unsubstituted phenoxy group.

In the present invention, the term “benzyl” includes a benzyl group having one or more substituents which are the same or different and an unsubstituted benzyl group.

In the present invention, the term “phenethyl” includes phenethyl groups having one or more substituents which are the same or different and unsubstituted phenethyl groups.

In the present invention, the term “benzyloxy” includes a benzyloxy group having one or more substituents which are the same or different and an unsubstituted benzyloxy group.

In the present invention, the term “propargyl” includes propargyl groups having a substituent at the alkyne end and unsubstituted propargyl groups.

In the present invention, the term “propargyloxy” includes a propargyloxy group having a substituent at the alkyne end and an unsubstituted propargyloxy group.

In the present invention, the term “heteroaryl” includes oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, quinolyl, isoquinolyl, indolyl, isoindolyl, imidazolyl, pyrazolyl, pyridyl, furyl, thienyl, pyrrolyl. . These groups may have one or more substituents which may be the same or different, and may not have a substituent.

In the present invention, the term “cyclic ether” includes epoxy, oxetane, tetrahydrofuran, tetrahydropyran, dioxolane, and dioxane.

In the present invention, the term “cyclic amine” includes pyrrolidinyl, imidazolidinyl, pyrazolidinyl, piperidinyl, piperazinyl, morpholinyl.

In the present invention, the term “imide” includes a chain imide and a cyclic imide.

Since the compound of the present invention represented by the formula [I] has an amino group, an acid addition salt derived therefrom is also included in the present invention.

Examples of acids that form acid addition salts include inorganic acids such as hydrochloric acid, hydrobromic acid, nitric acid, sulfuric acid, and phosphoric acid, formic acid, oxalic acid, fumaric acid, adipic acid, stearic acid, oleic acid, and aconitic acid. Carboxylic acid, methanesulfonic acid, benzenesulfonic acid, sulfonic acid such as p-toluenesulfonic acid, or saccharin.

In the compound of the present invention represented by the formula [I], R ² is —R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is the number of carbon atoms) Linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or 3 to 3 carbon atoms 8 cycloalkyl), hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 to 2 hydroxyl groups), alkoxyalkyl (having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by a linear or branched 1 to 2 alkoxy group), phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different) 1 to 9 halogen atoms Substituted or straight chain or branched alkyl group having 1 to 4 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Any of the individual optical isomers, racemates, or mixtures thereof derived from the asymmetric carbon atom generated in the case of (like or branched alkoxy groups) are included in the present invention.

Further, acyloxy, halogen, wherein R ³ of the compound of the present invention represented by the formula [I] is represented by (C 1-8 linear or branched aliphatic hydrocarbon group) —CO—O— Any of the individual optical isomers, racemates or mixtures thereof derived from the asymmetric carbon atom generated in the case of alkyl having 1 to 6 carbon atoms substituted with an atom or a hydroxyl group is included in the present invention.

The compound [I] of the present invention represented by the following formula comprises, for example, a chloroquinazoline derivative represented by the general formula [II] and a 3-butynylamine derivative represented by the general formula [III] as shown in the following reaction process formula. It can be produced by reacting in the presence of a base and a solvent.

(Wherein R ¹ , R ² , R ³ and (R ⁴ ) _n are as defined above.)
The type of the solvent is not particularly limited as long as it does not directly participate in this reaction. For example, benzene, toluene, xylene, methylnaphthalene, petroleum ether, ligroin, hexane, chlorobenzene, dichlorobenzene, chloroform, dichloroethane, Aromatic, aliphatic or alicyclic hydrocarbons such as trichlorethylene, ethers such as tetrahydrofuran, dioxane, diethyl ether, nitriles such as acetonitrile, propionitrile, acetone , Ketones such as methyl ethyl ketone, amide compounds such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone, sulfoxy compounds such as dimethyl sulfoxide, urea such as N, N-dimethylimidazolidinone Compounds, sulfolane, or can be exemplified such as a mixture of the solvent, N, N- dimethylformamide, N, N- dimethylacetamide, amide compounds such as N- methylpyrrolidone is preferred.

The amount of the solvent used can be such that the compound [II] is 5 to 80% by weight, but preferably 10 to 70% by weight.

The type of base is not particularly limited, and organic and inorganic bases such as tertiary amines (such as triethylamine), organic bases such as DBU, alkali metal and alkaline earth metal hydrides, hydroxides, carbonates, Although inorganic bases, such as hydrogencarbonate, can be mentioned, organic bases, such as tertiary amine (triethylamine etc.) and DBU, are preferable.

The amount of the base to be used is 1.0 to 5.0 mol, preferably 1.2 to 2.0 mol, relative to 1.0 mol of compound [II].

The amount of the raw material compound used is 1.0 to 5.0 mol of compound [III] with respect to 1.0 mol of compound [II], preferably 1.0 to 1.2 mol.

The reaction temperature is not particularly limited, but is within the temperature range from room temperature to the boiling point of the solvent used, and preferably 60 to 110 ° C.

The reaction time varies depending on the concentration and temperature, but is usually 0.5 to 8 hours.

The compound [I] produced as described above is subjected to usual post-treatments such as extraction, concentration and filtration after completion of the reaction, and is appropriately purified by known means such as recrystallization and various chromatography as necessary. can do.

When the compound [I] produced as described above is a terminal alkyne (R ¹ = H, [IV]), a substituent may be introduced using the Sonogashira reaction or the like. Is possible.

(Wherein R ¹ is phenyl, heteroaryl, alkenyl, R ² , R ³ and (R ⁴ ) _n are as defined above.)
Compound [II] used in this synthesis method can be produced, for example, by the method shown in the following formula.

(Wherein (R ⁴ ) _n has the same meaning as described above.)
The 3-butynylamine derivative [III] used in this synthesis can be a commercially available product. If necessary, it can be produced, for example, according to the method described below. However, the method described below does not limit the scope of the present invention.
(Synthesis method 1)
Formation after N- (3-butynyl) methylamine derivative [VIII] and Sonogashira reaction with iodide or phenyl bromide, iodide, bromide or heteroaryl chloride, iodide or alkenyl bromide [V] The 3-butynylamine derivative [III] can be produced by deprotecting the product [IX] with hydrazine or a base, followed by reductive amination.

(Wherein X is iodine, bromine or chlorine, R ¹ is phenyl, heteroaryl, alkenyl, R ² and R ³ are as defined above.)
(Synthesis method 2)
The product [VIII] is synthesized from the substituted butynyl alcohol [X] and the phthalimide [XI] by Mitsunobu reaction. A 3-butynylamine derivative [III] can be produced by amination.

(Wherein X is iodine, bromine or chlorine, R ¹ is phenyl, heteroaryl, alkenyl R ² and R ³ are as defined above.)
(Synthesis method 3)
After the terminal alkyne [XII] is reacted with a Grignard reagent, it is further reacted with ethylene oxide [XIII] to synthesize 3-butynyl alcohol derivative [XIV]. Thereafter, the 3-butynylamine derivative [III] can be produced by subjecting this alcohol to Mitsunobu reaction, deprotection, and reductive amination reaction.

(Wherein X is iodine, bromine or chlorine, R ¹ , R ² and R ³ are as defined above) (Synthesis Method 4)
The 3-butynylamine derivative [III] can be produced by protecting the substituted butynyl alcohol [XIV] with a tosyl group and then reacting with the amine [XVI] in the presence of sodium iodide.

(In the formula, R ¹ , R ² and R ³ are as defined above.)
(Synthesis Method 5)
3-Butynylamine derivative [III] can be produced by subjecting compound [XVII] obtained by oxidizing substituted butynyl alcohol [XIV] to reductive amination reaction with amine [XVI].

(In the formula, R ¹ , R ² and R ³ are as defined above.)
[Control effect]
The term “pest” here includes all pathogenic fungi for agricultural and horticultural plants, all pests and mites for agricultural and horticultural plants.
(Pathogenic fungi against agricultural and horticultural plants)
Examples of pathogenic fungi for agricultural and horticultural plants include algal fungi (Omycetes), ascomycetes (Ascomycetes), imperfect fungi (Deuteromycetes), basidiomycetes (Basidiomycetes), bacteria, and the like, and quinazoline used in the present invention. Derivatives can control plant diseases caused by these pathogenic fungi. Next, specific names of bacteria are given as examples, but are not necessarily limited thereto.

