JP2023077429A - Benzamide compounds and pest control agent - Google Patents

Abstract

To provide: benzamide compounds which have excellent pest control activity, particularly insecticidal activity and/or acaricidal activity, are excellent in safety, and can be synthesized industrially favorably; and pest control agents comprising the same as active ingredients.SOLUTION: Provided are compounds including, as a representative example, 4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carbonyl)-4',5-bis(trifluoromethyl)-[1,1'-biphenyl]-2-carbonitrile.SELECTED DRAWING: None

Description

The present invention relates to benzamide compounds and pesticides. More specifically, the present invention provides a benzamide compound that has excellent insecticidal activity and/or acaricidal activity, is excellent in safety, and can be industrially advantageously synthesized, and a pest control agent containing the same as an active ingredient. concerning

As a compound structurally related to the benzamide compound of the present invention, Patent Document 1 discloses a compound represented by the following formula (A) or (B). These compounds are indicated for use in insecticidal and acaricidal agents.

WO2015/032280A1

An object of the present invention is to provide a benzamide compound that has excellent pesticidal activity, particularly insecticidal activity and/or acaricidal activity among them, is excellent in safety, and can be industrially advantageously synthesized, and a harmful compound containing the same as an active ingredient. To provide a biocontrol agent.

〔式（I）中、
Ａｒは、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示し、
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、ハロゲノ基、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
Ｒ⁴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、置換若しくは無置換のＣ１～６アルコキシ基、またはシアノ基を示し、
Ｑは、式（Qa）または式（Qb）で表わされる基を示す。

前記式（Qa）および式（Qb）中、
矢印は結合位置を示し、
ｐ¹は、括弧内のメチレンの数を示し且つ０または１であり、
ｐ²は、括弧内のメチレンの数を示し且つ０～２のいずれかの整数であり、
Ｘ¹は、環上の置換基を示し、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アルキルスルホニルオキシ基、または置換若しくは無置換のＣ１～６アルキルチオ基であり、
ｍは、Ｘ¹の数を示し且つ化学的に許容される０～４のいずれかの整数であり、
Ｘ²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、
Ｙは、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ６～１０アリール基、または置換若しくは無置換の５～６員ヘテロアリール基を示し、
Ｙ’は、置換若しくは無置換のＣ１～６アルキル基、置換若しくは無置換のＣ１～６アルキルスルホニル基、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員ヘテロアリール基を示す。〕 As a result of investigations to solve the above problems, the present invention including the following aspects has been completed.
(1) A compound represented by formula (I) or a salt thereof.

[In formula (I),
Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl 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 halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group;
R ⁴ represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group;
Q represents a group represented by formula (Qa) or formula (Qb).

In the above formulas (Qa) and (Qb),
Arrows indicate binding positions,
p ¹ indicates the number of methylenes in the parentheses and is 0 or 1;
p ² indicates the number of methylenes in the parentheses and is an integer from 0 to 2,
X ¹ represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6 an alkylthio group,
m represents the number of X ¹ and is any chemically acceptable integer from 0 to 4,
X 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,
Y represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group;
Y' is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl indicates a group. ]

(2) A pest control agent containing, as an active ingredient, at least one selected from the group consisting of the compounds described in (1) above and salts thereof.
(3) An insecticide or acaricide containing, as an active ingredient, at least one selected from the group consisting of the compounds described in (1) above and salts thereof.
(4) An ectoparasite control or extermination agent containing, as an active ingredient, at least one selected from the group consisting of the compounds described in (1) above and salts thereof.

INDUSTRIAL APPLICABILITY The benzamide compound of the present invention can control agricultural crops and pests that pose problems in terms of hygiene. In particular, agricultural pests and mites can be effectively controlled at lower concentrations. Furthermore, ectoparasites that harm humans and animals can be effectively controlled.

[Benzamide compound]
The benzamide 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 present invention, the term "unsubstituted" means only scaffolding groups. When only the name of the base group is used without mentioning "substituted", it means "unsubstituted" unless otherwise specified.
On the other hand, the term "substituted" means that one of the hydrogen atoms in the mother nucleus group is replaced with a group (substituent) having the same or different structure as that of the mother nucleus. Thus, a "substituent" is another group attached to a scaffold group. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.

A term such as “C1-6” indicates that the number of carbon atoms in the mother nucleus group is from 1 to 6, and the like. This number of carbon atoms does not include the number of carbon atoms in substituent groups. For example, an ethoxybutyl group is classified as a C2 alkoxy C4 alkyl group because the base group is a butyl group and the substituent is an ethoxy group.

A "substituent" is not particularly limited as long as it is chemically acceptable and has the effects of the present invention.
Specific examples of groups that can be "substituents" include the following groups.
Halogeno groups such as fluoro, chloro, bromo and iodo groups;
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 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 and 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 of;
C3-8 cycloalkyl groups such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cubanyl group;
2-cyclopropenyl group, 2-cyclopentenyl group, 3-cyclohexenyl group, C3-8 cycloalkenyl group such as 4-cyclooctenyl group;
C6-10 aryl group such as phenyl group and naphthyl group;
3- to 6-membered heterocyclyl group;

hydroxyl group; oxo group;
C1-6 alkoxy groups such as methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy and t-butoxy;
C2-6 alkenyloxy groups such as a vinyloxy group and an allyloxy group;
C2-6 alkynyloxy groups such as an ethynyloxy group and a propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
3- to 6-membered heterocyclyloxy group;
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 C1-6 alkoxy groups such as methoxymethoxy group and ethoxymethoxy group;

Carboxyl group;
formyl group; C1-6 alkylcarbonyl group such as acetyl group and propionyl group;
formyloxy group; C1-6 alkylcarbonyloxy groups such as acetyloxy group, propionyloxy group, n-propylcarbonyloxy group, i-propylcarbonyloxy group;
Methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, C1-6 alkoxycarbonyl group such as 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, perfluoropropan-2-yl group, 1-fluoro-n-butyl group, C1-6 haloalkyl groups such as 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 and 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 1,1-difluorocyclopropyl group and 3,3-difluorocyclobutyl group;
difluoromethoxy group, trifluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, 2,2,3,3,3-pentafluoropropoxy group, 4, C1-6 haloalkoxy groups such as 4,4-trifluorobutoxy group and (1,1,1,3,3,3-hexafluoropropan-2-yl)oxy group;
C2-6 haloalkenyloxy groups such as 2-chloropropenyloxy group and 3-bromobutenyloxy group;
C1-6 haloalkylcarbonyl groups such as chloroacetyl group, trifluoroacetyl group and trichloroacetyl group;

cyano group; nitro group; amino group;
C1-6 alkylamino groups such as a methylamino group, a dimethylamino group, and a diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
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 alkylsulfoxyimino groups such as S,S-dimethylsulfoxyimino groups;

carbamoyl group; N'-hydroxycarbamimidoyl group;
C1-6 alkylaminocarbonyl groups such as a methylaminocarbonyl group, a dimethylaminocarbonyl group, an ethylaminocarbonyl group and an 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 alkoxyimino) C1-6 alkyl groups such as a methoxyiminomethyl group and (1-methoxyimino) ethyl group;
(C1-6 alkylcarbonyloxyimino) C1-6 alkyl groups such as an acetoxyiminomethyl group;

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

triC1-6 alkylsilyl groups such as a trimethylsilyl group, a triethylsilyl group, and a t-butyldimethylsilyl group;
a tri-C6-10 arylsilyl group such as a triphenylsilyl group;
In addition, any hydrogen atom in these "substituents" may be substituted with a group having a different structure.

Further, the above-mentioned "3- to 6-membered heterocyclyl group" means that 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom ), that is, a group generated by removing one hydrogen atom from any ring atom of a “3- to 6-membered heterocyclyl compound”.
The above-mentioned "3- to 6-membered heterocyclyl group" means "a 3- to 6-membered heterocyclyl group containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring member atoms. It can also be expressed as “base”.
Heterocyclyl groups can be either monocyclic or polycyclic. As long as at least one ring of the polycyclic heterocyclyl group is a heterocyclic ring, the remaining rings may be saturated alicyclic, unsaturated alicyclic or aromatic rings. The "3- to 6-membered heterocyclyl group" includes a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclyl group, and the like. .

The 3- to 6-membered saturated heterocyclyl group includes an aziridinyl group, an epoxy group, a pyrrolidinyl group, a tetrahydrofuranyl group, a thiazolidinyl group, a piperidyl group, a piperazinyl group, a morpholinyl group, a dioxolanyl group, and a dioxanyl group.

Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. can be mentioned.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, and a triazinyl group.

[Ar]
In formula (I), Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl group.
The “C6-10 aryl group” for Ar is a group formed by removing one hydrogen on the ring of a monocyclic or polycyclic aromatic hydrocarbon. Examples of the C6-10 aryl group include a phenyl group and a naphthyl group, preferably a phenyl group.

The “5- to 6-membered heteroaryl group” of Ar means that 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom are ring-constituting atoms (sometimes referred to as ring member atoms .), that is, a group formed by removing one hydrogen atom from any ring atom of a “5- to 6-membered heteroaryl compound”.
The above-mentioned “5- to 6-membered heteroaryl group” means “a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring member atoms. It can also be expressed as "heteroaryl group".
Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. can be mentioned.
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, and a triazinyl group.

