WO2014065209A1 - Pyridine compound or salt thereof, pest control agent, insecticide or acaricide, and ectoparasite control agent - Google Patents

Abstract

Provided are: a pyridine compound or a salt thereof that has excellent insecticidal activity and/or acaricidal activity, is highly safe, and can be synthesized industrially advantageously; and a pest control agent including the same as an active ingredient. Disclosed is a pyridine compound represented by formula (I), or a salt thereof. In the formula (I): R¹ represents a C_1-6 haloalkyl group, etc.; X¹ represents a substituted or unsubstituted C_1-6 alkyl group, a halogeno group, etc.; m represents the number of X¹s and is an integer from 0 to 3; R² represents a substituted or unsubstituted C_1-10 alkoxy group, etc.; X² represents a substituted or unsubstituted C_1-6 alkyl group, a halogeno group, etc.; n represents the number of X²s and is an integer from 0 to 3; Z represents an oxygen atom, etc.; and A represents a substituted or unsubstituted C_1-6 alkylene group.

Description

Pyridine compounds or salts thereof, pest control agents, insecticides or acaricides, and ectoparasite control agents

The present invention relates to a pyridine compound or a salt thereof, a pest control agent, an insecticide or an acaricide, and an ectoparasite control agent. More specifically, the present invention relates to a pyridine compound or a salt thereof that has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously, and harmful substances containing this as an active ingredient. The present invention relates to biocontrol agents, insecticides or acaricides, and ectoparasite control agents.
This application claims priority based on Japanese Patent Application No. 2012-234108 filed in Japan on October 23, 2012, and Japanese Patent Application No. 2013-099742 filed in Japan on May 9, 2013, The contents are incorporated here.

Various compounds having insecticidal / miticidal activity have been proposed. For example, Patent Document 1 describes a 2,6-dichloro-4-pyridinemethanol derivative. 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 or a salt thereof that has excellent pesticidal activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized industrially advantageously. It is to provide a pest control agent containing an active ingredient as an active ingredient, and an insecticide or acaricide. 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 or a salt thereof has excellent insecticidal activity and / or acaricidal activity, and has 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 pyridine compound represented by the formula (I) or a salt thereof.

[In the formula (I),
R ¹ represents a C1-6 haloalkyl group or a C1-6 alkoxy C1-6 haloalkyl 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, unsubstituted or Substituted C3-8 cycloalkyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1 -6 alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or A substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted one Or a 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group having a substituent.
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.
R 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, unsubstituted or Having a substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, a hydroxyl group, an unsubstituted or substituted C1-10 alkoxy group, an unsubstituted or substituted group C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C1-7 acyl group, carboxyl group, unsubstituted or substituted C1-6 Alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted aminocarbonyl Group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C6-10 arylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted Group having C6-10 arylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C1-7 acyloxy group, unsubstituted or substituted C1-6 Alkoxycarbonyloxy group, substituted aminocarbonyloxy group, substituted amino (thiocarbonyl) oxy group, unsubstituted or substituted C1-6 alkylsulfonyloxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-1 An aryloxy group, an unsubstituted or substituted 3- to 6-membered heterocyclic group, an unsubstituted or substituted imino C1-6 alkyl group, an unsubstituted or substituted C1-6 alkylideneaminooxy group An unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfinimidoyl group, an unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfonimidoyl group , A halogeno group, a cyano group, or a nitro group.
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, unsubstituted or A substituted C3-8 cycloalkyl group, an oxo group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group A C1-6 alkoxycarbonyl group having an unsubstituted or substituted amino group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an A substituted or substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, An unsubstituted or substituted 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group is shown.
n represents the number of X ² and is an integer from 0 to 3. When n is 2 or more, X ² may be the same as or different from each other.
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by NR ³ .
R ³ represents a hydrogen atom, 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 substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted group; And a C1-6 alkylsulfonyl group having an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclic group, or a cyano group.
A represents an unsubstituted or substituted C1-6 alkylene group.
Here, R ² and A may be connected to each other to form a ring together with the carbon atom to which R ² and A are bonded. ]

[2] A pest control agent comprising as an active ingredient at least one selected from the group consisting of the pyridine compound according to [1] and a salt thereof.
[3] An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the pyridine compound according to [1] and a salt thereof.
[4] An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the pyridine compound according to [1] and a salt thereof.

The pyridine compound or a salt thereof of the present invention can control pests that are problematic in terms of crops and hygiene. 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)).

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 group serving as the mother nucleus has 1 to 6 carbon atoms. 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, n-hexyl group, etc. An alkyl group;
Vinyl group, 1-propenyl group, 2-propenyl group (allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group, etc. A C2-6 alkenyl group of
C2-6 alkynyl groups such as ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group;
A C3-8 cycloalkyl group such as a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group;
A C4-8 cycloalkenyl group such as a 2-cyclopentenyl group, a 3-cyclohexenyl group, a 4-cyclooctenyl group;

A C6-10 aryl group such as a phenyl group or a naphthyl group;
A C7-11 aralkyl group such as a benzyl group or a phenethyl group;
A 3-6 membered heterocyclic group;
A C1-7 acyl group such as a formyl group, an acetyl group, a propionyl group, a benzoyl group, a cyclohexylcarbonyl 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;
C2-6 alkynyloxy groups such as ethynyloxy group and propargyloxy group;
C6-10 aryloxy groups such as phenoxy group and naphthoxy group;
A C7-11 aralkyloxy group such as a benzyloxy group or a phenethyloxy group;

C1-7 acyloxy groups such as formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy 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;
A C1-6 alkoxycarbonyloxy group such as a methoxycarbonyloxy group, ethoxycarbonyloxy group, n-propoxycarbonyloxy group, i-propoxycarbonyloxy group, n-butoxycarbonyloxy group, t-butoxycarbonyloxy group;
Carboxyl group;

Halogeno groups such as fluoro, chloro, bromo and iodo groups;
C1-6 haloalkyl groups such as chloromethyl group, chloroethyl group, trifluoromethyl group, 1,2-dichloro-n-propyl group, 1-fluoro-n-butyl group, perfluoro-n-pentyl group;
A C2-6 haloalkenyl group such as a 2-chloro-1-propenyl group and a 2-fluoro-1-butenyl group;
A C2-6 haloalkynyl group such as 4,4-dichloro-1-butynyl group, 4-fluoro-1-pentynyl group, 5-bromo-2-pentynyl group;
C6-10 haloaryl group such as 4-chlorophenyl group, 4-fluorophenyl group, 2,4-dichlorophenyl group;
A C1-6 haloalkoxy group such as a trifluoromethoxy group, 2-chloro-n-propoxy group, 2,3-dichlorobutoxy group;
A C2-6 haloalkenyloxy group such as a 2-chloropropenyloxy group and a 3-bromobutenyloxy group;
C6-10 haloaryloxy groups such as 4-fluorophenyloxy group, 4-chloro-1-naphthoxy group;
C1-7 haloacyl groups such as chloroacetyl group, trifluoroacetyl group, trichloroacetyl group, 4-chlorobenzoyl group;

