JP2021014407A - Phenylnicotinic acid compound and pest control agent - Google Patents

Abstract

To provide a 6-phenylnicotinic acid compound that is excellent in pest control activity, among others, insecticidal activity and/or acaricidal activity, and has excellent safety, and can be synthesized in an industrially advantageous manner, and a pest control agent containing the same as an active ingredient.SOLUTION: The present invention provides a compound of formula (I) (where Ar is a phenyl group or the like, R1 is a thiocarbamoyl group or the like, R2 is a halogeno group, a C1-6 alkyl group or the like, R3 is a halogeno group, a 5-6 membered ring heteroaryl group or the like, Q is a specific a cyclic amino group).SELECTED DRAWING: None

Description

The present invention relates to 6-phenylnicotinic acid compounds and pest control agents. More specifically, the present invention contains a 6-phenylnicotinic acid compound which has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously, and contains the same as an active ingredient. Regarding pest control agents.

As a compound structurally related to the 6-phenylnicotinic acid compound of the present invention, Patent Document 1 discloses a compound represented by the formula (A) or (B). The compound has been shown to be used as an insecticide and acaricide.

WO2015 / 032280A1

The subject of the present invention is a 6-phenylnicotinic acid compound which is excellent in pest control activity, particularly insecticidal activity and / or acaricidal activity, excellent in safety, and industrially advantageous, and an active ingredient thereof. Is to provide a pest control agent contained as.

As a result of studies for solving the above problems, the present invention including the following forms has been completed.

（式（I）中、
Ａｒは、置換若しくは無置換のフェニル基を示し、
Ｒ¹は、シアノ基、または置換若しくは無置換のチオカルバモイル基を示し、
Ｒ²は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１〜６アルキル基、水酸基、または置換若しくは無置換のＣ１〜６アルコキシ基を示し、
Ｒ³は、水素原子、ハロゲノ基、置換若しくは無置換のＣ１〜６アルキル基、水酸基、置換若しくは無置換のＣ１〜６アルコキシ基、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員環のヘテロアリール基を示し、
Ｑは、式（II）で表わされる環状アミノ基を示す。）

（式（II）中、矢印は結合位置を示し、
ｑは、括弧内のメチレンの数を示し且つ０または１であり、
Ａ環は、置換若しくは無置換のベンゼン環、または置換若しくは無置換の５〜６員ヘテロ芳香環を示し、
Ｂは、炭素原子、または窒素原子を示す。） [1] A compound represented by the formula (I) or a salt thereof.

(In formula (I),
Ar represents a substituted or unsubstituted phenyl group.
R ¹ represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R ² represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
R ³ is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C6 to 10 aryl group, or a substituted or unsubstituted C6-10 aryl group. 5-6 membered ring heteroaryl group
Q represents a cyclic amino group represented by the formula (II). )

(In equation (II), the arrow indicates the connection position,
q indicates the number of methylene in parentheses and is 0 or 1.
Ring A represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted 5- to 6-membered heteroaromatic ring.
B represents a carbon atom or a nitrogen atom. )

[2] The compound according to [1], or a salt thereof, wherein R ¹ is a substituted or unsubstituted thiocarbamoyl group.
[3] A pest control agent containing at least one selected from the group consisting of the compound according to the above [1] or [2] and a salt thereof as an active ingredient.
[4] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to the above [1] or [2] and a salt thereof as an active ingredient.
[5] An ectoparasite control or extermination agent containing at least one selected from the group consisting of the compound according to the above [1] or [2] and a salt thereof as an active ingredient.

The 6-phenylnicotinic acid compound of the present invention can control pests that pose a problem in terms of crops and hygiene. The 6-phenylnicotinic acid compounds of the present invention can effectively kill agricultural pests and mites, especially at lower concentrations. Furthermore, the 6-phenylnicotinic acid compound of the present invention can effectively control or exterminate ectoparasites that harm humans and animals.

[6-Phenylnicotinic acid compound]
The 6-phenylnicotinic acid compound of the present invention is a compound represented by the formula (I) (hereinafter, may be referred to as compound (I)) or a salt of compound (I).

In the present invention, the term "unsubstituted" means that there are only parental groups. When only the name of the parent group is described, it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that any hydrogen atom of the parent group is substituted with a group having the same or different structure as the mother nucleus. Therefore, a "substituent" is another group attached to the parent group. The number of substituents may be one or two or more. The two or more substituents may be the same or different.

The "substituent" is chemically acceptable and is not particularly limited as long as it has the effect of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro group, chloro group, bromo group, iod group;
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, n-hexyl group, etc. Alkyl group;
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 -C2-6 alkenyl groups such as hexenyl group, 5-hexenyl group;

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, etc. C2-6 alkynyl group;
C3-8 cycloalkyl groups such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cubicyl group;
C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
C6 to 10 aryl groups such as phenyl group and naphthyl group;
A 5-membered heteroaryl group such as a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group, an oxadiazolyl group, a thiadiazolyl group and a tetrazolyl group;
Heteroaryl group with 6-membered ring such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group;
Heteroaryl groups of fused rings such as indolyl groups, benzofuryl groups, benzothienyl groups, benzoimidazolyl groups, benzoxazolyl groups, benzoisooxazolyl groups, benzothiazolyl groups, quinolyl groups, isoquinolyl groups, quinoxalinyl groups;
Cyclic ether groups such as oxylanyl group, tetrahydrofuryl group, dioxolanyl group, dioxylanyl group;
Cyclic amino groups such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group;

Hydroxy group;
Oxy 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;
C2-6 alkynyloxy groups such as ethynyloxy groups and propargyloxy groups;
C6-10 aryloxy groups such as phenoxy group, naphthoxy group;
Heteroaryloxy groups with 5-6 membered rings such as thiazolyloxy groups and pyridyloxy groups;
Hydroxy C1-6 alkyl groups such as hydroxymethyl group and hydroxyethyl group;
C1-6 alkoxyalkyl groups such as methoxymethyl group and ethoxymethyl group;
C1-6 alkoxy groups such as methoxymethoxy group and ethoxymethoxy group C1-6 alkoxy groups;

Carboxylic group;
Holmil group;
C1-6 alkylcarbonyl groups such as acetyl group, propionyl group;
Formyloxy group;
C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group;
C6-10 arylcarbonyl groups such as benzoyl;

Chloromethyl group, chloroethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 1,2-dichloro-n-propyl group, perfluoropropan-2-yl C1-6 haloalkyl groups such as groups, 1-fluoro-n-butyl groups, perfluoro-n-pentyl groups;
C1-6 alkoxy C1-6 haloalkyl groups such as 1,1,1,3,3,3-hexafluoro-2-methoxypropan-2-yl group;
C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group, 2-fluoro-1-butenyl group;
C2-6 haloalkynyl groups such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C3-6 halocycloalkyl groups such as 3,3-difluorocyclobutyl group;
2-Chloro-n-propoxy group, 2,3-dichlorobutoxy group, difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2,2,3,3,3-pentafluoropropoxy group, 4,4,4-trifluorobutoxy group, (1,1,1,3,3,3-hexafluoropropan-2-yl) oxy group, etc. C1-6 haloalkoxy groups;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl groups, trifluoroacetyl groups, trichloroacetyl groups;

Cyanide group;
Nitro group;
Amino group;
C1-6 alkylamino groups such as methylamino group, dimethylamino group, diethylamino group;
C6-10 arylamino groups such as anilino groups and naphthylamino groups;
Formylamino group; C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
C1-6 alkyl sulfoxide imino groups such as S, S-dimethyl sulfoxide imino groups;

Carbamoyl group; N'-hydroxycarbamimideyl group;
C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl group, (1-imino) ethyl group, (1-imino) -n-propyl group;
Hydroxyimino C1-6 alkyl groups such as hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group;
C1-6 alkyl groups (C1-6 alkoxyiminos optionally substituted with halogeno groups) such as methoxyiminomethyl group, (1-methoxyimino) ethyl group;
C1-6 alkylcarbonyloxyimino C1-6 alkyl groups such as acetoxyiminomethyl groups;

Mercapto group;
C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
C1-6 haloalkylthio groups such as trifluoromethylthio group, 2,2,2-trifluoroethylthio group;
C2-6 alkenylthio groups such as vinylthio groups and allylthio groups;
C2-6 alkynylthio groups such as ethynylthio group and propargylthio group;
C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl groups, 2,2,2-trifluoroethylsulfinyl groups;
C2-6 alkenylsulfinyl groups such as allylsulfinyl groups;
C2-6 alkynylsulfinyl groups such as propargylsulfinyl groups;
C1-6 alkylsulfonyl groups such as methylsulfonyl groups, ethylsulfonyl groups, t-butylsulfonyl groups;
C1-6 haloalkylsulfonyl groups such as trifluoromethylsulfonyl groups, 2,2,2-trifluoroethylsulfonyl groups;
C2-6 alkenylsulfonyl groups such as allylsulfonyl groups;
C2-6 alkynylsulfonyl groups such as propargylsulfonyl groups;
Thiocarbamoyl group;
Imino (C1-6 alkylthio) methyl groups such as imino (methylthio) methyl groups;
Pentafluorosulfanil group;

Tri-C1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri-C6-10 arylsilyl groups such as triphenylsilyl groups;

Further, in these "substituents", any hydrogen atom in the substituent may be substituted with a group having a different structure.

