TW202146397A - Azinyl azole compound and pest control agent - Google Patents

Abstract

The present invention provides: a compound represented by formula (I) or a salt thereof; and a pest control agent which contains, as an active ingredient, at least one substance that is selected from among the compounds and salts thereof. (In formula (I), X represents a halogeno group or the like; n represents the number of the X moieties, said number being an integer from 0 to 5, and when n is 2 or more, the X moieties may be the same as or different from each other; each of R1 and R2 independently represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group; R3 represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group or the like; each of Y1 and Y2 independently represents a nitrogen atom or a group represented by CRa; each Ra independently represents a hydrogen atom, a halogeno group or the like; and Q represents a substituted or unsubstituted six-membered heteroaryl group.).

Description

Azinylazole compound and pest control agent

The present invention relates to an azinylazole compound and a pest control agent. More specifically, the present invention relates to an azinylazole compound having excellent insecticidal activity and/or acaricidal activity, excellent safety, and industrially advantageously synthesizable, and harmful organisms containing the same as an active ingredient control agent. This application claims priority based on Japanese Patent Application No. 2020-037098 for which it applied in Japan on March 4, 2020, and the content is incorporated herein by reference.

Various compounds have been proposed with insecticidal/acaricidal activity. In order to use such a compound as a pesticide, it is required not only to have a sufficiently high efficacy, but also to be less likely to develop chemical resistance, not to cause phytotoxicity to plants or soil pollution, and to have low toxicity to livestock, fish, and the like.

However, Patent Document 1 describes that compounds represented by formula (A) and the like can be used to inhibit ectoparasites in animals.

[現有技術文獻] [專利文獻][hua 1]

[Prior Art Document] [Patent Document]

[Patent Document 1] WO 2017/192385 A1

[The problem to be solved by the invention] An object of the present invention is to provide an azinylazole compound which is excellent in pest control activity, especially insecticidal activity and/or acaricidal activity, and which is excellent in safety and which can be advantageously synthesized industrially. Another subject of the present invention is to provide a pest control agent, an insecticide or acaricide, an external parasite control agent, or an internal parasite control or expelling agent containing an azinylazole compound as an active ingredient.

[Means of Solving Problems] As a result of studies to solve the above-mentioned problems, the present invention including the following aspects has been completed.

[1] A compound represented by formula (I) or a salt thereof.

[hua 2]

In formula (I), X represents halogen, substituted or unsubstituted C1-6 alkyl, hydroxy, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 Alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-6 cycloalkyl , substituted or unsubstituted C3-6 cycloalkoxy, substituted or unsubstituted C3-6 cycloalkylthio, substituted or unsubstituted C3-6 cycloalkylsulfinyl, substituted or unsubstituted C3-6 cycloalkylsulfonyl, nitro or cyano group; or, X represents substituted or unsubstituted C2-6 alkynyl; n represents the number of X and is 0-5 Any integer, when n is 2 or more, X may be the same or different from each other, R ¹ represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, R ² represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group Unsubstituted C1-6 alkyl, R ³ represents a hydrogen atom, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 alkylcarbonyl, or substituted or unsubstituted C1-6 alkoxycarbonyl group, Y ¹ represents a nitrogen atom or ^a group represented by ^{CR a, Y 2} represents a nitrogen atom or ^a group represented by ^{CR a, R a} independently represents a hydrogen atom, a halogen group, or a substituted group or an unsubstituted C1-6 alkyl group, Q represents a substituted or unsubstituted 6-membered heteroaryl group.

[2] The compound or salt thereof according to [1], wherein Q is a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group. [3] A pest control agent containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [4] An insecticide or acaricide containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [5] An ectoparasite control agent containing, as an active ingredient, at least one selected from the compounds described in [1] or [2] or salts thereof. [6] An internal parasite control or expelling agent containing as an active ingredient at least one selected from the compounds described in [1] or [2] or salts thereof.

[Effect of invention] The azinylazole compound of the present invention has a function of controlling harmful organisms that are problematic in terms of crops or hygiene. The control agent containing the azinylazole compound of the present invention can effectively control harmful organisms, especially agricultural pests and mites, at a lower concentration, and further, can effectively control external parasites and internal parasites that sometimes harm humans and animals.

The azinylazole compound of the present invention is a compound represented by formula (I) or a salt thereof.

[hua 3]

Here, the term "unsubstituted" refers to a group that serves only as a parent nucleus. When there is no description of "substituted" and only the name of the group that becomes the parent nucleus is described, it means "unsubstituted" unless otherwise specified. On the other hand, the term "substituted" means that any hydrogen atom of the group that becomes the parent nucleus is substituted with a group (substituent) having the same or different structure as that of the parent nucleus. Therefore, the "substituent group" is another group bonded to the group that becomes the parent nucleus. The substituent may be one or two or more. Two or more substituents may be the same or different. Terms such as "C1 to 6" indicate that the number of carbon atoms of the group serving as the parent nucleus is 1 to 6, or the like. The number of carbon atoms present in the substituent is not included in the number of carbon atoms. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The "substituent" is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Groups that can be "substituents" are exemplified below. Methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and other C1-6 alkyl groups; vinyl, 1-propenyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl -C2-6 alkenyl such as 2-propenyl; C2-6 alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl;

C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; Phenyl, naphthyl; benzyl, phenethyl; 3- to 6-membered heterocyclic group; 3- to 6-membered heterocyclyl C1-6 alkyl;

hydroxyl; C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy; C2-6 alkenyloxy groups such as vinyloxy, allyloxy, propyleneoxy, butenyloxy; C2-6 alkynyloxy groups such as ethynyloxy, propargyloxy; Phenoxy, naphthoxy; Benzyloxy, phenethoxy and other phenyl C1-6 alkoxy; 5- to 6-membered heteroaryloxy groups such as thiazolyloxy, pyridyloxy; 5- to 6-membered heteroaryl C1-6 alkoxy groups such as thiazolylmethoxy and pyridylmethoxy;

carboxyl; C1-6 alkyl carbonyl groups such as acetyl and propionyl; methyloxy; C1-6 alkylcarbonyloxy groups such as acetyloxy, propionyloxy; benzyl; C1-6 alkoxycarbonyl groups such as methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, and tert-butoxycarbonyl; Methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, isopropoxycarbonyloxy, n-butoxycarbonyloxy, tert-butoxycarbonyloxy, etc. C1-6 alkoxycarbonyloxy; carboxyl;

Halogen groups such as fluoro, chloro, bromo, iodo, etc.; C1-6 haloalkyl groups such as chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl; 2-chloro-1-propenyl, 2-fluoro-1-butenyl and other C2-6 haloalkenyl; 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl and other C2-6 haloalkynyl; C1-6 halogenated alkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, 2,3-dichlorobutoxy; C2-6 haloalkenyloxy such as 2-chloropropenyloxy, 3-bromobutenyloxy; C1-6 haloalkylcarbonyl groups such as chloroacetyl, trifluoroacetyl, and trichloroacetyl;

amine group; C1-6 alkyl substituted amino groups such as methylamino, dimethylamino, diethylamino, etc.; Phenylamino such as aniline; Benzylamino, phenethylamino and other phenyl C1-6 alkylamino groups; formylamino; C1-6 alkylcarbonylamino groups such as acetylamino, propionylamino, butylamino, isopropylcarbonylamino, etc.; C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino, ethoxycarbonylamino, n-propoxycarbonylamino, isopropoxycarbonylamino, etc.; Aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylaminocarbonyl and other unsubstituted or substituted aminocarbonyl; Imino methyl, (1-imino) ethyl, (1-imino) n-propyl and other imino C1-6 alkyl groups; N-Hydroxy-iminomethyl, (1-(N-hydroxy)-imino)ethyl, (1-(N-hydroxy)-imino)propyl, N-methoxy-imine substituted or unsubstituted N-hydroxyimino C1-6 alkyl groups such as methyl, (1-(N-methoxy)-imino) ethyl, etc.; aminocarbonyloxy; C1-6 alkyl substituted aminocarbonyloxy such as ethylaminocarbonyloxy and dimethylaminocarbonyloxy;

Sulfhydryl; C1-6 alkylthio groups such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, second butylthio, and third butylthio; C1-6 halogenated alkylthio groups such as trifluoromethylthio, 2,2,2-trifluoroethylthio; Phenylthio, naphthylthio; 5- to 6-membered heteroarylthio groups such as thiazolylthio, pyridinethio, etc.;

C1-6 alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, and tert-butylsulfinyl; C1-6 haloalkylsulfinyl such as trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl; Phenylsulfinyl; 5- to 6-membered heteroarylsulfinyl groups such as thiazolyl sulfinyl, pyridylsulfinyl, etc.;

Methylsulfonyl, ethylsulfonyl, tert-butylsulfonyl and other C1-6 alkylsulfonyl groups; C1-6 haloalkylsulfonyl such as trifluoromethylsulfonyl, 2,2,2-trifluoroethylsulfonyl; Phenylsulfonyl; 5- to 6-membered heteroarylsulfonyl groups such as thiazolylsulfonyl and pyridylsulfonyl; Methylsulfonyloxy, ethylsulfonyloxy, tert-butylsulfonyloxy and other C1-6 alkylsulfonyloxy groups; C1-6 haloalkylsulfonyloxy such as trifluoromethylsulfonyloxy, 2,2,2-trifluoroethylsulfonyloxy;

Tri-C1-6 alkyl substituted silyl groups such as trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, etc.; triphenylsilyl; pentafluorohydrosulfanyl; cyano group; nitro group.

In addition, regarding these "substituents", any hydrogen atom in the substituents may be substituted by groups of different structures. As a "substituent" in this case, a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogen group, a cyano group, a nitro group, etc. are mentioned.

In addition, the "3- to 6-membered heterocyclic group" is a 3-membered ring, 4-membered ring including 1 to 4 heteroatoms selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom as ring constituent atoms Ring, 5-member or 6-member ring. The heterocyclic group may be either monocyclic or polycyclic. Regarding the polycyclic heterocyclic group, as long as at least one ring is a heterocyclic ring, the remaining rings may be any of saturated alicyclic, unsaturated alicyclic or aromatic rings. Examples of the "3- to 6-membered heterocyclic group" include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclic group.

Examples of the 3- to 6-membered saturated heterocyclic group include aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperazinyl, morpholinyl, and dioxa Cyclopentyl, dioxanyl, etc.

Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, and oxadiazolyl , thiadiazolyl, tetrazolyl, etc. As a 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. are mentioned.

[X, n] X represents halogen, substituted or unsubstituted C1-6 alkyl, hydroxy, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-6 cycloalkyl, substituted or unsubstituted Substituted C3-6 cycloalkoxy, substituted or unsubstituted C3-6 cycloalkylthio, substituted or unsubstituted C3-6 cycloalkylsulfinyl, substituted or unsubstituted C3-6 cycloalkylsulfonyl, nitro or cyano group; Alternatively, X represents a substituted or unsubstituted C2-6 alkynyl group. n represents the number of X and is any integer from 0 to 5. When n is 2 or more, X may be the same or different from each other.

As a "halogen group" in X, a fluorine group, a chlorine group, a bromine group, an iodine group, etc. are mentioned.

The "C1-6 alkyl group" in X may be a straight chain or a branched chain. Examples of the "C1-6 alkyl group" in X include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, sec-butyl, th Tributyl, isopentyl, neopentyl, 2-methylbutyl, isohexyl, etc.

Examples of "C1-6 alkoxy" in X include methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexyloxy, isopropoxy, isobutoxy oxy, second butoxy, third butoxy, isohexyloxy and the like.

