JP2000103772A - Intermediate for manufacture of oxime ether compound - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound useful for as an intermediate for manufacturing an oxime ether compound having an excellent bactericidal activity for agriculture and horticulture. SOLUTION: This compound is expressed by formula I [R1 is a (substituted) alkyl or the like; R2 is an alkyl or the like; one of the T, U and V is CR3 the other one is CH or N and the resist is CR4 or N; W is a CR33 or N; R3, R4 and CR33 are each H or a halogen or the like; Me is methyl], for example, methyl 2- 2-methyl-5-(1-benzyloxyiminoethyl)-phenoxy}-3,3-dimethoxypropionic acid. The compound of formula I is obtained by refluxing a compound of formula II [e.g.; methyl 2- 2-methyl-5-(1-benzyl-oxyiminoerthyl)phenoxy}-3- hydroxyacrylate or the like] in the presence of p-toluene sulfonic acid hydrate with methanol, usually at 25 to its refluxing temperature for 1 to 20 hours.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to a method for producing an oxime ether compound, an intermediate for producing the same, and a method for producing the same.

[0002]

[Problems to be Solved by the Invention] General Formula 4

Embedded image [In the formula, R ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted Cycloalkylalkyl group,
An optionally substituted cycloalkenyl group, an optionally substituted cycloalkenylalkyl group, an optionally substituted aryl group, an optionally substituted arylalkyl group, an optionally substituted heteroaryl group or Represents an optionally substituted heteroarylalkyl group, R ² represents an alkyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group or a cyano group,
One of T, U and V represents a CR ³ group, the other represents a CH group or a nitrogen atom, and the other represents a CR ³ group.
Represents ⁴ groups or a nitrogen atom. W represents a CR ³³ group or a nitrogen atom, wherein R ³ , R ⁴ and R ³³ are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylthio group or Represents a haloalkylthio group. ｝. The compound represented by has excellent agricultural and horticultural bactericidal efficacy,
It has been desired to develop an advantageous method for producing these oxime ether compounds.

[0003]

Means for Solving the Problems The present inventors have conducted intensive studies to find an advantageous method for producing the oxime ether compound represented by the above-mentioned general formula (4), and as a result, have the following general formula (5). The compound was converted to an oxime ether compound represented by the above general formula 4 by reacting the compound in the presence of an acid, and was found to be an important intermediate for the production thereof, and the present invention was achieved. . That is, the present invention provides a compound represented by the general formula:

Embedded image [Wherein, R ¹ , R ² , T, U, V, and W represent the same meaning as described above. (Hereinafter referred to as the compound of the present invention), a process for producing the same, and a process for producing the oxime ether compound represented by the above general formula (4), wherein the compound is reacted in the presence of an acid.

[0004]

BEST MODE FOR CARRYING OUT THE INVENTION In the compound of the present invention, examples of the alkyl group in the optionally substituted alkyl group represented by R ¹ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, 1-methylpropyl group, pentyl group, 1-methylbutyl group, 1
-Ethylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethyl Pentyl group,
Examples thereof include a C1-C10 alkyl group such as a 3,3-dimethylbutyl group, a heptyl group, and a 3,7-dimethyloctyl group, and examples of the alkenyl group in the optionally substituted alkenyl group represented by R ¹ include: Vinyl group, allyl group, 1-methyl-2-propenyl group, 2-methyl-2
-Propenyl group, 2-butenyl group, 2-pentenyl group,
C2-C such as 3-methyl-2-butenyl group and geranyl group
And the alkynyl group in the optionally substituted alkynyl group represented by R ¹ includes, for example, an ethynyl group, a propargyl group, a 1-methyl-2-propynyl group, a 3-methyl-2-propynyl Examples of the cycloalkyl group in the optionally substituted cycloalkyl group represented by R ¹ include C3 to C10 alkynyl groups such as a C3 to C10 cycloalkyl group such as a cyclopropyl group, a cyclopentyl group and a cyclohexyl group. Examples of the cycloalkylalkyl group in the optionally substituted cycloalkylalkyl group represented by R ¹ include a cyclopropylmethyl group, a cyclopentylmethyl group, a 2-cyclopentylethyl group, a cyclohexylmethyl group and the like. C4-C20 cycloalkylalkyl Group, etc. Examples of the cycloalkenyl group in the optionally substituted cycloalkenyl group represented by R ^1, for example, cyclopentenyl group,
Examples thereof include a C5-C10 cycloalkenyl group such as a cyclohexenyl group. Examples of the cycloalkenyl group in the optionally substituted cycloalkenylalkyl group represented by R ¹ include a cyclopenten-1-ylmethyl group and a cyclohexene-1- group. C6-C2 such as ylmethyl group
0 cycloalkenylalkyl group and the like, and the aryl in the optionally substituted aryl group represented by R ¹
Examples of the aryl group include a C6-C10 aryl group such as a phenyl group, an α-naphthyl group, and a β-naphthyl group.
Ants in Ruarukiru group - - Good ants be substituted indicated by ¹ as the Ruarukiru groups, such as phenyl methyl group, 2-phenylethyl, 3-phenyl -n-
A C7-C20 arylalkyl group such as a propyl group, a 4-phenyl-n-butyl group, an α-naphthylmethyl group and a β-naphthylmethyl group, and an optionally substituted heteroaryl group represented by R ¹ As the heteroaryl group in the above, for example, a 2-pyridyl group, a 4-pyridyl group, a 2-pyrimidinyl group, a 4-pyrimidinyl group, a 3-pyrazolyl group, a 2-thiazolyl group, a 2-imidazolyl group,
A C1-C9 heteroaryl group such as a 3- (1,2,4-triazolyl) group and a 2-quinolinyl group, and a heteroarylalkyl group in the optionally substituted heteroarylalkyl group represented by R ¹ Is, for example, a 2-pyridylmethyl group, a 4-pyridylmethyl group, a 2-pyrimidinylmethyl group, a 4-pyrimidinylmethyl group,
C2-C1 such as pyrazolylmethyl group, 2-thiazolylmethyl group, 2-imidazolylmethyl group, 3- (1,2,4-triazolyl) methyl group, 2-quinolinylmethyl group
9 heteroarylalkyl groups,

