JP2019077618A - Phenyl nicotinic acid compound and pest controlling agent - Google Patents

Abstract

To provide a specific phenyl nicotinic acid compound capable of being used as a pest controlling agent, an insecticidal or acaricidal and ectoparasite controlling agent, or expellent.SOLUTION: There is provided a compound represented by the formula (I). In the formula (I), Ar represents a phenyl group or the like, Rrepresents a thiocarbamoyl group or the like, Rrepresents a halogeno group, Ctoalkyl group or the like, Rrepresents a halogeno group, a heteroaryl group with a 5 to 6-membered ring or the like, Q represents a substituted or unsubstituted phenyl group, substituted or unsubstituted heteroaryl group with a 5-membered ring, or a piperazine ring with a substituted or unsubstituted heteroaryl group with a 6-membered ring bound to 4 position nitrogen.SELECTED DRAWING: None

Description

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

  Patent Document 1 discloses a compound represented by Formula (A) or (B) as a compound structurally related to the 6-phenyl nicotinic acid compound of the present invention. It has been shown that the compounds are used as insecticides and acaricides.

WO 2015/032280 A1

  The object of the present invention is to provide a 6-phenyl nicotinic acid compound which is excellent in pest control activity, particularly insecticidal activity and / or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized, and an active ingredient thereof To provide the pest control agent contained as

  As a result of examining in order to solve the above-mentioned subject, it came to complete the present invention including the following forms.

（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、
Ｘは、環状アミノ基上の置換基を示し且つハロゲノ基、または置換若しくは無置換のＣ１〜６アルキル基であり、
ｎは、Ｘの数を示し且つ０〜４のいずれかの整数であり、
Ｙ^aは、置換若しくは無置換のフェニル基、置換若しくは無置換の５員環のヘテロアリール基、または置換若しくは無置換の６員環のヘテロアリール基を示す。） [1] A compound represented by the formula (I) or a salt thereof.

(In the 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 represents 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 C6-10 aryl group, or a substituted or unsubstituted group And a 5- to 6-membered heteroaryl group of
Q represents a cyclic amino group represented by formula (II). )

(In the formula (II), the arrow indicates a bonding position,
X represents a substituent on a cyclic amino group and is a halogeno group, or a substituted or unsubstituted C1-6 alkyl group,
n represents the number of X and is an integer from 0 to 4;
Y ^a represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted 5-membered heteroaryl group, or a substituted or unsubstituted 6-membered heteroaryl group. )

[2] The compound according to [1] or a salt thereof, wherein R ¹ is a substituted or unsubstituted thiocarbamoyl group.
[3] The compound according to [1] or 2, or a salt thereof, wherein Y ^a is a substituted or unsubstituted 5-membered heteroaryl group.
[4] A pest control agent comprising, as an active ingredient, at least one compound selected from the group consisting of the compounds according to any one of the above [1] to [3], and salts thereof.
[5] An insecticidal or acaricidal agent which comprises, as an active ingredient, at least one selected from the group consisting of the compounds according to any one of the above [1] to [3], and salts thereof.
[6] An ectoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to any one of the above [1] to [3], and a salt thereof.

  The 6-phenyl nicotinic acid compound of the present invention can control pests that cause problems in agricultural products and hygiene. The 6-phenyl nicotinic acid compounds of the present invention are capable of effectively killing, among other things, agricultural pests and mites at lower concentrations. Furthermore, the 6-phenyl nicotinic acid compound of the present invention can effectively control or control ectoparasites that harm humans and animals.

[6-phenyl nicotinic acid compound]
The 6-phenyl nicotinic acid 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).

In the context of the present invention, the term "unsubstituted" means that it is only the parent group. When it is described only by the name of a mother core, it means "unsubstituted" unless otherwise noted.
On the other hand, the term "substituted" means that any hydrogen atom of the mother core group is substituted with a group having the same or a different structure as the mother nucleus. Thus, the “substituent” is another group bonded to the mother core. 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 the effects of the present invention are obtained.
The following groups can be mentioned as specific examples of the group that can be a "substituent".
Halogeno groups such as fluoro, chloro, bromo and iodo;
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 An 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 group 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. A C2-6 alkynyl group of
A C 3-8 cycloalkyl group such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cuvanyl group and the like;
C3-8 cycloalkenyl groups such as 2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
C6-10 aryl groups such as phenyl group and naphthyl group;
5-membered heteroaryl group such as pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group, tetrazolyl group and the like;
6-membered heteroaryl groups such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl and triazinyl;
Heteroaryl groups of fused rings such as indolyl group, benzofuryl group, benzothienyl group, benzoimidazolyl group, benzoxazolyl group, benzoisoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, quinoxalinyl group and the like;
Cyclic ether groups such as oxiranyl group, tetrahydrofuryl group, dioxolanyl group, diochiranyl group;
Cyclic amino groups such as aziridinyl group, pyrrolidinyl group, piperidyl group, piperazinyl group, morpholinyl group;

Hydroxyl group;
An oxo group;
C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t-butoxy and the like;
C 2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
A C 2-6 alkynyloxy group such as ethynyloxy group, propargyloxy group;
A C6-10 aryloxy group such as phenoxy group and naphthoxy group;
5-6 membered heteroaryloxy group such as thiazolyloxy group, pyridyloxy group;
Hydroxy C1-6 alkyl groups such as hydroxymethyl group, hydroxyethyl group;
C1-6 alkoxyalkyl groups such as methoxymethyl group and ethoxymethyl group;
C1-6 alkoxy C1-6 alkoxy group such as methoxymethoxy group, ethoxymethoxy group;

Carboxyl group;
Formyl group;
C1-6 alkylcarbonyl group such as acetyl group, propionyl group;
Formyloxy group;
C1-6 alkyl carbonyloxy group such as acetyloxy group, propionyloxy group, n-propyl carbonyloxy group, i-propyl carbonyloxy group;
C1-6 alkoxycarbonyl groups such as methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, t-butoxycarbonyl group and the like;
C6-10 arylcarbonyl groups such as benzoyl group;

Chloromethyl group, chloroethyl group, difluoromethyl group, trifluoromethyl group, 2,2,2-trifluoroethyl group, perfluoroethyl group, 1,2-dichloro-n-propyl group, perfluoropropan-2-yl A C1-6 haloalkyl group such as a group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
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;
C 2-6 haloalkynyl groups such as 4, 4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
A C3-6 halocycloalkyl group such as a 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 group of
C 2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group, 3-bromobutenyloxy group;
C1-6 haloalkyl carbonyl group such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group;

Cyano group;
Nitro group;
Amino group;
C1-6 alkylamino group such as methylamino group, dimethylamino group, diethylamino group;
A C 6-10 arylamino group such as anilino, naphthylamino and the like;
Formylamino group; C1-6 alkylcarbonylamino group such as acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group and the like;
C1-6 alkoxycarbonylamino groups such as methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group and the like;
A C1-6 alkyl sulfoximino group such as S, S-dimethyl sulfoximino group;

A carbamoyl group; N'-hydroxycarbamimidoyl group;
C1-6 alkylaminocarbonyl groups such as methylaminocarbonyl group, dimethylaminocarbonyl group, ethylaminocarbonyl group, i-propylaminocarbonyl group and the like;
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 alkoxyimino optionally substituted with halogeno group) such as methoxyiminomethyl group, (1-methoxyimino) ethyl group, C1-6 alkyl group;
A C1-6 alkylcarbonyloxyimino C1-6 alkyl group such as an acetoxyiminomethyl group;

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 and the like;
A trifluoromethylthio group, a C1-6 haloalkylthio group such as a 2,2,2-trifluoroethylthio group;
A C 2-6 alkenylthio group such as a vinylthio group, an allylthio group and the like;
A C 2-6 alkynylthio group such as ethynylthio group, propargylthio group;
C1-6 alkylsulfinyl groups such as methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group;
A C1-6 haloalkylsulfinyl group such as trifluoromethylsulfinyl group, 2,2,2-trifluoroethylsulfinyl group;
A C 2-6 alkenylsulfinyl group such as an allylsulfinyl group;
A C 2-6 alkynyl sulfinyl group such as propargyl sulfinyl group;
C1-6 alkylsulfonyl groups such as methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like;
A C1-6 haloalkylsulfonyl group such as trifluoromethylsulfonyl group, 2,2,2-trifluoroethylsulfonyl group;
A C 2-6 alkenylsulfonyl group such as an allylsulfonyl group;
A C 2-6 alkynyl sulfonyl group such as propargyl sulfonyl group;
A thiocarbamoyl group;
An imino (C1-6 alkylthio) methyl group such as an imino (methylthio) methyl group;
Pentafluorosulfanyl group;

Tri C 1-6 alkylsilyl groups such as trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group;
Tri C 6-10 aryl silyl groups such as triphenyl silyl group;

  Moreover, as for these "substituents", any hydrogen atom in the said substituent may be substituted by the group of a different structure.

