JP2019006772A - Diarylazole compound and pest control agent - Google Patents

Abstract

To provide a compound and a pest control agent having insecticidal activity and/or acaricidal activity.SOLUTION: The present invention provides a compound represented by the formula or a salt thereof. (Ais N or the like; Ais CR, Ris -C(R)=N-ORor the like; Rand Rindependently represent H or a substituted or unsubstituted C1-6 alkyl group; Ris a substituted or unsubstituted C1-6 alkyl sulfonyl group; Ris -C(R)=N-ORor the like; Rand Rindependently represent H or a substituted or unsubstituted C1-6 alkyl group; Q is an aryl substituted imidazole group or aryl substituted pyrazole group or the like).SELECTED DRAWING: None

Description

  The present invention relates to a diarylazole compound and a pest control agent. More specifically, 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 a pest control agent containing the compound as an active ingredient About.

  Various compounds having insecticidal / miticidal activity have been proposed. In order to put such compounds into practical use as agricultural chemicals, they are not only sufficiently effective but also resistant to drug resistance, do not cause phytotoxicity or soil contamination on plants, and have low toxicity to livestock and fish. Etc. are required.

By the way, Patent Document 1 discloses a compound represented by the formula (A).

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

Patent Document 3 discloses a compound represented by the formula (C).

Patent Document 4 discloses a compound represented by the formula (D).

Patent Document 5 discloses a compound represented by the formula (E).

Patent Document 6 discloses a compound represented by the formula (F).

WO 2015/144895 A WO 2016/024587 A WO 2017/016922 A WO 2018/052035 A WO 2016/113155 A WO 2016/204270 A

  An object of the present invention is to provide a diarylazole compound that has excellent pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized advantageously industrially. Another object of the present invention is to provide a pest control agent, insecticide or acaricide, ectoparasite control agent, or endoparasite control or control agent containing a diarylazole compound as an active ingredient.

  In order to solve the above problems, the present invention including the following embodiments has been completed.

式(I)中、
Ａ¹は、窒素原子（Ｎ）またはＣＨである。
Ａ²は、ＣＲ²である。
Ｒ²は、水素原子、−Ｃ（Ｒ^2a）＝Ｎ−ＯＲ^2bで表される基、または−Ｃ（Ｒ^2c）＝Ｎ−ＮＲ^2dＲ^2eで表される基である。
Ｒ^2a、Ｒ^2b、Ｒ^2c、Ｒ^2dおよびＲ^2eは、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１〜６アルキル基である。
Ｒ³は、置換若しくは無置換のＣ１〜６アルキルスルホニル基である。
Ｒ⁴は、水素原子、−Ｃ（Ｒ^4a）＝Ｎ−ＯＲ^4bで表される基、または−Ｃ（Ｒ^4c）＝Ｎ−ＮＲ^4dＲ^4eで表される基である。
Ｒ^4a、Ｒ^4b、Ｒ^4c、Ｒ^4dおよびＲ^4eは、それぞれ独立して、水素原子、または置換若しくは無置換のＣ１〜６アルキル基である。
但し、Ｒ²とＲ⁴は同時に水素原子であることはない。
Ｑは、式(Q-1)または式(Q-2)で表される基である。

式(Q-1)中、
＊は結合位置である。
Ａｒは、置換若しくは無置換のＣ６〜１０アリール基、または置換若しくは無置換の５〜６員ヘテロアリール基である。
Ｒ⁵は、置換若しくは無置換のＣ１〜６アルキル基である。
Ｒ⁶は、水素原子、置換若しくは無置換のＣ１〜６アルキル基、またはハロゲノ基である。

式(Q-2)中、
＊は結合位置である。
Ａｒは、置換若しくは無置換のＣ６〜１０アリール基、または置換若しくは無置換の５〜６員ヘテロアリール基である。
Ｒ⁷は、水素原子、置換若しくは無置換のＣ１〜６アルキル基、置換若しくは無置換のＣ１〜６アルケニル基、置換若しくは無置換のＣ１〜６アルキニル基、置換若しくは無置換のアミノ基、またはハロゲノ基である。
Ｒ⁸は、水素原子、または置換若しくは無置換のＣ１〜６アルキル基である。 [1] A compound represented by the formula (I) or a salt thereof.

In formula (I),
A ¹ is a nitrogen atom (N) or CH.
A ² is CR ² .
R ² is a hydrogen atom, a group represented by —C (R ^2a ) ═N—OR ^2b , or a group represented by —C (R ^2c ) ═N—NR ^2d R ^2e .
R ^2a , R ^2b , R ^2c , R ^2d and R ^2e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
R ³ is a substituted or unsubstituted C 1-6 alkylsulfonyl group.
R ⁴ is a hydrogen atom, a group represented by —C (R ^4a ) ═N—OR ^4b , or a group represented by —C (R ^4c ) ═N—NR ^4d R ^4e .
R ^4a , R ^4b , R ^4c , R ^4d and R ^4e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
However, R ² and R ⁴ are not hydrogen atoms at the same time.
Q is a group represented by formula (Q-1) or formula (Q-2).

In formula (Q-1),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁵ is a substituted or unsubstituted C 1-6 alkyl group.
R ⁶ is a hydrogen atom, a substituted or unsubstituted C ^1-6 alkyl group, or a halogeno group.

In formula (Q-2),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁷ represents a hydrogen atom, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 1-6 alkenyl group, a substituted or unsubstituted C 1-6 alkynyl group, a substituted or unsubstituted amino group, or halogeno It is a group.
R ⁸ is a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.

[2] A pest control agent comprising at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.

[3] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.

[4] An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] and a salt thereof.

[5] An endoparasite control agent or pesticide containing, as an active ingredient, at least one selected from the group consisting of the compound according to [1] and a salt thereof.

  The diarylazole compound of the present invention can control pests that are problematic in crops and sanitation. In particular, agricultural pests and mites can be effectively controlled at a lower concentration. Furthermore, ectoparasites and endoparasites that harm human livestock can be effectively controlled.

[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).

式(Q-1)中、
＊は結合位置である。
Ａｒは、置換若しくは無置換のＣ６〜１０アリール基、または置換若しくは無置換の５〜６員ヘテロアリール基である。
Ｒ⁵は、置換若しくは無置換のＣ１〜６アルキル基である。
Ｒ⁶は、水素原子、置換若しくは無置換のＣ１〜６アルキル基、またはハロゲノ基である。

式(Q-2)中、
＊は結合位置である。
Ａｒは、置換若しくは無置換のＣ６〜１０アリール基、または置換若しくは無置換の５〜６員ヘテロアリール基である。
Ｒ⁷は、水素原子、置換若しくは無置換のＣ１〜６アルキル基、置換若しくは無置換のＣ１〜６アルケニル基、置換若しくは無置換のＣ１〜６アルキニル基、置換若しくは無置換のアミノ基、またはハロゲノ基である。
Ｒ⁸は、水素原子、または置換若しくは無置換のＣ１〜６アルキル基である。 In formula (I),
A ¹ is a nitrogen atom (N) or CH.
A ² is CR ² .
R ² is a hydrogen atom, a group represented by —C (R ^2a ) ═N—OR ^2b , or a group represented by —C (R ^2c ) ═N—NR ^2d R ^2e .
R ^2a , R ^2b , R ^2c , R ^2d and R ^2e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
R ³ is a substituted or unsubstituted C 1-6 alkylsulfonyl group.
R ⁴ is a hydrogen atom, a group represented by —C (R ^4a ) ═N—OR ^4b , or a group represented by —C (R ^4c ) ═N—NR ^4d R ^4e .
R ^4a , R ^4b , R ^4c , R ^4d and R ^4e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
However, R ² and R ⁴ are not hydrogen atoms at the same time.
Q is a group represented by formula (Q-1) or formula (Q-2).

In formula (Q-1),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁵ is a substituted or unsubstituted C 1-6 alkyl group.
R ⁶ is a hydrogen atom, a substituted or unsubstituted C ^1-6 alkyl group, or a halogeno group.

In formula (Q-2),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁷ represents a hydrogen atom, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 1-6 alkenyl group, a substituted or unsubstituted C 1-6 alkynyl group, a substituted or unsubstituted amino group, or halogeno It is a group.
R ⁸ is a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.

In the present invention, the term “unsubstituted” means only a group serving as a mother nucleus. When there is no description of “substituted” and only the name of the group serving as the mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “substituted” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group (substituent) having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. 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 of the group serving as the mother nucleus is 1-6. This 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 effects of the present invention. Examples of groups that can be “substituents” are shown below.
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cuvanyl group;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
A 3-6 membered heterocyclyl group;
A 3-6 membered heterocyclyl C1-6 alkyl group;

Hydroxyl group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
A C2-6 alkynyloxy group such as an ethynyloxy group or a propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
A C6-10 aryl C1-6 alkoxy group such as a benzyloxy group or a phenethyloxy group;
5-6 membered heteroaryloxy groups such as thiazolyloxy group, pyridyloxy group;
5-6 membered heteroaryl C1-6 alkyloxy groups such as thiazolylmethyloxy group, pyridylmethyloxy group;

Formyl group;
A C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group;
Formyloxy group;
A C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group;
A C6-10 arylcarbonyl group such as a benzoyl group;
A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group;
C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group;
Carboxyl group;

Halogeno groups such as fluoro, chloro, bromo and iodo groups;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
A C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;
A C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
A C1-6 haloalkoxy group such as a trifluoromethoxy group, a 2-chloro-n-propoxy group, or a 2,3-dichlorobutoxy group;
A C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;
A C1-6 haloalkylcarbonyl group such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group;

An amino group;
A C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, or a diethylamino group;
A C6-10 arylamino group such as an anilino group or a naphthylamino group;
A C6-10 aryl C1-6 alkylamino group such as a benzylamino group or a phenethylamino group;
Formylamino group;
A C1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group;
A C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group;
An aminocarbonyl group having no substituent or a substituent such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
N-hydroxy-iminomethyl group, (1- (N-hydroxy) -imino) ethyl group, (1- (N-hydroxy) -imino) propyl group, N-methoxy-iminomethyl group, (1- (N-methoxy) -Imino) substituted or unsubstituted N-hydroxyimino C1-6 alkyl group such as an ethyl group;
An aminocarbonyloxy group;
A C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

A mercapto group;
A C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
A C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
A C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
A 5- to 6-membered heteroarylthio group such as a thiazolylthio group or a pyridylthio group;

A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group;
A C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group or a 2,2,2-trifluoroethylsulfinyl group;
A C6-10 arylsulfinyl group such as a phenylsulfinyl group;
5-6 membered heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group;

A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group;
A C6-10 arylsulfonyl group such as a phenylsulfonyl group;
A 5- to 6-membered heteroarylsulfonyl group such as a thiazolylsulfonyl group and a pyridylsulfonyl group;
A C1-6 alkylsulfonyloxy group such as a methylsulfonyloxy group, an ethylsulfonyloxy group, or a t-butylsulfonyloxy group;
A C1-6 haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group or a 2,2,2-trifluoroethylsulfonyloxy group;

A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group;
A tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;
Cyano group; nitro group;

  In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure. In this case, examples of the “substituent” include C1-6 alkyl group, C1-6 haloalkyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, halogeno group, cyano group, nitro group and the like.