Examples of agricultural and horticultural pathogens include, for example, rice blast (Pyricularia oryzae), rice sesame leaf blight (Cochliobolus miyabeanus), rice coat blight (Rhizoctonia solani), rice idiot (Gibberella fujikuroi), barley powdery mildew (Erysiphe graminis) tritici), wheat powdery mildew (Erysiphe graminis f.sp. hordei), wheat eye spot disease (Pseudocercosporella herpotrichoides), wheat rust (puccinia graminis), wheat anthracnose (Colletotrichum graminicola), wheat leaf blight Disease (Septoria tritici), wheat cloud-shaped disease (Phynchosporium secalis f.sp. Potato gray mold (Botrytis cinerea), azuki bean mildew (Erisiphe pisi), azuki bean brown spot (Cercospora canescens), azuki bean sclerotia (Sclerotinia sclerotiorum), azuki bean anthracnose (Colletotri) chum phaseolorum), common bean brown spot (Cercospora canescens), common bean sclerotia (Sclerotinia sclerotiorum), common bean anthracnose (Colletotrichum lindemuthiamum), common bean gray mold (Botrytis cinerea), soybean anthracnose (Colletotrichum trunc) (Cercospora kikuchii), soybean rust (Phakopsora pachyrhizi), konjac anthracnose (Gloeosporium conjac), konjac brown spot (Septoria perillae), tea anthracnose (Colletotrichum theae-sinensis), spinach brown spot (Cercospora beticola) Anthracnose (Colletotrichum spinaciae), spinach downy mildew (Peronospora effusa), cabbage black spot (Alternaria brassicae), cabbage black soot (Alternaria brassicicola), cabbage mycosis (Sclerotinia sclerotiorum), cabbage gray mold (Botrytis cine) ), Cabbage black rot (Xanthomonas campestris pv. Campestris), radish soft rot (Erwinia carotovora), Komatsuna Gonorrhea (Colletotrichum higginsianum), Sclerotinia sclerotiorum, Chinese cabbage black spot (Alternaria brassicae, Alternaria brassicicola), Pumpkin black spot (Alternaria cucumerina), Pumpkin gray mold (Botrytis cinerea), Pumpkin mildew (Pseudoperonospora cubensis), cucumber powdery mildew (Sphaerotheca fuliginea), cucumber plague (Phytophthora melonis), cucumber brown spot (Corynespora cassiicola), cucumber sclerotia (Sclerotinia sclerotiorum), cucumber black cucumber (Alternaria black cucumber) Diseases (Colletotrichum lagenarium), cucumber vines (Fusarium oxysporum f.sp. .), Cucumber downy mildew (Pseudoperonospora cubensis), Cucumber spotted bacterial disease (Pseudomonas syringae), Watermelon powdery mildew (Sphaerotheca fuliginea) Watermelon plague (Phytophthora cryptogea), watermelon mycosis (Sclerotinia sclerotiorum), watermelon anthracnose (Colletotrichum orbiculare), watermelon downy mildew (Pseudoperonospora cubensis), melon brown spot (Corynespora cassiicola), melon fungal sclerosis (Sclerotinia sclerosis) Melon vine split disease (Fusarium oxysporum f.sp. melonis), melon downy mildew (Pseudoperonospora cubensis), Sengoku wilt disease (Fusarium oxysporum), Sclerotinia sclerotiorum, Poleia cnici-Pole , Shungyiku anthracnose (Gloeosporium chrysanthemi, Gloeosporium carthami), carrot wilt (Fusarium oxysporum), carrot powdery mildew (Erysiphe heraclei), carrot mycosis (Sclerotinia intermedia, Sclerotinia sclerotiorum), carrot black , Carrot black spot (Alternaria radicina), pepper green pepper wilt (Fusarium oxysporum), pepper green pepper powdery mildew (Oidiopsis sicula) , Pepper, green pepper (Phytophthora capsici), pepper green pepper (Sclerotinia sclerotiorum), pepper green pepper anthracnose (Colletotrichum gloeosporioides), pepper red pepper gray mold (Botrytis cinerea) sp. lycopersici), tomato powdery mildew (Oidiopsis sicula), tomato plague (Phytophthora infestans), tomato mycosis (Sclerotinia sclerotiorum), tomato gray mold (Botrytis cinerea), tomato leaf mold (Fulvia fulva), eggplant plague (Phytophthora infestans), eggplant brown spot disease (Thanatephorus cucumeris), eggplant brown rot disease (Phytophthora capsici), eggplant mycorrhizal disease (Sclerotinia sclerotiorum), eggplant brown spot disease (Alternaria solani), strawberry yellow rot (Fusarium oxysporum), strawberry Wilt (Verticillium dahliae), strawberry powdery mildew (Sphaerotheca humuli), strawberry plague (Phytophthora nicotianae var. Parasitica), strawberry fruit rot (Pythium ultimum var. ultimum), strawberry mycosis (Sclerotinia sclerotiorum), strawberry black spot (Alternaria alternata), strawberry snake eye disease (Mycosphaerella fragariae), strawberry anthracnose (Colletotrichum acutatum, Glomerella cingulata), strawberry gray mold (Botrytis cinerea), asparagus Gas brown spot (Cercospora asparagi), Asparagus stem blight (Phomopsis asparagi), Asparagus rust (Puccinia asparagi-lucidi), Asparagus anthracnose (Colletotrichum gloeosporioides), Asparagus gray mold (Botrytis cinerea), onion Phytophthora nicotianae, onion yellow spot (Cladosporium allii-cepae), onion dry rot (Fusarium oxysporum f.sp. cerae), onion sclerotia (Sclerotinia sclerotiorum), onion black spot leaf blight (Septoria alliacea) False black spot (Alternaria porri), onion rust (Puccinia allii), onion sclerotia (Puccinia allii), onion sclerotia (Botrytis squamosa), onion white plague ( Phytophthora parri), onion anthracnose (Colletotrichum circinans), onion black spot (Alternaria sp.), Onion gray mold (Botrytis cinerea), onion gray rot (Botrytis allii), onion leaf blight (Pleospora herbarum), onion Downy mildew (Peronospora destructor), leek rust (Puccinia allii), leek white leaf blight (Botrytis byssoidea), leek plague (Phytophthora nicotianae), leek wilt (Fusarium oxysporum), leek black astringency (Mycosphaerella allicina), Leek black spot blight (Septria alliacea), leek black spot (Alternaria porri), leek sclerotia nuclear disease (Sclerotinia allii), leek rust (Puccinia allii), leek sclerotia nuclear rot (Botrytis squamosa), leek white Pests (Phythoththora parri), leek anthracnose (Colletotrichum circinans), leek downy mildew (Peronospora destructor), mango anthracnose (Colletotrichum gloeosporioides), oyster powdery mildew (Phyllactinia kakikola), oyster-contaminated fruit diseases (Colletotrichum smel) sp.), oyster keratosis (Cercospora kakivora), oyster spotted leaf disease (Cercosporakaki), oyster brown spot disease (Macrophoma kaki), oyster black spot disease (Fusicladium levieri), oyster black spot disease (Phomopsis kakivora), oyster black spot disease (Pseudocercospora fuliginosa), oyster shrinkage Leaf disease (Physalospora kaki), oyster soot disease (Aureobasidium pullulans, Capnophaeum fuliginodes, Cladosporium herbarum, Microxyphium sp., Scorias communis, Tripospermum juglandis) Oyster soot spot disease (Zygophiala jamaicensis), Disease (Botrytis cinerea), oyster leaf blight (Pestalotia diospyri), oyster leaf anthracnose (Glomerella cingulata), oyster leaf defoliation (Mycosphaerella nawae), ume powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), ume branch disease (Botryosphaeria dothidea), Sclerotinia sclerotiorum, Black scab (Cladosporium carpophilum), Prunus white rust (Leucotelium pruni-persicae), Plum white rot (Rosellinia necatrix), Plum heart rot (Fusarium lateritium) ), C Pneumatosis (Pseudocercospora circumscissa), scab (Sphaceloma pruni-domesticae), plum anthracnose (Glomerella cingulata), ume gray mold (Botrytis cinerea), ume blight (Monilinia fructicola, Monilinia laxa), ume leaves Anthracnose (Glomerella mume), sugar beetle sclerotia (Sclerotinia sclerotiorum), powdery mildew (Podosphaera tridactyla), sugar beet fungus (Rhizopus nigricans), sugar beet rot (Glomerella cingulata), cine Bot ry tis , Sugar beet blight (Monilinia fructicola), pear powdery mildew (Phyllactinia mali), pear plague (Phytophthora cactorum, phytophthora syringae), pear black scab (venturia pirina), pear anthracnose (glolepotrichum) Red star disease (Gymnosporangium asiaticum), pear powdery mildew (Phyllactinia pyri), pear plague (Phytophthora cactorum, Phytophthora syringae), pear black star disease (Venturia nashicola), pear Spot disease (Alternaria kikuchiana), pear soot spot (Leptothyrium pomi), pear anthracnose (Glomerella cingulata), pear gray mold (Botrytis cinerea), pear ash scab (Monilinia fructigena), pear leaf anthracnose (Colletotrichum gloeosporioides) , Pear anthracnose (Physalospora piricola), peach red mold (Fusarium oxysporum, Gibberella zeae), peach powdery mildew (Podosphaera tridactyla, Sphaerotheca pannosa), peach fungus nuclear disease (Sclerotinia sclerotiorum), peach black pus gri ), Peach black spot (Cladosporium carpophilum), peach white rust (Leucotelium pruni-persicae), peach scab (Stenella sp.), Peach perforation (Pseudocercospora circumscissa, Phyllosticta persicae), peach anthracnose (Gloeocolor), Peach gray mold (Botrytis cinerea), Peach ash scab (Monilinia fructicola), Pomohomopsis rot (Phomopsis sp.), Apple scab (Gymnosporangium yamadae), Apple powdery mildew (Podosphaera leucotricha), Pseudomonas rot (P hytophthora cactorum, phytophthora cambivola, Phytophthora syringae), apple brown spot (Diplocarpon mali), apple ring-leaf blight (Cristulariella moricola), apple black spot (Venturia inaequalis), apple soot spot (Zygophiala jamaicensis), apple charcoal (Glomerella cingulata), apple gray mold (Botrytis cinerea), apple spotted leaf (Alternaria alternata), grape powdery mildew (Uncinula necator), grape shoot blight (Sclerotinia sclerotiorum), grape late rot (Glomerella cingulata) ), Grape brown spot (Pseudocercospora vitis), grape brown leaf blight (Briosia ampelophaga), grape black rot (Elsinoe ampelina), grape black rot (Phyllosticta ampelicida), grape vine split (Phomopsis viticola), grape Downy mildew (Plasmopara viticola), chestnut anthracnose (Glomerella cingulata), chestnut soot (Capnodium salicinum), chestnut brown spot (Morenoella quercina), chestnut powdery mildew (Microsphaera alphitoides), chestnut leaf blight (Monochaetia mono) chaeta), citrus gray mold (Botrytis cinirea), citrus brown rot (Phytophthora citrophthora), citrus black spot (Diaporthe citri), citrus yellow spot (Mycosphaerella citri, Mycosphaerella horii), citrus scab (Elsinoe fakti) Examples include freckles (Mycosphaerella pinodes), citrus anthracnose (Colletotrichum gloeosporioides), and citrus rust (Colletotrichum gloeosporioides).
(Pests and mites on agricultural and horticultural plants)
Examples of pests and mites on agricultural and horticultural plants include the order of Hemiptera, Thysanoptera, Lepidoputera, Acari, etc. The quinazoline derivatives used in the present invention are Plant damage caused by these pests and mites can be controlled. Next, specific pests, ticks and the like are given as examples, but not necessarily limited thereto.

