WO2014115834A1

WO2014115834A1 - Azolyl oxime compound or salt thereof, pest-control agent, insecticide or acaricide, disinfectant, and external parasite control agent

Info

Publication number: WO2014115834A1
Application number: PCT/JP2014/051486
Authority: WO
Inventors: 衆一伊藤; 純司一法師; 睦大天野; 岩田　淳; 伸哉幸堀; 里枝坂本
Original assignee: 日本曹達株式会社
Priority date: 2013-01-28
Filing date: 2014-01-24
Publication date: 2014-07-31
Also published as: JP2014159413A

Abstract

An azolyl oxime compound expressed by formula (I) or a salt thereof. In formula (I), Het represents a six member heteroaryl ring containing 2 to 3 nitrogen atoms as ring structural atoms. X¹ is a substitution group on the Het, and represents a C1-6 alkyl group which may be unsubstituted or may have a substitution group, or a C1-6 alkoxy group which may be unsubstituted or may have a substitution group, or the like. m indicates the number of X¹ groups, and is an integer from 0 to 3. A represents a carbon atom or a nitrogen atom. X² represents a halogen group or a C1-6 alkyl group which may be unsubstituted or may have a substitution group, or the like. n indicates the number of X² groups, and is an integer from 0 to 3. R¹ represents a C1-6 alkyl group which may be unsubstituted or may have a substitution group, or the like.

Description

Azolyl oxime compounds or salts thereof, pest control agents, insecticides or acaricides, fungicides, and ectoparasite control agents

The present invention relates to azolyl oxime compounds, pest control agents, insecticides or acaricides, fungicides, and ectoparasite control agents. More specifically, the present invention relates to an azolyloxime compound or a salt thereof, which has excellent insecticidal activity and / or acaricidal activity, is excellent in safety, and can be advantageously synthesized industrially, and harmful substances containing this as an active ingredient. The present invention relates to biocontrol agents, insecticides or acaricides, fungicides, and ectoparasite control agents.
This application claims priority based on Japanese Patent Application No. 2013-012989 filed in Japan on January 28, 2013, the contents of which are incorporated herein by reference.

As an azolyl oxime compound, for example, Patent Document 1 discloses an azolyl oxime compound having naphthyl or pyridyl and triazolyl or imidazolyl in the molecular structure. Patent Document 1 states that some of the compounds had an insecticidal effect against leafhopper, leafhopper, and diamondback moth. However, other compounds are merely described as potential insecticides. Patent Document 2 discloses a pyridine derivative. An azolyl oxime compound is disclosed as one of the pyridine derivatives. Patent Document 2 states that some of the compounds had an insecticidal effect against peach aphid, brown planthopper, silver leaf whitefly, and the like. However, other compounds are merely described as potential insecticides. “Azolyl” is a 5-membered saturated or unsaturated heterocyclyl group having two or more hetero atoms selected from the group consisting of a nitrogen atom, a sulfur atom and an oxygen atom as ring member atoms, and at least one of the hetero atoms. One is a nitrogen atom. Specific examples include triazolyl and imidazolyl.

Japanese Patent Laid-Open No. 03-68559 JP 2010-138166 A

An object of the present invention is to provide an azolyl oxime compound or a salt thereof, which is excellent in pest control activity, in particular, insecticidal activity and / or acaricidal activity, is excellent in safety, and can be synthesized advantageously industrially, and 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 bactericidal agent containing this as an active ingredient, and an ectoparasite control agent.

As a result of intensive studies to solve the above problems, the present inventors have found that an azolyloxime compound having a specific structure such as a diazine ring or a triazine ring or a salt thereof has excellent insecticidal activity and / or acaricidal activity, It was also found that it has good characteristics and high safety and can be used as an active ingredient of a pest control agent. Furthermore, it discovered that it could utilize as an active ingredient of a disinfectant and an ectoparasite control agent. The present invention has been completed based on this finding.

That is, the present invention includes the following.
[1] An azolyl oxime compound represented by the formula (I) or a salt thereof.

In the formula (I), Het represents a 6-membered heteroaryl ring containing 2 to 3 nitrogen atoms as constituent atoms of the ring.
X ¹ is a substituent on Het, which 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, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy Group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C3-8 cycloalkyloxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted Or a substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, unsubstituted Or a substituted amino 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, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl group, unsubstituted or substituted C6-10 aryloxy group, halogeno A 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.
A represents a carbon atom or a nitrogen atom.
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, a hydroxy 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, an unsubstituted or substituted amino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl group, Unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl Shows a halogeno group, a cyano group or a nitro group.
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.
R 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 A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclyl group is shown.
In the formula (I), a bond represented by crossed solid lines represents a double bond having stereoisomerism.

[2] The azolyl oxime compound or a salt thereof according to [1], wherein m is an integer of any one of 1, 2, or 3.
[3] The azolyloxime compound or a salt thereof according to [1], wherein the formula (I) is represented by the formula (II).

In the formula (II), X ¹¹ represents 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, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted amino group, unsubstituted or substituted A C1-6 alkylthio group having a group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group .
m1 represents the number of X ¹¹ and is an integer from 0 to 2. When m1 is 2 or more, X ¹¹ may be the same as or different from each other.
The bonds represented by X ¹ , A, X ² , n, R ¹ and the crossed solid line are as described above.
[4] An azolyl oxime compound represented by the formula (III) or a salt thereof.

In formula (III), X ¹ , X ¹¹ , m 1, A, X ² , n, R ¹ , and the bond represented by the crossed solid line are as described above.

[5] A pest control agent comprising as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
[6] An insecticide or acaricide containing as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
[7] A bactericide containing as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] and a salt thereof.
[8] An ectoparasite control agent comprising as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of [1] to [4] above and a salt thereof.

The azolyloxime 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, plant diseases can be effectively controlled. Furthermore, ectoparasites that harm human livestock can be effectively controlled.

Hereinafter, preferred examples of the present invention will be described, but the present invention is not limited to these examples. Additions, omissions, substitutions, and other modifications can be made without departing from the spirit of the present invention.
The azolyloxime compound of the present invention is a compound represented by the 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 (also known as allyl group), 1-butenyl group, 2-butenyl group, 3-butenyl group, 1-methyl-2-propenyl group, 2-methyl-2-propenyl group A C2-6 alkenyl group such as a group;
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 cycloheptyl group, a cyclooctyl 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 C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
3-6 membered heterocyclyl group;
A 3-6 membered heterocyclyl C1-6 alkyl group;
A C1-7 acyl group such as a formyl group, an acetyl group, a propionyl group, a benzoyl group, a cyclohexylcarbonyl group;

A hydroxy 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 1-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;

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;
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 alkylamino group such as a methylamino group, a dimethylamino group, a diethylamino group;
C6-10 arylamino groups such as anilino group and naphthylamino group;
A C6-10 aryl C1-6 alkylamino 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;
A C1-6 alkyl group substituted with an imino group 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 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 C6-10 aryl C1-6 alkylthio 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;
A C6-10 aryl C1-6 alkylsulfinyl group such as a benzylsulfinyl group, 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 C6-10 aryl C1-6 alkylsulfonyl 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;

A tri-C1-6 alkyl-substituted silyl group such as a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group;
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 addition, the “3- to 6-membered heterocyclyl 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 heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, thiazolidinyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, and dioxanyl group. .