  Moreover, said "3-6 membered heterocyclyl group" contains 1-4 heteroatoms chosen from the group which consists of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring structural atom. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, if at least one ring is a hetero ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3-6 membered heterocyclyl group” include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

  Examples of the 3-6 membered saturated heterocyclyl group include an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

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

The “C1-6 alkyl group” in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e may be a straight chain or a branched chain as long as it has 3 or more carbon atoms. As the alkyl group, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group I-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Specific examples of the “C1-6 alkyl group having a substituent” in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e include
Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -Trifluoromethylethyl group, 1,1,1,3,3,3-hexafluoropropan-2-yl group, perfluoropropan-2-yl group, perfluorohexyl group, perchlorohexyl group, 2,4 A C1-6 haloalkyl group such as a 1,6-trichlorohexyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group, hydroxyethyl group;
C1-C1 such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group 6 alkoxy C1-6 alkyl groups;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
And C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group, and the like.

The substituent on the “C1-6 alkyl group” in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; C1-6 alkoxy groups such as ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2 , 3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; cyano group;

Examples of the “C1-6 alkylsulfonyl group” for R ³ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.

As a substituent on the “C 1-6 alkylsulfonyl group” in R ³ , preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group , N-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and other C1-6 alkoxy groups; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group and the like A C1-6 haloalkoxy group of cyano group;

“Substituted or unsubstituted C1-6 alkyl groups” in R ^4a , R ^4b , R ^4c , R ^4d and R ^4e are those specifically exemplified in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e . The same thing can be mentioned.

The “C6-10 aryl group” in Ar may be monocyclic or polycyclic. In the polycyclic aryl group, if at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
Examples of the “C6-10 aryl group” include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like.

Preferred substituents on the “C6-10 aryl group” in Ar include chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, A C1-6 haloalkyl group such as a fluoro-n-pentyl group; a substituted or unsubstituted C1-6 alkoxy group;
Examples of the “C1-6 alkoxy group” include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like. it can.
The substituent on the “C 1-6 alkoxy group” is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n- C1-6 alkoxy groups such as butoxy, s-butoxy, i-butoxy, and t-butoxy; C1 such as 2-chloro-n-propoxy, 2,3-dichlorobutoxy, and trifluoromethoxy A 6-haloalkoxy group; a cyano group;

  As the “5- to 6-membered heteroaryl group” in Ar, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, A 5-membered heteroaryl group such as a tetrazolyl group; and a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group can be given.

  As a substituent on the “5- to 6-membered heteroaryl group” in Ar, preferably a halogeno group such as a fluoro group, a chloro group, a bromo group, an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group , N-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group and other C1-6 alkyl groups; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl A C1-6 alkoxycarbonyl group such as a group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group; and a diC1-6 alkylcarbonylamino group such as a diacetylamino group.

Examples of the “substituted or unsubstituted C1-6 alkyl group” in R ⁵ include the same as those specifically exemplified in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e .

Examples of the “substituted or unsubstituted C1-6 alkyl group” for R ⁶ include the same as those specifically exemplified for R ^2a , R ^2b , R ^2c , R ^2d and R ^2e .

Examples of the “halogeno group” for R ⁶ include a fluoro group, a chloro group, a bromo group, and an iodo group.

Examples of the “substituted or unsubstituted C1-6 alkyl group” for R ⁷ include the same groups as those specifically exemplified for R ^2a , R ^2b , R ^2c , R ^2d and R ^2e .

As the “C1-6 alkenyl group” for R ⁷ , a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl Group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

As the “C1-6 alkynyl group” in R ⁷ , an ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl Group, 1,1-dimethyl-2-butynyl group and the like.

Preferred examples of the substituent on the “C1-6 alkenyl group” and the “C1-6 alkynyl group” in R ⁷ include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.

The “substituted or unsubstituted amino group” in R ⁷ is a group represented by “—NR ^f R ^g ”. In the formula, R ^f and R ^g are each independently a hydrogen atom, a substituted or unsubstituted C 1-6 alkyl group, a formyl group, or a substituted or unsubstituted C 1-6 alkylcarbonyl group.

Examples of the “substituted or unsubstituted C1-6 alkyl group” for R ^f and R ^g include the same as those specifically exemplified for R ^2a , R ^2b , R ^2c , R ^2d and R ^2e .

Examples of the “C1-6 alkylcarbonyl group” for R ^f and R ^g include an acetyl group and a propionyl group.

Preferred examples of the substituent on the “C1-6 alkylcarbonyl group” for R ^f and R ^g include halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodo group.

Examples of the “substituted or unsubstituted C1-6 alkyl group” in R ⁸ include the same as those specifically exemplified in R ^2a , R ^2b , R ^2c , R ^2d and R ^2e .

  The salt of compound (I) is not particularly limited as long as it is an agro-horticulturally acceptable salt. 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; alkaline earths such as calcium and magnesium A salt of a transition metal such as iron or copper; a salt of an organic base such as ammonia, triethylamine, tributylamine, pyridine or hydrazine.

  Compound (I) or a salt of compound (I) is not particularly limited by the production method. For example, the compound (I) or the salt of the compound (I) of the present invention can be obtained by a known production method described in Examples and the like. 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 controlling pests such as various agricultural pests and mites that affect plant growth.
Further, the diarylazole compound of the present invention is a highly safe substance because it has little phytotoxicity to crops and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or an acaricide.
Furthermore, in recent years, resistance to various existing drugs has been developed in many pests such as moths, leafhoppers, leafhoppers, and aphids, resulting in problems of insufficient efficacy of these drugs. ing. The diarylazole compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on various resistant strains of insects and further on acaricide-resistant strains of mites.

  The diarylazole compound of the present invention is excellent in the effect of controlling ectoparasites and endoparasites that are harmful to humans and animals. In addition, it is a highly safe substance because of its low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an ectoparasite and endoparasite control agent.

  In addition, the diarylazole compound of the present invention is effective at all stages of development of organisms to be controlled, and has an excellent control effect on, for example, eggs, nymphs, larvae, pupae and adults such as mites and insects. Show.

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

The pest control agent or insecticide or acaricide of the present invention includes cereals, vegetables, root vegetables, potatoes, flowering plants, fruit trees, foliage plants, trees such as tea, coffee, cacao, grasses, etc. Turf; preferably used for plants such as cotton.
In application to plants, the pest control agent or insecticide or acaricide of the present invention may be any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, etc. It may be used for these parts.
Moreover, the pest control agent or insecticide or acaricide of the present invention is not particularly limited depending on the species of plant to be applied. Examples of plant seeds include original species, varieties, improved varieties, cultivars, mutants, hybrids, and genetically modified organisms (GMO).

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

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

(1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(B) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella;
(C) Carposinidae, for example, Carposina sasakii;
(D) moths of the family Craambidae, for example Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp. , Ostrinia furnacalis, European corn borer (Ostrinia nubilalis), Azuchi no moth (Ostrinia scapulalis); Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella;
(E) Gelechiidae moths such as Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella;
(F) Geometridae moths, for example Ascotis selenaria;
(G) moths of the family Gracillariidae, such as, for example, Caloptilia theivora, citrus leafworm (Phyllocnistis citrella), phleglonorycter ringoniella;
(H) Hesperiidae butterflies such as Parnara guttata;
(I) moths of the Lasiocampidae family, for example, Malocasoma neustria;
(J) moths from the Lymantriidae family, for example, Lymantria spp., Lymantria dispar, Lymantria monacha; other, Euproctis pseudoconspersa, Orgyia sp. thyellina);

(K) moths of the family Lyonetiidae, for example, Lyonetia clerkella, Lyonetia prunifoliella malinella, from the genus Lyonetia spp .;
(L) Noctuidae moths, for example, Spodoptera spp., Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Spodoptera exigua ), African Spodoptera littoralis, Spodoptera litura; eg, Autographa spp., Autographa gamma, Autographa nigrisigna; eg, Agrotisp. For example, Agrotis ipsilon, Agrotis segetum; for example, Helicoverpa spp., Helicoverpa armigera, Tobacco moth (Helicoverpa assulta), Cotton ball worm (Helicoverpa zea); Of the seed (Heliothis spp.) (Heliothis armigera), fake American tobacco (Heliothis virescens); other, Aedia leucomelas; (Naranga aenescens), Pinola japonica, Peridroma saucia, Soybean looper (Pseudoplusia includens), Trichoplusia ni;
(M) Nolidae moths such as Misaria olinga (Earias insulana);
(N) Pieridae butterflies, for example, Pieris sp., Pieris brassicae, Pieris rapae crucivora;
(O) moths of the family Plutellidae, for example, Acrolepiopsis sapporensis, Acrolepiopsis suzukiella of Acrolepiopsis spp .; Others, Plutella xylostella;
(P) Pyralidae moths, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Galleria mellonella;
(Q) Sphingidae moths, for example, Manduca quinquemaculata, Manduca sexta of Manduca spp .;

(R) moths from the family Stahmopodidae, for example, Stahmopoda masinissa;
(S) moths of the family Tineidae, for example, tiger (Tinea translucens);
(T) Tortricidae moths, for example, Adoxophyes honmai, Adoxophyes orana of Adoxophyes spp .; for example, Archips spp. ), Apple chips (Archips breviplicanus), green chips leaf (Archips fuscocupreanus); ), Chamonaki (Homona magnanima), Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Spiananothis pill;
(U) Yponomeutidae moth, for example, Argyresthia conjugella.

(2) Thysanoptera pests (a) from the Phlaeothripidae, for example, Ponticulothrips diospyrosi;
(B) From the Thripidae family, for example, from Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; Thrips palmi, Thrips tabaci; Others, Croton thrips (Heliothrips haemorrhoidalis), Scirtothrips dorsalis.

(3) Hemiptera pests (A) Ceratomas (Archaeorrhyncha)
(A) From the Delphacidae, for example, Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, Sogatella furcifera.