Pests, mites, etc. include, for example, Plutella xylostella, Agrotis ipsilon, Abratis segetum, Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea), Tobacco Bad Worm (Heliothis virescens), Mamestra brassicae, Naranga aenescens, Tamanaginawaba (Plusia nigrisigna), Ayayoto (Pseudaletia separata), Spodoptera exigua, Spodoptera exigua, Spodoptera exigua, Spodoptera exigua , Fall army worm (Spodoptera frugiperda), Southern army worm (Spodoptera eridania), Tobacco horn worm (Manduca sexta), Grapeberry moss (Endopiza viteana), Ginmon leaf moth (Lyonetia prunifoliella malinella), Golden leaf moth (Phella moth) (Phylloc nistis citrella), cotton beetle (Pectinophora gossypiella), peach squirrel (Carposina niponensis), apple wolfberry (Adoxophyes orana faciata), tea wolfberry (Adoxophyes honmai), chahamaki (Homona magnamina), ydrin molesta, Chilosuppressalis, Cnaphalocrocis medinalis, Hellula undalis, European corn borer (Ostrinia nubilalis), Soybean looper (Pseudoplusia includens), Nigeria cinnamon (Trichoia) ), White-tailed butterfly (Pieris rapaecrucivora), Lepidoptera, Parnara guttata, etc. Epilachna varivestis, Melanonotus tamsuyensis, tobacco beetle (Lasioderma serricorne), Epuraea domina, Henosepilachna vigintioctopunctata, Tribolium castaneum, Anoplophora malasiaca, Monochamus alternatus, Azuki beetle (Callosobruchus chinensis), Urihamushi (Aulacophora femoralis), Oedma orylae Cotton weevil (Anthonomus grandis), Green weevil (Ethinocnemus squameus), Alfalfa weevil (Hypera postica), Green weevil (Lissorhoptrus oryzophilus), Beast weevil (Sitophilus zeamais), Shivao weevil (tus vest) Insect insects such as Sitophilus granarius, Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera), Northern corn rootworm (Diabrotica barberi), Paederus fuscipes, etc. (Eurydema rugosa), Shirahoshi beetle (Eysarcoris ventralis), Hedgehog beetle (Halyomorpha mista), Southern stink bug (Nezara viridula), Spider helicopter (Leptocorisa chinensis), Hosoheri stink bug (Riptortus clam) ), Stephanitis pyrioides, Epiacanthus stramineus, Empoasca onukii, Potato leaf hopper (Empoasca fabae), Nephotettix cinctinceps, telo del pha ilaparvata lugens), white-spotted plant (Sogatella furcifera), citrus white lice (Trioza erytreae), pear lice (Psylla pyrisuga), tobacco white lice (Bemisia tabaci), silver-leaf whitefly (Bemisia argentifolii), tri-white ale-on-white Aphids (Aphis gossypii), Yukiyanagi Aramushi (Aphis pomi), Peach Aphid (Myzus persicae), Paramecium aphid (Drosicha corpulenta), Icerya purchasi, eucalyptus eucalyptus (Planococcus citri) ), Ruby Beetle (Ceroplastes rubens), Carabidae (Unaspis yanonensis), Bugs (Cimex lectularius), etc. Thrips palaids such as Scirtothrips dorsalis, Thrips palmi, Thrips tabaci, Dacus dorsalis, Dacus cucurbitae, H ), Eggplant leaf fly (Liriomyza bryoniae), bean leaf fly (Liriomyza trifolii), fly fly (Hylemya platura), apple magot (Rhagoletis pomonella), fly fly (Mayetiola destructor), house fly (Musca domestica), sand fly cali (S Melophagus ovinus), Hypoderma lineatum, Bullflies (Hypoderma bovis), sheep flies (Oestrus ovis), tsetse flies (Glossina palpalis, Glossina morsitans), yellow-bellied (Prosimulium yezoensis), bullfly (Tabanusmatous) Leptocono ps nipponensis), Culex pipiens pallens, Aedes albopicutus, Aedes aegypti, Anopheles hyracanus sinesis (Apethymus kros) Neodiprion sertifer), Guntai ant (Eciton burchelli, Eciton schmitti), Black-tailed ant (Camponotus japonicus), Giant hornet (Vespa mandarina), Bulldog ant (Myrmecia spp.), Fire ant (Solenopsis spp.), Pharaoh ant (Monomium pharaoh ant) Bee-eyed insects, black cockroach (Periplaneta fuliginosa), cockroach (Periplaneta japonica), German cockroach (Blattella germanica), etc. yezoensis), mackerel grasshopper (Schistocerca g) butterfly pests such as regaria, termites (Coptotermes formosanus), termites (Reticulitermes speratus), termites pests such as the Odontotermes formosanus, cat fleas (Ctenocephalidae felis), human fleas (Pulex irritans) Flea insects such as Xenopsylla cheopis, chick larvae (Menacanthus stramineus), larvae insects such as bovic larvae (Bovicola bovis), cattle lice (Haematopinus eurysternus), pork lice (Haematopinus suis), cow leopard (Lino capsicum) Lice etc.). As for the mites, spider mites (Panonychus citri), apple spider mite (Panonychus ulmi), Kanzawa spider mite (Tetranychus kanzawai), spider mite (Tetranychus urticae), etc. Mite (Eriophyes chibaensis), Tulip mite (Aceria tulipae), etc., Mite (Polyphaotarsonemus latus), Mite (Steneotarsonemus pallidus), etc., Mite (Tyrophagus putrescentiae), M. Spider mites such as honeybee mite (Varroa jacobsoni), ticks (Boophilus microplus), ticks (Haemaphysalis longicornis), cucumber mites (Psoroptes ovis), and mite (Sarcoptes scabiei) Etc. In addition, crustaceans such as Armadillidium vulgare, Platylenchus penetrans, Prathylenchus vulnus, potato cyst nematode (Globodera rostochiensis), soybean cyst nematode (Heterodera glycerine) hapla), nematodes such as Meloidogyne incognita, Bursaphelenchus lignicolus, Ponacea canaliculata, slugs (Incilaria bilineata), Acusta despecta siebiana (Acusta despecta sieb Mollusks and the like.
[Pesticides]
The agricultural and horticultural pest control agent of the present invention is particularly effective in sterilizing effect and insecticidal effect, and contains one or more compounds represented by the formula [I] as active ingredients.

The pesticide for agricultural and horticultural use of the present invention represented by the formula [I] is treated by spraying, spraying, applying, etc., an active ingredient, or seeding plant seeds or soil or seeds surrounding the plant Soil, paddy field, hydroponically cultivated water can be treated with active ingredients. Application can take place before or after the plant is infected with the pathogen or before or during the infestation of the pests.

This compound is in the form of normal preparations such as granules, powders, aqueous solvents, oils, emulsions, microemulsions, suspoemulsions, solutions, wettable powders, emulsions, suspensions, tablets, granules It can be used as an agent suitable for agricultural and horticultural pest control agents such as wettable powders, microcapsules, aerosols, pastes, jumbo agents, powders, smoke agents, fumigants and the like. Such embodiments include at least one compound of the invention and a suitable solid or liquid carrier, and, if desired, suitable adjuvants (eg, surfactants) to improve the dispersibility of the active ingredient and other properties. Can be obtained by an ordinary method of mixing with an agent, a solvent and a stabilizer.

Examples of solid carriers or diluents include plant materials (eg, crystalline cellulose, starch, wood flour, cork, coffee husk, etc.), fibrous materials, artificial plastic powders, clays (eg, kaolin, bentonite) , White clay, diatomaceous earth, synthetic hydrous silicon oxide, fusami clay, acid clay, etc.), talc and inorganic substances (eg vermiculite, montmorillonite, pumice, sulfur powder, apatite, mica, sericite, quartz powder, activated carbon, calcium carbonate, etc.) , Polymer compounds (polyvinyl chloride, petroleum resin, etc.), chemical fertilizers (eg, ammonium sulfate, phosphorous acid, ammonium nitrate, ammonium chloride, calcium chloride, urea, etc.). Liquid carriers and diluents include water, alcohols (eg, methanol, ethanol, isopropanol, cyclohexanol, etc.), ketones (eg, acetone, methyl ethyl ketone, cyclohexanone, etc.), ethers (eg, ethyl cellosolve, butyl cellosolve) , Dioxane, etc.), aromatic hydrocarbons (eg, benzene, toluene, xylene, ethylbenzene, methylnaphthalene, etc.), aliphatic hydrocarbons (eg, kerosene, paraffin, etc.), and swells (eg, isopropyl acetate, benzyl acetate, etc.) Nitriles, amides (eg, N, N-dimethylformamide, dimethyl sulfoxide, etc.), halogenated hydrocarbons (eg, chlorobenzene, trichloroethylene), and the like.

Examples of gaseous carriers, ie, propellants, include carbon dioxide gas, butane gas, and fluorocarbon.

Examples of surfactants include various anionic surfactants and nonionic surfactants conventionally used in the field of agrochemical formulations. Examples of the anionic surfactant include sulfonic acid-based surfactants such as alkyl sulfonic acid, alpha olefin sulfonic acid, lignin sulfonic acid, alkylbenzene sulfonic acid, alkyl naphthalene sulfonic acid, naphthalene sulfonic acid formalin condensate, and dialkyl sulfosuccinate. Agents and salts thereof, polyoxyethylene alkyl ether sulfate, polyoxyethylene alkyl allyl ether sulfate, polyoxyethylene styryl phenyl ether sulfate, polyoxyethylene phenyl alkyl allyl ether sulfate, polyoxyalkylene glycol sulfate, higher alcohol sulfate, fatty acid ester Sulfate surfactants such as sulfate and phenylphenol (EO) sulfate and the like Salts of polyoxyethylene alkyl ether phosphate, polyoxyethylene alkyl allyl phosphate, phenylphenol (EO) phosphate ester salt, polyoxyethylene phenyl alkyl allyl ether phosphate, higher alcohol phosphate, polyoxyethylene tribenzylphenol phosphate, etc. Surfactants and salts thereof, higher fatty acid salts, polycarboxylic acid type surfactants and salts thereof, and the like. The salts in the above surfactants include salts of sodium, potassium, magnesium, calcium, ammonium, ethanolamine, diethanolamine, triethanolamine, various amines and the like. Examples of the nonionic surfactant include polyoxyethylene alkyl allyl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene alkyl ether, polyoxyethylene phenyl alkyl allyl ether, polyoxyethylene sorbitan fatty acid ester, polyoxyethylene glycol. , Polyoxyethylene alkyl ester, polyoxyethylene polyoxypropylene block copolymer, polyoxyalkylene glycol, alkyne diol (acetylene glycol), alkynylene polyoxyethylene diol, sorbitan fatty acid ester, alkyl aryl ether formalin condensate, etc. it can.

Stabilizers include isopropyl phosphate mixture, tricresyl phosphate, tall oil, epoxy oil, surfactants, fatty acids and esters thereof. In addition to the above components, the compounds of the present invention can be formulated in admixture with other fungicides, insecticides, herbicides, or fertilizers.

Generally, the above-mentioned preparation contains 1 to 95% by weight, preferably 1 to 50% by weight, of at least one compound [I] of the present invention. These preparations can be used alone or diluted, and the compound [I] of the present invention is used in an amount of about 1 to 5 kg / ha, preferably about 2 to 100 g / ha, usually about 1 to 50000 ppm, preferably about Used at a concentration of 50-1000 ppm.