An amino group;
A C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, a diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
A C7-11 aralkylamino group such as a benzylamino group or a phenethylamino group;
C1-7 acylamino groups such as formylamino group, acetylamino group, propanoylamino group, butyrylamino group, i-propylcarbonylamino group, benzoylamino group;
A C1-6 alkoxycarbonylamino group such as a methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group;
An aminocarbonyl group having no substituent or a substituent such as an aminocarbonyl group, a dimethylaminocarbonyl group, a phenylaminocarbonyl group, an N-phenyl-N-methylaminocarbonyl group;
Imino C1-6 alkyl groups such as iminomethyl, (1-imino) ethyl, (1-imino) -n-propyl;
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 which is unsubstituted or has a substituent such as ethyl group;

A mercapto group;
C1-6 alkylthio groups such as methylthio group, ethylthio group, n-propylthio group, i-propylthio group, n-butylthio group, i-butylthio group, s-butylthio group, t-butylthio group;
A C6-10 arylthio group such as a phenylthio group or a naphthylthio group;
A heteroarylthio group such as a thiazolylthio group or a pyridylthio group;
A C7-11 aralkylthio group such as a benzylthio group or a phenethylthio group;
A C1-6 alkylsulfinyl group such as a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group;
A C6-10 arylsulfinyl group such as a phenylsulfinyl group;
Heteroarylsulfinyl groups such as thiazolylsulfinyl group, pyridylsulfinyl group;
A C7-11 aralkylsulfinyl group such as a benzylsulfinyl group or a phenethylsulfinyl group;
A C1-6 alkylsulfonyl group such as a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group;
A C6-10 arylsulfonyl group such as a phenylsulfonyl group;
A heteroarylsulfonyl group such as a thiazolylsulfonyl group or a pyridylsulfonyl group;
A C7-11 aralkylsulfonyl group such as a benzylsulfonyl group or a phenethylsulfonyl group;
An aminocarbonyloxy group;
A C1-6 alkyl-substituted aminocarbonyloxy group such as an ethylaminocarbonyloxy group or a dimethylaminocarbonyloxy group;
An amino (thiocarbonyl) oxy group;
A C1-6 alkyl-substituted amino (thiocarbonyl) oxy group such as a dimethylamino (thiocarbonyl) oxy group;

A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group;
A triaryl-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.

The “3- to 6-membered heterocyclic group” includes 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 heterocyclic group may be monocyclic or polycyclic. In the polycyclic heterocyclic group, if at least one ring is a heterocyclic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3- to 6-membered heterocyclic group” include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclic group, and the like.

Examples of the 3- to 6-membered saturated heterocyclic 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 pyridanidyl group, and a triazinyl group.

[R ¹ ]
In the formula (I), R ¹ represents a C1-6 haloalkyl group or a C1-6 alkoxy C1-6 haloalkyl group.
As the “C1-6 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 and a 2,4,6-trichlorohexyl group can be exemplified.
Examples of the “C1-6 alkoxy C1-6 haloalkyl group” in R ¹ include a methoxydifluoromethyl group and a 2,2,2-trifluoro-1-methoxy-1-trifluoromethylethyl group.

^[X 1, m]
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, unsubstituted or Substituted C3-8 cycloalkyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1 -6 alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or A substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted one Or a 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group having a substituent.
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 ¹ is preferably substituted at the position labeled 3 in formula (I).

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

As the “C1-6 alkyl group having a substituent”,
C3-8 cycloalkyl C1-6 alkyl groups 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-trifluoro Ethyl group, 2,2,2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1 -C1-6 haloalkyl groups such as trifluoromethylethyl group, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 1-hydroxyethyl group, 2-hydroxyethyl group;
C1˜ such as methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, etc. 6 alkoxy C1-6 alkyl groups;
C2-6 alkenyloxy C1-6 alkyl groups such as vinyloxymethyl group, allyloxymethyl group, propenyloxymethyl group, butenyloxymethyl group;
Heteroaryloxy C1-6 alkyl groups such as a pyridin-2-yloxymethyl group;
C1-7 acyl C1-6 alkyl group such as formylmethyl group, acetylmethyl group, propionylmethyl group;
C1-7 acyloxy C1-6 alkyl groups such as formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group;
Carboxyl group C1-6 alkyl group such as carboxylmethyl group and carboxylethyl group;
A C1-6 alkoxycarbonyl C1-6 alkyl group such as a methoxycarbonylmethyl group, an ethoxycarbonylmethyl group, an n-propoxycarbonylmethyl group, an i-propoxycarbonylmethyl group;
C1-7 acylamino C1-6 alkyl groups such as formamidomethyl group, acetamidomethyl group, 2-acetamidoethyl group, propionylaminomethyl group, propionylaminoethyl group;
C1-6 alkylamino such as methylaminocarbonylmethyl group, ethylaminocarbonylmethyl group, i-propylaminocarbonylmethyl group, t-butylaminocarbonylmethyl group, s-butylaminocarbonylmethyl group, n-pentylaminocarbonylmethyl group A carbonyl C1-6 alkyl group;
C1-6 such as methoxycarbonylaminomethyl group, ethoxycarbonylaminomethyl group, i-propoxycarbonylaminomethyl group, t-butoxycarbonylaminomethyl group, s-butyloxycarbonylaminomethyl group, n-pentyloxycarbonylaminomethyl group, etc. An alkoxycarbonylamino C1-6 alkyl group;
A C7-11 aralkyl group such as a benzyl group or a phenethyl group;
A C6-10 arylcarbonylamino C1-6 alkyl group such as a benzoylaminomethyl group;
A C1-6 alkylthio C1-6 alkyl group such as a methylthiomethyl group, an ethylthiomethyl group, a 1-methylthioethyl group;
A C1-6 alkylsulfinyl C1-6 alkyl group such as a methylsulfinylmethyl group, an ethylsulfinylmethyl group, a 1-methylsulfinylethyl group;
And C1-6 alkylsulfonyl C1-6 alkyl groups such as a methylsulfonylmethyl group, an ethylsulfonylmethyl group, and a 1-methylsulfonylethyl group.

As the “C2-6 alkenyl group” in 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.
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; 2-n-butoxy-vinyl group, 1 A C1-6 alkoxy C2-6 alkenyl group such as an ethoxy-vinyl group;

As the “C2-6 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 And a 1,1-dimethyl-2-butynyl group.
As the “substituted C2-6 alkynyl group”, a C2-6 haloalkynyl group such as a 4,4-dichloro-1-butynyl group, a 4-fluoro-1-pentynyl group, a 5-bromo-2-pentynyl group, etc. A tri-C1-6 alkyl-substituted silyl C2-6 alkynyl group such as a trimethylsilanylethynyl group;

Examples of the “C3-8 cycloalkyl group” for X ¹ include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, and a cycloheptyl group.

