TWI732809B - Diarylazole compound and harmful organism control agent - Google Patents

Abstract

The present invention provides a compound represented by formula (I) (in the formula, B¹ and B⁴ each independently represents a carbon atom, nitrogen atom or the like; B² and B³ each independently represents a nitrogen atom or the like; R⁴ represents a hydrogen atom, halogeno group or the like; Ar represents an unsubstituted or substituted C6-10 aryl group or the like; Q represents a substituted phenyl group, substituted pyridyl group or the like) or salt thereof, and a harmful organism control agent including the compound or salt thereof.

Description

Diarylazole compounds and pest control agents

The invention relates to a diarylazole compound and a pest control agent. In more detail, the present invention relates to a diarylazole compound that has excellent insecticidal activity and/or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially, and pest control containing it as an effective ingredient Agent.

Various compounds with insecticidal and acaricidal activities have been proposed. In order to use this compound as a pesticide, it is required that it is not only highly effective, but also difficult to produce resistance; it does not cause phytotoxicity to plants or soil pollution; and has low toxicity to livestock or fish.

In addition, Patent Document 1 discloses a compound represented by formula (A). According to Patent Document 1, the compound can be used to treat diabetes, hyperglycemia, obesity, insulin resistance, arteriosclerosis, dyslipidemia, hypertension, and metabolic syndrome.

Patent Document 2 discloses a compound represented by formula (B) and the like.

Patent Document 3 discloses a compound represented by formula (C). Patent Document 3 has a description that the compound has insecticidal and acaricidal activities.

[Patent Document 1] Japanese Special Publication No. 2007-530690

[Patent Document 2] WO2015/144826 A1

[Patent Document 3] WO2010/136145 A1

The subject of the present invention is to provide a diarylazole compound which is excellent in pest control activity, especially insecticidal activity and/or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially; and to provide a compound containing it as effective Ingredients of pest control agent. Furthermore, it is to provide an external parasite control agent, or internal parasite control or repellent containing it as an active ingredient.

In order to solve the above-mentioned problems, after diligent research, the present invention including the following aspects has been completed.

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

[In formula (I), B ¹ and B ⁴ each independently represent a carbon atom or a nitrogen atom. B ² and B ³ each independently represent a nitrogen atom or CR ⁵ . Here, when B ¹ is a carbon atom, B ² is a nitrogen atom or CR ⁵ , and B ³ and B ⁴ are nitrogen atoms. When B ¹ is a nitrogen atom, B ² is a nitrogen atom, B ³ is a nitrogen atom or CR ⁵ , and B ⁴ is a carbon atom.

R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogeno group, a cyano group, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, Unsubstituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or substituted C1~6 alkoxy, methanoyl, unsubstituted or substituted C1~6 alkylcarbonyl, Unsubstituted or substituted C1~6 alkoxycarbonyl, unsubstituted or substituted C1~6 alkylthio group, unsubstituted or substituted C1~6 alkylene Sulfonyl, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C1-6 alkylsulfonyloxy group, or unsubstituted or substituted amino group , -S(=O)(=NR ^a )-R ^b represents the base. Here, R ^a and R ^b each independently represent an unsubstituted or substituted C1-6 alkyl group.

Ar represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group.

Q is a base represented by formula (Q-1) or (Q-2).

In formulas (Q-1) and (Q-2), * represents the bonding position.

R ¹ represents unsubstituted or substituted C1-6 alkylthio, unsubstituted or substituted C1-6 alkylsulfinyl, unsubstituted or substituted C1-6 alkyl Sulfonyl, unsubstituted or substituted C1-6 alkylsulfonyloxy or -S(=O)(=NR ^a )-R ^b represents a group. Here, R ^a and R ^b each independently represent an unsubstituted or substituted C1-6 alkyl group.

In formula (Q-1), A ¹ and A ² each independently represent a carbon atom or a nitrogen atom. Among them, A ¹ and A ^{2 are} not nitrogen atoms at the same time.

X represents unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkynyl, hydroxyl, unsubstituted or Substituted C1~6 alkoxy, methanoyl, unsubstituted or substituted C1~6 alkylcarbonyl, unsubstituted or substituted C1~6 alkoxycarbonyl, mercapto, unsubstituted Substituted or substituted C1~6 alkylsulfinyl group, unsubstituted or substituted C1~6 alkylsulfinyl group, unsubstituted or substituted C1~6 alkylsulfinyl group, unsubstituted C1~6 alkylsulfinyl group, unsubstituted or substituted C1~6 alkylsulfinyl group Substituted or substituted aminocarbonyl, unsubstituted or substituted C3~8 cycloalkyl, unsubstituted or substituted C6~10 aryl, unsubstituted or substituted C6~ 10 aryloxy group, unsubstituted or substituted 3-6 membered heterocyclyl group, unsubstituted or substituted amine group, halogen group, cyano group or nitro group.

n represents the number of X, and is any integer from 0 to 4. When n is 2 or more, X may be the same or different from each other.

In the formula (Q-2), A ³ represents a carbon atom or a nitrogen atom.

R ² and R ³ each independently represent a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2~ 6 alkynyl, hydroxyl, unsubstituted or substituted C1-6 alkoxy, methanoyl, unsubstituted or substituted C1-6 alkylcarbonyl, unsubstituted or substituted C1~ 6Alkoxycarbonyl, mercapto, unsubstituted or substituted C1-6 alkylthio, unsubstituted or substituted C1-6 alkylsulfinyl, unsubstituted or substituted C1~6 alkylsulfonyl, unsubstituted or substituted aminocarbonyl, unsubstituted or substituted C3~8 cycloalkyl, unsubstituted or substituted C6~10 aryl, Unsubstituted or substituted C6-10 aryloxy group, unsubstituted or substituted 3--6 membered heterocyclic group, unsubstituted or substituted amine group, halogen group, cyano group or nitro group . Wherein, when R ³ is a hydrogen atom, R ² is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclic group.

Wherein, when Ar is an unsubstituted or substituted 5-membered heteroaryl group, Q is a group represented by formula (Q-1); where Ar is an unsubstituted or substituted C6-10 aryl group , Or an unsubstituted or substituted 6-membered heteroaryl group, and when R ⁴ is an unsubstituted or substituted amine group, Q is a group represented by formula (Q-1); when Ar is a non- When a substituted or substituted C6-10 aryl group or an unsubstituted or substituted 6-membered heteroaryl group, and R ⁴ is a substituent other than an unsubstituted or substituted amino group, Q is the base represented by formula (Q-2). ]

[2] A pest control agent containing at least one selected from the group consisting of the compounds described in [1] above and these salts as an active ingredient.

[3] An insecticide or acaricide containing at least one selected from the group consisting of the compound described in [1] above and these salts as an active ingredient.

[4] An ectoparasite control agent containing at least one selected from the group consisting of the compound described in [1] above and these salts as an active ingredient.

[5] An internal parasite control or repellent containing at least one selected from the group consisting of the compounds described in [1] above and these salts as an active ingredient.

The diarylazole compound of the present invention can prevent harmful organisms that are a problem in crops or hygiene. In particular, it can effectively control various agricultural pests and mites at a lower concentration. Furthermore, external parasites and internal parasites that harm humans and animals can be effectively prevented.

[Diarylazole Compound]

The diarylazole compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt of compound (I).

First of all, in the present invention, the term "unsubstituted" means only the base that becomes the mother nucleus. When it is not described together with "substituent" but 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 "substituent" means that any hydrogen atom that becomes the base of the parent nucleus is replaced with a group whose structure is the same as or different from that of the parent nucleus. Therefore, the "substituent" is bound to the base that becomes the nucleus 之Other bases. The number of substituents may be one or two or more. Two or more substituents may be the same or different.

Terms such as "C1~6" indicate that the number of carbon atoms that form the base of the parent nucleus is 1 to 6, etc. The number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The "substituent" is not particularly limited as long as it is chemically acceptable and has the effect of the present invention. Hereinafter, examples of groups that can become "substituents" are illustrated.

C1~6 alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-propyl, secondary propyl, isobutyl, tertiary butyl, n-pentyl, n-hexyl, etc.; vinyl, 1- Propyl, 2-propenyl (allyl), 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl C2~6 alkenyl groups; ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl C2~6 alkynyl groups; C3~8 cycloalkyl groups such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cubanyl group; C6~10 aryl groups such as phenyl and naphthyl groups; benzyl C6~10 aryl, C1~6 alkyl; 3~6 membered heterocyclic group; 3~6 membered heterocyclic group C1~6 alkyl; hydroxy; methoxy, ethoxy, n-propyl C1~6 alkoxy groups such as oxy, isopropoxy, n-butoxy, secondary butoxy, isobutoxy, tertiary butoxy, etc.; C2-6 alkenyloxy such as vinyloxy, allyloxy, propyleneoxy, butenoxy; C2-6alkynoxy such as ethynyloxy and propargyloxy; C6 such as phenoxy and naphthyloxy ~10 aryloxy; C6~10 aryl C1~6 alkoxy such as benzyloxy and phenethoxy; 5~6 member heteroaryloxy such as thiazolyloxy and pyridyloxy; thiazolylmethoxy, 5- to 6-membered heteroaryl C1-6 alkoxy such as pyridylmethoxy; formyl; C1-6 alkylcarbonyl such as acetyl and propionyl; formyloxy; acetoxy, propyl C1~6 alkylcarbonyloxy groups such as acyloxy; C6~10 arylcarbonyl groups such as benzyloxy; methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, n-butoxy C1~6 alkoxycarbonyl groups such as carbonyl, tertiary butoxycarbonyl; methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, isopropoxycarbonyloxy, n-but C1~6 alkoxycarbonyloxy groups such as oxycarbonyloxy and tertiary butoxycarbonyloxy; carboxy; halogen groups such as fluoro, chloro, bromo, and iodo; chloromethyl, chloroethyl, C1~6 halogenated alkyl groups such as trifluoromethyl, 1,2-dichloro-n-propyl, 1-fluoro-n-butyl, perfluoro-n-pentyl; 2-chloro-1-propenyl, 2-fluoro-1- C2~6 halogenated alkenyl groups such as butenyl; C2~6 halogenated alkynyl groups such as 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl, etc. ； C1~6 halogenated alkoxy groups such as trifluoromethoxy, 2-chloro-n-propoxy, 2,3-dichlorobutoxy, etc.; 2-chloropropenoxy, 3-bromobutenoxy, etc. C2~6 Halogenated alkenyloxy groups; C1~6 halogenated alkyl carbonyl groups such as chloroacetinyl, trifluoroacetinyl, and trichloroacetinyl; amino groups; methylamino groups, dimethylamino groups, diethylamino groups, etc. C1~6 alkyl substituted amino groups; C6~10 arylamino groups such as anilino and naphthylamino groups; C6~10 aryl groups such as benzylamino groups and phenethylamino groups; Amino; Acetylamino, propionylamino, butyrylamino, isopropylcarbonylamino and other C1~6 alkylcarbonylamino groups; methoxycarbonylamino, ethoxycarbonylamino, Mono-C1~6 alkoxycarbonylamino groups such as n-propoxycarbonylamino and isopropoxycarbonylamino; di(methoxycarbonyl)amino, di(ethoxycarbonyl)amino, di(normal) Propoxycarbonyl)amino group, di(isopropoxycarbonyl)amino group, di(n-butoxycarbonyl)amino group, di(tertiary butoxycarbonyl)amino group and other di-C1~6 alkoxycarbonyl groups Amino; aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylaminocarbonyl and other unsubstituted or substituted aminocarbonyl; iminomethyl , (1-imino) ethyl, (1-imino)-n-propyl and other imino C1~6 alkyl; N-hydroxy-iminomethyl, (1-(N-hydroxy) -Imino) ethyl, (1-(N-hydroxy)-imino)propyl, N-methoxy-iminomethyl, (1-(N-methoxy)-imino ) Ethyl and other unsubstituted or substituted N-hydroxyimino C1~6 alkyl groups; Aminocarbonyloxy; ethylaminocarbonyloxy, dimethylaminocarbonyloxy and other C1-6 alkyl substituted aminocarbonyloxy; mercapto; methylthio, ethylthio, n-propylthio, Isopropylthio, n-butylthio, isobutylthio, secondary butylthio, tertiary butylthio and other C1~6 alkylthio groups; trifluoromethylthio, 2,2,2-trifluoroethane C1~6 haloalkylthio groups such as thio; C6~10 arylthio groups such as phenylthio and naphthylthio; 5-6 membered heteroarylthio groups such as thiazolylthio and pyridylthio; methylsulfinylthio , Ethylsulfinyl, tertiary butylsulfinyl, etc. C1~6 alkylsulfinyl; trifluoromethylsulfinyl, 2,2,2-trifluoroethylsulfinyl C1~6 halogenated alkylsulfinyl groups; C6~10 arylsulfinyl groups such as phenylsulfinyl groups; 5~6 membered heteroaryl groups such as thiazolylsulfinyl groups and pyridylsulfinyl groups Sulfinyl; methylsulfonyl, ethylsulfonyl, tertiary butylsulfonyl and other C1~6 alkylsulfonyl groups; trifluoromethylsulfonyl, 2,2,2-trifluoro C1~6 halogenated alkylsulfonyl groups such as ethylsulfonyl; C6~10 arylsulfonyl groups such as phenylsulfonyl; 5~6 membered heteroaryl groups such as thiazolylsulfonyl and pyridylsulfonyl Sulfonyl; methylsulfonyloxy, ethylsulfonyloxy, tertiary butylsulfonyloxy and other C1~6 alkylsulfonyloxy; trifluoromethylsulfonyloxy, 2,2, 2-Trifluoroethylsulfonyloxy and other C1~6 halogenated alkylsulfonyloxy groups; Trimethylsilyl, triethylsilyl, tertiary butyldimethylsilyl and other tri-C1~6 alkyl substituted silyl groups; triphenylsilyl and other tri-C6~10 aryl substituted silyl groups; cyano ; Nitro; In addition, for these "substituents", any hydrogen atom in the substituents may also be substituted by groups of different structures. Examples of the "substituent" in this case include: C1-6 alkyl, C1-6 halogenated alkyl, C1-6 alkoxy, C1-6 halogenated alkoxy, halogen, cyano, nitro, etc. .