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.

[Het]
Het represents a 6-membered heteroaryl ring containing 2 to 3 nitrogen atoms as constituent atoms of the ring. Het is preferably a pyrimidine ring.

[X ^1, m]
X ¹ is a substituent on Het, which 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, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy Group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C3-8 cycloalkyloxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted Or a substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, unsubstituted Or a substituted amino 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, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl group, unsubstituted or substituted C6-10 aryloxy group, halogeno A 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.
In the present invention, m is preferably an integer of 1, 2, or 3.

The “C1-6 alkyl group” for X ¹ may be linear or branched. 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, 3,3-dimethylbutyl group and the like.

In the “C1-6 alkoxy group having a substituent”, examples of the substituent include a halogeno group, a C3-8 cycloalkyl group, a hydroxy group, a C1-6 alkoxy group, a C6-10 aryl group, a C1-7 acyl group, a C1 Up to 6 alkoxycarbonyl groups.

Specific examples of the “C1-6 alkyl group having a substituent” include
Fluoromethyl group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, 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, perfluorohexyl group, perchlorohexyl group, 2,4,6-trichlorohexyl group, perfluoropropyl group, perfluorobutyl group, perfluoropentyl group, 3,3,4,4,5,5,5 -C1 ~ such as heptafluoropentyl group, 2,2,3,3,4,4,5,5,5-nonafluoropentyl group Haloalkyl groups;
C3-8 cycloalkyl C1-6 alkyl groups such as cyclopropylmethyl group, 2-cyclopropylethyl group, cyclopentylmethyl group, 2-cyclohexylethyl group, 2-cyclooctylethyl group;

Hydroxy C1-6 alkyl groups such as hydroxymethyl group, 2-hydroxyethyl group;
Methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy-n-propyl group, ethoxymethyl group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t A C1-6 alkoxy C1-6 alkyl group such as a butoxyethyl group;
A C6-10 aryl C1-6 alkyl group such as a benzyl group or a phenethyl group;
C1-7 acyl C1-6 alkyl group such as formylmethyl group, acetylmethyl group, propionylmethyl 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;
Etc.

Examples of the “C2-6 alkenyl group” for X ¹ include a 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, 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.

Examples of the “C2-6 alkynyl group” in X ¹ include ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentynyl group, 1-hexynyl Group, 1,1-dimethyl-2-butynyl group and the like.
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. Etc.

Examples of the “C3-8 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 “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, 3,3-dimethylbutoxy group, isopentyloxy group, neopentyloxy group, 2,3,3-trimethylbutoxy group, (4,4- And dimethylpentan-2-yl) oxy group.

In the “substituted C1-6 alkoxy group”, examples of the substituent include a halogeno group, a C3-8 cycloalkyl group, a hydroxy group, a C1-6 alkoxy group, a C1-6 haloalkoxy group, a C6-10 aryl group, 3-6 heterocyclyl group, C1-6 alkoxycarbonyl group, C1-6 alkyl substituted amino group, C1-6 alkylthio group, C1-6 alkylsulfinyl group, C1-6 alkylsulfonyl group, cyano group, C1-6 alkyl substituted silyl Groups and the like.

Specific 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, 2,2,3,3-tetrafluoropropoxy group, 2,2,3,3,3-pentafluoropropoxy group, 1,1, 2,3,3,3-hexafluoropropoxy group, 4,4,4-trifluorobutoxy group, 2,2,3,4,4,4-hexafluorobutoxy group, 2,2,3,3,4 , 4-Hexafluorobutoxy group, 2,2,3,3,4,4,4-heptafluorobutoxy group, 3,4,4,4-tetrafluoro-3- (trifluoromethyl ) Butoxy group, (5,5,5-trifluoropentyl) oxy group, (4,4,5,5,5-pentafluoropentyl) oxy group, (2,2,3,3,4,4,5) , 5-octafluoropentyl) oxy group, (2,2,3,3,4,4,5,5,5-nonafluoropentyl) oxy group, (2,2,3,3,4,4,5 , 5,6,6,6-undecafluorohexyl) oxy group and other C1-6 haloalkoxy groups;

C3-8 cycloalkyl C1-6 alkoxy groups such as cyclopropylmethoxy group, 2-cyclopropylethoxy group, cyclopentylmethoxy group, cyclohexylmethoxy group, 2-cyclohexylethoxy group; (2,2-difluorocyclopropyl) methoxy group, etc. A C3-8 cycloalkyl C1-6 alkoxy group having a halogeno group as a substituent; a C3-8 cycloalkyl C1-6 having a C1-6 alkyl group as a substituent, such as a (2-methylcyclopropyl) methoxy group An alkoxy group;

Hydroxy C1-6 alkoxy groups such as 3-hydroxy-3-methylbutoxy group; C1-6 alkoxy C1 such as 2-ethoxyethoxy group, 3-methoxy-3-methylbutoxy group, 2- (t-butoxy) ethoxy group -6 alkoxy group; C1-6 haloalkoxy C1-6 alkoxy group such as trifluoromethoxymethoxy group and trifluoromethoxyethoxy group;

A C6-10 aryl C1-6 alkoxy group such as benzyloxy group, phenoxy group, 3-phenylpropoxy group;
(4-methylbenzyl) oxy group, (4-methoxybenzyl) oxy group, (4-trifluorobenzyl) oxy group, (4-fluorobenzyl) oxy group, etc. A C6-10 aryl C1-6 alkoxy group having a 6 alkoxy group, a C1-6 haloalkyl group, or a halogeno group;
(Oxetane-3-yl) methoxy group, (tetrahydrofuran-2-yl) methoxy group, (pyridin-2-yl) methoxy group, (pyridin-3-yl) methoxy group, 2- (pyridin-2-yl) ethoxy Groups, 3- to 6-membered heterocyclyl C1-6 alkoxy groups such as 3- (pyridin-2-yl) propoxy group; (3-methyloxetan-3-yl) methoxy group, (6-chloropyridin-3-yl) methoxy Groups such as 2- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) ethoxy group, 3- (3-chloro-5- (trifluoromethyl) pyridin-2-yl) propoxy group, 3- to 6-membered heterocyclyl C1-6 alkoxy having a C1-6 alkyl group, C1-6 alkoxy group, C1-6 haloalkyl group, or halogeno group as a substituent ;

C1-6 alkoxycarbonyl such as 2- (ethoxycarbonyl) ethoxy group C1-6 alkoxy group; C1-6 such as (1- (dimethylamino) propan-2-yl) oxy group, 2- (dimethylamino) ethoxy group Alkyl substituted amino C1-6 alkoxy group; C1-6 alkylthio C1-6 alkoxy group such as 3- (methylthio) propoxy group; C1-6 alkylsulfinyl C1-6 alkoxy group such as 3- (methylsulfinyl) propoxy group; 3 A C1-6 alkylsulfonyl C1-6 alkoxy group such as a-(methylsulfonyl) propoxy group; a cyano C1-6 alkoxy group such as a 2-cyano-2-methylpropoxy group; a triC1-6 such as a 3- (trimethylsilyl) propoxy group 6 alkyl substituted silyl C1-6 alkoxy groups; It is.