The “C1-6 alkoxy group” in X ¹ is a methoxy group, ethoxy group, n-propoxy group, n-butoxy group, n-pentyloxy group, n-hexyloxy group, i-propoxy group, i-butoxy group S-butoxy group, t-butoxy group, i-hexyloxy group and the like.
Examples of the “substituted C1-6 alkoxy group” include chloromethoxy group, dichloromethoxy group, difluoromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1-difluoroethoxy group, 2 , 2,2-trifluoroethoxy group, pentafluoroethoxy group, C1,6 haloalkoxy group such as 2,2,3,4,4,4-hexafluoro-butoxy group;
A C1-6 alkoxy C1-6 alkoxy group such as a methoxymethoxy group or a methoxyethoxy group;
A C3-8 cycloalkyl C1-6 alkoxy group such as a cyclopropylmethyloxy group;
(C6-10 aryl C3-8 cycloalkyl) C1-6 alkoxy groups such as (2-phenylcyclopropyl) methyloxy group;
A C1-6 alkyl-substituted amino C1-6 alkoxy group such as a dimethylaminoethoxy group;
An unsubstituted or substituted 5- to 6-membered heterocyclic C1-6 alkoxy group such as a tetrahydrofuranylmethoxy group, an unsubstituted or substituted pyridylmethoxy group;
And cyano C1-6 alkoxy groups such as cyanomethoxy group and 2-cyanoethoxy group;

Examples of the substituent on the 5-6 membered heterocycle in the “5-6 membered heterocycle C1-6 alkoxy group” include a C1-6 alkyl group, a C1-6 haloalkyl group, a hydroxyl group, a C1-6 alkoxy group, a halogeno group, A cyano group, a nitro group, etc. can be mentioned.

Examples of the “C1-7 acyl group” in X ¹ include a formyl group, an acetyl group, a propionyl group, and a benzoyl group.
Examples of the “substituted C1-7 acyl group” include C1-7 haloacyl groups such as a chloroacetyl group, a trifluoroacetyl group, a trichloroacetyl group, and a 4-chlorobenzoyl group.

Examples of the “C1-6 alkoxycarbonyl group” in X ¹ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and a t-butoxycarbonyl group.
As the “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;

Examples of the “amino group having a substituent” in X ¹ include C1-6 alkyl-substituted amino groups such as a methylamino group, an n-butylamino group, a dimethylamino group, and a diethylamino group.

Examples of the “C1-6 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. be able to.

Examples of the “C1-6 alkylsulfinyl group” in X ¹ include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.

Examples of the “C1-6 alkylsulfonyl group” for X ¹ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, and the like.

The “C6-10 aryl group” for 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 heterocyclic group” in X ¹ includes 1 to 4 heteroatoms selected from the group consisting of a nitrogen atom, an oxygen atom and a sulfur atom as constituent atoms of the ring. The heterocyclic group may be monocyclic or polycyclic. In the polycyclic heterocyclic group, if at least one ring is a heterocyclic ring, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring or an aromatic ring. Examples of the “3- to 6-membered heterocyclic group” include a 3- to 6-membered saturated heterocyclic group, a 5- to 6-membered heteroaryl group, a 5- to 6-membered partially unsaturated heterocyclic group, and the like.

Examples of the 3- to 6-membered saturated heterocyclic group include aziridinyl group, epoxy group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group (for details, [1,3] dioxolanyl group) And dioxanyl group (specifically, [1,3] dioxanyl group or [1,4] dioxanyl group). A 5- to 6-membered saturated heterocyclic ring is preferable.

Examples of the 5-membered heteroaryl group include a pyrrolyl group, a furyl group, a thienyl group, an imidazolyl group, a pyrazolyl group, an oxazolyl group, an isoxazolyl group, a thiazolyl group, an isothiazolyl group, and a triazolyl group (for details, [1,2,3] triazolyl group 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 pyridanidyl group, and a triazinyl group.

Examples of the partially unsaturated 5-membered heterocyclic 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 heterocyclic group include a thiopyranyl group, a 2H-pyridin-1-yl group, and a 4H-pyridin-1-yl group.

Substituents on “C6-10 aryl group” and “3-6 membered heterocyclic group” include C1-6 alkyl group, C1-6 haloalkyl group, oxo group, hydroxyl group, C1-6 alkoxy group, halogeno group, A cyano group, a nitro group, etc. can be mentioned.

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

[R ² ]
R 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, unsubstituted or Having a substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, a hydroxyl group, an unsubstituted or substituted C1-10 alkoxy group, an unsubstituted or substituted group C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C1-7 acyl group, carboxyl group, unsubstituted or substituted C1-6 Alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted aminocarbonyl Group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C6-10 arylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted Group having C6-10 arylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C1-7 acyloxy group, unsubstituted or substituted C1-6 Alkoxycarbonyloxy group, substituted aminocarbonyloxy group, substituted amino (thiocarbonyl) oxy group, unsubstituted or substituted C1-6 alkylsulfonyloxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-1 An aryloxy group, an unsubstituted or substituted 3- to 6-membered heterocyclic group, an unsubstituted or substituted imino C1-6 alkyl group, an unsubstituted or substituted C1-6 alkylideneaminooxy group An unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfinimidoyl group, an unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfonimidoyl group , A halogeno group, a cyano group, or a nitro group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C1-7 acyl group”, “C1-6 alkoxycarbonyl” for R ² Group "," amino group having a substituent "," C1-6 alkylthio group "," C1-6 alkylsulfonyl group "," C6-10 aryl group "," 3-6 membered heterocyclic group ", and" halogeno " Examples of the “group” and the group having a substituent in these groups are the same as those exemplified in X ¹ above.

The “C1-10 alkoxy group” in R ² and the group having a substituent in this group are the same as those exemplified in the above X ¹ , n-heptyloxy group, n-octyloxy group, n-nonyloxy group And n-decyloxy group.

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

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

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

Examples of the “substituted aminocarbonyl group” in R ² include C1˜, such as methylaminocarbonyl group, dimethylaminocarbonyl group, diethylaminocarbonyl group, i-propylaminocarbonyl group, methyl- (i-propyl) aminocarbonyl group and the like. A cyano C1-6 alkylamino substituted amino group such as a cyanomethylaminocarbonyl group; a hydroxy C1-6 alkylaminocarbonyl group such as a 2-hydroxyethylaminocarbonyl group; an N-methoxy-methylaminocarbonyl group, etc. N-alkoxy-substituted aminocarbonyl group;

Examples of the “C6-10 arylthio group” for R ² include a phenylthio group and a naphthylthio group. Examples of the substituent on the “6-10 arylthio group” include C1-6 alkyl group, hydroxyl group, C1-6 alkoxy group, halogeno group, cyano group, nitro group and the like.

Examples of the “C1-6 alkylsulfinyl group” for R ² include a methylsulfinyl group, an ethylsulfinyl group, a t-butylsulfinyl group, and the like.

Examples of the “C6-10 arylsulfinyl group” for R ² include a phenylsulfinyl group. Examples of the substituent on the “6-10 arylsulfinyl group” include a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a halogeno group, a cyano group, and a nitro group.

Examples of the “C1-7 acyloxy group” in R ² include formyloxy group, acetyloxy group, propionyloxy group, benzoyloxy group, cyclohexylcarbonyloxy group and the like.

The “C1-6 alkoxycarbonyloxy group” in R ² includes a methoxycarbonyloxy group, an ethoxycarbonyloxy group, an n-propoxycarbonyloxy group, an i-propoxycarbonyloxy group, an n-butoxycarbonyloxy group, a t-butoxycarbonyl group. An oxy group etc. can be mentioned.