The substituent (may be referred to as X ³ ) on the "C6-10 aryl group" or "5- to 6-membered heteroaryl group" for Ar includes a 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 5-6 membered heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5- to 6-membered heteroaryloxy group, group represented by R ^a R ^b N—CO—, group represented by R ^c CONR ^d — , a hydroxyl group, a nitro group, or a cyano group.

Examples of the “halogeno group” which is one of X ³ include a fluoro group, a chloro group, a bromo group and an iodine group.

A “C1-6 alkyl group” which is one of X ³ may be linear or branched. Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

The "C2-6 alkenyl group" which is one of X ³ includes vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2 -propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group , 1-hexenyl group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group and 5-hexenyl group.

The "C2-6 alkynyl group" which is one of X ³ includes ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2 -propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group , 1-hexynyl group, 1,1-dimethyl-2-butynyl group, and the like.

The "C1-6 alkoxy group" which is one of X ³ includes methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, 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 X ³ 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 X ³ include an acetyl group and a propionyl group.

The "C1-6 alkoxycarbonyl group" which is one of X ³ includes a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, a t-butoxycarbonyl group and the like.

"C1-6 alkylthio group" which is one of X ³ includes methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, etc. can be done.

Examples of the "C1-6 alkylsulfinyl group" which is one of X ³ include methylsulfinyl group, ethylsulfinyl group, t-butylsulfinyl group and the like.

Examples of the "C1-6 alkylsulfonyl group" which is one of X ³ include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.

X ³ "C1-6 alkyl group", "C2-6 alkenyl group", "C2-6 alkynyl group", "C1-6 alkoxy group", "C2-6 alkenyloxy group", "C1-6 alkyl carbonyl group", "C1-6 alkoxycarbonyl group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", or "C1-6 alkylsulfonyl group", preferably a fluoro group, halogeno groups such as chloro, bromo and iodo groups; methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, s-butoxy, i-butoxy and t-butoxy C1-6 alkoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1-6 haloalkoxy group such as trifluoromethoxy group; C6-10 aryl group such as phenyl group and naphthyl group; cyano group; can be mentioned.

The "C3-8 cycloalkyl group" which is one of the substituents on the "C6-10 aryl group" or "5- to 6-membered heteroaryl group" includes cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl groups, cycloheptyl groups, and the like.

Examples of the “C6-10 aryl group” which is one of X ³ include a phenyl group and a naphthyl group.

The "5- to 6-membered heteroaryl group" which is one of X ³ includes a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, and a triazolyl group. , an oxadiazolyl group, a thiadiazolyl group, a tetrazolyl group and the like; a 6-membered ring heteroaryl group such as a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group and a triazinyl group; and the like.

Examples of the “C6-10 aryloxy group” which is one of X ³ include a phenoxy group and a naphthoxy group.

Examples of the "5- to 6-membered heteroaryloxy group" which is one of X ³ include 5- to 6-membered heteroaryloxy groups such as a thiazolyloxy group and a pyridyloxy group.

X ³ "C3-8 cycloalkyl group", "C6-10 aryl group", "5- to 6-membered heteroaryl group", "C6-10 aryloxy group" or "5- to 6-membered Preferred substituents on the heteroaryloxy group include halogeno groups such as fluoro, chloro, bromo and iodo groups; methyl, ethyl, n-propyl, i-propyl, n-butyl, C1-6 alkyl groups such as s-butyl group, i-butyl group, t-butyl group, n-pentyl group, n-hexyl group; chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro- C1-6 haloalkyl groups such as n-propyl group, 1-fluoro-n-butyl group and perfluoro-n-pentyl group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, C1-6 alkoxy groups such as s-butoxy group, i-butoxy group and t-butoxy group; C1-6 haloalkoxy groups such as 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group and trifluoromethoxy group group; cyano group; and the like.

In the “group represented by R ^a R ^b N—CO—” which is one of X ³ , R ^a represents a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group, R ^b is hydrogen represents an atom or a C1-6 alkyl group, and R ^a and R ^b together may form a C3-6 alkylene group.

The "C1-6 alkyl group" for R ^a and R ^b includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Examples of "C1-6 alkoxy group" include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like. can.

Examples of the "C3-6 alkylene group" formed by R ^a and R ^b together include a trimethylene group, a tetramethylene group and a pentamethylene group.

The group represented by R ^a R ^b N--CO-- includes a carbamoyl group, an N-methylaminocarbonyl group, an N,N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy- N-methylaminocarbonyl group, pyrrolidine-1-carbonyl group and the like can be mentioned.

In the “group represented by R ^c CONR ^d —” which is one of X ³ , R ^c represents a C1-6 alkyl group and R ^d represents a hydrogen atom or a C1-6 alkyl group.
Examples of the "C1-6 alkyl group" for R ^c and R ^d include those specifically exemplified for R ^a and R ^b .
Examples of the group represented by R ^c CONR ^d — include an acetamide group and an N-methylacetamide group.

Among these, the substituents on the "C6-10 aryl group" or "5- to 6-membered heteroaryl group" for Ar include a halogeno group, a substituted or unsubstituted C1-6 alkyl group (more preferably C1-6 alkyl group optionally substituted with a halogeno group), substituted or unsubstituted C1-6 alkoxy group (more preferably C1-6 alkoxy group optionally substituted with a halogeno group), substituted or unsubstituted A C1-6 alkylthio group (more preferably a C1-6 alkylthio group optionally substituted with a halogeno group) or a cyano group are preferred.

[R ¹ , R ² , R ³ , R ⁴ ]
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) represents a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.
R ⁴ in formula (I) represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group.

Examples of the "substituted thiocarbamoyl group" for R ¹ include mono- or di-C1-6 alkyl-substituted thiocarbamoyl groups such as methylthiocarbamoyl group, dimethylthiocarbamoyl group and ethyl(methyl)thiocarbamoyl group.
The “halogeno group”, “substituted or unsubstituted C1-6 alkyl group” and “substituted or unsubstituted C1-6 alkoxy group” for R ² , R ³ and R ⁴ are those specifically exemplified for Ar. The same can be said of them.

[Q]
Q represents a group represented by formula (Qa) or formula (Qb).

[Formula (Qa)]
In formula (Qa), the arrow indicates the binding position.
In formula (Qa), p ¹ represents the number of methylenes in the parentheses and is 0 or 1, preferably 1, p ² represents the number of methylenes in the parentheses and any integer of 0 to 2 and preferably 1.

A group of formula (Qa) is represented by formula (Qa-1) when p ¹ is 1 and P ² is 1.

In formula (Qa) or (Qa-1), X ¹ represents a substituent on the ring, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyl an oxy group or a substituted or unsubstituted C1-6 alkylthio group, m represents the number of X ¹ and is any integer from 0 to 4 (preferably 0), X ² is 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.

The "halogeno group", "substituted or unsubstituted C1-6 alkyl group" and "substituted or unsubstituted C1-6 alkylthio group" for X ¹ are the same as those specifically exemplified for Ar. be able to.

Examples of the "C1-6 alkylsulfonyloxy group" for X ¹ include a methylsulfonyloxy group, an ethylsulfonyloxy group, a t-butylsulfonyloxy group and the like.
Preferred substituents on the "C1-6 alkylsulfonyloxy group" include halogeno groups such as fluoro, chloro, bromo and iodo groups.

The “halogeno group”, “substituted or unsubstituted C1-6 alkyl group” and “substituted or unsubstituted C1-6 alkoxy group” for X ² are the same as those specifically exemplified for Ar. be able to.
X ² preferably represents a hydrogen atom, a halogeno group, a hydroxyl group, or a substituted or unsubstituted C1-6 alkoxy group.

In formula (Qa) or (Qa-1), Y is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered hetero ring represents an aryl group.

(1) The “C1-6 alkyl group” for Y may be linear or branched. Alkyl groups include methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group and t-butyl group. , i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Preferred substituents on the "C1-6 alkyl group" in Y include a halogeno group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C1-6 alkylthio group, a C1-6 alkylsulfinyl group, a C1- 6 alkylsulfonyl group, C1-6 haloalkylthio group, C1-6 haloalkylsulfinyl group, C1-6 haloalkylsulfonyl group, substituted or unsubstituted C6-10 aryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5- to 6-membered heteroaryl group, substituted or unsubstituted 5- to 6-membered heteroaryloxy group, C1-6 alkylcarbonyl group, C1-6 alkoxycarbonyl group, R ^a R ^b N- a group represented by R ^a R ^b N--CO-- a group represented by R ^a R ^b N--SO ₂ -- a group represented by R ^c CONR ^d -- R ^c SO ₂ a group represented by NR ^d --, a group represented by R ^e ON=CR ^f --, or a cyano group.