Examples of the “C2-6 alkenyloxy group” in X ¹ include a vinyloxy group, 1-propenyloxy group, 2-propenyloxy group (allyloxy group), (3-methylbut-2-en-1-yl) oxy group and the like. Can be mentioned.
Examples of the “substituted C2-6 alkenyloxy group” include (2,3,3-trifluoroallyl) oxy group, (3,4,4-trifluorobut-3-en-1-yl) oxy group C2-6 haloalkenyloxy groups such as; C6-C10 aryl C2-6 alkenyloxy groups such as (3-phenylallyl) oxy group; and the like.

Examples of the “C2-6 alkynyloxy group” for X ¹ include ethynyloxy group, prop-2-yn-1-yloxy group, but-2-yn-1-yloxy group and the like.
Examples of the “substituted C2-6 alkynyloxy group” include C2 such as 4,4-dichloro-1-butynyloxy group, 4-fluoro-1-pentynyloxy group, 5-bromo-2-pentynyloxy group, etc. To 6 haloalkynyloxy groups; C6-C10 aryl C2-6 alkynyloxy groups such as (3-phenylprop-2-yn-1-yl) oxy group;

Examples of the “C3-8 cycloalkyloxy group” for X ¹ include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, and the like.
Examples of the “substituted C3-8 cycloalkyloxy group” include C3-8 halocycloalkyloxy groups such as (4,4-difluorocyclohexyl) oxy group.

Examples of the “C1-7 acyl group” in X ¹ include formyl group, acetyl group, propionyl group, benzoyl group and the like.
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” for X ¹ include a methoxycarbonyl group, an ethoxycarbonyl group, an n-propoxycarbonyl group, an i-propoxycarbonyl group, and the like.
As the “C1-6 alkoxycarbonyl group having a substituent”,
Cyclopropylmethoxycarbonyl group, cyclobutylmethoxycarbonyl group, cyclopentylmethoxycarbonyl group, cyclohexylmethoxycarbonyl group, 2-methylcyclopropylmethoxycarbonyl group, 2,3-dimethylcyclopropylmethoxycarbonyl group, 2-chlorocyclopropylmethoxycarbonyl group C3-8 cycloalkyl C1-6 alkoxycarbonyl groups such as 2-cyclopropylethoxycarbonyl group; fluoromethoxycarbonyl group, chloromethoxycarbonyl group, bromomethoxycarbonyl group, difluoromethoxycarbonyl group, dichloromethoxycarbonyl group, dibromomethoxycarbonyl Group, trifluoromethoxycarbonyl group, trichloromethoxycarbonyl group, tribromomethoxycarbonyl group, 2,2 , 2-trifluoroethoxycarbonyl group, 2,2,2-trichloroethoxycarbonyl group, pentafluoroethoxycarbonyl group, 4-fluorobutoxycarbonyl group, 3,3,3-trifluoropropoxycarbonyl group, 2,2,2 A C1-6 haloalkoxycarbonyl group such as a trifluoro-1-trifluoromethylethoxycarbonyl group or a perfluorohexyloxycarbonyl group;

Examples of the “C1-6 alkylcarbamoyl group” for X ¹ include a methylcarbamoyl group, an ethylcarbamoyl group, and the like.
Examples of the “substituted C1-6 alkylcarbamoyl group” include C1-6 haloalkylcarbamoyl groups such as a (2,2,2-trifluoroethyl) carbamoyl group.

As the “amino group having a substituent” for X ¹ , a C1-6 alkyl-substituted amino group such as a methylamino group, a dimethylamino group, a diethylamino group, an isopentylamino group, an isopentyl (methyl) amino group; , 3,3,4,4,4-heptafluorobutyl) amino group and the like, and the like.

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, isopentylthio group and the like. Can be mentioned.

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

Examples of the “C1-6 alkylsulfonyl group” for X ¹ include a methylsulfonyl group, an ethylsulfonyl group, a t-butylsulfonyl group, an isopentylsulfonyl 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 heterocyclyl 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 ring constituent atoms. The heterocyclyl group may be monocyclic or polycyclic. In the polycyclic heterocyclyl group, when at least one ring is heterocyclyl, the remaining ring may be a saturated alicyclic ring, an unsaturated alicyclic ring, or an aromatic ring. Examples of the “3- to 6-membered heterocyclyl group” include a 3- to 6-membered saturated heterocyclyl group, a 5- to 6-membered heteroaryl group, and a 5- to 6-membered partially unsaturated heterocyclyl group.

Examples of the 3- to 6-membered saturated heterocyclyl group include aziridinyl group, oxiranyl group, azetidinyl group, oxetanyl group, pyrrolidinyl group, tetrahydrofuranyl group, piperidyl group, piperazinyl group, morpholinyl group, dioxolanyl group, dioxanyl group and the like.

Examples of the partially unsaturated 5-membered heterocyclyl group include pyrrolinyl group, imidazolinyl group (dihydroimidazolinyl 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.

Substituents on “C6-10 aryl group” and “3-6 membered heterocyclyl group” include C1-6 alkyl group, hydroxy group, C1-6 alkoxy group, halogeno group, cyano group, nitro group, C1-6 And a haloalkyl group.

Examples of the “C6-10 aryloxy group” for X ¹ include a phenoxy group and a 1-naphthoxy group.
Examples of the substituent on the “C6-10 aryloxy group” include a C1-6 alkyl group, a hydroxy group, a C1-6 alkoxy group, a halogeno group, a cyano group, a nitro group, and a C1-6 haloalkyl group.

Examples of the “halogeno group” for X ¹ include a fluoro group, a chloro group, a bromo group, and an iodo 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, an unsubstituted Or a substituted C3-8 cycloalkyl group, a hydroxy group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-7 acyl group, an unsubstituted or substituted group C1-6 alkoxycarbonyl group, unsubstituted or substituted amino group, unsubstituted or substituted C1-6 alkylthio group, unsubstituted or substituted C1-6 alkylsulfonyl group, unsubstituted Or a substituted C6-10 aryl group, an unsubstituted or substituted 3-6 membered heterocyclyl group, a halo Amino group is preferably a cyano group or a nitro group.

X ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C2-6 alkenyloxy group, unsubstituted Or a substituted C2-6 alkynyloxy group, an unsubstituted or substituted C3-8 cycloalkyloxy group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, an unsubstituted or substituted group An unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted 3-6 membered heterocyclyl group, or an unsubstituted or substituted C6-10 aryloxy group More preferably.

X ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted C1-6 alkylthio group, or an unsubstituted group. Or a 3- to 6-membered saturated heterocyclyl group having a substituent.
In the “C1-6 alkyl group having a substituent”, the substituent is preferably a halogeno group or a C3-8 cycloalkyl group.
In the “substituted C1-6 alkoxy group”, examples of the substituent include a C1-6 alkyl group, a hydroxy group, a C1-6 alkoxy group, a C1-6 alkylthio group, a C6-10 aryl group, and a 3-6 membered heterocyclyl. Group, C1-6 alkyl 3-6 membered heterocyclyl group, halogeno group, cyano group, C3-8 cycloalkyl group, halo C3-8 cycloalkyl group, C1-6 alkyl C3-8 cycloalkyl group and the like are preferable.
In the “C1-6 alkylcarbamoyl group having a substituent”, the substituent is preferably a halogeno group or the like.
In the “amino group having a substituent”, the substituent is preferably a C1-6 alkyl group and the like.
In the “3- to 6-membered saturated heterocyclyl group having a substituent”, the substituent is preferably a C1-6 alkyl group, a halogeno group, a cyano group, a C1-6 haloalkyl group, or the like.
Specifically, as the ^{X 1,} C1 ~ 6 alkyl group, C1 ~ 6 haloalkyl group, C1 ~ 6 alkoxy group, C1 ~ 6 haloalkoxy group, C3 ~ 8 cycloalkyl C1 ~ 6 alkoxy group, C1 ~ 6 alkylthio group, Or, it is preferably a 3- to 6-membered saturated heterocyclyl group.

[A]
A represents a carbon atom or a nitrogen atom. A is preferably a nitrogen atom.

[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, a hydroxy 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, an unsubstituted or substituted amino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl group, Unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl Shows a halogeno group, a cyano group or a nitro group.
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.

“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 ”,“ C1-6 alkylthio group ”,“ C1-6 alkylsulfonyl group ”,“ C6-10 aryl group ”,“ 3-6 membered heterocyclyl group ”, Examples of the “halogeno group” and the group having a substituent in these groups are the same as those exemplified for X ¹ above.

[R ¹ ]
R 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 A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclyl group is shown.

“C1-6 alkyl group”, “C2-6 alkenyl group”, “C2-6 alkynyl group”, “C3-8 cycloalkyl group”, “C6-10 aryl group”, and “3-6 members” in R ¹ Examples of the “heterocyclyl group” and the group having a substituent in these groups include the same groups as those exemplified above for X ¹ .
R ¹ is an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, or an unsubstituted or substituted C2-6 alkynyl group. Is preferred.
In the “C1-6 alkyl group having a substituent”, the substituent is preferably a C3-8 cycloalkyl group or a halogeno group.

In the formula (I), a bond represented by crossed solid lines represents a double bond having stereoisomerism (undefined double stereo bond).
By this double bond, the azolyl oxime compound of the present invention or a salt thereof has an E isomer or a Z isomer, or an E isomer, which is a stereoisomer of a double bond derived from the oxime structure in the formula (I). And a mixture of Z isomers.

The azolyl oxime compound of the present invention is preferably an azolyl oxime compound represented by formula (II) (hereinafter sometimes referred to as compound (II)).

In formula (II), X ¹ , A, X ² , n, R ¹ and the bond represented by the crossed solid line are as described above.

^[X 11, m1]
In the formula (II), X ¹¹ represents 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, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted amino group, unsubstituted or substituted A C1-6 alkylthio group having a group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group .
m1 represents the number of X ¹¹ and is an integer from 0 to 2. When m1 is 2 or more, X ¹¹ may be the same as or different from each other.

"C1 ~ 6 alkyl group" in X ^11, "C2 ~ 6 alkenyl group", "C2 ~ 6 alkynyl group", "C3 ~ 8 cycloalkyl group", "C1 ~ 6 alkoxy group", "amino group", " “C1-6 alkylthio group”, “C1-6 alkylsulfinyl group”, “C1-6 alkylsulfonyl group”, “halogeno group” and groups having substituents on these groups include those exemplified in the above X ¹ The same thing is mentioned.

X ¹¹ is preferably an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C1-6 alkoxy group, or a halogeno group.
X ¹¹ is more preferably a halogeno group or a cyano group.
m1 is preferably an integer of 0 or 1.

Examples of the azolyl oxime compound of the present invention include an azolyl oxime compound represented by the formula (III) (hereinafter sometimes referred to as compound (III)).

In the formula (III), X ¹ , A, X ² , n, R ¹ , and the bond represented by the crossed solid line are as described above.
In the formula (III), X ¹¹ and m1 are as described above.

The salt of the azolyl oxime compound of the present invention is a salt of any of the compounds (I) to (III). 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 bases such as ammonia, triethylamine, tributylamine, pyridine and hydrazine. The salt of the azolyl oxime compound can be obtained by a known method.

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

[Pesticides]
The azolyl oxime compound of the present invention or a salt thereof (hereinafter sometimes referred to as “the compound of the present invention”) has an excellent pest control effect such as various agricultural pests and mites that affect plant growth. 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.

In addition, the compounds of the present invention can be used for a wide variety of filamentous fungi such as fungi belonging to algae (Oomycetes), Ascomycetes, Deuteromycetes, and basidiomycetes. Excellent control of plant pathogens. Therefore, it is useful as an active ingredient of a bactericide.

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, etc. to control various agricultural pests and mites, and further to control various phytopathogenic fungi. it can.

The pest control agent of the present invention is used in combination or in combination with bactericides, insecticides / acaricides, nematicides, soil insecticides, plant regulators, synergists, fertilizers, soil conditioners, animal feeds, etc. May be.

The compound of the present invention is useful as an active ingredient of an ectoparasite control agent because it is excellent in the control effect of ectoparasites 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;

[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 part in a formulation prescription shows a mass part. Examples of formulations for agricultural and horticultural use are 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 of 6- (3,3-Dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime (Compound No. 1-1) Synthesis (Step 1) Synthesis of 4-chloro-6- (3,3-dimethylbutoxy) pyrimidine

55 g of sodium hydride (2.0 g, 45.7 mmol) was suspended in 70 ml of tetrahydrofuran. Under cooling with ice, 3.78 g (37.0 mmol) of 3,3-dimethylbutanol was added dropwise to the suspension, followed by stirring at room temperature for 15 minutes. To this was added dropwise 8 ml of a tetrahydrofuran solution of 5.0 g (33.6 mmol) of 4,6-dichloropyrimidine. Then, it stirred at room temperature for 4 hours. A saturated aqueous ammonium chloride solution was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure to give 7.21 g (33.6 mmol, 100% yield) of 4-chloro-6- (3,3-dimethylbutoxy) pyrimidine. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 4-chloro-6- (3,3-dimethylbutoxy) pyrimidine: 8.55 (1H, s), 6.72 (1H, s), 4.42 ( 2H, t), 1.68 (2H, t), 0.96 (9H, s).