Terms such as "C1 to 6" indicate that the number of carbon atoms of the parent group is 1 to 6 or the like. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the parent group is a butyl group and the substituent is an ethoxy group.

[Ar]
In formula (I), Ar represents a substituted or unsubstituted phenyl group.
(Also represented as X ^3.) Substituents on the phenyl group includes, for example, a halogeno group, a substituted or unsubstituted C1~6 alkyl group, a substituted or unsubstituted C2~6 alkenyl group, a substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, formyl group, substituted or unsubstituted C1-6 alkylcarbonyl group, substituted or unsubstituted C1-6 alkoxycarbonyl group, substituted or unsubstituted C1-6 alkylthio group, substituted or unsubstituted C1-6 alkylsulfinyl group, substituted or unsubstituted C1-6 alkylsulfonyl group, substituted or unsubstituted C3-8 Cycloalkyl group, substituted or unsubstituted C6-10aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted C6-10aryloxy group, substituted or unsubstituted heteroaryloxy group, nitro group, or A cyano group can be mentioned.

Examples of the "halogeno group" which is one of the substituents on the phenyl group include a fluoro group, a chloro group, a bromo group, an iod group and the like.

The "C1-6 alkyl group" which is one of the substituents on the phenyl group may be a straight chain or a branched chain. The alkyl group includes a methyl group, an ethyl group, an n-propyl group, an n-butyl group, an n-pentyl group, an n-hexyl group, an i-propyl group, an i-butyl group, an s-butyl group and a t-butyl group. , I-Pentyl group, Neopentyl group, 2-Methylbutyl group, 2,2-dimethylpropyl group, i-Hexyl group and the like.

Examples of the "C2-6 alkenyl group" which is one of the substituents on the phenyl group include a vinyl group, a 1-propenyl group, a 2-propenyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group and 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- Examples thereof include 2-butenyl group, 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.

Examples of the "C2-6 alkynyl group" which is one of the substituents on the phenyl group include an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group and 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- Examples thereof include a 3-pentynyl group, a 1-hexynyl group and a 1,1-dimethyl-2-butynyl group.

Examples of the "C1-6 alkoxy group" which is one of the substituents on the phenyl group include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group and i. -Propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, i-hexyloxy group and the like can be mentioned.

Examples of the "C2-6 alkenyloxy group" which is one of the substituents on the phenyl group include a vinyloxy group, an allyloxy group, a propenyloxy group, a butenyloxy group and the like.

Examples of the "C1-6 alkylcarbonyl group" which is one of the substituents on the phenyl group include an acetyl group and a propionyl group.

Examples of the "C1-6 alkoxycarbonyl group" which is one of the substituents on the phenyl group include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, a t-butoxycarbonyl group and the like. be able to.

The "C1-6 alkylthio group" which is one of the substituents on the phenyl group includes a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group and an i-propylthio group. And so on.

Examples of the "C1-6 alkylsulfinyl group" which is one of the substituents on the phenyl group include a methylsulfinyl group, an ethylsulfinyl group and a t-butylsulfinyl group.

Examples of the "C1-6 alkylsulfonyl group" which is one of the substituents on the phenyl group include a methylsulfonyl group, an ethylsulfonyl group and a t-butylsulfonyl group.

"C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C2-6 alkenyloxy group" which are substituents on the phenyl group. Preferred as a substituent on "C1-6 alkylcarbonyl group", "C1-6 alkoxycarbonyl group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group" Is 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-butoxy group, an s-butoxy group, an i-butoxy group, t- C1-6 alkoxy groups such as butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy groups, 2,3-dichlorobutoxy groups, trifluoromethoxy groups; C6-10 such as phenyl groups and naphthyl groups Aryl group; cyano group; can be mentioned.

Examples of the "C3-8 cycloalkyl group" which is one of the substituents on the phenyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and a cycloheptyl group.

Examples of the "C6 to 10 aryl group" which is one of the substituents on the phenyl group include a phenyl group and a naphthyl group.

Examples of the "heteroaryl group" which is one of the substituents on the phenyl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isooxazolyl group, a thiazolyl group, an isothiazolyl group, a triazolyl group and an oxadiazolyl group. 5-membered heteroaryl group such as group, thiadiazolyl group, tetrazolyl group; 6-membered heteroaryl group such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridadinyl group, triazinyl group; indolyl group, benzofuryl group, benzo [1 , 3] Examples thereof include a heteroaryl group of a fused ring such as a dioxolyl group, a benzothienyl group, a benzoimidazolyl group, a benzoxazolyl group, a benzothiazolyl group, a quinolyl group, an isoquinolyl group and a quinoxalinyl group.

Examples of the "C6 to 10 aryloxy group" which is one of the substituents on the phenyl group include a phenoxy group and a naphthoxy group.

Examples of the "heteroaryloxy group" which is one of the substituents on the phenyl group include a 5- to 6-membered heteroaryloxy group such as a thiazolyloxy group and a pyridyloxy group.

Substitution on "C3-8 cycloalkyl group", "C6-10aryl group", "heteroaryl group", "C6-10aryloxy group", or "heteroaryloxy group" which are substituents on the phenyl group The group is preferably a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group, an n-propyl group, an i-propyl group, an n-butyl group, an s-butyl group and an i-butyl group. C1-6 alkyl groups such as groups, t-butyl groups, n-pentyl groups, n-hexyl groups; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro C1-6 haloalkyl groups such as -n-butyl group, perfluoro-n-pentyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy C1-6 alkoxy groups such as groups, t-butoxy groups; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group; cyano group; Can be done.

[R ¹ , R ² , R ³ ]
R ¹ in formula (I) represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R ² in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
R ³ in formula (I) is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C6 to 10 aryl group. , Or a substituted or unsubstituted 5- to 6-membered ring heteroaryl group.

Examples of the "substituted thiocarbamoyl group" in R ¹ include mono or di-C1-6 alkyl-substituted thiocarbamoyl groups such as a methylthiocarbamoyl group, a dimethylthiocarbamoyl group, and an ethyl (methyl) thiocarbamoyl group.
The "halogeno group", "substituted or unsubstituted C1-6 alkyl group", and "substituted or unsubstituted C1-6 alkoxy group" in R ² and R ³ are the same as those specifically exemplified in Ar. I can mention things.
Examples of the "substituted or unsubstituted C6 to 10 aryl groups" in R ³ include the same ones specifically exemplified in Ar.
Examples of the "5- to 6-membered heteroaryl group" in R ³ include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isooxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group and oxadiazolyl group. Examples thereof include a 5-membered heteroaryl group such as a thiadiazolyl group and a tetrazolyl group; and a 6-membered heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group and a triazinyl group.

As the substituent on the "5- to 6-membered heteroaryl group", preferably a halogeno group such as a fluoro group, a chloro group, a bromo group and an iodo group; a methyl group, an ethyl group, an n-propyl group and 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; chloromethyl group, chloroethyl group, trifluoromethyl group, C1-6 haloalkyl groups such as 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group; methoxy group, ethoxy group, n-propoxy group, 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. C1-6 haloalkoxy group; cyano group; can be mentioned.

In the present invention, R ¹ is preferably a substituted or unsubstituted thiocarbamoyl group, and more preferably an unsubstituted thiocarbamoyl group.

[Q]
Q in formula (I) represents a cyclic amino group represented by formula (II).

In equation (II), the arrow indicates the bond position.
q indicates the number of methylene in parentheses and indicates 0 or 1.
Ring A represents a substituted or unsubstituted benzene ring, or substituted or unsubstituted 5- to 6-membered heteroaromatic ring, and B represents a carbon atom or a nitrogen atom.

The "5-membered heteroaromatic ring" in the A ring includes a pyrrole ring, a furan ring, a thiophene ring, an imidazole ring, a pyrazole ring, an oxazole ring, an isoxazole ring, a thiazole ring, an isothiazole ring, a triazole ring, and an oxadiazole ring. Examples thereof include a thiadiazole ring and a tetrazole ring.
Examples of the "6-membered heteroaromatic ring" in the A ring include a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and a triazine ring.