The "C1-6 alkylthio group" in X includes methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, isopropylthio and the like.

As "C1-6 alkylsulfinyl group" in X, methylsulfinyl group, ethylsulfinyl group, tert-butylsulfinyl group, etc. are mentioned.

As "C1-6 alkylsulfonyl group" in X, methylsulfonyl group, ethylsulfonyl group, tert-butylsulfonyl group, etc. are mentioned.

As "C1-6 alkyl", "C1-6 alkoxy", "C1-6 alkylthio", "C1-6 alkylsulfinyl" or "C1-6 alkylsulfonyl" in X The substituents on the "group" are preferably: fluoro, chloro, bromo, iodo and other halogen groups; hydroxy; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy , C1-6 alkoxy such as second butoxy, isobutoxy, third butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and other C1 ~6 haloalkoxy; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. substituted phenyl"; or cyano.

As "C3-6 cycloalkyl group" in X, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, etc. are mentioned. As "C3-6 cycloalkoxy group" in X, a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, etc. are mentioned.

As "C3-6 cycloalkylthio group" in X, a cyclopropylthio group, a cyclobutylthio group, a cyclopentylthio group, a cyclohexylthio group, etc. are mentioned. Examples of "C3-6 cycloalkylsulfinyl" in X include cyclopropylsulfinyl, cyclobutylsulfinyl, cyclopentylsulfinyl, and cyclohexylsulfinyl Wait. As "C3-6 cycloalkylsulfonyl group" in X, cyclopropylsulfonyl group, cyclobutylsulfonyl group, cyclopentylsulfonyl group, cyclohexylsulfonyl group, etc. are mentioned.

As "C3-6cycloalkyl", "C3-6cycloalkoxy", "C3-6cycloalkylthio", "C3-6cycloalkylsulfinyl" or "C3-6cycloalkylsulfinyl" in X The substituents on the cycloalkylsulfonyl group are preferably: fluoro, chloro, bromo, iodo and other halogens; methyl, ethyl, n-propyl, isopropyl, n-butyl, Dibutyl, isobutyl, tert-butyl, n-pentyl, n-hexyl and other C1-6 alkyl groups; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n-propyl, 1 -C1-6 haloalkyl such as fluoro-n-butyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy C1-6 alkoxy groups such as radicals; C1-6 halogenated alkoxy groups such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy, etc.; or cyano groups.

In the present invention, X is preferably a halogen group, a halogen-substituted or unsubstituted C1-6 alkyl group, a halogen-substituted or unsubstituted C1-6 alkoxy group, or a cyano group, preferably Halogen, halogen-substituted C1-6 alkyl, halogen-substituted C1-6 alkoxy or cyano.

Examples of the "halo-substituted C1-6 alkyl group" in X include difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, 2,2,2,1,1- Pentafluoroethyl, etc. Examples of the "halo-substituted C1-6 alkoxy group" in X include difluoromethoxy, trifluoromethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoro Ethoxy, 2,2,1,1-tetrafluoroethoxy, 2,2,2,1,1-pentafluoroethoxy, etc.

Examples of "C2-6 alkynyl" in X include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-butynyl Methyl-2-propynyl and the like, preferably ethynyl.

As the substituent on the "C2-6 alkynyl" in X, preferred are halogen groups such as fluoro, chloro, bromo, iodo, etc.; hydroxy; methoxy, ethoxy, n-propoxy, C1-6 alkoxy such as isopropoxy, n-butoxy, second butoxy, isobutoxy, third butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy C1-6 halogenated alkoxy groups such as phenyl, trifluoromethoxy, etc.; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. 6 haloalkyl or C1-6 haloalkoxy substituted phenyl"; cyano group; or tri-C1-6 alkyl substituted silyl group, more preferably tri-C1-6 alkyl substituted silyl group, more preferably trimethyl substituted Silane group.

[R ¹ , R ² , R ³ ] R ¹ represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group, and R ² represents a hydrogen atom or a substituted or unsubstituted C1-6 alkyl group. R ³ represents a hydrogen atom, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylcarbonyl group, or a substituted or unsubstituted C1-6 alkoxycarbonyl group, more Preferably, it represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group.

Specific examples of the "C1-6 alkyl group" in R ¹ , R ² and R ^{3 include the same groups as those exemplified in X.} As a specific example of "C1-6 alkylcarbonyl group" in R<^3> , an acetyl group, a propionyl group, etc. are mentioned. Specific examples of "C1-6 alkoxycarbonyl" in R ³ include methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxycarbonyl, Tributoxycarbonyl, etc.

As the substituent on the "C1-6 alkyl group", "C1-6 alkylcarbonyl group" or "C1-6 alkoxycarbonyl group" in ^{R 1} , R ² or R ^{3 , preferred are: fluorine group, chlorine group} halogen, bromo, iodo, etc.; hydroxy; methoxy, ethoxy, n-propoxy, iso-propoxy, n-butoxy, second-butoxy, iso-butoxy, third-butoxy C1-6 alkoxy such as oxy; C1-6 haloalkoxy such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy; phenyl; 4-chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. "phenyl substituted by halo, C1-6 haloalkyl or C1-6 haloalkoxy"; or cyano.

In addition to the above, as ^{the substituent on the "C1-6 alkyl group" in R 3} , preferably C3-6 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl; vinyl and the like Alkenyl of C2-6; or ethynyl.

[Y ¹ , Y ² , R ^a ] Y ¹ represents a nitrogen atom or ^a group represented by CR a, preferably a nitrogen atom. Y ² represents a nitrogen atom or ^a group represented by CR a. R ^a each independently represents a hydrogen atom, a halogen group, or a substituted or unsubstituted C1-6 alkyl group, preferably a hydrogen atom or an unsubstituted C1-6 alkyl group. Specific examples of the "halo group" or "C1-6 alkyl group" in R ^{a include the same groups as those exemplified in X.}

[Q] Q represents a substituted or unsubstituted 6-membered heteroaryl group. The "6-membered heteroaryl group" in Q is a monovalent group including an aromatic 6-membered ring including one selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom, 2, 3 or 4 heteroatoms serve as ring constituent atoms. When there are two or more hetero atoms, these may be the same or different. As a 6-membered heteroaryl group, a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, a triazinyl group, etc. are mentioned. Among these, Q is preferably pyridyl, pyrimidinyl or pyridazinyl, more preferably pyridyl or pyrimidinyl.

As the substituent on the "6-membered heteroaryl group" in Q, preferred are halogen groups such as fluoro, chloro, bromo, iodo; methyl, ethyl, n-propyl, isopropyl, n-propyl, etc. C1-6 alkyl groups such as butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, n-hexyl; chloromethyl, chloroethyl, trifluoromethyl, 1,2-dichloro-n- Propyl, 1-fluoro-n-butyl and other C1-6 haloalkyl; hydroxyl; methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, second butoxy, isobutoxy C1-6 alkoxy, such as tertiary butoxy; 2-chloro-n-propoxy, 2,3-dichlorobutoxy, trifluoromethoxy and other C1-6 haloalkoxy; phenyl; 4 -Chlorophenyl, 4-trifluoromethylphenyl, 4-trifluoromethoxyphenyl, etc. "phenyl substituted by halo, C1-6 haloalkyl or C1-6 haloalkoxy"; or cyano , more preferably a halogen group, a C1-6 alkyl group, a C1-6 haloalkyl group or a cyano group.

The azinylazole compound of the present invention is not particularly limited by its production method. For example, the azinylazole compound of the present invention (hereinafter, sometimes referred to as the "compound of the present invention") can be obtained according to the procedures described in Examples and the like using a known reaction. In addition to the methods described in Examples and the like, it can also be obtained by utilizing the reactions described in the reaction schemes shown below. (Reaction Scheme 1) The outline of the preparation method of the compound represented by Formula (I) is shown in the following Reaction Scheme 1.

[hua 4]

The symbols in the formula (I) have the same meanings as those described above. The symbols in the formula (2) have the same meanings as those in the formula (I). X and n in formula (3) represent the same meanings as those in formula (I). Z represents a halogen group. Compounds of formula (I) can be prepared by reacting compounds of formula (2) with compounds of formula (3) in the presence of a suitable base. As the base, organic bases such as triethylamine and N,N-diisopropylethylamine are preferable.

(Reaction Scheme 2) The outline of the preparation method of the compound represented by Formula (2) is shown in the following Reaction Scheme 2.

[hua 5]

The symbols in the formula (4) represent the same meanings as those in the formula (I). Z' represents a halogen group. ^{R 3} in formula (5) has the same meaning as ^{R 3} in formula (I). The compound of formula (2) can be prepared by reacting the compound of formula (4) with the amine compound of formula (5).

(Reaction Scheme 3) The compound ^{represented by the formula (4') in which Y 1} is a nitrogen atom and Y ² is ^a group represented by CR a in the compound represented by the formula (4) can be represented by the following reaction scheme 3. method to prepare.

[hua 6]

The symbols in the formula (4') have the same meanings as those in the formula (I), and Z' represents a halogen group. The symbols in the formula (6) have the same meanings as those in the formula (I), and Z' represents a halogen group. ^{R a} in formula (7) has the ^{same meaning as R a} in formula (I), and Me represents a methyl group. Q in formula (8) represents the same meaning as Q in formula (I). By condensing the compound represented by the formula (6) and the compound represented by the formula (7) under heating, and then removing the low boiler (methanol in this case), in the presence of an organic acid such as acetic acid, the compound is combined with the formula (8). ) is condensed under heating conditions, so that the compound of formula (4') can be prepared. In this case, the condensate of the compound of the formula (6) and the compound of the formula (7) is considered to be the compound of the following formula (9). The symbols in the formula (9) are the same as those described above.

[hua 7]

(Reaction Scheme 4) The compound represented by the formula (3') in which the 2-position of the quinazoline ring is hydrogen among the compounds represented by the formula (3) can be produced by the method shown in the following reaction scheme 4.

[hua 8]

X in formula (3') represents the same meaning as X in formula (I), m represents any integer of 0 to 4, and Z' represents a halogen group. X in formula (10) has the same meaning as X in formula (I), and m represents any integer of 0 to 4. The compound of formula (3') can be prepared by condensing the compound of formula (10) with carboxamide under heating, and then reacting with a halogenating agent such as thionyl chloride.

The compounds of the present invention are excellent in controlling various agricultural pests and mites and other harmful organisms that affect plant growth. In addition, the compound of the present invention has little phytotoxicity to crops and low toxicity to fish or warm-blooded animals, and thus is a highly safe substance. Therefore, it is useful as an active ingredient of an insecticide or acaricide. Furthermore, in recent years, among a large number of pests such as diamondback moth, rice planthopper, leafhopper, aphids, etc., resistance to various existing chemicals has developed, resulting in the problem of insufficient efficacy of these chemicals. It is expected that the pests of resistant strains will also be effective medicine. The compounds of the present invention exhibit excellent control effects not only against pests of susceptible strains, but also against pests of various resistant strains and mites of acaricide-resistant strains.

The compounds of the present invention are excellent in preventing and controlling external parasites and internal parasites that harm humans and animals. In addition, the toxicity to fish and warm-blooded animals is low, and thus it is a highly safe substance. Therefore, it is useful as an active ingredient of a control agent for external parasites and internal parasites.

In addition, the compound of the present invention exhibits efficacy in the entire growth stage of the organism to be controlled, for example, exhibits an excellent control effect on eggs, nymphs, larvae, pupa, and adults of mites, insects, and the like.