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

[Ar]
In formula (I), Ar represents a substituted or unsubstituted phenyl group.
As a substituent on the phenyl group (which may be represented as X ³ ), 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 A cycloalkyl group, a substituted or unsubstituted C6-10 aryl group, a substituted or unsubstituted heteroaryl Lumpur group, a substituted or unsubstituted C6~10 aryloxy group, a substituted or unsubstituted hetero aryloxy group, and a nitro group or a cyano group.

  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 and an iodo group.

  The "C1-6 alkyl group" which is one of the substituents on the phenyl group may be linear or branched. As an alkyl group, a methyl group, an 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 And 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 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- Examples 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 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- Examples include 3-pentynyl group, 1-hexynyl group, 1,1-dimethyl-2-butynyl group and the like.

  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, 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 and a butenyloxy group.

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

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

  The “C1-6 alkylthio group” which is one of the substituents on the phenyl group is a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an n-pentylthio group, an n-hexylthio group, an i-propylthio group And the like.

  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 substituents on a phenyl group include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group and the like.

  "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group" which is a substituent on phenyl group, "C2-6 alkenyloxy group" As a substituent on a C1-6 alkylcarbonyl group, a "C1-6 alkoxycarbonyl group", a "C1-6 alkylthio group", a "C1-6 alkylsulfinyl group", or a "C1-6 alkylsulfonyl group", preferred Is a halogeno group such as fluoro, chloro, bromo or iodo; methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy, t- C1-6 alkoxy group such as butoxy group; C1-6 group such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, trifluoromethoxy group etc. R6 alkoxy group; C6-10 aryl groups such as phenyl group and naphthyl group; cyano group;

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

  A phenyl group, a naphthyl group, etc. can be mentioned as "C6-10 aryl group" which is one of the substituents on a phenyl group.

  As the "heteroaryl group" which is one of the substituents on the phenyl group, pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group Group, 5-membered heteroaryl group such as thiadiazolyl group, tetrazolyl group; pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group, etc. 6-membered heteroaryl group; indolyl group, benzofuryl group, benzo [1 , 3] Dioxolyl group, benzothienyl group, benzoimidazolyl group, benzoxazolyl group, benzothiazolyl group, quinolyl group, isoquinolyl group, heteroaryl group of fused ring such as quinoxalinyl group and the like, and the like can be mentioned.

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

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

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

[R ¹ , R ² , R ³ ]
R ¹ in the formula (I) represents a cyano group or a substituted or unsubstituted thiocarbamoyl group.
R ² in the 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 the 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 C6-10 aryl group Or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

Examples of the “substituted thiocarbamoyl group” in R ¹ include mono- or di-C 1-6 alkyl-substituted thiocarbamoyl groups such as a methylthiocarbamoyl group, a dimethylthiocarbamoyl group, and an ethyl (methyl) thiocarbamoyl group.
The “halogeno group”, the “substituted or unsubstituted C1-6 alkyl group” and the “substituted or unsubstituted C1-6 alkoxy group” for R ² and R ³ are the same as those specifically exemplified for Ar The thing can be mentioned.
Examples of the “substituted or unsubstituted C6-10 aryl group” for R ³ include the same as those specifically exemplified for Ar.
The “5- to 6-membered ring heteroaryl group” in R ³ is a pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, Examples thereof include 5-membered heteroaryl groups such as thiadiazolyl group and tetrazolyl group; and 6-membered heteroaryl groups such as pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group and triazinyl group.

  As a substituent on the "5- to 6-membered ring heteroaryl group", preferably a halogeno group such as a fluoro group, a chloro group, a bromo group or an iodo group; a methyl group, an ethyl group, an n-propyl group or an i-propyl group C1-6 alkyl groups such as n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group, etc .; 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 and the like; methoxy group, ethoxy group, n-propoxy group, i-propoxy group , C1-6 alkoxy group such as n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group, etc .; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy , Cl to 6 haloalkoxy group such as trifluoromethoxy group, a cyano group, can be exemplified.

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

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

In Formula (II), the arrow indicates a bonding position.
In the formula (II), X represents a substituent on a cyclic amino group and is a halogeno group or a substituted or unsubstituted C1-6 alkyl group, n represents the number of X and is any of 0 to 4 It is an integer of
Examples of the “halogeno group” and the “substituted or unsubstituted C1-6 alkyl group” for X include the same as those specifically exemplified for Ar.

In formula (II), Y ^a represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted 5-membered ring heteroaryl group, or a substituted or unsubstituted 6-membered ring heteroaryl group.

Examples of “5-membered ring heteroaryl group” in Y ^a include pyrrolyl group, furyl group, thienyl group, imidazolyl group, pyrazolyl group, oxazolyl group, isoxazolyl group, thiazolyl group, isothiazolyl group, triazolyl group, oxadiazolyl group, thiadiazolyl group And tetrazolyl groups.
Examples of the “6-membered ring heteroaryl group” in Y ^a include pyridyl group, pyrazinyl group, pyrimidinyl group, pyridazinyl group, triazinyl group and the like.

Examples of the substituent (which may be represented as X ⁴ ) on the above-mentioned phenyl group, 5-membered ring heteroaryl group, and 6-membered ring heteroaryl group include, for example, halogeno group, substituted or unsubstituted C1 6 alkyl group, substituted 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 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 C6-10 aryl group, substituted or unsubstituted heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted heteroaryloxy group, nitro group, or cyano group be able to.

The above "halogeno group", "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C2-6 alkenyl group", "substituted or unsubstituted C2-6 alkynyl group", "substituted or unsubstituted Substituted C1-6 alkoxy group, "substituted or unsubstituted C2-6 alkenyloxy 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 C3-6 8 cycloalkyl group "," substituted or unsubstituted C6-10 aryl group "," substituted or unsubstituted heteroaryl group "," Or unsubstituted C6~10 aryloxy group ", and as" substituted or unsubstituted heteroaryl group "may include the same as those concretely exemplified in the X ^3.

In the present invention, Y ^a is preferably a substituted or unsubstituted 5-membered heteroaryl group.

  The salt of compound (I) is not particularly limited as long as it is an agronomically 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 And salts of transition metals such as ammonia, triethylamine, tributylamine, pyridine, and salts of organic bases such as hydrazine.

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

The 6-phenyl nicotinic acid compound of the present invention (hereinafter sometimes referred to as "the compound of the present invention") is excellent in controlling various agricultural pests and pests such as mites which affect the growth of plants. .
In addition, the compound of the present invention is a compound with high safety 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 an insecticide or acaricide.

  The compounds of the present invention show excellent control effects not only on susceptible lines, but also on pests of various resistant lines, and also on mites of acaricide-resistant lines. Examples of the pests of the resistant strain include pests such as diamondback moth, planthoppers, leafhoppers, aphids and the like, which have developed resistance to various existing drugs and can not achieve the efficacy of the existing drugs.

  The compounds of the present invention are excellent in the control effect of ectoparasites that cause harm to 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 an ectoparasite control agent.

  In addition, the compound of the present invention shows efficacy at all developmental stages of the organism to be controlled, and exhibits excellent control effect on, for example, ticks, eggs such as insects, nymphs, larvae, moths and adults.

[Pest control agent, insecticide or acaricide]
The pest control agent, or insecticidal or acaricidal agent of the present invention contains at least one selected from the 6-phenyl nicotinic 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 insecticidal or acaricidal agent of the present invention is not particularly limited as long as the pest control effect is exhibited.

The pest control agent or the insecticidal or acaricidal agent of the present invention is cereals; vegetables; root vegetables; potato plants; florets; fruit trees, houseplants, tea, coffee, trees such as cocoa, grasses; Preferably used for plants such as cotton;
For application to plants, the pest control agent or insecticide or acaricide of the present invention is any of leaves, stems, handles, flowers, buds, fruits, seeds, sprouts, roots, tubers, tubers, shoots, cuttings, etc. It may be used at the site. Also, the pest control agent or the insecticidal or acaricidal agent of the present invention is not particularly limited by the species of the plant to which it is applied. Examples of plant species include: original species, varieties, improved varieties, cultivars, mutants, Hybrids, genetically modified organisms (GMO) and the like can be mentioned.