In addition, the aforementioned "3- to 6-membered heterocyclic group" refers to those containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as the constituent atoms of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. As long as at least one ring of the polycyclic heterocyclic group is a heterocyclic ring, the remaining rings may be any of a saturated alicyclic ring, an unsaturated aliphatic ring, or an aromatic ring. 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.

基、

啉基、二氧雜環戊基(dioxolanyl group)、二氧雜環己基(dioxanyl group)等。 Examples of saturated heterocyclic groups with 3 to 6 members include: aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, tetrahydrothiazolyl group, piperidinyl group, piperidine group

base,

Linyl, dioxolanyl group, dioxanyl group, etc.

唑基、異

唑基、噻唑基、異噻唑基、三唑基、

二唑基(oxadiazolyl group)、噻二唑基(thiadiazolyl group)、四唑基等。作為6員雜芳基，可列舉：吡啶基、吡

基、嘧啶基、嗒

基、三

基等。 Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl,

Azolyl, iso

Azolyl, thiazolyl, isothiazolyl, triazolyl,

Oxadiazolyl group, thiadiazolyl group, tetrazolyl group, etc. Examples of 6-membered heteroaryl groups include: pyridyl, pyridine

Base, pyrimidinyl, ta

Base, three

Base and so on.

[B ¹ , B ² , B ³ , B ⁴ ]

In formula (I), B ¹ and B ⁴ each independently represent a carbon atom or a nitrogen atom, and B ² and B ³ each independently represent a nitrogen atom or CR ⁵ . Here, when B ¹ is a carbon atom, B ² is a nitrogen atom or CR ⁵ , and B ³ and B ⁴ are nitrogen atoms. When B ¹ is a nitrogen atom, B ² is a nitrogen atom, B ³ is a nitrogen atom or CR ⁵ , and B ⁴ is a carbon atom. That is, the compound represented by formula (I) is a compound represented by formula (I-1) to formula (I-4).

In formula (I-1) to formula (I-4), Q, R ⁴ , R ⁵ and Ar have the same meanings as those in formula (I). Among these, the compound represented by formula (I-1) is preferred.

[R ⁴ , R ⁵ ]

In formula (I), R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogen group, a cyano group, an unsubstituted or substituted C1-6 alkyl group, and an unsubstituted or substituted C2-6 alkene Group, unsubstituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or substituted C1~6 alkoxy, methanoyl, unsubstituted or substituted C1~6 alkyl Carbonyl, unsubstituted or substituted C1-6 alkoxycarbonyl, unsubstituted or substituted C1-6 alkylthio, unsubstituted or substituted C1-6 alkylsulfinyl Group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C1-6 alkylsulfonyloxy group, unsubstituted or substituted amino group or -S (=O)(=NR ^a )-R ^b represents the base. Here, R ^a and R ^b each independently represent an unsubstituted or substituted C1-6 alkyl group.

Examples of the "halogen group" in R ⁴ and R ⁵ include a fluoro group, a chloro group, a bromo group, and an iodo group.

The "C1-6 alkyl group" in R ⁴ and R ⁵ may be a straight chain, and if the carbon number is 3 or more, it may be a branched chain. Examples of the alkyl group include methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl, isobutyl, secondary butyl, tertiary butyl, isopentyl, Neopentyl, 2-methylbutyl, 2,2-dimethylpropyl, isohexyl, etc.

Specific examples of the "substituted C1-6 alkyl group" include fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, dibromomethyl, and trifluoromethyl , Trichloromethyl, tribromomethyl, 1-chloroethyl, 2,2,2-trifluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 4-fluorobutyl, 4-chlorobutyl, 3,3,3-trifluoropropyl, 2,2,2-trifluoro-1-trifluoromethylethyl, perfluorohexyl, perchlorohexyl, 2,4,6-tri C1~6 halogenated alkyl groups such as chlorohexyl; methoxy methyl, ethoxy methyl, methoxy ethyl, ethoxy ethyl, methoxy n-propyl, n-propoxy methyl, isopropyl C1~6 alkoxy C1~6 alkyl such as oxyethyl, secondary butoxymethyl, tertiary butoxyethyl, etc.; C6~10 aryl C1~6 alkyl such as benzyl, phenethyl, etc. ; Cyclopropylmethyl, 2-cyclopropylethyl, cyclopentylmethyl, 2-cyclohexylethyl, 2-cyclooctylethyl and other C3~8 cycloalkyl, C1~6 alkyl, etc.

Examples of "C2-6 alkenyl" in R ⁴ and R ⁵ include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2 -Butenyl, 2-methyl-2-butenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, etc.

Specific examples of "substituent C2-6 alkenyl" include: 2-chloro-1-propenyl, 2-fluoro-1-butenyl and other C2-6 haloalkenyl groups; 2-n-butoxy C1~6 alkoxy, C2~6 alkenyl, such as group-vinyl, 1-ethoxy-vinyl, etc.

Examples of "C2-6 alkynyl" in R ⁴ and R ⁵ include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, and 3-butynyl Group, 1-methyl-2-propynyl, 2-methyl-3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1- Methyl-2-butynyl, 2-methyl-3-pentynyl, 1-hexynyl, 1,1-dimethyl-2-butynyl, etc.

Specific examples of "substituent C2-6 alkynyl" include 4,4-dichloro-1-butynyl, 4-fluoro-1-pentynyl, 5-bromo-2-pentynyl C2~6 halogenated alkynyl groups, etc.

Examples of "C1~6 alkoxy" in R ⁴ and R ⁵ include: methoxy, ethoxy, n-propoxy, n-butoxy, n-pentoxy, n-hexoxy, and isopropoxy Group, isobutoxy, secondary butoxy, tertiary butoxy, isohexoxy, etc.

Specific examples of the "substituent C1-6 alkoxy group" include: chloromethoxy, dichloromethoxy, difluoromethoxy, trichloromethoxy, trifluoromethoxy, 1 -Fluoroethoxy, 1,1-difluoroethoxy, 2,2,2-trifluoroethoxy, pentafluoroethoxy, 2,2,3,4,4,4-hexafluoro-butyl C1~6 halogenated alkoxy such as oxy; C1~6 alkoxy such as methoxymethoxy and methoxyethoxy; C1~6 alkoxy; C6~10 aryl C1~6 alkoxy such as benzyloxy and phenethoxy; C3~8 cycloalkyl C1~6 alkoxy such as cyclopropylmethoxy, etc.

Examples of the "C1-6 alkylcarbonyl group" in R ⁴ and R ^{5 include acetyl and propyl.}

Specific examples of the "substituent C1-6 alkylcarbonyl group" include C1-6 halogenated alkylcarbonyl groups such as chloroacetoxy, trifluoroacetoxy, and trichloroacetoxy.

Examples of the "C1~6 alkoxycarbonyl group" in R ⁴ and R ⁵ include: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, isopropoxycarbonyl, tertiary butoxycarbonyl, etc. . Specific examples of "substituent C1-6 alkoxycarbonyl group" include: fluoromethoxycarbonyl, chloromethoxycarbonyl, bromomethoxycarbonyl, difluoromethoxycarbonyl, and dichloromethoxycarbonyl Carbonyl carbonyl, dibromomethoxycarbonyl, trifluoromethoxycarbonyl, trichloromethoxycarbonyl, tribromomethoxycarbonyl, 2,2,2-trifluoroethoxycarbonyl, etc. C1~6 halogenated alkoxy Carbonyl; Cyclopropylmethoxycarbonyl, cyclobutylmethoxycarbonyl, cyclopentylmethoxycarbonyl, cyclohexylmethoxycarbonyl, 2-cyclopropylethoxycarbonyl, etc. C3~8 cycloalkyl C1~ 6Alkoxycarbonyl and so on.

Examples of the "C1-6 alkylthio group" in R ⁴ and R ⁵ include methylthio, ethylthio, n-propylthio, n-butylthio, n-pentylthio, n-hexylthio, isopropyl Sulfuryl, isobutylsulfanyl, etc.

Specific examples of the "substituent C1-6 alkylthio group" include C1-6 halogenated alkylthio groups such as trifluoromethylthio and 2,2,2-trifluoroethylthio.

Examples of the "C1-6 alkylsulfinyl group" in R ⁴ and R ⁵ include methylsulfinyl, ethylsulfinyl, tertiary butylsulfinyl, and the like.

As a specific example of "substituent C1~6 alkylsulfinyl group", one can cite: trifluoro C1~6 halogenated alkylsulfinyl groups such as methylsulfinyl and 2,2,2-trifluoroethylsulfinyl.

Examples of the "C1-6 alkylsulfonyl" in R ⁴ and R ⁵ include methylsulfonyl, ethylsulfonyl, and tertiary butylsulfonyl.

Specific examples of "substituent C1-6 alkylsulfonyl" include C1-6 halogenated alkyl groups such as trifluoromethylsulfonyl and 2,2,2-trifluoroethylsulfonyl Sulfonyl.

Examples of the "C1-6 alkylsulfonyloxy group" in R ⁴ and R ⁵ include methylsulfonyloxy group, ethylsulfonyloxy group, and tertiary butylsulfonyloxy group.

Specific examples of "substituent C1-6 alkylsulfonyloxy group" include trifluoromethylsulfonyloxy group, 2,2,2-trifluoroethylsulfonyloxy group, etc. C1-6 Halogenated alkylsulfonyloxy.

As the "C1~6 alkyl group", "C2~6 alkenyl group", "C2~6 alkynyl group", "C1~6 alkoxy group", "C1~6 alkylcarbonyl group" in ^{R 4} and R ⁵ "C1~6 Alkoxycarbonyl", "C1~6 Alkylthio", "C1~6 Alkylsulfinyl", "C1~6 Alkylsulfonyl" and "C1~6 Alkylsulfonyl" Preferable substituents on the "oxy" group include: C1-6 alkoxy, halogen, cyano, C3-8 cycloalkyl, C6-10 aryl, 3-6 membered heterocyclic group, and the like.

Examples of the substituent in the "amino group having a substituent" in R ⁴ include a C1-6 alkyl group, a C1-6 alkoxy group, and a C1-6 alkoxycarbonyl group.

Examples of the "amino group having a substituent" in R ⁵ include C1-6 alkyl substituted amino groups such as methylamino, n-butylamino, dimethylamino, and diethylamino; Single C1~6 alkoxycarbonylamino groups such as oxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, isopropoxycarbonylamino group, tertiary butoxyaminocarbonylamino group, etc. ; Dimethoxycarbonylamino group, diethoxycarbonylamino group, diisopropoxycarbonylamino group, di-n-propoxycarbonylamino group, two tertiary butoxyaminocarbonylamino group and other two C1~ 6 Alkoxycarbonylamino group and the like.

As the formula: -S(=O)(=NR ^a )-R ^{b in} the group represented by R ^a and ^{the "C1-6 alkyl group" in R b} , and groups with substituents on these groups, examples include These are the same as exemplified in R ⁴ and R ^{5 above.}

As R ⁴ , a hydrogen atom, an unsubstituted or substituted amine group, a C1-6 alkyl group, a halogen group, and a cyano group are preferred, and the unsubstituted or substituted group is more preferred (preferably C1~ 6 alkyl, C1~6 alkoxy, 1~6 alkoxycarbonyl) amino group, C1~6 alkyl.

As R ⁵ , a hydrogen atom or a C1-6 alkyl group is preferable, and a hydrogen atom is more preferable.

[Ar]

In formula (I), Ar represents an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group.

The "C6~10 aryl group" in Ar can be any of monocyclic and polycyclic. As long as at least one ring of the polycyclic aryl group is an aromatic ring, the remaining rings may be any of a saturated aliphatic ring, an unsaturated aliphatic ring, or an aromatic ring. Examples of the "C6-10 aryl group" include phenyl, naphthyl, azulenyl, indenyl, dihydroindenyl, tetralinyl group, and the like, and phenyl is preferred.

唑基、異

唑基、噻唑基、異噻唑基、三唑基(詳細為[1,2,3]三唑基或[1,2,4]三唑基)、

二唑基(詳細為[1,2,3]

二唑基、[1,2,4]

二唑基、[1,2,5]

二唑基或[1,3,4]

二唑基)、噻二唑基、四唑基等5員雜芳基；吡啶基、吡

基、嘧啶基、嗒

基、三

基等6員雜芳基等。 Examples of the "5- to 6-membered heteroaryl group" in Ar include: pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl,

Azolyl, iso

Azolyl, thiazolyl, isothiazolyl, triazolyl (detailed as [1,2,3]triazolyl or [1,2,4]triazolyl),

Diazolyl (detailed as [1,2,3]

Diazolyl, [1,2,4]

Diazolyl, [1,2,5]

Diazolyl or [1,3,4]

Diazolyl), thiadiazolyl, tetrazolyl and other 5-membered heteroaryl groups; pyridyl, pyridine

Base, pyrimidinyl, ta

Base, three

Heteroaryl groups such as 6-membered groups.

基，更佳為吡啶基或吡唑基，更佳為吡啶 -3-基或1H-吡唑-1-基。 As the "5- to 6-membered heteroaryl group" in Ar, thienyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl or pyridine are preferred

The group is more preferably pyridyl or pyrazolyl, more preferably pyridin-3-yl or 1H-pyrazol-1-yl.

Examples of the substituents on the "C6~10 aryl group" and "5~6 membered heteroaryl group" in Ar include: unsubstituted or substituted C1~6 alkyl group, unsubstituted or substituted group C2~6 alkenyl, unsubstituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or substituted C1~6 alkoxy, methanoyl, unsubstituted or substituted C1~6 alkylcarbonyl, unsubstituted or substituted C1~6 alkoxycarbonyl, mercapto, unsubstituted or substituted C1~6 alkylthio, unsubstituted or substituted C1 ~6 Alkylsulfinyl, unsubstituted or substituted C1~6 alkylsulfonyl, unsubstituted or substituted C3~8 cycloalkyl, unsubstituted or substituted C6 ~10 aryl groups, unsubstituted or substituted 3-6 membered heterocyclic groups, unsubstituted or substituted pyridyloxy groups, unsubstituted or substituted amine groups, halogen groups, cyano groups, Nitro and so on.

As the "C1~6 alkyl group", "C2~6 alkenyl group", "C2~6 alkyl group", "C2~6 alkenyl group", "C6~10 aryl group" in "Ar" and "5~6 membered heteroaryl group substituents" in the above "Alkynyl", "C1~6 Alkoxy", "C1~6 Alkylcarbonyl", "C1~6 Alkoxycarbonyl", "C1~6 Alkylthio", "C1~6 Alkylsulfinyl""Alkyl","C1~6alkylsulfonyl","amino" and "halogen" and groups having substituents on these groups, such as those exemplified in the above R ⁴ and R ⁵ The same.

