JPWO2015068719A1 - Pyridine compounds and pest control agents - Google Patents

Abstract

The pest control agent having excellent insecticidal activity and / or acaricidal activity comprises, as an active ingredient, at least one selected from the group consisting of the compound represented by formula (I) or a salt thereof, and the compound and the salt thereof contains. In the formula, R1 represents a C1-6 haloalkyl group, X1 represents a halogeno group, etc., m is an integer of 0 to 3, and X2 is an unsubstituted or substituted C1 To 6 alkoxy groups, n is an integer of 0 to 4, R2 represents a hydrogen atom, Z represents an oxygen atom, and B1, B2, and B3 each independently represent carbon An atom or a nitrogen atom is shown, and one or two of them represent a nitrogen atom.

Description

The present invention relates to a pyridine compound and a pest control agent. More specifically, the present invention relates to a pyridine compound that has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized advantageously industrially, and a pest control agent containing this as an active ingredient About.
This application claims priority based on Japanese Patent Application No. 2013-231603 filed in Japan on November 7, 2013 and Japanese Patent Application No. 2014-013786 filed in Japan on January 28, 2014. Is hereby incorporated by reference.

Various compounds having insecticidal / miticidal activity have been proposed. For example, Patent Document 1 describes a 2,6-dichloro-4-pyridinemethanol compound. This compound appears to have an excellent effect in controlling various plant diseases caused by phytopathogenic viruses, bacteria and filamentous fungi. Patent Document 2 describes a pyridylpyridine compound. This compound has an effect as an agricultural and horticultural fungicide.
In order to put such compounds into practical use as agricultural chemicals, they are not only sufficiently effective but also resistant to drug resistance, do not cause phytotoxicity or soil contamination on plants, and have low toxicity to livestock and fish. Etc. are required.

Japanese Patent Laid-Open No. 11-171864 JP 2001-55304 A

  An object of the present invention is to provide a pyridine compound that is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously, and includes this as an active ingredient It is providing the pest control agent contained as. Furthermore, it is providing the ectoparasite control agent which contains this as an active ingredient.

As a result of intensive studies to solve the above problems, the present inventors have found that a pyridine compound having a specific structure has excellent insecticidal activity and / or acaricidal activity, and exhibits good characteristics and high safety. It was found that it can be used as an active ingredient of a pest control agent. Furthermore, it discovered that it could utilize as an active ingredient of an ectoparasite control agent. The present invention has been completed based on this finding.
That is, the present invention includes the following.
[1] A compound represented by the formula (I) or a salt thereof.

In the formula (I), R ¹ is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 haloalkoxy group, a C 1-6 alkoxy C 1-6 haloalkyl group, a halogeno group, a cyano C 1-6 alkyl group, dioxolanyl. Group or formyl group.
X ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, amino group, unsubstituted Or a substituted C1-6 alkylamino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group having a group, unsubstituted or substituted C3-8 cycloalkyl group Unsubstituted or C6~10 aryl group having a substituent, 3- to 6-membered heterocyclyl group having unsubstituted or substituted group, halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer from 0 to 3. When m is 2 or more, X ¹ may be the same as or different from each other.
X ² is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, formyl group, unsubstituted or substituted A C1-6 alkylcarbonyl group having a group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an aminocarbonyl group, Unsubstituted or substituted C1-6 alkylaminocarbonyl group, mercapto group, unsubstituted Is a substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, formyloxy group, unsubstituted or substituted A C1-6 alkylcarbonyloxy group having a group, an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, an aminocarbonyloxy group, an unsubstituted or substituted C1-6 alkylaminocarbonyloxy group, Substituted or substituted C1-6 alkylsulfonyloxy groups, unsubstituted or substituted C3-8 cycloalkyl groups, unsubstituted or substituted C4-8 cycloalkenyl groups, unsubstituted or substituted C6-10 aryl group having a group, unsubstituted or substituted A C6-10 aryloxy group having an alkyl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, an unsubstituted or substituted C6-10 arylthio group, an unsubstituted or substituted C6-10 aryl A sulfinyl group, a halogeno group, a cyano group, or a nitro group is shown.
n shows the number of X < ² > and is an integer in any one of 0-3. When n is 2 or more, X ² may be the same as or different from each other.
R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl group, A substituted or substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or A C1-6 alkylsulfonyl group having a substituent, an unsubstituted or substituted C6-10 arylcarbonyl group, or an unsubstituted or substituted 3-6 membered heterocyclylcarbonyl group is shown.
Z represents an oxygen atom or a sulfur atom.
B ¹ , B ² , and B ³ each independently represent a carbon atom or a nitrogen atom, and any one or two of them represent a nitrogen atom.
[2] A pest control agent comprising at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.
[3] An insecticide or acaricide containing at least one selected from the group consisting of the compound according to [1] and a salt thereof as an active ingredient.
[4] An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to [1] and a salt thereof.

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

[Compound (I)]
The pyridine compound of the present invention is a compound represented by formula (I) (hereinafter sometimes referred to as compound (I)) or a salt thereof.

First, in the present invention, the term “unsubstituted” means only a group serving as a mother nucleus. When there is no description of “having a substituent” and only the name of the group serving as a mother nucleus is used, it means “unsubstituted” unless otherwise specified.
On the other hand, the term “having a substituent” means that any hydrogen atom of a group serving as a mother nucleus is substituted with a group having the same or different structure from the mother nucleus. Accordingly, the “substituent” is another group bonded to a group serving as a mother nucleus. The number of substituents may be one, or two or more. Two or more substituents may be the same or different.
Terms such as “C1-6” indicate that the number of carbon atoms of the group serving as the mother nucleus is 1-6. This number of carbon atoms does not include the number of carbon atoms present in the substituent. For example, a butyl group having an ethoxy group as a substituent is classified as a C2 alkoxy C4 alkyl group.

The “substituent” is not particularly limited as long as it is chemically acceptable and has the effects of the present invention. Examples of groups that can be “substituents” are shown below.
C1-6 such as methyl group, ethyl group, n-propyl group, i-propyl group, n-butyl group, s-butyl group, i-butyl group, t-butyl group, n-pentyl group and n-hexyl group An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;

A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group;
C4-8 cycloalkenyl groups such as 2-cyclopentenyl group, 3-cyclohexenyl group, 4-cyclooctenyl group;
A C6-10 aryl group such as a phenyl group or a naphthyl group;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
A 3-6 membered heterocyclyl group;
A 3-6 membered heterocyclyl C1-6 alkyl group;

Hydroxyl group;
C1-6 alkoxy groups such as methoxy group, ethoxy group, n-propoxy group, i-propoxy group, n-butoxy group, s-butoxy group, i-butoxy group, t-butoxy group;
C2-6 alkenyloxy groups such as vinyloxy group, allyloxy group, propenyloxy group, butenyloxy group;
A C2-6 alkynyloxy group such as an ethynyloxy group or a propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
A C6-10 aryl C1-6 alkoxy group such as a benzyloxy group or a phenethyloxy group;
A 3-6 membered heterocyclyloxy group;
A 3-6 membered heterocyclyl C1-6 alkoxy group;

Formyl group;
A C1-6 alkylcarbonyl group such as an acetyl group or a propionyl group;
A C6-10 arylcarbonyl group such as a benzoyl group;
A 3-6 membered heterocyclylcarbonyl group;
Carboxyl group;
A C1-6 alkoxycarbonyl group such as a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, an n-butoxycarbonyl group, a t-butoxycarbonyl group;
Formyloxy group;
A C1-6 alkylcarbonyloxy group such as an acetyloxy group or a propionyloxy group;
C1-6 alkoxycarbonyloxy groups such as methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group;

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

An amino group;
A C1-6 alkylamino group such as a methylamino group, a dimethylamino group, a diethylamino group;
A C6-10 arylamino group such as an anilino group or a naphthylamino group;
A C6-10 aryl C1-6 alkylamino group such as a benzylamino group or a phenethylamino group;
Formylamino group;
A C1-6 alkylcarbonylamino group such as an acetylamino group, a propanoylamino group, a butyrylamino group, an i-propylcarbonylamino group;
A C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, an ethoxycarbonylamino group, an n-propoxycarbonylamino group, an i-propoxycarbonylamino group;
An aminocarbonyl group;
A C1-6 alkylaminocarbonyl group such as a dimethylaminocarbonyl group;
Imino C1-6 alkyl groups such as an iminomethyl group, a (1-imino) ethyl group, a (1-imino) -n-propyl group;
N-hydroxy-iminomethyl group, (1- (N-hydroxy) -imino) ethyl group, (1- (N-hydroxy) -imino) propyl group, N-methoxy-iminomethyl group, (1- (N-methoxy) -Imino) N-hydroxyimino C1-6 alkyl group having an unsubstituted or substituted group such as an ethyl group;
An aminocarbonyloxy group;
A C1-6 alkylaminocarbonyloxy group such as an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group;