  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) Butterfly or moth of Lepidoptera
(a) moths of the family Arctiidae, such as Hyphantria cunea, Lemyra imparilis;
(b) moths of the family Bucculatricidae, eg, Bacculatrix pyrivorella;
(c) Carposinidae, eg, Carposina sasakii;
(d) Mosquitoes of the family Rumbaceae (Crambidae), such as the cotton fowl (Diaphania indica) of the species of Diaphania sp. (Diaphania spp.), American black flea deer (Diaphania nitidalis); for example, Ostrinia sp. No. 1 (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), azukinomeiga (Ostrinia scapulalis); others, Chiropodella moth (Cnaphalocrocis medinalis); Diatraea grandiosella), Glyphodes pyloalis, Hyalunella (Hellula undalis), Shibatoga (Parapediasia teterrella);
(e) moths of the family Gelechiidae, such as, for example, immature bug (Helcystogramma triannulella), cotton bedbug (Pectinophora gossypiella), potato leafhopper (Phthorimaea operculella), bacaga (Sitotroga cerealella);
(f) A moth of the family Geometriidae (Geometridae), for example, anemone beetle (Ascotis selenaria);
(g) moths of the family Oscaridae (Gracillariidae), such as, for example, Chanophosoga (Caloptilia theivora), mandarin oranges (Phyllocnistis citrella), kinmonhosoga (Phyllonorycter ringoniella);
(h) A butterfly of the family Hesperiidae (Hesperiidae), eg, Parnaria guttata;
(i) moths of the family Lacasiocampidae (Lasiocampidae), such as Malacosoma neustria;
(j) moths of the family Lymantriidae, for example, of the species Lymantria spp., Lymantria dispar, Lymantria monacha; Other, Euproctis pseudoconspersa, Orgyia thyellina);

(k) moths of the family Molyrigidae (Lyonetidae), such as, for example, Lyonetia clerkella, of the species Lionetia sp. (Lyonetia spp.), Glymone Haemoglyca (Lyonetia prunifoliella malinella);
(l) A moth of Noctidae (eg, Spodoptera spp.), Spodoptera depravata, Southern armyworm (Spodoptera eridania), Spodoptera exigua, Spodoptera frugipergiperda , Spodoptera littoralis, Spodoptera litura; for example, Autographa spp., Autographa gamma, Tamagura nigrisigna, eg Agrotis spp. For example, Agrotis ipsilon, Agrotis segetum; for example, Helicoverpa spig., Helicoverpa armigera, Helicoverpa assulta, cotton ball worm (Helicoverpa zea), for example, Heliochis spp. (Heliothis spp.), Heliothis armigera, Helithis virescens Other; Akadia leucomames (Aedia leucomelas), Mitsumonkin uwaba (Ctenoplusia)
agnata), akebikonoha (Eudocima tyrannus), punctua (Mamestra brassicae), oyster clover (Mythimna separata), オ ビ ガ (Naranga aenescens), キ リ キ リ ((Panolis japonica), セ マ ナ Per (Peridroma ビ ー i ギ ン ia サ) Trichoplusia ni);
(m) A moth of the family Nolidae (Nolidae), eg, Missia oringa (Earias insulana);
(n) A butterfly of the family Piridae (Pieridae), for example, a butterfly (Pieris brassicae) of the genus Piralis sp. (Pieris spp.), a butterfly (Pieris rapae crucivora);
(o) moths of the family Palcellidae (Plutellidae), such as Acrolepiopsis spp., Acrolepiopsis sapporensis, Phyllaceae (Acrolepiopsis suzukiella); and others, Psylola xylostella;
(p) moths of the family Phyllidae (Pyralidae), such as Cadra cautella, Elasmopalpus lignosellus, Etiella zinckenella, H. nov. (Galleria mellonella);
(q) moths of the family Sphingidae (Sphingidae), for example, tomato hornworm (Manduca quinquemaculata), tobacco hornworm (Manduca sexta) of Manduca spp.

(r) Moths of the family Stathmopodidae, for example, Kakinotameta (Stathmopoda masinissa);
(s) moths of the family Trichoidea (Tineidae), for example, moth (Tinea translucens);
(t) A moth of the family Tortricidae (Tortricidae), such as, for example, an Adoxophys spp., a chamomile (Adoxophys honmai), an apple cockerel (Adoxophys orana), for example, an Archips sp. (Archips spp. Of the apple snail (Archips breviplicanus), midarek syllabary (Archips fuscocupreanus); other, the chopped rhinoceros (Choristoneura fumiferana), the codling moth (Cydia pomonella), the grape hosohamaki (Eupoecilia ambiguella), the nasi himi ), Chamon (Homona magnanima), bean legume (Leguminivora glycinivorella), scallop (Lobesia botrana), green-spotted moth (Matsumuraeses phaseoli), Tobihamaki (Pandemis heparana), Tenguhamaki (Sparganothis pilleriana)
(u) A moth of the Sedaceae family (Yponomeutidae), for example, an apple clover (Argyresthia conjugella).

(2) Thysanoptera (Thysanoptera) pests
(a) Of the Phalaethripidae (Phlaeothripidae), such as, for example, Ponticulothrips diospyrosi;
(b) Of the Thripidae (Thripidae), such as, for example, of the flower of the genus Thripidae (Frankliniella spp.), the flowering thrips (Frankliniella intonsa), the flowering thrips (Frankliniella occidentalis); Thrips (Thrips palmi), New Zealand thrips (Thrips tabaci); and the other Croton thrips (Heliothrips haemorrhoidalis), the tea thrips (Scirtothrips dorsalis).

(3) Pest of the stink bug (Hemiptera)
(A) Cerebrospidae (Archaeorrhyncha)
(a) For the planthopper family (Delphacidae), for example, the night-wing plant (Laodelphax striatella), the black-footed planthopper (Nilaparvata lugens), the black-footed planthopper (Perkinsiella saccharicida), the white-tailed deer (Sogatella furcifera).

(B) Cervix suborder (Clypeorrhyncha)
(a) Of the leafhopper family (Cicadellidae), for example, of the Empoasca spp., the potato leafhopper (Empoasca fabae), the leafhopper leafhopper (Empoasca nipponica), the leafhopper leafhopper (Empoasca onukii), Phytohypticus (Empoasca sakaii); Other, Phytohyperglyphus (Arboridia apicalis), Midorhydlowy (Balclutha saltuella), Phytohyperglyphus (Epiacanthus stramineus), Hymenopythofops (Macrosteles striifrons), ).

(C) Hemiptera: Heteroptera
(a) of the family Alydidae, for example, the family Riptortus clavatus;
(b) of the family Helicidae (Coreidae), for example, Crustus punctiger, spider beetles (Leptocorisa chinensis);
(c) of the family of Lymphidae (Lygaeidae), such as, for example, Brysus leukopterus (Blissus leucopterus), Bleuropaniculata (Cavelerius saccharivorus), Bleuropanicta (Togo hemipterus);
(d) For example, black-legged turtles (Halticus insularis), snails (Lygus lineolaris), cotton-free hoppers (Psuedatomoscelis seriatus), black-legged snails (Stenodema sibiricum), red-tailed snails (Stenotus rubibitus) ), Trichonotylus caelestialium;

(e) Of the Pentatomidae (Pentatomidae), for example, of the Nezara species (Nezara spp.), Green-streated bug (Nezara antennata), South- American stink bug (Nezara viridula); such as, for example, the Silver-headed Bug species (Eysarcoris spp.) , Eysarcoris aeneus, Eysarcoris lewisi, Eysarcoris ventralis, and others, Dolycoris baccarum, Eurydema rugosum, Blossy bugs Halyomorpha halys), P. pipisodorus hybneri, P. japonicus (Plautia crossota), S. japonicus (Scotinophora lurida);
(f) of the family of Pyrophocoridae (Pyrrhocoridae), for example, Dysdercus cingulatus;
(g) of the family Rhopalidae, for example, the red locust (Rhopalus msculatus);
(h) of the family Scutelleridae, for example, the wheat bug (Eurygaster)
integraleps);
(i) Of the family Gingambiidae (Tingidae), for example, Nassinbai (Stephanitis nashi).

(D) Rooster (Sternorrhyncha)
(a) Of the Aphididae (Adelgidae), for example, Larch Aphid (Adelges laricis);
(b) Whitefly family (Aleyrodidae), for example, Silversea whitefly (Bemisia argentifolii), B. tabaci (Bemisia tabaci) of Bemisia spp .;
citri), the whitefly (Trialeurodes vaporariorum);
(c) Aphididae (Aphididae), for example, Aphis species (Aphis spp.), Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii , European apple aphids (Aphis pomi), Shrimp Aphids (Aphis sambuci), Aphid spiky aphids (Aphis spiraecola); eg, Rhopalosiphum spp. For example, Diosphis spp., Diosphis plantaginea, Dysphis radicola; eg, Macrossifum spp., Aphis gossypii (Macrosiphum avenae), (Macrosiphum
e.g., of the species of Myzus sp. (Myzus spp.), Aphis gossypii (Myzus cerasi), Momois aphid (Myzus persicae), Aquilinia aphid (Myzus varians); and other Pea aphids (Acyrthosiphon pisum) , Potato beet aphid (Aulachothum solani), moth aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), strawberry prairie aphid (Chaetosiphon fragaefolii), a ladybug aphid (Hyaloputius utili) Japanese radish aphid (Lipaphis erysimi), broad bean aphid (Megoura viciae), blue-toothed aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop buffalo beetle (Phorodonhumuli), green-legged moth Aphids (Sitobion avenae), Komi can aphid (Toxoptera aurantii);