As the "C3-8 cycloalkyl group" in the above "Ar in the "C6-10 aryl group" and the "5- to 6-membered heteroaryl group" substituents, examples include: cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, cycloheptyl, etc.

As the "C6-10 aryl group" in the above "Ar "C6~10 aryl group" and "5- to 6-membered heteroaryl group", the same as those exemplified in the above Ar can be cited By.

The above "C6~10 aryl group" and "5~6 member heteroaryl group" in the above The "3- to 6-membered heterocyclic group" in "substitution" contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as the constituent atoms of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. As long as at least one ring of the polycyclic heterocyclic group is a heterocyclic ring, the remaining rings may be any of a saturated alicyclic ring, an unsaturated aliphatic ring, or an aromatic ring. 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.

基、

啉基、二氧雜環戊基(詳細為[1,3]二氧雜環戊基)、二氧雜環己基(詳細為[1,3]二氧雜環己基或[1,4]二氧雜環己基)等。較佳為5~6員飽和雜環基。 Examples of saturated heterocyclic groups with 3 to 6 members include: aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperidine

base,

Alkyl, dioxolane ([1,3]dioxolyl), dioxanyl ([1,3]dioxanyl or [1,4]two Oxanyl) and so on. Preferably, it is a 5-6 membered saturated heterocyclic group.

唑基、異

唑基、噻唑基、異噻唑基、三唑基(詳細為[1,2,3]三唑基或[1,2,4]三唑基)、

二唑基(詳細為[1,2,4]

二唑基或[1,3,4]

二唑基)、噻二唑基、四唑基等。 Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl,

Azolyl, iso

Azolyl, thiazolyl, isothiazolyl, triazolyl (detailed as [1,2,3]triazolyl or [1,2,4]triazolyl),

Diazolyl (detailed as [1,2,4]

Diazolyl or [1,3,4]

Diazolyl), thiadiazolyl, tetrazolyl and the like.

基、嘧啶基、嗒

基、三

基等。 Examples of 6-membered heteroaryl groups include: pyridyl, pyridine

Base, pyrimidinyl, ta

Base, three

Base and so on.

唑啉基、異

唑啉基、噻唑啉基等。 Examples of partially unsaturated 5-membered heterocyclic groups include: pyrrolinyl, imidazolinyl (dihydroimidazolyl), pyrazolinyl,

Oxazoline, iso

Oxazolinyl, thiazolinyl, etc.

Examples of partially unsaturated 6-membered heterocyclic groups include thiopyranyl, 2H-pyridin-1-yl, 4H-pyridin-1-yl, and the like.

As the above-mentioned "C6~10 aryl group in Ar" and "substituent on 5~6 membered heteroaryl group", "C3~8 cycloalkyl group", "C6~10 aryl group", " 3~6 heterocyclic group" substituted groups, include: C 1~6 alkyl, C1~6 halogenated alkyl, hydroxy, C1~6 alkoxy, C1~6 alkoxycarbonyl, C1~6 alkane Alkylthio, C1~6 alkylsulfinyl, C1~6 alkylsulfinyl, amino, C1~6 alkyl substituted amino, halogen, cyano, nitro, etc. Among these, preferred are C1-6 alkyl groups, C1-6 halogenated alkyl groups, hydroxyl groups, C1-6 alkoxy groups, halogen groups, cyano groups, and nitro groups.

As the substituents on "C6~10 aryl" and "5~6 membered heteroaryl" in Ar, C1~6 alkyl, C1~6 haloalkyl, C1~6 alkoxy, C1 are preferred ~6 halogenated alkoxy group, C1~6 alkylthio group, C1~6 halogenated alkylthio group, C1~6 alkylsulfinyl group, C1~6 halogenated alkylsulfinyl group, C1~6 alkyl group Sulfonyl group, C1~6 halogenated alkylsulfonyl group, halogen group or (which can be substituted by halogen group or C1~6 halogenated alkoxy group) 5-6 membered heteroaryl group (preferably pyridyl), more preferably It is a C1~6 alkyl group, a C1~6 halogenated alkyl group, a C1~6 halogenated alkoxy group, a C1~6 halogenated alkylthio group, and a halogen group.

The number of substituents on "C6~10 aryl" and "5~6 membered heteroaryl" in Ar is preferably 0~3, more preferably 0~2, further preferably 1 or 2 Piece.

[Q]

In formula (I), Q is a group represented by formula (Q-1) or (Q-2).

In formulas (Q-1) and (Q-2), * represents the bonding position.

In formulas (Q-1) and (Q-2), R ¹ represents an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group , Unsubstituted or substituted C1~6 alkylsulfonyl group, unsubstituted or substituted C1~6 alkylsulfonyloxy group or -S(=O)(=NR ^a )-R ^b The base of expression. Here, R ^a and R ^b each independently represent an unsubstituted or substituted C1-6 alkyl group.

R ¹ is in the "C1 ~ 6 alkylthio,""alkylsulfinyl C1 ~ 6 acyl", "C1 ~ 6 alkylsulfonyl group", and "C1 ~ 6 alkylsulfonyl group" And the groups having substituents on these groups are the same as those exemplified in the above-mentioned R ⁴ and R ⁵ .

As the formula: -S(=O)(=NR ^a )-R ^{b in} the group represented by R ^a and ^{the "C1-6 alkyl group" in R b} , and groups with substituents on these groups, examples include These are the same as exemplified in R ⁴ and R ^{5 above.}

As R ¹ , a C1-6 alkylsulfinyl group, a C1-6 alkylsulfinyl group, and a C1-6 alkylsulfinyl group are preferable, and a C1-6 alkylsulfinyl group is particularly preferable.

In formula (Q-1), A ¹ and A ² each independently represent a carbon atom or a nitrogen atom. Among them, A ¹ and A ^{2 are} not nitrogen atoms at the same time.

In formula (Q-1), X represents unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkyne Group, hydroxyl, unsubstituted or substituted C1-6 alkoxy, methanoyl, unsubstituted or substituted C1-6 alkylcarbonyl, unsubstituted or substituted C1-6 alkane Oxycarbonyl, mercapto, unsubstituted or substituted C1-6 alkylthio, unsubstituted or substituted C1-6 alkylsulfinyl, unsubstituted or substituted C1~ 6 Alkylsulfonyl group, unsubstituted or substituted amine group, unsubstituted or substituted aminocarbonyl group, unsubstituted or substituted C3~8 cycloalkyl group, unsubstituted or substituted Substituent C6~10 Aryl, unsubstituted or substituted C6-10 aryloxy, unsubstituted or substituted 3-6 membered heterocyclic group, halogen group, cyano group or nitro group.

As "C1~6 alkyl", "C2~6 alkenyl", "C2~6 alkynyl", "C1~6 alkoxy", "C1~6 alkylcarbonyl", "C1~6" in X "Alkoxycarbonyl", "C1~6 alkylthio", "C1~6 alkylsulfinyl", "C1~6 alkylsulfinyl", and groups with substituents on these groups, The same as those exemplified in the above-mentioned R ⁴ and R ^{5 can be cited.}

Examples of the "amino group having a substituent" in X include the same ones as those ^{exemplified in R 5 above.}

Specific examples of the "aminocarbonyl group having substituents" in X include C1-6 alkanes such as methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, and diethylaminocarbonyl. A group substituted with an aminocarbonyl group.

Examples of "C3-8 cycloalkyl" in X include cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, and the like.

The "C6~10 aryl group" in X can be any of monocyclic and polycyclic. As long as at least one ring of the polycyclic aryl group is an aromatic ring, the remaining rings may be any of saturated aliphatic rings, unsaturated aliphatic rings, or aromatic rings.

Examples of the "C6-10 aryl group" include phenyl, naphthyl, azulenyl, indenyl, indenyl, and tetrahydronaphthyl.

Examples of the "C6-10 aryloxy group" in X include phenoxy and naphthoxy.

The "3-6 membered heterocyclic group" in X contains 1 to 4 heteroatoms selected from the group consisting of nitrogen atoms, oxygen atoms and sulfur atoms as the constituent atoms of the ring. The heterocyclic group may be any of a monocyclic ring and a polycyclic ring. As long as at least one ring of a polycyclic heterocyclic group is a heterocyclic ring, the remaining rings are saturated It can be any of alicyclic, unsaturated alicyclic or aromatic ring. 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.

基、

啉基、二氧雜環戊基(詳細為[1,3]二氧雜環戊基)、二氧雜環己基(詳細為[1,3]二氧雜環己基或[1,4]二氧雜環己基)等。較佳為5~6員飽和雜環基。 Examples of saturated heterocyclic groups with 3 to 6 members include: aziridinyl, epoxy, pyrrolidinyl, tetrahydrofuranyl, tetrahydrothiazolyl, piperidinyl, piperidine

base,

Alkyl, dioxolane ([1,3]dioxolyl), dioxanyl ([1,3]dioxanyl or [1,4]two Oxanyl) and so on. Preferably, it is a 5-6 membered saturated heterocyclic group.

唑基、異

唑基、噻唑基、異噻唑基、三唑基(詳細為[1,2,3]三唑基或[1,2,4]三唑基)、

二唑基(詳細為[1,2,4]

二唑基或[1,3,4]

二唑基)、噻二唑基、四唑基等。 Examples of 5-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl,

Azolyl, iso

Azolyl, thiazolyl, isothiazolyl, triazolyl (detailed as [1,2,3]triazolyl or [1,2,4]triazolyl),

Diazolyl (detailed as [1,2,4]

Diazolyl or [1,3,4]

Diazolyl), thiadiazolyl, tetrazolyl and the like.

基、嘧啶基、嗒

基、三

基等。 Examples of 6-membered heteroaryl groups include: pyridyl, pyridine

Base, pyrimidinyl, ta

Base, three

Base and so on.

唑啉基、異

唑啉基、噻唑啉基等。 Examples of partially unsaturated 5-membered heterocyclic groups include: pyrrolinyl, imidazolinyl (dihydroimidazolyl), pyrazolinyl,

Oxazoline, iso

Oxazolinyl, thiazolinyl, etc.

Examples of partially unsaturated 6-membered heterocyclic groups include thiopyranyl, 2H-pyridin-1-yl group, 4H-pyridin-1-yl group, and the like.

The 3- to 6-membered heterocyclic group is preferably a 5-membered heteroaryl group, more preferably a pyrazolyl group or a triazolyl group, and particularly further preferably a triazolyl group (more preferably [1,2,4]triazole base).

Examples of the substituents on the "C3~8 cycloalkyl", "C6~10 aryl", "C6~10 aryloxy" and "3~6 membered heterocyclic group" in X include: C1~6 Alkyl, C1~6 haloalkyl, hydroxy, C1~6 alkoxy, C1~6 alkoxycarbonyl, C1~6 alkylthio, C1~6 alkylsulfinyl, C1~6 alkyl Sulfonyl, amino, C1~6 alkyl substituted amino, halogen, Cyano, nitro, etc. Among these, preferred are C1-6 alkyl groups, C1-6 halogenated alkyl groups, hydroxyl groups, C1-6 alkoxy groups, halogen groups, cyano groups, and nitro groups.

As the "halogen group" in X, the same as those ^{exemplified in the above-mentioned R 4} and R ^{5 can be mentioned.}

Among the above-mentioned groups, X is preferably a C1-6 haloalkyl group or an unsubstituted or substituted 3-6 membered heterocyclic group.

In formula (Q-1), n represents the number of X that is chemically allowed, and is any integer from 0 to 4. When n is 2 or more, X may be the same or different from each other. Furthermore, in the case where either A ¹ or A ² is a nitrogen atom, the upper limit of the number of X chemically allowed is 3.

As n, 0-2 is preferable, and 1 is more preferable.

In the formula (Q-2), A ³ represents a carbon atom or a nitrogen atom.

In formula (Q-2), R ² and R ³ each independently represent a hydrogen atom, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, and an unsubstituted or substituted C2-6 alkenyl group. Substituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or substituted C1~6 alkoxy, methanoyl, unsubstituted or substituted C1~6 alkylcarbonyl, unsubstituted Substituted or substituted C1~6 alkoxycarbonyl group, mercapto group, unsubstituted or substituted C1~6 alkylthio group, unsubstituted or substituted C1~6 alkylsulfinyl group, Unsubstituted or substituted C1~6 alkylsulfonyl groups, unsubstituted or substituted amine groups, unsubstituted or substituted aminocarbonyl groups, unsubstituted or substituted C3~ 8-cycloalkyl, unsubstituted or substituted C6-10 aryl, unsubstituted or substituted C6-10 aryloxy, unsubstituted or substituted 3-6 membered heterocyclic group, Halogen, cyano or nitro. Wherein, when R ³ is a hydrogen atom, R ² is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclic group.

As the "C1~6 alkyl group", "C2~6 alkenyl group", "C2~6 alkynyl group", "C1~6 alkoxy group", "C1~6 alkylcarbonyl group" in ^{R 2} and R ³ "C1~6 Alkoxycarbonyl", "C1~6 Alkylthio", "C1~6 Alkylsulfinyl", and "C1~6 Alkylsulfinyl" and these groups have substitutions The base of the base may be the same as those ^{exemplified in the above-mentioned R 4} and R ^5.

Examples of the "amino group having a substituent" in R ² and R ³ include the same ones as those ^{exemplified in R 5 above.}

Examples of the "aminocarbonyl group having a substituent" in R ² and R ^{3 include the same ones as those exemplified in X above.}

As "C3~8 cycloalkyl", "C6~10 aryl", "C6~10 aryloxy" and "3~6 member heterocyclic group" in ^{R 2} and R ^{3, and these groups are substituted} The basis of the base may be the same as those exemplified in X above.

Examples of the "halogen group" in R ² and R ³ include the same as those ^{exemplified in R 4} and R ^{5 above.}

R ^{3 is} preferably a substituent other than a hydrogen atom, more preferably a halogen group, an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, and an unsubstituted C1-6 alkoxy group. Substituted or substituted amine group, unsubstituted or substituted C6~10 aryl group, unsubstituted or substituted C6~10 aryloxy group, and unsubstituted or substituted group 3~ The 6-membered heterocyclic group is particularly preferably an unsubstituted or substituted 3- to 6-membered heterocyclic group.