(Also represented as X ^4.) "Benzene ring" or "5- or 6-membered heteroaromatic ring" on substituents on the A ring as, for example, a halogeno group, a substituted or unsubstituted C1~6 alkyl group, Substituent or unsubstituted C2-6 alkenyl group, substituted or unsubstituted C2-6 alkynyl group, substituted or unsubstituted C1-6 alkoxy group, substituted or unsubstituted C2-6 alkenyloxy group, formyl group, substituted or Unsubstituted C1-6 alkylcarbonyl groups, substituted or unsubstituted C1-6 alkoxycarbonyl groups, substituted or unsubstituted C1-6 alkylthio groups, substituted or unsubstituted C1-6 alkylsulfinyl groups, substituted or unsubstituted C1-6 alkylsulfonyl groups, substituted or unsubstituted C3-8 cycloalkyl groups, substituted or unsubstituted C6-10aryl groups, substituted or unsubstituted heteroaryl groups, substituted or unsubstituted C6-10aryloxy groups , Substituent or unsubstituted heteroaryloxy group, nitro group, or cyano group.

The above "halogeno group", "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkoxy group", "substituted or unsubstituted C2-6 alkoxy group", "substituted or unsubstituted C2-6 alkoxy group" Substituted C1-6 alkoxy groups, "substituted or unsubstituted C2-6 alkenyloxy groups", "substituted or unsubstituted C1-6 alkylcarbonyl groups", "substituted or unsubstituted C1-6 alkoxycarbonyl groups" , "Substituted or unsubstituted C1-6 alkylthio groups", "Substituted or unsubstituted C1-6 alkylsulfinyl groups", "Substituted or unsubstituted C1-6 alkylsulfonyl groups", "Substituted or unsubstituted C3 ~ "8 Cycloalkyl groups", "substituted or unsubstituted C6-10 aryl groups", "substituted or unsubstituted heteroaryl groups", "substituted or unsubstituted C6-10 aryloxy groups", and "substituted or unsubstituted C6-10 aryloxy groups". as the heteroaryl group "may include the same as those concretely exemplified in the X ^3.

In the present invention, the A ring is preferably a substituted or unsubstituted 5-membered heteroaromatic ring.

The salt of compound (I) is not particularly limited as long as it is an horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron, copper and the like. Transition metal salts; salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine, hydrazine and the like can be mentioned.

The compound (I) or the salt of the compound (I) is not particularly limited depending on the production method thereof. Further, the salt of compound (I) can be obtained from compound (I) by a known method. For example, the compound (I) of the present invention or the salt of the compound (I) can be obtained by a known production method described in Examples and the like.

The 6-phenylnicotinic acid compound of the present invention (hereinafter, may be referred to as "the compound of the present invention") is excellent in the control effect of various agricultural pests affecting the growth of plants and pests such as mites. ..
In addition, the compound of the present invention is a highly safe compound because it has no phytotoxicity to crops and has low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.

The compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains and mites of acaricide-resistant strains. Examples of the pests of the resistant strain include pests such as diamondback moth, planthopper, leafhopper, and aphid, which have developed resistance to various existing drugs and are no longer effective.

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

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

[Pest control agents, insecticides or acaricides]
The pest control agent, or insecticide or acaricide of the present invention contains at least one selected from the 6-phenylnicotinic acid compounds of the present invention as an active ingredient. The amount of the compound of the present invention contained in the pest control agent or the insecticide or acaricide of the present invention is not particularly limited as long as it shows the pest control effect.

The pest control agent or insecticide or acaricide of the present invention includes grains; vegetables; root vegetables; potatoes; flowers; fruit trees, foliage plants, tea, coffee, cacao and other trees; grasses; turf. Kind: Preferably used for plants such as cotton.
In application to plants, the pest control agent or insecticide or acaricide of the present invention includes any of leaves, stems, stalks, flowers, buds, fruits, seeds, sprouts, roots, stalks, stalks, shoots, shoots, cuttings, etc. It may be used for the site. Further, the pest control agent or insecticide or acaricide of the present invention is not particularly limited depending on the species of the plant to which it is applied. Examples of the plant species include the original species, varieties, improved varieties, cultivars, mutants, etc. Examples include hybrids and genetically modified organisms (GMOs).

The pest control agent of the present invention can be used for seed treatment, foliage spraying, 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) Moths of the Arctiidae family, such as the fall webworm (Hyphantria cunea) and the mulberry moth (Lemyra imparilis);
(b) Bucculatricidae moths, such as Bucculatrix pyrivorella;
(c) Carposinidae, for example, Carposina sasakii;
(d) Crambidae moths, such as the genus Diaphania spp., The genus Diaphania indica, the genus Diaphania nitidalis; for example, the genus Ostrinia spp. Awanomeiga (Ostrinia furnacalis), European cornballer (Ostrinia nubilalis), Azukinomeiga (Ostrinia scapulalis); Others, Nikameiga (Chilo suppressalis), Cobnomeiga (Cnaphalocrocis medinalis), Momonogomadara puncta (Conaphalocrocis medinalis) Diatraea grandiosella), Kwanomeiga (Glyphodes pyloalis), Hymadalanomeiga (Hellula undalis), Shibatuga (Parapediasia teterrella);
(e) Moths of the family Twirler moth (Gelechiidae), such as caterpillar (Helcystogramma triannulella), cotton bollworm (Pectinophora gossypiella), potato moth (Phthorimaea operculella), angoumois grain moth (Sitotroga cerealella);
(f) Moths of the Geometridae family, such as Ascotis selenaria;
(g) Moths of the leaf miner moth (Gracillariidae), such as Chanohosoga (Caloptilia theivora), Satsuma mandarin (Phyllocnistis citrella), Phyllonorycter ringoniella;
(h) Skippers (Hesperiidae) butterflies, such as Parnara guttata;
(i) Lappet moth (Lasiocampidae) moths, such as Lackey moth (Malacosoma neustria);
(j) Moths of the tussock moth (Lymantriidae), such as Lymantria spp., Gypsy moth (Lymantria dispar), Gypsy moth (Lymantria monacha); Others, Chadokuga (Euproctis pseudoconspersa), Orgyia thyell (Orgyia) thyellina);

(k) Moths of the family Lyonetiidae, such as the genus Lyonetia spp., Lyonetia clerkella, Lyonetia prunifoliella malinella;
(l) Moths of the family Noctuidae, such as the genus Spodoptera spp., Spodoptera depravata, Southern army worm (Spodoptera eridania), Spodoptera exigua, Fall armyworm Spodoptera exigua, Fall armyworm. ), African Noctuidae (Spodoptera littoralis), Hasmon Noctuidae (Spodoptera litura); For example, Autographa spp., Gamakin uwaba (Autographa gamma), Tamanagin uwaba (Autographa nigrisigna); For example, Agrotis sp. Noctuidae (Agrotis ipsilon), Noctuidae (Agrotis segetum); For example, Helicoverpa spp., Helicoverpa armigera, Helicoverpa assulta, Cotton ball worm (Helicoverpa zea); (Heliothis spp.), Watakibaga (Heliothis armigera), Fake American Tobacco moth (Heliothis virescens); Others, Nakajiroshitaba (Aedia leucomelas), Mitsumonkinuwaba (Ctenoplusia)
agnata), Eudocima tyrannus, Spodoptera frugiperda (Mamestra brassicae), Awayoto (Mythimna separata), Futaobikoyaga (Naranga aenescens), Matsukiriga (Panolis japonica), Nisetama nayaga (Peridroma saucia), Nisetama nayaga (Peridroma saucia) Trichoplusia ni);
(m) Tuft moth (Nolidae) moths, such as Missia olinga (Earias insulana);
(n) Pieridae (Pieridae) butterflies, such as the large white butterfly (Pieris brassicae) and the pieris (Pieris rapae crucivora) of the genus Pieris spp.
(o) Plutellidae moths, such as the Acrolepiopsis spp., Acrolepiopsis sapporensis, Acrolepiopsis suzukiella; and other diamondback moths (Plutella xylostella);
(p) Pyralidae moths, such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, Greater wax moth;
(q) Moths of the family Sphingidae, such as the Manduca spp., Tomato horn worm (Manduca quinquemaculata), Tobacco horn worm (Manduca sexta);

(r) Moths of the family Stathmopodidae, such as the moth Stahmopoda masinissa;
(s) Moths of the family Tineidae, such as Tinea translucens;
(t) Mortricidae moths, such as the Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; for example, the Archips spp. ), Ringomonhamaki (Archips breviplicanus), Midarekakumonhamaki (Archips fuscocupreanus); Others, Tohinoshintomehamaki (Choristoneura fumiferana), Kodriinga (Cydia pomonella), Grape Hosohamaki (Eupoecilia ambiguella) ), Chahamaki (Homona magnanima), Mameshiniga (Leguminivora glycinivorella), Hosobahimehamaki (Lobesia botrana), Mamehimesayamushiga (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pill)
(u) Moths of the Ermine moth (Yponomeutidae), such as the apple fruit moth (Argyresthia conjugella).

(2) Thrips (Thysanoptera) pests
(a) Thripidae (Phlaeothripidae), for example, Thripidae (Ponticulothrips diospyrosi);
(b) Thripidae, eg Frankliniella spp., Thripidae thripidae, Thripidae, Thripidae, Thrips spp., Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae, Thripidae. Thrips palmi, Thrips tabaci; Others, Thripidae (Heliothrips haemorrhoidalis), Western flower thrips (Scirtothrips dorsalis).