A mercapto group;
A C1-6 alkylthio group such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, or a t-butylsulfinyl group;
A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
A 3-6 membered heterocyclylthio group;
A C6-10 arylsulfinyl group such as a phenylsulfinyl group;
A 3-6 membered heterocyclylsulfinyl group;
A C6-10 arylsulfonyl group such as a phenylsulfonyl group;
A 3-6 membered heterocyclylsulfonyl group;
A C1-6 haloalkylthio group such as a trifluoromethylthio group or a 2,2,2-trifluoroethylthio group;
Alkylsulfonyloxy groups such as methylsulfonyloxy group, ethylsulfonyloxy group, t-butylsulfonyloxy group;
A C1-6 haloalkylsulfinyl group such as a trifluoromethylsulfinyl group or a 2,2,2-trifluoroethylsulfinyl group;
A C1-6 haloalkylsulfonyl group such as a trifluoromethylsulfonyl group or a 2,2,2-trifluoroethylsulfonyl group;
A haloalkylsulfonyloxy group such as a trifluoromethylsulfonyloxy group or a 2,2,2-trifluoroethylsulfonyloxy group;

A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, or a t-butyldimethylsilyl group;
A tri-C6-10 aryl-substituted silyl group such as a triphenylsilyl group;
Cyano group; nitro group.
In these “substituents”, any hydrogen atom in the substituent may be substituted with a group having a different structure. In this case, examples of the “substituent” include a C1-6 alkyl group, a C1-6 haloalkyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

  In addition, the above “3 to 6-membered heterocyclyl group” includes at least one (for example, 1 to 4) heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring constituent atoms. It is a waste. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, if at least one ring is a hetero ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3-6 membered heterocyclyl group” include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

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

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

[R ¹ ]
In the formula (I), R ¹ is a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 haloalkoxy group, a C 1-6 alkoxy C 1-6 haloalkyl group, a halogeno group, a cyano C 1-6 alkyl group, dioxolanyl. Group or formyl group.
The “C1-6 alkyl group” in R ¹ may be a straight chain or a branched chain as long as it has 3 or more carbon atoms. As the “C1-6 alkyl group”, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group , T-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

As the “C 1-6 haloalkyl group” in R ¹ , a fluoromethyl group, a chloromethyl group, a bromomethyl group, a difluoromethyl group, a dichloromethyl group, a dibromomethyl group, a trifluoromethyl group, a trichloromethyl group, a tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2, 2,2-trifluoro-1-trifluoromethylethyl group, 1,2,2,2-tetrafluoro-1-trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, perfluorooctyl group, perfluorooctyl group A chlorooctyl group, a 2,4,6-trichlorohexyl group, etc. are mentioned.

As the “C 1-6 haloalkoxy group” in R ¹ , a chloromethoxy group, a dichloromethoxy group, a difluoromethoxy group, a trichloromethoxy group, a trifluoromethoxy group, a 1-fluoroethoxy group, a 1,1-difluoroethoxy group, 2 2,2-trifluoroethoxy group, pentafluoroethoxy group, 2,2,3,4,4,4-hexafluoro-butoxy group and the like.

Examples of the “C1-6 alkoxy C1-6 haloalkyl group” for R ¹ include a methoxydifluoromethyl group, a 2,2,2-trifluoro-1-methoxy-1-trifluoromethylethyl group, and the like.
Examples of the “halogeno group” for R ¹ include a fluoro group, a chloro group, a bromo group, and an iodo group.
Examples of the “cyano C 1-6 alkyl group” for R ¹ include a cyanomethyl group and a 2-cyanopropan-2-yl group.
Here, R ¹ is preferably any one selected from a C 1-6 haloalkyl group, a C 1-6 alkoxy C 1-6 haloalkyl group, a cyano C 1-6 alkyl group, and a dioxolanyl group, A 6-haloalkyl group is more preferred.

[X ^1, m]
In the formula (I), X ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl. Group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group An amino group, an unsubstituted or substituted C1-6 alkylamino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group An unsubstituted or substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C3-8 cyclo Alkyl group, an unsubstituted or C6~10 aryl group having a substituent, 3- to 6-membered heterocyclyl group having unsubstituted or substituted group, halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer from 0 to 3. When m is 2 or more, X ¹ may be the same as or different from each other. Among these, m is preferably 0 or 1.
X ¹ is preferably substituted at the position labeled “3” in formula (I).

The “C 1-6 alkyl group” in X ¹ may be a straight chain or a branched chain as long as it has 3 or more carbon atoms. As the “C1-6 alkyl group”, methyl group, ethyl group, n-propyl group, n-butyl group, n-pentyl group, n-hexyl group, i-propyl group, i-butyl group, s-butyl group , T-butyl group, i-pentyl group, neopentyl group, 2-methylbutyl group, 2,2-dimethylpropyl group, i-hexyl group and the like.

Specific examples of the “C1-6 alkyl group having a substituent” include
C3-8 cycloalkyl C1-6 alkyl group such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group; fluoromethyl group, chloromethyl group, bromomethyl Group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 1-chloroethyl group, 2,2,2-trifluoroethyl group, 2,2,2- Trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, perfluoro Hexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl A C1-6 haloalkyl group such as a group;

  Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group; methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxy group And C1-6 alkoxy C1-6 alkyl groups such as a methyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group;

As the “C2-6 alkenyl group” for X ¹ , a vinyl group, 1-propenyl group, 2-propenyl group, 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, 1-pentenyl group, 2-pentenyl group, 3-pentenyl group, 4-pentenyl group, 1-methyl-2-butenyl group, 2-methyl-2-butenyl group, 1-hexenyl Group, 2-hexenyl group, 3-hexenyl group, 4-hexenyl group, 5-hexenyl group and the like.
Specific examples of the “substituted C2-6 alkenyl group” include C2-6 haloalkenyl groups such as 2-chloro-1-propenyl group and 2-fluoro-1-butenyl group;

As the “C 2-6 alkynyl group” in X ¹ , an ethynyl group, a 1-propynyl group, a 2-propynyl group, a 1-butynyl group, a 2-butynyl group, a 3-butynyl group, a 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.
“C2-6 alkynyl group having a substituent” is a C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group, etc. And so on.

As the “C1-6 alkoxy group” in X ¹ , a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, an i-propoxy group, an i-butoxy group , S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Specific examples of the “C1-6 alkoxy group having a substituent” include a chloromethoxy group, a dichloromethoxy group, a difluoromethoxy group, a trichloromethoxy group, a trifluoromethoxy group, a 1-fluoroethoxy group, and a 1,1-difluoroethoxy group. Group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group, C1-6 haloalkoxy group such as 2,2,3,4,4,4-hexafluoro-butoxy group; methoxymethoxy group, methoxyethoxy C1-6 alkoxy groups such as C1-6 alkoxy groups; C3-8 cycloalkyl C1-6 alkoxy groups such as cyclopropylmethyloxy groups; cyano C1-6 alkoxy groups such as cyanomethoxy groups and 2-cyanoethoxy groups; benzyl Unsubstituted or substituted, such as oxy group and phenethyloxy group C6-10 aryl C1-6 alkoxy groups; unsubstituted or substituted 5-6 membered heterocyclyl C1-6 alkoxy groups such as a tetrahydrofuranylmethoxy group, an unsubstituted or substituted pyridylmethoxy group; Can be mentioned.

  Examples of the substituent on the 5- to 6-membered heterocyclic ring in the “C 6-10 aryl C 1-6 alkoxy group” and the “5-6-membered heterocyclyl C 1-6 alkoxy group” include a C 1-6 alkyl group, a C 1-6 haloalkyl group, Examples thereof include a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, and a nitro group.

Examples of the “C1-6 alkylcarbonyl group” for X ¹ include an acetyl group and a propionyl group.
Specific examples of the “substituted C1-6 alkylcarbonyl group” include C1-6 haloalkylacyl groups such as a chloroacetyl group, a trifluoroacetyl group, and a trichloroacetyl group.