Here, in the formula (I), when Ar is an unsubstituted or substituted 5-membered heteroaryl group, Q is a group represented by the formula (Q-1); where Ar is unsubstituted or substituted When the C6~10 aryl group of the group or the unsubstituted or substituted 6-membered heteroaryl group, and R ⁴ is the unsubstituted or substituted amine group, Q is represented by the formula (Q-1) The group; where Ar is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 6-membered heteroaryl group, and R ⁴ is an unsubstituted or substituted amine group In the case of substituents, Q is a group represented by formula (Q-2). That is, the compound represented by formula (I) is a compound represented by formula (I-5) to formula (I-7).

In the formula (I-5), B ¹ , B ² , B ³ , B ⁴ , R ⁴ and R ⁵ have the same meanings as those in the formula (I). R ¹ , A ¹ , A ² , X and n have the same meanings as those in the formula (Q-1). In formula (I-5), Ar ¹ is an unsubstituted or substituted 5-membered heteroaryl group. As ^{the "5-membered heteroaryl group" in Ar 1} and the group having a substituent on this group, the same ones as exemplified in the above Ar can be mentioned.

In the formula (I-6), B ¹ , B ² , B ³ , B ⁴ and R ⁵ have the same meanings as those in the formula (I). R ¹ , A ¹ , A ² , X and n have the same meanings as those in the formula (Q-1). In formula (I-6), Ar ² is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 6-membered heteroaryl group, and R ⁶ is an unsubstituted or substituted group The amine group. As ^{the "C6-10 aryl group" and "6-membered heteroaryl group" in Ar 2} and the group having substituents on these groups, the same ones as exemplified in the above Ar can be mentioned. Examples of the amino group having a substituent in R ⁶ include the same groups as those ^{exemplified in R 4.}

In the formula (I-7), B ¹ , B ² , B ³ , B ⁴ and R ⁵ have the same meanings as those in the formula (I). R ¹ , R ² , R ³ and A ³ have the same meanings as those in the formula (Q-2). In formula (I-7), Ar ² is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 6-membered heteroaryl group. R ^{7 is a substituent other than the unsubstituted or substituted amine group in R 4} in formula (I). Specifically, it represents a hydrogen atom, a halogen group, a cyano group, an unsubstituted or substituted group C1~6 alkyl, unsubstituted or substituted C2~6 alkenyl, unsubstituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or substituted C1~6 alkoxy , Formyl, unsubstituted or substituted C1-6 alkylcarbonyl, unsubstituted or substituted C1-6 alkoxycarbonyl, unsubstituted or substituted C1-6 alkyl sulfide Group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkyl group Sulfonyloxy, -S(=O)(=NR ^a )-R ^b represents a group. Here, R ^a and R ^b each independently represent an unsubstituted or substituted C1-6 alkyl group. As ^{the "C6-10 aryl group" and "6-membered heteroaryl group" in Ar 2} and the group having substituents on these groups, the same ones as exemplified in the above Ar can be mentioned.

Moreover, as a preferable compound of the diarylazole compound of this invention, the compound represented by formula (I-8) or (I-9) can be mentioned.

In formula (I-8), Ar, B ¹ to B ⁴ , R ¹ to R ⁵ , and A ³ have the same meanings as those in formula (I) and formula (Q-2).

In formula (I-9), Ar, B ¹ ~ B ⁴ , R ¹ , R ⁵ , A ¹ , A ² , X and n represent the same as those in formula (I) and formula (Q-1) meaning. R ⁶ represents the same meaning as in formula (I-6).

The salt of the compound (I) is not particularly limited as long as it is a salt that is allowed in agriculture and horticulture. Examples of the salt of compound (I) include: salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium, and potassium; salts of alkaline earth metals such as calcium and magnesium; Salts of transition metals such as iron and copper; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, etc.

Regarding the compound (I) or the salt of the compound (I), the production method is not particularly limited. For example, the compound (I) or the salt of compound (I) of the present invention can be described in the examples, etc. Obtained by a known manufacturing method. In addition, the salt of compound (I) can be obtained from compound (I) by a known method.

The diarylazole compound of the present invention is excellent in preventing and controlling various agricultural pests, mites and other harmful organisms that affect the growth of plants.

In addition, the diarylazole compound of the present invention has low phytotoxicity to crops and low toxicity to fish or warm-blooded animals, so it is a compound with high safety. Therefore, it can be used as an effective ingredient in insecticides or acaricides.

Furthermore, in recent years, many pests such as diamondback moths, planthoppers, leafhoppers, and oil worms have developed resistance to organophosphorus agents and carbamate agents, which has caused the problem of insufficient efficacy of the above-mentioned agents. It is also an effective medicine against pests of resistant strains. The diarylazole compound of the present invention is not only effective against pests of susceptible strains, but also exhibits excellent control effects against pests of various resistant strains, or further acaricide-resistant strains of mites.

The diarylazole compound of the present invention is excellent in the prevention and control of external parasites and internal parasites that are harmful to humans and animals. In addition, since it has low toxicity to fish or warm-blooded animals, it is a compound with high safety. Therefore, it can be used as an effective ingredient of an antiparasitic agent for external and internal parasites.

In addition, the diarylazole compound of the present invention exhibits efficacy at all growth stages of organisms to be controlled, for example, it exhibits an excellent control effect against eggs, nymphs, larvae, pupae, and adults of mites and insects.

[Pest control agent, insecticide or acaricide]

The pest control agent, insecticide or acaricide of the present invention contains at least one selected from the diarylazole compounds of the present invention as an active ingredient. About the pest control agent and insecticide of the present invention Or the amount of the diarylazole compound contained in the acaricide is not particularly limited as long as it exhibits a pest control effect.

The pest control agent, insecticide or acaricide of the present invention is preferably used for: cereals; vegetables; root vegetables; potatoes; fruit trees, tea, coffee, cocoa and other trees; pastures; ; Cotton and other plants.

When applied to plants, the pest control agent, insecticide or acaricide of the present invention can be used for leaves, stems, stalks, flowers, buds, fruits, seeds, buds, roots, tubers, tubers, branches, cuttings, etc. Any part of it.

In addition, the pest control agent, insecticide or acaricide of the present invention is not particularly limited by the plant species to be applied. Examples of plant varieties include original species, varieties, improved varieties, cultivars, mutants, hybrids, modified organisms (GMO), and the like.

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

Hereinafter, specific examples of various agricultural pests and mites that can be controlled by the pest control agent of the present invention are disclosed.

(1) Lepidoptera (Lepidoptera) butterflies or moths

(a) Moths of the family Arctiidae, such as Hyphantria cunea, Lemyra imparilis; (b) Moths of the family Bucculatricidae, such as Bucculatrix pyrivorella); (c) Carposinidae, such as Carposina sasakii; (d) Crambidae moths, such as Diaphania spp. cotton Diaphania indica, Diaphania nitidalis; for example, Ostrinia furnacalis of Ostrinia spp., Ostrinia nubilalis, Purple Corn Borer (Ostrinia spp.) scapulalis); other rice borer (Chilo suppressalis), rice leaf roller (Cnaphalocrocis medinalis), peach borer (Conogethes punctiferalis), giant corn borer (Diatraea grandiosella), mulberry silkworm (Glyphodes pyloalis) , Chinese cabbage borer (Hellula undalis), bluegrass grass borer (Parapediasia teterrella); (e) Gelechiidae moths, such as Helcystogramma triannulella (Helcystogramma triannulella), cotton bollworm (Pectinophora gossypiella), Potato wheat moth (Phthorimaea operculella), wheat moth (Sitotroga cerealella); (f) Geometridae moths, such as Ascotis selenaria; (g) Gracillariidae moths, such as tea Caloptilia theivora, Phyllocnistis citrella, Phyllonorycter ringoniella; (h) Butterflies of the family Hesperiidae, such as Parnara guttata; (i) Lily moth Moths of the family (Lasiocampidae), such as Malacosoma neustria; (j) moths of the Lymantriidae family, such as Lymantria dispar (Lymantria dispar), Lymantria monacha (Lymantria monacha); others Euproctis pseudoconspersa (Euproctis pseudoconspersa), Orgyia thyellina (Orgyia thyellina); (k) Lyonetiidae (Lyonetiidae) moths, such as Lyonetia spp. (Lyonetia clerkella), Silver streak Leaf moth (Lyonetia prunifoliell a malinella); (l) Noctuidae (Noctuidae) moths, such as Spodoptera spp. (Spodoptera depravata), Southern Grey-winged Spodoptera (Spodoptera eridania), Sweet Spodoptera exigua, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura; e.g., Autographa spp. Autographa gamma, Autographa nigrisigna; such as Agrotis ipsilon and Agrotis segetum of the genus Agrotis spp.; such as Helicoverpa spp.) Helicoverpa armigera, Helicoverpa assulta, Helicoverpa zea; For example, Heliothis armigera and Heliothis armigera of Heliothis spp. (Heliothis virescens); other white spotted armyworm (Aedia leucomelas), silver-striped armyworm (Ctenoplusia agnata), withered leaf armyworm (Eudocima tyrannus), cabbage armyworm (Mamestra brassicae), sticky armyworm (Mythimna separata) , Naranga aenescens, Panolis japonica, Peridroma saucia, Pseudoplusia includens, Trichoplusia ni; (m) Noctuidae (Nolidae) moths, such as Earias insulana; (n) Pieridae (Pieridae) butterflies, such as Pieris brassicae (Pieris brassicae), Japanese white butterfly (Pieris rapae crucivora) ; (O) moths of the family Plutellae (Plutellidae), such as Acrolepiopsis sapporensis (Acrolepiopsis sapporensis), Acrolepiopsis suzukiella (Acrolepiopsis suzukiella) of the genus Acrolepiopsis spp.; other plutella xylostella; ( p) Moths of the family Pyralidae, such as Cadra cautella, South American corn seedling moth (Elasmop alpus lignosellus), Etiella zinckenella, Galleria mellonella; (q) Sphingidae (Sphingidae) moths, such as Manduca spp. Tomato hawk moth (Manduca quinquemaculata), tobacco hawk moth (Manduca sexta); (r) Stathmopodidae (Stathmopodidae) moths, such as persimmon hawk moth (Stathmopoda masinissa); (s) Tineidae moths , Such as Tinea translucens; (t) Tortricidae moths, such as Adoxophyes spp. (Adoxophyes honmai), Apple leaf rollers (Adoxophyes orana); for example Archips spp. (Archips spp.) Pear Yellow Roller Moth (Archips breviplicanus), Apple Leaf Roller Moth (Archips fuscocupreanus); Other Spruce Leaf Roller Moth (Choristoneura fumiferana), Apple Small Roller Moth (Cydia pomonella), Ligustrum lucidum (Eupoecilia ambiguella), Grapholitha molesta, Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Apple brown Pandemis heparana, Sparganothis pilleriana; (u) Yponomeutidae moths, such as Argyresthia conjugella.

(2) Thysanoptera pests

(a) Phlaeothripidae, such as Ponticulothrips diospyrosi; (b) Thripidae, such as Frankliniella intonsa (Frankliniella spp.) , West Flower Thrips (Frankliniella occidentalis); For example, Thrips spp. (Thrips palmi), Thrips tabaci (Thrips tabaci); other greenhouse thrips (Heliothrips haemorrhoidalis), tea yellow thrips (Thrips spp.) Scirtothrips dorsalis).

(3) Pests of Hemiptera

(A) Archaeorrhyncha

(a) Delphacidae such as Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, Sogatella furcifera.

(B) Clypeorrhyncha

(a) Cicadellidae, such as Empoasca fabae, Empoasca nipponica, Empoasca onukii, Empoasca onukii, Empoasca spp. Cicada (Empoasca sakaii); other grape leafhoppers (Arboridia apicalis), black-breasted two-chambered leafhoppers (Balclutha saltuella), two-spotted large leafhoppers (Epiacanthus stramineus), medium insect leafhoppers (Macrosteles striifrons), black-tailed leafhoppers (Nephotettix cinctinceps).

(C) Heteroptera

(a) Alydidae such as Riptortus clavatus; (b) Coreidae such as Cletus punctiger and Leptocorisa chinensis; (c) Examples of Lygaeidae (Blissus leucopterus), Cavelerius saccharivorus (Cavelerius saccharivorus), Togo hemipterus (Togo hemipterus); (d) Examples of Miridae Halticus insularis, Lygus lineolaris, Psuedatomoscelis seriatus, Stenodema sibiricum, Stenotus rubrovittatus, Trigonotylus caelestial Pentatomidae (Pentatomidae) such as Nezara spp. Nezara antennata, Nezara viridula; for example, Eysarcoris aeneus of Eysarcoris spp., Eysarcoris lewisi, Eysarcoris ventralis, Dolycoris baccarum, Eurydema rugosum, Glaucias subpunctatus, Halyomorpha halys, Piezodorus hybneri, Plautia crossota , Scotinophora lurida; (f) Pyrrhocoridae, such as Dysdercus cingulatus; (g) Rhopalidae, such as Rhopalus msculatus; (h) For example, Eurygaster integriceps in Scutelleridae; (i) Stephanitis nashi in Tingidae.