(Step 2) Synthesis of 6- (3,3-dimethylbutoxy) pyrimidine-4-carbonitrile

1.0 g (4.66 mmol) of 4-chloro-6- (3,3-dimethylbutoxy) pyrimidine was added to 10 ml of a 57% aqueous hydrogen iodide solution, and the mixture was stirred overnight at room temperature. 10 ml of water was added thereto, and the pH was adjusted to 7 with potassium carbonate. Then, it extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure. The resulting residue, 4- (3,3-dimethylbutoxy) -6-iodopyrimidine, 10 ml of pyridine and 0.39 g (4.66 mmol) of copper cyanide were mixed and heated to reflux overnight. This was concentrated under reduced pressure. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.53 g (2.58 mmol, yield 55%) of 6- (3,3-dimethylbutoxy) pyrimidine-4-carbonitrile. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 6- (3,3-dimethylbutoxy) pyrimidine-4-carbonitrile: 8.81 (1H, d), 7.03 (1H, d), 4.47 (2H, t), 1.70 (2H, t), 0.97 (9H, s).

(Step 3) Synthesis of 6- (3,3-dimethylbutoxy) -N′-hydroxypyrimidine-4-carboxyimidamide

0.53 g (2.58 mmol) of 6- (3,3-dimethylbutoxy) pyrimidine-4-carbonitrile was dissolved in methanol (6 ml). To this solution, 0.23 g (3.35 mmol) of hydroxylamine hydrochloride and 0.45 g (3.23 mmol) of potassium carbonate were added and heated to reflux for 3 hours. This was concentrated under reduced pressure. Water was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure to give 0.54 g (2.27 mmol yield 88%) of 6- (3,3-dimethylbutoxy) -N′-hydroxypyrimidine-4-carboxyimidamide. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 6- (3,3-dimethylbutoxy) -N′-hydroxypyrimidine-4-carboxyimidamide: 8.72 (1H, d), 7.19 ( 1H, d), 4.41 (2H, t), 1.70 (2H, t), 0.97 (9H, s).

(Step 4) Synthesis of 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carbimidoyl chloride

0.073 g (1.68 mmol) of 55 mass% sodium hydride was suspended in 3 ml of N, N-dimethylformamide. A solution of 0.40 g (1.68 mmol) of 6- (3,3-dimethylbutoxy) -N′-hydroxypyrimidine-4-carboxyimidamide in N, N-dimethylformamide was added to the suspension under ice cooling. 6 ml was added dropwise. Then, it stirred at room temperature for 30 minutes. Next, 0.29 g (1.85 mmol) of ethyl iodide was added dropwise thereto under ice cooling. Then, it stirred at room temperature for 2 hours. Water was added to this and then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the inorganic material was removed by filtration. The filtrate was concentrated under reduced pressure. The obtained 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carboxyimidamide was mixed with 3 ml of acetic acid and 6 ml of concentrated hydrochloric acid. An aqueous solution of 0.23 g (3.36 mmol) of sodium nitrite was added dropwise to the mixture at −15 ° C. Then, it stirred at room temperature for 4 hours. Ethyl acetate was added thereto and neutralized with an aqueous sodium hydroxide solution. Then, it extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and the inorganic material was removed by filtration. The filtrate was concentrated under reduced pressure to obtain 0.40 g (1.40 mmol, 83% yield) of 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carbimidoyl chloride. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carbimidoyl chloride: 8.82 (1H, s), 7.20 (1H, s), 4.46-4.39 (4H, m), 1.75-1.65 (2H, m), 1.45-1.35 (3H, m), 0.98 (9H, s).

(Step 5) Synthesis of 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime

To 8 ml of an N, N-dimethylformamide solution of 0.40 g (1.40 mmol) of 6- (3,3-dimethylbutoxy) -N′-ethoxypyrimidine-4-carbimidoyl chloride was added 1,2,4-triazole 0. .15 g (2.10 mmol) and 0.39 g (2.80 mmol) of potassium carbonate were added, heated to 90 ° C. and stirred overnight. Water was added to the resulting mixture at room temperature, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime. 0.22 g (0.69 mmol, 49% yield) was obtained. ¹ H-NMR data of the obtained 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime (CDCl ₃ / TMSδ (ppm)): 8.86 (1H, d), 8.80 (1H, d), 8.10 (1H, t), 7.03 (1H, s), 4.49-4.39 (4H, m), 1.74-1.70 (2H, m ), 1.42-1.35 (3H, m), 0.99 (9H, s).

[Example 2]
6- (3,3-Dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-isopropyloxime (compound number 1-2) Manufactured. ¹ H-NMR data of the obtained 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-isopropyloxime (CDCl ₃ / TMSδ (ppm)): 8.87 (1H, s), 8.80 (1H, d), 8.08 (1H, s), 7.05 (1H, d), 4.69-4.61 (1H, m), 4.49-4.45 (2H, m ), 1.75-1.71 (2H, m), 1.38-1.33 (6H, dd), 1.00 (9H, s).

Example 3
6- (3,3-Dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-methyloxime (Compound No. 1-3) Manufactured. ¹ H-NMR data of the obtained 6- (3,3-dimethylbutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-methyloxime (CDCl ₃ / TMSδ (ppm)): 8.82-8.81 (2H, m), 8.09 (1H, s), 7.03 (1H, d), 4.51-4.45 (2H, m), 4.16 (3H, s), 1.74-1.70 (2H , m), 0.99 (9H, s).

Example 4 6- (2,2,3,4,4,4-Hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyl Synthesis of oxime (Compound No. 1-15) (Step 1) Synthesis of 6-chloro-N-ethoxypyrimidine-4-carboxamide

To 1.00 g (7.14 mmol) of 6-hydroxypyrimidine-4-carboxylic acid was added 30 ml of methylene chloride, 3.60 g (28.4 mmol) of oxalyl chloride and 0.05 g (0.68 mmol) of N, N-dimethylformamide. Heated to reflux for 3 hours. The reaction was concentrated under reduced pressure. 30 ml of methylene chloride was added to the resulting residue, 0.70 g (7.18 mmol) of O-ethylhydroxylammonium chloride and 1.45 g (14.3 mmol) of triethylamine were added under ice cooling, and the mixture was stirred at room temperature for 3 hours. . The reaction was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.79 g (3.92 mmol, 55% yield) of 6-chloro-N-ethoxypyrimidine-4-carboxamide. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 6-chloro-N-ethoxypyrimidine-4-carboxamide: 10.08 (1H, s), 9.00 (1H, s), 8.13 (1H, s ), 4.11 (2H, q), 1.35 (3H, t).