Examples of the “C1-6 alkoxycarbonyl group” for X ¹ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
As a specific example of “C1-6 alkoxycarbonyl group having a substituent”,
C3-8 cycloalkyl C1-6 alkoxycarbonyl groups such as cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-cyclopropylethoxycarbonyl group; fluoromethoxycarbonyl group, chloromethoxy Carbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2,2-trifluoroethoxycarbonyl A C1-6 haloalkoxycarbonyl group such as a group; and the like.

Examples of the “C1-6 alkylamino group” for X ¹ include a methylamino group, an n-butylamino group, a dimethylamino group, a diethylamino group, and the like.

Examples of the “C 1-6 alkylthio group” in X ¹ include methylthio group, ethylthio group, n-propylthio group, n-butylthio group, n-pentylthio group, n-hexylthio group, i-propylthio group, i-butylthio group and the like. It is done.
Specific examples of the “C1-6 alkylthio group having a substituent” include C1-6 haloalkylthio groups such as a trifluoromethylthio group and a 2,2,2-trifluoroethylthio group.

Examples of the “C1-6 alkylsulfinyl group” for X ¹ include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.
Specific examples of the “substituted C1-6 alkylsulfinyl group” include C1-6 haloalkylsulfinyl groups such as a trifluoromethylsulfinyl group and a 2,2,2-trifluoroethylsulfinyl group.

Examples of the “C1-6 alkylsulfonyl group” for X ¹ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.
Specific examples of the “substituted C1-6 alkylsulfonyl group” include C1-6 haloalkylsulfonyl groups such as a trifluoromethylsulfonyl group and a 2,2,2-trifluoroethylsulfonyl group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for X ¹ Substituents on "group", "C1-6 alkylamino group", "C1-6 alkylthio group", "C1-6 alkylsulfinyl group", and "C1-6 alkylsulfonyl group" include C1-6 alkoxy groups A halogeno group, a cyano group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 3-6 membered heterocyclyl group, and the like.

Examples of the “C 3-8 cycloalkyl group” for X ¹ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and the like.

The “C6-10 aryl group” in X ¹ may be monocyclic or polycyclic. In the polycyclic aryl group, if at least one ring is an aromatic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring.
Examples of the “C6-10 aryl group” include phenyl group, naphthyl group, azulenyl group, indenyl group, indanyl group, tetralinyl group and the like.

The “3- to 6-membered heterocyclyl group” in X ¹ includes at least one (for example, 1 to 4) heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as ring constituent atoms. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, if at least one ring is a hetero ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3-6 membered heterocyclyl group” include a 3-6 membered saturated heterocyclyl group, a 5-6 membered heteroaryl group, a 5-6 membered partially unsaturated heterocyclyl group, and the like.

  Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group (specifically, [1,3] dioxolanyl group), Examples include dioxanyl groups (specifically, [1,3] dioxanyl groups or [1,4] dioxanyl groups). Preferably, it is a 5-6 membered saturated heterocyclyl group.

Examples of the 5-membered heteroaryl group include pyrrolyl, furyl, thienyl, imidazolyl, pyrazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, triazolyl (for details, [1,2,3] triazolyl Or [1,2,4] triazolyl group), oxadiazolyl group (specifically, [1,2,4] oxadiazolyl group or [1,3,4] oxadiazolyl group), thiadiazolyl group, tetrazolyl group and the like. .
Examples of the 6-membered heteroaryl group include a pyridyl group, a pyrazinyl group, a pyrimidinyl group, a pyridazinyl group, and a triazinyl group.

Examples of the partially unsaturated 5-membered heterocyclyl group include pyrrolinyl group, imidazolinyl group (dihydroimidazolyl group), pyrazolinyl group, oxazolinyl group, isoxazolinyl group, thiazolinyl group and the like.
Examples of the partially unsaturated 6-membered heterocyclyl group include a thiopyranyl group, a 2H-pyridin-1-yl group, and a 4H-pyridin-1-yl group.

Examples of the substituent on “C3-8 cycloalkyl group”, “C6-10 aryl group”, and “3-6 membered heterocyclyl group” in X ¹ include a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, A C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, a cyano group, a nitro group, etc. are mentioned.

Examples of the “halogeno group” for X ¹ include a fluoro group, a chloro group, a bromo group, and an iodo group.

Here, the ^{X 1,} preferably C1~6 alkyl group or a halogeno group, a halogeno group is more preferable.

[X ^2, n]
X ² is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, formyl group, unsubstituted or substituted A C1-6 alkylcarbonyl group having a group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an aminocarbonyl group, Unsubstituted or substituted C1-6 alkylaminocarbonyl group, mercapto group, unsubstituted Is a substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, formyloxy group, unsubstituted or substituted A C1-6 alkylcarbonyloxy group having a group, an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, an aminocarbonyloxy group, an unsubstituted or substituted C1-6 alkylaminocarbonyloxy group, Substituted or substituted C1-6 alkylsulfonyloxy groups, unsubstituted or substituted C3-8 cycloalkyl groups, unsubstituted or substituted C4-8 cycloalkenyl groups, unsubstituted or substituted C6-10 aryl group having a group, unsubstituted or substituted A C6-10 aryloxy group having an alkyl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, an unsubstituted or substituted C6-10 arylthio group, an unsubstituted or substituted C6-10 aryl A sulfinyl group, a halogeno group, a cyano group, or a nitro group is shown.
n shows the number of X < ² > and is an integer in any one of 0-3. When n is 2 or more, X ² may be the same as or different from each other. Among these, n is preferably 1.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for X ² Group "," C1-6 alkylamino group "," C1-6 alkylthio group "," C1-6 alkylsulfinyl group "," C1-6 alkylsulfonyl group "," C3-8 cycloalkyl group "," C6- Examples of the “10 aryl group”, “3 to 6-membered heterocyclyl group”, and “halogeno group” and the group having a substituent in these groups are the same as those exemplified in X ¹ above.

Examples of the “C2-6 alkenyloxy group” for X ² include a vinyloxy group and an allyloxy group.

Examples of the “C2-6 alkynyloxy group” for X ² include an ethynyloxy group, a 1-propynyloxy group, a 2-propynyloxy group, and the like.

Examples of the “C 1-6 alkylaminocarbonyl group” for X ² include a methylaminocarbonyl group, a dimethylaminocarbonyl group, a diethylaminocarbonyl group, an i-propylaminocarbonyl group, and a methyl- (i-propyl) aminocarbonyl group. .

Examples of the “C1-6 alkylcarbonyloxy group” for X ² include an acetyloxy group and a propionyloxy group.

Examples of the “C1-6 alkoxycarbonyloxy group” in X ² include a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, and a t-butoxycarbonyl group. An oxy group etc. are mentioned.

Examples of the “C1-6 alkylaminocarbonyloxy group” for X ² include an ethylaminocarbonyloxy group and a dimethylaminocarbonyloxy group.

Examples of the “C1-6 alkylsulfonyloxy group” for X ² include a methylsulfonyloxy group, an ethylsulfonyloxy group, a t-butylsulfonyloxy group, and the like.
Specific examples of the “substituted C1-6 alkylsulfonyloxy group” include C1-6 haloalkylsulfonyloxy groups such as a trifluoromethylsulfonyloxy group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for X ² Group "," C1-6 alkylamino group "," C1-6 alkylthio group "," C1-6 alkylsulfinyl group "," C1-6 alkylsulfonyl group "," C2-6 alkenyloxy group "," C2- 6 alkynyloxy group "," C1-6 alkylaminocarbonyl group "," C1-6 alkylcarbonyloxy group "," C1-6 alkoxycarbonyloxy group "," C1-6 alkylaminocarbonyloxy group ", and" C1 Examples of the substituent on "-6 alkylsulfonyloxy group" include C1-6 alkoxy group, halogeno group, cyano group, C3-8 cyclo Alkyl group, C6-10 aryl group, and the like 3-6 membered heterocyclyl group.

Examples of the “C4-8 cycloalkenyl group” for X ² include a cyclobutel group, a cyclopentel group, a cyclohexel group, and the like.

Examples of the “C6-10 aryloxy group” in X ² include a phenyloxy group and a naphthoxy group.

Examples of the “C6-10 arylthio group” in X ² include a phenylthio group and a naphthylthio group.

Examples of the “C6-10 arylsulfinyl group” for X ² include a phenylsulfinyl group.

"C3~8 cycloalkyl group" in X ^2, "C6~10 aryl group", "3-6 membered heterocyclyl group", "C4~8 cycloalkenyl group", "C6~10 aryloxy group", "C6~ The substituents on “10 arylthio group” and “C6-10 arylsulfinyl group” include C1-6 alkyl group, C1-6 haloalkyl group, hydroxyl group, C1-6 alkoxy group, C1-6 haloalkoxy group, halogeno group. , A cyano group, a nitro group, and the like.