(D) Sternorrhyncha

(a) Adelgidae such as Adelges laricis; (b) Aleyrodidae such as Bemisia spp. (Bemisia argentifolii), tobacco powder Lice (Bemisia tabaci); other black whitefly (Aleurocanthus spiniferus), citrus whitefly (Dialeurodes citri), greenhouse whitefly (Trialeurodes vaporariorum); (c) Aphididae (Aphididae) such as Aphis spp. Aphis craccivora, broad bean aphid (Aphis fabae), grass borer phylloxera (Aphis forbesi), cotton aphid (Aphis gossypii), apple aphid (Aphis pomi), elder aphid (Aphis sambuci), leaf roller aphid (Aphis) spiraeeola); for example, Rhopalosiphum maidis (Rhopalosiphum maidis), Rhopalosiphum padi (Rhopalosiphum padi) of the genus Rhopalosiphum (Rhopalosiphum spp.); For example, Dysaphis plantaginea (Dysaphis plantaginea), sheep's hoof (Dysaphis plantaginea) of the genus Dysaphis spp. Phylloxera (Dysaphis radicola); for example, Macrosiphum avenae (Macrosiphum avenae) of the genus Macrosiphum spp., Potato aphid (Macrosiphum euphorbiae); such as Myzus cerasi, Myzus persicae, Myzus varians of Myzus spp.; other Acyrthosiphon pisum, eggplant Aulacorthum solani, Brachycaudus helichrysi, Brevicoryne brassicae, Chaetosiphon fragaefolii, Hyalopterus pruni, Hyperomyzus lactucae ), Lipaphis erysimi, Megoura viciae, Metopolophium dirhodum, Nasonovia ribis-nigri, Phorodon humuli, Schizaphis graminum, Sitobion avenae, Toxoptera aurantii; (d) Coccidae such as Ceroplastes spp. (Ceroplastes ceriferus), Ceroplastes rubens; (e) Pseudaulacaspis spp. of the Diaspididae family (Pseudaulacaspis spp.), Pseudaulacaspis pentagona, Pseudaulacaspis pruniculacaspis; for example Unaspis euonymi (Unaspis euonymi), Unaspis yanonensis (Unaspis yanonensis) of the genus Unaspis (Unaspis spp.); other red round scales (Aonidiella aurantii), Comstockaspis perniciosa, Tea single shield ( Fiorinia theae), Pseudaonidia paeoniae; (f) Margarodidae (Drosicha corpulenta), Icerya purchasi; (g) Phylloxeridae For example, grape phylloxera (Viteus vitifolii); (h) mealybugs (P seudococcidae), such as Planococcus citri (Planococcus citri) and Fuji mealybug (Planococcus kuraunhiae) of the genus Planococcus spp.; other root mealybugs (Phenacoccus solani) and Pseudococcus comstocki; (i) Psyllidae, such as Psylla mali (Psylla mali) and Psylla pyrisuga (Psylla pyrisuga) of the genus Psylla spp.; Other citrus psyllids (Diaphorina citri).

(4) Pests of Polyphaga

(a) Anobiidae such as Lasioderma serricorne; (b) Attelabidae such as Byctiscus betulae, Rhynchites heros; (c) Long worm (Bostrichidae) such as mealworms (Lyctus brunneus); (d) Tricone weevil (Brentidae) such as sweet potato ant weevil (Cylas formicarius); (e) Geetinidae (Buprestidae) such as pears Ding (Agrilus sinuatus); (f) Cerambycidae such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoderus; (g) Chrysomelidae, such as Bruchus pisorum and Bruchus rufimanus of Bruchus spp.; such as Diabrotica barberi of Diabrotica spp. ), cucumber beetle (Diabrotica undecimpunctata), corn root firefly beetle (Diabrotica virgifera); for example, Phyllotreta spp. (Phyllotreta nemorum), yellow striped leaf flea (Phyllotreta striolata); others Aulacophora femoralis, Callosobruchus chinensis, Cassida nebulosa, Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae, Eggplant Psylliodes angusticollis; (h) Coccinellidae (Coccinellidae), for example, Epilachna spp.) Mexican bean ladybug (Epilachna varivestis), sour sauce ladybug (Epilachna vigintioctopunctata); (i) Curculionidae (Curculionidae) such as Anthonomus spp. (Anthonomus spp.) Mexican cotton boll weevil (Anthonomus grandis) , Pear Weevil (Anthonomus pomorum); for example, Sitophilus granarius (Sitophilus granarius), Corn Weevil (Sitophilus zeamais); other rice weevil (Echinocnemus squameus), West Indian sweet potato weevil (Euscepes postfasciatus) ), Hylobius abietis, Hylobius abietis, Hypera postica, Lissohoptrus oryzophilus, Otiorhynchus sulcatus, Sitona lineatus, Sphenophorus venatus ); (j) Elateridae (Melanotus spp.) Melanotus fortnumi, Melanotus tamsuyensis (Melanotus tamsuyensis); (k) Nitidulidae ) Such as Epuraea domina; (l) Scarabaeidae such as Anomala spp. (Anomala cuprea), Anomala rufocuprea (Anomala rufocuprea); others Cetonia aurata, Gametis jucunda, Heptophylla picea, Melolontha melolontha, Popilia japonica; (m) Sclerotidae ( Scolytidae) such as Ips typographus; (n) Staphylinidae such as Paederus fuscipes; (o) Tenebriodidae such as yellow powder Tenebrio molitor, Tribolium castaneum; (p) Trogossi Tidae), for example, Tenebroides mauritanicus.

(5) Pests of Diptera

(A) Diptera (Brachycera)

(a) Liriomyza (Liriomyza bryoniae), Liriomyza chinensis (Liriomyza chinensis), Liriomyza sativae (Liriomyza sativae), Trilobite (Liriomyza spp.) Liriomyza trifolii; Other Chromatomyia horticola, Agromyza oryzae; (b) Ash of Anthomyiidae such as Delia spp. Delia platura, Delia radicum; other Pegomya cunicularia; (c) Drosophilidae (Drosophilidae), Drosophila spp., Drosophila spp. (Drosophila melanogaster), Drosophila suzukii; (d) Ephydridae such as Hydrellia griseola; (e) Psilidae such as Psila rosae); (f) Tephritidae such as Bactrocera cucurbitae and Bactrocera dorsalis of Bactrocera spp.; for example Rhagoletis spp. The cherry fruit fly (Rhagoletis cerasi), the apple fruit fly (Rhagoletis pomonella); the other Mediterranean fruit fly (Ceratitis capitata), the olive fruit fly (Dacus oleae).

(B) Nematocera

(a) Cecidomyiidae, such as soybean gall midge (Asphondylia yushimai), sorghum gall midge (Contarinia sorghicola), Hessian gall midge (Mayetiola destructor), and Sitodiplosis mosellana.

(6) Pests of Orthoptera

(a) Acrididae (Schistocerca spp.) American desert locust (Schistocerca americana), desert locust (Schistocerca gregaria); other Australian plague locust (Chortoicetes terminifera), Moroccan locust (Dociostaurus) maroccanus), East Asian migratory locust (Locusta migratoria), brown locust (Locustana pardalina), red-winged locust (Nomadacris septemfasciata), small-winged locust (Oxya yezoensis); (b) Gryllidae such as house cricket (Acheta domestica) , Yellow-faced oil gourd (Teleogryllus emma); (c) Gryllotalpidae (Gryllotalpidae) such as mole cricket (Gryllotalpa orientalis); (d) Tettigoniidae, such as Tachycines asynamorus.

(7) Acari

(A) Acaridida of the order Astigmata

(a) Acaridae (Acaridae), such as Rhizoglyphus (Rhizoglyphus spp.) Rhizoglyphus echinopus (Rhizoglyphus echinopus), Robin (Rhizoglyphus robini); for example, Tyrophagus spp. Tyrophagus neiswanderi (Tyrophagus neiswanderi), Tyrophagus perniciosus (Tyrophagus perniciosus), Tyrophagus putrescentiae (Tyrophagus putrescentiae), Tyrophagus similis (Tyrophagus similis); other Acarus siro (Acarus siro), Oval mealy Mite (Aleuroglyphus ovatus), Mycetoglyphus fungivorus (Mycetoglyphus fungivorus);

(B) Actinedida of Prostigmata

(a) Tetranychidae (Tetranychidae), such as Bryobia praetiosa (Bryobia praetiosa), Fruit moss (Bryobia rubrioculus) of the genus Bryobia (Bryobia spp.); For example, the citrus of the genus Eotetranychus spp. Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus celtis (Eotetranychus geniculatus), Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Eotetranychus smithi, Eotetranychus suginamensis , Eotetranychus uncatus; such as Oligonychus hondoensis of Oligonychus spp., Oligonychus ilicis, Oligonychus karamatus, Mango Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus shinkajii, Oligonychus perseae Mites (Oligonychus ununguis); for example, Panonychus citri (Panonychus citri), Panonychus mori (Panonychus mori), Panonychus ulmi (Panonychus ulmi) of the genus Panonychus (Panonychus spp.); for example, Tetranychus spp.) Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus ludeni, Hawthorn spider mite (Tetranychus quercivorus), Bean spider mite (Tetranychus phaselus), Two spotted leaf mite Tetranychus urticae, Tetranychus viennensis; such as Aponychus corpuzae and Aponychus firmianae of the genus Aponychus spp.; such as Sasanychus spp.) of the green spider mite (Sasanychus akitanus), the green spider mite (Sasanychus pusillus); for example, Shizotetranychus cela of the genus Shizotetranychus spp. rius), Shizotetranychus longus, Shizotetranychus miscanthi (Shizotetranychus miscanthi), Shizotetranychus recki, Shizotetranychus schizopus; other vines such as Tetranychina harti), Tuckerella pavoniformis (Tuckerella pavoniformis), Yezonychus sapporensis; (b) Tenuipalpidae (Tenuipalpidae) mites, such as Brachypidae (Brevipalpus spp.), Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus, Brevipalpus californicus ); for example, Tenuipalpus pacificus (Tenuipalpus pacificus), Persimmon zhizhilashviliae (Tenuipalpus zhizhilashviliae) of the genus Tenuipalpus (Tenuipalpus spp.); Other pineapple spider mites (Dolichotetranychus floridanus); (c) Eriophyidae ), such as Aceria diospyri (Aceria diospyri), Aceria ficus, Aceria japonica, Aceria japonica, Aceria kuko, Carnation gall mites of Aceria spp. Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes chibaensis of Eriophyes spp., Eriophyes emarginatae; for example, Eriophyes emarginatae Aculops lycopersici (Aculops lycopersici) and Aculops pelekassi (Aculops pelekassi) of the genus (Aculops spp.); for example, Aculus fockeui of the genus Aculus spp. , Aculus schlechtendali (Aculus schlechtendali); other tea orange gall mite (Acaphylla theavagrans), tea gall mite (Calacarus carinatus), grape gall mite (Colomerus vitis), grape leaf rust mite (Calepitrimerus vitis), date leaf Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi, Phyllocotruta citri; (d) Transonemidae mites, such as Tarsus Tarsonemus spp. (Tarsonemus spp.) ilobatus), Tarsonemus waitei (Tarsonemus waitei); other primrose plant-eating mites (Phytonemus pallidus), Polyphagotarsonemus latus (Polyphagotarsonemus latus); (e) The mites of the family Penthaleidae, such as Penthaleus erythrocephalus (Penthaleus erythrocephalus) and Penthaleus major (Penthaleus spp.).

The pest control agent of the present invention can be mixed with other active ingredients such as fungicides, insecticides, acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. Or use it together.

For the combination of the compound of the present invention and other active ingredients, a synergistic effect on insecticidal and acaricidal activities can be expected. The synergistic effect can be confirmed according to the established method and according to the Colby formula (Colby.S.R.; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pages 20-22, 1967).

[External Parasite Control Agent]

The ectoparasite control agent of the present invention contains at least one selected from the diarylazole compounds of the present invention as an active ingredient. The diarylazole compound of the present invention is excellent in the effect of preventing external parasites that harm humans and animals.

Examples of external parasites include mites, lice, fleas, mosquitoes, barbed wire, and flesh flies.

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

External parasites are parasitic in and on host animals, especially warm-blooded animals. In detail, external parasites are parasitic on the back, underarms, lower abdomen, inner part of the legs, etc. of the host animal, and the animals obtain nutrients such as blood or skin to inhabit.

The ectoparasite control agent of the present invention can be obtained by known veterinary methods (Bureau Partial, oral, parenteral or subcutaneous administration). Examples of the method include: oral administration to animals by mixing tablets, capsules, feed, etc.; by immersion solution, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), etc. The method of administering to animals; the method of locally administering oily or aqueous liquids by spray, pour-on, spot-on, etc.; kneading the external parasite control agent In the resin, the above-mentioned kneaded material is formed into appropriate shapes such as collars and earrings, and these are put on the body of an animal and then locally administered.

Hereinafter, specific examples of external parasites that can be controlled by the external parasite control agent of the present invention are disclosed.

(1) Acari

Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae ), mites of the family Psoroptidae, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodexidae, mites of the family Trombiculidae , Coleopterophagus and other insect parasitic mites.

(2) Phthiraptera

Haematopinidae (Haematopinidae), Linognathidae (Linognathidae), Short-horned bird lice (Menoponidae) Feather lice, Long-horned bird lice (Philopteridae) Feather lice, Trichodectidae (Trichodectidae) Feather lice.

(3) Siphonaptera

Fleas of the family Pulicidae, such as those of the genus Ctenocephalides spp., Ctenocephalides canis, Ctenocephalides felis; Ctenocephalides felis; (Tungidae) fleas, Ceratophyllidae (Ceratophyllidae) fleas, Leptopsyllidae (Leptopsyllidae) fleas.

(4) Hemiptera

(5) Pests of Diptera

Culicidae mosquitoes, Simuliidae gnats, Ceratopogonidae midges, Tabanidae flies, Muscidae flies, Glossinidae tsetse flies , Sarcophagidae, Sarcophagidae, Hippoboscidae, Calliphoridae, Oestridae.

[Internal parasite control or repellent]

The internal parasite control or repellent of the present invention contains at least one selected from the diarylazole compounds of the present invention as an active ingredient.

The parasites that are the objects of the internal parasite control or repellent of the present invention parasitize host animals, especially warm-blooded animals or fish (internal parasites). Examples of host animals effective for the parasite control or repellent of the present invention include humans, livestock mammals (such as cows, horses, pigs, sheep, goats, etc.), experimental animals (such as mice, rats, and long-clawed deserts). Rats, etc.), pet animals (such as hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, bison, etc.), poultry (turkeys, ducks, etc.) , Chicken, quail, geese, etc.), pet birds (pigeons, parrots, nine-guan birds, manbirds, parrots, ten sisters, canaries, etc.) and other temperature-controlled animals; or salmon, trout, koi and other fish. By preventing and repelling parasites, it is possible to prevent or treat parasitic diseases caused by parasites.

As the parasites to be prevented or repelled, the following can be cited.

(1) Nematodes of the order Dioctophymatida

(a) Dioctophymatidae (Dioctophymatidae), for example Dioctophyma renale (Dioctophyma renale); (b) Sables (Soboliphymatidae), such as sable Soboliphyme abei and Soboliphyme baturini of Soboliphyme spp.

(2) Nematodes of the order Trichocephalida

(a) Trichinella spiralis (Trichinellidae), such as Trichinella spiralis (Trichinella spp.); (b) Trichinella spiralis (Trichuridae), such as Capillaria spp.), Capillaria annulata, Capillaria contorta, Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria spp. (Capillaria suis); Trichuris vulpis, Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris spp. (Trichuris suis).