Examples of the “substituted aminocarbonyloxy group” for R ² include C1-6 alkyl-substituted aminocarbonyloxy groups such as ethylaminocarbonyloxy group and dimethylaminocarbonyloxy group.

Examples of the “substituted amino (thiocarbonyl) oxy group” in R ² include C1-6 alkyl-substituted amino (thiocarbonyl) oxy groups such as dimethylamino (thiocarbonyl) oxy group.

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

Examples of the “C6-10 aryloxy group” for R ² include a phenyloxy group and a naphthoxy group. Examples of the substituent on the “6-10 aryloxy group” include a C1-6 alkyl group, a hydroxyl group, a C1-6 alkoxy group, a halogeno group, a cyano group, and a nitro group.

Examples of the “imino C1-6 alkyl group” for R ² include an iminomethyl group, a (1-imino) ethyl group, and a (1-imino) -n-propyl group.
As the “imino C1-6 alkyl group having a substituent”, N-C1-6 alkyl-imino C1-6 alkyl group such as N-methyl-iminomethyl group, N-ethyl-iminomethyl group, etc .; N-2-hydroxyethyl N-hydroxy C1-6 alkyl-iminomethyl group such as iminomethyl group; N-hydroxy-imino C1-6 alkyl group such as N-hydroxy-iminomethyl group (—CH═N—OH); N-methoxy-iminomethyl group ( -CH = N-OCH ₃ ), N- (i-propoxy) -iminomethyl group (-CH = N-O ⁱ Pr) and other N-C1-6 alkoxy-imino C1-6 alkyl groups; it can.

Examples of the “C1-6 alkylideneaminooxy group” in R ² include an ethylideneaminooxy group (—O—N═CH (CH ₃ )), an isopropylideneaminooxy group (—O—N═C (CH ₃ ) ₂ ). And so on.

Examples of the “N-cyano-S— (C1-6 alkyl) sulfinimidoyl group” in R ² include an N-cyano-S-methylsulfinimidoyl group (—S (═N—CN) (CH ₃ )) and the like. Can be mentioned.

As the “N-cyano-S— (C1-6 alkyl) sulfonimidoyl group” in R ² , an N-cyano-S-methylsulfonimidoyl group (—S (═O) (═N—CN) (CH ₃ )).

[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, unsubstituted or A substituted C3-8 cycloalkyl group, an oxo group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group A C1-6 alkoxycarbonyl group having an unsubstituted or substituted amino group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an A substituted or substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, An unsubstituted or substituted 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group is shown.
n represents the number of X ² and is an integer from 0 to 3. When n is 2 or more, X ² may be the same as or different from each other. X ² is preferably substituted at the position labeled 5 in formula (I).

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C1-6 alkoxy group”, “C1-7 acyl group” for X ² ”,“ C1-6 alkoxycarbonyl group ”,“ amino group having a substituent ”,“ C1-6 alkylthio group ”,“ C1-6 alkylsulfinyl group ”,“ C1-6 alkylsulfonyl group ”,“ C6-10 ” Examples of the “aryl group”, “3- to 6-membered heterocyclic group”, and “halogeno group” and the group having a substituent in these groups are the same as those exemplified for X ¹ above.

[Z, R ³ ]
Z represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by NR ³ .
R ³ represents a hydrogen atom, 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 substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted group; And a C1-6 alkylsulfonyl group having an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclic group, or a cyano group.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C1-7 acyl group”, “C1-6 alkoxycarbonyl” for R ³ “Group”, “C1-6 alkylsulfonyl group”, “C6-10 aryl group”, “3-6 membered heterocyclic group” and groups having substituents on these groups include those exemplified in the above X ¹ The same thing can be mentioned.

[A]
A represents an unsubstituted or substituted C1-6 alkylene group. Here, R ² and A may be connected to each other to form a ring together with the carbon atom to which R ² and A are bonded.

Examples of the “C1-C6 alkylene group” in A include a methylene group, an ethylene group, a trimethylene group, a tetramethylene group, a propane-1,2-diyl group (that is, a propylene group), and the like.
Examples of the substituent on the “C1 to C6 alkylene group” include a C1 to 6 alkyl group and a cyano group.

Examples of the “ring” formed by R ² and A connected to each other and the carbon atom to which they are bonded include a cyclopentene ring, a cyclohexene ring, and a benzene ring.

The salt of the pyridine compound of the present invention is a salt of compound (I). The salt is not particularly limited as long as it is an agro-horticulturally acceptable salt. For example, salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron and copper And salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like. The salt of a pyridine compound can be obtained from compound (I) by a known method.

The pyridine compound and its salt of the present invention are not particularly limited by the production method. The pyridine compound and salts thereof of the present invention can be obtained by known production methods described in Examples and the like.

[Pesticides]
The pyridine compound of the present invention or a salt thereof (hereinafter sometimes referred to as “the present compound”) is excellent in the effect of controlling various pests such as agricultural pests and mites that affect the growth of plants. 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 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 a lack of 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 pest control agent 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.

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 equation (Colby. SR; Calculating Synthetic Response and Antibiotic Responses of Herbide Combinations; Weeds 15, 20-22, 1967) according to a standard method.

[External parasite control agent]
The pyridine compound of the present invention or a salt thereof (hereinafter sometimes referred to as “the present compound”) is excellent in the control effect of ectoparasites that are harmful to humans and animals. 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.
Examples of ectoparasites include ticks, lice and fleas.
Examples of the host animal to be treated with the ectoparasite control agent of the present invention include pets such as dogs and cats; pets; livestock such as cattle, horses, pigs and sheep; poultry. 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;

[Prescription formulation]
Although the pharmaceutical formulation of the pest control agent of the present invention is shown slightly, the additives and addition ratios are not limited to these examples, and can be varied in a wide range. The parts in the formulation of the preparation indicate parts by weight. The formulation for agricultural and horticultural and paddy rice is shown below.

(Formulation 1: wettable powder)
Compound of the present invention 40 parts Diatomaceous earth 53 parts Higher alcohol sulfate 4 parts Alkyl naphthalene sulfonate 3 parts The above components were mixed uniformly and finely pulverized to obtain a wettable powder of 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 or more are uniformly mixed and finely pulverized, then granulated into granules having a diameter of 0.5 to 1.0 mm and active ingredient 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 or more is pulverized and mixed well, water is added and kneaded well, granulated and dried, and 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 or more are mixed and wet milled until the particle size is 3 microns or less, A suspension with 10% active ingredient is obtained.

The formulation of 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 After balance preparation, filter sterilize with a sterilization filter.

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

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

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

Next, the present invention will be described more specifically by showing examples. However, the present invention is not limited by the following examples.