[Pest control agents, insecticides or acaricides] The pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent of the present invention, or the insecticide or acaricide is not particularly limited as long as it exhibits a control effect against pests, agricultural pests, or mites.

The pest control agent, or insecticide or acaricide of the present invention is preferably used for cereals; vegetables; root vegetables; potatoes; flowers; fruit trees; ; pasture; turf; cotton and other plants. When applied to plants, the pest control agents, or insecticides or acaricides of the present invention can be used on leaves, stems, stalks, flowers, buds, fruits, seeds, shoots, roots, tubers, roots, branches, cuttings, etc. any part. In addition, the pest control agent, or the insecticide or acaricide of the present invention is not particularly limited by the species of plants to be applied. As a plant species, for example, a stock species, a variety, an improved species, a cultivar, a mutant, a hybrid, a Genetically Modified Organism (GMO), etc. are mentioned.

In order to control various agricultural pests and mites, the pest control agent of the present invention can be used for seed treatment, stem and leaf spreading, soil application, water surface application and the like.

Specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are shown below.

(1) Butterflies or moths of the order Lepidoptera (a) moths of the family Arctiidae, such as Hyphantria cunea, Lemyra imparilis; (b) Moths of the family Bucculatricidae, such as Bucculatrix pyrivorella; (c) moths of the family Carposinidae, such as the peach fruit moth (Carposina sasakii); (d) Moths of the family Crambidae, such as Diaphania indica, Diaphania nitidalis of the genus Diaphania spp.; for example, Ostrinia spp. ) of the Asian corn borer (Ostrinia furnacalis), the European corn borer (Ostrinia nubilalis), the hemp field bean stem borer (Ostrinia scapulalis); and the Chilo suppressalis, Cnaphalocrocis medinalis, Peach borer (Conogethes punctiferalis), southwest corn borer (Diatraea grandiosella), mulberry silk borer (Glyphodes pyloalis), cabbage borer (Hellula undalis), bluegrass stalk borer (Parapediasia teterrella); (e) moths of the family Gelechiidae, such as the sweet potato wheat moth (Helcystogramma triannulella), the cotton red bollworm (Pectinophora gossypiella), the potato wheat moth (Phthorimaea operculella), the wheat moth (Sitotroga cerealella); (f) moths of the family Geometridae, such as Ascotis selenaria; (g) moths of the family Gracillariidae, such as Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella; (h) butterflies of the family Hesperiidae, such as Parnara guttata; (i) moths of the family Lasiocampidae, such as Malacosoma neustria; (j) Moths of the family Lymantriidae, such as Lymantria dispar, Lymantria monacha of the genus Lymantria spp.; other Euproctis pseudoconspersa, Orgyia thyellina ;

(k) Moths of the family Lyonetiidae, such as Lyonetia clerkella, Lyonetia prunifoliella malinella of the genus Lyonetia spp.; (l) Moths of the family Noctuidae, such as Spodoptera depravata, Spodoptera eridania, Spodoptera exigua of the genus Spodoptera spp. ), Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; such as Autographa spp. Autographa gamma, Autographa nigrisigna; e.g. Agrotis ipsilon, Agrotis segetum of the genus Agrotis spp.; e.g. cotton bolls of the genus Helicoverpa spp. Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea; e.g. Heliothis spp. and Heliothis armigera, Heliothis virescens ; other Aedia leucomelas, Ctenoplusia agnata, Eudocima tyrannus, Mamestra brassicae, armyworm (Mythimna separata), rice borer (Naranga aenescens) , Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni; (m) moths of the family Nolidae, such as Earias insulana; (n) butterflies of the family Pieridae, such as Pieris brassicae, Pieris rapae crucivora of the genus Pieris spp.; (o) moths of the family Plutellidae, such as Acrolepiopsis sapporensis, Acrolepiopsis suzukiella of the genus Acrolepiopsis spp.; and Plutella xylostella; (p) moths of the family Pyralidae, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella; (q) moths of the family Sphingidae, such as Manduca quinquemaculata, Manduca sexta of the genus Manduca spp.;

(r) moths of the family Stathmopodidae, such as Stathmopoda masinissa; (s) moths of the family Tineidae, for example Tinea translucens; (t) Moths of the family Tortricidae, such as Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp.; for example, of Archips spp. Archips breviplicanus, Archips fuscocupreanus; other Spruce Leaf Rollers (Choristoneura fumiferana), Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Grape leaf roller (Pandemis heparana) Sparganothis pilleriana); (u) Moths of the family Yponomeutidae, eg Argyresthia conjugella.

(2) Thysanoptera pests (a) of the Phlaeothripidae family, such as Ponticulothrips diospyrsi; (b) of the Thripidae family, e.g. Frankliniella intonsa, Frankliniella occidentalis of the genus Frankliniella spp.; e.g. palm of the genus Thrips spp. Thrips palmi, Thrips tabaci; other greenhouse thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.

(3) Pests of the order Hemiptera (A) Archaeorrhyncha (a) Of the planthopper family (Delphacidae), for example the white-backed planthopper (Laodelphax striatella), the brown planthopper (Nilaparvata lugens), the sugarcane flat-horned planthopper (Perkinsiella saccharicida), the white-backed planthopper (Sogatella furcifera).

(B) Clypeorrhyncha (a) Potato leafhoppers (Empoasca fabae), Empoasca nipponica, Empoasca onukii, Itai small leafhoppers (Empoasca fabae) of the Cicadellidae family (Empoasca spp.) Green leafhopper (Empoasca sakaii); other grape leafhoppers (Arboridia apicalis), black-breasted leafhoppers (Balclutha saltuella), two-spotted leafhoppers (Epiacanthus stramineus), black-fronted leafhoppers (Macrosteles striifrons), black-tailed leafhoppers Leafhopper (Nephotettix cinctinceps).

(C) Heteroptera (a) of the family Alydidae, such as Riptortus clavatus; (b) of the family Coreidae, such as Cletus punctiger, Leptocorisa chinensis; (c) of the Lygaeidae family, such as Blissus leucopterus, Cavelerius saccharivorus, Togo hemipterus; (d) of the family Miridae, e.g. Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovitatus, Trigonotylus caelestialium;

(e) of the family Pentatomidae, e.g. Nezara antennata, Nezara viridula of the genus Nezara spp.; e.g. of the genus Eysarcoris spp. Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis; other Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, tea Halyomorpha halys, Piezodorus hybneri, Plautia crossota, Scotinophora lurida; (f) of the family Pyrrhocoridae, for example Dysdercus cingulatus; (g) of the family Rhopalidae, such as Rhopalus msculatus; (h) of the family Scutelleridae, such as Eurygaster integriceps; (i) of the Tingidae family, eg Stephanitis nashi.

(D) Sternorrhyncha (a) of the family Adelgidae, such as Adelges laricis; (b) Aleyrodidae, such as Bemisia argentifolii, Bemisia tabaci of the genus Bemisia spp.; other Aleurocanthus spiniferus, citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum); (c) Aphididae, such as Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii, Aphis gossypii, Aphis spp. (Aphis pomi), Aphis sambuci, Aphis spiraecola; e.g. Rhopalosiphum maidis, Rhopalosiphum padi of the genus Rhopalosiphum spp.; For example, Dysaphis plantaginea, Dysaphis radicola of the genus Dysaphis spp.; for example, Macrosiphum avenae of the genus Macrosiphum spp., Potato aphid (Macrosiphum euphorbiae); eg Myzus cerasi, Myzus persicae, Myzus varians of the genus Myzus spp.; other Acyrthosiphon pisum), Aulacorthum solani, Brachycaudus helichrysi, Cabbage aphid (Brevicoryne brassicae), Strawberry capillary aphid (Chaetosiphon fragaefolii), Peach powder aphid (Hyalopterus pruni), Bitter cabbage aphid (Hyalopterus pruni) Hyperomyzus lactucae, Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Nasonovia ribis-nigri (Phorodon humuli), Schizaphis graminum, Sitobion avenae, Toxoptera aurantii;

(d) Ceroplastes ceriferus, Ceroplastes rubens of the family Coccidae, such as Ceroplastes spp.; (e) Pseudaulacaspis pentagona (Pseudaulacaspis pentagona), Pseudaulacaspis prunicola (Pseudaulacaspis prunicola) of the family Diaspididae, Pseudaulacaspis spp.; Unaspis euonymi, Unaspis yanonensis; other Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theae, Peony scale (Pseudaonidia paeoniae); (f) of the family Margarodidae, for example, Drosicha corpulenta, Icerya purchasi; (g) of the Phylloxeridae family, such as Viteus vitifolii; (h) Planococcus citri, Japanese mealybugs (Planococcus kuraunhiae) of the family Pseudococcidae, e.g. Planococcus spp.; other Lycoccus solani , Pseudococcus comstocki; (i) Psyllidae (eg Psylla mali, Psylla pyrisuga) of the genus Psyllidae (Psylla spp.); other citrus psyllids (Diaphorina citri).

(4) Pests of polyphaga (Polyphaga) (a) of the family Anobiidae, such as the tobacco beetle (Lasioderma serricorne); (b) of the family Attelabidae, such as Byctiscus betulae, Rhynchites heros; (c) of the Bostrichidae family, such as Lyctus brunneus; (d) of the family Brentidae, such as the sweet potato ant weevil (Cylas formicarius); (e) of the Buprestidae family, such as Agrilus sinuatus; (f) of the family Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (g) of the Chrysomelidae family, such as Bruchus pisorum, Bruchus rufimanus; for example, Diabrotica spp. barberi), cucumber beetle (Diabrotica undecimpunctata), corn root beetle (Diabrotica virgifera); e.g. Phyllotreta nemorum, Phyllotreta striolata of the genus Phyllotreta spp. ; other yellow squash (Aulacophora femoralis), mung bean elephant (Callosobruchus chinensis), beet beetle (Cassida nebulosa), beet flea beetle (Chaetocnema concinna), potato leaf beetle (Leptinotarsa decemlineata), rice worm (Oulema oryzae) , Psylliodes angusticollis;

(h) of the family Coccinellidae, such as Epilachna varivestis, Epilachna vigintioctopunctata of the genus Epilachna spp.; (i) of the family Curculionidae, such as Anthonomus grandis, Anthonomus pomorum of the genus Anthonomus spp.; (Sitophilus granarius), corn weevil (Sitophilus zeamais); other rice weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus), pine bark weevil (Hylobius abietis), cloverleaf weevil (Hypera postica), rice water weevil Beetle (Lissohoptrus oryzophilus), grape black weevil (Otiorhynchus sulcatus), pea root nodule (Sitona lineatus), sharp beak (Sphenophorus venatus); (j) Melanotus fortnumi, Melanotus tamsuyensis of the family Elateridae, such as Melanotus spp.; (k) of the family Nitidulidae, such as Epuraea domina; (l) of the family Scarabaeidae, such as Anomala cuprea (Anomala cuprea), Anomala rufocuprea (Anomala rufocuprea); other beetles (Cetonia aurata), small Green beetles (Gametis jucunda), small chestnut beetles (Heptophylla picea), large chestnut beetles (Melolontha melolontha), Japanese beetles (Popillia japonica); (m) of the family Scolytidae, such as Ips typographus; (n) of the family Staphylinidae, such as Paederus fuscipes; (o) of the family Tenebrionidae, such as Tenebrio molitor, Tribolium castaneum; (p) of the Trogossitidae family, eg Tenebroides mauritanicus.