(3) Nematodes of the order Rhabditida

Strongyloididae (Strongyloididae), for example, Strongyloides spp., Strongyloides papillosus, Strongyloides planiceps, Strongyloides planiceps, Strongyloides spp. ransomi), Strongyloides suis (Strongyloides suis), Strongyloides stercoralis (Strongyloides stercoralis), Strongyloides tumefaciens (Strongyloides tumefaciens), Strongyloides ratti (Strongyloides ratti).

(4) Nematodes of the order Strongylida

Hookworms of the family Ancylostomatidae, such as Ancylostoma spp. Ancylostoma braziliense (Ancylostoma braziliense), Ancylostoma caninum (Ancylostoma caninum), Ancylostoma duodenale (Ancylostoma duodenale), Ancylostoma tubaeforme (Ancylostoma tubaeforme); Narrow head of Uncinaria spp. Uncinaria stenocephala (Uncinaria stenocephala); Bunostomum phlebotomum (Bunostomum phlebotomum), Bunostomum trigonocephalum (Bunostomum trigonocephalum) of the genus Bunostomum spp.

(5) Nematodes of the order Strongylida

(a) Angiostrongylidae (Angiostrongylidae) nematodes, such as Aelurostrongylus spp. (Aelurostrongylus abstrusus); Angiostrongylus spp. (Angiostrongylus spp.) Angiostrongylus vasorum, Angiostrongylus cantonesis; (b) Nematodes of Crenosomatidae, such as Crenosoma aerophila and Crenosoma vulpis of Crenosoma spp. ; (C) Filaroididae (Filaroididae) nematodes, such as Filaroides spp. (Filaroides hirthi), Filaroides osleri (Filaroides osleri); (d) Poststrongy nematodes Metastrongylidae, for example, Metastrongylus apri, Metastrongylus asymmetricus, Metastrongylus pudendotectus, Metastrongylus pudendotectus, Metastrongylus spp. salmi); (e) Syngamidae (Syngamidae), such as Cyathostoma bronchialis (Cyathostoma bronchialis) of Cyathostoma spp.; Syngamus spp. (Syngamus spp.) Syngamus skrjabinomorpha), trachea than wing nematode (Syngamus trachea).

(6) Nematodes of the order Strongylida

(a) Nematodirus (Nematodirus spp.) Nematodirus (Nematodirus filicollis), Nematodirus spathiger (Nematodirus spathiger); (b) Net tail Nematodes of Dictyocaulidae, such as Dictyocaulus filaria of Dictyocaulus spp., Dictyocaulus viviparus (Dictyocaulus viviparus); (c) of Haemonchidae Nematodes, such as Haemonchus contortus of Haemonchus spp.; Mecistocirrus digitatus of Mecistocirrus spp.; (d) Stomach contortion Nematodes of Haemonchidae, such as Ostertagia ostertagi of Ostertagia spp.; (e) Nematodes of Heligmonellidae, such as Nippostrongylus spp. Nippostrongylus braziliensis; (f) Trichostrongylidae nematodes, such as Trichostrongylus spp. Trichostrongylus axei, Trichostrongylus colubriformis ), Trichostrongylus tenuis (Trichostrongylus tenuis); Hyostrongylus rubidus (Hyostrongylus spp.); Obeliscoides cuniculi (Obeliscoides spp.).

(7) Nematodes of the order Strongylida

(a) Nematodes of the Chabertiidae family (Chabertiidae), such as Chabertiidae (Chabertia spp.) Sheep Chabertia ovina; Oesophagostomum brevicaudatum, Oesophagostomum columbianum, Oesophagostomum columbianum, Oesophagostomum brevicaudatum, Oesophagostomum spp. Oesophagostomum georgianum, Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum radiatum, Oesophagostomum (Oesophagostomum maplestonei), Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum (Oesophagostomum) Nematodes of Stephanuridae, such as Stephanurus dentatus of Stephanurus spp.; (c) Nematodes of Strongylidae, such as Strongylus spp. Strongylus asini, Strongylus edentatus, Strongylus equinus, Strongylus vulgaris.

(8) Nematodes of the order Oxyurida

Nematodes of the Oxyuridae family, such as Enterobius anthropopitheci of Enterobius spp., Enterobius vermicularis, and horse tails of Oxyuris spp. Oxyuris equi; Passalurus ambiguus of Passalurus spp.

(9) Nematodes of the order Ascaridida

(a) Nematodes of the family Ascaridiidae, such as Ascaridia galli of Ascaridia spp.; (b) Nematodes of the Heterakidae family, such as Heterakis spp. .) of Heterakis beramporia, Heterakis beramporia brevispiculum), Heterakis gallinarum, Heterakis pusilla, Heterakis putaustralis; (c) Nematodes of the Anisakidae family, such as Anisakis spp.) simple anisakis (Anisakis simplex); (d) Ascarididae (Ascarididae) nematodes, such as Ascaris spp. (Ascaris lumbricoides), pig roundworms (Ascaris suum); Paraascaris spp. (Parascaris spp.) Parascaris equorum; (e) Toxocaridae (Toxocaridae) nematodes, such as Toxocara spp. (Toxocara spp.) Toxocara canis (Toxocara canis), Lion's bow Nematode (Toxocara leonina), Toxocara suum (Toxocara suum), Toxocara vitulorum (Toxocara vitulorum), Toxocara cati (Toxocara cati).

(10) Nematodes of the order Spirurida

(a) Nematodes of the Onchocercidae family (Onchocercidae), such as Brugia spp. (Brugia malayi), Brugia pahangi (Brugia pahangi), Pat Brugia patei; Dipetalonema reconditum (Dipetalonema reconditum) of Dipetalonema spp.; Dirofilaria immitis (Dirofilaria immitis) of Dipetalonema spp.; Silk Filaria oculi (Filaria spp.); Onchocerca cervicalis (Onchocerca cervicalis), Onchocerca gibsoni (Onchocerca gibsoni), laryngoma (Onchocerca spp.) Onchocerca gutturosa; (b) Nematodes of the Setariidae family, such as Setaria digitata of Setaria spp., Setaria equina , Setaria labiatopapillosa (Setaria labiatopapillosa), Setaria marshalli (Setaria marshalli); Wu Ce Wuchereria bancrofti of the genus (Wuchereria spp.); (c) Nematodes of Filariidae, such as Parafilaria spp. (Parafilaria multipapillosa) Stephanofilaria (Stephanofilaria spp.), Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi).

(11) Nematodes of the order Spirurida

(a) Nematodes of Gnathostomatidae, such as Gnathostoma doloresi and Gnathostoma spinigerum of Gnathostoma spp.; (b) Gnathostoma spinigerum ( Habronematidae), such as Habronema majus (Habronema spp.), Habronema microstoma, Habronema muscae (Habronema muscae); Drachia spp. Draschia megastoma; (c) Nematodes of the Physalopteridae family (Physalopteridae), such as Physaloptera canis (Physaloptera spp.), Physaloptera cesticillata ), Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaloptera rara, Siberia rara (Physaloptera sibirica), Physaloptera vulpineus; (d) Nematodes of the family Gongylonematidae, such as Gongylonema spp.) Gongylonema pulchrum; (e) Spirocercidae nematodes, such as Ascarops strongylina of Ascarops spp.; (f) Sucking nematodes (Thelaziidae) nematodes, such as Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Thelazia rhodesi (Thelazia spp.) ), Scriabin sucking nematode (Thelazia skrjabini).

[Inhibitors against other harmful organisms]

In addition, it is also excellent in the prevention and control of pests that have poisonous needles or venom that can harm humans and animals, pests that act as vectors for various pathogens and pathogens, and pests that cause discomfort to people (toxic pests, sanitary pests, unpleasant pests, etc.) .

Hereinafter, specific examples will be disclosed.

(1) Pests of Hymenoptera

Bees of Argidae, Cynipidae, Diprionidae, Formicidae, Mutillidae, Vespidae ) Of the bee.

(2) Other pests

Blattodea, termite, Araneae, cetipede, millipede, crustacea, bed bug (Cimex lectularius).

Among the above-mentioned harmful organisms, the diarylazole compound of the present invention has an excellent insecticidal effect on thrips, planthoppers, leafhoppers, cockroaches, golden flower insects, etc. in particular.

[Preparation formula]

Below, several formulations of the pest control agents, insecticides or acaricides, external parasite control agents, or internal parasite control or repellents of the present invention are disclosed, but the additives and the addition ratio should not be limited to these implementations For example, it can be changed in a wide range. The parts in the formulations represent parts by weight.

Hereinafter, the formulations of agricultural and horticultural and rice preparations are disclosed.

(Formulation 1: Hydrating agent)

40 parts of the diarylazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfates, and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and finely pulverized to obtain water with 40% of active ingredients mixture.

(Formulation 2: Emulsion)

30 parts of the diarylazole compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion with 30% of active ingredients .

(Formulation 3: Granules)

5 parts of the diarylazole 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 finely pulverized, and then granulated into granules with a diameter of 0.5 to 1.0 mm Form, and obtain 5% active ingredient granules.

(Formulation 4: Granules)

5 parts of the diarylazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and fully kneaded, and then manufactured The granules are dried to obtain granules with 5% active ingredient.

(Formulation 5: Suspending agent)

Combine 10 parts of the diarylazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, and polycarboxylate Mix 2 parts of sodium salt, 10 parts of glycerin, 0.2 part of Sanxian gum, and 73.8 parts of water, and perform wet pulverization until the particle size becomes less than 3 microns to obtain a suspension of 10% active ingredient.

Hereinafter, the formulation of the external parasite control agent or the internal parasite control or repellent is disclosed.

(Formulation 6: Granules)

Dissolve 5 parts of the diarylazole compound of the present invention in an organic solvent to obtain a solution, spray the above-mentioned solution onto 94 parts of kaolin and 1 part of white carbon, and then evaporate the solvent under reduced pressure. Such particles can be mixed with animal food.

(Formulation 7: Injection)

0.1 to 1 part of the diarylazole compound of the present invention is uniformly mixed with 99 to 99.9 parts of peanut oil, and then filtered and sterilized by a sterilizing filter.

(Formulation 8: Pouring agent)

5 parts of the diarylazole compound of the present invention, 10 parts of myristate, and 85 parts of isopropanol are uniformly mixed to obtain a pouring agent.

(Formulation 9: drops)

10-15 parts of the diarylazole compound of the present invention, 10 parts of palmitate, and 75-80 parts of isopropanol are uniformly mixed to obtain drops.

(Formulation 10: Spray)

1 part of the diarylazole compound of the present invention, 10 parts of propylene glycol, and 89 parts of isopropanol were uniformly mixed to obtain a spray.

Next, the present invention will be explained more specifically by revealing compound examples. However, the present invention is not limited in any way by the following compound examples.

[Example 1]

1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-5-amine[ 1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-amine] (Compound No. 1-12), and 5-chloro-1 -(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole[5-chloro-1 -(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole] (Compound No. 1-17) Synthesis

(Step 1-1)

Synthesis of 2-ethylthio-1-fluoro-4-(trifluoromethyl)benzene [2-ethylthio-1-fluoro-4-(trifluoromethyl)benzene]

Dissolve 22 g (0.12 mol) of 2-fluoro-5-(trifluoromethyl)aniline and 7.3 g (0.060 mol, 0.5 eq) of diethyl disulfide in 300 ml of acetonitrile and heat to 30°C. 14 g (0.12 mol, 1.0 eq) of isoamyl nitrite was added dropwise, and the mixture was stirred under heating and reflux for one hour. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 11 g of the target product (yield 39%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 7.59 (m, 1H), 7.46 (m, 1H), 7.15 (m, 1H), 2.98 (q, 2H), 1.33 (t, 3H).

(Step 1-2)

Synthesis of 2-(ethylsulfonyl)-1-fluoro-4-(trifluoromethyl)benzene [2-(ethylsulfonyl)-1-fluoro-4-(trifluoromethyl)benzene]

1.9 g (8.5 mmol) of 2-ethylthio-1-fluoro-4-(trifluoromethyl)benzene was dissolved in 80 ml of chloroform, and the mixture was stirred at room temperature. 5.2 g (70%, 21 mmol, 2.5 eq) of m-chloroperbenzoic acid was added thereto and stirred at 50° C. overnight. This reaction solution was poured into a mixed solution of a saturated sodium bicarbonate aqueous solution and a saturated sodium thiosulfate aqueous solution, followed by extraction with dichloromethane. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 2.0 g of the target product (yield 80%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.26 (m, 1H), 7.94 (m, 1H), 7.40 (m, 1H), 3.37 (q, 2H), 1.35 (t, 3H).

(Steps 1-3)

5-amino-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylic acid ethyl ester [ethyl 5-amino-1-( Synthesis of 2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylate]

2.0 g (7.6 mmol) of 2-(ethylsulfonyl)-1-fluoro-4-(trifluoromethyl)benzene was dissolved in 15 ml of ethanol, and the mixture was stirred at room temperature. To this, 3.0 g (61 mmol, 8.0 eq) of hydrazine monohydrate was added and reacted at 150°C for one hour. This reaction solution was poured into water, and extraction was performed with toluene. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was dissolved in 13 ml of ethanol and stirred at room temperature. 1.3 g (7.6 mmol, 1.0 eq) of ethyl (ethoxymethylene) cyanoacetate was added thereto, and the mixture was stirred under heating and reflux overnight. The reaction solution was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.9 g of the target product (yield 65%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ + D ₂ O ^* ): δ 8.07 (m, 1H), 7.81 (m, 1H), 7.47 (s, 1H), 7.14 (m, 1H), 4.30 (q, 2H) ), 3.22(q,2H), 1.37(t,3H), 0.88(t,3H).

( ^* : The solvent obtained by adding a drop of D ₂ O to 0.7ml of CDCl ₃₎

(Steps 1-4)

1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-5-amine[1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl) -1H-pyrazol-5-amine] Synthesis

Dissolve 1.9 g (4.9 mmol) of ethyl 5-amino-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-4-carboxylate in Concentrated hydrochloric acid 14ml, stirred for five hours under heating and refluxing. This reaction solution was poured into water, and potassium carbonate was added for neutralization. After that, extraction was performed with dichloromethane. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.1 g of the target product (yield 71%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.46 (d, 1H), 8.03 (m, 1H), 7.59 (m, 1H), 7.52 (m, 1H), 5.69 (d, 1H), 3.81 (br s, 2H), 3.19(q, 2H), 1.24(t, 3H).