The compound of the present invention represented by the formula [I] can be used alone or as a preparation thereof, but a bactericidal / fungicidal agent, bactericidal agent, acaricide, nematicide, insecticide, biological pesticide, A mixture of herbicides, plant hormones, plant growth regulators, synergists, attractants, repellents, pigments, fertilizers, etc., or a mixture of one or more selected from those active ingredients The preparation can also be used as a pest control agent. There, it can be expected that the action, pests to be controlled, expansion of the appropriate period of use, or reduction of dosage, synergistic effect, or prevention of development of resistance, etc. Shinogi, cooperative medicinal effects with joint ingredients are achieved.

Examples of co-components in the mixture include the following compounds.

Of the joint ingredients in the mixture, many of the fungicides and fungicides, bactericides, insecticides, acaricides, nematicides, biopesticides, pheromones, natural fungicides, and natural insecticides have been developed and marketed. Pesticide Handbook (2009) published by the Japan Plant Protection Association, Agricultural Handbook (2009), Kumiai Agricultural Guidebook (2009) published by the National Federation of Agricultural Cooperatives, and SHIBUYA INDEX published by the Federation (2009).

Examples are shown below, but are not limited thereto.

Examples of bactericides include SH synthesis inhibitory active compounds, nucleic acid biosynthesis inhibitory active compounds, spindle formation inhibitory active compounds, benzanilide compounds, strobilurin compounds, other electron transport inhibitory compounds, amino acid biosynthesis inhibitory active compounds, Sterol biosynthesis-inhibiting active compound, cell wall synthesis-inhibiting active compound, lipid biosynthesis-inhibiting active compound, glucan biosynthesis-inhibiting active compound, melanin biosynthesis-inhibiting active compound, host resistance-inducing compound, compounds having other or unclear effects, etc. Can be mentioned.

Compounds that inhibit SH synthesis: chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate, ferbam ), Nabam, maneb, mancozeb, metiram, propineb, polycarbamate, thiram, ziram, zineb, oxidized Cupric® oxide, cupric hydroxide (Copper® hydroxide), basic copper chloride (Copper® oxychloride), anhydrous copper sulfate (Copper® sulfate® (anhydride)), copper sulfate (copper® sulfate), sulfur (Sulfur), etc. .

Nucleic acid biosynthesis inhibiting active compounds: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid, etc.

Spindle yarn formation inhibitory active compounds: benomyl, carbendazim, dietofencarb, thiophanate-methyl, zoxamide, pencycuron, fluopicolide, etc.

Benzanilide compounds: furametpyr, penthiopyrad, thifluzamide, boscalid, oxycarboxin, carboxyxin, fluopyram, flutolanil, mepronil ),etc.

Stravylline compounds: azoxystrobin, picoxystrobin, kresoximmethyl, trifloxystrobin, orysastrobin, metinominostrobin, pyraclostrobin ), Famoxadone, fenamidone, pyribencarb, dimoxystrobin, pyrametostrobin, pyraoxystrobin, etc.

Other compounds that inhibit electron transfer system: diflumetorim, cyazofamid, amisulbrom, meptyl dinocap, fluazinam, ferimzone, and the like.

Amino acid biosynthesis inhibitory active compounds: cyprodinil, mepanipyrim, pyrimethanil, blastcidin-S, streptomycin, kasugamycin, etc.

Sterol biosynthesis inhibiting active compounds: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole, Fluconazole, hexaconazole, imibenconazole, metoconazole, microbutanil, penconazole, propiconazole, simeconazole, teconazole , Triadimefon, triadimenol, triticonazole, imazalil, triflumizole, pefurazoate ), Prochloraz, fenarimol, fenhexamid, fenpropimorph, piperalin, spiroxamine, and the like.

Cell wall synthesis inhibitory active compounds: iprodione, myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil, etc.

Lipid biosynthesis inhibiting active compounds: iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb, dimethomorph, iprovalicarb, benchavalicarb, benthiavali carb Mandipropamid, etc.

Glucan biosynthesis inhibitory active compounds: validamycin, polyoxin B, etc.

Melanin biosynthesis inhibitory active compounds: pyroquion, tricyclazole, carpropamid, diclocymet, fenoxanil, etc.

Host resistance-inducing compounds: acibenzolar-S-methyl, probenazole, isothianil, laminarin, etc.

Other compounds with unclear effects: cymoxanil, fosetyl-Al, triazoxide, metasulfocarb, flusulfamide, chinomethionat, ethaboxam, cyflufenamide (Cyflufenamid), flutianil, metrafenone, tebufloquin, pyridylamidine, enestroburin, proquinazid, sequinane (SYN-524464), isopyrazam (SYN) -20 , Penflufen (BYF-14182), bixafen, fluxapyroxad, fluopyram, lumorph, variphenate (alifenalate), piri Phenone (pyriofenone), etc..

Examples of insecticides, acaricides and nematicides include acetylcholinesterase inhibitor compounds, GABA-dependent chloride channel inhibitor compounds, sodium ion channel inhibitor compounds, nicotinic acetylcholine receptor inhibitor compounds, chloride ion channel compound compounds Pseudo-juvenile hormone compounds, non-selective inhibitor compounds, selective feeding inhibitor compounds, mite growth inhibitor compounds, Bt agents, ATP synthesis inhibitor compounds, oxidative phosphorylation uncoupling compounds, nicotinic acetylcholine receptor channel inhibitor compounds, Chitin biosynthesis inhibiting compounds, molting / transformation disrupting compounds, octopamine antagonist compounds, electron transport system inhibiting compounds, voltage-gated sodium channel inhibiting compounds, lipid synthesis inhibiting compounds, ryanodine receptor inhibiting compounds, compounds having other or unclear effects, Etc. It can be.

Acetylcholinesterase inhibitors:
Aldicarb, benfuracarb, carbaryl, carbfuran, carbofuran, carbosulfan, fenobucarb, methiocarb, metomyl, oxamyl, thiodicarb ),etc.

Acephate, chlorpyrifos, diazinon, dimethoate, malathion, methamidophos, monocrotophos, parathion-methyl, profenofos Terbufos, imicyafos, etc.

GABA-dependent chloride channel inhibitor compounds: endosulfan, ethiprole, fipronil, acetoprole, etc.

Sodium ion channel blocking compounds: bifenthrin, cypermethrin, esfenvalerate, etofenprox, lambda-cyhalothrin, tefluthrin, DDT (DDT), Methoxychlor, etc.

Nicotinic acetylcholine receptor inhibitory compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam, thiamethoxam, etc.

Spinosyn, spinetoram, etc.

Chloride ion channel inhibiting compounds: abamectin, emamectin benzoate, milbemectin, lepimectin, etc.

Pseudo-juvenile hormone compounds: kinoprene, methoprene, phenoxycarb, pyriproxyfen, etc.

Non-selective inhibiting compounds: methyl bromide, chloropicrin, etc.

Selective feeding inhibitory compounds: pymetrozine, flonicamid, etc.

Tick growth inhibitory compounds: clofentezine, hexythiazox, etoxazole, etc.

Bt agent: Bacillus thuringiensis, etc.

ATP synthesis inhibiting compounds: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon, etc.

Oxidative phosphorylation uncoupling compound: chlorfenapyr, etc.

Nicotinic acetylcholine receptor channel inhibitory compounds: bensultap, cartap, thiocyclam, etc.

Chitin biosynthesis inhibiting compounds: Chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron, triflubenzuron (triflubenzuron) triflumuron), buprofezin, bistrifluron, etc.

Molting / transformation disrupting compounds: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, noviflumuron, etc.

Octopamine antagonist compounds: amitraz, hydramethylnon, acequinocyl, etc.

Electron transport system inhibitor compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone, etc.

Voltage-gated sodium channel inhibitor compounds: indoxacarb, metaflumizone, spirodiclofen, etc.

Lipid synthesis inhibiting compounds: spiromesifen, spirotetramat, etc.

Aluminum phosphate (Aluminium phosphide), etc.

Ryanodine receptor inhibitor compounds: chlorantranilprole, flubendiamide, cyantranilprol, etc.

Other or unclear compounds: azadirachtin, benzoximate, bifenazate, chinomethionat, dicofol, pyridalyl, pyrifluquinazon, fluene And sulfone.

Examples of herbicides include the following compounds.

Namely, benzobicyclon, bensulfuron-methyl, azimsulfuron, cinosulfuron, cyclosulfamuron, pyrazosulfuron-ethyl, imazosulfuron ), Indanofan, cyhalofop-butyl, tenylchlor, esprocarb, etobenzanid, cafenstrole, clomeprop, dimethametrynmu, dimethametrynmu, dimethametrynmu Bifenox, pyributicarb, pyriminobac-methyl, pretilachlor, bromobutide, benzofenap, topramezone, benthiocarb, Pentoxazone, benfuresate, mefenacet, fenoxaprop-P-ethyl, phenmedipham, diclofop-methyl, desmedifam ( desmedipham), etofumesate, isoproturon, amidosulfuron, anilofos, benfuresate, ethoxysulfuron, iodosulfuron, isoxadifen, isoxadifen Ramsulfuron, pyraclonil, mesosulfuron, diuron, neburon, dinoterb, carbetamide, bromoxynil, oxadiazon, dimeflon Diflufenican Aclonifen, benzofenap, oxaziclomefone, isoxaflutole, oxadiargyl, flurtamone, metribuzin, metabenzthiazron, methabenzthiazuron Tribufos, metamitron, methitron, ethiozin, flufenacet, sulcotrione, tefuryltrione, fentrazamide, propoxycarbazone, flucarbazone ), Metosulam, amicarbazone and the like.

Glyphosate-isopropylamine, glyphosate-trimesium, glufosinate, bialaphos, butamifos, prosulfocarb, ashram, linuron (linuron), calcium peroxide, alachlor, pendimethalin, acifluorfen-sodium, lactofen, ioxynil, alloxydim, cetoxydim (sethoxydim), napropamide, pyrazolate, pyraflufen-ethyl, imazapyr, sulfentrazone, paraquat, diquat, simazine , Atrazine, fluthiacet-methyl, Zarohoppu ethyl (quizalofop-ethyl), bentazone (bentazone), triaziflam (triaziflam), etc..