(5) Diptera pests (A) Diptera (Brachycera) (a) Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, three of the family Agromyzidae, such as Liriomyza spp. Leaf miner (Liriomyza trifolii); other pea color miners (Chromatomyia horticola), Japanese rice miner (Agromyza oryzae); (b) Delia platura, Delia radicum of the family Anthomyiidae, such as Delia spp.; other Pegomya cunicularia; (c) Drosophila melanogaster, Drosophila suzukii of the family Drosophilidae, such as Drosophila spp.; (d) of the family Ephydridae, such as Hydrellia griseola; (e) of the family Psilidae, such as Psila rosae; (f) of the family Tephritidae, e.g. Bactrocera cucurbitae, Bactrocera dorsalis of the genus Bactrocera spp.; e.g. cherries of the genus Rhagoletis spp. Rhagoletis cerasi, Rhagoletis pomonella; other Mediterranean fruit flies (Ceratitis capitata), olive fruit fly (Dacus oleae).

(B) Nematocera (a) Of the Cecidomyiidae family, for example Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, Sitodiplosis mosellana.

(6) Pests of the order Orthoptera (a) of the family Acrididae, such as Schistocerca americana, Schistocerca gregaria of the genus Schistocerca spp.; other Australian plague locusts (Chortoicetes terminifera), Moroccan locusts Dociosaurus maroccanus), East Asian locust (Locusta migratoria), brown locust (Locustana pardalina), red-winged locust (Nomadacris septemfasciata), small-winged rice locust (Oxya yezoensis); (b) of the family Gryllidae, such as Acheta domestica, Teleogryllus emma; (c) of the family Gryllotalpidae, such as Gryllotalpa orientalis; (d) of the Tettigoniidae, such as the greenhouse stove horse (Tachycines asynamorus).

(7) Mites (Acari) (A) Suborder Acaridida of the order Astigmata (a) Mites of the family Acaridae, eg Rhizoglyphus echinopus, Rhizoglyphus robini of the genera Rhizoglyphus spp.; eg Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; and Acarus siro, Acarus siro (Aleuroglyphus ovatus), Mycetoglyphus fungivorus;

(B) Actinedida of the order Prostigmata (a) Mites of the family Tetranychidae, such as Bryobia praetiosa, Bryobia rubrioculus of the genus Bryobia spp.; Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus kankitus Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis, Eotetranychus uncatus; e.g. Oligonychus spp.) Oligonychus hondoensis, Oligonychus ilicis, Oligonychus karamatus, Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; e.g. Panonychus spp. Panonychus citri, Panonychus mori, Panonychus ulmi; for example, Tetranychus cinnabarinus, Tetranychus spp. (Tetranychus evansi), Tetranychus kanzawai, Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Mt. Tetranychus viennensis; e.g. Aponychus corpuzae of the genus Aponychus spp., Aponychus firmianae; e.g. of the genus Sasanychus spp. ( Sasanychus akitanus), Sasanychus pusillus; eg Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi of the genus Shizotetranychus spp. ), Shizotetranychus recki, Shizotetranychus schizopus; and sorrels such as Tetranychina harti, Tuckerella pavoniformis, Yezonychus sapporensis );

(b) Mites of the family Tenuipalpidae, such as Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis of the genus Brevipalpus spp. ), Brevipalpus russulus, Brevipalpus californicus; for example Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae of Tenuipalpus spp.; and Pineapple spider mite (Dolichotetranychus floridanus); (c) mites of the family Eriophyidae, such as Aceria diospyri, Aceria ficus, Aceria japonica of the genus Aceria spp., Aceria kuko, Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; e.g. Eriophyes chibaensis, Eriophyes emarginatae of the genus Eriophyes spp.; e.g. Aculops lycopersici, Aculops spp. Aculops pelekassi; e.g. Aculus fockeui, Aculus schlechtendali of Aculus spp.; and Acaphylla theavagrans, tea gall Mite (Calacarus carinatus), grape gall mite (Colomerus vitis), grape leaf rust mite (Calepitrimerus vitis), pear gall mite (Epitrimerus pyri), chrysanthemum leaf rust mite (Paraphytoptus kikus), Paracalacarus podocarpi ), citrus rust mite (Phyllocotruta citri); (d) Mites of the family Transonemidae, such as Tarsonemus bilobatus, Tarsonemus waitei of the genus Tarsonemus spp.; and Phytonemus pallidus), Polyphagotarsonemus latus; (e) Mites of the family Penthaleidae, for example Penthaleus erythrocephalus, Penthaleus major of the genus Penthaleus spp.

The pest control agent of the present invention can be combined with other active ingredients such as fungicides, insecticides/acaricides, nematicides, soil insecticides, etc.; plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. mixed or combined. A synergistic effect related to the insecticidal/acaricidal/nematicidal activity can be expected from the combination of the compound of the present invention and other active ingredients. Synergistic effects can be determined according to prescribed methods and by the Colby formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) confirm.

Specific examples of insecticides/acaricides, nematicides, soil insecticides, insect repellents, etc. that can be mixed or used in combination with the pest control agent of the present invention are shown below.

(1) Acetylcholinesterase inhibitors: (a) Carbamate series: alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butocarboxim Butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furosemide Furathiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb ), thiofanox, triazamate, trimethacarb, Xylene Monochloride (XMC), xylylcarb, fenothiocarb, Procarb (MIPC), mites (MPMC), swiftcarb (MTMC), aldoxycarb (aldoxycarb), allyxycarb, aminocarb, bufencarb, in addition to line Cloethocarb, metam-sodium, promecarb;

(b) Organic phosphorus series: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos , chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, Demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, B Disulfoton, ethyl-p-nitrophenyl (EPN), ethion, ethopropos, famphur, fenamiphos, sulfur borer Phosphorus (fenitrothion), fenthion (fenthion), fosthiazate (fosthiazate), heptenophos (heptenophos), nicotine phosphorus (imicyafos), isofenphos (isofenphos), isocarbophos (isocarbophos) Isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, two naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, Propetaphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, s ulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, Trichlorfon, vamidothion, bromophos-ethyl, BRP, carbophenothion, cyanofenphos, methyl systemophos Demeton-S-methyl sulfone, dialifos, dichlofenthion, dioxabenzofos, etrimfos, fensulfothion, fensulfothion Phosphorus (flupyrazofos), fonofos (fonofos), formothion, fosmethilan, isazofos, jodfenphos, methacrifos, ethylpyrimidine Phosphorus (pirimiphos-ethyl), phosphocarb, propaphos, prothoate, sulprofos.

(2) Gamma Aminobutyric Acid (GABA)-operating chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole ), fipronil, pyrafluprole, pyriprole, camphechlor, heptachlor, dienochlor. (3) Sodium channel modulators: acrithrin, d-cis-trans allethrin, d-trans allethrin, Bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin ), cyfluthrin, β-cyfluthrin, cyhalothrin, λ-cyhalothrin, γ-cyhalothrin, cypermethrin ), α-cypermethrin (α-cypermethrin), β-cypermethrin (β-cypermethrin), θ-cypermethrin (θ-cypermethrin), ζ-cypermethrin (ζ-cypermethrin), cypermethrin [(1R)-trans-iso [(1R)-trans isomer] (cyphenothrin[(1R)-trans isomer]), deltamethrin, enynthrin [(EZ)-(1R)-isomer] (Empenthrin[(EZ)-(1R) -Isomer]), esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, fenvalerate Esters (flumethrin), τ-fluvalinate (τ-fluvalinate), halfenprox (halfenprox), imiprothrin (imiprothrin), kadethrin (kadethrin), permethrin (permethrin), phenyl ether Phenothrin [(1R)-trans isomer] (phenothrin[(1R)-trans isomer]), prallethrin, pyrethrum, resmethrin, fluorosilicone silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, tetrafluthrin (transfluthrin), allethrin, pyrethrin ethrins), pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, Biopermethrin, transpermethrin, fenfluthrin, fenpirithrin, flubrocythrinate, flufenprox, meth Metofluthrin, protrifenbute, pyresmethrin, terallethrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifurone, flupirimide (flupyrimine). (5) Ectopic modulators of nicotinic acetylcholine receptors: spinetoram, spinosad. (6) Chloride channel activators: abamectin, emamectin-benzoate, lepimectin, milbemectin, ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, mebe Milbemycin oxime, nemadectin. (7) Juvenile hormone analogs: hydroprene, kinoprene, methoprene, fenoxycarb, pyriproxyfen, benzite (diofenolan), epofenolan (epofenonane), methoprene (triprene). (8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic. (9) Homoptera selective feeding inhibitors: flonicamid, pymetrozine, and pyrifluquinazon.

(10) Mite fertility inhibitors: clofentezine, diflovidazin, hexythiazox, etoxazole. (11) Microorganism-derived insect midgut lining disruptors: Bacillus thuringiensis subsp. Israelensis, Bacillus sphaericus, Bacillus thuringiensis subsp. aizawai ), Bacillus thuringiensis subsp. kurstaki, Bacillus thuringiensis subsp. tenebrionis, Bt crop protein, Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab , Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1. (12) Mitochondrial ATP biosynthesis enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetrachloride Mite (tetradifon). (13) Oxidative phosphorylation uncoupling agents: chlorfenapyr, sulfluramid, dinitrocresol (DNOC), binapacryl, dinobuton, dinocap). (14) Nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereistoxin, thiosultap-sodium , Insecticide ring (thiocyclam). (15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron ( hexaflumuron), lufenuron, novaluron, polyflumuron, teflubenzuron, triflumuron, buprofezin, imidacloprid ( fluazuron). (16) Diptera molting interfering agent: cyromazine. (17) Ecdysone receptor agonists: chromafenozide, halofenozide, methoxyfenozide, tebufenozide. (18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform. (19) Mitochondrial electron transport system complex III inhibitors: acequinocyl, fluacrypyrim, hydramethylnon, bifenazate. (20) Mitochondrial electron transport system complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, fenpyroximate Amide (tolfenpyrad), rotenone (rotenone).

(21) Potential-dependent sodium channel blockers: indoxacarb, metaflumizone. (22) Acetyl CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, 3-(4-chloro-2,6-dimethyl Phenyl)-8-methoxy-1-methyl-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-ylethyl carbonate (spiropidion). (23) Mitochondrial electron transport system complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide. (24) Mitochondrial electron transport system complex II inhibitors: cyenopyrafen, cyflumetofen, pyflubumide. (25) Rianodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, fluorine Cyaniliprole (tetraniliprole). (26) Mixed-function oxidase inhibitor compounds: piperonyl butoxide. (27) Spider toxin receptor agents: depsipeptide, cyclodepsipeptide, 24-membered cyclodepsipeptide, emodepside. (28) Other agents (mechanism of action unknown): 3-endo-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[5-(trifluoromethyl)-2-pyridine Oxy]-9-azabicyclo[3.3.1]nonane (acynonapyr), azadirachtin, benzoximate, bromopropylate, quinomethionate, cryolite (cryolite), dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene , Dichloroisopropyl ether (DCIP), phenisobromolate, benzomate, metaldehyde, chlorobenzilate, clothiazoben, ringworm Dicyclanil, fenoxacrim, fentrifanil, flubenzimine, fluphenazine, gossyplure, scarabs japonilure, metoxadiazone, oil, sodium oleate, tetrasul, triarathene, afidopyropen, flumetropone ( flometoquin, flufiprole, fluensulfone, meperfluthrin, tetramethylfluthrin, tralopyril, methyl neodecyl Methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl) -5-Trifluoromethyl-4,5-dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49 -3) (5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4,5-dihydroisoxazole-3-yl]-2-(1H-1,2,4-triazole-1-yl)benzonitril e (CAS: 943137-49-3)), broflanilide, triflumezopyrim, dicloromezotiaz, 2-[3-(ethylsulfonyl) -2-Pyridyl]-5-[(trifluoromethyl)sulfonyl]benzoxazole (oxazosulfyl), other metadiamids, N-[3-chloro-1-(3-pyridyl) ) pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]propionamide (tyclopyrazoflor).