(B) Clypeorrhyncha
(A) From the family of Cicadellidae, for example, from the Empoasca spp., The Empoasca fabae, the Empoasca nipponica, the Empoasca onukii, the legume Emporasca sakaii, other, butterfly (Arboridia apicalis), green leafhopper (Balclutha saltuella), leafhopper leafhopper (Epiacanthus stramineus), leafhopper leafhopper (Macrosteles striifrons), nectar hot eps ).

(C) Stink bug (Heteroptera)
(A) from the family Alydidae, for example, Riptortus clavatus;
(B) From the family Coridae, for example, Cletus punctiger, Leptocorisa chinensis;
(C) From the family of the family Lygaeidae (Lygaeidae), for example
leucopterus), Cavelerius saccharivorus, Togo hemipterus;
(D) From the Miridae family, for example, the black turtle (Halticus insularis), the white turtle (Lygus lineolaris), the cotton-free hopper (Psuedatomoscelis seriatus), the stag beetle (Stenodema sibiricum), the stag moth ru ), Trigonotylus caelestialium;

(E) from the Pentatomidae family, for example, from the Nezara spp., Nezara antennata, Nezara viridula; , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, Others, Dolycoris baccarum, Eurydema rugous sword Halyomorpha halys), Piezodorus hybneri, Plautia crossota, Scotinophora lurida;
(F) from the family Pyrrhocoridae, for example, Dysdercus cingulatus;
(G) from the family Rhopalidae, for example, Rhopalus msculatus;
(H) From the family Scutelleridae, for example, Eurygaster
integriceps);
(I) From the Tingidae family, for example, Stephanitis nashi.

(D) Sternorrhyncha
(A) from the family Adelgidae, for example, Adelges laricis;
(B) Aleyrodidae, for example, Bemisia spp., Silver leaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Others, Aleurocanthus spiniferus, citri), Trialeurodes vaporariorum;
(C) Aphididae, for example, from Aphis spp., Aphis craccivora, bean aphid (Aphis fabae), strawberry aphid (Aphis forbesi), cotton aphid (Aphis gossypii) , European apple aphids (Aphis pomi), elder-core aphids (Aphis sambuci), Aphis spiraecola; for example, Rhopalosiphum spp., Corn aphids (Rhopalosiphum maidis), hum For example, Dysaphis plantaginea, Dysaphis radicola of Dysaphis spp .; for example, Macrosiphum avenae, Macrosiphum avenae, Aphid (Macrosiphum euphorbiae); For example, from the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; Other, Acyrthosiphon pisum, potato beetle Aphids (Aulacorthum solani), wheat aphids (Brachycaudus helichrysi), radish aphids (Brevicoryne brassicae), strawberry aphids (Chaetosiphon fragaefolii), peach aphids (Hyalopteruc prae) Lipaphis erysimi, broad bean aphid (Megoura viciae), barley aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hops aphid (Phorodon humuli), barley aphid (Schizaphis graminum), wheat aphid (Sitobion avenae), rice aphid (Toxoptera aurantii);

(D) from the family of Coccidae, for example, Ceroplastes ceriferus, Ceroplastes rubens of the genus Ceroplastes spp .;
(E) Pseudaulacaspis pentagona, Pseudaulacaspis prunicola of Pseudaulacaspis spp. From the family Diaspididae; for example, Unaspisp. , Unaspis euonymi, Unaspis yanonensis; Others, Aonidiella aurantii, Comstockaspis perniciosa, Fiorinia theoni dia, Poriomae );
(F) from the order of the Margarodidae family, for example, Drosicha corpulenta, Icerya purchasi;
(G) from the family Aphididae (Phylloxeridae), for example, grape aphids (Viteus vitifolii);
(H) From the Pseudococcidae family, for example, from Planococcus spp., Planococcus citri, Planococcus kuraunhiae; other, Phenacoccus sol , Pseudococcus comstocki;
(I) From the Psyllidae family, for example Psylla mali, Psylla malis, Psylla pyrisuga; other, Diaphorina citri.

(4) Polyphaga pests (a) from the family Anobiidae, for example, the tobacco beetle (Lasioderma serricorne);
(B) From the Attelabidae family, for example, Byctiscus betulae, Rhynchites heros;
(C) from the family Bostrichidae, for example, Lyctus brunneus;
(D) from the Brentidae family, for example, Cylas formicarius;
(E) from the Buprestidae family, for example, Agrilus sinuatus;
(F) From the Cerambycidae family, for example, Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, Xylotrechus pyrrhoder;
(G) From the Chrysomelidae family, for example, the Bruchus spp., The pea weevil (Bruchus pisorum), the broad beetle (Bruchus rufimanus); for example, the northern corn of the Diabrotica spp. Rootworm (Diabrotica barberi), Southern corn rootworm (Diabrotica undecimpunctata), Western corn rootworm (Diabrotica virgifera); for example, Phyllotreta nemorum, Phyllotreta nemorum, Phyllotreta nemorum ); Others, Aulicophora femoralis, Adzuki beetle (Callosobruchus chinensis), Tortoise beetle (Cassida nebulosa), Tentobi beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), Nekubihoso yzae (Oule) Nagasnetobiham Psylliodes angusticollis;

(H) from the species of the Coccinellidae, for example, Epilachna varivestis, Epilachna vigintioctopunctata, from the genus Epilachna spp .;
(I) from the family Curculionidae, for example, Anthonomus spp., Anthonomus grandis, Anthonomus pomorum; eg, Sitophilus spp. , Granary weevil (Sitophilus granarius), weevil (Sitophilus zeamais); other, weevil (Echinocnemus squameus), weevil (Euscepes postfasciatus), pine weevil (Hylobius abietis), alfalfa weevil (Hylobius abietis) Lissohoptrus oryzophilus, horned weevil (Otiorhynchus sulcatus), red-footed weevil (Sitona lineatus), Sphenophorus venatus;
(J) from the family Elateridae, for example, Melanotus fortnumi, Melanonotus tamsuyensis, from the genus Melanotus spp .;
(K) from the family Nitidulidae, for example, Epuraea domina;
(L) From the family Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Other, Cetonia aurata, Coretis ), Heptophylla picea, Melonlontha melolontha, Popillia japonica;
(M) from the Scolytidae family, for example, Ips typographus;
(N) from the family Staphylinidae, for example, Paederus fuscipes;
(O) from the family Tenebrionidae, for example, Tenebrio molitor, Tribolium castaneum;
(P) From the family Trogossitidae, for example, Tenebroides mauritanicus.

(5) Flies (Diptera) Pests (A) Brachycera
(A) From the family Agromyzidae, for example, of the genus Liriomyza spp., Liriomyza bryoniae, Liriomyza chinensis, Liriomyza sativae, Liriomyza sativae, Liriomyza sativae, Liriomyza Others, Chromatomyia horticola, Agromyza oryzae;
(B) from the family Anthomyiidae, for example, Delia spp., Delia platura, Cabbage fly (Delia radicum); Other, Pegomya cunicularia;
(C) Drosophila suzukii from the Drosophilidae family, for example, from Drosophila spp., Drosophila melanogaster, Drosophila suzukii;
(D) from the Ephydridae family, for example, Hydrellia griseola;
(E) from the family Psilidae, for example, Psila rosae;
(F) Tephritidae, for example, Bactrocera cucurbitae, Bactrocera dorsalis; for example, Rhagoletis spp. Rhagoletis cerasi), Rhagoletis pomonella; Others, Ceratitis capitata, Olive fruit fly (Dacus oleae).

(B) Nematocera
(A) From the family Cecidomyiidae, for example, the soybean fly (Asphondylia yushimai), the sorghum fly (Contarinia sorghicola), the fly fly (Mayetiola destructor), the squirrel fly fly (Sitodiplosis mosellana).

(6) Orthoptera pests (a) Acrididae, for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; Australian flying grasshopper (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), Tosama locust (Locusta migratoria), Brown locust (Locustana pardalina), Red locust (Nomadacris septemfasciata), Cobaneago (Oxya yezoensis)
(B) From the cricket family (Gryllidae), eg, European cricket (Acheta domestica), Teleogryllus emma;
(C) from the family Gryllotalpidae, for example, Gryllotalpa orientalis;
(D) From the Tettigoniidae family, for example, Tachycines asynamorus.

(7) Tick (Acari)
(A) Astigmata (Acaridida)
(A) Acaridae mites, for example, Rhizoglyphus echinopus, Rhizoglyphus echinipus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acetus tuna (Acarusus phlegm), Acet

(B) Prostigmata mite (Actinedida)
(A) Mites of Tetranychidae, for example, Bryobia spp., Clover spider mite (Bryobia praetiosa), Fowl spider mite (Bryobia rubrioculus); Of the spider mite (Eotetranychus kankitus), tick (Eotetranychus asiaticus), tick (Eotetranychus kantis) (Eotetranychus smithi), Sugimen spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); for example, Oligonis spp. Ma Spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), spider mite (Oligonychus spp. , Citrus spider mite (Panonychus citri), swan spider mite (Panonychus mori), apple spider mite (Panonychus ulmi); , Tetranychus quercivorus, Tetranychus phaselus, Tetranychus urticae, Tetranychus viennensis; for example, Aponychus spp. For example, the spider mite (Aponychus firmianae); for example, Sasanychus spp. ), Sponge spider mite (Shizotetranychus longus), Shizotetranychus miscanthi, Shizotetranychus schizopus, Others, Tetella spp sapporensis);

(B) Tenuipalpidae ticks, for example, Brevipalpus spp. From Brevipalpus spi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus), brevipalpus californicus; for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other, pineapple chony tick (Doli)
(C) Mites of the family Eriophyidae, for example, Aceria spos., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Rust mites (Aceria paradianthi), Black mite mites (Aceria tiyingi), Tulip mite (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp. emarginatae); eg, Aculops spp., Aculops lycopersici, Aculops pelekassi; eg, Aculus spp., Aculus fockeui, Aculus fockeui schlechtendali); Others, Acaphyll a theavagrans, Calacarus carinatus, Grape's spider mite (Colomerus vitis), Grape's spider mite (Calepitrimerus vitis), Pterosarid mite (Epitrimerus pyri), Antarctic spider mite (Paraphytoptus kikus), Maxi spider mite (Paracalacarus podocarta) citri);
(D) Tick of the family Miteaceae (Transonemidae), for example, Tarsonemus bilobatus, Tarsonemus waitei of Tarsonemus spp .; );
(E) Penthaleidae mites, for example, Penthaleus erythrocephalus, Penthaleus major of Penthaleus spp.