(d) of the family Coccidae (Coccidae), for example of the Ceroplastus sp. (Ceroplastes ceriferus), ruby (Ceroplastes rubens);
(e) Anchovy species (Pseudaulacaspis spp.) of the Marukaididae (Diaspididae), a scaleworm (Pseudaulacaspis pentagona), a scaleworm (Pseudaulacaspis prunicola); for example, Unaspis spp. Of the mealybug (Unaspis euonymi), the mealybug (Unaspis yanonensis); and the other mealybugs (Aonidiella aurantii), the mealworm (Comstockaspis perniciosa), the mealworm (Fiorinia theae); );
(f) Of the cotton meal scale (Margarodidae), for example, a large scale scale beetle (Drosicha corpulenta), an Iceria scale beetle (Icerya purchasi);
(g) of the family Aphididae (Phylloxeridae), for example, the grapevine aphid (Viteus vitifolii);
(h) of the family Pseudococcidae, for example, of the genus Planococcus sp. (Planococcus spp.); , Quackworm (Pseudococcus comstocki);
(i) Of the family Psyllididae, for example, Psylla spp., Psylla mali, Psylla pyrisuga; and others, Psylla pyrisuga;

(4) Insect pests of beetles (Polyphaga)
(a) of the family Anobiidae, eg, tobacco beetle (Lasioderma serricorne);
(b) of the family Attelabidae, for example, Byctiscus betulae, Rhynchichis heros;
(c) of the family Bostrichidae, eg, Lyctus brunneus;
(d) of the family Brentidae (Brentidae), for example, Cylas formicarius;
(e) of the family Buprestidae (Buprestidae), for example, Agrilus sinuatus;
(f) Of the family of Cerambycididae (Cerambycidae), for example, Anodlophora malasiaca, Pinus longicornus (Monochamus alternatus), Pterocarpus longiflorum (Psacothea hilaris), Grapevine longhorned beetle (Xylotrechus pyrrhoderus);
(g) Of the family Chrysomelidae (Chrysomelidae), for example, of the species Burchus spp., pea weevil (Bruchus pisorum), psyllid weevil (Bruchus rufimanus); eg, of the species Diabrotica sp. (Diabrotica spp.), Northern corn Root worm (Diabrotica barberi), Southern corn root worm (Diabrotica undecimpunctata), Western corn root worm (Diabrotica virgifera); eg, Phyllotreta sp. ; Other, ground beetle (Aulacophora femoralis), azuki bean beetle (Callosobruchus chinensis), ground beetle (Cassida nebulosa), brown leaf beetle (Chaetocnema concinna), Colorado potato beetle (Leptinotarsa decemlineata), nematode leaf beetle (Oulema oryzae) Tobihamushi (Psylliodes angusticollis);

(h) Of the ladybird family (Coccinellidae), for example, of the Epilacna sp. (Epilachna spp.), green bean (Epilachna varivestis), red-winged ladybird (Epilachna vigintioctopunctata);
(i) Of the weevil family (Curculionidae), for example, of the Anthonomus species (Anthonomus spp.), cotton weevil (Anthonomus grandis), Anopheles solanacea (Anthonomus pomorum); such as, for example, Sitophilus koscionus species (Sitophilus spp.) , Granary weevil (Sitophilus granarius), Scorpion beetles (Sitophilus zeamais); Other, Echinocnemus squameus, Eusphaerus (Euscepes postfasciatus), Pinus auris beetles (Hylobius abietis), Alfalfa tabaci Lissohoptrus oryzophilus), Anchovy weevil (Otiorhynchus sulcatus), Red-billed Weeping Beetle (Sitona lineatus), Weeping beetle (Sphenophorus venatus);
(j) For example, Maranotus sp. (Melanotus spp.), of the click beetle family (Elateridae), Maranotus fortnumi, Maranotus tamsuyensis;
(k) of the family Kitokiidae (Nitidulidae), for example, Epuraea domina;
(l) Of the Scarabaeidae (Scarabaeidae), for example, of the Anomala species (Anomala spp.), Anomala cuprea, Anomala rufocuprea; Other, Cetonia aurata; ), Nagachakogane (Heptophylla picea), European Crayfish (Melolontha melolontha), Mangoganane (Popillia japonica);
(m) of the bark Beetle family (Scolytidae), for example, the spiny cub (Ips typographus);
(n) of the family Staphylinidae, for example, ascidian (Paederus)
fuscipes);
(o) For example, of the beetle family (Tenebrionidae), for example, Tenebrio molitor, Tricholium castaneum;
(p) of the family Kogroustidae (Trogossitidae), for example Kochnost (Tenebroides mauritanicus).

(5) Pests of the fly (Diptera)
(A) Fly (Brachycera)
(a) of the family Agromyzidae, for example of the species Liriomyza spp., Liriomyza bryoniae; Other, the leafminer fly (Chromatomyia horticola), the rice leafminer fly (Agromyza oryzae);
(b) Seed fly (Delia platura), cabbage fly (Delia radicum) of, for example, Delia species (Delia spp.) of the family Anthomyiidae; other sugar beet (Pegomya cunicularia);
(c) of the Drosophila family, for example, of the genus Drosophila (Drosophila spp.), Drosophila melanogaster, Drosophila melanogaster (Drosophila suzukii);
(d) of the family Ephydridae, for example, the rice leafminer fly (Hydrellia griseola);
(e) of the family Hameolidae (Psilidae), for example, the carrot rust fly (Psila rosae);
(f) Tephritidae (eg, Bactrocera spp.), a fruit fly (Bactrocera cucurbitae), a fruit fly (Bactrocera dorsalis); eg, a species of Lagoletis sp. (Rhagoletis spp.); Rhagoletis cerasi), red-collar fly (Rhagoletis pomonella); Other, fruit fly (Ceratitis capitata), olive fruit fly (Dacus oleae).

(B) mosquitoes (Nematocera)
(a) For example, soybean seed fly (Asphondylia yushimai), sorghum head fly (Contarinia sorghicola), red-spotted fly (Mayetiola destructor), and red-spotted fly (Sitodiplosis mossellana) of the family Cididomyiidae.

(6) Pest of the grasshopper (Orthoptera)
(a) A locustidae (Acrididae), for example, Schistocerca spp., Schistocerca americana, Schistocerca gregaria; Other, Australian bream (Chortoicetes terminifera), Moroccan locust (Dociostaurus maroccanus), Tomasa grasshopper (Locusta migratoria), Brown locust (Locustana pardalina), Red-spotted grasshopper (Nomadacris septemfasciata), Kobaneago (Oxya yezoensis);
(b) of the cricket family (Gryllidae), for example, the European cricket (Acheta domestica), the empress (Teleogryllus emma);
(c), for example, of the family of Grilotalpidae, such as Grilotalpa orientalis;
(d), for example, a clavule (Tachycines asynamorus) of the family Tettigoniidae.

(7) Mites (Acari)
(A) Acarididae (Acaridida)
(a) Acaridae (Acaridae) mites such as, for example, Rhizoglyphus spp., red mites (Rhizoglyphus echinopus), Robin mites (Rhizoglyphus robini); (Tyrophagus neiswanderi), Digella sativa (Tyrophagus perniciosus), Digella sativa (Tyrophagus putrescentiae), Spinach Psyllidia mite (Tyrophagus similis); Others, Acyl

(B) Prestigmata (Prostigmata) mite mites (Actinedida)
(a) Ticks of the spider mite family (Tetranychidae), such as the clover spider mite (Bryobia praetiosa), the false clover spider mite (Bryobia rubrioculus) of the species Briobia spp., for example, the species Eotetranychus spp. Of the red-handed spider mite (Eotetranychus asiaticus), the horned spider mite (Eotetranychus boreus), the green-footed spider mite (Eotetranychus celtis), the giant-skinned spider mite (Eotetranychus geniculatus), the orange-footed spider mite (Eotetranychus kankitus) (Eotetranychus smithi), Suginami spider mite (Eotetranychus suginamensis), Walnut spider mite (Eotetranychus uncatus); Mango -Red mite (Oligonychus mangiferus), Sugar cane red mite (Oligonychus orthius), Avocado red mite (Oligonychus perseae), Red-spotted spider mite (Oligonychus pustulosus), Red spider mite (Oligonychus shinkajii), Todo matsuite ich , Red spider mite (Panonychus citri), black-tailed spider mite (Panonychus mori), apple red spider mite (Panonychus ulmi); , Red spider mite (Tetranychus quercivorus), southern red spider mite (Tetranychus phaselus), red spider mite (Tetranychusurticae), red grub spider mite (Tetranychus viennensis); For example, the green spider mite (Sasanychus akitanus), the green spider spider mite (Sasanychus pusillus) of the green spider mite (Sasanychus spp.); Gothic spider mite (Shizotetranychus longus), Red-footed spider mite (Shizotetranychus miscanthi), Red-tailed spider mite (Shizotetranychus recki), Willow spider mite (Shizotetranychus schizopus);

(b) Mite mites (Tenuipalpidae) mites such as, for example, Brevipulpus species (Brevipalpus spp.), grapevine red spider mite (Brevipalpus lewisi), channoid spider mite (Brevipalpus obovatus), red haired spider mite (Brevipalpus phoenicis), cactus spider lice (Brevipalpus) russulus), red-spotted spider mite (brevipalpus californicus); such as, for example, the genus Tenipalpus sp. (Tenuipalpus spp.), the spider red mite (Tenuipalpus pacificus), the oyster spider mite (Tenuipalpus zhizhilashviliae);
(c) Acarid mites (Eriophyidae) mites, such as Aceria spp., Aceria diospyri, Ficus mondas (Aceria ficus), Clifs mite (Aceria japonica), Monascus mites (Aceria kuko), Carnations Eriophyes chiba mite (Eriophyes chiba mite), for example of the rust mites (Aceria paradianthi), the leafminer mite (Aceria tiyingi), the tulip snail (Aceriatulipae), the fruit fly mite (Aceria zoysiea); for example, of the genus Eriophyes sp. For example, Acropus spp., Tomato rust mite (Aculops lycopersici), immature snail (Aculops pelekassi); for example, Aculus spp., Peach mite (Aculus fockeui), apple rust mite (Aculus schlechtendali) ;; Other, Aphachylla theavagrans, Chanosabida Dice (Calacarus carinatus), grapevine mite (Colomerus vitis), grapevine snail (Calepitrimerus vitis), nasty snail (Epitrimerus pyri), snail (Paraphytoptus kikus), snail (Paracalacarus podocarpi), snail mite (Phylloite)
(d) Tick mites (Transonemidae) mites, such as, for example, the tarsonemus spp. );
(e) Mite mites (Penthaleidae) mites, such as, for example, Penthaleus erythrophalus of the genus Pentareus sp. (Penthaleus spp.), and green mites (Penthaleus major).