(29) Insect repellent: (a) Benzimidazole series: fenbendazole, albendazole, triclabendazole, oxibendazole, mebendazole, orphen oxfendazole, parbendazole, flubendazole, febantel, netobimin, thiophanate, thiabendazole, Cambendazole; (b) Salicylaniline series: closantel, oxyclozanide, rafoxanide, niclosamide; (c) Substituted phenols: nitroxinil, nitroscanate; (d) Pyrimidine series: pyrantel, morantel; (e) Imidazothiazoles: levamisole, tetramisole; (f) tetrahydropyrimidines: praziquantel, epsiprantel; (g) Other anthelmintics: cyclodiene, ryania, clorsulon, metronidazole, demiditraz, piperazine ), diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetarsamide, melamine Melarsomine, arsenamide.

Specific examples of fungicides that can be used in combination or in combination with the pest control agent of the present invention are shown below. (A) Nucleic acid anabolic inhibitors (1) RNA polymerase I inhibitor benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M; oxadixyl; furalaxyl Amine (ofurace). (2) Adenosine deaminase inhibitors Bupirimate, Dimethirimol, Ethirimol. (3) DNA/RNA biosynthesis inhibitors Hymexazol, octhilinone. (4) DNA topoisomerase type II inhibitors oxolinic acid.

(B) Inhibitors of cytoskeleton and motor proteins (1) β-tubulin polymerization inhibitor Benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, acetocarb ( diethofencarb), zoxamide, ethaboxam. (2) Other inhibitors Pencycuron; fluopicolide; phenamacril, metrafenone, pyriofenone.

(C) Respiratory Depressants (1) Complex I: Inhibitor of NADH oxidoreductase Diflumetorim, tolfenpyrad, fenazaquin. (2) Complex II: an inhibitor of succinate dehydrogenase Benodanil, flutolanil, mepronil; isofetamid; fluopyram; fenfuram; Carboxin, oxycarboxin; thifluzamide; benzovindiflupyr, bixafen, fluindapyr, fluazole Fluxapyroxad, furametpyr, inpyrfluxam, isopyrazam, penflufen, penthiopyrad , Fluoxafen (sedaxane); Isoflucypram (isoflucypram); Fluoxamethoxamine (pydiflumetofen); (3) Complex III: Inhibitor of cytochrome bc1 (ubiquinol oxidase) Qo site (cyt b gene) Azoxystrobin, coumoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin; Mandestrobin; pyraclostrobin, pyrametostrobin, triclopyricarb; kresoxim-methyl, trifloxystrobin; dimoxystrobin ), fenaminstrobin, metminostrobin, orysastrobin; famoxadone; fluoxastrobin; fenamidone; Pyribencarb (pyribencarb). (4) Complex III: an inhibitor of the Qi site of ubiquinone reductase Cyazofamid; Amisulbrom; Fenpicoxamid. (5) Uncouplers of oxidative phosphorylation Music kills mites (binapacryl), eliminates mites (dinocap), eliminates mites and more (meptyldinocap); fluazinam (fluazinam). (6) Inhibitors of oxidative phosphorylation and ATP synthesis enzymes Triphenyl tin acetate (fentin acetate), triphenyl tin chloride (fentin chloride), triphenyl tin hydroxide (fentin hydroxide). (7) Inhibitors of ATP transport Silthiofam. (8) Complex III: Inhibitor of ubiquinone reductase (Qo site, paxillin binding site) Ametoctradin.

(D) Inhibitors of amino acid and protein synthesis Cyprodinil, mepanipyrim, pyrimethanil; blasticidin-S; kasugamycin, kasugamycin hydrochloride, streptomycin Streptomycin; oxytetracycline.

(E) Signaling inhibitors quinoxyfen, proquinazid; fenpiclonil, fludioxonil; chlozolinate, dimetachlone, iprodione, Procymidone, vinclozolin.

(F) Agents that inhibit lipid biosynthesis or transport/structure or function of cell membranes Gram blast powder (edifenphos), different rice blast net (iprobenfos), pyrazophos (pyrazophos); rice blast spirit (isoprothiolane). Biphenyl, chloroneb, dichloran, quintozene, tecnazene, tolclofos-methyl; soil Etridiazole; iodocarb, propamocarb, propamocarb-hydrochloride, prothiocarb; natamycin ); oxathiapiprolin.

(G) Cell membrane sterol biosynthesis (inhibitor) (1) Inhibitor of sterol biosynthesis C14 demethylase (erg11/cyp51) Triforine; pyrifenox, pyrisoxazole; fenarimol, nuarimol; imazalil, oxpoconazole , pefurazoate, prochloraz, triflumizole; azaconazole, bitertanol, bromuconazole, cyproconazole ( cyproconazole), difenoconazole, diniconazole, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole (flusilazole), flutriafol, hexaconazole, imibenconazole, ipconazole, metconazole, myclobutanil, penconazole ), propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, Prothioconazole. (2) Inhibitors of Δ14 reductase and Δ8→Δ7-isomerase (erg24, erg2) in sterol biosynthesis aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, powdery mildew (piperalin); spiroxamine. (3) Inhibitor of 3-ketoreductase (erg27) in C4 demethylation of sterol biosynthesis system Cyclofenamide (fenhexamid), fenpyrazamine (fenpyrazamine). (4) Inhibitors of squalene epoxidase (erg1) in the sterol biosynthesis system Barnyard grass Dan (pyributicarb), naftifine (naftifine), terbinafine (terbinafine).

(H) Inhibitors of cell wall biosynthesis Polyoxins; dimethomorph, flumorph, pyrimorph; benthiavalicarb, iprovalicarb, valactin (valifenalate); mandipropamid.

(I) Inhibitors of cell wall melanin synthesis fthalide; pyroquilon; tricyclazole; carpropamid, diclocymet, fenoxanil; toprol card (tolprocarb).

(P) Resistance inducers of host plants Acibenzolar-S-methyl; probenazole; tiadinil, isotianil; laminarin; Knotweed extract Reynoutria sachalinensis extract; Bacillus mycoides isopate J; triethylphosphonic acid (fosetyl), phosphorous acid and salts, calcium triethylphosphonate (fosetyl-calcium), sodium triethylphosphonate ( fosetyl-sodium).

(U) Agents of unknown mechanism of action Cymoxanil; tecloftalam; triazoxide; flusulfamide; diclomezine; cyflufenamid; dodine, poly Dodine free base; flutianil; ferimzone; tebufloquin; picarbutrazox; validamycin. Fluoxapiprolin, florylpicoxamid, fluopimide, ipflufenoquin, metyltetraprole, pyridazine pyridachlometyl, pyrapropoyne, aminopyrifen, dichlobentiazox, Ipfentrifluconazole, mefentrifluconazole , quinofumelin, dipymetitrone.

(M) Agents exhibiting multi-point contact activity Copper (various salts), alkaline copper sulfate, bordeaux mixture, copper hydroxide, copper naphthalate, copper oxychloride, copper sulfate , copper oxide (copper oxide), oxine copper (oxine copper); sulfur (sulfur), lime sulfur mixture; ferbam (ferbam), mancozeb (Manzeb), manganese (maneb), mangosteen (metiram), methyl desen zinc (propineb), thiuram (thiuram), thiazole zinc, desen zinc (zineb), ziram (ziram); Folpet; chlorothalonil; dichlofluanid, tolylfluanid; guazatine, guazatine acetate, iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate; anilazine; dithianon; quinomethionate; fluoroimide); sulfocarb (methasulfocarb).

Specific examples of plant conditioners that can be used in combination or in combination with the pest control agent of the present invention are shown below. 1-Methylcyclopropene, 2,3,5-Triiodobenzoic acid, Indoleacetic acid (IAA), Indolebutyric acid (IBA), 2-Methyl-4-chlorophenoxyacetic acid (MCPA), Dimethicone Tetrachlorobutyric acid (MCPB), 4-CPA, 5-aminoacetyl propionate hydrochloride, 6-benzylaminopurine, abscisic acid, tetraethrone hydrochloride, pyrimidinol ( ancymidol, butralin, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, Chlormequat Chloride, Chlorpropham, choline chloride, Cloprop, cyanamide, Cyclanilide, daminozide, decyl alcohol, 2,4-propionic acid (dichlorprop), dikegulac, Dimethipin, Diquat, ethephon, ethychlozate, Flumetralin, flurprimidol, forchlorfenuron, gibberellin A (gibberellin A), gibberellin A3 (gibberellin A3), hymexazol, inabenfide, isoprothiolane, kinetin, hydrazine maleate, fluorine Mefluidide, mepiquat chloride, oxidized glutathione, paclobutrazol, pendimethalin, prohexadione-calcium, jasmonone ( Prohydrojasmon), Pyraflufen-ethyl, Sintofen, Sodium 1-naphthalene acetate, Sodium cyanate, Streptomycin, Thidiazuron, Triapenthenol, Trinexapac-ethyl, uniconazole P, 1-naphthylacetamide.

[External parasite control agent] The ectoparasite control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the ectoparasite control agent of the present invention is not particularly limited as long as the ectoparasite control effect is exhibited.

Examples of host animals to be treated by the ectoparasite control agent of the present invention include pet animals such as dogs and cats; pet birds; livestock such as cattle, horses, pigs, and sheep; and warm-blooded animals such as poultry. In addition, can also list: bees, stag beetles, unicorns.

The ectoparasite control agent of the present invention can be administered by a known veterinary method (topical, oral, parenteral or subcutaneous administration). Examples of this method include: a method of oral administration to animals by mixing tablets, capsules, feed, etc.; a method of administering to animals by infusion, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. Methods of animal administration; methods of topical administration of oily or aqueous liquid preparations by spraying, pouring on, spot on, etc.; The kneaded product is formed into a suitable shape such as a collar and an ear tag, and it is worn on an animal, thereby a method of topical administration and the like.

External parasites live in and on host animals, especially warm-blooded animals. More specifically, it is parasitic on the back, underarm, lower abdomen, inner thigh, etc. of a host animal to obtain a nutrient source such as blood or dander from the animal and live. Examples of external parasites include mites, lice, fleas, mosquitoes, sting flies, hemp flies, and the like. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Mites (Acari) Mites of the family Dermanyssidae, mites of the family Macronyssidae, mites of the family Laelapidae, mites of the family Varroidae, mites of the family Argasidae, mites of the family Argasidae, mites of the family Ixodidae, mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae , stag beetles and other insect parasitic mites. (2) Phthiraptera lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, lice of the family Trichodectidae Bird lice. (3) Siphonaptera Fleas of the family Pulicidae, for example Ctenocephalides canis, Ctenocephalides felis of the genus Ctenocephalides spp.; Fleas of the family Tungidae, fleas of the family Ceratophyllidae, and fleas of the family Leptopsyllidae. (4) Hemiptera. (5) Diptera pests Mosquitoes of the family Culicidae, gnats of the family Simuliidae, midges of the family Ceratopogonidae, flies of the family Tabanidae, flies of the family Muscidae, tsetse flies of the family Glossinidae , Hemp flies of the family Hempfly, flies of the family Hippoboscidae, flies of the family Calliphoridae, flies of the family Oestridae.

[Internal parasite control or repellent] The internal parasite controlling or expelling agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the internal parasite controlling or expelling agent of the present invention is not particularly limited as long as the control effect of internal parasites is exhibited.