Thidiazuron, mefenpyr, ethephon, cyclanilide, flupoxam, penoxsulam, mesotrione, saflufenacil, beflutotosulfur (flucetosulfuron), flucetosulfuron (flucetosulfuron) ), Dimethenamid, propisochlor, metamifop, pyrasulfotole, pyrimisulfan, pyroxsulam, pyroxasulfone, fenoxasulfone Thiencarbazone, thiencarbazone-methyl, flufenpyr-ethyl, orthosulfamuron, indaziflam, propyrisulfuron on), glufosinate-P-sodium, ipfencarbazone, metazosulfuron, aminocyclopyrachlor, prosulfocarb, chlorimuron Examples of biological pesticides include the following compounds.
(1) Nuclear polyhedrosis virus (NPV), granular disease virus (GV), cytoplasmic polyhedrosis virus (CPV), etc.
(2) Steinernema carpocapsae, Steinernema glaseri, Monocrosporium phymatophagum, Steinernema kushidai, Steinernema kushidai ,etc.
(3) Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus, Talaromyces flavus, (Trichoderma atroviride), etc.
(4) Bacillus thuringiensis, Beauveria brongniartii, Beauveria bassiana, Paecilomyces fumosoroseus, Verticillium lecanii, nas Xest ,etc.
(5) Onsatsume wasp (Encarsia formosa), Sakutaku bee (Eretmocerus eremicus), Scarlet wasp (Eretmocerus mundus), Colleman's wasp (Aphidius colemani), Aphidoletes aphidimyzaly ), Dacnusa sibirica, Phytoseiulus persimilis, Amblyseius cucumeris, Amblyseius californicus, Orius strigicollis, etc.

Examples of pheromone agents include
Kodrelua ((E, E) -8,10-Dodecadien-1-ol), Beet Armirea B ((Z) -9-Tetradecen-1-ol), Tetradodecenyl acetate ((Z) -11 -Tetradecenyl acetate), pyrimalua (14-Methyl-1-octadecene), peach flua ((Z) -13-Eicosen-10-one), and the like.

Examples of natural fungicides and natural insecticides are:
Machine oils, Methylphenyl acetate, α-Pinene, Protein hydrolysate, (Z) -1-Tetradecen-1-ol, Turpentine , Etc.

Hereinafter, the present invention will be specifically described by way of examples. These do not limit the scope of the present invention.
Example 1 [Production Example]
(1) Synthesis step A of a compound in which R ¹ = 2-trifluoromethylphenyl, R ² = H, R ³ = benzyl in the general formula (I) (Table 1, compound No. 6) A: 4- (2-trifluoromethyl) phenyl-3-butyn-1-ol Isopropanol-water (1: 1) in 40 ml with 1.68 g 3-butyn-1-ol, 5.44 g 2-iodobenzotrifluoride, 236 mg palladium carbon Then, 15.2 g of sodium phosphate dodecahydrate was added, and the mixture was heated and stirred at 90 degrees for 3 hours. Thereafter, after cooling to room temperature, 100 ml of water and 100 ml of ethyl acetate were added to the reaction solution, followed by filtration. Further, 50 ml of ethyl acetate was added and the organic layer was separated, washed twice with 50 ml of saturated brine, and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 3.89 g of an alcohol form.
Step B: 4- (2-trifluoromethyl) phenyl-3-butynyl p-toluenesulfonate To 80 ml of toluene, add 17.4 g of the alcohol compound obtained in the above step, 7.12 ml of N-methylimidazole, and 12.4 ml of triethylamine. In a water bath, 17 g of a toluene solution of p-toluenesulfonyl chloride (80 ml) was added dropwise. The water bath was removed and the mixture was stirred at room temperature for 1 hour. After stirring, 250 ml of water and 150 ml of ethyl acetate were added to the reaction solution, and the organic layer was separated, washed with 75 ml of 1N hydrochloric acid and 75 ml of saturated brine, and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 29.7 g of tosyl.
Step C: N-4- (2-trifluoromethyl) phenyl-3-butynylbenzylamine To 10 ml of dimethyl sulfoxide was added 695 mg of the tosyl compound obtained in the above step, 281 mg of sodium iodide, 484 mg of benzylamine, and 110 ° C. Stir for 3 hours. After cooling to room temperature, 60 ml of water was added to the reaction solution, and extracted twice with 100 ml of ethyl acetate. The organic layer was washed 3 times with 60 ml of saturated brine and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 210 mg of a benzylamine compound.
Step D: 4- (1-methyl-4- {2-trifluoromethyl} phenyl-3-butynylamino) -N-benzylquinazoline 210 mg of the benzylamine compound obtained in the above step, 5 ml of N, N-dimethylformamide, triethylamine 130 μl of 4-chloroquinazoline was added and stirred for 7 hours at 100 degrees. After cooling the reaction solution to room temperature, 50 ml of water was added to the reaction solution and extracted twice with 80 ml of ethyl acetate. The organic layer was washed twice with 50 ml of saturated brine and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 205 mg of a benzylamine compound.

According to a similar production method, Table 1, Compound No. 7 was synthesized.
(2) Synthesis step A of a compound in which R ¹ = 2-trifluoromethylphenyl, R ² = H, R ³ = methyl in the general formula (I) (Table 1, compound No. 1) A: 4- ( 2-trifluoromethyl) phenyl-3-butynyl methanesulfonate To 110 ml of dichloromethane was added 12.0 g of the alcohol compound obtained in the above (1) Step A and 9.34 ml of triethylamine, and 4.8 ml of methanesulfonyl chloride was added in an ice bath. It was dripped. The ice bath was removed and the mixture was stirred at room temperature for 1 hour. After stirring, 250 ml of water was added to the reaction solution, and the organic layer was separated, washed with 80 ml of 1N hydrochloric acid and 80 ml of saturated brine, and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 15.0 g of mesyl.
Step B: N-4- (2-trifluoromethyl) phenyl-3-butynyl-N-methylamine To 1 g of the methylamine compound obtained in the above step, 17 ml of methanol and 5 ml of a 40% methylamine methanol solution were added. The mixture was heated and stirred at 50 degrees. The reaction mixture was concentrated, and the residue was purified by flash chromatography (biotage AB / Isolera ^™ ) to obtain 370 mg of a methylamine compound.
Step C: 4- (1-methyl-4- {2-trifluoromethyl} phenyl-3-butynylamino) -N-methylquinazoline 370 mg of the methylamine compound obtained in the above step was added to 10 ml of N, N-dimethylformamide and triethylamine. 225 mg and 4-chloroquinazoline 244 mg were added, and the mixture was stirred at 80 ° C. for 3 hours. After cooling the reaction solution to room temperature, 50 ml of water was added to the reaction solution and extracted twice with 80 ml of ethyl acetate. The organic layer was washed twice with 50 ml of saturated brine and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 417 mg of a benzylamine compound.

According to a similar production method, Table 1, Compound No. 2 to 5, 8, and 9 were synthesized.
(3) Synthesis step A of the compound in which R ¹ = 2-trifluoromethylphenyl, R ² = H, R ³ = acetyl in the general formula (I) (Table 1, compound No. 10) A: 2-tri To a test tube with a fluoromethylphenyl-3-butynylamine screw cap, 1.4 g of the tosyl compound obtained in the above step (1), 10 ml of dioxane and 9 ml of 28% aqueous ammonia were added and stirred with heating at 50 degrees for 8 hours. After cooling the reaction solution, 50 ml of water was added, extracted twice with 70 ml of ethyl acetate, and dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 700 mg of an amine compound.
Step B: 4- (1-methyl-4- {2-trifluoromethyl} phenyl-3-butynylamino) quinazoline 210 mg of the amine compound obtained in the above step, 5 ml of N, N-dimethylformamide, 130 μl of triethylamine, 4-chloro Quinazoline was added and the mixture was heated and stirred at 80 ° C. for 3 hours. After cooling to room temperature, 50 ml of water was added to the reaction solution, and extracted twice with 80 ml of ethyl acetate. The organic layer was washed twice with 50 ml of saturated brine and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 205 mg of a benzylamine compound.
Step C: 4- (1-methyl-4- {2-trifluoromethyl} phenyl-3-butynylamino) -N-acetylquinazoline 5 ml of acetic anhydride was added to 200 mg of the quinazoline compound obtained in the above step, and 9 Stir for hours. After cooling to room temperature, 50 ml of ethyl acetate was added, and the organic layer was washed twice with 30 ml of water and once with 30 ml of saturated aqueous sodium hydrogen carbonate, and then dried over sodium sulfate. After filtering sodium sulfate, the organic layer was concentrated, and the residue was purified by flash automatic generator flash chromatography (Biotage AB / Isolera ^™ ) to obtain 70 mg of an acetyl compound.

The compounds [I] synthesized as described above and their physical properties are shown in Table 1 (Table 1-1 to Table 1-2). In addition, Table 2 shows the NMR data of the compound [I]. In this specification, “Table 1” is a generic name (generic name) of Tables 1-1 to 1-2.

When the pest control composition of the present invention is used, it is formulated into powders, granules, fine granules, tablets, solutions, emulsions, wettable powders, flowables, aerosols and the like that are widely used in agricultural chemical formulations. These can be used in a normal application method such as seed treatment, foliage spraying, soil application or water surface application.

The application rate of the pest control composition according to the present invention varies depending on the target disease, the occurrence tendency of pests, the degree of damage, environmental conditions, the formulation type to be used, etc., but the general application rate is 0.1 g per 10 ares. ~ 1kg. When diluting liquids, emulsions, wettable powders, flowables, etc. with water, use them at a dilution concentration in the range of 1 to 10,000 ppm.

Moreover, the pest control composition according to the present invention is sterilized with fungicides, fungicides, bactericides, acaricides, nematicides, insecticides, biopesticides, herbicides, plant hormones, plant growth regulators, synergists. , Pesticides, repellents, pigments, fertilizers, etc., or a combination of one or more selected from those active ingredients in combination with a pest control compound Fluctuates depending on the type of disease, target disease, incidence, degree of damage, environmental conditions, formulation type used As specific examples of the compound group represented by the general formula I, one or more of the quinazoline derivatives which are the compound groups described in [Table 1-1] and [Table 1-2] and one or more of the existing ones listed above The weight mixing ratio of the sterilizing and / or insecticidal compound for use is in the ratio of 1: 0.1 to 1: 100000, and the typical application rate is 0.1 g to 1 kg per 10 ares. When liquids, emulsions, wettable powders, flowables and the like are diluted with water, they are used at a dilution concentration ranging from 1 to 10,000 ppm.

When the compound used in the present invention is used as an agricultural and horticultural pest control composition, the active ingredient can be used in an appropriate dosage form depending on the purpose. Usually, the active ingredient is diluted with an inert liquid or solid carrier, and if necessary, a surfactant or the like is added thereto, and it can be used in the form of a powder, wettable powder, emulsion, granule or the like.