(Step 2) Synthesis of 6-chloro-N-ethoxypyrimidine-4-carbimidoyl chloride

To 15 ml of acetonitrile solution of 1.00 g (4.96 mmol) of 6-chloro-N-ethoxypyrimidine-4-carboxamide was added 3.90 g (14.9 mmol) of triphenylphosphine and 4.58 g (29.8 mmol) of carbon tetrachloride. In addition, the mixture was heated to reflux for 6 hours. The reaction was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain 0.71 g (3.23 mmol, 65% yield) of 6-chloro-N-ethoxypyrimidine-4-carbimidoyl chloride. ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)) of the obtained 6-chloro-N-ethoxypyrimidine-4-carbimidoyl chloride: 9.06 (1H, s), 7.90 (1H, s), 4.45 ( 2H, q), 1.41 (3H, t).

(Step 3) Synthesis of 6- (1H-1,2,4-triazol-1-yl) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime

To 3 ml of an N, N-dimethylformamide solution of 0.12 g (0.55 mmol) of 6-chloro-N-ethoxypyrimidine-4-carbimidoyl chloride, 0.11 g (1.59 mmol) of 1,2,4-triazole and Potassium carbonate 0.22g (1.59mmol) was added, and it heated at 110 degreeC, and stirred for 3 hours. Water was added to the resulting mixture at room temperature, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 6- (1H-1,2,4-triazol-1-yl) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) ) 0.11 g (0.39 mmol, 71% yield) of methanone-O-ethyloxime was obtained. The resulting 6- (1H-1,2,4- triazol-1-yl) pyrimidin-4-yl - (IH-1,2,4-triazol-1-yl) ¹ H methanone -O- ethyl oxime -NMR data (CDCl ₃ / TMSδ (ppm)): 9.27 (1H, s), 9.09 (1H, s), 8.85 (1H, s), 8.25 (1H, s), 8.17 (1H, s), 8.11 ( 1H, s), 4.47 (2H, q), 1.41 (3H, t).

(Step 4) 6- (2,2,3,4,4,4-Hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime Synthesis of

0.10 g (0. 1H-1,2,4-triazol-1-yl) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime 35 mmol) of N, N-dimethylformamide in 2 ml of 2,2,3,4,4,4-hexafluorobutanol 0.09 g (0.49 mmol) and potassium carbonate 0.07 g (0.51 mmol) were added, Heat to 110 ° C. and stir for 6 hours. Water was added to the resulting mixture at room temperature, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and then the inorganics were removed by filtration. The filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give 6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazole-1 0.08 g (0.20 mmol, 57% yield) of -yl) methanone-O-ethyloxime was obtained. Of the obtained 6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-ethyloxime ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)): 8.86 (1H, s), 8.85 (1H, s), 8.10 (1H, s), 7.24 (1H, s), 5.18-5.01 (1H, m ), 4.88-4.81 (2H, m), 4.43 (2H, q), 1.40 (3H, t).

Example 5
6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-- Isopropyl oxime (Compound No. 1-77) was prepared. Of the obtained 6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-isopropyloxime ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)): 8.87 (1H, s), 8.85 (1H, s), 8.09 (1H, s), 7.25 (1H, s), 5.19-5.01 (1H, m ), 4.88-4.82 (2H, m), 4.69-4.62 (1H, m), 1.38 (6H, d).

Example 6
6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-- Methyl oxime (Compound No. 1-75) was prepared. Of the resulting 6- (2,2,3,4,4,4-hexafluorobutoxy) pyrimidin-4-yl- (1H-1,2,4-triazol-1-yl) methanone-O-methyloxime ¹ H-NMR data (CDCl ₃ / TMSδ (ppm)): 8.85 (1H, s), 8.83 (1H, s), 8.10 (1H, s), 7.24 (1H, s), 5.18-5.00 (1H, m ), 4.88-4.80 (2H, m), 4.18 (3H, s).

The compounds of the present invention produced in the same manner as in Examples, including the compounds of Examples, are shown in Tables 1 and 2 below.
The abbreviations entered in Tables 1 and 2 represent the following meanings.
Et: ethyl group, ⁱ Pr: isopropyl group, Me: methyl group, ^t Bu: t-butyl group, Ph: phenyl group, ⁿ Hex: n-hexyl group, ⁱ Pen: isopentyl group, Py-3-yl: pyridine -3-yl group, ^c Pr: cyclopropyl group, Py-2-yl: pyridin-2-yl group, ^c Hex: cyclohexyl group.
The column of (X ¹¹ ) m1 is “-”: m1 is 0, and the column of (X ² ) n is “-”: n is 0.
* Regarding the abbreviations in the column of * 1, E represents E isomer, Z represents Z isomer, and EZ represents a mixture of E isomer and Z isomer.
The abbreviations entered in Table 2 have the following meanings.
A (3) represents A at the position marked with 3. Hereinafter, A (4) represents A at a position marked with 4, and A (5) represents A at a position marked with 5.

Table 3 shows the physical property values of the compounds described in Tables 1 and 2 above. “Mp” represents the melting point. “ND” represents a refractive index.

[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.
The bean aphid was released on the cowpea where the primary leaves developed. When 1 day had passed since the release, the 1st instar larvae were left and adults were removed. Subsequently, the emulsion was diluted with water to a compound concentration of 125 ppm, and this chemical solution was sprayed on the cowpea.
Thereafter, the cowpea was kept in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. When 4 days had passed since spraying, the aphids were examined for life and death, and the insecticidal rate was determined.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All the compounds were 80% or more.
1-1, 1-3, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1-13, 1-15, 1- 16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-26, 1-27, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-46, 1-47, 1-48, 1-49, 1-50, 1- 51, 1-54, 1-58, 1-62, 1-65, 1-66, 1-68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-81, 1-82, 1-83, 1-86, 1-87, 1-88, 1-90, 1-91, 1-92, 1- 93, 1-94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-104, 1-110, and 1-111.

(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 chemical 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 plastic bags. The rice seedlings were kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since 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.

About the chemical | medical solution which respectively contains the compound shown below, it tested using the (A) drug sensitivity system | strain. All compounds had an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1- 13, 1-15, 1-16, 1-17, 1-18, 1-20, 1-21, 1-22, 1-25, 1-26, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-38, 1-39, 1-40, 1-41, 1-43, 1-46, 1-47, 1-48, 1-49, 1- 50, 1-51, 1-58, 1-63, 1-65, 1-66, 1-68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-81, 1-82, 1-83, 1-86, 1-87, 1-90, 1-93, 1-94, 1- 95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-107, 1-110, 1-111, and 1-121.

In the same manner, the efficacy test was conducted at a compound concentration of 8 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-1, 1-2, 1-5, 1-7, 1-8, 1-10, 1-13, 1-15, 1-18, 1-20, 1-22, 1-25, 1- 32, 1-33, 1-39, 1-46, 1-47, 1-51, 1-66, 1-68, 1-69, 1-71, 1-72, 1-76, 1-78, 1-80, 1-81, 1-83, 1-86, 1-93, 1-94, 1-111, and 1-121.
In the same manner, the efficacy test was conducted at a compound concentration of 2 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-4, 1-21, 1-26, 1-35, 1-36, 1-65, and 1-77.