The pest control agent of the present invention includes other active ingredients such as fungicides, insecticides / acaricides, nematicides, soil pesticides; plant regulators, synergists, fertilizers, soil improvers, animal use It may be mixed or used together with feed.
The combination of the diarylazole compound of the present invention and other active ingredients can be expected to have a synergistic effect on insecticidal / miticidal / nematicidal activity. The synergistic effect can be confirmed by Colby's formula (Colby. SR; Calculating Synergistic and Antagonistic Responses of Herbicide Combinations; Weeds 15, pp. 20-22, 1967) according to a standard method.

  Specific examples of insecticides / acaricides, nematicides, soil insecticides, insecticides and the like that can be used in combination or in combination with the pest control agents of the present invention are shown below.

(1) Acetylcholinesterase inhibitor:
(A) Carbamate series: Alanicarb, Aldicarb, Bengiocarb, Benfuracarb, Butcarboxyme, Butoxycarboxyme, Carbaryl, Carbofuran, Carbosulfan, Ethiophenecarb, Fenobucarb, Formethanate, Furatiocarb, Isoprocarb, Methiocarb, Mesomil, Oxamyl, Pirimicarb, Propoxycarb Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb; phenothiocarb, MIPC, MPMC, MTMC, aldoxicarb, alixicarb, aminocarb, bufencarb, cloetocarb, metam sodium, promecarb;

(B) Organophosphorus: Acephate, azamethiphos, azinephos-ethyl, azinephos-methyl, kazusafos, chlorethoxyphos, chlorfenvinphos, chlormefos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, Dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethione, etoprophos, famfur, phenamiphos, fenitrothion, fenthion, phostiazet, heptenophos, imisiaphos, isofenphos, isocarbophos, isoxathione, malathione, methalmethione, mecarbamethione Monocrotophos, nared, ometoate, oxydimethone-methyl, parathion, parathion-methyl, fento , Folate, hosalon, phosmet, phosphamidone, phoxime, pyrimiphos-methyl, propenophos, propetamphos, prothiophos, pyracrofos, pyridafenthion, quinalphos, sulfotep, tebupyrine phos, temefos, terbufos, tetrachlorbinphos, thiomethone, triazophos, trichlorfos, bamidthione; Bromophos-ethyl, BRP, carbophenothione, cyanophenphos, CYAP, demeton-S-methylsulfone, diariphos, diclofenthion, dioxabenzophos, etrimphos, phensulfothione, flupyrazophos, phonophos, formothione, phosmethylan, isazophos, iodofenphos, Methacrifos, pyrimifos-ethyl, phosphocarb, propaphos, protoate, sulprophos.

(2) GABA-agonist chloride channel antagonists: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprole, pyriprole; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: Acrinatrin, d-cis-trans allethrin, d-transarethrin, bifenthrin, bioareslin, bioareslin isomers, violesmethrin, cycloprotorin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, ciphenothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R) -isomer], esfenvalerate, etofenprox, fenpropatoline, fenvalerate, flucitrinate, flumethrin, tau-fulvalinate, halfenprox, imi Ritrin, cadreslin, permethrin, phenothrin [(1R) -trans isomer], praretrin, pyrethrum, resmethrin, silafluophene, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin; allethrin, pyrethrin, pyrethrin I, Pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, fulbrocitrinate, flufenprox, methfluthrin, protrifenbut, pyrethmethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxafurol, nicotine, flupiradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulator: spinetoram, spinosad.
(6) Chloride channel activator: abamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin.
(7) Juvenile hormone-like substance: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen;
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, and tartar.
(9) Homoptera selective feeding inhibitor: flonicamid, pymetrozine, pyrifluquinazone.

(10) Tick growth inhibitor: clofentezin, diflovidazine, hexythiazox, etoxazole.
(11) Microbial-derived insect midgut mesentery: Bacillus thuringiensis subsp. Isla elensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Aisawai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutasine oxide, propargite, tetradiphone.
(13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulframide, DNOC; binapacryl, dinobutone, dinocup.
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam.
(15) Chitin synthesis inhibitor: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novallon, nobiflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
(16) Diptera molting agent: cyromazine.
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonist: amitraz, demiditraz, chlordimeform.
(19) Mitochondrial electron transport system complex III inhibitor: acequinosyl, fluacrylpyrim, hydramethylnon.
(20) Mitochondrial electron transport system complex I inhibitor: phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.

(21) Voltage-gated sodium channel blocker: indoxacarb, metaflumizone.
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat.
(23) Mitochondrial electron transport complex IV inhibitor: Aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport system complex II inhibitor: Sienopyrafen, cyflumetofene, piflummid.
(25) Ryanodine receptor modulator: chlorantraniliprole, cyantraniprole, fulvendiamide, cyclaniliprol, tetraniprolol.
(26) Mixed function oxidase inhibitor compound: Piperonyl butoxide.
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (unknown mechanism of action): azadirachtin, benzoxymate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicofol, pyridalyl; bencrothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP , Phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, fentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasul, trialacene; afidopyropen), flometokin, flufiprole, fluenesulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, me Luneodecanamide; fluralanel, afoxolanel, floxamethamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoromethyl-4,5-dihydroisoxazol-3-yl] -2- (1H-1,2, , 4-Triazol-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide and other metadiamides.

(29) Anthelmintic:
(A) benzimidazole series: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, fulbendazole; fevantel, netobimine, thiophanate; thiabendazole, canbendazole;
(B) salicylanilide series: closantel, oxyclozanide, rafoxanide, niclosamide;
(C) substituted phenols: nitroxinyl, nitroskanate;
(D) Pyrimidine series: Pirantel, Morantel;
(E) imidazothiazole series: levamisole, tetramisol;
(F) Tetrahydropyrimidine series: praziquantel, epsiprantel;
(G) Other anthelmintic drugs: cyclodiene, riania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, melolsamine, arsenamide.

Specific examples of the bactericides that can be used in combination or in combination with the pest control agent of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race;
(B) adenosine deaminase inhibitor: bupilimate, dimethylylmol, ethylimol;
(C) DNA / RNA synthesis inhibitors: Himexazole, octirinone;
(D) DNA topoisomerase II inhibitor: Oxophosphate.

(2) Mitotic fission inhibitor and cell division inhibitor:
(A) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; dietofencarb; zoxamide; ethaboxam;
(B) Cell division inhibitor: Penciclone;
(C) Delocalization inhibitor of spectrin-like protein: fluopicolide.

(3) Respiratory inhibitor:
(A) Complex I NADH oxidoreductase inhibitor: diflumetrim; tolfenpyrad;
(B) Complex II succinate dehydrogenase inhibitors: benodanyl, flutolanil, mepronil; isophetamide; fluopyram; fenfram, flumecyclox; , Furametopyr, isopyrazam, penflufen, penthiopyrad, sedaxane; boscalid;
(C) Complex III ubiquinol oxidase Qo inhibitor: azoxystrobin, cumoxystrobin, cumethoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyroxystrobin; Piramethostrobin, triclopyricarb; Cresoxime-methyl, trifloxystrobin; Dimoxystrobin, Phenaminestrobin, Metominostrobin, Orisastrobin; Famoxadone; Fluoxastrobin; Fenamidon;
(D) Complex III ubiquinol reductase Qi inhibitor: cyazofamide; amisulbrom;
(E) Uncoupler of oxidative phosphorylation: Binapacryl, meptyldinocup, dinocup; fluazinam; ferrimzone;
(F) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(G) ATP production inhibitor: silthiofam;
(H) Complex III: Cyclochrome bc1 (ubiquinone reductase) Qx (unknown) inhibitor: Amethoctrazine.

(4) Amino acid and protein synthesis inhibitors (a) Methionine biosynthesis inhibitors: Andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(B) Protein synthesis inhibitor: blasticidin-S; kasugamycin, kasugamycin hydrochloride; streptomycin; oxytetracycline.

(5) Signaling inhibitor:
(A) Signaling inhibitor: quinoxyphene, proquinazide;
(B) MAP / histidine kinase inhibitor in osmotic signal transduction: fenpiclonil, fludioxonil; clozolimate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyltransferase inhibitor: Edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole;
(C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb;
(D) Microorganisms that disturb the cell membrane of pathogenic bacteria: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(E) Agent that disturbs the cell membrane: An extract of Goseika Yupte (Tea Tree).

(7) Cell membrane sterol biosynthesis inhibitors:
(A) Demethylation inhibitor at the C14 position in sterol biosynthesis: Trifolin; Triflumizole, biniconazole;
Azaconazole, viteltanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriazole), fluconazole, fluconazole- Cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, quinconazole, cimeconazole, tebuconazole, tetraconazole, triadimethone, triadimenol, triticonazole; prothioconazole, voriconazole;
(B) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidin, piperalin; spiroxamine;
(C) 3-keto reductase inhibitor in C4-demethylation of sterol biosynthesis system: phenhexamide; fenpyrazamine;
(D) Sterol biosynthetic squalene epoxidase inhibitors: Pyributicarb; Naftifen, Terbinafine.

(8) Cell wall synthesis inhibition (a) Trehalase inhibitor: Validamycin;
(B) chitin synthase inhibitor: polyoxin, polyoxolim;
(C) Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph; benavalicarb, iprovaricarb, toluprocarb, varifenalate; mandipropamide.

(9) Melanin biosynthesis inhibitor (a) Reductase inhibitor of melanin biosynthesis: Fusaride; Pyroxylone; Tricyclazole;
(B) Dehydrase inhibitor of melanin biosynthesis: carpropamide; diclocimet; phenoxanyl.

(10) Host plant resistance inducer:
(A) Agents acting on the salicylic acid synthesis pathway: Acibenzoral-S-methyl;
(B) Other: Probenazole; thiazinyl; isotianil; laminarin;

(11) Agents whose activity is unknown: Simoxanyl, fosetyl aluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodin, dodin free base, fluthianyl.

(12) Agents with multiple action points: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; farbum, mancozeb, maneb) , Mankappa, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dichlorfluanide, tolylfluanid; guazatine, iminoctadine triacetate, iminoctadine albecate ( iminoctadine trialbesilate); anilazine; dithianon; quinomethionate;

(13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methyl isothiocyanate (MITC ), Mildeomycin, Capsaicin, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Diphenzoquat, Diphenzoquat methylsulfonate, Flumetober, Focetyl calcium, Focetyl sodium, Irumamycin, Natamycin, Nitrotal isopropyl , Oxamocarb, sodium propamocin, pyrrolnitrin, tebufloquine, torniphanide, zaliramide, Algophase, amicarthiazole (Amicarthiazol), oxathia Piperoline (Oxathiapiprolin), methylam zinc, benazole, trichramide, uniconazole, mildeomycin, oxyfentiin (Oxyfenthiin), picarbutrazox (picarbutrazox).