Example 1 Synthesis of 3-chloro-2-[(3-ethoxy-4-pyridyl) methoxy] -5- (trifluoromethyl) pyridine (Compound No. 1-5) (Step 1) (3-Fluoro- Synthesis of 4-pyridyl) methanol 20 g of 3-fluoropyridine was dissolved in 40 mL of tetrahydrofuran and cooled to −78 ° C. under a nitrogen atmosphere. At −78 ° C., 100 mL of a 2M tetrahydrofuran solution of lithium diisopropylamine was added dropwise. After completion of dropping, the mixture was stirred at −78 ° C. for 1 hour. Next, 26 g of N, N-dimethylformamide was added dropwise at −78 ° C. After completion of dropping, the mixture was stirred at −78 ° C. for 0.5 hour. Subsequently, the temperature was raised to 0 ° C., 40 mL of water and 9.2 g of sodium borohydride were added, and the mixture was stirred at 0 ° C. for 1 hour. Thereafter, the reaction solution was concentrated under reduced pressure. Subsequently, water was added to this and extracted with chloroform. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 18 g of the desired product as a white solid.
The ¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.81 (t, 1H), 4.82 (d, 2H), 7.48 (m, 1H), 8.38 (m, 2H).

(Step 2) Synthesis of 3-fluoro-4- (methoxymethoxymethyl) pyridine 15 g of (3-fluoro-4-pyridyl) methanol was dissolved in a mixed solvent of 30 mL of tetrohydrofuran and 80 mL of N, N-dimethylformamide. The solution was cooled to −5 ° C. under a nitrogen atmosphere. At −5 ° C., 11 g of potassium tertiary butoxide was added. Thereafter, 8 g of chloromethyl methyl ether was added dropwise. After completion of dropping, the mixture was stirred at −5 ° C. for 0.5 hour. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 8.9 g of the desired product as a pale yellow oily substance.
The ¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 3.40 (s, 3H), 4.69 (s, 2H), 4.74 (s, 2H), 7.43 (m, 1H), 8.41 (M, 2H).

(Step 3) Synthesis of 3-chloro-2-[(3-ethoxy-4-pyridyl) methoxy] -5- (trifluoromethyl) pyridine 12 mL of N, N-dimethylformamide and 55% sodium hydride in mineral oil 1.1 g of the dispersed mixture was suspended and cooled to 0 ° C. Ethanol 1.2g was dripped at 0 degreeC. After completion of dropping, the mixture was stirred at 0 ° C. for 0.5 hour. A solution prepared by dissolving 0.4 g of 3-fluoro-4- (methoxymethoxymethyl) pyridine in N, N-dimethylformamide was added dropwise at 0 ° C. After completion of dropping, the temperature was raised to 130 ° C. and stirred for 1 hour. The resulting solution was cooled to room temperature. Then, the solution was poured into ice water and extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. A crude product of 3-ethoxy-4- (methoxymethoxymethyl) pyridine was obtained.
The crude product of 3-ethoxy-4- (methoxymethoxymethyl) pyridine was dissolved in 50 mL of 2M hydrochloric acid and stirred at 60 ° C. for 1 hour. The solution was cooled to room temperature. Thereafter, it was washed with chloroform. The resulting aqueous phase was neutralized by adding potassium carbonate. It was extracted with chloroform. The obtained organic phase was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. 0.28 g of a crude product of (3-ethoxy-4-pyridyl) methanol was obtained.
In 13 mL of dioxane, 0.28 g of a crude product of (3-ethoxy-4-pyridyl) methanol was dissolved. To this, 0.22 g of potassium tertiary butoxide and 0.47 g of 2,3-dichloro-5- (trifluoromethyl) pyridine were added at room temperature, and the mixture was heated to 60 ° C. and stirred for 5 hours. The solution was cooled to room temperature. Then, water was added and extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.34 g of the desired product as a pale yellow solid.
The melting point and ¹ H-NMR of the obtained target product are shown below.
Melting point 48-52 ° C
¹ H-NMR (400 MHz, CDCl ₃ ): δ 1.45 (t, 3H), 4.20 (q, 3H), 5.56 (s, 2H), 7.41 (m, 1H), 7.89 (M, 1H), 8.25 (m, 2H), 8.33 (m, 1H).

[Example 2]
Synthesis of 3-chloro-2-[(3-chloro-5-methylsulfanyl-4-pyridyl) methoxy] -5- (trifluoromethyl) pyridine (Compound No. 1-17) (Step 1) 3-chloro-5 Synthesis of methylsulfanyl-pyridine 1.0 g of 3,5-dichloropyridine was dissolved in 15 mL of N, N-dimethylformamide. Under a nitrogen atmosphere, 0.52 g of sodium methanethiolate was added to this solution and stirred at room temperature for 5 hours. Water was added to this solution and extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.87 g of the desired product as a colorless oily substance.
The ¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.50 (s, 3H), 7.50 (t, 1H), 8.30 (d, 1H), 8.34 (d, 1H).

(Step 2) Synthesis of 3-chloro-5-methylsulfanyl-4-pyridine) methanol 1.0 g of 3-chloro-5-methylsulfanyl-pyridine was dissolved in 24 mL of diethyl ether. The solution was cooled to −78 ° C. under a nitrogen atmosphere. At −78 ° C., 4.2 mL of a 1.65 Mn-hexane solution of n-butyllithium was added dropwise. After completion of dropping, the mixture was stirred at −78 ° C. for 1 hour. Next, 0.70 mL of methyl formate was added dropwise at −78 ° C. After completion of dropping, the mixture was stirred at −78 ° C. for 0.5 hour. Then, it heated up to room temperature and stirred for 1 hour. Subsequently, 1.2 mL of water and 0.26 g of sodium borohydride were added at room temperature, and the mixture was stirred at room temperature for 1 hour. The resulting solution was concentrated under reduced pressure. Water was added to this and extracted with chloroform. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.15 g of the desired product as a pale yellow solid.
The ¹ H-NMR of the obtained target product is shown below.
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.37 (d, 1H), 2.56 (s, 3H), 4.92 (d, 2H), 8.39 (s, 1H), 8 .40 (s, 1H).

(Step 3) Synthesis of 3-chloro-2-[(3-chloro-5-methylsulfanyl-4-pyridyl) methoxy] -5- (trifluoromethyl) pyridine into 2 mL of dioxane (3-chloro-5-methylsulfanyl 0.15 g of -4-pyridyl) methanol was dissolved. To this solution, 0.1 g of potassium tertiary butoxide and 0.19 g of 2,3-dichloro-5- (trifluoromethyl) pyridine were added at room temperature, and the mixture was stirred at room temperature for 3 hours. Water was added to the solution and extracted with ethyl acetate. The obtained organic phase was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain the desired product (0.13 g) as a pale yellow solid.
The melting point and ¹ H-NMR of the obtained target product are shown below.
Melting point 82-85 ° C
¹ H-NMR (400 MHz, CDCl ₃ ): δ 2.53 (s, 3H), 5.67 (s, 2H), 7.86 (m, 1H), 8.37 (m, 1H), 8.46 (M, 2H).

Tables 1 and 2 show pyridine compounds produced according to the above-described method. 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. In Table 1, R ¹ , (X ¹ ) _m , Z, A, R ² , and (X ² ) _n are those in the compound represented by the formula (Ia). * 1 to * 6 in Table 1 each represent a group in Appendix 1. R ¹ , (X ¹ ) _m , Z, A, R ² , and (X ² ) _n in Table 2 are those in the compound represented by the formula (Ia ′). R ¹ , (X ¹ ) _m , Z, A, R ² , and (X ² ) _n in Table 3 are those in the compound represented by formula (Ib).