  The pest control agent or the insecticide or acaricide of the present invention may contain components other than the compound of the present invention. Other components include known carriers used for formulation and the like. Moreover, as other ingredients, conventionally known fungicides, insecticides / acaricides, nematocides, soil pesticides, plant regulators, herbicides, synergists, fertilizers, soil conditioners, animal feeds And the like. By including such other components, a synergistic effect may be exhibited.

  Specific examples of an insecticide / acaricide, a nematocide, a soil insecticide / acaricide, etc. which can be used in combination or in combination with the pest control agent or the insecticide or acaricide of the present invention are shown below.

(1) Acetylcholinesterase inhibitors:
(a) Carbamate system: Alanicarb, aldiocarb, benzocarb, benfracarb, butocarboxime, butoxy carboxim, carbaryl, carbofuran, carbosulfan, carbohephan, ethiophene carb, fenobucarb, formetanate, furaiocarb, isocarb, methiocarb, methoyl, oxamyl, pyrimicarb, propokisul, Thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MIPC, MPMC, MTMC, aldoxycarb, alixicarb, aminocarb, bufencarb, cloetocarb, metame sodium, promecarb;

  (b) Organophosphorus: Acephate, azamethyphos, azinphos-ethyl, azinphos-methyl, kazzaphos, chlorethoxyphos, chlorphenphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demetone-S-methyl, diazinon, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylphosphine, Disulfoton, EPN, Ethion, Ethoprophos, Pham Fool, Fenamiphos, Fenitrothion, Fenthione, Fosciate, Heptenophos, Imicifoss, Isophenphos, Isocarbophos, Isoxathion, Malathion, Mecarbammethizophos Methiomethone, Monocrotophos, Naredo, Omethoate, Oxydimethone-Methyl, Parathion, Parathion-Methyl, Phentoa , Folate, Phosalone, Phosmet, Phosphamidone, Hoximme, Pirimiphos-Methyl, Profenophos, Propetamphos, Prothiophos, Pyracophos, Pyridaphenthion, Quinalphos, Sulfotep, Tebupillinphos, Temephos, Terbuphos, Tetrachlorvinphos, Thiometon, Triazophos, Trichlorophos, Bromophos; Ethyl, BRP, Carbophenothione, Cyanophenphos, CYAP, Demetone-S-Methylsulfone, Diariphos, Diclofenthion, Dioxabenzophos, Etriphos, Fensulfothion, Flupirazophos, Honophos, Formothion, Phosmethylan, Isazophos, Iodofenphos, Methacrylose, Pirimiphos-ethyl, phosphocarb, propaphos, protoate, sulpropos.

(2) GABA-agonizing chloride ion channel antagonist: acetoprole, chlordane, endosulfan, ethiprole, fipronil, pyrafluprol, pyriprole; campechlor, heptachlor, dienochlor.
(3) Sodium channel modulators: acrolinathrin, d-cis-trans arethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- Cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cypophothrin [(1R) -trans isomer], deltamethrin, enpentrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropothrin, fenvalerate, flucithinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kaly Surin, permethrin, phenothrin [(1R) -trans isomer], prarethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R) -isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II , Profluthrin, dimefluthrin, bioetanomethrin, biopermethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrositrinate, flufenprox, metfluthrin, protrifenbuto, pyrethmethrin, terraretrin.

(4) Nicotinic acetylcholine receptor agonists: Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyrazifron.
(5) Nicotinic acetylcholine receptor allosteric modulators: spinetoram, spinosad.
(6) Chloride channel activators: Abamectin, emamectin benzoate, lepimectin, milbemectin; ivermectin, selamectin, doramectin, eprinomectin, moxidectin, milbemycin, milbemycin oxime, nemadectin.
(7) Juvenile hormone-like substances: hydroprene, quinoprene, mesoprene, phenoxycarb, pyriproxyfen; diofenolan, epofenonan, triprene.
(8) Other nonspecific inhibitors: methyl bromide, chlorpicrin, sulfuryl fluoride, borax, tartaric acid.
(9) Homoptera order selective antifeedants: flonicamide, pimetrodine, pyrifluquinazone.

(10) Acaricide growth inhibitors: clofenthezin, difrobidazine, hexythiazox, etoxazole.
(11) Microorganisms derived from insect midgut inner membrane disrupter: Bacillus thuringiensis subsp. Islaerensis, Bacillus sphaericus, Bacillus thuringiensis subsp. Eiwai, Bacillus thuringiensis subsp. Kurstaki, Bacillus thuringiensis subsp. Teneburionis, Bt Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1 / Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitor: diafenthiuron, azocyclotin, cyhexatin, phenbutatin oxide oxidized, propargite, tetradiphone.
(13) Oxidative phosphorylation uncoupling agent: chlorfenapyr, sulframide, DNOC; binapakryl, dinobuton, dinocup.
(14) Nicotinic acetylcholine receptor channel blocker: bensultap, cartap hydrochloride; nereistoxin; thiosultap monosodium salt, thiocyclam.
(15) Chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxlon, flufenoxuron, hexaflumuron, lufenuron, novallon, noviflumuron, teflubenzurone, triflumuron, buprofezin, fluazulon
(16) Diptera molt-disrupting agents: cyromazine.
(17) Molting hormone receptor agonists: Chromafenozide, halofenozide, methoxyfenozide, tebufenozide.
(18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform.
(19) Mitochondrial electron transport complex III inhibitor: acequinosyl, fluacripyrim, hydramethylnon.
(20) Mitochondrial electron transport complex I inhibitor: phenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrade, tolfenpyrade, rotenone.

(21) Voltage-gated sodium channel blockers: 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 complex II inhibitor: sienopyrafen, ciflumethofen, piflubumide.
(25) Ryanodine receptor modulators: chloranthraniliprole, cyantraniprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed Function Oxidase Inhibitor Compound: Piperonyl butoxide.
(27) Latrophin receptor agonist: Depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoxmate, biphenazate, bromopropilate, quinomethionate, cryolite, dicophor, pyridoryl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, Phenylsobromolate, benzomate, methaldehyde, chlorobenzylate, crothiazobene, dicyclanyl, phenoxacrim, phentrifanyl, flubenziamine, fluphenadine, gossypua, japonirua, methoxadiazon, petroleum, potassium oleate, tetrasul, triaracene, afidopyropene ), Phlomethokine, flufiprole, fluensulphone, meperflusulline, tetramethylfursulin, tralopyril, dimeflusulline, methyl neode Amide, fluraralane, afoxolanel, fluxamethamide, 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) Antiparasitic agent:
(a) Benzimidazole: fenbendazole, albendazole, triclabendazole, oxybendazole, mebendazole, oxfendazole, perbendazole, flubendazole; febantel, netobimine, thiophanate; thiabendazole, cambendazole;
(b) salicylanilides: closantel, oxyclosanide, lafoxanide, niclosamide;
(c) Substituted phenolics: nitroxinyl, nitroscanate;
(d) pyrimidines: pyrantel, morantel;
(e) imidazothiazole system: levamisole, tetramisole;
(f) tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintic agents: cyclodienes, lyanias, chlorthrone, metronidazole, demiditraz; piperazine, diethyl carbamazine, dichlorophen, monetantel, tribenzimidin, amidanter; thiacetalsamide, merolsamine, arsenamide.

Specific examples of fungicides that can be used in combination or in combination with the pest control agent or the insecticide or acaricide of the present invention are shown below.
(1) Nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: Benalaxil, Benalaxyl-M, fralaxyl, metalaxyl, metalaxyl-M; oxadixyl; cloziracone, off-race;
(b) adenosine deaminase inhibitors: bupirimate, dimethymol, ethylimol;
(c) DNA / RNA synthesis inhibitors: hymexazole, octilinone;
(d) DNA topoisomerase II inhibitor: oxophosphate.