Specific examples of plant regulators that can be used in combination or in combination with the pest control agent of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenothiol, 1 -Naphtylacetamide, Ethiclozate, Cloxiphonac, Maleic acid hydrazide, 2,3,5-Triiodobenzoic acid, Salicylic acid, Methyl salicylate, (-)-Jasmonic acid, Methyl jasmonate, (+)-Strigol, (+) -Deo Cysts Rigoru, (+) - Orobankoru, (+) - Sorugorakuton, 4-oxo-4- (2-phenylethyl) amino acid; ethephon, chlormequat, mepiquat chloride, benzyl adenine, 5-aminolevulinic acid.

[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 amount of the diarylazole compound contained in the ectoparasite control agent of the present invention is not particularly limited as long as it exhibits an ectoparasite control effect.

  Examples of host animals to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; domestic animals such as cows, horses, pigs and sheep; warm-blooded animals such as poultry; be able to. Other examples include bees, stag beetles, and beetles.

  The ectoparasite control agent of the present invention can be applied by a known veterinary technique (topical, oral, parenteral or subcutaneous administration). As the method, it is administered orally to animals by tablet, capsule, feed mixing, etc .; it is administered to animals by immersion liquid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc .; kneading an ectoparasite-controlling agent into a resin, shaping the kneaded product into an appropriate shape such as a collar or ear tag, and applying it to an animal A method of wearing and administering locally; and the like.

  Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, it infests the back, underarms, lower abdomen, and inner crotch of the host animal and obtains nutrients such as blood and dandruff from the animal. Examples of ectoparasites include ticks, lice, fleas, mosquitoes, flies, and flyflies. Specific examples of ectoparasites that can be controlled by the ectoparasite control agent of the present invention are shown below.

(1) Tick (Acari)
Dermanyssidae ticks, Macronyssidae ticks, Laelapidae ticks, Varroidae ticks, Argasidae ticks, Ixodidae ticks, cucumber genus mite Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae mites, Trombiculidae mites, stag beetles and other parasitic insect mites .
(2) Phythiraptera
Haematopinidae lice, Linognathidae lice, Mennoponidae lice, Philopteridae lice, Trichodectidae lice
(3) Flea eyes (Siphonaptera)
Pulicidae fleas, for example, Ctenocephalides canis, Ctenocephalides felis of Ctenocephalides spp .;
Fleas from the family Tungidae, fleas from the Ceratophyllidae family, and fleas from the Leptopsyllidae family.
(4) Hemiptera.
(5) Diptera mosquitoes of Culicidae, Simuliidae mosquitoes, Ceratopogonidae mosquitoes, Tabanidae abu, Muscidae flies, Glossinidae shave flies, moss flies, hippoboscidae flies, Calliphoridae flies, Oestridae flies.

[Internal parasite control or control agent]
The endoparasite control or control agent of the present invention contains at least one selected from the diarylazole compounds of the present invention as an active ingredient. The amount of the diarylazole compound contained in the endoparasite control or pesticide of the present invention is not particularly limited as long as it exhibits an endoparasite control effect.

  Parasites that are targets of the endoparasite control or pesticide of the present invention parasitize in host animals, particularly warm-blooded animals and fish (endoparasites). Examples of host animals in which the endoparasite control or control agent of the present invention is effective include humans, livestock mammals (eg, cows, horses, pigs, sheep, goats, etc.), laboratory animals (eg, mice, rats, gerbils, etc.). , Pets (eg, hamsters, guinea pigs, dogs, cats, horses, squirrels, rabbits, ferrets, etc.), wild and zoo mammals (monkeys, foxes, deer, buffalos, etc.), poultry (turkeys, ducks, chickens, quails) , Geese, etc.), warm-blooded animals such as pet birds (eggs, parrots, nine-birds, wild birds, parakeets, juvenile pine, canaries, etc.); or fishes such as salmon, trout, swordfish. By controlling and controlling the parasite, it is possible to prevent or treat a parasitic disease mediated by the parasite.

Examples of parasites to be controlled or controlled include the following.
(1) Nematodes of the order of Dioctophymatida (a) Nematodes of the family Dioctophymatidae, for example, Dioctophyma spp.
(B) Nematodes of the Soboliphymatidae family, for example, Soboliphyme abei, Soboliphyme baturini from the species of the genus Soboliphyme spp.

(2) Trichocephalida nematodes (a) Trichinellidae trichinella, for example, Trichinella spp. Trichinella spiralis;
(B) Trichuridae trichinella, for example Capillaria spp., Capillaria annulata, Capillaria contorta, hepatic trichomes (Capillaria spp.) Capillaria hepatica, Capillaria perforans, Capillaria plica, Capillaria suis; Trichuris spp., Trichuris vulpis, cattle Trichuris discolor, Trichuris ovis, Trichuris skrjabini, Trichuris suis.

(3) Rhabditida nematodes: Strongyloides spp., For example, Strongyloides papillosus, cat feces from Strongyloides spp. Strongyloides planiceps, Strongyloides ransomi, Strongyloides suis, Strongyloides stercoralis, Strongyloides tumefaciens, Strongyloides ratti .

(4) Strongylida nematodes: Ancylostomatidae worms, for example, Ancylostoma braziliense, Ancylostoma caninum, Zubini worms of the genus Ancylostoma spp. (Ancylostoma duodenale), cat helminth (Ancylostoma tubaeforme); Uncinaria stenocephala; Uncinaria stenocephala; Bunostomum spp. Bunostomum trigonocephalum).

(5) Strongylida nematodes (a) Nematodes of the Angiostrongylidae family, for example, Aelurostrongylus abstrusus, of the genus Aelurostrongylus spp. From the genus Angiostrongylus spp., Angiostrongylus vasorum, Angiostrongylus cantonesis;
(B) Crenosomatidae nematodes, for example, Crenosoma aerophila, Crenosoma vulpis of Crenosoma spp .;
(C) Nematodes of the family Filaroididae, for example, Filaroides hirthi, Filaroides osthori (Filaroides spp.)
osleri);
(D) Pneumonia from the family Phyllidae (Metastrongylidae), for example, Metastrongylus aprius, Metastrongylus asymmetricus, Metastrongylus asymmetricus, Metastrongylus asymmetricus (Metastrongylus spp.) Metastrongylus pudendotectus), Metastrongylus salmi;
(E) Kaigamiworms of the Syngamidae family, for example, Cyathostoma bronchialis of the genus Cyathostoma spp .; Scurijabin worms of the genus Syngamus spp. Syngamus skrjabinomorpha), chicken worm (Syngamus trachea).

(6) Nematodes of Strongylida (a) Nematodes of the family Molineidae, for example, Nematodirus filicollis, Nematodirus filicollis of Nematodirus spp. Tigger (Nematodirus spathiger);
(B) Nematodes of the Dictyocaulidae family, for example, Dictyocaulus spp., Dictyocaulus filaria, Bovine pneumoniae (Dictyocaulus viviparus);
(C) Haemonchidae nematodes, for example, Haemonchus contortus from Haemonchus spp .; Cattle tortoises from Mecistocirrus spp. (Mecistocirrus digitatus);
(D) Haemonchidae nematodes, for example, Ostertagia ostertagi from the genus Ostertagia spp .;
(E) Nematodes of the family Heligmonellidae, for example Nippostrongylus braziliensis, of the genus Nippostrongylus spp .;
(F) Trichostrongylidae nematodes, for example, Trichostrongylus axei, Trichostrongylus colubriformis of the genus Trichostrongylus spp. ), Trichostrongylus tenuis; Hyostrongylus spp., Hyostrongylus rubidus; Obeliscoides spp., Obeliscoides cuniculi ).

(7) Strongylida nematodes (a) Nematodes of the Chabertiidae family, for example, Shabertia spp., Chabertia ovina; Intestinal nodules From the genus Oesophagostomum spp., Oesophagostomum brevicaudatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum dentatum, Oesophagostomum spp. Oesophagostomum maplestonei, Oesophagostomum quadrispinulatum, Oesophagostomum radiatum, Oesophagostomum venulosum, Oesophanastomum (Oeswat)
(B) Nematodes of Stephanuridae, for example, Stephanurus dentatus of Stephanurus spp .;
(C) C. elegans (Strongylidae), for example, the species of the genus C. elegans (Strongylus spp.), D. e. , Common roundworm (Strongylus vulgaris).

(8) Oxyurida nematodes Oxyuridae nematodes, for example, Enterobius anthropopitheci, Enterobius vermicularis; Oxyuris of Enterobius spp. spp.), Oxyuris equi; Passalurus spp., Rabbit worm (Passalurus ambiguus).

(9) Ascaridida nematodes (a) Nematodes of Ascaridiidae, for example, Ascaridia galli from Ascaridia spp .;
(B) Heterakidae nematodes, such as Heterakis beramporia, Heterakis brevispiculum, Heterakis gallinarum of the genus Heterakis spp. , Heterakis pusilla, Heterakis putaustralis;
(C) Anisakidae nematodes, for example, Anisakis simplex from the genus Anisakis spp .;
(D) Ascarididae nematodes, eg, Ascaris spp., Ascaris lumbricoides, Ascaris suum; Parascaris spp., Ascaris (Parascaris equorum);
(E) Toxocaridae nematodes, for example, Toxocara spp., Toxocara canis, Toxocara leonina, Toxocarasum, Toxocara vitulorum ), Toxocara cati.

(10) Spirurida nematodes (a) Onchocercidae nematodes, for example, Brugia spp., Brugia malayi, Brugia pahangi (Brugia pahangi), Brugia patei; Dipetalonema reconditum of Dipetalonema spp .; Dirofilaria spp., Dirofilaria spp. immitis); Filaria spp., Filaria oculi; Onchocerca spp., Onchocerca cervicalis, Gibson filamentous (Onchocerca gibsoni), Pharyngeal Insect (Onchocerca gutturosa);
(B) Cetaceae (Setariidae) nematodes, for example, Setaria spp., Setaria digitata, Horseworm (Setaria equina), Lipid papillary (Setaria labiatopapillosa) , Setaria marshalli; from Wuchereria spp., Wuchereria bancrofti;
(C) Nematodes of Filariidae, for example, Parafilaria spp., Parafilaria multipapillosa; Stephanofilaria spp., Stephanofilaria spum. Stephanofilaria assamensis, Stephanofilaria dedoesi, Stephanofilaria kaeli, Stephanofilaria okinawaensis, Stephanofilaria stilesi.