(3) Pests of the order Hemiptera
(A) Auchenorrhyncha
(a) Delphacidae, for example, Himetobiunka (Laodelphax striatella), Brown planthopper (Nilaparvata lugens), Croftsnounka (Perkinsiella saccharicida), Sejirounka (Sogatella furcifera).

(B) Auchenorrhyncha
(a) Leafhoppers (Cicadellidae), for example, Empoasca spp., Leafhoppers (Empoasca fabae), Leafhoppers (Empoasca nipponica), Chanomidorihimeyokobai (Empoasca onukii), Maeno Leafhopper (Empoasca sakaii); Others, Leafhopper (Arboridia apicalis), Empoasca (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons), Cinc ).

(C) Heteroptera
(a) Riptortus clavatus of the family Riptortus pedestrianis (Alydidae);
(b) Of the leaf-footed bug family (Coreidae), for example, the stink bug (Cletus punctiger), the spider stink bug (Leptocorisa chinensis);
(c) Chinch bugs of the family Lygaeidae, for example, Chinch bug (Blissus leucopterus), Cavelerius saccharivorus, Calabash chinensis (Togo hemipterus);
(d) Miridae, for example, Kurotobikasumikame (Halticus insularis), Sabiirokasumikame (Lygus lineolaris), Cotton-free hopper (Psuedatomoscelis seriatus), Nagamugi Kasumikame (Stenodema sibiricum), Akasujikasumika ), Rice Hosomidori Kasumi turtle (Trigonotylus caelestialium);

(e) Stink bugs (Pentatomidae), eg, Nezara spp., Stink bug (Nezara antennata), Southern green stink bug (Nezara viridula); eg, Stink bug genus (Eysarcoris spp.) , Stink bug (Eysarcoris aeneus), Stink bug (Eysarcoris lewisi), Stink bug (Eysarcoris ventralis), Others, Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Dolycoris baccarum), Stink bug (Eurydema rugo) Halyomorpha halys), stink bug (Piezodorus hybneri), stink bug (Plautia crossota), stink bug (Scotinophora lurida);
(f) Of the family Pyrrhocoridae, for example, the red bug (Dysdercus cingulatus);
(g) Of the leaf-footed bug family (Rhopalidae), for example, the leaf-footed bug (Rhopalus msculatus);
(h) Of the family Scutelleridae, for example, the wheat arma custos (Eurygaster)
integriceps);
(i) Tingidae, for example, Stephanitis nashi.

(D) Sternorrhyncha
(a) Of the family Aphididae (Adelgidae), for example, the larch aphid (Adelges laricis);
(b) Whitefly family (Aleyrodidae) For example, Bemisia spp., Silver leaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Other whitefly (Aleurocanthus spiniferus), Whitefly (Di)
citri), Greenhouse whitefly (Trialeuro des vaporariorum);
(c) Aphididae, eg, Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii , European apple aphid (Aphis pomi), chicken aphid (Aphis sambuci), snowy aphid (Aphis spiraecola); for example, corn aphid (Rhopalosiphum spp.), Corn aphid (Rhopalosiphum maidis), wheat aphid (Rhopalosiphum maidis) For example, the genus Dysaphis spp., The aphid (Dysaphis plantaginea), the aphid (Dysaphis radicola); for example, the genus Macrosiphum (Macrosiphum spp.), The aphid aphid (Macrosiphum avenae), aphid tulip. (Macrosiphum
euphorbiae); For example, from the genus Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; Other, Acyrthosiphon pisum , Potato aphid (Aulacorthum solani), Wheat aphid (Brachycaudus helichrysi), Daikon aphid (Brevicoryne brassicae), Strawberry aphid (Chaetosiphon fragaefolii), Momokofuki aphid (Hyalopter) Daikon aphid (Lipaphis erysimi), Soramamehigenaga aphid (Megoura viciae), Mugius iro aphid (Metopolophium dirhodum), Lettuce aphid (Nasonovia ribis-nigri), Hopibo aphid (Phorodonhumuli), Wheat aphid (Phorodonhumuli) Aphids (Sitobion avenae), Aphids (Toxoptera aurantii);

(d) Coccidae, for example, Ceroplastes spp., Ceroplastes ceriferus, Ceroplastes rubens;
(e) Diaspididae, Pseudaulacaspis spp., Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp. Of the scale insects (Unaspis euonymi), the scale insects (Unaspis yanonensis); and others, the scale insects (Aonidiella aurantii), the scale insects (Comstockaspis perniciosa), the scale insects (Fiorinia theae), and the scale insects (Fiorinia theae). );
(f) Icerya scale insects (Margarodidae), for example, Owaraji scale insects (Drosicha corpulenta), Iceria scale insects (Icerya purchasi);
(g) Phylloxeridae, for example, Viteus vitifolii;
(h) Pseudococcidae, for example, Planococcus spp., Planococcus citri, Planococcus kuraunhiae; Other, Phenacoccus sol , Pseudococcus comstocki;
(i) Psyllidae, for example, Psylla spp., Psylla mali, Psylla pyrisuga; and other Diaphorina citri.

(4) Pests of the suborder Polyphaga
(a) Anobiidae, for example, Lasioderma serricorne;
(b) Of the Attelabidae family, for example, Byctiscus betulae, Rhynchites heros;
(c) Lyctus brunneus, for example, of the family Nagasink beetle (Bostrichidae);
(d) Of the family Cylas formicarius, for example, Cylas formicarius;
(e) Of the jewel beetle family (Buprestidae), for example, the jewel beetle (Agrilus sinuatus);
(f) Cerambycidae, for example, Citrus long-horned beetle (Anoplophora malasiaca), Longhorn beetle (Monochamus alternatus), Psacothea hilaris, Grape tiger longhorn beetle (Xylotrechus pyrrhoderus)
(g) Chrysomelidae, eg, Bruchus spp., Pea bean weevil (Bruchus pisorum), Broad bean weevil (Bruchus rufimanus); eg, Diabrotica spp., Northern corn. Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); For example, Phyllotreta spp., Phyllotreta nemorum, Phyllotreta nemorum, Phyllotreta nemorum ); Others, Aulacophora femoralis, Callosobruchuschinensis, Cassida nebulosa, Chaetocnema concinna, Colorado leaf beetle (Leptinotarsa decemlineata), Inekubihosohamushi (Oul) Broad beetle (Psylliodes angusticollis);

(h) Ladybugs (Coccinellidae), for example, Epilacna spp., Mexican bean beetle (Epilachna varivestis), Henosepilachna vigintioctopunctata;
(i) Of the Curculionidae, eg, Anthonomus spp., Watamizoumushi (Anthonomus grandis), Nashihanazoumushi (Anthonomus pomorum); for example, Sitophilus spp. , Granary Weevils (Sitophilus granarius), Sitophilus (Sitophilus zeamais); Others, Weevils (Echinocnemus squameus), Weevils (Euscepes postfasciatus), Weevils (Hylobius abietis), Alfalfata weevil (Hylobius abietis) Lissohoptrus oryzophilus), Sitophilus weevil (Otiorhynchus sulcatus), Red-spotted weevil (Sitona lineatus), Sitophilus weevil (Sphenophorus venatus);
(j) Click beetles (Elateridae), for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis;
(k) Sap beetle (Nitidulidae), for example, Sap beetle (Epuraea domina);
(l) Scarabaeidae, for example, Anomala spp., Anomala cuprea, Anomala rufocuprea; Others, Cetonia aurata, Gametis jucunda ), Nagachakogane (Heptophylla picea), European scarabaeoidea (Melolontha melolontha), Mamekogane (Popillia japonica);
(m) Of the bark beetle family (Scolytidae), for example, the spruce bark (Ips typographus);
(n) Staphylinidae, for example, Paederus littoralis
fuscipes);
(o) Tenebrionidae, for example, Tenebrio molitor, Red flour beetle (Tribolium castaneum);
(p) Of the family Red flour beetle (Trogossitidae), for example, the red flour beetle (Tenebroides mauritanicus).

(5) Pests of the order Diptera
(A) Brachycera
(a) Agromyzidae (Agromyzidae), for example, Agromyzidae (Liriomyza spp.), Agromyzidae (Liriomyza bryoniae), Agromyzidae (Liriomyza chinensis), Tomato leafminer (Liriomyza sativae), Agromyzidae (Liriomyza sativae) Others, Agromyzidae (Chromatomyia horticola), Agromyzidae (Agromyza oryzae);
(b) Anthomyiidae, eg, Delia spp., Delia platura, Delia radicum; and other sugar beet, Pegomya cunicularia;
(c) Drosophilidae (Drosophilidae), for example, fruit fly (Drosophila spp.), Drosophila melanogaster, fruit fly (Drosophila suzukii);
(d) Ephydridae, for example, Hydrollia griseola;
(e) From the family Psilidae, for example, the carrot fly (Psila rosae);
(f) Fruit flies (Tephritidae), eg, Bactrocera spp., Melon flies (Bactrocera cucurbitae), Bactrocera dorsalis; for example, Rhagoletis spp. Rhagoletis cerasi), Ringo fly (Rhagoletis pomonella); Others, Chichukai mibae (Ceratitis capitata), Olive mibae (Dacus oleae).