The physical properties of the compounds shown in Tables 1 to 3 were measured. The measurement results are shown below. The leftmost number corresponds to the compound number in the table.

1-1: Melting point 91-92 ° C
1-2: Melting point 55-57 ° C
1-3: Melting point 87-88 ° C
1-4: Melting point 95-97 ° C
1-5: Melting point 48-52 ° C.
1-6: Melting point 62-65 ° C.
1-7: Melting point 54-56 ° C.
1-8: Melting point 103-105 ° C.
1-9: Melting point 73-76 ° C.
1-10: Melting point 63-65 ° C.
1-11: Refractive index (22.1 ° C.) 1.5044
1-12: Melting point 148-150 ° C.
1-13: Refractive index (20.7 ° C.) 1.5442
1-14: Refractive index (21.7 ° C.) 1.50012
1-15: Refractive index (21.8 ° C.) 1.5126
1-16: Refractive index (18.9 ° C.) 1.5062
1-17: Melting point 82-85 ° C.
1-18: Refractive index (21.3 ° C.) 1.4968
1-19: Refractive index (22.1 ° C.) 1.4919
1-20: Melting point 72-75 ° C.

1-21: Melting point 81-82 ° C
1-22: Refractive index (21.8 ° C.) 1.51
1-23: Melting point 123-126 ° C.
1-24: Melting point 65-68 ° C.
1-25: 1H-NMR (400 MHz, CDCl3): δ 8.52 (d, 1H), 8.35 (s, 1H), 8.31 (s, 1H), 7.88 (s, 1H), 7 .55 (d, 1H), 5.50 (s, 2H), 3.47 (s, 3H), 3.40 (s, 3H).
1-26: Melting point 97-100 ° C
1-27: Refractive index (20.7 ° C) 1.5005
1-28: Refractive index (20.7 ° C) 1.5351
1-29: Melting point 63-65 ° C
1-30: melting point 88-92 ° C.
1-31: Melting point 48-50 ° C
1-32: Melting point 60-62 ° C
1-33: Refractive index (20.6 ° C) 1.5314
1-34: Refractive index (20 ° C) 1.531
1-35: 1H-NMR (400 MHz, CDCl3): δ 8.65 (m, 2H), 8.20 (m, 1H), 7.95-7.83 (m, 5H), 7.62-7. 53 (m, 4H), 5.48 (s, 2H).
1-36: Melting point 121-124 ° C (hydrochloride)
1-37: Melting point 126-131 ° C. (tetrafluoroborate salt)
1-38: Melting point: 39-41 ° C
1-39: Melting point 150-153 ° C
1-40: Melting point 51-53 ° C.

1-41: 1 H-NMR (400 MHz, CDCl3): δ 8.20 (m, 3H), 7.55 (m, 1H), 7.34 (m, 1H), 5.55 (s, 2H), 4 .11 (t, 2H), 1.78 (m, 2H), 1.47 (m, 2H), 0.96 (t, 3H).
1-42: Melting point 71-73 ° C
1-43: Melting point 118-120 ° C
1-44: Melting point 95-96 ° C
1-45: Melting point 92-94 ° C
1-46: Melting point 177-180 ° C
1-47: Melting point 200 ° C or higher 1-48: Melting point 99-101 ° C
1-49: Melting point 86-89 ° C
1-50: melting point 200 ° C. or higher 1-51: melting point 145-148 ° C.
1-52: Melting point 95-99 ° C.
1-53: Melting point 110-113 ° C.
1-54: melting point 200 ° C. or higher 1-55: melting point 118-123 ° C.
1-56: Melting point 66-69 ° C.
1-57: Melting point 146-149 ° C.
1-58: 1H-NMR (400 MHz, CDCl3): δ 8.63 (s, 1H), 8.60 (d, 1H), 8.27 (s, 1H), 7.87 (s, 1H), 7 .69 (d, 1H), 7.61 (s, 1H), 6.28 (d, 1H), 5.66 (s, 2H), 2.35 (s, 3H).
1-59: 1H-NMR (400 MHz, CDCl3): δ 8.71-8.69 (m, 2H), 8.25 (s, 1H), 7.87-7.86 (m, 2H), 7 .64 (d, 1H), 6.68 (d, 1H), 5.61 (s, 2H).
1-60: melting point 65-68 ° C.
1-61: melting point 131-135 ° C.
1-62: melting point 105-108 ° C.
1-63: Melting point 73-76 ° C.
1-64: Melting point 73-75 ° C.
1-65: Refractive index (20.5 ° C) 1.5511

1-66: Melting point 180-181 ° C. (hydrochloride)
1-67: Melting point 186-189 ° C.
1-68: Melting point 127-131 ° C.
1-69: melting point 128-130 ° C.
1-70: melting point 85-90 ° C.
1-71: melting point 88-93 ° C.
1-72: Melting point 90-95 ° C.
1-73: Melting point 123-126 ° C.
1-74: melting point 102-103 ° C.
1-75: melting point 132-134 ° C.
1-76: Melting point 56-59 ° C.
1-77: Melting point 81-84 ° C.
1-78: melting point 108-110 ° C.
1-79: Melting point 120-121 ° C
1-80: Melting point 88-90 ° C.
1-81: Melting point 81-84 ° C.
1-82: Melting point 91-94 ° C.
1-83: Melting point 154-158 ° C.
1-84: Melting point 168-170 ° C.
1-85: Refractive index (19.4 ° C.) 1.5269
1-86: Melting point 127-130 ° C.
1-87: melting point 136-140 ° C.
1-88: melting point 223-226 ° C.
1-89: melting point 63-65 ° C.
1-90: melting point 72-75 ° C.
1-91: Melting point 68-71 ° C.
1-92: Melting point 77-79 ° C.
1-93: Melting point 72-74 ° C.
1-94: Refractive index (20.6 ° C.) 1.5255
1-95: Melting point 73-75 ° C.
1-96: melting point 106-108 ° C.
1-97: Melting point 59-61 ° C.
1-98: melting point 132-134 ° C.
1-99: Melting point 68-70 ° C.
1-100: Melting point 88-90 ° C.
1-101: Melting point 122-124 ° C
1-102: Melting point 202-204 ° C
1-103: 1H-NMR (400 MHz, CDCl3: a9.35 (s, 1H), 8.85 (d, 1H), 8.35 (s, 1H), 7.91 (s, 1H), 7. 56 (d, 1H), 5.70 (d, 1H), 5.65 (d, 1H), 3.19 (s, 3H).
1-104: 1H-NMR (400 MHz, CDCl3: a9.25 (s, 1H), 8.95 (d, 1H), 8.27 (s, 1H), 7.94 (s, 1H), 7. 75 (d, 1H), 5.93 (d, 1H), 5.90 (d, 1H), 3.63 (s, 3H).
1-105: 1H-NMR (400 MHz, CDCl3: a 8.58 (d, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 7.89 (s, 1H), 7. 49 (d, 1H), 5.61 (s, 2H), 4.60 (s, 2H), 3.40 (s, 3H).