(11) Nematodes of Spirurida (a) Nematodes of Gnathostomatidae, for example, Gnathostoma doloresi of Gnathostoma spp. , Gnathostoma spinigerum;
(B) Nematodes of the family Habronematidae (Habronema spp.), For example, Habronema majus, Habronema microstoma, Habronema muscae; Draschia megastoma of the genus species (Draschia spp.);
(C) Nematodes of the family Physalopteridae, for example, Physaloptera canis, Physaloptera cesticillata, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera erdocyona, Physaloptera felidis, Physaloptera gemina, Physaloptera papilloradiata, Physaloptera praeputialis, Physaloptera pseudopraerutialis, Physaoptera pseudopraerutialis rara), Physaloptera sibirica, Physaloptera vulpineus;
(D) Nematodes of the Gongylonematidae family, for example, Gongylonema pulchrum of the genus Gongylonema spp .;
(E) Spirocercidae nematodes, for example, Ascarops strongylina from Ascarops spp .;
(F) Nematodes of Thelaziidae, for example, Thelazia spip., Thelazia callipaeda, Thelazia gulosa, Thelazia lacrymalis, Rhodesian eyes Insects (Thelazia rhodesi), Scriabin eyeworms (Thelazia skrjabini).

[Control agents for other pests]
The diarylazole compound of the present invention also has pests that have poisonous needles and venom and cause damage to humans, pests that mediate various pathogens and pathogens, pests that cause discomfort to humans (toxic pests and sanitary pests)・ Excellent control of unpleasant insects.

The specific example is shown below.
(1) Hymenoptera pests, Argidae bees, Cynipidae bees, Diprionidae bees, Formicidae ants, Mutillidae bees, A wasp of the vespidae family (Vespidae).

(2) Other pest cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipedes (crustacea), paddybirds (Cimex lectularius).

[Prescription formulation]
The preparation formulation of the pest control agent, insecticide or acaricide, ectoparasite control agent or endoparasite control or control agent of the present invention is shown slightly, but additives and addition ratios should be limited to these examples It is not a thing and can be changed over a wide range. The parts in the formulation of the preparation indicate parts by weight.

  The formulation for agricultural and horticultural and paddy rice is shown below.

(Formulation 1: wettable powder)
40 parts of diarylazole compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfate ester and 3 parts of alkyl naphthalene sulfonate are uniformly mixed and finely pulverized to obtain a wettable powder of 40% active ingredient. .

(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 alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% active ingredient.

(Formulation 3: Granules)
5 parts of diarylazole compound of the present invention, 40 parts of talc, clay, 38 parts, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated to a diameter of 0.5 to 1.0 mm. Granulate to obtain granules with 5% active ingredient.

(Formulation 4: Granules)
After 5 parts of the diarylazole compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctylsulfosuccinate sodium salt, and 1 part of potassium phosphate are thoroughly pulverized and mixed, water is added and kneaded and granulated. Dry to obtain granules with 5% active ingredient.

(Formulation 5: Suspension)
10 parts of diarylazole compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of polycarboxylic acid sodium salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water are mixed, and the particle size is 3 microns. Wet mill until the following content is obtained to obtain a 10% active ingredient suspension.

  The formulation of ectoparasite control agent or endoparasite control or control agent is shown below.

(Formulation 6: Granule)
5 parts of the diarylazole compound of the invention are dissolved in an organic solvent to obtain a solution, which is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

(Formulation 7: Injection)
0.1 to 1 part of the diarylazole compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then sterilized by filtration through a sterilizing filter.

(Formulation 8: Pour-on agent)
A pour-on agent is obtained by uniformly mixing 5 parts of the diarylazole compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.

(Formulation 9: Spot-on agent)
The spot-on agent is obtained by uniformly mixing 10 to 15 parts of the diarylazole compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol.

(Formulation 10: Spray)
A spray is obtained by uniformly mixing 1 part of a diarylazole compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol.

  Next, compound examples will be shown to explain the present invention more specifically. However, this invention is not restrict | limited at all by the following compound examples.

[Example 1]
(E) -5- (Ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde O- (2,2,2- Trifluoroethyl) oxime ((E) -5- (ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde O- (2,2, 2-trifluoroethyl) oxime] (Compound No. 1-2)

３−アミノ−２−ブロモ−５−クロロピリジン（３８．５ｇ，０．１８６ｍｏｌ，１．０ｅｑ）とジエチルジスルフィド（１６ｍｌ，０．１３０ｍｏｌ，０．７ｅｑ）の１，２−ジクロロエタン（７８０ｍｌ）溶液を４０℃に加熱し、これに亜硝酸ｔ−ブチル（３３ｍｌ，０．２７９ｍｏｌ，1．５ｅｑ）を滴下した後、５０℃で６時間撹拌した。得られた液に水を注加し、クロロホルムで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物２１．６ｇ（収率４６％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.08 (1H, d), 7.36 (1H, d), 2.96 (2H, q), 1.42 (3H, t). (Step 1) Synthesis of 2-bromo-5-chloro-3- (ethylthio) pyridine [2-bromo-5-chloro-3- (ethylthio) pyridine]

A solution of 3-amino-2-bromo-5-chloropyridine (38.5 g, 0.186 mol, 1.0 eq) and diethyl disulfide (16 ml, 0.130 mol, 0.7 eq) in 1,2-dichloroethane (780 ml) was added. The mixture was heated to 40 ° C., t-butyl nitrite (33 ml, 0.279 mol, 1.5 eq) was added dropwise thereto, and the mixture was stirred at 50 ° C. for 6 hours. Water was poured into the obtained liquid, and the mixture was extracted with chloroform. The obtained organic layer was washed with saturated brine, dried over 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 21.6 g (yield 46%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.08 (1H, d), 7.36 (1H, d), 2.96 (2H, q), 1.42 (3H, t).

１−メチル−１Ｈ−イミダゾール（７．０ｇ，０．０８５ｍｏｌ，１．２ｅｑ）をテトラヒドロフラン（３３０ｍｌ）に溶解させ、反応容器をアルゴンで置換した後、−７０℃に冷却した。これにｎ−ブチルリチウムｎ−ヘキサン溶液（２．６M）を（３６ｍｌ，０．０９２ｍｏｌ，１．３ｅｑ）滴下し、−７０℃で３０分撹拌した。これに塩化亜鉛（II）（１９ｇ，０．１４２ｍｏｌ，２ｅｑ）を加えて室温まで昇温し、１時間撹拌した。その後、２−ブロモ−５−クロロ−３−（エチルチオ）ピリジン（１８ｇ，０．０７１ｍｏｌ，１．０ｅｑ）、テトラキス（トリフェニルホスフィン）パラジウム（０）（４．１ｇ，３．５５ｍｍｏｌ，０．０５ｅｑ）を加え、反応容器をアルゴン置換した後、加熱還流下で一晩撹拌した。得られた液をロッシェル塩水溶液に注加し、酢酸エチルで抽出した。得られた有機層を５％水酸化ナトリウム水溶液及び飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物１４．７ｇ（収率８２％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.31 (1H, d), 7.59 (1H, d), 7.21 (1H, d), 6.99 (1H, d), 3.85 (3H, s), 2.92 (2H, q), 1.37 (3H, t). (Step 2) 5-chloro-3- (ethylthio) -2- (1-methyl-1H-imidazol-2-yl) pyridine [5-chloro-3- (ethylthio) -2- (1-methyl-1H- Synthesis of (imidazol-2-yl) pyridine]

1-Methyl-1H-imidazole (7.0 g, 0.085 mol, 1.2 eq) was dissolved in tetrahydrofuran (330 ml), the reaction vessel was replaced with argon, and then cooled to -70 ° C. To this was added dropwise (36 ml, 0.092 mol, 1.3 eq) of n-butyllithium n-hexane solution (2.6 M), and the mixture was stirred at -70 ° C. for 30 minutes. Zinc (II) chloride (19 g, 0.142 mol, 2 eq) was added thereto, and the mixture was warmed to room temperature and stirred for 1 hour. Then, 2-bromo-5-chloro-3- (ethylthio) pyridine (18 g, 0.071 mol, 1.0 eq), tetrakis (triphenylphosphine) palladium (0) (4.1 g, 3.55 mmol, 0.05 eq) ) Was added, and the reaction vessel was purged with argon, followed by stirring overnight with heating under reflux. The resulting liquid was poured into an aqueous Rochelle salt solution and extracted with ethyl acetate. The obtained organic layer was washed with 5% aqueous sodium hydroxide solution and saturated brine, dried over 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 14.7 g of the desired product (yield 82%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.31 (1H, d), 7.59 (1H, d), 7.21 (1H, d), 6.99 (1H, d), 3.85 (3H, s), 2.92 ( 2H, q), 1.37 (3H, t).

５−クロロ−３−（エチルチオ）−２−（１−メチル−１H−イミダゾール−２−イル）ピリジン（３．０ｇ，０．０１２ｍｍｏｌ，１．０ｅｑ）をジクロロメタン１２０ｍｌへ溶解させて、０℃に冷却した。これに７０％メタクロロ過安息香酸（６．４ｇ，０．０２６４ｍｏｌ，２．２ｅｑ）を加え室温で一晩攪拌した。該反応溶液を飽和炭酸水素ナトリウム水溶液と飽和チオ硫酸ナトリウム水溶液の混合溶液へ注加し、ジクロロメタンで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物２．６ｇ（収率７６％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.83 (1H, d), 8.46 (1H, d), 7.14 (1H, s), 7.05 (1H, s), 3.93 (2H, q), 3.68 (3H, s), 1.34 (3H, t). (Step 3) 5-chloro-3- (ethylsulfonyl) -2- (1-methyl-1H-imidazol-2-yl) pyridine [5-chloro-3- (ethylsulfonyl) -2- (1-methyl-1H) -imidazol-2-yl) pyridine]

5-Chloro-3- (ethylthio) -2- (1-methyl-1H-imidazol-2-yl) pyridine (3.0 g, 0.012 mmol, 1.0 eq) was dissolved in 120 ml of dichloromethane and the mixture was heated to 0 ° C. Cooled down. 70% metachloroperbenzoic acid (6.4 g, 0.0264 mol, 2.2 eq) was added thereto, and the mixture was stirred overnight at room temperature. The reaction solution was poured into a mixed solution of a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium thiosulfate solution, and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over 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 2.6 g (yield 76%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.83 (1H, d), 8.46 (1H, d), 7.14 (1H, s), 7.05 (1H, s), 3.93 (2H, q), 3.68 ( 3H, s), 1.34 (3H, t).