Specifically, halogeno groups such as a fluoro group, a chloro group, a bromo group, and an iodine group; a hydroxyl group; -butoxy group, C1 ~ 6 alkoxy group such as t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1 ~ 6 haloalkoxy group such as trifluoromethoxy group; methylthio group, ethylthio C1-6 alkylthio groups such as groups; C1-6 alkylsulfinyl groups such as methylsulfinyl group and ethylsulfinyl group; C1-6 alkylsulfonyl groups such as methylsulfonyl group and ethylsulfonyl group; trifluoromethylthio group, 2,2, C1-6 haloalkylthio groups such as 2-trifluoroethylthio group; C1-6 haloalkylsulfinyl groups such as trifluoromethylsulfinyl group and 2,2,2-trifluoroethylsulfinyl group; trifluoromethylsulfonyl group, 2, C1-6 haloalkylsulfonyl group such as 2,2-trifluoroethylsulfonyl group; halo-substituted, trifluoromethyl-substituted or unsubstituted C6-10 such as phenyl group, 4-chlorophenyl group and 4-trifluoromethylphenyl group aryl group; halo-substituted, trifluoromethyl-substituted, or unsubstituted C6-10 aryloxy group such as phenyloxy group, 4-chlorophenyloxy group, 4-trifluoromethylphenyloxy group; halo-substituted, C1-6 alkyl-substituted , trifluoromethyl-substituted or unsubstituted 5- to 6-membered heteroaryl group (preferably oxadiazolyl group); halo-substituted, C1-6 alkyl-substituted, trifluoromethyl-substituted or unsubstituted 5- to 6-membered ring heteroaryloxy group (preferably pyridyloxy group); acetyl group, C1-6 alkylcarbonyl group such as propionyl group; methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, t- C1-6 alkoxycarbonyl groups such as butoxycarbonyl group; and cyano group.

In the "group represented by R ^a R ^b N-" which is one of preferred substituents on the "C1-6 alkyl group", R ^a is a hydrogen atom, a C1-6 alkyl group or a C1-6 alkoxy group and R ^b represents a hydrogen atom or a C1-6 alkyl group, and R ^a and R ^b may together form a C3-6 alkylene group.

The "C1-6 alkyl group" for R ^a and R ^b includes methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group, t-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Examples of "C1-6 alkoxy group" include methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group and the like. can.

Examples of the "C3-6 alkylene group" formed by R ^a and R ^b together include a trimethylene group, a tetramethylene group and a pentamethylene group.

Groups represented by R ^a R ^b N— include amino group, N-methylamino group, N,N-dimethylamino group, N-ethyl-N-methylamino group and N-methoxy-N-methylamino group. , pyrrolidin-1-yl group and the like.

In the "group represented by R ^a R ^b N--CO--" which is one of preferred substituents on the "C1-6 alkyl group", R ^a and R ^b have the same meanings as above.
The group represented by R ^a R ^b N--CO-- includes a carbamoyl group, an N-methylaminocarbonyl group, an N,N-dimethylaminocarbonyl group, an N-ethyl-N-methylaminocarbonyl group, and an N-methoxy- N-methylaminocarbonyl group, pyrrolidine-1-carbonyl group and the like can be mentioned.

In the "group represented by R ^a R ^b N--SO ₂ --" which is one of preferred substituents on the "C1-6 alkyl group", R ^a and R ^b have the same meanings as above.
The groups represented by R ^a R ^b N--SO ₂ -- include sulfamoyl group, N-methylaminosulfonyl group, N,N-dimethylaminosulfonyl group, N-ethyl-N-methylaminosulfonyl group, N-methoxy -N-methylaminosulfonyl group, pyrrolidin-1-ylsulfonyl group and the like.

In the “group represented by R ^c CONR ^d —” which is one of preferred substituents on the “C1-6 alkyl group”, R ^c represents a C1-6 alkyl group, and R ^d is a hydrogen atom or Indicates a C1-6 alkyl group.
Examples of the "C1-6 alkyl group" for R ^c and R ^d include those specifically exemplified for R ^a and R ^b .
Examples of the group represented by R ^c CONR ^d — include an acetamide group and an N-methylacetamide group.

In the "group represented by R ^c SO ₂ NR ^d --" which is one of preferred substituents on the "C1-6 alkyl group", R ^c and R ^d have the same meanings as above.
Examples of the group represented by R ^c SO ₂ NR ^d — include a methylsulfonamide group and an N-methylmethylsulfonamide group.

In the "group represented by R ^e ON=CR ^f -" which is one of preferred substituents on the "C1-6 alkyl group", R ^e represents a C1-6 alkyl group, and R ^f is , represents a hydrogen atom or a C1-6 alkyl group.
Examples of the "C1-6 alkyl group" for R ^e and R ^f include those specifically exemplified for R ^a and R ^b .
Examples of the group represented by R ^e ON=CR ^f - include (methoxyimino)methyl group, (ethoxyimino)methyl group, (methoxyimino)ethyl group and (ethoxyimino)ethyl group. .

(2) The “C6-10 aryl group” for Y is a group formed by removing one hydrogen from a monocyclic or polycyclic aromatic hydrocarbon ring. Examples of the C6-10 aryl group include a phenyl group and a naphthyl group, preferably a phenyl group.

The substituents on the C6-10 aryl group include 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, a 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 5-6 membered heteroaryl group, substituted or unsubstituted C6-10 aryloxy group, substituted or unsubstituted 5-6 membered heteroaryloxy group, hydroxyl group , a nitro group, or a cyano group.
Specific examples of these are the same as those exemplified for Ar.

(3) The “5- to 6-membered heteroaryl group” for Y is a nitrogen atom, an oxygen atom and a sulfur atom. ) is a group generated by removing one hydrogen atom from any ring atom of a 5- to 6-membered cyclic aromatic compound, that is, a “5- to 6-membered heteroaryl compound” .
The above-mentioned "5- to 6-membered heteroaryl group" means "a 5- to 6-membered ring containing 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as ring member atoms. It can also be expressed as "heteroaryl group".
Five-membered heteroaryl groups include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl, oxadiazolyl, thiadiazolyl, and tetrazolyl groups. can be mentioned.
A pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridadinyl group, a triazinyl group, etc. can be mentioned as a 6-membered heteroaryl group.
Examples of substituents on the 5- to 6-membered heteroaryl group include the same substituents on the C6-10 aryl group as described in (2).

[Formula (Qb)]
In formula (Qb), the arrow indicates the binding position.
In formula (Qb), p ¹ represents the number of methylenes in the parenthesis and is 0 or 1, preferably 1, p ² represents the number of methylenes in the parenthesis and any integer of 0 to 2 and preferably 1.

A group of formula (Qb) is represented by formula (Qb-1) when p ¹ is 1 and P ² is 1.

In formula (Qb) or (Qb-1), X ¹ and m have the same meanings as X ¹ in formula (Qa) above.

In formula (Qb) or (Qb-1), Y' is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group.

As the "substituted or unsubstituted C1-6 alkyl group", "substituted or unsubstituted C6-10 aryl group", and "substituted or unsubstituted 5- to 6-membered heteroaryl group" in Y', Y The same ones as those specifically exemplified in can be mentioned.

Examples of the "C1-6 alkylsulfonyl group" for Y' include methylsulfonyl group, ethylsulfonyl group, t-butylsulfonyl group and the like.
Substituents on the "C1-6 alkylsulfonyl group", preferably fluoro group, chloro group, bromo group, halogeno group such as iodo group; methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n- C1-6 alkoxy groups such as butoxy group, s-butoxy group, i-butoxy group, t-butoxy group; 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group, C1- such as trifluoromethoxy group 6-haloalkoxy group; C6-10 aryl group such as phenyl group and naphthyl group; cyano group;

Salts of compound (I) are not particularly limited as long as they are agriculturally and horticulturally acceptable salts. 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; salts of transition metals; and salts of organic bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine.

Compound (I) or a salt of compound (I) is not particularly limited by its production method. Also, a 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 Examples and the like.

INDUSTRIAL APPLICABILITY The benzamide compound of the present invention (hereinafter sometimes referred to as the "compound of the present invention") is excellent in controlling harmful organisms such as various agricultural pests and mites that affect plant growth.
In addition, the compounds of the present invention are highly safe compounds because they do not cause phytotoxicity to crops and have low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of insecticides or acaricides.

Furthermore, in recent years, many insect pests, such as diamondback moths, planthoppers, leafhoppers, and aphids, have developed resistance to various existing pesticides, causing the problem of insufficient efficacy of these pesticides. ing. The compounds of the present invention exhibit excellent control effects not only on susceptible strains, but also on various resistant strains of insect pests and miticide-resistant strains of mites.

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

In addition, the compounds of the present invention exhibit efficacy in all developmental stages of organisms to be controlled, and exhibit excellent control effects on, for example, eggs, nymphs, larvae, pupae, and adults of mites, insects, and the like.

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

The pesticides or insecticides or acaricides of the present invention include grains; vegetables; root crops; potatoes; flowers; genus; preferably used for plants such as cotton.
In application to plants, the pesticides or insecticides or acaricides of the present invention are applied to any of the leaves, stems, stems, flowers, buds, fruits, seeds, sprouts, roots, tubers, tuberous roots, shoots, cuttings and the like. May be used for parts. In addition, the pest control agent or insecticide or acaricide of the present invention is not particularly limited by the plant species to which it is applied. Hybrids, genetically modified organisms (GMO) and the like are included.