(2) Mitotic proliferation inhibitors and cytostatics:
(a) β-tubulin polymerization inhibitor: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole; thiophanate, thiophanate methyl; dietofencarb, zoxamide, etaboxam;
(b) cell division inhibitors: penciclone;
(c) Delocalization inhibitors 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; isofetamide; fluopyram; fenfuram, flumecyclox; carboxin, oxycarboxin; thifluzamide; benzobin diflupyr, bixafen, fluxapiroxade , Flumetopyr, isopyrazam, penflufen, penthiopyrade, sedaxane; boscalid; pyradiflumid;
(c) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, spiderxystrobin, quaxoxystrobin, enoxastrobin, fluphenoxystrobin, picoxystrobin, pyraxtrobin; pyraclostrobin, Crayoxime-methyl, trifloxystrobin; dimoxystrobin, phenaminestrobin, metominostrobin, orysastrobin; famoxadone; fluoxastrobin; phenamidone; pyribencarb; mandestrobin;
(d) Complex III ubiquinol reductase Qi inhibitors: Cyazofamid; amisulbrom;
(e) Uncoupling agent for oxidative phosphorylation: vinapacryl, meptylizino cup, dino cup; fluazinam; ferimzone;
(f) Oxidative phosphorylation inhibitors (inhibitors of ATP synthetase): phentin acetate, phentin chloride, phentin hydrochloride;
(g) ATP production inhibitor: silthiofam;
(h) Complex III: Qx (unknown) inhibitor of cytochrome bc1 (ubiquinone reductase): amethocrazine.

(4) Amino acid and protein synthesis inhibitors
(a) Methionine biosynthesis inhibitors: Andprim, cyprodinil, mepanipyrim, pyrimethanyl;
(b) Protein synthesis inhibitors: Blasticidin-S; Kasugamycin, Kasugamycin hydrochloride; Streptomycin; Oxytetracycline.

(5) Signal transduction inhibitors:
(a) Signal transduction inhibitors: quinoxyfene, proquinazide;
(b) MAP-histidine kinase inhibitors in osmotic signaling: fenpiclonyl, fludioxonil; clozolinate, iprodione, procymidone, vinclozolin.

(6) Lipid and cell membrane synthesis inhibitors:
(a) Phospholipid biosynthesis, methyl transferase inhibitors: Edifenphos, iprovenphos, pyrazophos;
(b) lipid peroxides: biphenyl, chloroneb, dichlorane, quindozen, technazen, tolclophos methyl; etordiazole;
(c) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb bosecetate, prothiocarb;
(d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis D747 strain;
(e) Agents that disrupt cell membranes: extracts of Goseika Jupte (tea tree).

(7) Sterol biosynthesis inhibitor of cell membrane:
(a) Demethylation inhibitors at position C14 in sterol biosynthesis: Trifolin; pyriphenox, pilisoxazole; phenarimol, flulprimidol, nualimol; imazaryl, imazalil sulfate, oxosconazole, peflazoate, prochloraz, triflumisole Azaconazole, Bitartanol, Bromuconazole, Ciproconazole, Diclobutrazol, Difenoconazole, Diniconazole, Diniconazole, Diniconazole-M, Epoxiconazole, Etaconazole, Fenbuconazole, Fluquinonazole, Flusilazole, Flutriaazole, Fluconazole, Fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole Fluquinconazole, simeconazole, tebuconazole, tetraconazole triadimefon, triadimenol, triticonazole; prothioconazole, voriconazole; main phen triflupromazine Kona tetrazole;
(b) Inhibitors of Δ14 reductase and Δ8 → Δ7-isomerase in sterol biosynthesis:
Aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph; fenpropidine, piperaline; spiroxamine;
(c) 3-keto reductase inhibitors at C4 demethylation of sterol biosynthesis system: fenhexamid; fenpyrazamine;
(d) squalene epoxidase inhibitors of sterol biosynthesis system: pyributycarb; naftifine, terbinafine.

(8) Cell wall synthesis inhibition
(a) Trehalase inhibitor: Validamycin;
(b) Chitin synthetase inhibitors: polyoxins, polyoxolims;
(c) Cellulose synthetase inhibitors: Dimethomorph, flumorph, pirimorph; bench abariculum, iprobicarb, tolprocarb, varifenalate; mandipropamide.

(9) Melanin biosynthesis inhibitor
(a) Reductase inhibitors of melanin biosynthesis: fushalides; piroxolone; tricyclazole;
(b) Dehydratase inhibitors of melanin biosynthesis: Carpropamide; diclocimet; phenoxanyl;
(c) Others: Tolprocarb.

(10) Host plant resistance inducer:
(a) Agents that act on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: Probenazole; Thiazinyl; Isotianil; Laminarin;

(11) Agents with unknown activity: Shimoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoloxide, flusulfamide, diclomedin, metasulfocarb, cyfluphenamide, metraphenone, pyrofenone, dodine, dodine free base, flutianil.

(12) Agents having multiple action points: copper (copper salt), Bordeaux solution, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur product, calcium polysulfide; faram, mancozeb, maneb, Mankapper, methylam, polycarbamate, propineb, tilam, zineb, ziram; captan, captaphor, phorpet; chlorothalonil; diclofluanid, tolylfluanid; gazatine, iminoctadine triacetate, iminoctadine albesylate (iminoctadine) trialbesilate); anilazine; dithianone; quinomethionate;

(13) Other agents: DBEDC, fluorophorpet, gazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofram, agrobacteria, betoxazine, diphenylamine, methylisothianate (MITC ), Mildeomycin, Capsaicin, Kuflaneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophen, Diphenzoquat, Diphenzoquat Methylsulfonate, Flumethobel, Fosetyl Calcium, Fosetyl Sodium, Irumamycin, Natamycin, Nitrotal Isopropyl , Oxamocarb, pyrrolnitrin, tebufloquine, tolniphanide, zalliramide, algophase, amicarthiazole (Amicarthiazol), oxathiapiproline (Oxathiapiprolin), methylam zinc, Benzoazole, trichlamide, uniconazole, mildeomycin, Oxyfenthiin, picarbutrazox, picenbutazox, fenpicoxamide, dicloventiazox, quinofumelin.

Specific examples of plant regulators which can be used in combination or in combination with the pest control agent or the insecticide or acaricide of the present invention are shown below.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorphenuron, thidiazuron, chlorphenuron, dihydrozeatin, gibberellin A4, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (alias: abiglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichlorprop, phenothiol, 1 -Naphthylacetamide, ethychlozate, croxifonac, maleic acid hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (-)-jasmonic acid, methyl jasmonate, (+)-strigol, (+) -Deoxystri Lumpur, (+) - Orobankoru, (+) - Sorugorakuton, 4-oxo-4- (2-phenylethyl) amino acid; ethephon, chlormequat, mepiquat chloride, benzyl adenine, 5-aminolevulinic acid.

[Ectoparasite control or control agent]
The ectoparasite control or control 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 control agent of the present invention is excellent in the control effect of ectoparasites that harm animals.

Ectoparasites infect the body and skin of host animals, particularly warm-blooded animals and fish. More specifically, it infests the back of the host animal, underarms, lower abdomen, inner crotch, etc., and ingests and ingests nutrient sources such as blood and dandruff from the animal. The ectoparasites include mites, lice, fleas, mosquitoes, sand fly, lice fly, lice and the like.
Host animals to be treated with the ectoparasite control or control agent of the present invention include companion animals such as dogs and cats; pet birds; domestic animals such as cattle, horses, pigs, sheep and the like; warm-blooded animals such as poultry; Can be mentioned. In addition, fish such as salmon, trout, puffer fish, carp and goldfish; insects such as bees, stag beetles and beetles;
The ectoparasite infests in and on host animals, particularly warm-blooded animals. More specifically, it infests the back of the host animal, underarms, lower abdomen, inner crotch, etc., and ingests and ingests nutrient sources such as blood and dandruff from the animal.

  The ectoparasite control or control agent of the present invention can be applied by known veterinary procedures (topical, oral, parenteral or subcutaneous administration). As a method thereof, a method of orally administering to an animal by tablet, capsule, feed mixing, etc .; a method of administering to an animal by immersion fluid, suppository, injection (intramuscular, subcutaneous, intravenous, intraperitoneal etc.); A method of topically administering an aqueous solution by spraying, pour-on, spot-on, etc .; extrinsic agent for controlling ectoparasites in resin; shaping the mixture into a suitable shape such as a collar, ear tags, etc. Method of wearing and local administration; and the like.