Examples of suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea, and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. It is done. Examples of the surfactant and dispersant include dinaphthyl methane sulfonate, alcohol sulfate ester salt, alkyl aryl sulfonate, lignin sulfonate, polyoxyethylene glycol ether, polyoxyethylene alkyl aryl ether, and polyoxyethylene sorbitan. Examples include monoalkylates. Examples of the auxiliary agent include carboxymethyl cellulose. These preparations are sprayed diluted to an appropriate concentration or applied directly.

Furthermore, the pest control composition of the present invention may be used in combination with insecticides, other fungicides, herbicides, plant growth regulators, fertilizers and the like as necessary.

Next, the formulation method will be specifically described with reference to typical examples of the agricultural and horticultural pest control composition of the present invention. In the following description, “%” indicates a weight percentage.
Example 2 [Formulation example]
Formulation Example 1: Emulsion 10 parts of the compound of the present invention were dissolved in 45 parts of 1,2-dimethyl-4-ethylbenzene and 35 parts of 1-methyl-2-pyrrolidinone, and this was dissolved in Solpol 3005X (an interface manufactured by Toho Chemical Industry Co., Ltd.). 10 parts of an activator (trade name) was added and mixed by stirring to obtain a 10% emulsion.
Formulation example 2: wettable powder 10 parts of the compound of the present invention was added to 2 parts of sodium lauryl sulfate, 4 parts of sodium lignin sulfonate, 20 parts of white carbon and 64 parts of clay, and mixed by stirring with a juice mixer. % Wettable powder was obtained.
Formulation Example 3: Granules To 5 parts of the compound of the present invention, 2 parts of sodium dodecylbenzenesulfonate, 2 parts of carboxymethylcellulose, 2 parts of sodium lauryl sulfate, 10 parts of bentonite and 79 parts of clay were added and mixed thoroughly. An appropriate amount of water was added and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 5% granule.
Formulation Example 4: Powder 1 part of the present compound is dissolved in 2 parts of soybean oil, 5 parts of white carbon, 0.3 part of isopropyl phosphate (PAP) and 91.7 parts of clay are added, and the mixture is stirred and mixed with a juice mixer. A 1% powder was obtained.
Formulation Example 5: Flowable agent 20 parts of water containing 20 parts of the present compound and 2 parts, 1 part and 0.2 parts of polyoxyethylene alkyl ether, sodium dialkylsulfosuccinate and 1,2-benzisothiazolin-3-one, respectively Were mixed with 60 parts of water containing 8 parts and 0.32 parts of propylene glycol and xanthan gum, respectively, to obtain a 20% suspension in water.
Formulation Example 6: Granule wettable powder To 20 parts of the present compound, 2 parts of sodium lauryl sulfate, 3 parts of sodium alkylnaphthalene sulfonate, 5 parts of dextrin, 20 parts of white carbon and 50 parts of clay were added and mixed thoroughly. An appropriate amount of water was added, and the mixture was further stirred, granulated with a granulator, and dried by ventilation to obtain a 20% granular wettable powder.
Example 3 [Efficacy test]
Next, the effect of the agricultural and horticultural pest control composition of the present invention will be specifically described with reference to test examples.
Test Example 1 Control effect against tomato plague Compound group (4- (3-butynyl) aminoquinazoline shown in [Table 1-1] and [Table 1-2] in pot-planted tomato seedlings (variety: sugar lamp, 4.5 leaf stage) Derivatives), and a chemical solution (hereinafter referred to as a reagent solution) in which 10% wettable powder of compound β is adjusted to 50 ppm is sprayed at 15 ml per pot using a spray gun. One day later, zoospores of Phytophthora infestans After inoculating the suspension (spore concentration 1.0 × 10 ⁴ cells / ml) by spraying, placing it in a humid room condition at 21 ° C. for 1 day and further placing it in a greenhouse for 3 days to cause sufficient disease, each leaf The disease area ratio was investigated, and the control value was calculated using the following formula.
Formula of control value: control value = {(untreated disease area rate−treated drug disease rate) / untreated disease area rate} × 100
The calculated control value was determined according to the following criteria.
A: 100% ≧ control value ≧ 98%
B: 98%> control value ≧ 60%
C: 60%> control value ≧ 20%
D: 20%> control value ≧ 0%

Test Example 2 Control effect against cucumber downy mildew Potato cucumber seedlings (variety: Sagamihanjiro, 2.5 leaf stage) Compound group 4- (3-butynyl) amino shown in [Table 1-1] and [Table 1-2] Spray a quinazoline derivative and a chemical solution (hereinafter referred to as a reagent solution) with a 10% wettable powder of compound β to 50 ppm using a spray gun, and spray 15 ml per pot. Nylon suspension (conidia concentration 1.0 × 10 ⁴ cells / ml) was spray-inoculated. After inoculation, the sample was placed in a humid chamber condition at 21 ° C. for 1 day and further placed in a greenhouse for 3 days to cause sufficient disease, and then the diseased area of each leaf was compared with the untreated group. In the same manner as above, the control effect was determined.

Test Example 3 Control effect against cucumber powdery mildew Potato cucumber seedlings (variety: Sagamihanjiro, 2-leaf stage) Compound group 4- (3-butynyl) aminoquinazoline derivatives shown in [Table 1-1] and [Table 1-2] , And a chemical solution (hereinafter referred to as a reagent solution) prepared by adjusting 10% wettable powder of compound β to 50 ppm, sprayed 15 ml per pot using a spray gun. A turbid liquid (conidia concentration of 1.0 × 10 ⁵ cells / ml) was spray-inoculated. After sufficient disease was established in a greenhouse for 14 days, the degree of disease on each leaf was compared with the untreated group, and the control effect was determined in the same manner as in Test Example 1.

Test Example 4 Insecticidal effect on cotton aphids The compound group shown in [Table 1-1] and [Table 1-2] (4- (3-butynyl) aminoquinazoline derivative), and 10% wettable powder of compound β, the compound is 50 ppm Diluted to Cucumber leaf pieces having a diameter of 3 cm were placed in a plastic cup filled with 0.5% soft agar, and 5 female Aphis gossypi females were released. After standing overnight, the number of larvae larvae was counted, and 0.4 ml of the adjusted medicinal solution was sprayed, and the number of dead insects after 2 days was counted to calculate the mortality. The calculated death rate was applied to the following criteria to determine the insecticidal effect.
A: 100% ≧ mortality ≧ 98%
B: 98%>mortality> 60%
C: 60%> mortality ≧ 20%
D: 20%> death rate ≧ 0%

Test Example 5 Effect of killing insects against female adult spider mite The compound group shown in [Table 1-1] and [Table 1-2] (4- (3-butynyl) aminoquinazoline derivative) and the compound β with 10% wettable powder of the compound Was diluted to 100 ppm. A 3 cm diameter kidney bean leaf was placed on a plastic cup filled with 0.5% soft agar, and 10 female adults of Tetanychus urticae were released. The adjusted chemical solution was sprayed at 0.4 ml each, and the number of dead insects after 2 days was counted to calculate the mortality rate. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate.

Test Example 6. Ovicidal effect on spider mite eggs The compound group shown in [Table 1-1] and [Table 1-2] (4- (3-butynyl) aminoquinazoline derivative) and 10% wettable powder of compound β Dilute to 100 ppm. A 3 cm diameter kidney bean leaf was placed on a plastic cup filled with 0.5% soft agar, and 10 female adults of Tetanychus urticae were released. After removing the female larvae that were allowed to stand overnight at room temperature for egg laying and releasing, 0.4 ml each of the prepared medicinal solution was sprayed, and the number of dead insects after 6 days was counted to calculate the mortality. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate.

Test Example 7-1. Insecticidal effect against Spodoptera litura: Compound group (4- (3-butynyl) aminoquinazoline derivative) shown in [Table 1-1] and [Table 1-2], and 10% wettable powder of compound β make the compound 100 ppm Diluted to 3 cm diameter Chinese cabbage leaf pieces were dipped in each chemical solution, then air-dried, housed in a plastic petri dish, and 10 third-instar larvae of Spodoptera litra were released. The mortality was calculated by counting the number of dead insects 2 days after treatment. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate.

Test Example 7-2. Insecticidal effect against Thrips thrips

Compound group (4- (3-butynyl) shown in [Table 1-1] and [Table 1-2]
Aminoquinazoline derivative) and a 10% wettable powder of compound β were diluted so that the compound was 500 ppm. The kidney leaf pieces having a diameter of 33 mm were immersed in each chemical solution and air-dried, and then housed in a petri dish having a diameter of 50 mm with filter paper and 10 larvae (Franklinella occidentalis) 1 and 10 instar larvae were released. The number of living and dead individuals 3 days after the treatment was measured, and the mortality rate was calculated. Determination was made according to the same criteria as in Test Example 4 from the calculated mortality rate.

Test Example 8. Control effect against cucumber powdery mildew Seed in [Table 1-1] and [Table 1-2] prepared according to formulation example in pot-planted cucumber seedlings (variety: Sagamihanjiro, 2-leaf stage) The compound group (4- (3-butynyl) aminoquinazoline derivative) and the existing bactericidal active compounds shown in [Table 10] (hereinafter referred to as the corresponding alphabet) are diluted with water so as to become active ingredients of a predetermined concentration The resulting mixture was sprayed at 15 ml per pot using a spray gun. After air drying, a conidial suspension of cucumber powdery mildew (Sphaerotheca fuliginea) was spray-inoculated. Then, after cultivation in a greenhouse for 14 days, the diseased area ratio of each leaf was investigated, and the control value was calculated according to the calculation formula of Test Example 1.
Formula of control value: control value = {(untreated disease area rate−treated drug disease rate) / untreated disease area rate} × 100
Moreover, the effect expected by the combination of each active compound was calculated | required with the calculation formula of Colby (Colby). When the experimental value is larger than the calculated value E, the effect of the combination shows a synergistic effect.

Colby's formula (Colby, SR, “Calculating synergistic and antagonistic responses of herbicide combinations”, Weeds 15, 20-22 (1967)) Is shown below.
Colby's formula: E = A + B-(A x B / 100)
E Expected effect on control of untreated when a mixture of active compound X at concentration x and active compound Y at concentration y is used (control value)
A Effect (control value) on untreated control when active compound X at concentration x is used
B Effect of the active compound Y with a concentration y on the untreated control (control value)
Table 10 shows the effects of the individual active compounds, and Tables 11-1 to 11-7 show the effects of the mixture of the compound of the present invention and the existing bactericidal active compounds.

In Table 10 and Tables 11-1 to 11-7 below, the test compounds represented by the two-letter alphabets mean the following compounds.