The pest control agent of the present invention can be used for seed treatment, foliage application, soil application, water surface application, etc. 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) butterflies or moths of the order Lepidoptera
(a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(b) moths of the family Bucculatricidae, such as Bucculatrix pyrivorella;
(c) Carposinidae, for example, Carposina sasakii;
(d) Crambidae moths, such as Diaphania spp., Diaphania indica, Diaphania nitidalis; for example, Ostrinia spp. , corn borer (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Azuki corn borer (Ostrinia scapulalis); Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapedia teterrella;
(e) Moths of the Gelechiidae family, for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthorimaea operculella, Sitotroga cerealella;
(f) moths of the Geometridae family, such as Ascotis selenaria;
(g) moths of the Gracilariidae family, such as Caloptilia theivora, Phyllocnistis citrella, and Phyllonorycter ringoniella;
(h) butterflies of the family Hesperiidae, such as Parnara guttata;
(i) Lasiocampidae moths, such as Malacosoma neustria;
(j) Moths of the family Lymantriidae, such as Lymantria spp., Lymantria dispar, Lymantria monacha; others, Euproctis pseudoconspersa, Orgyia thyellina);

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

(r) moths of the family Stathmopodidae, such as Stathmopoda masinissa;
(s) Moths of the family Tineidae, such as Tinea translucens;
(t) Tortricidae moths, e.g. Adoxophyes spp., Adoxophyes honmai, Adoxophyes orana; e.g. Archips spp. ), Archips breviplicanus, Archips fuscocupreanus; others, Choristoneura fumiferana, Cydia pomonella, Eupoecilia ambiguella, Grapholitha molesta ), Homona magnanima, Leguminivora glycinivorella, Lobesia botrana, Matsumuraeses phaseoli, Pandemis heparana, Sparganothis pilleriana;
(u) Moths of the family Yponomeutidae, such as Argyrestia conjugella.

(2) Thysanoptera pests
(a) Phlaeothripidae, such as Ponticulothrips diospyrosi;
(b) Thripidae, e.g., Frankliniella spp., Frankliniella intonsa, Frankliniella occidentalis; e.g., Thrips spp., Southern yellow Thrips (Thrips palmi), Thrips tabaci; others, Croton thrips (Heliothrips haemorrhoidalis), Tea thrips (Scirtothrips dorsalis).

(3) Hemiptera pests
(A) Archaeorrhyncha
(a) Delphacidae, such as Laodelphax striatella, Nilaparvata lugens, Perkinsiella saccharicida, and Sogatella furcifera.

(B) Clypeorrhyncha
(a) Cicadellidae, for example, Empoasca spp. Empoasca fabae, Empoasca nipponica, Empoasca onukii, Green bean leafhopper Leafhopper (Empoasca sakaii); Other Leafhopper (Arboridia apicalis), Green Leafhopper (Balclutha saltuella), Leafhopper (Epiacanthus stramineus), Leafhopper (Macrosteles striifrons), Leafhopper (Nephotettix cinctinceps) ).

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

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

(D) Sternorrhyncha
(a) of the Adelgidae family, for example, Adelges laricis;
(b) Aleyrodidae, for example, Bemisia spp., Bemisia argentifolii, Bemisia tabaci; Others, Aleurocanthus spiniferus, Dialeurodes
citri), whitefly (Trialeurodes vaporariorum);
(c) Aphididae, e.g. Aphis spp., Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis gossypii , Aphis pomi, Aphis sambuci, Aphis spiraecola; e.g. Rhopalosiphum spp., Rhopalosiphum madis, Rhopalosiphum padi; Dysaphis plantaginea, Dysaphis radicola of Dysaphis spp.; e.g. Macrosiphum avenae, tulip aphid of Macrosiphum spp. (Macrosiphum
euphorbiae); e.g. Myzus spp., Myzus cerasi, Myzus persicae, Myzus varians; others, Acyrthosiphon pisum , potato aphid (Aulacorthum solani), wheatgrass aphid (Brachycaudus helichrysi), radish aphid (Brevicoryne brassicae), strawberry woolly aphid (Chaetosiphon fragaefolii), peach aphid (Hyalopterus pruni), aphid aphid (Hyperomyzus lactucae), SE Radish aphid (Lipaphis erysimi), fava bean aphid (Megoura viciae), wheat aphid (Metopolophium dirhodum), lettuce aphid (Nasonovia ribis-nigri), hop aphid (Phorodonhumuli), wheat green aphid (Schizaphis graminum), barley aphid aphids (Sitobion avenae), aphids (Toxoptera aurantii);

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

(4) Pests of the suborder Polyphaga
(a) Anobiidae, for example, Lasioderma serricorne;
(b) Attelabidae, for example, Byctiscus betulae, Rhynchites heroes;
(c) Bostrichidae, for example, Lyctus brunneus;
(d) of the family Brentidae, for example, Cylas formicarius;
(e) Buprestidae family, for example, Agrilus sinuatus;
(f) Cerambycidae, such as Anoplophora malasiaca, Monochamus alternatus, Psacothea hilaris, and Xylotrechus pyrrhoderus;
(g) Chrysomelidae, e.g., Bruchus spp., Bruchus pisorum, Bruchus rufimanus; e.g., Diabrotica spp., northern corn Rootworm (Diabrotica barberi), Southern Corn Rootworm (Diabrotica undecimpunctata), Western Corn Rootworm (Diabrotica virgifera); ); Others, Aulacophora femoralis, Callosobruchuschinensis, Cassida nebulosa, Chaetocnema concinna, Leptinotarsa decemlineata, Oulema oryzae, Eggplant eggplant Spring beetle (Psylliodes angusticollis);

(h) Coccinellidae, for example, Epilachna spp., Epilachna varivestis, Epilachna vigintioctopunctata;
(i) of the Curculionidae family, e.g., Anthonomus spp., Anthonomus grandis, Anthonomus pomorum; e.g., Sitophilus spp. , granary weevils (Sitophilus granarius), maize weevil (Sitophilus zeamais); Lissohoptrus oryzophilus);
(j) Elateridae, for example, Melanotus spp., Melanotus fortnumi, Melanotus tamsuyensis;
(k) Nitidulidae, for example, Epuraea domina;
(l) Scarabaeidae, such as Anomala spp., Anomala cuprea, Anomala rufocuprea; other Cetonia aurata, Gametis jucunda ), Heptophylla picea, Melolontha melolontha, Popillia japonica;
(m) Scolytidae, for example, Ips typographus;
(n) Staphylinidae, such as Paederus
fuscipes);
(O) Tenebrionidae (Tenebrionidae), for example, Tenebrio molitor, Tribolium castaneum;
(p) Of the family Trigossitidae, for example, Tenebroides mauritanicus.

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

(B) Nematocera
(a) Cecidomyiidae, such as Asphondylia yushimai, Contarinia sorghicola, Mayetiola destructor, and Sitodiplosis moselana.

(6) Pests of the order Orthoptera
(a) of the Acrididae family, such as Schistocerca spp., Schistocerca americana, Schistocerca gregaria; (Dociostaurus maroccanus);
(b) cricket family (Gryllidae), for example, European domestic cricket (Acheta domestica), Emma cricket (Teleogryllus emma);
(c) of the family Gryllotalpidae, such as Gryllotalpa orientalis;
(d) Tettigoniidae, such as Tachycines asynamorus.

(7) Mites (Acari)
(A) Acaridida of Astigmata
(a) Mites of the family Acaridae, such as Rhizoglyphus echinopus, Rhizoglyphus robini of the spp. Rhizoglyphus spp.; (Tyrophagus neiswanderi), Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; lyphus fungivorus);

(B) Actinedida of Prostigmata
(a) mites of the Tetranychidae family, e.g. Bryobia spp., Bryobia praetiosa, Bryobia rubrioculus; e.g. Eotetranychus spp. , Eotetranychus asiaticus, Eotetranychus boreus, Eotetranychus celtis, Eotetranychus geniculatus, Eotetranychus kankitus, Eotetranychus pruni, Eotetranychus shii, Smith Spider mites (Eotetranychus smithi), Eotetranychus suginamensis, Eotetranychus uncatus; Oligonychus mangiferus, Oligonychus orthius, Oligonychus perseae, Oligonychus pustulosus, Oligonychus shinkajii, Oligonychus ununguis; .) of Tetranychus spp., Tetranychus cinnabarinus, Tetranychus evansi, Tetranychus spp. kanzawai), Tetranychus ludeni, Tetranychus quercivorus, Tetranychus phaselus, Tetranychusurticae, Tetranychus viennensis; corpuzae ), Aponychus firmianae; For example, Sasanychus spp. Sasanychus akitanus, Sasanychus pusillus; For example, Shizotetranychus spp. Shizotetranychus celarius, Shizotetranychus longus, Shizotetranychus miscanthi, Shizotetranychus recki, Shizotetranychus schizopus; others, Tetranychina harti, Tuckerella pavo niformis), Caus spider mite (Yezonychus sapporensis);

(b) mites of the family Tenuipalpidae, such as Brevipalpus spp., Brevipalpus lewisi, Brevipalpus obovatus, Brevipalpus phoenicis, Brevipalpus russulus), brevipalpus californicus; for example, Tenuipalpus spp., Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae;
(c) Mites of the family Eriophyidae, such as Aceria spp., Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, carnation Aceria paradianthi, Aceria tiyingi, Aceriatulipae, Aceria zoysiea; e.g. Eriophyes chibaensis, Eriophyes emarginatae of Eriophyes spp. ); e.g., Aculops spp., Aculops lycopersici, Aculops pelekassi; e.g., Aculus spp., Aculus fockeui, Aculus schlechtendali ); other Acaphylla theavagrans, Calacarus carinatus, Colomerus vitis, Calepitrimerus vitis, Epitrimerus pyri, Paraphytoptus kikus, Paracalacarus podocarpi ), Phyllocotruta citri;
(d) mites of the family Transonemidae, such as Tarsonemus spp., Tarsonemus bilobatus, Tarsonemus waitei; Others, Phytonemus pallidus, Polyphagotarsonemus latus )；
(e) mites of the family Penthaleidae, for example Penthaleus erythrocephalus, Penthaleus major of Penthaleus spp.