(Steps 1-5)

4-bromo-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-5-amine[4-bromo-1-(2-(ethylsulfonyl) Synthesis of -4-(trifluoromethyl)phenyl)-1H-pyrazol-5-aminej

Dissolve 1.1 g (3.4 mmol) of 1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazol-5-amine in 10 ml of acetic acid, and stir at room temperature . Into it 0.55 g (0.55 g, 1.0 eq) of bromine was added dropwise, and stirred at room temperature for 30 minutes. This reaction solution was poured into water, and potassium carbonate was added for neutralization. After that, extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with a mixed solvent of chloroform and n-hexane, thereby obtaining 1.2 g of the target product (yield 86%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.46 (m, 1H), 8.04 (m, 1H), 7.56 (m, 1H), 7.54 (s, 1H), 3.93 (br s, 2H), 3.20 ( q, 2H), 1.24 (t, 3H).

(Steps 1-6)

1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole-5-amine[ Synthesis of 1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-amine] (Compound No. 1-12)

Dissolve 1.0 g (2.5 mmol) of 4-bromo-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-1H-pyrazole-5-amine in 6ml of toluene and water 2.2ml of mixed solvent, stir at room temperature. Add 0.78g (3.8mmol, 1.5eq) of p-trifluoromethoxyphenylboronic acid, 0.028g (0.13mmol, 5.0mol%) of palladium(II) acetate, and 0.12g of X-Phos (0.25mmol, 10mol%) and 1.1g (5.0mmol, 2.0eq) of potassium phosphate, stirred at 90°C for three hours in an argon atmosphere. This reaction solution was poured into water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.92 g of the target product (yield 77%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.49 (m, 1H), 8.07 (m, 1H), 7.72 (s, 1H), 7.66 (m, 1H), 7.46 (m, 2H), 7.29 (m , 2H), 3.99 (br s, 2H), 3.27 (q, 2H), 1.26 (t, 3H).

(Steps 1-7)

5-chloro-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole[ Synthesis of 5-chloro-1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazole] (Compound No. 1-17)

Make 1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-pyrazol-5-amine 0.3 g (0.63 mmol) was dissolved in concentrated hydrochloric acid and stirred at 0°C. 0.052 g (0.75 mmol, 1.2 eq) of sodium nitrite was added thereto, and the mixture was stirred at 0°C for one hour. 0.17 g (1.3 mmol, 2.0 eq) of copper (II) chloride was added thereto, and the mixture was stirred at 55°C overnight. This reaction solution was poured into water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.16 g of the target product (yield 51%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.49 (m, 1H), 8.08 (m, 1H), 7.95 (s, 1H), 7.70-7.66 (m, 3H), 7.30 (m, 2H), 3.51 (q,2H),1.31(t,3H).

[Example 2]

1-(2-(ethylthio)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3 -Triazole [1-(2-(Ethylthio)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole] (Compound No.: 4-5), and 1-(2-(ethylsulfonyl)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl) -1H-1,2,3-Triazole [1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2, Synthesis of 3-triazole] (Compound No. 4-6)

(Step 2-1)

Synthesis of 1-Azido-2-chloro-4-(trifluoromethyl)benzene [1-Azido-2-chloro-4-(trifluoromethy)benzene]

Dissolve sodium nitrite (0.85g) in concentrated sulfuric acid (6ml), add dropwise 2-chloro-4-(three Fluoromethyl)aniline (2.0g) in acetic acid (12ml). After warming to room temperature and stirring for 30 minutes, it was cooled to 0°C, an aqueous solution (3 ml) of sodium azide (0.65 g) was added dropwise, and the mixture was stirred at room temperature overnight. This reaction solution was poured into water, and extraction was performed with diethyl ether. The obtained organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was used in the next step without purification.

(Step 2-2)

1-(2-Chloro-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole[ Synthesis of 1-(2-Chloro-4-(trifluoromethy)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole]

4-trifluoromethylphenylacetone (1.7g) was dissolved in methanol (60ml), the inside of the reaction vessel was replaced with nitrogen, and the mixture was stirred at room temperature. Add sodium methoxide (0.68g) and 1-azido-2-chloro-4-(trifluoromethyl)benzene (ca.10mmol) prepared in step 2-1 to it, and stir overnight at room temperature . This reaction solution was poured into water, and extraction was performed with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was washed with n-hexane to obtain 2.3 g of the target product (yield 67%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 7.95 (d, 2H), 7.92 (s, 1H), 7.78 (d, 1H), 7.75 (d, 2H), 7.66 (d, 1H), 2.42 (s) ,3H).

(Steps 2-3)

1-(2-(Ethylthio)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl-1H-1,2,3- Synthesis of Triazole [1-(2-(Ethylthio)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole] (Compound No. ：4-5)

Make 1-(2-chloro-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole (1.0g) was dissolved in N,N-dimethylformamide (25ml) and stirred at room temperature. Sodium ethyl mercaptan (80%, 0.31 g) was added thereto, and the mixture was stirred at room temperature overnight. This reaction solution was poured into water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.94 g of the target product (yield 87%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 7.96 (d, 2H), 7.74 (d, 2H), 7.69 (s, 1H), 7.61 (d, 1H), 7.48 (d, 1H), 2.91 (q ,2H), 2.39(s, 3H), 1.29(t, 3H).

(Steps 2-4)

1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4 -(Trifluoromethyl)phenyl)-1H-1,2,3-triazole [1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl) )phenyl)-1H-1,2,3-triazole] Synthesis (Compound No. 4-6)

Make 1-(2-(ethylthio)-4-(trifluoromethyl)phenyl)-5-methyl-4-(4-(trifluoromethyl)phenyl-1H-1,2,3 -Triazole (0.88g) was dissolved in dichloromethane (20ml) and stirred at 0°C. m-chloroperbenzoic acid (70%, 1.0g) was added to it, and stirred at room temperature overnight. The reaction solution was poured into To the mixed solution of saturated sodium bicarbonate aqueous solution and saturated sodium thiosulfate aqueous solution, extract with dichloromethane. Wash the obtained organic layer with saturated brine, dry it with anhydrous magnesium sulfate and filter. The filtrate The residue was concentrated under reduced pressure and purified by silica gel column chromatography to obtain 0.74 g of the target product (yield 90%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.54 (s, 1H), 8.14 (d, 1H), 7.93 (d, 2H), 7.74 (d, 2H), 7.63 (d, 1H), 3.31 (q ,2H), 2.40(s,3H), 1.28(t,3H).

[Example 3]

1-(2-(ethylthio)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole[ Synthesis of 1-(2-(Ethylthio)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole] (Compound No. 4-7), and 1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)benzene Yl)-4-(4-(trifluoromethyl)phenyl)-1H-1,2,3-triazole [1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-( Synthesis of 4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole] (Compound No. 4-8)

(Step 3-1)

Synthesis of 1-Azido-2-fluoro-4-(trifluoromethyl)benzene [1-Azido-2-fluoro-4-(trifluoromethyl)benzene]

Sodium nitrite (1.2g) was dissolved in concentrated sulfuric acid (9ml), and an acetic acid solution (18ml) of 2-fluoro-4-(trifluoromethyl)aniline (2.8g) was added dropwise at 0°C. After warming to room temperature and stirring for 30 minutes, it was cooled to 0°C, an aqueous solution (3 ml) of sodium azide (0.98 g) was added dropwise, and the mixture was stirred at room temperature overnight. This reaction solution was poured into water, and extraction was performed with diethyl ether. The obtained organic layer was washed with saturated sodium bicarbonate aqueous solution and saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was directly used in the next step without purification.

(Step 3-2)

1-(2-Fluoro-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole [1-(2 Synthesis of -Fluoro-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole]

Dissolve the 1-azido-2-fluoro-4-(trifluoromethyl)benzene (ca.5.0mmol) prepared in step 3-1 in a mixed solvent of acetonitrile (10ml) and water (20ml). Stir at room temperature. 1-ethynyl-4-(trifluoromethoxy)benzene (1.0 g), copper sulfate pentahydrate (0.12 g), and hydrazine hydrate (0.25 g) were added thereto, and the mixture was stirred at room temperature for 2 hours. This reaction solution was poured into water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 1.1 g of the target product (yield 54%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.38 (d, 1H), 8.28 (t, 1H), 7.95 (m, 2H), 7.65 (d, 1H), 7.62 (d, 1H), 7.32 (d ,2H).

(Step 3-3)

1-(2-(ethylthio)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole[ Synthesis of 1-(2-(Ethylthio)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole] (Compound No. 4-7)

Make 1-(2-fluoro-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole (1.0g) Dissolve in N,N-dimethylformamide (10ml) and stir at room temperature. Sodium ethyl mercaptan (80%, 0.31 g) was added thereto, and the mixture was stirred at room temperature overnight. This reaction solution was poured into water, followed by extraction with ethyl acetate. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.96 g of the target product (yield 90%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.22 (s, 1H), 7.95 (m, 2H), 7.10 (d, 1H), 7.67 (d, 1H), 7.61 (dd, 1H), 7.32 (d ,2H), 2.90(q,2H), 1.27(t,3H).

(Steps 3-4)

1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-tri Synthesis of azole [1-(2-(Ethylsulfonyl)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole] (Compound No. 4-8)

Make 1-(2-(ethylthio)-4-(trifluoromethyl)phenyl)-4-(4-(trifluoromethoxy)phenyl)-1H-1,2,3-triazole (0.70g) was dissolved in dichloromethane (10ml) and stirred at 0°C. M-chloroperbenzoic acid (70%, 0.87 g) was added thereto, and the mixture was stirred at room temperature overnight. will The reaction solution was poured into a mixed solution of saturated sodium bicarbonate aqueous solution and saturated sodium thiosulfate aqueous solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried with anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 0.64 g of the target product (yield 85%).

^{The 1} H-NMR of the obtained target product is shown below.

¹ H-NMR (400MHz, CDCl ₃ ): δ 8.53 (d, 1H), 8.24 (s, 1H), 8.10 (dd, 1H), 7.94 (m, 2H), 7.73 (d, 1H), 7.32 (d ,2H), 3.21(q,2H), 1.27(t,3H).

The compounds of the present invention produced by the same method as the above-mentioned examples are shown in Tables 1 to 5. Table 1 discloses the substituents of the compound represented by formula (I-1-1). Table 2 discloses the substituents of the compound represented by formula (I-1-2). Table 3 discloses the substituents of the compound represented by formula (I-2-1). Table 4 discloses the substituents of the compound represented by formula (I-3-1). The physical properties of the compound are recorded in the "Properties" column. As physical property data, properties, melting point (mp), or refractive index (n _D ) are described. Regarding the abbreviations in the table, Me stands for methyl, Et stands for ethyl, and tBu stands for tertiary butyl.

^{The 1} H-NMR data (400 MHz, CDCl ₃ ) of some of the compounds described in Tables 1 to 5 above are shown in Table 6.

As described above, the diarylazole compound of the present invention can be easily produced by using the well-known chemical reaction as in the above-mentioned embodiment. According to the description of this specification, those in the industry can easily understand that other compounds not specifically exemplified in this specification, that is, those substituted with various groups that do not deviate from the spirit and scope of the present invention, can be produced by the above methods, etc. And can be used.

[Biological test]

The following test examples reveal that the diarylazole compound of the present invention (hereinafter referred to as the compound of the present invention) can be used as an active ingredient of a pest control agent and an ectoparasite control agent. In addition, "parts" are based on weight.

(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 prepare 5% of the effective ingredient The emulsion (I).

The insecticidal rate and control rate are calculated by the following formula.

Insecticidal rate (%) = (the number of dead insects / the number of test insects) × 100

Prevention rate={1-(Nt)/(Nc)}×100

Nt: the number of parasites in the dispersal treatment area

Nc: the number of parasites in the untreated area

(Test Example 1) Effectiveness test against Spodoptera exigua

Mix 0.8 g of commercially available artificial feed (Insecta LFS, manufactured by Nippon Agricultural Industry Co., Ltd.) and 1 μl of emulsion (I), and put 0.2 g of each treatment area into a plastic test container (1.4 ml volume) to prepare it. Test feed.

Each treatment area was inoculated with 2 second-instar larvae of Spodoptera exigua and sealed with a plastic cover. Place it in a constant temperature room at 25°C, and investigate the insecticidal rate and food intake on the 5th day. The test was repeated twice. In addition, the compound of the present invention was removed from the emulsion (I), and the test was conducted under the same conditions, and the test was set as the solvent control zone.

For the compounds shown in Table 7, the efficacy test against Spodoptera exigua was conducted. Each compound has an insecticidal rate of 100% against Spodoptera exigua or less than 10% of the food intake relative to the solvent control area, so it is effective.

(Test Example 2) Effect test on Spodoptera litura

The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. The cabbage leaves were immersed in the above dilution for 30 seconds. Put the cabbage leaf into a petri dish, and put 5 second-instar larvae of Spodoptera litura. Place the petri dish in a constant temperature room with a temperature of 25°C and a humidity of 60%. After 6 days have passed since the insects were released, the animals were judged to be alive or dead, and the insecticidal rate was calculated. The test was repeated twice.

For the compounds shown in Table 8, the efficacy test against Spodoptera litura was conducted. Each compound showed an insecticidal rate of more than 80% against Spodoptera litura.

(Test Example 3) Effect test on Plutella xylostella

The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. The cabbage leaves were immersed in the above dilution for 30 seconds. Put the cabbage leaf into a petri dish, and put 5 second-instar larvae of Plutella xylostella. Place the petri dish in a constant temperature room with a temperature of 25°C and a humidity of 60%. After 3 days have passed since the insects were released, they were judged to be alive or dead, and the insecticidal rate was calculated. The test was repeated twice.

For the compounds shown in Table 9, the efficacy test against Plutella xylostella was conducted. Shows an insecticidal rate of more than 80%.

(Test Example 4) Effect test on bean aphid

The cowpea was cultivated in a 3-inch pot, and the primary leaves were inoculated with bean aphid nymphs. The emulsion (I) was diluted with water so that the compound of the present invention became 125 ppm, and the above-mentioned dilution was spread on the cowpea parasitized by the bean aphid nymph. Place the cowpea in a constant temperature room with a temperature of 25°C and a humidity of 60%. After 4 days after spreading, the bean aphid was judged to be alive or dead, and the insecticidal rate was calculated. The test was repeated twice.