(B) Nematocera
(a) Cecidomyiidae, for example, Soybean Sayama fly (Asphondylia yushimai), Sorghum tama fly (Contarinia sorghicola), Hessian fly (Mayetiola destructor), Mugia katama fly (Sitodiplosis mosellana).

(6) Orthoptera pests
(a) Acrididae, eg, Schistocerca spp., American locust (Schistocerca americana), Desert locust (Schistocerca gregaria); other Australian locusts (Chortoicetes terminifera), Morocco locusts. (Dociostaurus maroccanus), Tonosama locust (Locusta migratoria), Brown locust (Locustana pardalina), Akatobi locust (Nomadacris septemfasciata), Kobane locust (Oxya yezoensis);
(b) Cricket family (Gryllidae), such as European house cricket (Acheta domestica), cricket (Teleogryllus emma);
(c) Mole cricket (Gryllotalpidae), for example, mole cricket (Gryllotalpa orientalis);
(d) Of the Bush cricket family (Tettigoniidae), for example, Tachycines asynamorus.

(7) Mites (Acari)
(A) Acarididae of the order Astigmata
(a) Acaridae mites, such as Rhizoglyphus spp., Rhizoglyphus echinopus, Rhizoglyphus robini; for example, Tyrophagus spp. (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Others, Acarus siro, Tyrophagus putrescentiae, Acarus siro, Tyrophagus putrescentiae, Acarus siro, Tyrophagus putrescentiae

(B) Prostigmata prostigmata (Actinedida)
(a) Spider mite (Tetranychidae) mites, such as Bryobia spp., Clover mite (Bryobia praetiosa), fake clover mite (Bryobia rubrioculus); for example, Eotetranychus spp. , Clover mite (Eotetranychus asiaticus), Anzu spider mite (Eotetranychus boreus), Eotetranychus celtis, Michinoku spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus geniculatus), Miyake spider mite (Eotetranychus kankitus), Eotetranychus kankitus (Eotetranychus smithi), suginami spider mite (Eotetranychus suginamensis), walnut spider mite (Eotetranychus uncatus); for example, of the genus Oligonychus spp., Sugino spider mite (Oligonychus hondoensis), clover mite (Oligonychus hondoensis), clover mite Mango spider mite (Oligonychus mangiferus), sugar cane spider mite (Oligonychus orthius), avocado spider mite (Oligonychus perseae), Ezosugi spider mite (Oligonychus pustulosus), rice spider mite (Oligonychus shinkajii), rice spider mite (Oligonychus shinkajii), genus Todomatsu Panonychus citri, Panonychus mori, Panonychus ulmi; for example, Tetranychus spp., Tetranychus cinnabarinus, Tetranychus cinnabarinus, Tetranychus cinnabarinus, Tetranychus cinnabarinus, Tetranychus ), Mizunara spider mite (Tet) ranychus quercivorus), Sagami spider mite (Tetranychus phaselus), Nami spider mite (Tetranychusurticae), Oto spider mite (Tetranychus viennensis); For example, Aponychus spp., Itomaki spider mite (Aponychus spp.), Itomaki spider mite (Aponychus spp.) The genus (Sasanychus spp.), Tetranychus akitanus, Tetranychus pusillus; for example, the genus Tetranychus (Shizotetranychus spp.), Shizotetranychus celarius, Kenagasgomori spider mite (Shizotetranychus celarius) , Shizotetranychus miscanthi, Shizotetranychus recki, Shizotetranychus schizopus; Others, Tetranychus harti, Tetranychus harti, Tuckerella pavoniformis, Tetranychus harti, Tuckerella pavoniformis

(b) Tick of the family Tenuipalpidae, for example, Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus phoenicis, Brevipalpus phoenicis russulus), Brevipalpus californicus; For example, Tenuipalpus spp., Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; Others, pineapple zhizhilashviliae;
(c) Eriophyidae mites, such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation. Aceria paradianthi, Aceria tiyingi, Aceria tulipae, Aceria zoysiea; for example, Eriophyes spp., Eriophyes chibaensis, Eriophyes chibaensis, Eriophyes chibaensis ); For example, Tomato sabi mite (Aculops lycopersici) and Mikan sabi mite (Aculops pelekassi) of the genus Acurops (Aculops spp.); For example, the peach sabi mite (Aculus fockeui) and apple sabi mite (Aculus schlechten) of the genus Aculus (Aculus spp.). ); In addition, Chanonagasabi tick (Acaphylla theavagrans), Chanosabi tick (Calacarus carinatus), Grape hamogrid tick (Colomerus vitis), Grape rust tick (Calepitrimerus vitis), Nashisabi tick (Epitrimerus pyri), Kinmoku sabi tick (Paraphytopus) ), Ryukyu mites (Phyllocotruta citri);
(d) Tarsonemidae mites, such as Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei; Others, Cyclamen mite (Phytonemus pallidus), Chano dust mites (Polyphatus) );
(e) Penthaleidae mites, such as Penthaleus spp., Penthaleus erythrocephalus, and Penthaleus major.

The pest control agent or insecticide or acaricide of the present invention may contain components other than the compound of the present invention. Examples of other components include known carriers used for formulation. In addition, as other components, conventionally known fungicides, insecticides / acaricides, nematode insecticides, soil pesticides, plant regulators, herbicides, synergists, fertilizers, soil conditioners, animal feeds And so on. By containing such other components, a synergistic effect may be produced.

Specific examples of insecticides / acaricides, nematodes, soil pesticides, anthelmintics, etc. that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.

(1) Acetylcholinesterase inhibitor:
(a) Carbamate: Aranicarb, Aldicarb, Bengiocarb, Benfracarb, Butocarboxim, Butoxycarboxym, Carbaryl, Carbofuran, Carbosulfan, Ethiophenacarb, Phenoccarb, Formetanate, Frathiocarb, Isoprocarb, Methiocarb, Methomyl, Oxamil, Pyrimicarb, Propoxil Thiodicarb, thiofanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldicarb, alixcarb, aminocarb, butocarboxim, chlorocarb, metam sodium, promecarb;

(b) Organophosphorus: acephate, azamethifos, azinephos-ethyl, azinephos-methyl, kazusaphos, chlorethoxyphos, chlorphenbinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, bearphos, cyanophos, demeton-S-methyl, diazinone, Dichlorvos / DDVP, Dichlorvos, Dimethoate, Dimethylbinphos, Disulfoton, EPN, Ethion, Etoprophos, Famfur, Fenamiphos, Fenitrothione, Fention, Hostizate, Heptenophos, Imiciaphos, Isophenphos, Isocarbhos, Isoxathion, Malathion, Mecarbamme, Metaphos Monochrometophos, Naredo, Ometoate, Oxydimethoate-Methyl, Palathion, Palatin-Methyl, Fentate, Phorate, Hosalon, Hosmet, Phosphamide, Hoxim, Pyrimiphos-Methyl, Prophenofus, Propetamphos, Prothiophos, Pyraclophos, Pyridafenthion, Kinalphos, Sulfotep, Tebupyrinphos Temephos, terbuphos, tetrachlorvos, thiometon, triazophos, trichlorfon, bamidthione; bromophos ethyl, BRP, carbophenothione, cyanophenphos, CYAP, demeton-S-methylsulfos, dichlorvos, dichlorphenthione, dioxabenzophos, ethis , Fensulfothione, flupyrifos, honophos, formotione, phosmethilan, isazophos, iodophenphos, methacryphos, pyrimiphos-ethyl, phosphocarbs, propaphos, protoate, sulprophos.

(2) GABA-operated chlorine ion channel antagonists: acetoprol, chlordane, endosulfan, ethiprol, fipronil, pilafpurrol, pyriprol; camfechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrinathrin, d-cis-trans-allethrin, d-trans-allethrin, bifentrin, bio-allethrin, bio-allethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cifluthrin, beta-cifluthrin, sihalothrin, lambda- Cihalothrin, Gamma-Pyrethrin, Cipermethrin, Alpha-Cipermethrin, Beta-Cipermethrin, Theta-Cipermethrin, Zeta-Cipermethrin, Ciphenotrin [(1R) -Trans-isomer], Deltamethrin, Empentrin [(EZ)-( 1R)-isomer], esphenvalerate, etofenprox, fenpropatrin, fenvalerate, flucitrinate, flumethrin, tau-fluvalinate, halphenprox, imiprothrin, cadesrin, permethrin, phenotrin [(1R) -trans Heterogeneous], Praletrin, Pyrethrum, Resmethrin, Silafluofen, Tefluthrin, Tetramethrin [(1R) -isomer], Tralomethrin, Transfluthrin, Allethrin, Pyrethrin, Pyrethrin I, Pyrethrin II, Profluthrin, Dimefluthrin, Bioetanometrin Permethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metoflutrin, protrifenbut, pyrethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradiflon.
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetram, spinosad.
(6) Chloride channel activator: abamectin, emamectin benzoate, repimectin, milbemectin; ivermectin, selamectin, dramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadetin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diophenolan, epophenonan, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, liquor stone.
(9) Diptera selective feeding inhibitors: Fluoricamide, Pymetrodin, Pyrifluquinazone.