Here, the X ^2, unsubstituted or Cl to 6 alkyl group having a substituent, unsubstituted or Cl to 6 alkoxy group having a substituent, Cl to 6 alkylthio group having unsubstituted or substituted group, Unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted 3-6 membered heterocyclyl group, halogeno group, C6- A 10 aryl group or a cyano group is preferred. Among these, as ^{X 2,} Cl to 6 alkoxy, Cl to 6 haloalkoxy group, Cl to 6 alkoxy Cl to 6 alkoxy, Cl to 6 alkylthio, Cl to 6 haloalkylthio group, Cl to 6 alkylsulfinyl group , A C1-6 alkylsulfonyl group, a 5-membered heteroaryl group (more preferably a pyrazolyl group), a phenyl group, or a halogeno group is more preferable.

[R ² ]
R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl group, A substituted or substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or A C1-6 alkylsulfonyl group having a substituent, an unsubstituted or substituted C6-10 arylcarbonyl group, or an unsubstituted or substituted 3-6 membered heterocyclylcarbonyl group is shown.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C1-6 alkoxy group”, “C1-6 alkylcarbonyl group”, “C1-6 alkoxycarbonyl” for R ² Examples of the “group”, “C1-6 alkylsulfonyl group”, and groups having a substituent in these groups include the same as those exemplified in the above X ¹ .

Examples of the “C6-10 arylcarbonyl group” in R ² include a benzoyl group and a naphthylcarbonyl group.
Examples of the “3 to 6 membered heterocyclylcarbonyl group” for R ² include a 5 to 6 membered heteroarylcarbonyl group.
As a 5-6 membered heteroarylcarbonyl group,
Pyrrolylcarbonyl group, furylcarbonyl group, thienylcarbonyl group, imidazolylcarbonyl group, pyrazolylcarbonyl group, oxazolylcarbonyl group, isoxazolylcarbonyl group, thiazolylcarbonyl group, isothiazolylcarbonyl group, triazolylcarbonyl Group, oxadiazolylcarbonyl group, thiadiazolylcarbonyl group, tetrazolylcarbonyl group;
Pyridylcarbonyl group, pyrazinylcarbonyl group, pyrimidinylcarbonyl group, pyridazinylcarbonyl group, triazinylcarbonyl group; and the like.
Examples of the substituent on the “C6-10 arylcarbonyl group” in R ² include a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a halogeno group, and a cyano group. And nitro group.
Examples of the substituent on the “3- to 6-membered heterocyclylcarbonyl group” in R ² include a C 1-6 alkyl group, a C 1-6 haloalkyl group, a hydroxyl group, a C 1-6 alkoxy group, a C 1-6 haloalkoxy group, a halogeno group, and a cyano group. Group, nitro group, 5-6 membered heteroaryl group and the like. The “5- to 6-membered heteroaryl group” is an aromatic containing at least one (for example, 1 to 4) heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom, and a sulfur atom as a ring-constituting atom. A ring, preferably a 5-membered heteroaryl group, more preferably a pyrazolyl group.
Here, as R ² , a hydrogen atom, a C 1-6 alkyl group, a C 1-6 alkoxy group, or a 6-membered heteroarylcarbonyl group optionally substituted with a 5-6-membered heteroaryl group (more preferably 5 A pyridylcarbonyl group substituted with a membered heteroaryl group) is preferred, and a hydrogen atom is more preferred.

[Z]
Z represents an oxygen atom or a sulfur atom.
Here, as Z, an oxygen atom is preferable.

[B ^1, B ^2, B ^3]
B ¹ , B ² , and B ³ each independently represent a carbon atom or a nitrogen atom, and any one or two of them represent a nitrogen atom.
That is, the compound represented by the formula (I) represents any one of the compounds represented by the following formulas (II) to (V).
Here, the compound represented by the formula (I) is preferably a compound represented by the formula (II), the formula (III), or the formula (IV), and is represented by the formula (II) or the formula (IV). The compound represented by formula (II) is more preferred.

  The salt of the compound (I) of the present invention is not particularly limited as long as it is an agro-horticulturally acceptable salt. Examples of the salt of compound (I) include salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; alkaline earth such as calcium and magnesium A salt of a transition metal such as iron or copper; a salt of an organic base such as ammonia, triethylamine, tributylamine, pyridine or hydrazine.

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

The compound of the present invention is excellent in controlling pests such as various agricultural pests and mites that affect plant growth.
In addition, the compound of the present invention is a highly safe compound because it has little phytotoxicity and low toxicity to fish and warm-blooded animals. Therefore, it is useful as an active ingredient of an insecticide or an acaricide.
Furthermore, in recent years, resistance to organophosphates and carbamates has been developed in many pests such as diamondback moth, leafhopper, leafhopper, and aphid, resulting in insufficient efficacy of these drugs. Is desired. The compound of the present invention exhibits an excellent control effect not only on susceptible strains but also on pests of various resistant strains and further on mite-resistant strains of mites.

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

[Pesticides, insecticides or acaricides]
The pest control agent or insecticide or acaricide of the present invention contains at least one selected from the compounds of the present invention as an active ingredient.
Examples of plants to be treated with the pest control agent of the present invention include cereals, vegetables, root vegetables, potatoes, trees, grasses, turf and the like. In that case, each part of these plants can also be processed. Examples of each part of the plant include leaves, stems, patterns, flowers, buds, fruits, seeds, sprout, roots, tubers, tuberous roots, shoots, cuttings, and the like. Further, improved varieties and varieties of these plants, cultivated varieties, and mutants, hybrids, and genetically modified organisms (GMO) can also be treated.

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

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

(1) Lepidoptera butterflies or moths (a) Arctiidae moths, such as Hyphantria cunea, Lemyra imparilis;
(B) moths of the family Bucculatricidae, for example, Bucculatrix pyrivorella;
(C) Carposinidae, for example, Carposina sasakii;
(D) moths of the family Craambidae, for example, Diaphania indica, Diaphania nitidalis of Diaphania spp .; for example, Ostrinia spp. Astragalus (Ostrinia furnacalis), European corn borer (Ostrinia nubilalis), Azuki bean (Ostrinia scapulalis); Others Diatraea grandiosella), Glyphodes pyloalis, Hellula undalis, Parapediasia teterrella;
(E) Gelechiidae moths, for example, Helcystogramma triannulella, Pectinophora gossypiella, Phthhorimaea operculella, Sitotroga cerealella;
(F) Geometridae moths, for example Ascotis selenaria;
(G) moths of the family Gracillariidae, for example, Caloptilia theivora, citrus moth (Phyllocnistis citrella), king moth (Phyllonorycter ringoniella);
(H) Hesperiidae butterflies, such as Parrotara guttata;
(I) moths of the Lasiocampidae family, for example, Obicalale (Malacosoma neustria);
(J) Lymantriidae moths, for example, Lymantria spp., Lymantria dispar, Nonmanai (Lymantria monacha); Others, Euproctis pseudoconspersa, Orgyia thyellina);

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

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

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

(3) Hemiptera pests (A) Ceratomas (Archaeorrhyncha)
(A) From the Delphacidae family, for example, the brown planthopper (Laodelphax striatella), the brown planthopper (Nilaparvata lugens), the black planthopper (Perkinsiella saccharicida), the white planthopper (Sogatella furcifera);

(B) Clypeorrhyncha
(A) From the family of Cicadellidae, for example, from Empoasca spp., Empoasca fabae, Empoasca nipponica, Empoasca onukii, legume Empoasca sakaii, Others );

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

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

(D) Sternorrhyncha
(A) from the family Adelgidae, for example, Adelges laricis;
(B) From the Aleyrodidae family, for example, Bemisia spp., Silver leaf whitefly (Bemisia argentifolii), Tobacco whitefly (Bemisia tabaci); Other, Aleurocanthus spiniferus (Dialeurodes citri), Trialeurodes vaporariorum;
(C) From the aphid family (Aphididae), for example, Aphis fabae, Aphis forbesi, Cotton aphid (Aphis gossypii), European apple aphid (Aphis) of the genus Aphis spp. pomi), Aphis sambuci, Aphis spiraecola; eg, Rhopalosiphum spp., Rhopalosiphum maidis, Rhopalosiphum padi, eg Rhopalosiphum padi; Dysaphis spp., Dysaphis plantaginea, Dysaphis radicola; eg, Macrosiphum spp., Macrosiphum avenae, phorus eu , Myzus spp., Myrtle aphid (My zus cerasi, peach aphid (Myzus persicae), myrtle aphid (Myzus varians); other, pea aphid (Acyrthosiphon pisum), potato beetle aphid (Aulacorthum solani), barley aphid hel chyra Brevicors Metopolophium dirhodum), lettuce aphids (Nasonovia ribis-nigri), hops aphids (Phorodon humuli), barley aphids (Schizaphis graminum), barley aphids (Sitobion avenae), rice aphids (Toxoptera aurantii;