About the chemical | medical solution which respectively contains the compound shown below, it tested using the (B) chemical | medical agent low sensitivity system | strain. All compounds had an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-15, 1-21, 1-26, 1-36, 1-38, 1-39, 1-40, 1- 46, 1-47, 1-65, 1-66, 1-69, 1-77, 1-78, 1-79, 1-80, 1-86, 1-94, and 1-95.

In the same manner, the efficacy test was conducted at a compound concentration of 31 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-2, 1-4, 1-5, 1-15, 1-26, 1-46, 1-47, 1-69, 1-80, 1-86, and 1-94.
In the same manner, the efficacy test was conducted at a compound concentration of 8 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-1, 1-21, 1-66, 1-77, and 1-78.

Imidacloprid showed an insecticidal rate of 100% at 125 ppm with respect to (A) drug-sensitive line. (B) The insecticidal rate was 50% for the drug-insensitive line.

Buprofezin showed a 100% insecticidal rate at 125 ppm with respect to (A) drug-sensitive line. (B) The insecticidal rate was 70% for the drug-insensitive line.

(Compound No. 26) shown below in Patent Document 2 showed an insecticidal rate of 80% or more at 31 ppm with respect to (A) drug-sensitive strain, but showed an insecticidal rate of 80% or more at 8 ppm. There wasn't.

(Test Example 3) Efficacy test against cotton aphids Adult cotton aphids were released on cucumbers that had been sown in 3-inch pots and 10 days after germination. When 1 day had passed since the release, the 1st instar larvae were left and adults were removed. The emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm, and this chemical solution was sprayed onto the cucumber.
Thereafter, the cucumber was kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. After 5 days from spraying, the aphids were examined for life and death, and the insecticidal rate was determined.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All compounds had an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-9, 1-10, 1-11, 1-12, 1- 13, 1-15, 1-16, 1-17, 1-18, 1-19, 1-20, 1-21, 1-22, 1-25, 1-26, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-37, 1-38, 1-39, 1-40, 1-41, 1-46, 1-47, 1-48, 1- 49, 1-50, 1-51, 1-58, 1-63, 1-65, 1-66, 1-69, 1-71, 1-72, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 1-83, 1-86, 1-87, 1-88, 1-90, 1-91, 1-92, 1-93, 1- 94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-104, 1-106, 1-107, 1-110, 1-111, And 1-121.

In the same manner, the efficacy test was conducted at a compound concentration of 31 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-2, 1-3, 1-4, 1-5, 1-13, 1-16, 1-19, 1-30, 1-32, 1-33, 1-37, 1-46, 1- 47, 1-48, 1-49, 1-50, 1-51, 1-63, 1-69, 1-86, 1-87, 1-88, 1-94, 1-95, 1-96, 1-97, 1-98, 1-99, 1-101, and 1-110.
In the same manner, the efficacy test was conducted at a compound concentration of 8 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-1, 1-7, 1-10, 1-12, 1-15, 1-17, 1-18, 1-20, 1-21, 1-22, 1-26, 1-31, 1- 35, 1-36, 1-38, 1-39, 1-40, 1-58, 1-65, 1-66, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-93, 1-100, 1-104, 1-111, and 1-121.

In addition, although description (compound No. 26) described in patent document 2 showed an insecticidal rate of 80% or more at 125 ppm, it did not show an insecticidal rate of 80% or more at 31 ppm.

(Test Example 4) Efficacy test against peach aphid Adult peach aphid was released on a Japanese radish seedling. When 1 day had passed since the release, the 1st instar larvae were left and adults were removed. The emulsion described in Test Example 1 was diluted with water so that the compound concentration was 125 ppm, and the radish was immersed in this chemical solution for 10 seconds.
Thereafter, the radish was kept in a temperature-controlled room at a temperature of 25 ° C. and a humidity of 60%. When 6 days have passed since the immersion, the mortality of the peach aphid was examined to determine the insecticidal rate.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All compounds had an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-5, 1-6, 1-10, 1-12, 1-13, 1-15, 1-17, 1-18, 1-20, 1- 21, 1-22, 1-26, 1-31, 1-36, 1-37, 1-38, 1-39, 1-40, 1-46, 1-47, 1-48, 1-49, 1-51, 1-58, 1-65, 1-66, 1-69, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-82, 1- 86, 1-93, 1-94, 1-96, 1-97, 1-98, 1-99, 1-100, 1-101, 1-104, 1-111, and 1-121.

In the same manner, the efficacy test was conducted at a compound concentration of 31 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-3, 1-10, 1-15, 1-20, 1-21, 1-26, 1-31, 1-46, 1-47, 1-48, 1-58, 1-65, 1- 66, 1-69, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-94, 1-96, 1-97, 1-98, 1-99, 1-104, 1-111, and 1-121.

In addition, (Compound No. 26) described in Patent Document 2 did not show an insecticidal rate of 80% or more at 125 ppm.

(Test Example 5) Efficacy test against leafhopper leaf The emulsion described in Test Example 1 was diluted with water to a compound concentration of 125 ppm, and rice seedlings were immersed in this chemical solution for 10 seconds and allowed to air dry.
A plastic bag with a hole was put on the rice seedlings. Ten second instar larvae were released in a plastic bag. Rice seedlings were kept in a constant temperature room at a temperature of 25 ° C. and a humidity of 60%. When 6 days had passed since the release, the viability of the leafhopper was examined and the insecticidal rate was determined.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All compounds had an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-6, 1-7, 1-8, 1-10, 1-11, 1-12, 1-15, 1- 16, 1-17, 1-18, 1-20, 1-21, 1-22, 1-26, 1-27, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-38, 1-39, 1-40, 1-41, 1-43, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1- 54, 1-58, 1-63, 1-65, 1-66, 1-68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-80, 1-81, 1-83, 1-86, 1-88, 1-90, 1-91, 1-93, 1-95, 1-97, 1-98, 1- 99, 1-100, 1-101, 1-110, and 1-111.

In the same manner, the efficacy test was conducted at a compound concentration of 31 ppm. The compounds shown below showed an insecticidal rate of 80% or more.
1-1, 1-2, 1-3, 1-4, 1-5, 1-10, 1-11, 1-12, 1-15, 1-16, 1-17, 1-18, 1- 20, 1-21, 1-22, 1-26, 1-27, 1-30, 1-31, 1-32, 1-33, 1-35, 1-36, 1-38, 1-39, 1-40, 1-46, 1-47, 1-48, 1-49, 1-50, 1-51, 1-54, 1-58, 1-63, 1-65, 1-66, 1- 68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-80, 1-86, 1-90, 1-91, 1-93, 1-95, 1-97, 1-98, 1-99, 1-100, and 1-111.