The parasite to be the object of the internal parasite control or expelling agent of the present invention is parasitic (internal parasite) in a host animal, especially a warm-blooded animal or a fish. Examples of effective host animals for the internal parasite control or expelling agent of the present invention include humans, livestock mammals (for example, cattle, horses, pigs, sheep, goats, etc.), experimental animals (for example, mice, rats, gerbils, etc.), pet animals (e.g., hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, bison, etc.), poultry (turkeys, etc.) , ducks, chickens, quails, geese, etc.), pet birds (pigeons, parrots, nine-official birds, birds, parrots, white-backed birds, canaries, etc.) and other warm-blooded animals; or salmon, trout, koi and other fish. Parasitic diseases transmitted by parasites can be prevented or treated by controlling and expelling parasites.

Examples of parasites targeted for control or extermination include the following. (1) Nematodes of the order Dioctophymatida (a) Dioctophyma renale of the family Dioctophymatidae, such as Dioctophyma renale of the genus Dioctophyma spp.; (b) Sable worms of the family Soboliphymatidae, for example Soboliphyme abei, Soboliphyme baturini of the genus Soboliphyme spp.

(2) Nematodes of the order Trichocephalida (a) Trichinella of the family Trichinellidae, such as Trichinella spiralis of the genus Trichinella spp.; (b) Trichuris of the family Trichuridae, such as Capillaria annulata, Capillaria contorta, Capillaria hepatica, perforator of Capillaria spp. Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris vulpis, Trichuris discolor, sheep Trichuris ovis, Trichuris skrjabini, Trichuris suis.

(3) Nematodes of the order Rhabditida Strongyloides of the family Strongyloididae, such as Strongyloides papillosus of the genus Strongyloides (Strongyloides spp.), Strongyloides planiceps, Strongyloides ransomi), Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti.

(4) Nematodes of the order Strongylida Hookworms of the family Ancylostomatidae, e.g. Ancylostoma braziliense, Ancylostoma caninum, Ancylostoma duodenale, Ancylostoma duodenale of the genus Ancylostoma spp. Nematodes (Ancylostoma tubaeforme); Uncinaria stenocephala of the genus Uncinaria stenocephala; Bunostomum phlebotomum and Bunostomum of the genus Bunostomum spp. trigonocephalum).

(5) Nematodes of the order Strongylida (a) Nematodes of the family Angiostrongylidae, such as Aelurostrongylus abstrusus of the genus Aelurostrongylus spp.; Angiostrongylus vasorum of the genus Angiostrongylus spp., Angiostrongylus cantonesis; (b) nematodes of the family Crenosomatidae, such as Crenosoma aerophila, Crenosoma vulpis of the genus Crenosoma spp.; (c) nematodes of the family Filaroididae, such as Filaroides hirthi, Filaroides osleri of the genus Filaroides spp.; (d) Metastrongylus species of the family Metastrongylidae, such as Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus asymmetricus of the genus Metastrongylus spp. Nematodes (Metastrongylus pudendotectus), Metastrongylus salmi; (e) Syngamus skrjabinomorpha of the family Syngamus spp. , Syngamus trachea.

(6) Nematodes of the order Strongylida (a) nematodes of the family Molineidae, for example Nematodirus filicollis, Nematodirus spathiger of the genus Nematodirus spp.; (b) nematodes of the family Dictyocaulidae, such as Dictyocaulus filaria, Dictyocaulus viviparus of the genus Dictyocaulus spp.; (c) Nematodes of the family Haemonchidae, such as Haemonchus contortus of the genus Haemonchus spp.; (Mecistocrirus digitatus); (d) nematodes of the family Haemonchidae, such as Ostertagia ostertagi of the genus Ostertagia spp.; (e) Nematodes of the family Heligmonellidae, such as Nippostrongylus braziliensis of the genus Nippostrongylus spp.; (f) Nematodes of the family Trichostrongylidae, such as Trichostrongylus axei, Trichostrongylus colubriformis, Trichostrongylus of the genus Trichostrongylus spp. tenuis); Hyostrongylus rubidus of Hyostrongylus spp.; Obeliscoides cuniculi of Obeliscoides spp.

(7) Nematodes of the order Strongylida (a) Nematodes of the family Chabertiidae, such as Chabertia ovina of the genus Chabertia spp.; Oesophagostomum of the genus Oesophagostomum spp. brevicaudatum, Oesophagostomum columbianum, Oesophagostomum dentatum, Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, esophagus Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophagostomum watanabei; (b) Nematodes of the family Stephanuridae, such as Stephanurus dentatus of the genus Stephanurus spp.; (c) Nematodes of the family Strongylidae, such as Strongylus asini, Strongylus edentatus, Strongylus equinus, Strongylus equinus of the genus Strongylus spp. (Strongylus vulgaris).

(8) Nematodes of the order Oxyurida Nematodes of the family Oxyuridae, e.g. Enterobius anthropopitheci, Enterobius vermicularis of Enterobius spp.; Nematode (Oxyuris equi); Passalurus ambiguus of the genus Passalurus spp.

(9) Nematodes of the order Ascaridida (a) nematodes of the family Ascaridiidae, such as Ascaridia galli of the genus Ascaridia spp.; (b) Nematodes of the family Heterakidae, such as Heterakis beramporia, Heterakis brevispiculum, Heterakis of the genus Heterakis spp. gallinarum), Heterakis pusilla, Heterakis putautralis; (c) nematodes of the family Anisakidae, such as Anisakis simplex of the genus Anisakis spp.; (d) Nematodes of the family Ascarididae, such as Ascaris lumbricoides, Ascaris suum of the genus Ascaris spp.; Parascaris equine of the genus Parascaris spp. equorum); (e) Nematodes of the family Toxocaridae, such as Toxocara canis of the genus Toxocara spp., Toxocara leonina, Toxocarasuum, Toxocara vitulorum, Toxocara cati.

(10) Nematodes of the order Spirurida (a) Nematodes of the family Onchocercidae, such as Brugia malayi of the genus Brugia spp., Brugia pahangi, Paet Brugia patei; Dipetalonema reconditum of Dipetalonema spp.; Dirofilaria immitis of Dirofilaria spp.; Filaria Filaria oculi of the genus Filaria spp.; Onchocerca cervicalis of the genus Onchocerca spp., Onchocerca gibsoni, laryngeal tumor Onchocerca gutturosa; (b) Nematodes of the family Setariidae, e.g. Setaria digitata, Setaria equina, Papilloma spp. (Setaria spp.) Setaria labiatopapillosa), Setaria marshalli; Wuchereria bancrofti of Wuchereria spp.; (c) Nematodes of the family Filariidae, such as Parafilaria multipapillosa of the genus Parafilaria spp.; Crown worms of the genus Stephanofilaria spp. ( Stephanofilaria assamensis), Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

(11) Nematodes of the order Spirurida (a) nematodes of the family Gnathostomatidae, such as Gnathostoma doloresi, Gnathostoma spinigerum of the genus Gnathostoma spp.; (b) Nematodes of the family Habronematidae, such as Habronema majus, Habronema microstoma, Habronema muscae of the genus Habronema spp.; Draschia megastoma of the genus (Draschia spp.); (c) Nematodes of the family Physalopteridae, such as Physaloptera canis of the genus Physaloptera spp., Physaloptera ceticillata, Physaloptera erdocyona), Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera praeputialis Such as Physaloptera pseudopraerutialis, Physaloptera rara, Physaloptera sibirica, Physaloptera vulpineus; (d) Nematodes of the family Gongylonematidae, such as Gongylonema pulchrum of the genus Gongylonema spp.; (e) nematodes of the family Spirocercidae, such as Ascarops strongylina of the genus Ascarops spp.; (f) Nematodes of the family Thelaziidae, such as Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Lourdes of the genus Thelazia spp. Western sucking nematode (Thelazia rhodesi), Scriabin's sucking nematode (Thelazia skrjabini).

[Controlling agents related to other pests] In addition, the compound of the present invention is used for the pests that have poisonous needles or venoms and can harm humans and animals, pests that spread various pathogens/pathogens, and pests that give unpleasantness to humans (toxic pests/sanitary pests/unpleasant pests, etc.). The control effect is excellent.

Specific examples thereof are shown below. (1) Pests of the order Hymenoptera Bees of the family Argidae, bees of the family Cynipidae, bees of the family Diprionidae, ants of the family Formicidae, bees of the family Mutillidae, family Vespidae bee.

(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipede (millipede), crustaceans (crustacea), bed bugs (Cimex lectularius).

[Preparation formula] Several formulation examples of the pest control agent, insecticide or acaricide, external parasite control agent, or internal parasite control or expelling agent of the present invention are shown, but the additives and the addition ratio should not be limited to these formulations The formulations of the examples can vary widely. The "parts" and "%" in the formulation are the quality standards.

The formulation formulations for agriculture and horticulture and rice are shown below. (Formulation 1: Hydrating Agent) 40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate, and 3 parts of alkylnaphthalene sulfonate were uniformly mixed and pulverized to fineness to obtain a hydrating agent containing 40% of active ingredients. (Formulation 2: Emulsion) 30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide and 7 parts of polyoxyethylene alkyl allyl ether were mixed and dissolved to obtain an emulsion of 30% of active ingredients. (Formulation 3: Granules) 5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and pulverized until fine, and then granulated in the form of granules having a diameter of 0.5 mm to 1.0 mm, thereby Available in 5% active ingredient granules. (Formulation 4: Granules) 5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinic acid sodium salt, and 1 part of potassium phosphate were thoroughly pulverized and mixed, and water was added and thoroughly kneaded, and then granulated and dried. , so as to obtain granules with 5% active ingredients. (Formulation 5: Suspension) Mix 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylate, 10 parts of glycerin, 0.2 parts of xanthan gum and 73.8 parts of water, and wet pulverize until particle size A suspension of 10% of the active ingredient was obtained until it became 3 microns or less.

The formulation formulation of an external parasite control agent, or an internal parasite control or expelling agent is shown below. (Formulation 6: Granules) A solution obtained by dissolving 5 parts of the compound of the present invention in an organic solvent was sprayed onto 94 parts of kaolin clay and 1 part of white carbon, and then the solvent was evaporated under reduced pressure. The pellets can be mixed with animal baits. (Formulation 7: Injectable) 0.1 part to 1 part of the compound of the present invention and 99 parts to 99.9 parts of peanut oil are uniformly mixed, and then, filtration and sterilization are performed using a sterilizing filter. (Formulation 8: pouring agent) 5 parts of the compound of the present invention, 10 parts of myristate, and 85 parts of isopropyl alcohol were uniformly mixed to obtain a pour-on agent. (Formulation 9: Spot Paint) 10 to 15 parts of the compound of the present invention, 10 parts of palmitate, and 75 to 80 parts of isopropyl alcohol are uniformly mixed to obtain a spot coating agent. (Formulation 10: Spray) 1 part of the compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol were uniformly mixed to obtain a spray.

Next, a synthesis example is shown, and the present invention is further described in detail. Wherein, the present invention is not limited in any way by the following synthesis examples.

[Example 1] 6-Bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazoline -4-Amino[6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4 -amine] (synthesis of compound No. A-2)

(step 1) Synthesis of 2-amino-5-bromo-3-(trifluoromethyl)benzoic acid

[Chemical 9]

2-Amino-3-(trifluoromethyl)benzoic acid (1.5 g) was dissolved in N,N-dimethylformamide (10 ml). The solution was cooled to 0°C, and N-bromosuccinimide (1.4 g) was added thereto. The temperature of the solution was raised to room temperature and stirred overnight. Then, the solvent was distilled off from the obtained liquid by reducing pressure. Water was added thereto, followed by stirring at 0°C for 10 minutes. The obtained liquid was filtered, the obtained solid content was washed with water and hexane in this order, and dried under reduced pressure to obtain 2.0 g of the target product (yield: 96%).