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

(1) Mites (Acari)
Acarid (Dermanyssidae) tick, Macrocarpus snail (Macronys sidae) tick, Scutellaris mite (Laelapidae) mite, Acarididae (Varroidae) mite, Acarididae (Argasidae) mite, Acaridae (Ixodidae) tick (Psoroptidae) mites, Sarcoptidae mites, Trichodermid mites (Knemidokoptidae) ticks, Phytoseiids (Demodixidae) ticks, Trichodermids (Trombiculidae) ticks, insect pests such as stag beetles .
(2) Lice (Phthiraptera)
Lice of the lice of the family Haematopinidae, lice of the family Linognidae, lice of the family Leptocoridae (Menoponidae), the flies of the family Leptophyte family (Philopteridae), the flea of the family Trichodiidae (Trichodictidae).
(3) Flea eyes (Siphonaptera)
Human fleas (Pulicidae) fleas, such as the dog flea species (Ctenocephalides spp.), The dog flea (Ctenocephalides canis), the cat flea (Ctenocephalides felis);
A flea of Tungidae (Tungidae), a flea of Ceramophyllidae (Ceratophyllidae), and a flea of Leptopsyllidae.
(4) Hemiptera (Hemiptera).
(5) Insect pests of the order Diptera (Diptera) mosquitoes, mosquitoes (Simuliidae) moths, Simulaidae snails (Ceratopogonidae) nukakas, Tabanidae snails (Muscidae) flies, flies A fly of the family of Glossinidae, a fly of the family of the fruit fly, a fly of the family of fruit fly (Hippoboscidae), a fly of the family of fly fly (Calliphoridae), a fly of the family of fly fly (Oestridae).

[Control agent for other harmful organisms]
In addition, the control effect of pests that have poisoned needles and venom, which cause damage to animals, pests that mediate various pathogens and pathogens, and pests that cause human discomfort (toxic pests, hygiene pests, unpleasant pests, etc.) Excellent.
Below, the example is shown.
(1) Pests of the Hymenoptera (Hymenoptera) Bees of the family Aphididae (Argidae), bees of the family Aphididae (Cynipidae), bees of the family of wasp (Dypnionidae), bees of the family of Anemones (Diprionidae) Wasp of the hornets (Vespidae).
(2) Other pests Cockroaches (Blattodea), termites (termite), arachnids (Araneae), centipedes (cetipede), rusts (millipede), crustaceans (crustacea), and worms (Cimex lectularius).

[Formulation prescription]
Some formulations of pest control agents, insecticides, acaricides, and ectoparasite control or control agents of the present invention will be shown. However, the present invention is not limited to these formulation examples. The "parts" in the formulation examples are by weight.

  The following shows formulations for agriculture and horticulture and for rice.

Formulation Example 1: Wettable powder
40 parts of the compound of the present invention, 53 parts of diatomaceous earth, 4 parts of higher alcohol sulfuric acid ester, and 3 parts of alkylnaphthalene sulfonate are uniformly mixed and finely ground to obtain a wettable powder with an active ingredient of 40%.

Formulation Example 2 Emulsion
Thirty 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 of 30% of the active ingredient.

Formulation Example 3 Granule
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 ground, and then granulated into particles of 0.5 to 1.0 mm in diameter To obtain granules of 5% active ingredient.

Formulation Example 4 Granules
5 parts of the compound of the present invention, 73 parts of clay, 20 parts of bentonite, 1 part of dioctyl sulfosuccinate sodium salt, and 1 part of potassium phosphate are mixed and ground, water is added thereto, and they are thoroughly mixed. Thus, granules of 5% active ingredient are obtained.

(Preparation Example 5: Suspension)
10 parts of the 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 parts of xanthan gum and 73.8 parts of water are mixed to obtain a particle size of 3 μm or less Wet grinding to obtain a 10% suspension of the active ingredient.

  The formulation of the ectoparasitic agent is shown below.

Formulation Example 6 Granules
5 parts of the compound of the present invention is dissolved in an organic solvent to obtain a solution, the solution is sprayed on 94 parts of kaolin and 1 part of white carbon, and then the solvent is evaporated under reduced pressure to obtain granules. Granules of this type can be used in admixture with animal feed.

Formulation Example 7 Injectable
An injection is obtained by uniformly mixing 0.1 to 1 part of the compound of the present invention and 99 to 99.9 parts of peanut oil and then filter sterilizing with a sterilizing filter.

Preparation Example 8 Pour-on Agent
A pour-on agent is obtained by uniformly mixing 5 parts of the compound of the present invention, 10 parts of myristic 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
One part of the compound of the present invention, 10 parts of propylene glycol and 89 parts of isopropanol are uniformly mixed to obtain a spray.

(Example of compound synthesis)
The present invention will next be described in more detail by way of examples. However, the present invention is not limited at all by the following examples.

Example 1
5- (4- (5-Methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) pyridine Production of -3-carbothioamide

ｔ−ブチルピペラジン−１−カルボキシレート（５．２６ｇ）をアセトン（７０ｍｌ）に溶解させた。これに臭化シアン（３．５９ｇ）を加えて、室温にて１．５時間撹拌した。得られた液に水を注加し、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（３．２４ｇ、収率５４％）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) 3.49-3.52(4H,m),3.16-3.20(4H,m),1.46(9H,s) . (Step 1)
Synthesis of t-butyl 4-cyanopiperazine-1-carboxylate

t-Butyl piperazine-1-carboxylate (5.26 g) was dissolved in acetone (70 ml). To this was added cyanogen bromide (3.59 g) and stirred at room temperature for 1.5 hours. Water was poured into the obtained solution, 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 (3.24 g, yield 54%). The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 3.49-3.52 (4 H, m), 3.16-3. 20 (4 H, m), 1.46 (9 H, s).

ヒドロキシアミン塩酸塩（３．２ｇ）を水（１５ｍｌ）に溶解させた。これに炭酸ナトリウム（８．１２ｇ）を加えた。次いで、それにメタノール（１５ｍｌ）とｔ−ブチル４−シアノピペラジン−１−カルボキシレート（３．２４ｇ）を加えて、２．５時間加熱還流した。得られた液を減圧濃縮し、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（３．４２ｇ、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) 3.35-3.46(5H,m),3.02-3.08(3H,m) . (Step 2)
Synthesis of tert-butyl 4- (N-hydroxy amidine) piperazine-1-carboxylate

Hydroxyamine hydrochloride (3.2 g) was dissolved in water (15 ml). To this was added sodium carbonate (8.12 g). Then, methanol (15 ml) and t-butyl 4-cyanopiperazine-1-carboxylate (3.24 g) were added to it and heated to reflux for 2.5 hours. The resulting solution was concentrated under reduced pressure, 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 (3.42 g, yield 91%). The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 3.35-3.46 (5 H, m), 3.02-3. 08 (3 H, m).

ｔ−ブチル４−（Ｎ−ヒドロキシアミジン）ピペラジン−１−カルボキシレート（２．２７ｇ）をピリジン（２３ｍｌ）に溶解させた。これに無水酢酸（１ｍｌ）を加えて８０℃で３時間撹拌した。得られた液を室温まで冷却し、水に注加し、酢酸エチルで抽出し、飽和食塩水で洗浄し、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、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＝３／１）で精製し、目的化合物（１．０５ｇ、収率４２％）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) 3.48-3.51(4H,m),3.36-3.41(4H,m),2.45(3H,s)1.47(9H,s) . (Step 3)
Synthesis of t-Butyl 4- (5-methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carboxylate

t-Butyl 4- (N-hydroxy amidine) piperazine-1-carboxylate (2.27 g) was dissolved in pyridine (23 ml). Acetic anhydride (1 ml) was added to this, and it stirred at 80 degreeC for 3 hours. The obtained solution was cooled to room temperature, poured into water, extracted with ethyl acetate, washed with saturated brine, and the organic layer 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 = 3/1) to obtain the desired compound (1.05 g, yield 42%) . The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 3.48-3.51 (4 H, m), 3.36-3. 41 (4 H, m), 2. 45 (3 H, s) 1.47 (9 H, s).

ｔ−ブチル４−（５−メチル−１，２，４−オキサジアゾール−３−イル）ピペラジン−１−カルボキシレート（１．０５ｇ）を１，４−ジオキサン（１０ｍｌ）に溶解させた。これに４Ｍ塩酸１，４−ジオキサン溶液（５ｍｌ）を加えて室温にて一晩撹拌した。得られた液を減圧濃縮し、目的化合物（０．８ｇ、収率１００％）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 (CD₃OD,δppm) 3.60-3.66(4H,m),3.26-3.31(4H,m),2.45(3H,s). (Step 4)
Synthesis of 5-methyl-3- (piperazin-1-yl) -1,2,4-oxadiazole

t-Butyl 4- (5-methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carboxylate (1.05 g) was dissolved in 1,4-dioxane (10 ml). To this was added 4 M hydrochloric acid solution in 1,4-dioxane (5 ml), and the mixture was stirred overnight at room temperature. The obtained solution was concentrated under reduced pressure to obtain the target compound (0.8 g, yield 100%). The NMR data of the obtained target compound are shown below.
¹ H-NMR (CD ₃ OD, δ ppm) 3.60-3.66 (4H, m), 3.26-3. 31 (4H, m), 2.45 (3H, s).