The pest control agent or insecticide or acaricide of the present invention may contain ingredients other than the compound of the present invention. Other components include known carriers used for formulation. In addition, as other ingredients, conventionally known fungicides, insecticides/miticides, nematicides, soil pesticides, plant regulators, herbicides, synergists, fertilizers, soil conditioners, animal feeds etc. can be mentioned. A synergistic effect may be produced by containing such other components.

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

(1) Acetylcholinesterase inhibitors:
(a) carbamates: alanicarb, aldicarb, bendiocarb, benfuracarb, butocaboxim, butoxycarboxime, carbaryl, carbofuran, carbosulphane, ethiofencarb, fenocarb, formethanate, furatiocarb, isoprocarb, methiocarb, methomyl, oxamyl, pirimicarb, propoxur, thiodicarb, thiophanox, triazamate, trimetacarb, XMC, xylylcarb, phenothiocarb, MTMC, aldoxycarb, arixicarb, aminocarb, bufencarb, chloetocarb, metam sodium, promecarb;

(b) Organophosphorus: Acephate, Azamethyphos, Azinphos-ethyl, Azinphos-methyl, Cadusaphos, Chlorethoxyphos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinon, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Disulfotone, EPN, Ethion, Ethoprophos, Famfur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imisiaphos, Isofenphos, Isocarbophos, Isoxathion, Malathion, Mecarbam, Methamidophos, Methidathion, Mevinphos, monocrotophos, naled, omethoate, oxydimeton-methyl, parathion, parathion-methyl, phenthoate, folate, fosarone, phosmet, phosphamidone, phoxime, pirimiphos-methyl, profenophos, propetamphos, prothiophos, pyraclophos, pyridafenthion, quinarphos, sulfotep, tebupyrinphos, Temephos, terbufos, tetrachlorbinphos, thiometone, triazophos, trichlorfon, vamidothion, bromophos ethyl, carbophenothion, cyanofenphos, demeton-S-methylsulfone, dialiphos, diclofenthion, dioxabenzophos, etrimphos, fensulfothion, flupyrazophos , honophos, formothion, fosmethylan, isazophos, iodofenphos, methacrifos, pirimiphos-ethyl, phosphocarb, propafos, protoate, sulprofos.

(2) GABA-operated chloride ion channel antagonists: acetoprol, chlordane, endosulfan, ethiprol, fipronil, pyrafluprole, pyriprol; campfechlor, heptachlor, dienochlor.
(3) sodium channel modulators: acrynathrin, d-cis-transallethrin, d-transallethrin, 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, cyphenothrin [(1R)-trans isomer], deltamethrin, empentrin [(EZ)-( 1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, cadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrum, resmethrin, silafluofen, tefluthrin, tetramethrin [(1R)-isomer], tralomethrin, transfluthrin, allethrin, pyrethrin, pyrethrin I, pyrethrin II, profluthrin, dimefluthrin, bioethanomethrin, bio permethrin, transpermethrin, fenfluthrin, fenpyritrin, flubrocitrinate, flufenprox, metofruthrin, protrifenbut, pyrethmethrin, terarethrin.

(4) Nicotinic acetylcholine receptor agonists: acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, nitiazine, thiacloprid, thiamethoxam, sulfoxaflor, nicotine, flupyradifuron.
(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, methoprene, fenoxycarb, pyriproxyfen, diophenolan, epofenonane, triprene.
(8) Other non-specific inhibitors: methyl bromide, chloropicrin, sulfuryl fluoride, borax, tartar emetic.
(9) Homoptera selective antifeedants: flonicamid, pymetrozine, pyrifluquinazone.

(10) Mite growth inhibitors: Clofentezine, Diflovidazine, Hexythiazox, Etoxazole.
(11) Microorganism-derived insect midgut lining-disrupting agent: Bacillus thuringiensis subsp. Crop proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/Cry35Ab1.
(12) Mitochondrial ATP biosynthetic enzyme inhibitors: diafenthiuron, azocyclotin, cyhexatin, fenbutatin oxide, propargite, tetradifone.
(13) Oxidative phosphorylation uncouplers: chlorfenapyr, sulflumide, DNOC, binapacryl, dinobutone, dinocap.
(14) nicotinic acetylcholine receptor channel blockers: bensultap, cartap hydrochloride, nereitoxin, thiosultap-sodium salt, thiocyclam.
(15) chitin synthesis inhibitors: bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, triflumuron, buprofezin, fluazuron.
(16) Diptera Molting Disruptor: Cyromazine.
(17) Moulting hormone receptor agonists: Chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide.
(18) Octopamine receptor agonists: amitraz, demiditraz, chlordimeform.
(19) mitochondrial electron transport chain complex III inhibitors: acequinosyl, fluacrypyrim, hydramethylnon, bifenazate.
(20) mitochondrial electron transport chain complex I inhibitors: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad, tolfenpyrad, rotenone.

(21) voltage-gated sodium channel blockers: indoxacarb, metaflumizone.
(22) Acetyl-CoA carboxylase inhibitors: spirodiclofen, spiromesifen, spirotetramat, spiropidione.
(23) mitochondrial electron transport chain complex IV inhibitors: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide.
(24) mitochondrial electron transport chain complex II inhibitors: cyenopyrafen, cyflumetofen, piflubumide.
(25) ryanodine receptor modulators: chlorantraniliprole, cyantraniliprole, flubendiamide, cyclaniliprole, tetraniliprole.
(26) Mixed-function oxidase inhibitor compounds: piperonyl butoxide.
(27) latrophilin receptor agonists: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside.
(28) Other agents (mechanism of action unknown): azadirachtin, benzoximate, bromopropylate, cryolite, dicofol, pyridalyl, benclothiaz, sulfur, amidoflumet, 1,3-dichloropropene, DCIP, phenisobromolate , benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanil, phenoxacrime, fentriphanil, flubenzimine, fluphenazine, gossip lua, japonylua, methoxadiazon, petroleum, sodium oleate, tetrasulfur, triaracene, aphidopyropen, flometquin, Flufiprole, fluenesulfone, meperfluthrin, tetramethylfluthrin, tralopyril, dimefluthrin, methylneodecanamide, fluralaner, afoxolaner, fluxametamide, 5-[5-(3,5-dichlorophenyl)-5-trifluoromethyl-4, 5-Dihydroisoxazol-3-yl]-2-(1H-1,2,4-triazol-1-yl)benzonitrile (CAS: 943137-49-3), Brofuranilide, Triflumezopyrim, Dichloromezothiaz , oxazosulfyl and other metadiamides.

(29) Anthelmintic:
(a) Benzimidazoles: Fenbendazole, Albendazole, Triclabendazole, Oxibendazole, Mebendazole, Oxfendazole, Perbendazole, Flubendazole, Febantel, Netobimin, Thiophanate, Thiabendazole, Cambendazole;
(b) Salicylanilides: Closantel, Oxyclozanide, Rafoxanide, Niclosamide;
(c) substituted phenolics: nitroxynil, nitroscanate;
(d) pyrimidines: pyrantel, morantel;
(e) imidazothiazoles: levamisole, tetramisole;
(f) tetrahydropyrimidines: praziquantel, epsiprantel;
(g) Other anthelmintics: cyclodiene, liania, clorsulon, metronidazole, demiditraz, piperazine, diethylcarbamazine, dichlorophen, monepantel, tribendimidine, amidantel, thiacetalsamide, merolusamine, arsenamide.

Specific examples of fungicides that can be mixed or used together with the pest control agent or insecticide or acaricide of the present invention are shown below.
(1) nucleic acid biosynthesis inhibitors:
(a) RNA polymerase I inhibitors: benalaxyl, benalaxyl-M, furalaxyl, metalaxyl, metalaxyl-M, oxadixyl, clodilacone, offrace;
(b) adenosine deaminase inhibitors: bupirimate, dimethylmol, ethylimole;
(c) DNA/RNA synthesis inhibitors: Hymexazole, Octilinone;
(d) DNA topoisomerase II inhibitors: oxolinic acid.