(step 2) Synthesis of 6-bromo-8-(trifluoromethyl)quinazolin-4-ol [6-bromo-8-(trifluoromethyl)quinazolin-4-ol]

[Chemical 10]

2-Amino-5-bromo-3-(trifluoromethyl)benzoic acid (2.0 g) was dissolved in carboxamide (5.0 mL). The solution was stirred at 150°C overnight. The obtained liquid was cooled to 0°C. Then, it filtered, the obtained solid content was wash|cleaned with water and hexane in this order, and it dried under reduced pressure, and obtained 1.7 g of target objects (yield 84%).

(step 3) Synthesis of 6-bromo-4-chloro-8-(trifluoromethyl)quinazoline [6-bromo-4-chloro-8-(trifluoromethyl)quinazoline]

[Chemical 11]

To thionine chloride (5.0 mL) was added 6-bromo-8-(trifluoromethyl)quinazolin-4-ol (1.7 g), followed by a few drops of N,N-dimethylformamide . It was stirred under reflux with heating overnight. Then, cool to room temperature. The obtained solution was cooled in an ice bath, and then added to a saturated aqueous sodium bicarbonate solution. This was extracted with ethyl acetate, the organic phase was washed with saturated brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 1.6 g of the target compound (yield: 88%).

[Synthesis of 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine]

(step 4) 2-(5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl)pyridine[2-(5-(1-bromoethyl)-1H-1,2,4-triazol Synthesis of -1-yl)pyridine]

[Chemical 12]

2-Bromopropanamide (5.0 g) was dissolved in dichloromethane (165 mL). N,N-dimethylformamide dimethyl acetal (6.6 mL) was added thereto, and the mixture was stirred with heating under reflux for 1.5 hours. The obtained liquid was concentrated under reduced pressure. The obtained concentrate was dissolved in a mixture of dioxane (66 mL) and acetic acid (66 mL). Thereto was added 2-hydrazinopyridine (4.3 g), and the mixture was stirred under reflux with heating for 5 hours. The obtained liquid was concentrated under reduced pressure. Then, ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added, followed by extraction with ethyl acetate. The obtained organic phase was dried with anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure. The obtained concentrate was purified by silica gel column chromatography to obtain 5.4 g of the target compound (yield: 65%).

(step 5) 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine[1-(1-(pyridin-2-yl)-1H- Synthesis of 1,2,4-triazol-5-yl)ethan-1-amine]

[Chemical 13]

To 2-(5-(1-bromoethyl)-1H-1,2,4-triazol-1-yl)pyridine (1 g) was added 7 N methanol to dissolve ammonia (18.5 mL) in a sealed tube and stirred at 60°C for 4 hours. It was cooled to room temperature, and concentrated under reduced pressure to obtain a concentrate (0.88 g).

(step 6) 6-Bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazoline -4-Amino[6-bromo-N-(1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethyl)-8-(trifluoromethyl)quinazolin-4 -amine] synthesis

[Chemical 14]

6-Bromo-4-chloro-8-(trifluoromethyl)quinazoline (100 mg) was dissolved in N,N-dimethylformamide (3 ml). To this were added 1-(1-(pyridin-2-yl)-1H-1,2,4-triazol-5-yl)ethane-1-amine (87 mg) and N,N-diisopropyl Ethylamine (124 mg), stirred at 150 °C for 0.5 h using a microwave device. The obtained liquid was purified by silica gel chromatography. The fraction containing the target substance was concentrated, and the obtained solid content was washed with hexane to obtain 125 mg of the target substance (yield: 84%).

Table 1 shows examples of the compounds of the present invention produced by the same method as in the above-mentioned Examples. Enter the physical properties of the compound in the "physical properties" column. As physical property data, melting point (m.p.) is recorded.

m.p. 220℃以上（UP） A-2

m.p. 219℃-221℃ A-3

m.p. 238℃-239℃ A-4

m.p. 236℃-237℃ [Table 1] Compound number Structural formula physical properties A-1

mp above 220℃ (UP) A-2

mp 219℃-221℃ A-3

mp 238℃-239℃ A-4

mp 236℃-237℃

Furthermore, examples of the compounds of the present invention are shown in the following table. In addition, in the structural formula, an iodo group is represented using "J".

黏性油（VISCOUS OIL） A-6

m.p. 220℃ A-7

m.p. 239℃-241℃ A-8

m.p. 173℃-174℃ A-9

m.p. 223℃-224℃ [Table 2] Compound number Structural formula physical properties A-5

VISCOUS OIL A-6

mp 220℃ A-7

mp 239℃-241℃ A-8

mp 173℃-174℃ A-9

mp 223℃-224℃

m.p. 255℃-264℃ A-11

m.p. 234℃-238℃ A-12

m.p. 236℃-239℃ A-13

m.p. 253℃-256℃ A-14

m.p. 201℃-205℃ [table 3] Compound number Structural formula physical properties A-10

mp 255℃-264℃ A-11

mp 234℃-238℃ A-12

mp 236℃-239℃ A-13

mp 253℃-256℃ A-14

mp 201℃-205℃

m.p. 276℃-278℃ A-16

m.p. 200℃-209℃ A-17

m.p. 243℃-245℃ A-18

m.p. 248℃-253℃ A-19

m.p. 222℃-228℃ [Table 4] Compound number Structural formula physical properties A-15

mp 276℃-278℃ A-16

mp 200℃-209℃ A-17

mp 243℃-245℃ A-18

mp 248℃-253℃ A-19

mp 222℃-228℃

m.p. 216℃-218℃ A-21

m.p. 259℃-262℃ A-22

m.p. 229℃-235℃ A-23

m.p. 257℃-264℃ A-24

m.p. 222℃-226℃ [table 5] Compound number Structural formula physical properties A-20

mp 216℃-218℃ A-21

mp 259℃-262℃ A-22

mp 229℃-235℃ A-23

mp 257℃-264℃ A-24

mp 222℃-226℃

m.p. 176℃-177℃ A-26

m.p. 197℃-199℃ A-27

m.p. 216℃-218℃ A-28

m.p. 133℃-135℃ A-29

m.p. 194℃-196℃ [Table 6] Compound number Structural formula physical properties A-25

mp 176℃-177℃ A-26

mp 197℃-199℃ A-27

mp 216℃-218℃ A-28

mp 133℃-135℃ A-29

mp 194℃-196℃

非晶質（AMORPHOUS） A-31

m.p. 227℃-229℃ A-32

m.p. 243℃-244℃ A-33

m.p. 257℃-260℃ A-34

m.p. 242℃-243℃ [Table 7] Compound number Structural formula physical properties A-30

Amorphous (AMORPHOUS) A-31

mp 227℃-229℃ A-32

mp 243℃-244℃ A-33

mp 257℃-260℃ A-34

mp 242℃-243℃

m.p. 300℃ A-36

m.p. 220℃-221℃ A-37

m.p. 232℃-233℃ A-38

m.p. 162℃-164℃ A-39

m.p. 209℃-210℃ [Table 8] Compound number Structural formula physical property A-35

mp 300℃ A-36

mp 220℃-221℃ A-37

mp 232℃-233℃ A-38

mp 162℃-164℃ A-39

mp 209℃-210℃

非晶質（AMORPHOUS） A-41

m.p. 168℃-169℃ A-42

m.p. 274℃-275℃ A-43

m.p. 210℃-212℃ A-44

m.p. 119℃-120℃ [Table 9] Compound number Structural formula physical property A-40

Amorphous (AMORPHOUS) A-41

mp 168℃-169℃ A-42

mp 274℃-275℃ A-43

mp 210℃-212℃ A-44

mp 119℃-120℃

m.p. 281℃-283℃ A-46

m.p. 300℃ A-47

m.p. 258℃-261℃ A-48

m.p. 230℃-231℃ A-49

m.p. 145℃-147℃ [Table 10] Compound number Structural formula physical properties A-45

mp 281℃-283℃ A-46

mp 300℃ A-47

mp 258℃-261℃ A-48

mp 230℃-231℃ A-49

mp 145℃-147℃

m.p. 229℃-230℃ A-51

m.p. 262℃-265℃ A-52

黏性油（VISCOUS OIL） A-53

m.p. 283℃-285℃ A-54

m.p. 210℃-213℃ [Table 11] Compound number Structural formula physical property A-50

mp 229℃-230℃ A-51

mp 262℃-265℃ A-52

VISCOUS OIL A-53

mp 283℃-285℃ A-54

mp 210℃-213℃

m.p. 196℃-198℃ A-56

m.p. 247℃-248℃ A-57

非晶質（AMORPHOUS） A-58

非晶質（AMORPHOUS） A-59

m.p. 243℃-245℃ [Table 12] Compound number Structural formula physical property A-55

mp 196℃-198℃ A-56

mp 247℃-248℃ A-57

Amorphous (AMORPHOUS) A-58

Amorphous (AMORPHOUS) A-59

mp 243℃-245℃

m.p. 107℃-108℃ A-61

m.p. 221℃-222℃ A-62

m.p. 200℃-202℃ A-63

非晶質（AMORPHOUS） [Table 13] Compound number Structural formula physical properties A-60

mp 107℃-108℃ A-61

mp 221℃-222℃ A-62

mp 200℃-202℃ A-63

Amorphous (AMORPHOUS)

Regarding the compounds described as viscous oil (VISCOUS OIL) or amorphous (AMORPHOUS) in the physical properties column of the compounds in the table, ¹ H-NMR (Nuclear Magnetic Resonance, NMR) data are shown below. Compound No. A-30: ¹ H-NMR (CDCl ₃ , δ ppm) 8.61 (s, 1H), 8.27 (s, 1H), 8.26 (s, 1H), 8.09 (s, 1H), 8.05 (dd, 1H) ), 8.00 (dd, 1H), 7.09 (t, 1H), 6.70 (q, 1H), 3.77～3.68 (m, 1H), 3.58～3.49 (m, 1H), 2.06 (d, 3H), 1.07 ( t, 3H). Compound No. A-35: ¹ H-NMR (CDCl ₃ , δ ppm) 8.97 (d, 1H), 8.60 (d, 1H), 8.48 (d, 1H), 8.32 (s, 1H), 8.24 (d, 2H), 8.15 (dd, 1H), 8.04 (s, 1H), 6.59～6.53 (m, 1H), 1.80 (d, 3H). Compound No. A-40: ¹ H-NMR (CDCl ₃ , δ ppm) 8.60 (s, 1H), 8.24 (dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75～3.65 (m, 1H), 3.56～3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). Compound No. A-52: ¹ H-NMR (CDCl ₃ , δ ppm) 8.44 (s, 1H), 8.24 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.01 (s, 1H), 7.78 (s, 1H), 7.61～7.62 (m, 1H), 6.79 (q, 1H), 3.43 (s, 3H), 1.93 (d, 3H). Compound No. A-57: ¹ H-NMR (CDCl ₃ , δ ppm) 8.60 (s, 1H), 8.24 ( dd, 2H), 8.08 (s, 1H), 8.04 (d, 1H), 7.99 (d, 1H), 7.07 (t, 1H), 6.68 (qd, 1H), 3.75～3.65 (m, 1H), 3.56 ~3.48 (m, 1H), 2.04 (d, 3H), 1.06 (t, 3H). Compound No. A-58: ¹ H-NMR (CDCl ₃ , δ ppm) 8.45 (s, 1H), 8.30 (dd, 1H), 8.13 (dd, 1H), 8.09 (dd, 1H), 8.02 (d, 1H), 8.01 (s, 1H), 8.00 (d, 1H), 6.79 ( q, 1H), 3.44 (s, 3H), 1.93 (d, 3H). Compound No. A-63: ¹ H-NMR (DMSO-d6, δ ppm) 8.56 (s, 1H), 8.47 (dd, 1H) , 8.29 (s, 1H) , 8.27 (d, 1H), 8.21 (d, 1H), 8.17 (d, 1H), 7.99 (d, 1H), 6.80 (q, 1H), 5.41～5.50 (m, 1H) ), 5.28～5.35 (m, 1H), 4.27～4.32 (m, 1H), 4.17 (dd, 1H), 1.85 (d, 3H), 1.50 (d, 3H).