1-106: Melting point 53-55 ° C
1-107: melting point 132-134 ° C
1-108: 1H-NMR (400 MHz, CDCl3: a8.59 (s, 1H), 8.57 (s, 1H), 8.24 (d, 1H), 7.81 (s, 1H), 7. 81 (s, 1H), 7.73 (d, 1H), 6.48 (t, 1H), 5.65 (s, 2H).
1-109: Melting point: 84-88 ° C
1-110: 1H-NMR (400 MHz, CDCl3: a8.62 (s, 1H), 8.53 (s, 1H), 8.24 (m, 1H), 7.83 (d, 1H), 7. 76 (d, 1H), 7.73 (d, 1H), 6.46 (t, 1H), 5.54 (s, 2H), 2.59 (s, 3H).
1-111: Melting point 187-191 ° C
1-112: Melting point: 167-169 ° C.
1-113: Melting point 135-138 ° C
1-114: Melting point 74-76 ° C.
1-115: Refractive index (20.4 ° C.) 1.5254
1-116: Refractive index (20.5 ° C) 1.5439
1-117: Refractive index (20.6 ° C) 1.5537
1-118: Refractive index (20.6 ° C.) 1.4724
1-119: 1H-NMR (400 MHz, CDCl3: a8.82 (s, 1H), 8.64 (d, 1H), 8.59 (s, 1H), 8.32 (s, 1H), 7. 90 (s, 1H), 7.63 (d, 1H), 5.89 (s, 2H), 3.95 (m, 2H), 3.84 (m, 2H).
1-120: Melting point 87-89 ° C.
1-121: melting point 87-89 ° C.
1-122: melting point 65-67 ° C.
1-123: melting point 92-94 ° C.
1-124: melting point 138-143 ° C.
1-125: melting point 92-93 ° C.
1-126: Refractive index (22.5 ° C.) 1.5674
1-127: Refractive index (20.8 ° C) 1.5613
1-128: Refractive index (22.8 ° C.) 1.5707
1-129: Melting point 58-60 ° C
1-130: Melting point 50-52 ° C. (E form)
1-131: Melting point 92-93 ° C. (Z form)
1-132. Melting point: 84-86 ° C
1-133: Refractive index (22.4 ° C.) 1.5873
1-134: Refractive index (21.6 ° C.) 1.5754
1-135: Melting point 125-127 ° C
1-136: Melting point 126-128 ° C
1-137: Melting point 33-35 ° C
1-138: Refractive index (25 ° C.) 1.533
1-139: 1H-NMR (400 MHz, CDCl3): a8.83 (s, 1H), 8.57 (d, 1H), 8.33 (s, 1H), 7.90 (s, 1H), 7 .47 (d, 1H), 5.65 (s, 2H), 5.44 (q, 1H), 1.99 (d, 3H).
1-140: Refractive index (24.7 ° C.) 1.5459
1-141: melting point 104-106 ° C
1-142: Melting point 144-146 ° C
1-143: Refractive index (31.3 ° C.) 1.5452
1-144: Melting point 174-177 ° C
1-145: Melting point 188-192 ° C
1-146: Melting point: 40-42 ° C
1-147: Melting point 110-112 ° C
1-148: Melting point 66-68 ° C
1-149: Melting point: 106-109 ° C
1-150: melting point 59-60 ° C.
1-151: melting point 88-89 ° C.
1-152: 1 H-NMR (400 MHz, CDCl 3): a8.93 (s, 1H), 8.89 (s, 1H), 8.23 (s, 1H), 7.82-7.79 (m, 3H), 6.54 (t, 1H), 5.74 (s, 2H).
1-153: Melting point 90-92 ° C
1-154: Melting point 112-114 ° C
1-155: Melting point 58-60 ° C
1-156: Melting point 107-109 ° C
1-157: Melting point 155-157 ° C
1-161: melting point 94-96 ° C.
1-162: Refractive index (21.3 ° C.) 1.5442
1-163: melting point 170-172 ° C.
1-164: melting point 142-144 ° C.
1-165: Melting point 67-68 ° C
1-166: Refractive index (22.1 ° C.) 1.5642

1-200: melting point 102-104 ° C
1-201: Refractive index (20.6 ° C) 1.5659
1-202: Melting point 57-61 ° C
1-203: melting point 83-87 ° C
1-210: Refractive index (21.7 ° C.) 1.519
1-211: Refractive index (20.8 ° C.) 1.5079
1-212: Melting point 85-89 ° C

2-1 Melting point 106-109 ° C
2-2: Melting point 144-146 ° C
2-3: Refractive index (20.6 ° C) 1.6039
2-5: Melting point 53-55 ° C
2-6: 1H-NMR (400 MHz, CDCl3): δ 8.46 (m, 3H), 7.79 (m, 1H), 7.22 (m, 1H), 6.84 (m, 1H), 6.35 (m, 1H), 2.90-2.76 (m, 2H), 2.25-1.84 (m, 4H).

[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.

Test Example 1 Efficacy Test for Bean Aphids First, 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 containing 5% active ingredient. did.
An adult bean aphid was released on a cowpea that had developed its primary leaves. After 1 day, the 1st instar larvae were left behind and the adults were removed. The above emulsion was diluted with water to a compound concentration of 125 ppm. This diluted solution was sprayed on the cowpea. Thereafter, the cowpea was placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. And the life or death of the bean aphid was examined 4 days after spraying and the insecticidal rate was calculated | required.

Compound Nos. 1-1, 1-4, 1-5, 1-6, 1-7, 1-8, 1-11, 1-13, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-23, 1-24, 1-25, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1- 33, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-45, 1-48, 1-49, 1-56, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-66, 1-74, 1-75, 1-76, 1-77, 1-79, 1-80, 1- 81, 1-86, 1-87, 1-91, 1-92, 1-93, 1-94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-103, 1-104, 1-10 , 1-106, 1-107, 1-108, 1-115, 1-116, 1-120, 1-121, 1-122, 1-123, 1-124, 1-127, 1-128, 1 -129, 1-130, 1-133, 1-135, 1-136, 1-137, 1-138, 1-139, 1-140, 1-146, 1-148, 1-149, 1-150 1-151, 1-153, 1-154, 1-155, 1-156, 1-157, 1-162, 1-164, 1-165, 1-201, 1-202, 1-203, 1 The above tests were conducted on emulsions containing the compounds of −211, 1-212, 2-1, 2-2, and 2-3, respectively. All the compounds were 80% or more.

(Test Example 2) Efficacy test against brown planthopper The emulsion described in Test Example 1 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 and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. Then, after 6 days from the release of the insects, the survival of the brown planthopper was examined and the insecticidal rate was determined. As the brown planthopper, two types of (A) drug-sensitive lines and (B) drug-insensitive lines (lines collected in Kumamoto Prefecture in 2011 and kept indoors) were used.

Compound Nos. 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-14, 1-16, Emulsions containing compounds 1-17, 2-1, 2-2, and 2-3, respectively, were tested using (A) drug-sensitive lines. All compounds had an insecticidal rate of 80% or more.