(Test Example 6) Efficacy test against tobacco whitefly The emulsion described in Test Example 1 was diluted with water so that the concentration of the compound of the present invention was 125 ppm, and this test chemical 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. In this flask, 7 pairs of adult whitefly whitefly type B were released, infested with tomato cut leaves, and kept in a thermostatic chamber at a temperature of 25 ° C. and a humidity of 60%. When two days had passed since the release, adults were examined for viability and the insecticidal rate was determined.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All compounds had an insecticidal rate of 80% or more.
1-5, 1-10, 1-11, 1-15, 1-20, 1-21, 1-22, 1-26, 1-31, 1-32, 1-33, 1-35, 1- 36, 1-37, 1-38, 1-39, 1-40, 1-46, 1-51, 1-65, 1-66, 1-68, 1-69, 1-71, 1-72, 1-74, 1-75, 1-76, 1-77, 1-78, 1-79, 1-80, 1-83, 1-88, 1-94, and 1-100.

(Test Example 7) Apple scab control test First, 95 parts of dimethylformamide containing 1.5% of polyoxyethylene sorbitan monolaurate and 5 parts of the compound of the present invention were mixed and dissolved to give an emulsion containing 5% of active ingredient. Was prepared.
The above-mentioned emulsion was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm, and this seedling was cultivated in an unglazed pot (apple variety “Kokumi”, 3 (4th leaf stage).
After the leaves were air-dried, apple seedlings of Venturia inaequalis were inoculated into apple seedlings, and the apple seedlings were kept in a temperature-controlled room at 20 ° C. and high humidity for 2 weeks. . The lesion appearance on the leaves was compared with no treatment to determine the control value.
The test was conducted on a chemical solution containing the compound No. 1-2. This compound exhibited a control value of 75% or more.

(Test Example 8) The emulsion described in Test Example 7 for wheat powdery mildew control was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration would be 100 ppm. Was sprayed on wheat seedlings grown in an unglazed pot (variety “Chihoku”, 1.0-1.2 leaf stage).
After the leaves were air-dried, conidia of wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) were sprinkled and inoculated, and the wheat seedlings were kept in a 22-25 ° C. greenhouse for 7 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All the compounds had a control value of 75% or more.
1-1, 1-6, 1-10, 1-13, 1-15, 1-18, 1-21, 1-32, 1-33, 1-36, 1-39, 1-40, 1- 66, 1-69, 1-71, 1-72, 1-74, 1-76, 1-87, 1-93, 1-100, 2-1, and 2-2.

(Test Example 9) Wheat red rust control test The emulsion described in Test Example 7 was diluted with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm. Prepared. Subsequently, the chemical solution was sprayed on wheat seedlings grown in an unglazed pot (variety “Noribayashi No. 61”, 1.0 to 1.2 leaf stage).
After air-drying the leaves, summer spores of wheat red rust fungus (Puccinia recondita) were shaken off and inoculated, and wheat seedlings were kept in a 22-25 ° C. greenhouse for 10 days. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
The said test was done about the chemical | medical solution which respectively contains the compound shown below. All the compounds had a control value of 75% or more.
1-2, 1-65, 1-91, and 1-92.

(Test Example 10) Tomato plague control test The drug solution was prepared by diluting the emulsion described in Test Example 7 with water containing 0.01% polyoxyethylene sorbitan monolaurate so that the compound concentration was 100 ppm. did. Subsequently, the chemical solution was sprayed on tomato seedlings (variety “Regina”, 4-5 leaf stage) grown in an unglazed pot.
The leaves were air-dried and then sprayed with a zoospore suspension of Phytophthora infestans, and kept in a temperature-controlled room at 20 ° C. and high humidity for 4 days, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
The above test was conducted on a chemical solution containing the compound No. 1-6. This compound exhibited a control value of 75% or more.

It is possible to provide an azolyl oxime compound or a salt thereof, which is excellent in insecticidal activity and / or acaricidal activity, excellent in safety and can be synthesized industrially advantageously, and a pest control agent containing this as an active ingredient.

Claims

An azolyl oxime compound represented by the formula (I) or a salt thereof.

[In the formula (I), Het represents a 6-membered heteroaryl ring containing 2 to 3 nitrogen atoms as constituent atoms of the ring.
X 1 is a substituent on Het, which 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, hydroxy group, unsubstituted or substituted C1-6 alkoxy group, unsubstituted or substituted C2-6 alkenyloxy Group, unsubstituted or substituted C2-6 alkynyloxy group, unsubstituted or substituted C3-8 cycloalkyloxy group, unsubstituted or substituted C1-7 acyl group, unsubstituted Or a substituted C1-6 alkoxycarbonyl group, an unsubstituted or substituted C1-6 alkylcarbamoyl group, unsubstituted Or a substituted amino 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, unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl group, unsubstituted or substituted C6-10 aryloxy group, halogeno A 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.
A represents a carbon atom or a nitrogen atom.
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, a hydroxy 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, an unsubstituted or substituted amino group, a mercapto group, an unsubstituted or substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfonyl group, Unsubstituted or substituted C6-10 aryl group, unsubstituted or substituted 3-6 membered heterocyclyl Shows a halogeno group, a cyano group or a nitro group.
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.
R 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 A substituted C3-8 cycloalkyl group, an unsubstituted or substituted C6-10 aryl group, or an unsubstituted or substituted 3-6 membered heterocyclyl group is shown.
In the formula (I), a bond represented by crossed solid lines represents a double bond having stereoisomerism. ]
2. The azolyl oxime compound or a salt thereof according to claim 1, wherein m is an integer of any one of 1, 2, or 3.
The azolyl oxime compound or a salt thereof according to claim 1, wherein the formula (I) is represented by the formula (II).

[In the formula (II), X 11 represents an unsubstituted or substituted C1-6 alkyl group, an unsubstituted or substituted C2-6 alkenyl group, an unsubstituted or substituted C2-6 An alkynyl group, an unsubstituted or substituted C3-8 cycloalkyl group, a hydroxy group, an unsubstituted or substituted C1-6 alkoxy group, an unsubstituted or substituted amino group, an unsubstituted or A substituted C1-6 alkylthio group, an unsubstituted or substituted C1-6 alkylsulfinyl group, an unsubstituted or substituted C1-6 alkylsulfonyl group, a halogeno group, a cyano group, or a nitro group. Show.
m1 represents the number of X 11 and is an integer from 0 to 2. When m1 is 2 or more, X 11 may be the same as or different from each other.
The bonds represented by X 1 , A, X 2 , n, R 1 and the crossed solid line are as described above. ]
An azolyl oxime compound represented by the formula (III) or a salt thereof.

[In formula (III), X 1 , X 11 , m 1, A, X 2 , n, R 1 and the bond represented by the crossed solid line are as described above. ]
A pest control agent comprising as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of claims 1 to 4 and a salt thereof.
An insecticide or acaricide containing, as an active ingredient, at least one selected from the group consisting of the azolyloxime compound according to any one of claims 1 to 4 and a salt thereof.
A fungicide containing as an active ingredient at least one selected from the group consisting of the azolyloxime compound according to any one of claims 1 to 4 and a salt thereof.
An ectoparasite control agent comprising, as an active ingredient, at least one selected from the group consisting of the azolyloxime compound according to any one of claims 1 to 4 and a salt thereof.