(10) Mite growth inhibitors: clofentezine, difluorovidazine, hexitiazox, etoxazole.
(11) Microbial-derived insect mid-intestinal membrane-destroying agent: Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isla Elenshi, Bacillus thuringiensis subspecies Isawai, Bacillus thuringiensis subspecies Kurstaki, Bacillus thuringiensis subspecies Teneblionis, Bt Crop protein: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diafentiurone, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradiphon.
(13) Oxidative phosphorylation decoupling agent: chlorfenapyr, sulfamide, DNOC; binapacryl, dinobutone, dinocup.
(14) Nicotinic Acetylcholine Receptor Channel Blocker: Bensultap, Cartap Hydrochloride; Nelystoxin; Thiosultap Monosodium Salt, Thiocyclum.
(15) Chitin synthesis inhibitors: bistrifluron, chlorflubenzuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumron, lufenuron, novalron, nobiflumron, teflubenzuron, triflubenzuron, buprofezin, fluazuron.
(16) Diptera molting disturber: Cyromazine.
(17) Moulting hormone receptor agonists: chromaphenozide, halophenozide, methoxyphenozide, tebufenozide.
(18) Octopamine receptor agonists: Amitraz, Demiditraz, Chlordimeform.
(19) Mitochondrial electron transport chain complex III inhibitor: acequinosyl, fluacripirim, hydramethylnon.
(20) Mitochondrial electron transport chain complex I inhibitor: phenazakin, phenpyroximate, pyrimidiphen, pyridaben, tebufenpyrado, tolfenpyrad, rotenone.

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumisone.
(22) Acetyl-CoA carboxylase inhibitor: spirodiclofen, spiromesiphen, spirotetramato.
(23) Mitochondrial electron transport chain complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) Mitochondrial electron transport chain complex II inhibitor: sienopyraphen, siflumethofen, pifrubmid.
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (mechanism of action unknown): azadilactin, benzoximate, biphenazate, bromopropirate, quinomethionate, cryolite, dicoform, pyridalyl, bencrothias, sulfur, amide flumet, 1,3-dichloropropene, DCIP, Phenisobromolate, benzomate, metaldehyde, chlorbenzylate, clothiazoben, disicranyl, phenoxacrim, fentrifanyl, flubenzimine, flufenazine, gossiplua, japonilua, methoxadiazone, petroleum, potassium oleate, tetrasul, triazolesen, afidopyropen ), Fromotkin, flufiprole, fluensulphon, meperfluthrin, tetramethylfluthrin, traropyryl, dimefluthrin, methylneodecanamide, flularanel, afoxolanel, fluxametamide, 5- [5- (3,5-dichlorophenyl) -5-trifluoro Methyl-4,5-dihydroisoxazole-3-yl] -2- (1H-1,2,4-triazole-1-yl) benzonitrile (CAS: 943137-49-3), brofuranilide, and other metaldehydes ..

(29) Anthelmintic:
(a) benzimidazoles: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; fevantel, netobimin, thiophanate; thiabendazole, cambendazole;
(b) Salicylanilide system: closantel, oxyclozanide, lafoxanide, niclosamide;
(c) Substituted phenolic system: nitroxynyl, nitroscanate;
(d) Pyrimidines: Pyrantel, Morantel;
(e) Imidazothiazoles: levamisole, tetramisole;
(f) Tetrahydropyrimidines: Praziquantel, Epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, chlorthrone, metronidazole, demiditraz; piperazine, diethylcarbamazine, dichlorophene, monepantel, tribendimidine, amidantel; thiacetalsamide, merolsamine, arsenamide.

Specific examples of fungicides that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitor:
(a) RNA polymerase I inhibitor: Benalaxil, Benalaxil-M, Flaluxil, Metalaxil, Metalaxil-M; Oxadixil; Crodiracon, Offrace;
(b) Adenosine deaminase inhibitors: bupirimate, dimethilimol, etilimol;
(c) DNA / RNA synthesis inhibitors: himexazole, octylineone;
(d) DNA topoisomerase II inhibitor: oxolinic acid.

(2) Mitotic and fission inhibitors:
(a) β-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate-methyl; dietofencarb; zoxamide; etaboxam;
(b) Cell division inhibitor: pencyclon;
(c) Spectrin-like protein delocalization inhibitor: fluoricolide.

(3) Respiratory inhibitor:
(a) Complex I NADH Oxidoreductase Inhibitor: Diflumetrim; Torphenpyrad;
(b) Complex II succinate dehydrogenase inhibitors: benodanyl, flutranyl, mepronil; isofetamide; fluopirum; fenfuram, flumecyclox; carboxyne, oxycarboxyne; tifluzamide; benzobindiflupill, bixaphen, fluxapyroxado , Flametopil, isopyrazam, penflufen, penthiopyrado, sedaxan; boscalide; pyraziflumid;
(c) Complex III Ubiquinol Oxidase Qo Inhibitors: Azoxystrobin, Spiderxtrobin, Cumethoxystrobin, Enoxastrobin, Fluphenoxystrobin, Picoxystrobin, Pyraoxystrobin; Pyracrostrobin, Pyrametostrobin, triclopyricalve; cresoxime-methyl, trifloxystrobin; dymoxystrobin, phenaminestrobin, metminostrobin, orysustrobin; famoxadon; fluoroxastrobin; fenamiden; pyribenecarb; mandestrobin;
(d) Complex III Ubiquinol Reductase Qi Inhibitor: Ciazofamide; Amisulbrom;
(e) Oxidative phosphorylation decoupling agents: binapacryl, meptylzinocup, dinocup; fluazinum; ferlimzone;
(f) Oxidative phosphorylation inhibitor (inhibitor of ATP synthase): fentin acetate, fentin chloride, fentin hydroxide;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethoctrazine.

(4) Amino acid and protein synthesis inhibitors
(a) Methionine biosynthesis inhibitors: andprim, cyprodinyl, mepanipyrim, pyrimethanyl;
(b) Protein synthesis inhibitors: Blasticidin-S; casugamycin, casugamycin hydrochloride; streptomycin; oxytetracycline.

(5) Signal transduction inhibitor:
(a) Signal transduction inhibitors: quinoxyphen, proquinazide;
(b) MAP-histidine kinase inhibitors in osmotic signaling: fenpicronyl, fludioxonyl; clozolinate, iprodion, procymidone, vinclozoline.

(6) Lipid and cell membrane synthesis inhibitor:
(a) Phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(b) Lipid oxidizers: biphenyl, chloroneb, dichlorane, kinden, technazen, turquophosmethyl; etridiazole;
(c) Agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb hosetylate, prothiocarb;
(d) Pathogens Microorganisms that disrupt cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(e) Agent that disturbs cell membranes: Extract of Gosei Kayupte (tea tree).

(7) Cell membrane sterol biosynthesis inhibitor:
(a) Demethylation inhibitor at position C14 in sterol biosynthesis: triphorin; pyryphenox, pyrisoxazole; phenalimol, fluconazole, nuarimol; imazalyl, imazalyl sulfate, oxypoconazole, pefrazoate, prochloras, triflumizole , Biniconazole; azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, diphenoconazole, diniconazole, diniconazole-M, epoxyconazole, etaconazole, fenbuconazole, fluconazole, fluconazole, fluconazole, fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, fluconazole, simeconazole, tebuconazole, tetraconazole, triazimephone, triazimenol, triticonazole; prothioconazole, triticonazole, Voriconazole; Mefentrifluconazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, Dodemorph, Dodemorph Acetate, Fenpropimorph, Tridemorph; Fenpropidine, Piperlin; Spiroxamine;
(c) 3-keto reductase inhibitor in C4 demethylation of sterol biosynthesis system: fenhexamide; fenpyrazamine;
(d) Sterol biosynthetic squalene epoxide inhibitor: pyribuchicarb; naftifine, terbinafine.

(8) Inhibition of cell wall synthesis
(a) Trehalase inhibitor: validamycin;
(b) Chitin synthase inhibitors: polyoxin, polyoxolim;
(c) Cellulose Synthetic Enzyme Inhibitors: Dimethmorph, Fulmorph, Pyrimorph; Bench Avaricarb, Iprovaricarb, Torprocarb, Variphenalate; Mandipropamide.