For the compounds shown in Table 10, an efficacy test against bean aphid was carried out. Each compound showed an insecticidal rate of more than 80% to bean aphid.

(Test Example 5) Efficacy Test on Bemisia tabaci

The emulsion (I) was diluted with water so that the concentration of the compound of the present invention became 125 ppm. Spread the dilution on tomato seedlings and air-dry. Put the Bemisia tabaci adults on the day of spreading and let them lay eggs. The number of parasitic larvae was counted 12 days after spreading. The effectiveness of the compound is evaluated by the control rate. The test was repeated twice.

For the compounds shown in Table 11, an efficacy test against Bemisia tabaci was carried out. The next-generation control rate of each compound is more than 80%.

(Test Example 6) Efficacy Test on Yellow Leaf Flea

Emulsion (I) was diluted with water so that the compound of the present invention became 125 ppm to prepare a test drug solution. Spread the above-mentioned dilution liquid on the green-stemmed Chinese cabbage seedlings (the seventh stage of development of natural leaves) planted in a 3-inch pot. After air-drying, the green-stemmed cabbage seedlings were put into a plastic cup, and 10 yellow striped leaf fleas (Phyllotreta striolata) adults were placed. Store in a constant temperature room with a temperature of 25°C and a humidity of 65%, After 7 days after the insects were released, they were judged to be alive or dead, and the insecticidal rate was calculated. The test was repeated twice.

For the compounds shown in Table 12, the efficacy test against adults of Yellow leaf flea was carried out. As a result, each compound showed an insecticidal rate of more than 80% against adults of yellow leaf flea.

(Test Example 7) Effect test on housefly

The compound of the present invention was diluted with acetone and dropped to 1 g of sugar cube so as to become 100 ppm. Put the sugar cube into a plastic cup, put 10 housefly female adults, and cover the lid. It was stored at 25°C, and after 24 hours had passed, the insects were judged to be alive or dead, and the insecticide rate was calculated. The test was repeated twice.

For the compounds of compound numbers 1-4, the efficacy test on the female adults of housefly was carried out. The insecticidal rate is over 80%.

(Test Example 8) Effect test on mixed house mosquitoes

Emulsion (I) was diluted with water so that the compound of the present invention became 10 ppm to prepare a test drug solution. Put 20 first-instar larvae of mixed house mosquito (Culex pipiens molestus) into 100 mL of the drug solution, and count the number of dead insects one day later to calculate the insecticidal rate. The test was repeated twice.

For the compounds shown in Table 13, the efficacy test on the first instar larvae of mixed house mosquitoes was carried out. As a result, each compound showed a 100% insecticidal rate to the first instar larvae of mixed house mosquitoes.

(Test Example 9) Effectiveness test against Spodoptera exigua (seed treatment)

Each 0.1 g of the compound of the present invention was diluted with 2 mL of acetone to prepare a test drug solution. 10g of wheat seeds were added to the above-mentioned test liquid and dried in air, and 100 seeds were sown into flower pots. After being stored in a greenhouse at 25°C for 7 days, 100 first-instar larvae of Psedaletia separate were placed in the flowerpot. Stored in a greenhouse at 25°C, after 3 days, the number of surviving Spodoptera exigua was investigated to calculate the control rate. The test was repeated twice.

For the compounds of compound numbers 1-9, the efficacy test on the first instar larvae of Spodoptera exigua was conducted. As a result, each compound showed a control rate of more than 80% against the first instar larvae of Spodoptera exigua.

(Test Example 10) Effect test on rice wheat aphid (seed treatment)

Each 0.1 g of the compound of the present invention was diluted with 2 mL of acetone to prepare a test drug solution. 10g of wheat seeds were added to the above-mentioned test liquid and dried in air, and 100 seeds were sown into flower pots. After being stored in a greenhouse at 25°C for 7 days, the pot was inoculated with 50 adult rice aphid (Rhopalosiphum padi). Six days after the inoculation, the number of surviving rice and wheat aphids parasitized was investigated, and the control rate was calculated. The test was repeated twice.

For the compounds of compound numbers 1-9, the efficacy test against rice wheat aphid was carried out. As a result, the control rate of rice and wheat aphids was over 80%.

(Experiment 11) Feeding effect test on Ornithodoros morifolium

The DMSO solution of the compound of the present invention is mixed into the decellulose blood of sheep to obtain a 10 ppm mixed solution. 2 ml of this mixed solution was added to the container and sealed with a parafilm. In addition, 20 third nymphs of Ornithodoros moubata (Ornithodoros moubata) were added and allowed to suck blood through the parafilm for about 30 minutes. The nymphs are moved to a storage container and cultivated in a constant temperature room with a temperature of 28°C and a humidity of 80%. The life and development stages of the nymphs are observed 14 days after the blood sucking. The test was repeated twice.

For the compounds of compound numbers 1-4, the feeding effect test on Ornithodoros morifolia was carried out, and the results showed an insecticidal rate of more than 90%.

(Test Example 12) Contact effect test on Rhipicephalus miniatures

The DMSO solution of the compound of the present invention was diluted with water to obtain a test drug solution of 100 ppm. The drug solution was dropped into a container containing 20 Rhipicephalus microplus larvae, and cultivated in a constant temperature room with a temperature of 28°C and a humidity of 80%. The larvae were judged to be dead or alive 24 hours after treatment with the drug. The test was repeated twice.

For the compounds of compound numbers 1-4, the contact effect test on Rhipicephalus miniature was carried out, and the results showed an insecticidal rate of more than 90%.

(Test Example 13) Contact/feeding effect test on Lucilia aeruginosa larvae

The DMSO solution of the compound of the present invention is mixed with horse meat to obtain a 1000 ppm mixture. Twenty larvae of Lucilia cuprina were introduced into the test tube together with the above mixture. The larvae were cultivated in a constant temperature room with a temperature of 28°C and a humidity of 80%, and the larvae were judged to be alive and dead 48 hours after the start of the test. The test was repeated twice.

For the compounds of compound numbers 1-4, the contact/feeding effect test on the larvae of Lucilia aeruginosa showed an insecticidal rate of more than 90%.

(Test Example 14) Contact/feeding effect test on Aegypti mosquito larvae

Dilute the DMSO solution of the compound of the present invention with water to obtain a 100 ppm dilution. 10 first-instar larvae of Aedes aegypti and feeding water were added to each well of a 96-well microtiter plate in advance, and 1/10 of the 100ppm dilution was added to test at a final concentration of 10ppm. The larvae were cultivated in a constant temperature room with a temperature of 28°C and a humidity of 80%, and the larvae were judged to be dead or alive after 48 hours of drug treatment. The test was repeated twice.

For the compounds of compound numbers 1-4, a contact/feeding effect test on the larvae of Aegypti mosquitoes was carried out, and the results showed an insecticidal rate of more than 90%.

Those randomly selected from the compounds of the present invention all exert the above-mentioned effects. It can be understood that the compounds of the present invention, including those not exemplified, have the effects of pest control, especially acaricidal and insecticidal effects. . In addition, it is understood that the compounds of the present invention are compounds that also have effects on parasites harmful to humans and animals, such as ectoparasites.

[Industrial availability]

The diarylazole compound of the present invention can prevent harmful organisms that are a problem in crops or hygiene. In particular, it can effectively control various agricultural pests and mites at a lower concentration. Furthermore, external parasites and internal parasites that harm humans and animals can be effectively prevented. Therefore, the present invention is industrially useful.

Claims (5)

A compound or a salt thereof, the compound is represented by formula (I),

[In formula (I), B ¹ and B ⁴ each independently represent a carbon atom or a nitrogen atom; B ² and B ³ each independently represent a nitrogen atom or CR ⁵ ; here, when B ¹ is a carbon atom, B ² is a nitrogen atom or CR ⁵ , B ³ and B ⁴ are nitrogen atoms; when B ¹ is a nitrogen atom, B ² is a nitrogen atom, B ³ is a nitrogen atom or CR ⁵ , and B ⁴ is a carbon atom; R ⁴ and R ⁵ each independently represent a hydrogen atom, a halogeno group, a cyano group, an unsubstituted or substituted C1-6 alkyl group, or an unsubstituted or substituted amine group; Ar represents an unsubstituted or substituted amine group; A substituted or substituted C6-10 aryl group, or an unsubstituted or substituted 5-6 membered heteroaryl group; Q is a group represented by formula (Q-1) or (Q-2);

In formulas (Q-1) and (Q-2), * represents the bonding position; R ¹ represents an unsubstituted C1~6 alkylthio group, an unsubstituted C1~6 alkylsulfinyl group, or Unsubstituted C1~6 alkylsulfonyl; in formula (Q-1), A ¹ and A ² each independently represent a carbon atom or a nitrogen atom; wherein, A ¹ and A ^{2 are} not nitrogen atoms at the same time; X Represents unsubstituted or substituted C1~6 alkyl, unsubstituted or substituted C2~6 alkenyl, unsubstituted or substituted C2~6 alkynyl, hydroxyl, unsubstituted or has Substituent C1~6 alkoxy group, methanoyl group, unsubstituted or substituted C1~6 alkylcarbonyl group, unsubstituted or substituted C1~6 alkoxycarbonyl group, mercapto group, unsubstituted Or substituted C1~6 alkylthio, unsubstituted or substituted C1~6 alkylsulfinyl, unsubstituted or substituted C1~6 alkylsulfinyl, unsubstituted Substituted or substituted aminocarbonyl, unsubstituted or substituted C3~8 cycloalkyl, unsubstituted or substituted C6~10 aryl, unsubstituted or substituted C6~10 Aryloxy group, unsubstituted or substituted 3--6 membered heterocyclyl group, unsubstituted or substituted amine group, halogen group, cyano group or nitro group; n represents the number of X , And is any integer from 0 to 4; when n is 2 or more, X may be the same or different from each other; in formula (Q-2), A ³ represents a carbon atom or a nitrogen atom; R ² and R ³ are each independently Represents hydrogen atom, unsubstituted or substituted C1-6 alkyl, unsubstituted or substituted C2-6 alkenyl, unsubstituted or substituted C2-6 alkynyl, hydroxyl, unsubstituted Substituted or substituted C1-6 alkoxy, methanoyl, unsubstituted or substituted C1-6 alkylcarbonyl, unsubstituted or substituted C1-6 alkoxycarbonyl, mercapto, Unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfinyl group , Unsubstituted or substituted aminocarbonyl, unsubstituted or substituted C3~8 cycloalkyl, unsubstituted or substituted C6~10 aryl, unsubstituted or substituted C6~10 aryloxy group, unsubstituted or substituted 3-6 membered heterocyclic group, unsubstituted or substituted amine group, halogen group, cyano group or nitro group; wherein, R ³ is hydrogen In the case of atoms, R ² is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclic group; wherein, in Ar is unsubstituted or substituted In the case of a 5-membered heteroaryl group, Q is a group represented by formula (Q-1); where Ar is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 6 When R ⁴ is an unsubstituted or substituted amine group, Q is the formula (Q -1) The group represented; where Ar is an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 6-membered heteroaryl group, and R ⁴ is an unsubstituted or substituted group In the case of substituents other than the amino group, Q is a group represented by formula (Q-2); the above-mentioned heteroaryl or heterocyclic group contains 1 selected from the group consisting of nitrogen atom, oxygen atom and sulfur atom When ~4 heteroatoms are used as the constituent atoms of the ring, the "substituent" in the above "substituent" is C1~6 alkyl, C2~6 alkenyl, C2~6 alkynyl, C3~8 cycloalkyl, C6~10 aryl, C6~10 aryl, C1~6 alkyl, 3~6 membered heterocyclic group, 3~6 membered heterocyclic group, C1~6 alkyl, hydroxyl, C1~6 alkoxy, C2~6 Alkenyloxy, C2~6 alkynyloxy, C6~10 aryloxy, C6~10 aryl, C1~6 alkoxy, 5~6 membered heteroaryloxy, 5~6 membered heteroaryl, C1~6 alkane Oxy, formyl, C1~6 alkylcarbonyl, formyloxy, C1~6 alkylcarbonyloxy, C6~10 arylcarbonyl, C1~6 alkoxycarbonyl, C1~6 alkoxycarbonyl Oxy group, carboxyl group, halogen group, C1~6 halogenated alkyl group, C2~6 halogenated alkenyl group, C2~6 halogenated alkynyl group, C1~6 halogenated alkoxy group, C2~6 halogenated alkenyloxy group, C1~6 halogenated alkane Carbonyl group, amino group, C1~6 alkyl substituted amino group, C6~10 arylamino group, C6~10 aryl group, C1~6 alkylamino group, methanoylamino group, C1~6 alkylcarbonylamino group , Single C1~6 alkoxycarbonylamino group, two C1~6 alkoxycarbonylamino group, aminocarbonyl, dimethylaminocarbonyl, phenylaminocarbonyl, N-phenyl-N-methylamine Carbonyl, imino C1~6 alkyl, N-hydroxy-iminomethyl, (1-(N-hydroxy)-imino)ethyl, (1-(N-hydroxy)-imino) ) Propyl, N-methoxy-iminomethyl, (1-(N-methoxy)-imino)ethyl, aminocarbonyloxy, C1~6 alkyl substituted aminocarbonyloxy Group, mercapto group, C1~6 alkylthio, C1~6 haloalkylthio, C6~10 arylthio, 5~6 membered heteroarylthio, C1~6 alkylsulfinyl, C1~6 Halogenated alkylsulfinyl group, C6~10 arylsulfinyl group, 5~6 membered heteroarylsulfinyl group, C1~6 alkylsulfinyl group, C1~6 halogenated alkylsulfinyl group, C6 ~10 arylsulfonyl group, 5~6 membered heteroarylsulfonyl group, C1~6 alkylsulfonyloxy group, C1~6 haloalkylsulfonyloxy group, tri-C1~6 alkyl substituted silyl group, Three C6~10 aryl substituted silyl, or cyano, nitro]. A pest control agent containing at least one selected from the group consisting of the first item of the patent application compound and the salt as an active ingredient. For example, the pest control agent of item 2 of the scope of patent application, wherein the above-mentioned pests are external parasites or internal parasites. An insecticide or acaricide containing at least one selected from the group consisting of the first item of the patent application compound and the salt as an active ingredient. An internal parasite repellent, which contains at least one selected from the group consisting of the first item of the patent application compound and the salt as an active ingredient.