(D) From the family of Coccidae, for example, Ceroplastes ceriferus, Ceroplastes rubens of the genus Ceroplastes spp .;
(E) from the genus Diaspididae, for example, from Pseudaulacaspis spp., Pseudaulacaspis pentagona, Pseudaulacaspis prunicola; for example, Unaspis spp species .), Paramecium scales (Unaspis euonymi), Panax scales (Unaspis yanonensis); Pseudaonidia paeoniae);
(F) from the order of the Margarodidae, for example, Drosicha corpulenta, Icerya purchasi;
(G) from the family Phylloxeridae, for example, grape aphids (Viteus vitifolii);
(H) From the Pseudococcidae family, for example, Planococcus citri, Planococcus kuraunhiae; other species, Phenacoccus solani (Phenacoccus solun) , Pseudococcus comstocki;
(I) from the family Psyllidae, for example, Psylla mali, Psylla mali, Psylla pyrisuga; other, Diaphorina citri;

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

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

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

(B) Nematocera
(A) From the family of Cecidomyiidae, for example, the soybean flies (Asphondylia yushimai), the sorghum flies (Contarinia sorghicola), the flies (Mayetiola destructor), the mudworms (Sitodiplosis mosellana);

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

(7) Tick (Acari)
(A) Astigmata (Acaridida)
(A) Acaridae ticks, for example, Rhizoglyphus echinopus, Rhizoglyphus robini; Rhizoglyphus robini; for example, Tyrophagus spp. Tyrophagus neiswanderi, Tyrophagus perniciosus, Tyrophagus putrescentiae, Tyrophagus similis; Other, Acarus siro, Acetus

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

(B) Tenuipalpidae ticks, for example, Brevipalpus spp. From Brevipalpus spi, Brevipalpus obovatus, Brevipalpus phoenicis, Cactus russulus); for example, Tenuipalpus pacificus, Tenuipalpus zhizhilashviliae; other species, Tenuipalpus spp .; Other, Dolichotetranychus floridanus;
(C) Tick of the family Eriophyidae, for example, Aceria diospyri, Aceria ficus, Aceria japonica, Aceria kuko, Carnation of Aceria spp. Rust mites (Aceria paradianthi), Black spider mites (Aceria tiyingi), Tulip spider mites (Aceria tulipae), Shibahamakifushi mite (Aceria zoysiea); for example, Eriophyes spp. emarginatae); eg, Aculops spp., Aculops lycopersici, Aculops pelekassi; eg, Aculus spp., Aculus fockeui, Aculus fockeui schlechtendali); Others, Acaphylla theavagrans, Chano Bidani (Calacarus carinatus), grape leaf burrowing mite (Colomerus vitis), grape rust mite (Calepitrimerus vitis), Nashisabidani (Epitrimerus pyri), Kinmoku rust mite (Paraphytoptus kikus), Makisabidani (Paracalacarus podocarpi), luchuensis tangerine rust mite (Phyllocotruta citri);
(D) Mites of the family Transonemidae (eg, Tarsonemus spp.), Tarsonemus bilobatus, Tarsonemus waitei; Others, Phytonemus pallidus, lamus );
(E) Penthaleidae mites, for example, Penthaleus spp., Penthaleus erythrocephalus, Penthaleus major;

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

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

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

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

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

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

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

(21) Voltage-gated sodium channel blockers: indoxacarb, metaflumizone;
(22) Acetyl CoA carboxylase inhibitor: spirodiclofen, spiromesifen, spirotetramat;
(23) Mitochondrial electron transport system complex IV inhibitor: aluminum phosphide, calcium phosphide, phosphine, zinc phosphide, cyanide;
(24) Mitochondrial electron transport system complex II inhibitor: sienopyrafen, cyflumetofen;
(25) Ryanodine receptor modulators: chlorantraniliprole, cyantraniprole, fulvendiamide;
(26) Mixed function oxidase inhibitor compound: piperonyl butoxide;
(27) Latrophilin receptor agonist: depsipeptide, cyclic depsipeptide, 24-membered cyclic depsipeptide, emodepside;
(28) Other agents (the mechanism of action is unknown): azadirachtin, benzoxymate, biphenazate, bromopropyrate, quinomethionate, cryolite, dicophore, pyridalyl, pyrifluquinazone; bencrothiaz, sulfur, amidoflumet, chlordimeform, 1,3-dichloro Propene, DCIP, phenisobromolate, benzomate, metaldehyde, chlorbenzilate, clothiazoben, dicyclanyl, phenoxacrime, phentriphanyl, flubenzimine, fluphenazine, gossip lure, japonyla, methoxadiazone, petroleum, potassium oleate, tetrasulfur, trialacene Afidopyropen, piflubumide, furometokin, flufiprole, fluenesulfone, meperfluthuri , Tetramethylfluthrin, tralopyryl, dimefluthrin, methylneodecanamide; fluralaner, 5- [5- (3,5-dichlorophenyl) -5-trifluoro-4,5-dihydroisooxal-3-yl] -2- (1H-1,2,4-triazol-1-yl) benzonitrile (CAS: 943137-49-3), 2'-bromo-2-fluoro-4 '-(heptafluoropropan-2-yl) -3 -(N-methylbenzamide) -6 '-(trifluoromethyl) benzanilide (CAS: 1207727-04-5), other metadiamides;

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

Below, the specific example of a disinfectant is shown.
(1) Nucleic acid biosynthesis inhibitors:
(A) RNA polymerase I inhibitor: benalaxyl, benalaxyl-M, furaxyl, metalaxyl, metalaxyl-M; oxadixil; cloziracone, off-race;
(B) adenosine deamylase inhibitor: buprimate, dimethylylmol, ethylimol;
(C) DNA / RNA synthesis inhibitors: Himexazole, octirinone;
(D) DNA topoisomerase II inhibitor: oxophosphate;

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

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

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

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

(6) Lipid and cell membrane synthesis inhibitors:
(A) Phospholipid biosynthesis, methyltransferase-inhibitors: edifenphos, iprobenphos, pyrazophos; isoprothiolane;
(B) lipid peroxidants: biphenyl, chloroneb, dichlorane, kinden, technazene, tolcrofosmethyl; etridiazole;
(C) Agents that act on cell membranes: iodocarb, propamocarb, propamocarb hydrochloride, propamocarbfocetylate, prothiocarb;
(D) Microbial disturbance of pathogen cell membrane: Bacillus subtilis, Bacillus subtilis QST713 strain, Bacillus subtilis FZB24 strain, Bacillus subtilis MBI600 strain, Bacillus subtilis strain D747 strain;
(E) Agents that disrupt the cell membrane: an extract of Goseika Yupte (Tea Tree);

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

(8) Cell wall synthesis inhibition (a) Trehalose and inositol biosynthesis agent: Validamycin;
(B) chitin synthase inhibitor: polyoxin, polyoxolim;
(C) Cellulose synthase inhibitor: dimethomorph, furmorph, pyrimorph; Bench Avaricarb, Iprovaricarb, Toluprocarb, Variphenate; Mandipropamide;

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

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

(11) Agents with unknown activity: Simoxanyl, fosetylaluminum, phosphoric acid (phosphate), teclophthalam, triazoxide, fursulfamide, dichromedin, metasulfocarb, cyflufenamide, metolaphenone, pyriophenone, dodin, dodin free base, fluthianyl;

(12) Agent having multiple action points: copper (copper salt), Bordeaux liquid, copper hydroxide, copper naphthalate, copper oxide, copper oxychloride, copper sulfate, sulfur, sulfur product, calcium polysulfide; farbum, mancozeb, maneb) , Mancopper, methylam, polycarbamate, propineb, thiram, dineb, ziram; captan, captahol, phorpet; chlorothalonil; dicloflurane, tolylfluanid; Quinomethionate; fluorimide;