５−シアノ−２−（トリフルオロメチル）−６−（４−（トリフルオロメチル）フェニル）ニコチン酸（０．２６ｇ）をジクロロメタン（４ｍｌ）に溶解させた。これに、氷冷下、Ｎ，Ｎ−ジメチルホルムアミド（０．０１ｇ）、および塩化オキサリル（０．１ｍｌ）を加えた。その後、室温にて３０分間撹拌した。得られた液を減圧濃縮し、濃縮液をジクロロメタン（４ｍｌ）に溶解させた。これに５−メチル−３−（ピペラジン−１−イル）−１，２，４−オキサジアゾール（０．１２ｇ）、およびトリエチルアミン（０．４ｍｌ）を加えて室温にて２時間撹拌した。得られた液を減圧濃縮し、濃縮液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＝１／１）で精製し、目的化合物（０．３０ｇ、収率８４％）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) 8.14(3H,m),7.84(2H,d),3.35-3.70(6H,m),3.80-4.07(2H,m)2.50(3H,s). (Step 5)
5- (4- (5-Methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) nicotine Synthesis of nonitrile

5-Cyano-2- (trifluoromethyl) -6- (4- (trifluoromethyl) phenyl) nicotinic acid (0.26 g) was dissolved in dichloromethane (4 ml). To this was added, under ice-cooling, N, N-dimethylformamide (0.01 g) and oxalyl chloride (0.1 ml). Then, it stirred at room temperature for 30 minutes. The resulting solution was concentrated under reduced pressure, and the concentrate was dissolved in dichloromethane (4 ml). To this was added 5-methyl-3- (piperazin-1-yl) -1,2,4-oxadiazole (0.12 g) and triethylamine (0.4 ml) and stirred at room temperature for 2 hours. The obtained solution was concentrated under reduced pressure, and the concentrated solution was purified by silica gel column chromatography (developing solvent: n-hexane / ethyl acetate = 1/1) to obtain the desired compound (0.30 g, yield 84%) . The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 8.14 (3H, m), 7.84 (2H, d), 3.35-3.70 (6H, m), 3.80-4.07 (2H, m) 2.50 (3H, s).

５−（４−（５−メチル−１，２，４−オキサジアゾール−３−イル）ピペラジン−１−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（５０．０ｍｇ）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（３０ｍｇ）、および水硫化ナトリウム（２３ｍｇ）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（５３．０ｍｇ、収率９９％）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(2H,d),7.89(1H,s),7.82(1H,s),7.71(2H,d),7.58(1H,s),3.91-4.00(1H,m),3.71-3.80(1H,m),3.34-3.63(6H,m),2.45(3H,s). (Step 6)
5- (4- (5-Methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) pyridine Synthesis of -3-carbothioamide

5- (4- (5-Methyl-1,2,4-oxadiazol-3-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) nicotine The nitrile (50.0 mg) was dissolved in N, N-dimethylformamide (1 ml). Magnesium chloride hexahydrate (30 mg) and sodium hydrosulfide (23 mg) were added to this, and it stirred at room temperature for 1 hour. Saturated aqueous ammonium chloride solution was poured into the obtained solution, 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 (53.0 mg, yield 99%). The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 8.00 (2H, d), 7.89 (1 H, s), 7.82 (1 H, s), 7.71 (2 H, d), 7.58 (1 H, s), 3.91-4.00 (1 H , m), 3.71-3.80 (1 H, m), 3.34-3. 63 (6 H, m), 2. 45 (3 H, s).

５−（４−（３−クロロピリジン−２−イル）ピペラジン−１−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（５０．０ｍｇ）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（２４ｍｇ）、および水硫化ナトリウム（１９ｍｇ）を加えて室温にて２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（５２．０ｍｇ、収率９７％）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) 8.19(1H,dd),7.98-8.02(3H,m),7.74(2H,d)7.67(1H,s),7.63(1H,dd),7.15(1H,s),6.92(1H,dd),3.86-4.04(2H,m),3.29-3.51(6H,m). Example 2
Preparation of 5- (4- (3-Chloropyridin-2-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) pyridine-3-carbothioamide

N- (5- (4- (3-chloropyridin-2-yl) piperazine-1-carbonyl) -6-trifluoromethyl-2- (4- (trifluoromethyl) phenyl) nicotinonitrile (50.0 mg) was N- , N-dimethylformamide (1 ml) was dissolved. Magnesium chloride hexahydrate (24 mg) and sodium hydrosulfide (19 mg) were added to this, and it stirred at room temperature for 2 hours. Saturated aqueous ammonium chloride solution was poured into the obtained solution, 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 (52.0 mg, yield 97%). The NMR data of the obtained target compound are shown below.
¹ H-NMR (CDCl ₃ , δ ppm) 8.19 (1 H, dd), 7.98-8.02 (3 H, m), 7.74 (2 H, d) 7.67 (1 H, s), 7.63 (1 H, dd), 7.15 (1 H, 7) s), 6.92 (1 H, dd), 3.86-4.04 (2 H, m), 3.29-3. 51 (6 H, m).

Some of the compounds of the present invention prepared in the same manner as the above examples are shown in Table 1. Table 1 shows the substituents of the compounds represented by formula (I-1). In the formula, n represents the number of substituents (X ³ ) on the benzene ring. The column of physical properties in Table 1 shows the melting point (mp). In Table 1, Me represents a methyl group. Arrows indicate bonding positions.

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

(Preparation of emulsion for test)
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 alkyl aryl ether were mixed and dissolved to prepare Emulsion (I) of 5% of active ingredient.
98.6 parts by weight of dimethylformamide and 1.4 parts by weight of polyoxyethylene alkyl aryl ether were mixed and dissolved to prepare Emulsion (II) containing no active ingredient.

(Test Example 1) Efficacy test against the oyster sprouts 0.8 g of a commercially available artificial feed (Insector LFS, manufactured by Nippon Agro-Industrial Co., Ltd.) and 1 μl of emulsion (I) were mixed to obtain a test feed (I). What filled 0.2 g of test feed (I) for test in a plastic test container (1.4 ml volume) was set as a test section.
0.8 g of a commercially available artificial feed (Insector LFS, manufactured by Nippon Agro-Industrial Co., Ltd.) and 1 μl of the emulsion (II) were mixed to obtain a test feed (II). A plastic test container (1.4 ml) filled with 0.2 g of test feed (II) was used as a control.
Two testicular and 2nd instar larvae were inoculated respectively in the test area and control area containers and sealed with a plastic lid. They were placed in a constant temperature chamber at 25 ° C., and on the 5th day, the insecticidal rate and food consumption were examined. The test was performed in duplicate.
The compound No. B-3 was tested for efficacy against the carob. The compound had an insecticidal rate of 100% against the oyster spider. In addition, the intake of the test area was 10% or less of the intake of the control area.

(Test Example 2) Efficacy test against Kanzawa spider mite On the green bean primary leaves, five female adults of Kanzawa spider mite from Okayama Prefecture were inoculated. Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm to obtain a drug. This drug was sprayed on the green beans and allowed to air dry. Thereafter, it was placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%. Ten days after the application, ticks were checked for life and death. The test was performed in duplicate.
The compound No. B-1, B-2 and B-4 were tested for efficacy against Kanzawa spider mite. All compounds showed an insecticidal rate of 90% or more. Green beans grew well without dying.

(Test Example 3) Efficacy test against the spider spider mite A kidney bean was raised in a 3 inch bowl, and 8 primary female spider spider spider spider spider spider spider spider spider spider mites from Aomori prefecture were inoculated on primary leaves. Emulsion (I) was diluted with water to a concentration of the compound of the present invention of 125 ppm. The diluted solution was sprayed on the beans. The beans were placed in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 65%. Ten days after the application, ticks were checked for life and death. The test was performed in duplicate.
The compound No. B-1, B-2, B-4 and B-5 were tested for efficacy against the spider spider mite. All compounds showed an insecticidal rate of 90% or more. The green beans grew well without dying.

  Since compounds selected at random among the compounds of the present invention exert the effects as described above, the compounds of the present invention, including compounds which could not be exemplified, are pest control, particularly insecticidal, acaricidal, ectoparasitic It can be understood that the compound has an effect such as insect control or control, does not cause phytotoxicity on plants, and is a compound having little toxicity to human and fish and environmental impact.

Claims (6)

The compound represented by Formula (I), or its salt.

(In the 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 represents 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 C6-10 aryl group, or a substituted or unsubstituted group And a 5- to 6-membered heteroaryl group of
Q represents a cyclic amino group represented by formula (II). )

(In the formula (II), the arrow indicates a bonding position,
X represents a substituent on a cyclic amino group and is a halogeno group, or a substituted or unsubstituted C1-6 alkyl group,
n represents the number of X and is an integer from 0 to 4;
Y ^a represents a substituted or unsubstituted phenyl group, a substituted or unsubstituted 5-membered heteroaryl group, or a substituted or unsubstituted 6-membered heteroaryl group. ) The compound according to claim 1, or a salt thereof, wherein R ¹ is a substituted or unsubstituted thiocarbamoyl group. The compound according to claim 1 or 2, or a salt thereof, wherein Y ^a is a substituted or unsubstituted 5-membered heteroaryl group.   The pest control agent which contains as an active ingredient at least 1 chosen from the group which consists of a compound as described in any one of Claims 1-3, and its salt.   The insecticide or acaricide which contains at least 1 chosen from the group which consists of a compound as described in any one of Claims 1-3, and its salt as an active ingredient.   An ectoparasite control or control agent comprising, as an active ingredient, at least one selected from the group consisting of a compound according to any one of claims 1 to 3 and a salt thereof.