Aa: chlorothalonil Nb: quinomethionate Ab: iminotazine albecyl acid Hd: triflumizole Hb: tebuconazole Ha: diphenoconazole Hc: triazimephone He: fenpropimorph Ea: azoxystrobin Ed: pyraclostrobin Ec: trifloxystrobin Eb: Cresoxime methyl Nc: cyflufenamide Da: penthiopyrad Nd: fluthianyl Ia: quinoxyphene Ca: thiophanate methyl Fa: diflumetrim Ma: acibenzoral S. methyl

As is apparent from Tables 11-1 to 11-7 above, the mixture of the compound of the present invention and the existing bactericidal active compound has an experimental value larger than the calculated value E, and the effect of the combination shows a synergistic effect. It was supported.
Test Example 9. Control effect against cucumber downy mildew [Table 1-1] and [Table 1-2] prepared according to formulation examples in pot-planted cucumber seedlings (variety: Sagami Hanjiro, 2.5 leaf stage) A compound group 4- (3-butynyl) aminoquinazoline derivative shown in FIG. 5 and an existing bactericidal active compound shown in [Table 12] (hereinafter, indicated by the corresponding alphabet) are diluted with water so as to become an active ingredient having a predetermined concentration. The resulting mixture was sprayed at 15 ml per pot using a spray gun. After air drying, a conidial suspension of cucumber downy mildew (Pseudoperonospora cubensis) was spray-inoculated and immediately maintained at 21 ° C. and 100% humidity for 1 day. Further, after 3 days at room temperature, the disease area ratio of each leaf was examined, and the control value was calculated in the same manner as in Test Example 8. Moreover, the effect expected by the combination of the individual active compounds was determined by the Colby formula. Table 12 shows the effects of the individual active compounds, and Tables 13-1 to 13-4 show the effects of the mixture of the compound of the present invention and the existing bactericidal active compounds.

In Table 12 and Tables 13-1 to 13-4 below, the test compounds represented by two-letter alphabets mean the following compounds.

Aa: Chlorothalonyl Ac: Manzeb Fb: Ciazofamide Fc: Amisulbrom Na: Simoxanyl Eb: Cresoxylmethyl Ea: Azoxystrobin Ba: Metalaxyl M
Jc: Mandipropamide Jb: Bench avalicarb isopropyl Ja: Dimethomorph

As apparent from Tables 13-1 to 13-4 above, the mixture of the compound of the present invention and the existing bactericidal active compound has an experimental value larger than the calculated value E, and the effect of the combination shows a synergistic effect. Was supported.
Test Example 10 Insecticidal effect on cotton aphids Compound groups shown in [Table 1-1] and [Table 1-2] (4- (3-butynyl) aminoquinazoline derivatives) and existing insecticidal active compounds shown in [Table 14] (Indicated by the corresponding alphabet) was diluted with water to give an active ingredient at a predetermined concentration to prepare a mixture. Cucumber leaf pieces having a diameter of 3 cm were placed in a plastic cup filled with 0.5% soft agar, and 5 female Aphis gossypi females were released. After standing overnight, the number of larvae was counted, and 0.4 ml of the prepared medicinal solution was sprayed to count the number of dead worms two days later. The death rate was calculated according to Moreover, the effect expected by the combination of the individual active compounds was determined by the Colby formula. Table 14 shows the effects of the individual active compounds, and Tables 15-1 to 15-2 show the effects of the mixture of the compound of the present invention and the existing insecticidal active compounds.

As is apparent from Tables 15-1 to 15-2 above, the mixture of the compound of the present invention and the existing insecticidal active compound has an experimental value larger than the calculated value E, and the combination effect shows a synergistic effect. It was supported.

The agricultural and horticultural pest control composition comprising one or more quinazoline derivatives of the present invention as an active ingredient is particularly low in the amount of pests such as pathogenic bacteria, insects and mites that affect agricultural and horticultural plants. It exhibits excellent control effects and is extremely useful as a new agrochemical because it is extremely safe for useful crops. In addition, the mixture of the quinazoline derivative of the present invention and the existing bactericidal active compound, and the mixture of the quinazoline derivative of the present invention and the existing insecticidal active compound both have an experimental value larger than the calculated value E based on Colby's formula. Since the effect of the combination is confirmed to have a synergistic effect, it is extremely useful as a mixture.

Claims (9)

1. Formula [I]:
   

   

   [Wherein n represents an integer of 0 to 4,
   R ¹ is a) phenyl, benzyl, oxazolyl, isoxazolyl, furyl, benzofuryl, isobenzofuryl, dihydrobenzofuryl, thiazolyl, isothiazolyl, naphthyl, pyrimidinyl, pyrazinyl, quinoxalyl, quinazolinyl, pyridyl, quinolyl, isoquinolyl, benzothiazolyl, benzoisothiazo Optionally 0 to 3 heteroatoms selected from the group consisting of ril, pyrrolyl, indolyl, isoindolyl, benzoxazolyl, benzisoxazolyl, thienyl, benzothienyl, imidazolyl, benzimidazolyl, pyrazolyl, pyridonyl Is a monocyclic or bicyclic ring containing,
   b) linear or branched alkyl having 1 to 6 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, Cycloalkyl having 3 to 8 carbon atoms or cycloalkenyl having 3 to 8 carbon atoms,
   c) —SiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷ are linear or branched alkyl having 1 to 6 carbon atoms, and 1 to 3 carbon atoms substituted by one halogen atom) Linear or branched haloalkyl, linear or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl substituted by one cyano group, all having the same substituent, but all different substituents May be)
   d) selected from hydrogen atoms and in the case of a) or b) R ¹ is —C (O) OR, —C (O) R, —R, —OR, —SR, —SO ₂ R, —OC ( O) R, —C (O) NHR, —C (O) NR ₂ , —NHSO ₂ R, —NRSO ₂ R, —NHR, —NR ₂ , —NHC (O) R, —NRC (O) R, —NHC (O) OR, —NRC (O) OR, —N (OR) C (O) OR, —NHSO ₂ R, —NRSO ₂ R, —SO ₂ NHR, —SO ₂ NR ₂ (where R Is linear or branched alkyl having 1 to 8 carbon atoms, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or A cycloalkyl having 3 to 8 carbon atoms), —SiR ⁵ R ⁶ R ⁷ , —OSiR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ , R ⁷ is a linear or branched alkyl having 1 to 6 carbon atoms, a linear or branched haloalkyl having 1 to 3 carbon atoms substituted by one halogen atom, or one cyano group Substituted or straight-chain or branched cyanoalkyl having 1 to 3 carbon atoms and phenyl, two or all of which may be the same or different, and haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms, haloalkenyl (the same or different, and the number of carbon atoms substituted with 1 to 4 halogen atoms) Linear or branched alkenyl group having 2 to 6 carbon atoms, haloalkoxy (same or different, linear or branched alkoxy group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) ), A straight chain having 1 to 3 carbon atoms substituted by 1 or 2 acyl groups represented by acylalkoxy ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) -CO-) 1 or 2 acyloxy groups represented by a chain or branched alkoxy group), acyloxyalkyl ((linear or branched aliphatic hydrocarbon group having 1 to 8 carbon atoms) —CO—O—) Substituted by a linear or branched alkyl group having 1 to 3 carbon atoms and alkylsulfonylalkyl substituted by 1 or 2 alkylsulfonyl groups having 1 to 8 carbon atoms Straight chain or branched alkyl group having 1 to 3 carbon atoms), siloxyalkyl (—OSiR ⁵ R ⁶ R ^{7, where} R ⁵ , R ⁶ , and R ⁷ are linear chains having 1 to 6 carbon atoms) Or branched alkyl, halogen atom 1 A straight-chain or branched haloalkyl having 1 to 3 carbon atoms substituted by 1 or a straight-chain or branched cyanoalkyl having 1 to 3 carbon atoms substituted by one cyano group or phenyl A linear or branched alkyl group having 1 to 3 carbon atoms substituted by two or all of which may be the same substituent or all different substituents), hydroxyalkyl (one or two hydroxyl groups) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1), alkoxyalkyl (substituted by 1 or 2 linear or branched alkoxy groups having 1 to 8 carbon atoms) Linear or branched alkyl group having 1 to 3 carbon atoms), haloalkoxyalkyl (same or different, linear or branched carbon group having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Is a linear or branched alkyl group having 1 to 3 carbon atoms substituted by a branched 1 or 2 haloalkoxy group, alkylthioalkyl (linear or branched having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkylthio groups, or a dialkoxyacetal (a linear or branched alkoxy group having 1 to 8 carbon atoms) Is a dialkoxymethyl group in which two methyl groups are substituted), alkoxyalkoxy (a straight chain having 1 to 3 carbon atoms substituted by 1 or 2 straight or branched alkoxy groups having 1 to 8 carbon atoms). A linear or branched alkyl group having 1 to 3 carbon atoms substituted by one or two cyano groups), halogen, cyano, nitro, amino Hydroxy, pentahalosulfanyl, benzyl, benzyloxy, phenyl, phenoxy, pyridyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, thienyl, benzothiazolyl, benzoxazolyl, benzodioxolyl, imide, formyl (-CHO), carboxyl Optionally substituted with (—COOH), formamide (—NHCHO), cyclic ether, and cyclic amine,
   R ² is a hydrogen atom, —R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a linear or branched group having 1 to 8 carbon atoms) Alkyl, linear or branched alkenyl having 2 to 8 carbon atoms, linear or branched alkynyl having 2 to 8 carbon atoms, or cycloalkyl having 3 to 8 carbon atoms), hydroxyalkyl ( A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), an alkoxyalkyl (a linear or branched 1 or 2 carbon atom having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by an alkoxy group of the above, and a haloalkoxyalkyl (identical or different, and having 1 to 9 carbon atoms substituted with 1 to 9 halogen atoms) 4 linear or branched 1 or A linear or branched alkyl group having 1 to 3 carbon atoms substituted by one haloalkoxy group), phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, and having 1 to 9 halogen atoms) Substituted or straight chain or branched alkyl group having 1 to 4 carbon atoms), haloalkoxy (same or different, straight chain having 1 to 4 carbon atoms substituted with 1 to 9 halogen atoms) Represents a branched or branched alkoxy group),
   R ³ is —R, —C (O) R, —OR, —C (O) OR, —C (O) NHR, —CONR ₂ (where R is a straight chain having 1 to 8 carbon atoms) Or a branched alkyl, a linear or branched alkenyl having 2 to 8 carbon atoms, a linear or branched alkynyl having 2 to 8 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms) Hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl (a linear or branched group having 1 to 8 carbon atoms) A linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkoxy groups), a haloalkoxyalkyl (identical or different, carbons substituted with 1 to 9 halogen atoms) 1 to 4 straight or branched 1 atom Is a linear or branched alkyl group having 1 to 3 carbon atoms substituted by two haloalkoxy groups), benzyl, phenethyl, phenyl, heteroaryl, halogen, cyano, haloalkyl (identical or different, halogen Straight or branched alkyl group having 1 to 4 carbon atoms substituted with 1 to 9 atoms or haloalkoxy (same or different, substituted with 1 to 9 halogen atoms) A linear or branched 1 or 2 alkoxy group having 1 to 4 carbon atoms),
   (R ⁴⁾ R ⁴ in the _n is a hydrogen atom, a methyl group, a fluorine atom, a chlorine atom, a bromine atom, an iodine atom, a methoxy group, a trifluoromethyl group, a cyano group, a nitro group, a methylthio group, a propargyl group, propargyl Represents an oxy group, a benzyl group, a benzyloxy group, a heteroaryl group or a phenyl group, and when n is 2 to 4, each R ⁴ may be the same or different. ]
   A quinazoline derivative represented by
2. R ² is a hydrogen atom, a halogen atom, a cyano group, phenyl, heteroaryl, —R, —C (O) OR, —C (O) NHR (where R is a straight chain having 1 to 8 carbon atoms) Or a branched alkyl, a linear or branched alkenyl having 2 to 8 carbon atoms, a linear or branched alkynyl having 2 to 8 carbon atoms, or a cycloalkyl having 3 to 8 carbon atoms) Hydroxyalkyl (a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 hydroxyl groups), alkoxyalkyl (a linear or branched group having 1 to 8 carbon atoms) The quinazoline derivative according to claim 1, which is a linear or branched alkyl group having 1 to 3 carbon atoms substituted by 1 or 2 alkoxy groups.
3. R ¹ is optionally selected from the group consisting of phenyl, oxazolyl, furyl, thiazolyl, naphthyl, pyrimidinyl, pyridyl, benzothiazolyl, pyrrolyl, benzoxazolyl, pyrazinyl, thienyl, imidazolyl, optionally with 0 to 3 heteroatoms The quinazoline derivative according to claim 1, wherein the quinazoline derivative is selected from monocyclic or bicyclic rings.
4. Formula [II]:
   