(13) Other agents: DBEDC, fluorophorpet, guazatine acetate, bis (8-quinolinolato) copper (II), propamidine, chloropicrin, ciprofuram, Agrobacterium, betoxazine, diphenylamine, methylisothiocyanate (MITC) , Mildeomycin, Capsaicin, Carvone, Cufraneb, Cyprosulfamide, Dazomet, Debacarb, Dichlorophene, Diphenzoquat, Diphenzoquat methylsulfonate, Flumetober, Focetyl calcium, Focetyl sodium, Irumamycin, Natamycin, Nitrotal Isopropyl, oxamocarb, sodium propamocin, pyrrolnitrin, tebufloquine, torniphanide, zaliramide, Algophase, amicalthiazole (Amicarthiazol) ), Oxathiapiprolin, methylam zinc, benazole, tricramide, uniconazole, mildeomycin, Oxyfenthiin, picarbutrazox;

Furthermore, the specific example of a plant regulator is shown.
Abscisic acid, kinetin, benzylaminopurine, 1,3-diphenylurea, forchlorfenuron, thidiazuron, chlorfenuron, dihydrozeatin, gibberellin A, gibberellin A4, gibberellin A7, gibberellin A3, 1-methylcyclopropane, N-acetyl Aminoethoxyvinylglycine (aviglycine), aminooxyacetic acid, silver nitrate, cobalt chloride, IAA, 4-CPA, cloprop, 2,4-D, MCPB, indole-3-butyric acid, dichloroprop, phenthiol, 1-naphthyl Acetamide, ethiclozate, cloxyphonac, maleic hydrazide, 2,3,5-triiodobenzoic acid, salicylic acid, methyl salicylate, (−)-jasmonic acid, methyl jasmonate, (+)-strigol, (+)-deoxy Cistrigor, (+)-Orobancol, (+)-Sorgolactone, 4-oxo-4- (2-phenylethyl) aminobutyric acid; Ethephon, chlormequat, mepiquat chloride, benzyladenine;

[External parasite control agent]
The ectoparasite control agent of the present invention contains at least one selected from the compounds of the present invention as an active ingredient. The compound of the present invention is excellent in the control effect of ectoparasites that are harmful to humans.

Examples of ectoparasites include ticks, lice and fleas.
Examples of host animals to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; domestic animals such as cattle, horses, pigs and sheep; It is done. In addition, a bee is mentioned.
Ectoparasites parasitize in and on host animals, particularly warm-blooded animals. Specifically, it infests the back, underarms, lower abdomen, and inner crotch of the host animal and obtains nutrients such as blood and dandruff from the animal.

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

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

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

[Control agents for other pests]
In addition, pests that have poisonous needles and venom and cause damage to humans, pests that carry various pathogens and pathogens, and pests that cause discomfort to humans (toxic pests, sanitary pests, and unpleasant pests) Is excellent.
The specific example is shown below.
(1) Hymenoptera pest bee of Argidae, bee of Cynipidae, bee of Diprionidae, bee of Formicidae, bee of Mutillidae, Bee of Tenthredinidae, Bee of Vespidae;

(2) Other insect pest cockroaches (Blattodea), termites (termite), spiders (Araneae), centipedes (cetipede), millipede (millipede), crustaceans (crustacea);

[Prescription formulation]
Some preparation formulations of the pest control agent, insecticide or acaricide of the present invention, or ectoparasite control agent are shown, but the additives and addition ratios are not limited to these examples, It is possible to change. The parts in the formulation of the preparation indicate parts by weight.

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

(Formulation 1: wettable powder)
Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above was uniformly mixed and finely pulverized to obtain a wettable powder with 40% active ingredient.

(Formulation 2: Emulsion)
Compound of the present invention 30 parts Xylene 33 parts Dimethylformamide 30 parts Polyoxyethylene alkylallyl ether 7 parts The above components were mixed and dissolved to obtain an emulsion containing 30% active ingredient.

(Formulation 3: Granules)
Compound of the present invention 5 parts Talc 40 parts Clay 38 parts Bentonite 10 parts Sodium alkyl sulfate 7 parts The above components are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm, and the active ingredient is 5%. Get the granules.

(Formulation 4: Granules)
Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctylsulfosuccinate sodium salt 1 part Potassium phosphate 1 part The above components are pulverized and mixed well, water is added and kneaded, granulated and dried, and then 5% active ingredient. Get the granules.

(Formulation 5: Suspension)
Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts The above is mixed and wet milled until the particle size is 3 microns or less, A suspension with 10% active ingredient is obtained.

  The formulation of the ectoparasite control agent is shown below.

(Formulation 6: Granules)
Compound of the present invention 5 parts Kaolin 94 parts White carbon 1 part The compound of the present invention is dissolved in an organic solvent, sprayed onto a carrier, and then the solvent is evaporated under reduced pressure. This type of granule can be mixed with animal food.

(Formulation 7: Injection)
Compound of the present invention 0.1-1 part Peanut oil Balance After preparation, filter sterilize with a sterilization filter.

(Formulation 8: Pour-on agent)
Compound of the present invention 5 parts Myristic acid ester 10 parts i-propanol Balance

(Formulation 9: Spot-on agent)
Compound of the present invention 10-15 parts Palmitic acid ester 10 parts i-propanol Balance

(Formulation 10: Spray-on agent)
Compound of the present invention 1 part Propylene glycol 10 parts i-propanol Balance

  Next, an Example is shown and this invention is demonstrated more concretely. However, the present invention is not limited by the following examples.

[Example 1]
3- (2,2,2-trifluoroethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotinamide [3- (2,2,2-trifluoroethylthio) -N- ( Synthesis of 5- (trifluoromethyl) pyridin-2-yl) isonicotinamide] (Compound No. 1-21) (Step 1) Synthesis of 3-fluoroisonicotinic acid 18 ml of tetramethylethylenediamine was dissolved in 600 ml of tetrahydrofuran. And cooled to −40 ° C. under a nitrogen atmosphere. At −40 ° C., 51 ml of a 2.6M n-hexane solution of n-butyllithium was added dropwise, and the mixture was stirred at −20 ° C. for 0.5 hour. Then, it cooled to -70 degreeC. Next, 12 g of 3-fluoropyridine was added dropwise at −70 ° C., and the mixture was stirred at −70 ° C. for 1 hour. Thereafter, dry ice was added thereto at -70 ° C. The mixture was warmed to room temperature and stirred for 1 hour. The reaction solution was poured into ice water and concentrated hydrochloric acid was added dropwise to adjust the pH to 1. The precipitated solid was collected by filtration, suspended in toluene, and then concentrated under reduced pressure to obtain 10.1 g (yield 57%) of the desired product.

(Step 2) Synthesis of methyl 3-fluoroisonicotinate 7.0 g of 3-fluoropicolinic acid was suspended in 80 ml of methanol. To this, 18 g of thionyl chloride was added dropwise at room temperature, and the mixture was stirred overnight at room temperature. The reaction solution was poured into a saturated aqueous sodium bicarbonate solution and then extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 5.7 g (yield 74%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl3): δ 8.61 (d, 1H), 8.53 (m, 1H), 7.74 (m, 1H), 3.97 (s, 3H).

(Step 3) Synthesis of methyl 3- (methylthio) isonicotinate 1.0 g of methyl 3-fluoroisonicotinate was dissolved in 10 ml of dimethylformamide. To this, 0.57 g (purity 95%) of methyl mercaptan sodium was added at room temperature and stirred overnight. The reaction solution was poured into water and then extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 1.1 g (yield 91%) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl3): δ 8.58 (s, 1H), 8.45 (d, 1H), 7.73 (d, 1H), 3.94 (s, 3H), 2.56 (s, 3H).

(Step 4) Synthesis of methyl 3- (methylsulfinyl) isonicotinate 1.1 g of methyl 3- (methylthio) picolinate was dissolved in 30 ml of dichloromethane. To this, 1.5 g (purity 70%) of metachloroperbenzoic acid was added at room temperature and stirred overnight. The reaction solution was poured into a mixed aqueous solution of sodium thiosulfate and sodium hydrogen carbonate, and then extracted with dichloromethane. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.50 g of the desired product (yield 42%).
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl3): δ 9.46 (s, 1H), 8.92 (d, 1H), 7.84 (d, 1H), 3.98 (s, 3H), 2.94 (s, 3H).