[Biological test] The following test examples show that the compound of the present invention is effective as an active ingredient of a pest control agent. "Part" is the quality standard.

(Preparation of test emulsion) 5 parts of the compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkyl aryl ether were mixed and dissolved to obtain an emulsion (I) with 5 mass % of active ingredients.

(Preparation of control emulsion) 93.6 parts of dimethylformamides and 1.4 parts of polyoxyethylene alkyl aryl ethers were mixed and dissolved to obtain Emulsion (II).

(1) Efficacy test against armyworm (Mythimna separata) (1) 0.8 g of commercially available artificial feed (insect-based LFS (insecta LFS), manufactured by Nippon Agricultural Products Co., Ltd.) was thoroughly mixed with 1 μl of Emulsion (I), and placed in plastic test containers (1.4 ml capacity) for each treatment area. Enter 0.2 g as the test feed. Two armyworm second-instar larvae were inoculated in each treatment area, and sealed with plastic lids. It was placed in a constant temperature room at 25°C, and the insecticidal rate and food intake were studied on the 5th day. The test was repeated twice. Insecticidal rate (%) = (number of dead insects/number of tested insects) × 100 In addition, the test was carried out in parallel under the same conditions as described above, except that the emulsion (I) was replaced by the emulsion (II).

For the compound of compound No. A-1, the efficacy test (1) against armyworm was performed. The compound of A-1 has an insecticidal rate of 100% and is effective. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-12, A-13, A-16, A-17, A-18, A-19, A-25, A-26, A-28, A-29, A-30, A-32, A-33, A-34, A-35, A-36, A-39, A-41, A-42, A-43, A- 44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, A-54, A-55, A-56, The compounds of A-57 and A-58 were tested for their efficacy against armyworms (1). The insecticidal rate of any compound was 100% and effective.

(2) Efficacy test against armyworms (2) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The corn leaves were dipped in the dilution for 30 seconds. The corn leaf was put into a petri dish, and 5 armyworm second instar larvae were placed. During the test period, the petri dish was placed in a constant temperature room with a temperature of 25° C. and a humidity of 60%. When 6 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.

For the compounds of compound numbers A-2 and A-3, the efficacy test (2) against armyworm was carried out. For armyworms, either compound showed an insecticidal rate of over 80%. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-14, A-16, A-17, A-18, A-19, A-20, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-38, A-39, A- 41, A-42, A-43, A-44, A-48, A-50, A-52, A-55, A-56, A-57, A-58, A-60, A-61, The compounds of A-62 and A-63 were tested for their efficacy against armyworms (2). The insecticidal rate of any compound was 80% and effective.

(3) Efficacy test against diamondback moth (Plutella xylostella) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The cabbage leaves were dipped in the dilution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five second-instar larvae of diamondback moth were put there. During the test period, the petri dish was placed in a constant temperature room with a temperature of 25° C. and a humidity of 60%. When 3 days have elapsed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.

For the compounds of compound numbers A-2 and A-3, efficacy tests against diamondback moth were conducted. For the diamondback moth, either compound showed an insecticidal rate of over 80%. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-9, A-10, A-11, A-14, A-16, A-17, A-18, A-19, A-20, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A-36, A-38, A-39, A- 41, the compounds of A-44, A-49, A-50, A-52, A-55, A-57, A-58, A-60, A-61, A-62 and A-63 were compared Efficacy test of diamondback moth. For the diamondback moth, either compound showed an insecticidal rate of over 80%.

(4) Efficacy test against German cockroaches (Blattella germanica) Using a microsyringe, 10 μg of the compound of the present invention was directly injected into the adult female German cockroach. Next, three adult female German cockroaches were placed in a plastic cup, and a commercially available artificial feed was placed as a bait. During the test period, the cup was placed in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 2 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.

For the compounds of compound numbers A-1, A-2, A-3 and A-4, the injection efficacy test against German cockroach was carried out. For German cockroaches, either compound showed a 100% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%. Similarly, for compound numbers A-7, A-9, A-10, A-11, A-12, A-13, A-14, A-17, A-18, A-21, A-22, A-23, A-24, A-25, A-26, A-28, A-29, A-30, A-31, A-32, A-33, A-34, A-35, A- 36, A-38, A-39, A-44, A-45, A-46, A-47, A-48, A-49, A-50, A-51, A-52, A-53, The compounds of A-54, A-55, A-56, A-57, A-58 and A-59 were tested for injection efficacy against German cockroaches. For German cockroaches, either compound showed a 100 percent insecticidal rate.

(5) Efficacy test against Spodoptera litura Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The cabbage leaves were dipped in the dilution for 30 seconds. The cabbage leaves were air-dried and placed in a petri dish, and five second-instar larvae of Spodoptera litura were put there. The petri dish was placed in a constant temperature room with a temperature of 25°C and a humidity of 60%. When 6 days have passed after the release, the determination of life and death is carried out, and the insecticidal rate is calculated. The test was repeated twice.

For compound numbers A-9, A-17, A-18, A-19, A-20, A-26, A-28, A-29, A-30, A-31, A-32, A-33 , A-34, A-35, A-36, A-38, A-39, A-41, A-42, A-43, A-44, A-50, A-52, A-57, A -58, A-60, A-61, A-62 and A-63 compounds were tested for their efficacy against Spodoptera litura. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.

(6) Efficacy test on cotton aphid (Aphis gossypii) Sow cucumbers in 3-inch pots. Cotton aphid female adults were placed on cucumbers 10 days after germination. The next day, the first instar larvae produced were left, and the female adults were removed. The emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm by mass. This dilution is spread over the cucumbers. Then, the cucumbers were placed in a constant temperature room with a temperature of 25°C and a humidity of 60%, and after 5 days, the life and death of cotton aphids were studied, and the insecticidal rate was obtained.

For compound numbers A-9, A-14, A-17, A-19, A-25, A-28, A-29, A-30, A-38, A-39, A-41, A-50 , A-55 and A-57 compounds were tested for efficacy against cotton aphid. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.

(7) Efficacy test on Thrips palmi Eight adults of Thrips palmi were inoculated on cucumber seedlings. Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The dilution was spread on cucumber seedlings and air-dried. The number of parasitic larvae was counted when 7 days had passed after dispersal. The efficacy of the compounds was evaluated by the control rates shown below. Control rate (%)={1-(Nt)/(Nc)}×100 Nt: the number of parasites in the scattered treatment area Nc: the number of parasites in the untreated area

For the compounds of compound numbers A-17, A-19, A-26, A-28, A-29, A-30, A-31, A-39, A-41, A-50 and A-57, the Efficacy test on Thrips palmi. Either compound showed a control rate of over 80%. On the other hand, the control rate of Emulsion (II) was 0%.

(8) Efficacy test against brown planthopper (Nilaparvata lugens) Emulsion (I) was diluted with water so that the density|concentration of this invention compound might become 125 mass ppm. The rice seedlings were immersed in the diluent for 30 seconds, and after air-drying, they were put into a plastic box, and 5 second-instar larvae of N. lugens were placed. It was placed in a constant temperature room with a temperature of 25°C and a humidity of 65%, and 10 days after the inoculation, the dead or alive was judged, and the insecticidal rate was calculated by the following formula. The test was repeated twice. Insecticidal rate (%) = (number of dead insects/number of tested insects) × 100

For the compounds of compound numbers A-26, A-29, A-30, A-39 and A-57, the efficacy test against N. lugens was carried out. Either compound showed more than 80% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.

(9) Efficacy test against housefly The compound of the present invention was diluted with acetone and added dropwise to 1 g of sugar cubes so as to be 100 mass ppm. Put the sugar cube into a plastic cup, put 10 adult female houseflies, and cover it. It was stored at 25 degreeC, and 24 hours after it was put in, the life-and-death determination was performed, and the insecticidal rate was calculated by the following formula. The test was repeated twice.

For the compounds of compound numbers A-17, A-18, A-19, A-29 and A-30, the efficacy test on female adult housefly was carried out. Either compound showed 100% insecticidal rate. On the other hand, the insecticidal rate of Emulsion (II) was 0%.

The compounds randomly selected from the compounds of the present invention have the above-mentioned effects, so it can be understood that the compounds of the present invention, including those not completely shown in the examples, have the functions of controlling pests, killing acarids, especially killing compounds with insect effects. [Industrial Availability]

The azinylazole compound of the present invention has the ability to control harmful organisms that are problematic in terms of crops or sanitation. The control agent containing the azinylazole compound of the present invention can effectively control harmful organisms, especially agricultural pests and mites, at a lower concentration, and further, can effectively control external parasites and internal parasites that sometimes harm humans and animals.

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Claims (6)

A compound or its salt represented by formula (I);

In formula (I), X represents halogen, substituted or unsubstituted C1-6 alkyl, hydroxy, substituted or unsubstituted C1-6 alkoxy, substituted or unsubstituted C1-6 Alkylthio, substituted or unsubstituted C1-6 alkylsulfinyl, substituted or unsubstituted C1-6 alkylsulfonyl, substituted or unsubstituted C3-6 cycloalkyl , substituted or unsubstituted C3-6 cycloalkoxy, substituted or unsubstituted C3-6 cycloalkylthio, substituted or unsubstituted C3-6 cycloalkylsulfinyl, substituted or unsubstituted C3-6 cycloalkylsulfonyl, nitro or cyano group; or, X represents substituted or unsubstituted C2-6 alkynyl; n represents the number of X and is 0-5 Any integer, when n is 2 or more, X may be the same or different from each other, R ¹ represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group, R ² represents a hydrogen atom, or a substituted or unsubstituted C1-6 alkyl group Unsubstituted C1-6 alkyl, R ³ represents a hydrogen atom, substituted or unsubstituted C1-6 alkyl, substituted or unsubstituted C1-6 alkylcarbonyl, or substituted or unsubstituted C1-6 alkoxycarbonyl group, Y ¹ represents a nitrogen atom or ^a group represented by ^{CR a, Y 2} represents a nitrogen atom or ^a group represented by ^{CR a, R a} independently represents a hydrogen atom, a halogen group, or a substituted group or an unsubstituted C1-6 alkyl group, Q represents a substituted or unsubstituted 6-membered heteroaryl group. The compound or salt thereof according to claim 1, wherein Q is a substituted or unsubstituted pyridyl group, or a substituted or unsubstituted pyrimidinyl group. A pest control agent containing at least one selected from the group consisting of the compound described in claim 1 or claim 2 and a salt thereof as an active ingredient. An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 or claim 2 and a salt thereof as an active ingredient. An ectoparasite control agent containing at least one selected from the group consisting of the compound according to claim 1 or claim 2 and a salt thereof as an active ingredient. An internal parasite control or expelling agent containing at least one selected from the group consisting of the compound according to claim 1 or claim 2 and a salt thereof as an active ingredient.