(9) Melanin biosynthesis inhibitor
(a) Reductase inhibitor of melanin biosynthesis: fusalide; pyrokyron; tricyclazole;
(b) Dehydrating enzyme inhibitor of melanin biosynthesis: calpropamide; diclosimet; phenoxanyl;
(c) Others: Torpro Calve.

(10) Host plant resistance inducer:
(a) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: probenazole; thiazinyl; isothianil; laminarin; Reynoutria sachalinensis extract.

(11) Agents of unknown activity: simoxanyl, Josetylaluminum, phosphate (phosphate), tecrophthalam, triazoxide, flusulfamide, dichromedin, metasulfocarb, ciflufenamide, metrafenone, pyriophenone, dodine, dodine free base, fluthianyl.

(12) Agents with multiple points of action: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide; ferbum, mancozeb, maneb, Man copper, methylam, polycarbamate, propineb, tiram, dineb, dilam; captan, captahole, folpet; chlorotalonyl; diclofluanide, trilfluanide; guazatin, iminoctadine triacetate, iminoctadine albesilate trialbesilate); anilazine; dithianone; quinomethionate; fluorimide.

(13) Other agents: DBEDC, fluorofolpet, guazatin acetate, bis (8-quinolinolato) copper (II), propamidin, chloropyrrolnitrin, cyprofram, agrobacterium, betoxazine, diphenylamine, methylisothianate (MITC) ), Mildeomycin, Capsaicin, Cufraneb, Ciprosulfamide, Dazomet, Devacarb, Dichlorophene, Diphenzoquat, Difenzoquat Methylsulfonate, Flumetbel, Josetil Calcium, Josetil Sodium, Irmamycin, Natamicin, Nitrotal isopropyl , Oxamocarb, pyrrolnitrin, tebufloxin, tornifanide, zariramid, algophase, amicarthiazol, oxathiapiprolin, methylamzinc, benchazole, tricramide, uniconazole, mildeomycin, oxyphene Oxyfenthiin, picarbutrazox, Fenpicoxamid, dichlobentiazox, Quinofumelin.

Specific examples of plant growth regulators that can be mixed or used in combination with the pest control agent or insecticide or acaricide of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenurone, tidiazulone, chlorphenurone, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (also known as abscisic acid), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, gibberellin, phenothiol, 1 -Naphtylacetamide, ethicrozeto, cloxyhonac, hydrazide maleate, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonate, methyl jasmonate, (+)-strigol, (+) -Deoxystrigor, (+)-Orovancol, (+)-Solgolactone, 4-oxo-4- (2-phenylethyl) aminobutyric acid; etephon, chlormecoat, mepicote chloride, benzyladenin, 5-aminoleverellin.

[Pest control or extermination agent]
The ectoparasite control or extermination agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The ectoparasite control or extermination agent of the present invention is excellent in the effect of controlling ectoparasites that are harmful to humans and animals.

Ectoparasites parasitize the body and skin of host animals, especially warm-blooded animals and fish. Specifically, it parasitizes the back, armpits, lower abdomen, inner thighs, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal. Examples of ectoparasites include mites, lice, fleas, mosquitoes, stable flies, flesh flies, and worms.
Host animals to be treated with the ectoparasite control or extermination agent of the present invention include pet animals such as dogs and cats; pet birds; domestic animals such as cows, horses, pigs and sheep; poultry; Can be mentioned. Other examples include fish such as salmon, trout, blowfish, carp, and goldfish; insects such as honeybees, stag beetles, and beetles.
Ectoparasites parasitize in and on host animals, especially warm-blooded animals. Specifically, it parasitizes the back, armpits, lower abdomen, inner thighs, etc. of the host animal and inhabits by obtaining nutrient sources such as blood and dandruff from the animal.

The ectoparasite control or control agent of the present invention can be applied by a known veterinary method (topical, oral, parenteral or subcutaneous administration). The method is to administer it orally to animals by mixing tablets, capsules, feed, etc .; to administer it to animals by dipping solution, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); oily or A method of locally administering an aqueous solution by spraying, pore-on, spot-on, etc .; Kneading an ectoparasite control agent into a resin, molding 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 locally administering;

Specific examples of ectoparasites that can be controlled or exterminated by the ectoparasite control or extermination agent of the present invention are shown below.

(1) Mites (Acari)
Dermanyssidae mites, Macronyssidae mites, Laelapidae mites, Varroidae mites, Argasidae mites, Ixodidae mites, cucumber mites Insect-parasitic mites such as family (Psoroptidae) mites, mites of the family Sarcoptidae, mites of the family Knemidokoptidae, mites of the family Demodixidae, mites of the family Trombiculidae, and mites of mulberry. ..
(2) Lice (Phthiraptera)
Lice of the family Haematopinidae, lice of the family Linognathidae, mallophaga of the family Menoponidae, mallophaga of the family Philopteridae, mallophaga of the family Mammal chewing (Trichodectida).
(3) Flea eyes (Siphonaptera)
Flea of the family Pulicidae, eg, dog fleas (Ctenocephalides spp.), Dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis);
Fleas of the family Chigoe flea (Tungidae), fleas of the family Ceratophyllidae, fleas of the family Ceratophyllidae (Leptopsyllidae).
(4) Hemiptera.
(5) Diptera mosquitoes, gnats of the family Curicidae, gnats of the family Glossinidae (Ceratopogonidae), mosquitoes of the family Glossinidae (Tabanidae), flies of the family Muscidae, Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Glossinidae Flies, Hipboscidae Flies, Calliphoridae Flies, Oestridae Flies.

[Control agents for other pests]
In addition, the control effect of pests that have poisonous needles and toxic liquids and damage human animals, pests that transmit various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, unpleasant pests, etc.) Is excellent.
A specific example is shown below.
(1) Hymenoptera pests Vespidaceae (Argidae) bees, Gall wasps (Cynipidae) bees, Vespids (Diprionidae) bees, Ali family (Formicidae) ants, Velvet ants (Mutillidae) bees, A bee of the Vespidae family.
(2) Other pests Cockroaches (Blattodea), termites (termite), spiders (Araneae), mucades (cetipede), millipedes (millipede), crustacea (crustacea), Nanjing insects (Cimex lectularius).

[Prescription]
Some examples of formulations of the pest control agent, insecticide, acaricide, and ectoparasite control or control agent of the present invention are shown. However, the present invention is not limited to these formulation examples. The “part” in the formulation example is based on weight.

The formulation formulas for agriculture and horticulture and paddy rice are shown below.

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

(Formulation Example 2: Emulsion)
30 parts of the compound of the present invention, 33 parts of xylene, 30 parts of dimethylformamide, and 7 parts of polyoxyethylene alkyl allyl ether are mixed and dissolved to obtain an emulsion containing 30% of the active ingredient.

(Formulation Example 3: Granules)
5 parts of the compound of the present invention, 40 parts of talc, 38 parts of clay, 10 parts of bentonite, and 7 parts of sodium alkyl sulfate are uniformly mixed and finely pulverized, and then granulated into granules having a diameter of 0.5 to 1.0 mm. Then, a granule having 5% of the active ingredient is obtained.

(Formulation Example 4: Granules)
5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of sodium dioctyl sulfosuccinate, and 1 part of potassium phosphate are mixed and pulverized, water is added to the mixture, and the mixture is thoroughly kneaded and then granulated and dried. To obtain a granule of 5% of the active ingredient.

(Formulation Example 5: Suspension)
Mix 10 parts of the compound of the present invention, 4 parts of polyoxyethylene alkyl allyl ether, 2 parts of sodium polycarboxylic acid salt, 10 parts of glycerin, 0.2 part of xanthan gum, and 73.8 parts of water until the particle size becomes 3 μm or less. Wet grind to obtain a suspension of 10% active ingredient.

The formulation of the ectoparasite control agent is shown below.

(Formulation Example 6: Granules)
Five parts of the compound of the present invention are dissolved in an organic solvent to obtain a solution, the solution is sprayed onto 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure to obtain granules. This type of granule can be used by mixing with animal food.

(Formulation Example 7: Injectable)
0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil are uniformly mixed, and then sterilized by filtration through a sterilization filter to obtain an injection.

(Formulation Example 8: Poreon agent)
A poreon agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic acid ester, and 85 parts of isopropanol.

(Formulation Example 9: Spot-on agent)
10 to 15 parts of the compound of the present invention, 10 parts of palmitic acid ester, and 75 to 80 parts of isopropanol are uniformly mixed to obtain a spot-on agent.

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

(Example of compound synthesis)
Next, an example will be shown, and the compound of the present invention will be described more specifically. However, the present invention is not limited to the following examples.