   

   [Wherein (R ⁴ ) _n has the meaning described in claim 1. ]
   A 4-chloroquinazoline derivative [II] represented by
   Formula [III]:
   

   

   [Wherein R ¹ , R ² and R ³ have the meanings described in claim 1. ]
   The method for producing a quinazoline derivative represented by the formula [I] according to claim 1, wherein the 3-butynylamine derivative [III] represented by formula (I) is reacted in the presence of a base.
5. A pest control agent comprising one or more quinazoline derivatives represented by the formula [I] according to claim 1 as an active ingredient.
6. One or more quinazoline derivatives represented by the formula [I] according to claim 1 as active ingredients, and one or more of the bactericidal and insecticidal compounds shown in the following (1) to (39) And a pest control composition for agricultural and horticultural use, comprising:
   (1) SH synthesis inhibitory active compounds: chlorothalonil, dithianon, captan, folpet, iminoctadine-albesilate, iminoctadine-triacetate, Ferbam, nabam, maneb, mancozeb, metiram, propineb, polycarbamate, thiram, ziram, zineb , Cupric oxide, Copper hydroxide, Copper oxychloride, Copper sulfate (anhydride), Copper sulfate, Sulfur );
   (2) Nucleic acid biosynthesis inhibiting active compounds: metalaxyl, metalaxyl-M, oxadixyl, bupirimate, hymexazol, oxolinic acid;
   (3) Spindle yarn formation inhibitory active compound: benomyl, carbendazim, dietofencarb, thiophanate-methyl, zoxamide, penencycuron, fluopicolide;
   (4) Benzanilide compounds: furametpyr, penthiopyrad, thifluzamide, boscalid, oxycarboxin, carboxyxin, fluopyram, flutolanil, Mepronil;
   (5) strobilurin compounds: azoxystrobin, picoxystrobin, kresoximmethyl, trifloxystrobin, orysastrobin, metinominostrobin, pyraclosto Robin (pyraclostrobin), famoxadone (fenamidone), pyribencarb (pyribencarb), dimoxystrobin, pyrametostrobin, pyraoxystrobin (pyraoxystrobin);
   (6) Other compounds that inhibit electron transport system: diflumetorim, cyazofamid, amisulbrom), meptyl dinocap, fluazinam, ferimzone;
   (7) Amino acid biosynthesis inhibiting active compounds: cyprodinil, mepanipyrim, pyrimemethanil, blastcidin-S, streptomycin, kasugamycin;
   (8) Sterol biosynthesis inhibiting active compounds: azaconazole, bitertanol, bromuconazole, cyproconazole, difenoconazole, epoxiconazole, fenbuconazole fenbuconazole), fluconazole, furaconazole, hexaconazole, imibenconazole, metoconazole, microbutanil, penconazole, propiconazole, simeconazole, simeconazole, simeconazole (Tebuconazole), triadimefon, triadimenol, triticonazole, imazalil, triflumizole, pefazoate (pefur) azoate), prochloraz, fenarimol, fenhexamid, fenpropimorph, piperalin, spiroxamine;
   (9) Cell wall synthesis inhibitory active compounds: iprodione, myclozolin, procymidone, vinclozolin, quinoxyfen, fludioxonil;
   (10) Lipid biosynthesis inhibiting active compounds: iprobenfos, isoprothiolane, quintozene, propamocarb, prothicarb, dimethomorph, iprovalicarb, (Jb) bencher Berithiavalicarb, mandipropamid;
   (11) Glucan biosynthesis inhibitory active compounds: balidamycin, polyoxin B;
   (12) Melanin biosynthesis inhibiting active compound: pyroquion, tricyclazole, carpropamid, diclocymet, fenoxanil;
   (13) Host resistance-inducing compound: acibenzolar-S-methyl, probenazole, isotianil, laminarin;
   (14) Other or unclear compounds: cymoxanil, fosetyl-Al, triazoxide, metasulfocarb, flusulfamide, chinomethionat, ethaboxam ( ethaboxam), cyflufenamid, flutianil, metrafenone, tebufloquin, pyridylamidine, enestroburin, proquinazid, sequinane (SYN-5244) SYN-520), penflufen (BYF-14182), bixafen, fluxapyroxad, fluopyram, flumorph, varifenalate (Valifenalat) e);
   (15) Biofungicide: Agrobacterium radiobacter, Bacillus subtilis, Erwinia carotovora, Pseudomonas fluorescens, Talaromyces flavus , Trichoderma atroviride;
   (16) Acetylcholinesterase inhibitors: aldicarb, benfuracarb, carbaryl, carbfuran, carbofuran, carbosulfan, fenobucarb, methiocarb, methomyl, Oxamyl, thiodicarb;
   (17) Acephate, chlorpyrifos, diazinon, dimethoate, malathion, methamidophos, monocrotophos, parathion-methyl, profenofos (Profenofos), terbufos, imicyafos;
   (18) GABA-dependent chloride channel inhibitor compounds: endosulfan, ethiprole, fipronil, acetoprole;
   (19) Sodium ion channel inhibiting compounds: bifenthrin, cypermethrin, esfenvalerate, etofenprox, lambda-cyhalothrin, tefluthrin, DDT ( DDT), methoxychlor;
   (20) Nicotinic acetylcholine receptor inhibitory compounds: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam; thiamethoxam;
   (21) spinosyn, spinetoram;
   (22) Chloride ion channel inhibiting compounds: abamectin, emamectin benzoate, milbemectin, lepimectin;
   (23) pseudo juvenile hormone compounds: kinoprene, metoprene, phenoxycarb, pyriproxyfen;
   (24) Non-selective inhibitory compounds: methyl bromide, chloropicrin;
   (25) Selective feeding inhibitory compounds: pymetrozine, flonicamid;
   (26) Tick growth inhibitory compounds: clofentezine, hexythiazox, etoxazole;
   (27) Bt agent: Bacillus thuringiensis;
   (28) ATP synthesis inhibiting compounds: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifon;
   (29) Oxidative phosphorylation uncoupling compound: chlorfenapyr;
   (30) Nicotinic acetylcholine receptor channel inhibitory compounds: bensultap, cartap, thiocyclam;
   (31) Chitin biosynthesis inhibiting compounds: chlorfluazuron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron , Triflumuron, buprofezin, bistrifluron;
   (32) molting / metamorphosis disrupting compounds: cyromazine, chromafenozide, halofenozide, methoxyfenozide, tebufenozide, noviflumuron;
   (33) Octopamine antagonist compound: amitraz, hydramethylnon, acequinocyl;
   (34) Electron transport system inhibitor compounds: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone;
   (35) Aluminum phosphide;
   (36) Voltage-gated sodium channel inhibitor compounds: indoxacarb, metaflumizone, spirodiclofen;
   (37) Lipid synthesis inhibiting compounds: spiromesifen, spirotetramat;
   (38) Ryanodine receptor inhibitor compounds: chlorantranilprole, flubendiamide, cyantranilprol; and (39) Other or unclear compounds: azadirachtin, Benzximate, bifenazate, chinomethionat, dicohol, pyridalyl, pyrifluquinazon, fluensulfone.
7. One or more quinazoline derivatives represented by the formula [I] according to claim 1 as active ingredients, chlorothalonil, quinomethionate, iminoctadine albecyl acid, triflumizole, tebuconazole, difenoconazole, triadimethone, fenpropimorph One or two selected from the group of bactericidal active compounds consisting of azoxystrobin, pyraclostrobin, trifloxystrobin, cresoxime methyl, cyflufenamide, penthiopyrad, fluthianyl, quinoxyphene, thiophanate methyl, diflumetrim, and acibenzoral S.methyl A pest control composition for agricultural and horticultural use comprising the above as an active ingredient.
8. One or more quinazoline derivatives represented by the formula [I] according to claim 1 as active ingredients, chlorothalonil, manzeb, cyazofamide, amisulbrom, simoxanyl, cresoxylmethyl, azoxystrobin, metalaxyl M, mandipropamide A pest control composition for agricultural and horticultural use comprising, as an active ingredient, one or more selected from the group of bactericidal active compounds consisting of benzoavaricarb isopropyl and dimethomorph.
9. The quinazoline derivative represented by the formula [I] according to claim 1 is used as an active ingredient and is selected from the group of insecticidal active compounds consisting of acephate, imidacloprid, tolfenpyrad, acrinathrin, flonicamid, and pyrifluquinazone. A pest control composition for agricultural and horticultural use comprising one or more active ingredients as active ingredients.