(Step 5) Synthesis of methyl 3- (2,2,2-trifluoromethylthio) isonicotinate [methyl 3- (2,2,2-trifluoroethylthio) isonicotinate] To 8 ml of trifluoroacetic anhydride, methyl 3- (methylsulfinyl) ) 0.50 g of isonicotinate was dissolved. This was stirred at room temperature for 10 minutes. Then, it heated up at 50 degreeC and stirred for 30 minutes. Next, the reaction solution was concentrated under reduced pressure, 2.8 ml of methanol and 2.8 ml of triethylamine were added, and the mixture was stirred at room temperature for 1 hour. Subsequently, the reaction solution was concentrated under reduced pressure to obtain a crude product of methyl 3-mercaptoisonicotinate.
The obtained crude product of methyl 3-mercaptoisonicotinate was dissolved in 10 ml of dimethylformamide. To this, 1.0 g of potassium carbonate and 0.70 g of 2,2,2-trifluoroethyl trifluoromethanesulfonate were added at room temperature and stirred overnight. The reaction solution was poured into water and then extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 0.27 g (43% yield) of the desired product.
¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl3): δ 8.79 (s, 1H), 8.60 (d, 1H), 7.68 (d, 1H), 3.97 (s, 3H), 2.61 (q, 2H).

(Step 6) 3- (2,2,2-trifluoroethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotinamide [3- (2,2,2-trifluoroethylthio) -N- (5- (trifluoromethyl) pyridin-2-yl) isonicotinamide]

  0.18 g of 2-amino-5- (trifluoromethyl) pyridine was dissolved in 10 ml of tetrahydrofuran and cooled to 0 ° C. 1.7 ml of a 1.3M tetrahydrofuran solution of hexamethyldisilazane lithium was added dropwise thereto at 0 ° C. After completion of dropping, the mixture was stirred at 0 ° C. for 10 minutes. Next, 5 ml of a tetrahydrofuran solution containing 0.27 g of methyl 3- (2,2,2-trifluoromethylthio) isonicotinate was added dropwise at 0 ° C. After completion of dropping, the mixture was stirred at 0 ° C. for 1 hour. The reaction solution was poured into water and then extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure to obtain 0.14 g (yield 33%) of the desired product.

  The compounds of the present invention produced according to the above-described method are shown in Tables 1, 2 and 3. Table 1 shows substituents of the compound represented by the formula (1). Table 2 shows substituents of the compound represented by the formula (2). Table 3 shows the substituents of the compound represented by the formula (3). According to the description of the present specification, other compounds not specifically shown in the present specification, that is, those substituted with various groups that do not depart from the spirit and scope of the present invention can be produced and used by the above-described methods. It can be easily understood by those skilled in the art.

* 1 in Table 1 represents a 3- (1H-pyrazol-1-yl) pyridin-4-yl-carbonyl group.
The physical properties of the compounds shown in Table 1, Table 2, and Table 3 were measured. The measurement results are shown below. The leftmost number corresponds to the compound number in the table.
1-1: Melting point 140-141 ° C
1-2: Refractive index (22.2 ℃) 1.5615
1-3: Melting point 160-161 ° C
1-4: Melting point 180-182 ° C
1-5: Refractive index (24.3 ℃) 1.5587
1-6: Refractive index (24.2 ℃) 1.5538
1-7: Refractive index (24 ℃) 1.5386
1-8: ¹ H-NMR (400 MHz, CDCl 3, 23 ° C.): δ 8.75 (s, 2H), 8.54 (m, 3H), 7.92 (m, 3H), 7.86 (m, 2H), 7.59 (d, 1H), 7.20 (m, 2H), 6.56 (t, 2H).
1-9: Melting point 143-145 ° C
1-10: Melting point 160-162 ° C
1-11: Melting point 130-132 ℃
1-12: Melting point 85-87 ℃
1-13: Melting point 148-150 ℃
1-14: Melting point 106-108 ℃
1-15: ¹ H-NMR (400 MHz, DMSO-d6, 23 ° C.): δ 8.79 (s, 1H), 8.58 (d, 1H), 8.51 (s, 1H), 8.00-7.95 (m, 2H ), 7.67 (s, 1H), 7.52 (d, 1H), 7.45 (d, 1H), 6.46 (t, 1H), 3.29 (s, 3H).
1-16: Melting point 150-152 ° C
1-17: Melting point 130-133 ℃
1-18: Refractive index (22.7 ℃) 1.5506
1-19: Refractive index (20.7 ℃) 1.5507
1-20: ¹ H-NMR (400 MHz, CDCl3, 23 ° C.): δ 9.76 (br, 1H), 8.77 (s, 1H), 8.63 (d, 1H), 8.55 (d, 1H), 8.50 (s, 1H), 7.98 (d, 1H), 7.71 (d, 1H), 3.02 (q, 2H), 1.33 (t, 3H).
1-21: ¹ H-NMR (400 MHz, CDCl 3, 23 ° C.): δ 8.93 (br, 1H), 8.92 (s, 1H), 8.74 (d, 1H), 8.57 (s, 1H), 8.47 (d, 1H), 8.03 (d, 1H), 3.54 (q, 2H).
1-22: Melting point 130-131 ℃
1-23: Melting point 240-242 ℃
1-24: Melting point 111-113 ℃
1-25: Melting point 104-106 ℃
1-26: ¹ H-NMR (400 MHz, CDCl 3, 23 ° C.): δ 10.09 (br, 1H), 9.59 (s, 1H), 9.63 (s, 1H), 8.61 (s, 1H), 8.51 (d, 1H), 7.99 (d, 1H), 3.92 (q, 2H), 1.40 (t, 3H).
1-27: melting point 145-146 ℃
1-28: ¹ H-NMR (400 MHz, CDCl 3, 23 ° C.): δ 9.71 (br, 1H), 8.78 (s, 1H), 8.65 (d, 1H), 8.53 (s, 1H), 8.49 (d, 1H), 7.97 (d, 1H), 7.72 (d, 1H), 3.52 (s, 3H), 3.05 (q, 3H), 1.35 (t, 3H).
1-29: melting point 172-174 ° C
1-30: Melting point 249-252 ° C
1-31: Refractive index (20.6 ° C) 1.5191
1-32: Refractive index (20.5 ℃) 1.5223
1-33: ¹ H-NMR (400 MHz, DMSO-d6, 23 ° C.): δ 9.05 (s, 1H), 8.86 (d, 1H), 8.57 (s, 1H), 8.06 (d, 1H), 7.88 ( d, 1H), 7.51 (d, 1H), 3.40 (q, 2H), 1.18 (t, 3H).
1-34: Melting point 126-129 ℃
1-35: Melting point 143-147 ° C (hydrochloride)
1-36: ¹ H-NMR (400MHz, CDCl3, 23 ° C): δ 9.36 (br, 1H), 8.77 (s, 1H), 8.63 (d, 1H), 8.50 (s, 1H), 7.81 (s, 1H), 7.74 (d, 1H), 3.04 (q, 2H), 2.45 (s, 3H), 1.32 (t, 3H).
1-37: ¹ H-NMR (400 MHz, CDCl 3, 23 ° C.): δ 9.21 (s, 1H), 8.98 (d, 1H), 8.61 (s, 1H), 8.35 (s, 1H), 7.78 (s, 1H), 7.61 (d, 1H), 3.46 (q, 2H), 2.46 (s, 3H), 1.32 (t, 3H).
1-38: ¹ H-NMR (400MHz, CDCl3, 23 ° C): δ 8.67 (s, 1H), 8.62 (s, 2H), 8.54 (d, 1H), 8.10 (s, 1H), 8.09 (d, 1H), 3.17 (q, 2H), 1.45 (t, 3H).
1-39: Melting point 139-142 ° C
1-40: Melting point 111-114 ° C
1-41: Melting point 124-126 ° C
1-42: Melting point 144-146 ° C
1-43: ¹ H-NMR (400MHz, CDCl3, 23 ° C): δ 8.75 (m, 2H), 8.32 (m, 2H), 8.07 (br s, 1H), 7.90 (m, 1H), 7.64 (m , 1H), 7.46 (m, 3H), 7.23 (m, 2H).
1-44: ¹ H-NMR (400 MHz, CDCl3, 23 ° C.): δ 9.84 (br s, 1H), 8.80 (m, 1H), 8.76 (s, 1H), 8.50 (m, 1H), 8.39 ( m, 1H), 7.93-7.81 (m, 4H), 6.55 (m, 1H).
1-45: ¹ H-NMR (400MHz, CDCl3, 23 ° C): δ 10.58 (br s, 1H), 9.32 (s, 1H), 8.89 (s, 1H), 8.58 (m, 1H), 8.37 (m , 1H), 7.86 (m, 1H), 7.50-7.38 (m, 5H).
1-46: Melting point 143-145 ° C
1-47: Melting point 70-71 ℃
1-48: melting point 129-131 ° C
1-49: melting point 177-179 ° C
1-50: Melting point 148-150 ℃
1-51: Melting point 146-148 ℃
1-52: Melting point 280-283 ℃
1-53: Melting point 109-112 ℃
1-54: Refractive index (21.6 ℃) 1.5414
1-55: ¹ H-NMR (400 MHz, CDCl 3, 140 ° C.): δ 8.99 (s, 1H), 8.85 (d, 1H), 8.51 (s, 1H), 8.07 (d, 1H), 7.47 (d, 1H), 3.32 (q, 2H), 3.27 (s, 3H), 1.14 (t, 3H).
1-56: Melting point 84-86 ° C
1-57: Melting point 145-148 ℃
1-58: Melting point 101-103 ℃