５−（２−クロロ−５,６,７,８−テトラヒドロ−１,６−ナフチリジン−６−カルボニル）−６−（トリフルオロメチル）−２−（４−（トリフルオロメチル）フェニル）ニコチノニトリル（５０．１ｍｇ）をＮ，Ｎ−ジメチルホルムアミド（１ｍｌ）に溶解させた。これに塩化マグネシウム六水和物（２６ｍｇ）、および水硫化ナトリウム（２１ｍｇ）を加えて室温にて１時間撹拌した。得られた液に飽和塩化アンモニウム水溶液を注加し、酢酸エチルで抽出し、飽和食塩水で洗浄した。有機層を無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、目的化合物（４９．４ｍｇ、収率９１％）を得た。得られた目的化合物のＮＭＲデータを以下に示す。
¹H-NMR (CDCl₃,δppm) 8.00-8.09(3H,m),7.62-7.77(3H,m),6.09-7.50(3H,m)4.37-5.02(2H,m),3.59-4.30(2H,m),2.98-3.15(2H,m) Example 1

5- (2-Chloro-5,6,7,8-Tetrahydro-1,6-naphthylidine-6-carbonyl) -6- (trifluoromethyl) -2- (4- (trifluoromethyl) phenyl) nicotino Nitrile (50.1 mg) was dissolved in N, N-dimethylformamide (1 ml). Magnesium chloride hexahydrate (26 mg) and sodium hydrosulfide (21 mg) were added thereto, and the mixture was stirred at room temperature for 1 hour. A saturated aqueous solution of ammonium chloride was added to the obtained solution, the mixture was extracted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the target compound (49.4 mg, yield 91%). The NMR data of the obtained target compound is shown below.
^{1 1} H-NMR (CDCl ₃ , δppm) 8.00-8.09 (3H, m), 7.62-7.77 (3H, m), 6.09-7.50 (3H, m) 4.37-5.02 (2H, m), 3.59-4.30 (2H) , m), 2.98-3.15 (2H, m)

５−シアノ−２−（ジフルオロメチル）−６−（４−（トリフルオロメチル）フェニル）ニコチン酸（０．１７ｇ）をジクロロメタン（１０ｍｌ）に懸濁させた。これに５−ブロモイソインドリン（０．１ｇ）、４−（Ｎ，Ｎ−ジメチルアミノ）ピリジン（０．１２ｇ）、および１−[３−（ジエチルアミノ）プロピル]−３−エチルカルボジイミド塩酸塩（０．１９ｇ）を加え、室温にて一晩撹拌した。得られた液を氷水に注加し、クロロホルムで抽出し、水で洗浄し、次いで飽和食塩水で洗浄した。その後、無水硫酸マグネシウムで乾燥させた。溶媒を減圧留去し、得られた残渣をシリカゲルカラムクロマトグラフィー（展開溶媒：n-ヘキサン／酢酸エチル）で精製し、目的化合物（０．１５ｇ、収率５８％）を得た。得られた目的化合物のＮＭＲデータを以下に示す。
¹H-NMR (CDCl₃,δppm) 4.63(d,2H),5.00(d,2H),6.87(t,1H),7.04-7.06(m,1H),7.31-7.53(m,3H),7.84(d,2H),8.13(d,2H),8.22(s,1H) Example 2
Production of 5- (5-bromoisoindoline-2-carbonyl-6- (difluoromethyl) -2- (4- (trifluoromethyl) phenyl) nicotinonitrile

5-Cyano-2- (difluoromethyl) -6- (4- (trifluoromethyl) phenyl) nicotinic acid (0.17 g) was suspended in dichloromethane (10 ml). To this were 5-bromoisoindoline (0.1 g), 4- (N, N-dimethylamino) pyridine (0.12 g), and 1- [3- (diethylamino) propyl] -3-ethylcarbodiimide hydrochloride (0). .19 g) was added, and the mixture was stirred overnight at room temperature. The obtained solution was poured into ice water, extracted with chloroform, washed with water, and then washed with saturated brine. Then, it was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate) to obtain the target compound (0.15 g, yield 58%). The NMR data of the obtained target compound is shown below.
^{1 1} H-NMR (CDCl ₃ , δppm) 4.63 (d, 2H), 5.00 (d, 2H), 6.87 (t, 1H), 7.04-7.06 (m, 1H), 7.31-7.53 (m, 3H), 7.84 (d, 2H), 8.13 (d, 2H), 8.22 (s, 1H)

Table 1 shows a part of the compound of the present invention produced by the same method as in the above-mentioned Examples. Table 1 shows the substituents of the compound represented by the formula (I-1). In the formula, n indicates the number of substituents (X ³ ) on the benzene ring. In the column of physical properties in Table 1, the properties or melting points (mp) are shown. In Table 1, Me represents a methyl group. The arrow indicates the connection position.

Among the compounds shown in Table 1, ¹ H-NMR (CDCl ₃ ) was measured for compounds having amorphous physical characteristics. The measured values are shown below.
Compound No. (C-4): 1H-NMR (400MHz, CDCl ₃ ) δppm: 2.98 (s, 3H), 3.88-3.92 (m, 4), 7.04-7.32 (m, 3H), 7.89 (d, 2H) , 8.10 (d, 2H), 8.60 (s, 1H).

[Biological test]
The following test examples show that the compound of the present invention is useful as an active ingredient of an insecticide, an acaricide or a ectoparasite control agent.

(Preparation of test emulsion)
5 parts by weight of the compound of the present invention, 93.6 parts by weight of dimethylformamide, and 1.4 parts by weight of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion (I) having 5% of the active ingredient.
98.6 parts by weight of dimethylformamide and 1.4 parts by weight of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare an emulsion (II) containing no active ingredient.

(Test Example 1) Efficacy test against armyworm To obtain test feed (I) by mixing 0.8 g of a commercially available artificial feed (Insect LFS, manufactured by Nosan Corporation) and 1 μl of emulsion (I) well. A plastic test container (1.4 ml volume) filled with 0.2 g of test feed (I) was designated as a test group.
0.8 g of a commercially available artificial feed (Insect LFS, manufactured by Nosan Corporation) and 1 μl of an emulsion (II) were mixed to obtain a test feed (II). A plastic test container (1.4 ml volume) filled with 0.2 g of test feed (II) was used as a control group.
Two second-instar armyworm larvae were inoculated into the containers of the test plot and the control plot and sealed with a plastic lid. They were placed in a homeothermic chamber at 25 ° C. and the insecticidal rate and food intake were examined on the 5th day. The test was performed in two iterations.
The efficacy test of the compound of Compound No. C-3 against Mythimna separata was carried out. The compound had an insecticidal rate of 100% with respect to armyworm. The amount of food consumed in the test group was 10% or less of the amount consumed in the control group.

(Test Example 2) Efficacy test against Kanzawa spider mites Five adult female Kanzawa spider mites from Okayama prefecture were inoculated on the primary leaves of mung bean. Then, the emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm to obtain a drug. This drug was sprayed on the mung beans and air-dried. Then, it was placed in a thermostatic chamber having a temperature of 25 ° C. and a humidity of 65%. The life and death of mites was investigated 10 days after spraying. The test was performed in two iterations.
The compounds of Compound Nos. C-3, C-4, and C-5 were tested for efficacy against Kanzawa spider mites. Both compounds showed an insecticidal rate of 90% or more. Mung beans grew well without dying.

(Test Example 3) Efficacy test against Nami spider mites Eight green bean seedlings were raised in a 3 inch pot, and eight adult Nami spider mites from Aomori prefecture were inoculated on the primary leaves. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. The diluted solution was sprayed on the green beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of mites was investigated 10 days after spraying. The test was performed in two iterations.
The compounds of Compound Nos. C-1, C-3, and C-6 were tested for efficacy against spider mites. Both compounds showed an insecticidal rate of 90% or more. Green beans grew well without dying.

Randomly selected compounds of the present invention exert the above-mentioned effects. Therefore, the compounds of the present invention, including compounds that could not be exemplified, control pests, especially insecticides, acaricides, and ectoparasites. It can be understood that it is a compound that has effects such as insect control or extermination, does not cause chemical damage to plants, and has little toxicity to humans, livestock and fish and has little effect on the environment.

Claims (5)

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

(In formula (I),
Ar represents a substituted or unsubstituted phenyl group.
R ¹ represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R ² represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.
R ³ is a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkoxy group, a substituted or unsubstituted C6 to 10 aryl group, or a substituted or unsubstituted C6-10 aryl group. 5-6 membered ring heteroaryl group
Q represents a cyclic amino group represented by the formula (II). )

(In equation (II), the arrow indicates the connection position,
q indicates the number of methylene in parentheses and is 0 or 1.
Ring A represents a substituted or unsubstituted benzene ring or a substituted or unsubstituted 5- to 6-membered heteroaromatic ring.
B represents a carbon atom or a nitrogen atom. ) The compound according to claim 1, or a salt thereof, wherein R ¹ is a substituted or unsubstituted thiocarbamoyl group. A pest control agent containing at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient. An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient. An ectoparasite control or extermination agent containing at least one selected from the group consisting of the compound according to claim 1 or 2 and a salt thereof as an active ingredient.