(2) mitotic inhibitors and cytostatic agents:
(a) beta-tubulin polymerization inhibitors: benomyl, carbendazim, chlorphenazole, fuberidazole, thiabendazole, thiophanate, thiophanate-methyl, diethofencarb, zoxamide, ethaboxam;
(b) a cytostatic agent: pencycuron;
(c) delocalized inhibitors of spectrin-like proteins: fluopicolide.

(3) respiratory inhibitors:
(a) Complex I NADH oxidoreductase inhibitors: Diflumetrim, Tolfenpyrad;
(b) complex II succinate dehydrogenase inhibitors: benodanil, flutolanil, mepronil, isofetamide, fluopyram, fenfuram, flumeciclox, carboxin, oxycarboxin, thifluzamide, benzovindiflupyr, bixafen, fluxapyroxad , furametpyr, isopyrazam, penflufen, penthiopyrad, sedaxane, boscalid, pyraziflumide;
(c) complex III ubiquinol oxidase Qo inhibitors: azoxystrobin, commoxystrobin, comethoxystrobin, enoxastrobin, flufenoxystrobin, picoxystrobin, pyraoxystrobin, pyraclostrobin, pyrametostrobin, triclopiricarb, cresoxime-methyl, trifloxystrobin, dimoxystrobin, phenaminestrobin, metminostrobin, orysastrobin, famoxadone, fluoxastrobin, fenamidone, pyribencarb, mandestrobin;
(d) complex III ubiquinol reductase Qi inhibitors: cyazofamid, amisulbrom;
(e) uncouplers of oxidative phosphorylation: binapacryl, meptyldinocap, dinocap, fluazinam, ferimzone;
(f) oxidative phosphorylation inhibitors (inhibitors 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: andoprim, cyprodinil, mepanipyrim, pyrimethanil;
(b) protein synthesis inhibitors: blasticidin-S, kasugamycin, kasugamycin hydrochloride, streptomycin, oxytetracycline.

(5) signaling inhibitor:
(a) signaling inhibitors: quinoxifene, proquinazide;
(b) MAP and histidine kinase inhibitors in osmotic signaling: fenpicronil, fludioxonil, clozolinate, iprodione, procymidone, vinclozolin.

(6) Lipid and Cell Membrane Synthesis Inhibitors:
(a) phospholipid biosynthesis, methyltransferase inhibitors: edifenphos, iprobenphos, pyrazophos, isoprothiolane;
(b) lipid peroxidants: biphenyl, chloroneb, dichlorane, quintozene, technazene, tolclofosmethyl, etridiazole;
(c) agents acting on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarb fosetylate, prothiocarb;
(d) Microorganisms that disrupt pathogen cell membranes: Bacillus subtilis, Bacillus subtilis strain QST713, Bacillus subtilis strain FZB24, Bacillus subtilis strain MBI600, Bacillus subtilis strain D747;
(e) Cell Membrane Disrupting Agents: Extracts of Gosseikajeupte (Tea Tree).

(7) cell membrane sterol biosynthesis inhibitors:
(a) C14 demethylation inhibitors in sterol biosynthesis: Trifolin, Pyrifenox, Pyrisoxazole, Fenarimol, Flurprimidol, Nuarimol, Imazalil, Imazalil Sulfate, Oxpoconazole, Pefurazoate, Prochloraz, Triflumizole , biniconazole, azaconazole, bitertanol, bromconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, epoxiconazole, etaconazole, fenbuconazole, fluquinconazole, flusilazole, flutriafol, fluconazole, fluconazole-cis, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanil, penconazole, propiconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, prothioconazole, voriconazole, mefen trifluconazole;
(b) inhibitors of Δ14 reductase and Δ8→Δ7-isomerase in sterol biosynthesis:
aldimorph, dodemorph, dodemorph acetate, fenpropimorph, tridemorph, fenpropidin, piperaline, spiroxamine;
(c) 3-ketoreductase inhibitors in C4 demethylation of sterol biosynthesis: fenhexamide, fenpyrazamine;
(d) Squalene epoxidase inhibitors of the sterol biosynthesis system: piributicarb, naftifine, terbinafine.

(8) cell wall synthesis inhibition
(a) a trehalase inhibitor: validamycin;
(b) chitin synthase inhibitors: polyoxins, polyoxolims;
(c) cellulose synthase inhibitors: dimethomorph, flumorph, pirimorph, bentiavalicarb, iprovalicarb, tolprocarb, valifenalate, mandipropamide.

(9) Melanin biosynthesis inhibitor
(a) reductase inhibitors of melanin biosynthesis: fthalide, pyroquilone, tricyclazole;
(b) dehydrogenase inhibitors of melanin biosynthesis: carpropamide, diclocimet, phenoxanyl.

(10) host plant resistance inducer:
(a) agents acting on the salicylic acid synthesis pathway: acibenzolar-S-methyl;
(b) Others: Probenazole, tiazinyl, isotianil, laminarin, and extract of Oitadori.

(11) Agents of unknown activity: cymoxanil, fosetylaluminum, phosphoric acid (phosphate), tecloftalam, triazoxide, fursulfamide, diclomedine, metasulfocarb, cyflufenamide, metrafenone, pyriophenone, dodine, dodine free base, flutianil.

(12) agents with multiple sites of action: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur products, calcium polysulfide, farbum, mancozeb, maneb, Mankappa, metiram, polycarbamate, propineb, thiram, zineb, ziram, captan, captafol, folpet, chlorothalonil, dichlorofluanide, tolylfluanide, guazatine, guazatine acetate, iminoctadine triacetate, iminoctadine albecil Iminoctadine trialbesilate, anilazine, dithianone, quinomethionate, fluorimide.

(13) Other agents: DBEDC, fluorofolpet, bis(8-quinolinolato)copper(II), propamidine, chloropicrin, ciproflam, agrobacterium, betoxazine, diphenylamine, methylisocyanate (MITC), mildeomycin , capsaicin, cufraneb, cyprosulfamide, dazomet, debacarb, dichlorophen, difenzoquat, difenzoquat methylsulfonate, flumetovel, fosetyl calcium, fosetyl sodium, irmamycin, natamycin, nitrothal isopropyl, oxamocarb, pyrrole nitri Tebufuroquine, Tolnifanide, Zariramide, Algophase, Amicarthiazol, Oxathiapiprolin, Zinc Methiram, Benthazole, Triclamide, Uniconazole, Oxyfenthiin, Picarbutrazox (picarbutrazox), Fenpicoxamid, dichlobentiazox, Quinofumelin.

Specific examples of plant regulators that can be mixed or used in combination with the pesticides or insecticides or acaricides of the present invention are shown below.
1-methylcyclopropene, 2,3,5-triiodobenzoic acid, IAA, IBA, MCPA, MCPB, 4-CPA, 5-aminolevulinic acid hydrochloride, 6-benzylaminopurine, abscisic acid, abiglycine hydrochloride, ancimium Dole, butrualine, calcium carbonate, calcium chloride, calcium formate, calcium peroxide, lime sulfur, calcium sulfate, chlormequat chloride, chloropropham, choline chloride, cloprop, cyanamide, cyclanilide, daminozide, decyl alcohol, dichlorprop , dikeglac, dimethipine, diquat, ethephon, eticlozate, flumetralin, flurprimidol, forchlorphenuron, gibberellin A, gibberellin A3, hymexazole, inabenfide, isoprothiolane, kinetin, maleic hydrazide, mefluidide, mepiquat chloride, oxidized glutathione, Paclobutrazol, pendimethalin, prohexadione calcium, prohydrojasmon, pyraflufen-ethyl, syntophen, 1-naphthalene sodium acetate, sodium cyanate, streptomycin, thidiazuron, tripentenol, tribufos, trinexapac-ethyl, Uniconazole P, 1-naphthylacetamide.

[Ectoparasite Control or Pesticide]
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 harm humans and animals.

Ectoparasites live inside and on the skin of host animals, particularly warm-blooded animals and fish. Specifically, it lives in the host animal's back, armpit, lower abdomen, inner thigh, etc., and obtains nutrients such as blood and dander from the animal. Ectoparasites include mites, lice, fleas, mosquitoes, stable flies, flesh flies, sea lice, and the like.
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 cattle, horses, pigs and sheep; are mentioned. Other examples include fish such as salmon, trout, blowfish, carp, and goldfish; insects such as bees, stag beetles, and beetles;
Ectoparasites live in and on host animals, especially warm-blooded animals. Specifically, it lives in the host animal's back, armpit, lower abdomen, inner thigh, etc., and obtains nutrients such as blood and dander from the animal.