５−クロロ−３−（エチルスルホニル）−２−（１−メチル−１H−イミダゾール−２−イル）ピリジン（１．５ｇ，５．２ｍｍｏｌ，１．０ｅｑ）をジクロロメタン５０ｍｌに溶解させて、０℃に冷却した。これにN−ブロモスクシンイミド（０．８９ｇ，４．９４ｍｍｏｌ，０．９５ｅｑ）を加えて、室温で２時間撹拌した。得られた液に水を注加し、ジクロロメタンで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物１．２ｇ（収率６３％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.83 (1H, d), 8.46 (1H, d), 7.14 (1H, s), 3.89 (2H, q), 3.62 (3H, s), 1.35 (3H, t). (Step 4) 2- (5-bromo-1-methyl-1H-imidazol-2-yl) -5-chloro-3- (ethylsulfonyl) pyridine [2- (5-bromo-1-methyl-1H-imidazole) -2-yl) -5-chloro-3- (ethylsulfonyl) pyridine]

5-Chloro-3- (ethylsulfonyl) -2- (1-methyl-1H-imidazol-2-yl) pyridine (1.5 g, 5.2 mmol, 1.0 eq) was dissolved in 50 ml of dichloromethane and dissolved at 0 ° C. Cooled to. N-bromosuccinimide (0.89 g, 4.94 mmol, 0.95 eq) was added thereto, and the mixture was stirred at room temperature for 2 hours. Water was poured into the resulting liquid and extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over 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 1.2 g (yield 63%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.83 (1H, d), 8.46 (1H, d), 7.14 (1H, s), 3.89 (2H, q), 3.62 (3H, s), 1.35 ( 3H, t).

２−（５−ブロモ−１−メチル−１H−イミダゾール−２−イル）−５−クロロ−３−（エチルスルホニル）ピリジン（１．１ｇ，３．０ｍｍｏｌ，１．０ｅｑ）をジオキサン（３０ｍｌ）に溶解させて、室温で撹拌した。これに水（４．５ｍｌ）、４−（トリフルオロメトキシ）フェニルボロン酸（０．５９ｇ，２．８５ｍｍｏｌ，０．９５ｅｑ）、テトラキス(トリフェニルホスフィン)パラジウム（０）（０．１７ｇ，０．１５ｍｍｏｌ，０．０５ｅｑ）、炭酸セシウム（１．５ｇ，４．５ｍｍｏｌ，１．５ｅｑ）を加え、反応容器内を窒素で置換し、１００℃で一晩撹拌した。得られた液を水へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物０．８８ｇ（収率６０％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.86 (1H, d), 8.48 (1H, d), 7.53-7.47 (2H, m), 7.36-7.29 (2H, m), 7.20 (1H, s), 3.96 (2H, q), 3.60 (3H, s), 1.37 (3H, t). (Step 5) 5-chloro-3- (ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) pyridine [5-chloro-3 -(Ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) pyridine]

2- (5-Bromo-1-methyl-1H-imidazol-2-yl) -5-chloro-3- (ethylsulfonyl) pyridine (1.1 g, 3.0 mmol, 1.0 eq) in dioxane (30 ml) Dissolved and stirred at room temperature. To this was added water (4.5 ml), 4- (trifluoromethoxy) phenylboronic acid (0.59 g, 2.85 mmol, 0.95 eq), tetrakis (triphenylphosphine) palladium (0) (0.17 g,. 15 mmol, 0.05 eq) and cesium carbonate (1.5 g, 4.5 mmol, 1.5 eq) were added, the inside of the reaction vessel was replaced with nitrogen, and the mixture was stirred at 100 ° C. overnight. The obtained liquid was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over 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 0.88 g of the desired product (yield 60%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.86 (1H, d), 8.48 (1H, d), 7.53-7.47 (2H, m), 7.36-7.29 (2H, m), 7.20 (1H, s ), 3.96 (2H, q), 3.60 (3H, s), 1.37 (3H, t).

マイクロウェーブ合成用反応容器に５−クロロ−３−（エチルスルホニル）−２−（１−メチル−５−（４−（トリフルオロメトキシ）フェニル）−１H-イミダゾール−２−イル）ピリジン（２３０ｍｇ，０．５２ｍｍｏｌ，１．０ｅｑ）とジオキサン（３ｍｌ）を加えた。これに水（０．５ｍｌ）、カリウムビニルトリフルオロボラート（１０５ｍｇ，０．７８ｍｍｏｌ，１．５ｅｑ）、ジクロロビス［ジ−t−ブチル（p−ジメチルアミノフェニル）ホスフィノ］パラジウム（II）（３０ｍｇ，０．０４ｍｍｏｌ，０．０５ｅｑ）、炭酸カリウム（１８０ｍｇ，１．３０ｍｍｏｌ，２．５ｅｑ）を加え、マイクロウェーブ合成装置にて１２０℃で４０分反応させた。得られた液を水へ注加し、酢酸エチルで抽出した。得られた有機層を飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物１９６ｍｇ（収率８６％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 8.89 (1H, d), 8.48 (1H, d), 7.51 (2H, d), 7.32 (2H, d), 7.20 (1H, s), 6.84 (1H, dd), 6.08 (1H, d), 5.64 (1H, d), 3.91 (2H, q), 3.59 (3H, s), 1.36 (3H, t). (Step 6) 3- (ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) -5-vinylpyridine [3- (ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) -5-vinylpyridine)

To a reaction vessel for microwave synthesis, 5-chloro-3- (ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) pyridine (230 mg, 0.52 mmol, 1.0 eq) and dioxane (3 ml) were added. To this was added water (0.5 ml), potassium vinyl trifluoroborate (105 mg, 0.78 mmol, 1.5 eq), dichlorobis [di-t-butyl (p-dimethylaminophenyl) phosphino] palladium (II) (30 mg, 0 .04 mmol, 0.05 eq) and potassium carbonate (180 mg, 1.30 mmol, 2.5 eq) were added, and the mixture was reacted at 120 ° C. for 40 minutes in a microwave synthesizer. The obtained liquid was poured into water and extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over 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 196 mg (yield 86%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 8.89 (1H, d), 8.48 (1H, d), 7.51 (2H, d), 7.32 (2H, d), 7.20 (1H, s), 6.84 ( 1H, dd), 6.08 (1H, d), 5.64 (1H, d), 3.91 (2H, q), 3.59 (3H, s), 1.36 (3H, t).

３−（エチルスルホニル）−２−（１−メチル−５−（４−（トリフルオロメトキシ）フェニル）−１H-イミダゾール−２−イル）−５−ビニルピリジン（１９５ｍｇ，０．４５ｍｍｏl，１．０ｅｑ）をテトラヒドロフラン : ｐＨ７リン酸緩衝液２：１溶液６ｍｌに加えた。これにN−メチルモルホリン N−オキシド水溶液（５０％）（３１６ｍｇ，１．３５ｍｍｏl，３．０ｅｑ）と四酸化オスミウム，固定化触媒Ｉ（Ｏｓ含量約７％；和光純薬工業社製）（１３０ｍｇ，０．０３６ｍｍｏｌ，０．０８ｅｑ）を加え、室温で終夜撹拌した。その後、過ヨウ素酸ナトリウム（２８７ｍｇ，１．３５ｍｍｏｌ，３．０ｅｑ）を加え室温で２時間撹拌した。反応終了後、酢酸エチル及び飽和チオ硫酸ナトリウム水溶液を加えた後、セライトろ過を行い、ろ液を酢酸エチルで抽出した。得られた有機層を水及び飽和食塩水で洗浄し、無水硫酸マグネシウムで乾燥させ、ろ過した。ろ液を減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物１３６ｍｇ（収率６９％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 10.26 (1H, s), 9.33 (1H, d), 8.93 (1H, d), 7.56-7.49 (2H, m), 7.38-7.31 (2H, m), 7.26 (1H, s), 4.10 (2H, q), 3.72 (3H, s), 1.41 (3H, t). (Step 7) 5- (Ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde [5- (ethylsulfonyl) -6- Synthesis of (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde)

3- (Ethylsulfonyl) -2- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) -5-vinylpyridine (195 mg, 0.45 mmol, 1.0 eq) ) Was added to 6 ml of a tetrahydrofuran: pH 7 phosphate buffer 2: 1 solution. N-methylmorpholine N-oxide aqueous solution (50%) (316 mg, 1.35 mmol, 3.0 eq), osmium tetroxide, immobilized catalyst I (Os content about 7%; manufactured by Wako Pure Chemical Industries, Ltd.) (130 mg) , 0.036 mmol, 0.08 eq), and stirred at room temperature overnight. Thereafter, sodium periodate (287 mg, 1.35 mmol, 3.0 eq) was added and stirred at room temperature for 2 hours. After completion of the reaction, ethyl acetate and a saturated aqueous sodium thiosulfate solution were added, followed by Celite filtration, and the filtrate was extracted with ethyl acetate. The obtained organic layer was washed with water and saturated brine, dried over 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 136 mg of the desired product (yield 69%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 10.26 (1H, s), 9.33 (1H, d), 8.93 (1H, d), 7.56-7.49 (2H, m), 7.38-7.31 (2H, m ), 7.26 (1H, s), 4.10 (2H, q), 3.72 (3H, s), 1.41 (3H, t).

５−（エチルスルホニル）−６−（１−メチル−５−（４−（トリフルオロメトキシ）フェニル）−１H-イミダゾール−２−イル）ニコチンアルデヒド（１３４ｍｇ，０．３０ｍｍｏｌ，１．０ｅｑ）のエタノ一ル（１０ｍｌ）溶液に塩酸ヒドロキシルアミン（３２ｍｇ，０．４６ｍｍｏｌ，１．５ｅｑ）と酢酸ナトリウム（６２ｍｇ，０．７５ｍｍｏｌ，２．５ｅｑ）を加え、加熱還流下で４時間撹拌した。反応終了後、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物１４０ｍｇ（収率ｑｕａｎｔ.）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 10.32 (1H, br), 9.04 (1H, d), 8.45-8.42 (1H, m), 8.09 (1H, s), 7.55-7.49 (2H, m), 7.37-7.31 (2H, m), 7.24 (1H, s), 3.78 (2H, q), 3.61 (3H, s), 1.38 (3H, t). (Step 8) (E) -5- (Ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde oxime [(E) -5- (ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde oxime]

Ethano of 5- (ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde (134 mg, 0.30 mmol, 1.0 eq) Hydroxylamine hydrochloride (32 mg, 0.46 mmol, 1.5 eq) and sodium acetate (62 mg, 0.75 mmol, 2.5 eq) were added to 1 l (10 ml) solution, and the mixture was stirred for 4 hours with heating under reflux. After completion of the reaction, the reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 140 mg (yield quant.) Of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 10.32 (1H, br), 9.04 (1H, d), 8.45-8.42 (1H, m), 8.09 (1H, s), 7.55-7.49 (2H, m ), 7.37-7.31 (2H, m), 7.24 (1H, s), 3.78 (2H, q), 3.61 (3H, s), 1.38 (3H, t).