Compound Nos. 1-5, 1-6, 1-7, 1-8, 1-13, 1-18, 1-20, 1-21, 1-26, 1-27, 1-28, 1-29, 1-30, 1-31, 1-32, 1-34, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-42, 1-48, 1- 49, 1-56, 1-60, 1-61, 1-62, 1-63, 1-64, 1-65, 1-70, 1-74, 1-75, 1-76, 1-78, 1-79, 1-80, 1-82, 1-85, 1-90, 1-96, 1-97, 1-100, 1-103, 1-106, 1-107, 1-108, 1- 115, 1-116, 1-117, 1-118, 1-119, 1-120, 1-121, 1-122, 1-123, 1-127, 1-135, 1-136, 1-140, 1-1 1, 1-145, 1-146, 1-148, 1-151, 1-152, 1-153, 1-156, 1-157, 1-202, 1-203, and 2-1, respectively. The emulsion contained was tested using (B) a drug-insensitive line. All compounds had an insecticidal rate of 80% or more.

Emulsions containing imidacloprid (125 ppm) were tested using (A) drug sensitive lines. The insecticidal rate was 100%.
Emulsions containing imidacloprid (125 ppm) were tested using (B) drug-insensitive lines. The insecticidal rate was 50%.

Emulsions containing buprofezin (125 ppm) were tested using (A) drug sensitive lines. The insecticidal rate was 100%.
Emulsions containing buprofezin (125 ppm) were tested using (B) drug-insensitive lines. The insecticidal rate was 70%.

Test Example 3 Efficacy Test for Tobacco Whitefly The emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm. The diluted solution was sprayed on tomato cut leaves and then air-dried. In the flask, the leaf was fixed using absorbent cotton so that the leaf surface faced upward. Seven pairs of tobacco whitefly type B adults were released into this flask, parasitized on tomato cut leaves, and placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. Two days after the release, the larvae that were delivered were left and the adults were removed. The number of surviving larvae was examined 12 days after the release. Here, the efficacy of the compound was evaluated by the next generation control rate shown in the following formula 1.
Next generation control rate = 100 − {(T × Ca) / (Ta × C)} × 100
Ta: Number of parasites immediately after release in the spray treatment section T: Number of parasites 12 days after release in the spray treatment section Ca: Number of parasites immediately after release in the untreated section C: 12 days after release in the untreated section Number of parasites

Compound Nos. 1-1, 1-4, 1-6, 1-7, 1-8, 1-9, 1-11, 1-13, 1-17, 1-18, 1-20, 1-21, 1-23, 1-26, 1-27, 1-29, 1-30, 1-31, 1-38, 1-39, 1-58, 1-60, 1-64, 1-66, 1- 74, 1-76, 1-78, 1-79, 1-81, 1-86, 1-91, 1-93, 1-95, 1-96, 1-97, 1-100, 1-103, The above tests were conducted on emulsions containing the compounds 1-104, 1-108, 1-122, 1-202, 2-2, and 2-3, respectively. All the compounds had a next-generation control rate of 80% or more.

(Test Example 4) Efficacy test against pearl millet The emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm. Corn leaves were immersed in this diluted solution for 30 seconds and then air-dried. The corn leaves were placed in a petri dish with filter paper, and 5 second instar larvae were released. Thereafter, a glass lid was placed and placed in a constant temperature room at 25 ° C. and 60% humidity, and after 6 days, life and death were examined to determine the insecticidal rate.

The above tests were conducted on emulsions containing the compounds Nos. 1-23, 1-39, and 1-137, respectively. All compounds showed an insecticidal rate of 80% or more.

(Test Example 5) Efficacy test against spider mite of Kanzawa Ten adult females of spider mite from Okayama were inoculated on the primary leaves 7 to 10 days after germination of green beans seeded in a three-size pot. Next, an emulsion described in (Test Example 1) was prepared. The emulsion was diluted with water to a compound concentration of 125 ppm, and the diluted solution was sprayed on the kidney beans. The green beans were placed in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 65%. The life and death of adults were investigated after 3 days from the spraying. Furthermore, it was investigated whether the delivered eggs could develop to adults after 14 days from spraying.

The above test was carried out on emulsions containing 125 ppm each of compounds Nos. 1-26, 1-38, 1-60, 1-101, 1-118, 1-124, and 1-125. All compounds had an insecticidal rate after 3 days or an insecticidal rate after 14 days of 90% or more.

Claims (4)

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

   

   [In the formula (I),
   R ¹ represents a C1-6 haloalkyl group or a C1-6 alkoxy C1-6 haloalkyl 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, unsubstituted or Substituted C3-8 cycloalkyl group, hydroxyl group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted or substituted C1 -6 alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or A substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, an unsubstituted one Or a 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group having a substituent.
   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.
   R 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, unsubstituted or Having a substituted C3-8 cycloalkyl group, an unsubstituted or substituted C4-8 cycloalkenyl group, a hydroxyl group, an unsubstituted or substituted C1-10 alkoxy group, an unsubstituted or substituted group C2-6 alkenyloxy group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C1-7 acyl group, carboxyl group, unsubstituted or substituted C1-6 Alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted aminocarbonyl Group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C6-10 arylthio group, unsubstituted or substituted C1-6 alkylsulfinyl group, unsubstituted or substituted Group having C6-10 arylsulfinyl group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted or substituted C1-7 acyloxy group, unsubstituted or substituted C1-6 Alkoxycarbonyloxy group, substituted aminocarbonyloxy group, substituted amino (thiocarbonyl) oxy group, unsubstituted or substituted C1-6 alkylsulfonyloxy group, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted C6-1 An aryloxy group, an unsubstituted or substituted 3- to 6-membered heterocyclic group, an unsubstituted or substituted imino C1-6 alkyl group, an unsubstituted or substituted C1-6 alkylideneaminooxy group An unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfinimidoyl group, an unsubstituted or substituted N-cyano-S- (C1-6 alkyl) sulfonimidoyl group , A halogeno group, a cyano group, or a nitro group.
   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, unsubstituted or A substituted C3-8 cycloalkyl group, an oxo group, a hydroxyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group A C1-6 alkoxycarbonyl group having an unsubstituted or substituted amino group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an A substituted or substituted C1-6 alkylsulfonyl group, an unsubstituted or substituted C6-10 aryl group, An unsubstituted or substituted 3- to 6-membered heterocyclic group, a halogeno group, a cyano group, or a nitro group is shown.
   n represents the number of X ² and is an integer from 0 to 3. When n is 2 or more, X ² may be the same as or different from each other.
   Z represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a group represented by NR ³ .
   R ³ represents a hydrogen atom, 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 substituted or substituted C3-8 cycloalkyl group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted group; And a C1-6 alkylsulfonyl group having an unsubstituted or substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclic group, or a cyano group.
   A represents an unsubstituted or substituted C1-6 alkylene group.
   Here, R ² and A may be connected to each other to form a ring together with the carbon atom to which R ² and A are bonded. ]
2. A pest control agent comprising at least one selected from the group consisting of the pyridine compound according to claim 1 and a salt thereof as an active ingredient.
3. An insecticide or acaricide containing, as an active ingredient, at least one selected from the group consisting of the pyridine compound according to claim 1 and a salt thereof.
4. An ectoparasite control agent comprising as an active ingredient at least one selected from the group consisting of the pyridine compound according to claim 1 and a salt thereof.