The ectoparasite control or extermination agent of the present invention can be applied by known veterinary techniques (topical, oral, parenteral or subcutaneous administration). Methods of administration include tablets, capsules, or mixed feed to animals orally; immersion solutions, suppositories, injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.); A method of locally administering an aqueous solution by spraying, pour-on, spot-on, etc.; kneading an ectoparasite control agent into a resin, molding the kneaded product into a suitable shape such as a collar or ear tag, and applying it to an animal A method of wearing and administering locally;

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 ticks, Macronyssidae ticks, Laelapidae ticks, Varroidae ticks, Argasidae ticks, Ixodidae ticks, Dirtid mites Insect-parasitic mites such as Psoroptidae mites, Sarcoptidae mites, Knemidokoptidae mites, Demodixidae mites, Trombiculidae mites, Stag beetles .
(2) Phthiraptera
Lice of the family Haematopinidae, lice of the family Linognathidae, lice of the family Menoponidae, lice of the family Philopteridae, and lice of the family Trichodectidae.
(3) Siphonaptera
Fleas of the family Pulicidae, such as Ctenocephalides canis, Ctenocephalides felis of Ctenocephalides spp.;
A flea of the family Tungidae, a flea of the family Ceratophyllidae, and a flea of the family Leptopsyllidae.
(4) Hemiptera
(5) pests of the Diptera family Culicidae mosquitoes, Simuliidae blackflies, Ceratopogonidae gnats, Tabanidae horseflies, Muscidae flies, flies of the family Glossinidae, flies of the family Glossinidae, flies of the family Hippoboscidae, flies of the family Calliphoridae, and flies of the family Oestridae.

[Control agent for other harmful organisms]
In addition, it is effective in controlling pests that have poisonous needles and poisonous liquids and damage humans and animals, pests that transmit various pathogens and pathogens, and pests that make people uncomfortable (toxic pests, sanitary pests, unpleasant pests, etc.). Excellent for
Specific examples are shown below.
(1) Hymenoptera pests Argidae bees, Cynipidae bees, Diprionidae bees, Formicidae ants, Mutillidae bees, A bee of the Vespidae family.
(2) Other pests Blattodea, termites, Araneae, cetipede, millipedes, crustacea, Cimex lectularius.

[Formulation formulation]
Some formulation examples of pesticides, insecticides, acaricides, and ectoparasite control or extermination agents of the present invention are given. However, the present invention is not limited to these formulation examples. "Parts" and "%" in the formulation examples are based on mass.

Formulations for agricultural and horticultural use 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 and 3 parts of alkylnaphthalenesulfonate are uniformly mixed and finely pulverized to obtain a wettable powder containing 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 alkylallyl ether are mixed and dissolved to obtain an emulsion containing 30% 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. to obtain granules containing 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 dioctylsulfosuccinate sodium salt, and 1 part of potassium phosphate are mixed and pulverized, water is added and kneaded well, then granulated and dried. to obtain granules containing 5% active ingredient.

(Formulation Example 5: Suspension agent)
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 until the particle size is 3 μm or less. Wet mill to obtain a 10% active ingredient suspension.

The formulation of the ectoparasite control agent is shown below.

(Formulation Example 6: Granules)
5 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. Granules of this kind can be used by mixing them with animal feed.

(Formulation Example 7: Infusion)
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 filtered and sterilized through a sterilizing filter to obtain an infusion.

(Formulation Example 8: Pour-on agent)
5 parts of the compound of the present invention, 10 parts of myristic acid ester and 85 parts of isopropanol are uniformly mixed to obtain a pour-on agent.

(Formulation Example 9: Spot-on agent)
A spot-on agent is obtained by uniformly mixing 10 to 15 parts of the compound of the present invention, 10 parts of palmitate and 75 to 80 parts of isopropanol.

(Formulation Example 10: Spray)
1 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)
EXAMPLES Next, the compounds of the present invention will be described more specifically with reference to examples. However, the present invention is by no means limited by the following examples.

(Example 1)
4-(4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carbonyl)-4′,5-bis(trifluoromethyl)-[1,1′-biphenyl ] -2-Production of carbonitrile

2-Cyano-4′,5-bis(trifluoromethyl)-[1′,1-biphenyl]-4-carboxylic acid (0.14 g) was dissolved in dichloromethane (4 ml) and 1-(3- dimethylaminopropyl)-3-ethylcarbodiimide (97 mg), 1-hydroxybenzotriazole (69 mg), 5-methyl-3-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride (0. 10 g) and triethylamine (0.22 ml) were added and stirred overnight at room temperature. 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=1/1) to obtain the target compound (0.17 g). Yield 87%.
¹ H-NMR (CDCl ₃ , δppm) 7.68-7.85(6H,m), 4.59-4.66(1H,m), 3.45-3.49(1H,m), 3.19-3.28(3H,m), 2.58(3H, s), 2.16-2.22(1H,m), 1.75-2.05(3H,m)

(Reference example 1)
Synthesis of 5-methyl-3-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride

(Step 1)
Synthesis of tertiary-butyl 4-(N-hydroxyamidine)piperidine-1-carboxylate

Hydroxamine hydrochloride (5.0 g) was dissolved in water (24 ml), sodium carbonate (12.6 g) was added, and then methanol (24 ml) and tert-butyl 4-cyanopiperidine-1-carboxylate (5 .0 g) was added and heated to reflux for 3.5 hours. The solvent was evaporated 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 (5.51 g). Yield 95%.
¹ H-NMR (CD ₃ OD, δppm) 4.11(2H,d), 2.71-2.80(2H,m), 2.19-2.28(1H,m), 1.72(2H,d), 1.53-1.62(2H,m ), 1.45(9H,s)

(Step 2)
Synthesis of tert-butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate

Tertiary-butyl 4-(N-hydroxyamidine)piperidine-1-carboxylate (5.0 g) was dissolved in N,N-dimethylformamide (70 ml), acetic anhydride (2.9 ml) was added, and the mixture was stirred at room temperature. The mixture was stirred at 100° C. for 1 hour and then at 100° C. for 2.5 hours. The resulting liquid was cooled to room temperature, poured into water, 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, and the resulting residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=1/1) to obtain the desired compound (4.08 g). Yield 74%.
^1H -NMR ( _CDCl3 , δppm) 4.10-4.17(2H,m), 2.87-2.97(3H,m), 2.58(3H,s), 1.96(2H,d), 1.70-1.80(2H,m) ,1.47(9H,s)

(Step 3)
Synthesis of 5-methyl-3-(piperidin-4-yl)-1,2,4-oxadiazole hydrochloride

Tertiary-butyl 4-(5-methyl-1,2,4-oxadiazol-3-yl)piperidine-1-carboxylate (4.08 g) was dissolved in 1,4-dioxane (38 ml) and treated with 4M hydrochloric acid. A 1,4-dioxane solution (19 ml) was added and stirred overnight at room temperature. The solvent was distilled off under reduced pressure to obtain the desired compound (2.15 g). Yield 84%.
^1H -NMR ( _CDCl3 , δppm) 3.41-3.46(2H,m), 3.11-3.17(3H,m), 2.58(3H,s), 2.20-2.40(4H,m)

(Reference example 2)
Synthesis of 2-cyano-4',5-bis(trifluoromethyl)-[1',1-biphenyl]-4-carboxylic acid

(Step 1)
Synthesis of methyl 4-amino-2-(trifluoromethyl)benzoate

4-Amino-2-(trifluoromethyl)benzoic acid (25.3 g) was dissolved in methanol (180 ml), and thionyl chloride (17.6 ml) was added under ice-cooling. After that, the mixture was stirred overnight under heating under reflux. The solvent was distilled off under reduced pressure, saturated aqueous sodium bicarbonate was added, 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 desired compound (25.2 g). Yield 93%.
^1H -NMR ( _CD3OD , δppm) 7.75(1H,d), 6.97(1H,d), 6.75(1H,dd), 4.08-4.16(2H,br), 3.86(3H,s)

(Step 2)
Synthesis of methyl 4-amino-5-iodo-2-(trifluoromethyl)benzoate

Methyl 4-amino-2-(trifluoromethyl)benzoate (25.2 g) was dissolved in acetic acid (230 ml), N-iodosuccinimide (25.9 g) was added, and the mixture was stirred at room temperature for 2 hours. Water was added to the obtained liquid, and the precipitate was washed with water. Then, it was dried under reduced pressure to obtain the target compound (37.1 g). Yield 93%.
^1H -NMR ( _CD3OD , δppm) 8.24(1H,s), 7.00(1H,s), 4.65(2H,s), 3.86(3H,s)

(Step 3)
Synthesis of methyl 4-amino-5-cyano-2-(trifluoromethyl)benzoate

Methyl 4-amino-5-iodo-2-(trifluoromethyl)benzoate (37.1 g) was dissolved in NMP (210 ml), copper (I) cyanide (11.6 g) was added thereto, and the mixture was heated to 120°C. and stirred for 3 hours. The resulting liquid was cooled to room temperature, water was added, and the precipitate was washed with water. Then, it was dried under reduced pressure to obtain the target compound (23.5 g). Yield 89%.
¹ H-NMR (CD ₃ OD, δppm) 8.05(1H,s), 7.10(1H,s), 5.02(2H,s), 3.88(3H,s)

(Step 4)
Synthesis of methyl 4-bromo-5-cyano-2-(trifluoromethyl)benzoate

Methyl 4-amino-5-cyano-2-(trifluoromethyl)benzoate (5.0 g) was dissolved in hydrobromic acid (68 ml), to which was added water (14 ml) and sodium nitrite under ice cooling. (4.2 g) was added and stirred for 1 hour. Water (68 ml) and copper(I) bromide (8.8 g) were then added thereto and stirred overnight at room temperature. Ammonia water was added to the obtained liquid, 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, and the precipitated crystals were washed with hexane to obtain the desired compound (4.34 g). Yield 69%.
^1H -NMR ( _CD3OD , δppm) 8.10(1H,s), 8.07(1H,s), 3.96(3H,s)