（E）−５−（エチルスルホニル）−６−（１−メチル−５−（４−（トリフルオロメトキシ）フェニル）−１H-イミダゾール−２−イル）ニコチンアルデヒド オキシム（７６ｍｇ，０．１７ｍｍｏｌ，１．０ｅｑ）のＮ，Ｎ−ジメチルホルムアミド（３ｍｌ）溶液に炭酸セシウム（１１１ｍｇ，０．３４ｍｍｏｌ，２．０ｅｑ）と卜リフルオロメタンスルホン酸２，２，２−トリフルオロエチル（８０ｍｇ，０．３４ｍｍｏｌ，２．０ｅｑ）を加え、室温で一晩撹拌した。反応終了後、塩化アンモニウム水溶液を加え、酢酸エチルで抽出した。有機層を無水硫酸マグネシウムで乾燥した後、減圧濃縮し、得られた残渣をシリカゲルカラムクロマトグラフィーで精製することによって目的物４７ｍｇ（収率５１％）を得た。
得られた目的物の¹H-NMRを以下に示す。
¹H-NMR (400 MHz, CDCl₃) δ: 9.07 (1H, d), 8.68 (1H, d), 8.32 (1H, s), 7.54-7.48 (2H, m), 7.37-7.30 (2H, m), 7.22 (1H, s), 4.63 (2H, q), 4.00 (2H, q), 3.64 (3H, s), 1.38 (3H, t). (Step 9) (E) -5- (Ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde O- (2, 2,2-trifluoroethyl) oxime [(E) -5- (ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde O- ( 2,2,2-trifluoroethyl) oxime

(E) -5- (Ethylsulfonyl) -6- (1-methyl-5- (4- (trifluoromethoxy) phenyl) -1H-imidazol-2-yl) nicotinaldehyde oxime (76 mg, 0.17 mmol, 1 0.0 eq) in N, N-dimethylformamide (3 ml) solution with cesium carbonate (111 mg, 0.34 mmol, 2.0 eq) and 2,2,2-trifluoroethyl sulfonic acid sulfonate (80 mg, 0.34 mmol) , 2.0 eq) and stirred at room temperature overnight. After completion of the reaction, an aqueous ammonium chloride solution was added, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 47 mg (yield 51%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ) δ: 9.07 (1H, d), 8.68 (1H, d), 8.32 (1H, s), 7.54-7.48 (2H, m), 7.37-7.30 (2H, m ), 7.22 (1H, s), 4.63 (2H, q), 4.00 (2H, q), 3.64 (3H, s), 1.38 (3H, t).

  Tables 1 to 3 show examples of the diarylazole compounds of the present invention produced by the same method as in the above Examples. Table 1 shows the substituents in the compound represented by the formula (I-1). Table 2 shows the substituents in the compound represented by the formula (I-2). The physical property data of the compound was entered in the “Physical property” column. As physical property data, properties and melting point (mp) were described. The configuration E or Z in the table represents an oxime geometric isomer. “E” indicates E configuration, “Z” indicates Z configuration, and “E / Z” indicates that the compound is a mixture of compounds in both configurations. In the table, Me represents a methyl group, and Et represents an ethyl group.

Among the compounds shown in Table 2, ¹ H-NMR (CDCl ₃ ) was measured for viscous oils or amorphous physical compounds. Table 4 shows the physical property values.

[Biological test]
The following test examples show that the diarylazole compounds of the present invention are useful as active ingredients for pest control agents and ectoparasite control agents. “Parts” are based on weight.

(Preparation of test emulsion)
Emulsion (I) containing 5% active ingredient was prepared by mixing and dissolving 5 parts of the diarylazole compound of the present invention, 93.6 parts of dimethylformamide, and 1.4 parts of polyoxyethylene alkylaryl ether.

  As a control, emulsion (II) was prepared by mixing and dissolving 93.6 parts of dimethylformamide and 1.4 parts of polyoxyethylene alkylaryl ether.

The insecticidal rate was calculated by the following formula.
Insecticide rate (%) = (Number of dead insects / number of test insects) × 100

(Test Example 1) Efficacy test for Ayame Toyo 0.8 g of commercially available artificial feed (Insector LFS, manufactured by Nippon Agricultural Industry Co., Ltd.) and 1 μl of emulsion (I) were mixed well to obtain a test feed.
The test feed was packed in a plastic test container (1.4 ml capacity) at 0.2 g for each treatment zone. Next, 2 instar larvae were inoculated per treatment group. The test container was sealed with a plastic lid. It was placed in a constant temperature room at 25 ° C., and the insecticidal rate and food intake were examined on the fifth day. The test was performed in duplicate.

  As a control, the insecticidal rate and the amount of food intake were examined in the same manner as in Test Example 1 except that the emulsion (I) was changed to the emulsion (II).

  The compound No. 1-1, 1-2, 1-3, 1-4, 2-1 and 2-3 were subjected to efficacy tests against Amanita. In any compound, the insecticidal rate was 100% or the food intake was 10% or less compared to the control group. It can be seen that the diaryl azole compounds of the present invention are effective against Abayoto.

(Test Example 2) Efficacy test against diamondback moth Emulsion (I) was diluted with water so that the concentration of the present compound was 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. This cabbage leaf was put in a petri dish. To this, five 5th instar larvae were released. The petri dish was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 3 days had passed since the release, life / death determination was performed and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound No. 1-2, 1-3, 2-2, 2-3, 3-1, 3-2, 3-3, 3-4, 3-5 and 3-6 were tested for efficacy against the diamondback moth. went. The compound showed an insecticidal rate of 80% or more against the diamondback moth.

(Test Example 3) Efficacy test for bean aphids Cowpeas were raised in 3-inch pots, and bean aphid nymphs were inoculated on primary leaves. Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm, and the diluted solution was sprayed on the cowpea infested with leguminous aphid nymphs. The cowpea was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 4 days have passed since spraying, the aphid of the bean aphid was determined and the insecticidal rate was calculated. The test was performed in duplicate.

  The compounds No. 1-1, 1-2, 1-3 and 1-4 were tested for efficacy against legume aphids. All the compounds showed an insecticidal rate of 80% or more against bean aphids.

(Test Example 4) Efficacy test against Kissinogami beetle Emulsion (I) was diluted with water so that the compound of the present invention was 125 ppm to prepare a test drug solution. The dilute solution was sprayed on Chingensai seedlings (seventh true leaf unfolding stage) planted in 3 inch pots. Chinggensai seedlings were air dried and then placed in plastic cups. To this, 10 adults of Phyllotreta striolata were released. It was stored in a temperature-controlled room with a temperature of 25 ° C. and a humidity of 65%. The test was performed in duplicate.

  The compound Nos. 1-2, 1-3, 1-4, 3-1, 3-2 and 3-4 were tested for efficacy against adult beetles. The compound showed an insecticidal rate of 80% or more against adult moss.

(Test Example 5) Efficacy test against Chikaeka Emulsion (I) was diluted with water so that the compound of the present invention was 10 ppm to prepare a test drug solution. In 100 mL of this chemical solution, 20 first-instar larvae of Culex pipiens molestus were released. The next day, the number of dead insects was counted and the insecticidal rate was calculated. The test was performed in duplicate.

  The compounds No. 1-1 and 1-2 were tested for efficacy against Chikaeka. All the compounds showed 100% insecticidal rate against Chikaeka.

(Test Example 6) Efficacy test against Spodoptera litura Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. Cabbage leaves were immersed in the diluted solution for 30 seconds. The cabbage leaves were placed in a petri dish and 5 second instar larvae were released. The petri dish was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release, life / death determination was performed and the insecticidal rate was calculated. The test was performed in duplicate.

  The compound Nos. 1-2, 2-2, 3-1, 3-2 and 3-4 were tested for potency against the diamondback moth. All compounds showed an insecticidal rate of 80% or more.

  Those randomly selected from the diaryl azole compounds of the present invention have the above effects, so the diaryl azole compounds of the present invention include compounds that could not be exemplified, pest control, In particular, it can be understood that the compound has effects such as acaricide and insecticide. In addition, it can be understood that the compound has an effect on parasites harmful to human livestock such as ectoparasites.

Claims (5)

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

In formula (I),
A ¹ is a nitrogen atom (N) or CH.
A ² is CR ² .
R ² is a hydrogen atom, a group represented by —C (R ^2a ) ═N—OR ^2b , or a group represented by —C (R ^2c ) ═N—NR ^2d R ^2e .
R ^2a , R ^2b , R ^2c , R ^2d and R ^2e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
R ³ is a substituted or unsubstituted C 1-6 alkylsulfonyl group.
R ⁴ is a hydrogen atom, a group represented by —C (R ^4a ) ═N—OR ^4b , or a group represented by —C (R ^4c ) ═N—NR ^4d R ^4e .
R ^4a , R ^4b , R ^4c , R ^4d and R ^4e are each independently a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.
However, R ² and R ⁴ are not hydrogen atoms at the same time.
Q is a group represented by formula (Q-1) or formula (Q-2).

In formula (Q-1),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁵ is a substituted or unsubstituted C 1-6 alkyl group.
R ⁶ is a hydrogen atom, a substituted or unsubstituted C ^1-6 alkyl group, or a halogeno group.

In formula (Q-2),
* Is a bonding position.
Ar is a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5-6 membered heteroaryl group.
R ⁷ represents a hydrogen atom, a substituted or unsubstituted C 1-6 alkyl group, a substituted or unsubstituted C 1-6 alkenyl group, a substituted or unsubstituted C 1-6 alkynyl group, a substituted or unsubstituted amino group, or halogeno It is a group.
R ⁸ is a hydrogen atom or a substituted or unsubstituted C 1-6 alkyl group.   A pest control agent comprising at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An ectoparasite control agent comprising at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An endoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.