2-1: Melting point 130-134 ° C
2-2: Melting point 138-141 ° C

3-1: Melting point 77-80 ° C
3-2: Melting point 105-107 ° C
3-8: Melting point 130-135 ℃
3-9: Melting point 300 ° C
3-10: Melting point 154-157 ° C
3-11: Melting point 160-163 ° C
3-12: Melting point 130-135 ℃
3-13: Melting point 103-106 ℃
3-15: Melting point 150-153 ° C
3-17: Melting point 157-160 ° C
3-18: Melting point 177-180 ℃
3-19: Melting point 161-163 ° C
3-20: Melting point 126-129 ℃
3-21: Melting point 100-103 ℃
3-22: Melting point 156-158 ° C
3-23: Melting point 80-85 ℃

[Biological test]
The following test examples show that the compounds of the present invention are useful as active ingredients for pest control agents, particularly insecticides. “Part” means “part by weight”.

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

(Test Example 1) Efficacy test on bean aphids Adult bean aphids were released on cowpeas with primary leaves developed. On the day after the release, the first-instar larvae that were delivered were left and the adults were removed.
Emulsion (I) was diluted with water to a compound concentration of 125 ppm. This diluted solution was sprayed on the cowpea. The cowpea was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. And the life or death of the bean aphid was examined on the day after 4 days from the spraying, and the insecticidal rate was determined.

  Compound Nos. 1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-11, 1-14, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-24, 1-25, 1-27, 1-28, 1-31, 1- 32, 1-33, 1-34, 1-35, 1-36, 1-37, 1-39, 1-40, 1-41, 1-43, 1-44, 1-45, 1-46, Contains 1-47, 1-48, 1-50, 1-51, 1-53, 1-54, 1-55, 1-56, 1-58, 3-10, and 3-20 compounds, respectively. Emulsion (I) was tested for efficacy against legume aphids. All the compounds were 80% or more.

(Test Example 2) Efficacy test against brown planthopper Emulsion (I) was diluted with water to a compound concentration of 125 ppm. Rice seedlings were immersed in this diluted solution for 10 seconds and then air-dried. A plastic bag with holes was put on rice seedlings. Ten second instar larvae were released in a bag. This was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. Then, on the day after 6 days from the release of the insects, the survival of the green planthopper was examined and the insecticidal rate was determined. In addition, as a brown planthopper, a drug-insensitive line (a line collected in Kumamoto Prefecture in 2011 and kept indoors) was used.

  Compound numbers 1-2, 1-4, 1-5, 1-8, 1-9, 1-11, 1-16, 1-17, 1-19, 1-20, 1-21, 1-22, Contains 1-24, 1-25, 1-27, 1-28, 1-29, 1-31, 1-34, 1-35, 1-38, 1-39, and 1-40 compounds, respectively Emulsion (I) was tested for efficacy against brown planthopper. All compounds had an insecticidal rate of 80% or more.

  The green planthopper used showed an insecticidal rate of 50% in an efficacy test with an emulsion containing imidacloprid (125 ppm) and an insecticidal rate of 70% in an efficacy test with an emulsion containing buprofezin (125 ppm).

(Test Example 3) Efficacy test against tobacco whitefly Emulsion (I) was diluted with water to a compound concentration of 125 ppm. The diluted solution was sprayed on tomato cut leaves and then air-dried. The tomato cut leaves were placed in a flask and fixed with absorbent cotton so that the leaf surface faced upward. To this flask, 7 pairs of tobacco whitefly type B adults were released and parasitized on tomato cut leaves. This was placed in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. On the day after 2 days from the release, the larvae that were delivered were left and the adults were removed. The number of surviving larvae was examined on the 12th day after the release. Here, the efficacy of the compound was evaluated by the next generation control rate shown below.
Next generation control rate = 100-{(T × Ca) / (Ta × C)} × 100
Ta: Number of parasites immediately after release in the spray treatment area
T: Number of parasites 12 days after release
Ca: Number of parasites immediately after release in the untreated area
C: Number of parasites 12 days after release in the untreated area

  Compound Nos. 1-2, 1-3, 1-4, 1-6, 1-7, 1-8, 1-9, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-24, 1-25, 1-27, 1-28, 1-31, 1-33, 1-35, 1-41, 1-43, 1-44, 1- Emulsion (I) containing 48 and 1-50 compounds, respectively, was tested for efficacy against whiteflies. All the compounds had a next-generation control rate of 80% or more.

  Provided are a pyridine compound which has excellent insecticidal activity and / or acaricidal activity, is excellent in safety and can be synthesized industrially advantageously, and a pest control agent containing the pyridine compound as an active ingredient.

Claims (4)

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

In formula (I),
R ¹ represents a C 1-6 alkyl group, a C 1-6 haloalkyl group, a C 1-6 haloalkoxy group, a C 1-6 alkoxy C 1-6 haloalkyl group, a halogeno group, a cyano C 1-6 alkyl group, a dioxolanyl group, or a formyl group. Show.
X ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, formyl group, unsubstituted or substituted C1-6 alkylcarbonyl group, unsubstituted or substituted C1-6 alkoxycarbonyl group, amino group, unsubstituted Or a substituted C1-6 alkylamino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group having a group, unsubstituted or substituted C3-8 cycloalkyl group Unsubstituted or C6~10 aryl group having a substituent, 3- to 6-membered heterocyclyl group having unsubstituted or substituted group, halogeno group, a cyano group or a nitro group.
m represents the number of X ¹ and is an integer from 0 to 3. When m is 2 or more, X ¹ may be the same as or different from each other.
X ² is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 alkynyl group, a hydroxyl group, an unsubstituted group Or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, formyl group, unsubstituted or substituted A C1-6 alkylcarbonyl group having a group, a carboxyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an amino group, an unsubstituted or substituted C1-6 alkylamino group, an aminocarbonyl group, Unsubstituted or substituted C1-6 alkylaminocarbonyl group, mercapto group, unsubstituted Is a substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, formyloxy group, unsubstituted or substituted A C1-6 alkylcarbonyloxy group having a group, an unsubstituted or substituted C1-6 alkoxycarbonyloxy group, an aminocarbonyloxy group, an unsubstituted or substituted C1-6 alkylaminocarbonyloxy group, Substituted or substituted C1-6 alkylsulfonyloxy groups, unsubstituted or substituted C3-8 cycloalkyl groups, unsubstituted or substituted C4-8 cycloalkenyl groups, unsubstituted or substituted C6-10 aryl group having a group, unsubstituted or substituted A C6-10 aryloxy group having an alkyl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, an unsubstituted or substituted C6-10 arylthio group, an unsubstituted or substituted C6-10 aryl A sulfinyl group, a halogeno group, a cyano group, or a nitro group is shown.
n shows the number of X < ² > and is an integer in any one of 0-3. When n is 2 or more, X ² may be the same as or different from each other.
R ² represents a hydrogen atom, an unsubstituted or substituted C 1-6 alkyl group, an unsubstituted or substituted C 2-6 alkenyl group, an unsubstituted or substituted C 2-6 alkynyl group, A substituted or substituted C1-6 alkoxy group, a formyl group, an unsubstituted or substituted C1-6 alkylcarbonyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or A C1-6 alkylsulfonyl group having a substituent, an unsubstituted or substituted C6-10 arylcarbonyl group, or an unsubstituted or substituted 3-6 membered heterocyclylcarbonyl group is shown.
Z represents an oxygen atom or a sulfur atom.
B ¹ , B ² , and B ³ each independently represent a carbon atom or a nitrogen atom, and any one or two of them represent a nitrogen atom.   A pest control agent comprising at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An insecticide or acaricide containing at least one selected from the group consisting of the compound according to claim 1 and a salt thereof as an active ingredient.   An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the compound according to claim 1 and a salt thereof.