(Step 5)
Synthesis of methyl 2-cyano-4',5-bis(trifluoromethyl)-[1',1-biphenyl]-4-carboxylate

Methyl 4-bromo-5-cyano-2-(trifluoromethyl)benzoate (2.79 g) and 4-trifluoromethylphenylboronic acid (2.58 g) were added to a mixed solvent of toluene (30 ml) and water (3 ml). Potassium carbonate (3.7 g) and dichlorobis[di-t-butyl(p-dimethylaminophenyl)phosphino]palladium(II) (0.32 g) were added thereto, and the mixture was heated under reflux overnight under a nitrogen atmosphere. . The resulting liquid was cooled to room temperature, water was added, 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, and the obtained residue was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate=10/1) to obtain the target compound (2.58 g). Yield 76%.
^1H -NMR ( _CD3OD , δppm) 8.25(1H,s), 7.90(1H,s), 7.81(2H,d), 7.71(2H,d), 4.00(3H,s)

(Step 6)
Synthesis of 2-cyano-4',5-bis(trifluoromethyl)-[1',1-biphenyl]-4-carboxylic acid

Methyl 2-cyano-4′,5-bis(trifluoromethyl)-[1′,1-biphenyl]-4-carboxylate (2.58 g) was treated with methanol (12 ml), tetrahydrofuran (12 ml) and water (23 ml). To this was added sodium hydroxide (0.41 g) and stirred at room temperature for 4 hours. Diluted hydrochloric acid was added to the obtained liquid, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain the desired compound (2.48 g). Yield 98%.
^1H -NMR ( _CD3OD , δppm) 8.42(1H,s), 7.97(1H,s), 7.83(2H,d), 7.73(2H,d)

Tables 1, 2 and 3 show some of the compounds of the present invention prepared in the same manner as in the above examples. Table 1 shows combinations of Y, R ¹ , R ² , R ³ , R ⁴ , X ² and (X ³ ) _n in formula (I-1) and physical properties of compounds represented by the combinations. Table 2 shows combinations of Y′, R ¹ , R ² , R ³ , R ⁴ and (X ³ ) _n in formula (I-2) and physical properties of compounds represented by the combinations. Table 3 shows combinations of Y, R ¹ , R ² , R ³ , R ⁴ , X ² and Ar in formula (I-3) and physical properties of compounds represented by the combinations. n in formulas (I-1) and (I-2) indicates the number of substituents X ³ on the phenyl group. The column of physical properties indicates the melting point (mp) or properties. In the table, Ph represents a phenyl group, Me represents a methyl group, and Et represents an ethyl group.

Among the compounds shown in the table, ¹ H-NMR (CDCl ₃ ) was measured for compounds with viscous oil or amorphous physical properties. The measured values are shown below.
Compound number (a-8): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.15-1.34 (m, 5H), 1.76-2.05 (m, 3H), 2.46-2.58 (m, 4H), 2.83 (t,1H), 3.07(t,1H), 3.36-3.45(m, 1H), 4.78(t,1H), 6.61(t,1H), 7.25-7.31(m,2H), 7.52-7.61(m ,2H), 7.71(d,1H), 7.82(d,1H).
Compound number (a-10): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.13-1.34 (m, 5H), 1.74-2.05 (m, 3H), 2.41-2.58 (m, 7H), 2.81 (q,1H), 3.07(q,1H), 3.50(d,1H), 4.80(d,1H), 7.38(s,1H), 7.59(d,1H), 7.65-7.67(m,2H), 7.76-7.78(d,2H).
Compound number (c-3): ¹ H-NMR (400 MHz, CDCl ₃ ) δ ppm: 1.14-1.33 (m, 5H), 1.75-2.05 (m, 3H), 2.46-2.57 (m, 4H), 2.84 (t,1H), 3.01-3.08(m,1H), 3.32-3.38(m, 1H), 4.51(t, 2H), 4.78(t,1H), 6.08(tt,1H), 7.43(dd,1H ), 7.72(d,1H), 7.87(d,1H), 8.21(d,1H), 8.54(d,1H).

[Biological test]
The following test examples demonstrate that the compounds of the present invention are useful as active ingredients of insecticides, acaricides or ectoparasite control agents.

(Preparation of test emulsion)
5 parts by mass of the compound of the present invention, 93.6 parts by mass of dimethylformamide, and 1.4 parts by mass of polyoxyethylene alkylaryl ether were mixed and dissolved to prepare emulsion (I) containing 5% active ingredient.

(Test Example 1) Efficacy test for armyworm 0.8 g of a commercially available artificial feed (Insector LFS, manufactured by Nihon Nosan Kogyo Co., Ltd.) and 1 μl of emulsion (I) are well mixed, and each treatment is placed in a plastic test container (1.4 ml volume). 0.2 g per plot was used as a test feed.
Two armyworm 2nd instar larvae were inoculated in each treatment plot and sealed with a plastic lid. It was placed in a temperature-controlled room at 25° C., and the insecticidal rate and food intake were examined on the 5th day. The test was done in duplicate.
The compounds of compound numbers a-6, a-11, a-12, a-13, and a-14 were tested for efficacy against armyworm. All compounds had an insecticidal rate of 90% or a food intake of 10% or less relative to the solvent control group for armyworm.

(Test Example 2) Efficacy test against Aphis gossypii Cucumbers were sown in a 3 cm pot. Female adults of Aphis gossypii were released on cucumbers 10 days after germination. On the next day, the laid 1st instar larvae were retained and the female adults were removed. Emulsion (I) was diluted with water so that the concentration of the compound of the present invention was 125 ppm. This diluted solution was sprayed on the cucumbers. After that, the cucumber was placed in a constant temperature room at a temperature of 25° C. and a humidity of 60%, and after 5 days, the life and death of Aphis gossypii was examined to determine the insecticidal rate.
An efficacy test against Aphis gossypii was performed for the compound of Compound No. a-8. This compound had an insecticidal rate of 90% or more.

(Test Example 3) Efficacy test against spider mite kanzawa Five adult female kanzawa spider mites from Okayama Prefecture were inoculated onto primary mung bean leaves. Then, the emulsion (I) was diluted with water so that the concentration of the compound was 125 mass ppm to obtain a drug. The agent was sprayed on the mung beans and allowed to air dry. After that, it was placed in a constant temperature room with a temperature of 25° C. and a humidity of 65%. Ten days after spraying, the life and death of mites were investigated. The test was done in duplicate.
The compounds with the compound numbers shown in Table 4 were tested for efficacy against spider mite Kanzawa. All of the compounds exhibited an insecticidal rate of 90% or more against spider mite Kanzawa.

(Test Example 4) Efficacy test against two-spotted spider mite Seedlings of kidney bean were raised in a 3-inch pot, and eight adult female two-spotted 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 mass ppm. The diluted solution was sprinkled on the green beans. The green beans were placed in a constant temperature room with a temperature of 25° C. and a humidity of 65%. Ten days after spraying, the life and death of mites were investigated. The test was done in duplicate.
An efficacy test against two-spotted spider mites was conducted for the compounds having the compound numbers shown in Table 5. All compounds showed an insecticidal rate of 90% or more.

Since the compounds selected at random from the compounds of the present invention exhibit the above effects, the compounds of the present invention, including compounds that could not be exemplified, can be used for pest control, especially insecticides, acaricides, ectoparasites. It can be understood that it is a compound that has effects such as insect control, does not cause phytotoxicity to plants, has little toxicity to humans, livestock and fish, and has little impact on the environment.

Claims (4)

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

[In formula (I),
Ar represents a substituted or unsubstituted C6-10 aryl group or a substituted or unsubstituted 5- to 6-membered heteroaryl 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 halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group;
R ⁴ represents a hydrogen atom, a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkoxy group, or a cyano group;
Q represents a group represented by formula (Qa) or formula (Qb).

In the above formulas (Qa) and (Qb),
Arrows indicate binding positions,
p ¹ indicates the number of methylenes in the parentheses and is 0 or 1;
p ² indicates the number of methylenes in the parentheses and is an integer from 0 to 2,
X ¹ represents a substituent on the ring and is a halogeno group, a substituted or unsubstituted C1-6 alkyl group, a hydroxyl group, a substituted or unsubstituted C1-6 alkylsulfonyloxy group, or a substituted or unsubstituted C1-6 an alkylthio group,
m represents the number of X ¹ and is any chemically acceptable integer from 0 to 4,
X 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,
Y represents a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl group;
Y' is a substituted or unsubstituted C1-6 alkyl group, a substituted or unsubstituted C1-6 alkylsulfonyl group, a substituted or unsubstituted C6-10 aryl group, or a substituted or unsubstituted 5- to 6-membered heteroaryl indicates a group. ] A pest control agent containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof. An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the compound according to claim 1 and salts thereof. An ectoparasite control or extermination agent containing, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and salts thereof.