In R ¹ , an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, and an optionally substituted A cycloalkylalkyl group, a cycloalkenyl group which may be substituted,
Optionally substituted cycloalkenylalkyl group, optionally substituted aryl group, optionally substituted arylalkyl group, optionally substituted heteroaryl group or optionally substituted heteroarylalkyl group the substituents include a halogen atom [a chlorine atom, a bromine atom, a fluorine atom, etc.]; OR ⁸ group [wherein,
R ⁸ is a C1-C10 alkyl group {eg, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert-butyl group, a pentyl group, a hexyl group, etc.}, a C1-C5 haloalkyl group {eg, Trifluoromethyl group, difluoromethyl group, bromodifluoromethyl group, 1,1,2,2-tetrafluoroethyl group,
2,2,2-tolylfluoroethyl group etc., C3-C6
A cycloalkyl group {for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.} or a phenyl group; the phenyl group is a halogen atom (a chlorine atom, a bromine atom, a fluorine atom, etc.), a C1-C5 alkyl group (for example,
Methyl group, ethyl group, tert-butyl group, etc.) or trifluoromethyl group, for example,
Phenyl group, 4-chlorophenyl group, 4- (trifluoromethyl) phenyl group, 3,4-dichlorophenyl group,
4-ethylphenyl group, 2,3-dimethylphenyl group,
2-chloro-4- (trifluoromethyl) phenyl group,
4-fluorophenyl group, 3,5-dichlorophenyl group, 4-tert-butylphenyl group, 2-chloro-6
— Represents a fluorophenyl group or the like. ]; C (R ¹³ ) = N
A group represented by OR ¹⁴ wherein R ¹³ and R ¹⁴ are the same or different and each represent a hydrogen atom, a C1 to C10 alkyl group {eg, a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, a tert group; A butyl group, a pentyl group, a hexyl group or the like, a C3-C6 cycloalkyl group {for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group}, or a phenyl group; the phenyl group is a halogen atom (a chlorine atom, a bromine atom, A fluorine atom), a C1-C5 alkyl group (eg, a methyl group, an ethyl group, a tert-butyl group, etc.), a trifluoromethyl group or a cyano group, for example, a phenyl group, a 4-chlorophenyl group , 4-trifluoromethylphenyl group, 4-ethylphenyl group, 3,4-dichlorophenyl group, 3,5- Chlorophenyl group, 2-chloro-6-fluorophenyl group, 4-fluorophenyl group, a 4-cyanophenyl group and the like}. ]; C1 to C5
Alkylthio group [eg, methylthio group, ethylthio group, propylthio group, isopropylthio group, pentylthio group, etc.]; C1-C5 haloalkylthio group [eg,
2,2,2-trifluoroethylthio group, 4-chlorobutylthio group, etc.]; C1 to C10 acyl group [for example, C1 which may be substituted with a halogen atom {a chlorine atom, a bromine atom, a fluorine atom, etc.}] -C10 alkanoyl group {formyl group, acetyl group, propanoyl group, butanoyl group, pentanoyl group, isobutanoyl group, etc.}, benzoyl group etc.]; C2-C11 alkoxycarbonyl group [for example,
A methoxycarbonyl group, an ethoxycarbonyl group, a propyloxycarbonyl group, an isopropyloxycarbonyl group, a butyloxycarbonyl group, an octyloxycarbonyl group, etc.]; an N- (C1-C10 alkyl) carbamoyl group [for example, an N-methylcarbamoyl group, N N, N-di (C1-C10 alkyl) carbamoyl group [eg, N, N-dimethylcarbamoyl group, N, N-diethylcarbamoyl group, etc.]; cyano group; aryl group [phenyl Group, α-naphthyl group, β-
Naphthyl group and the like. The aryl group may be a halogen atom {a chlorine atom, a bromine atom, a fluorine atom, etc.}, a C1-C10 alkyl group {eg, a methyl group, an ethyl group, a tert-butyl group, etc.}, a C3-C10 cycloalkyl group, etc. Cyclopropyl group, cyclopentyl group, cyclohexyl group, etc.
A C1-C5 haloalkyl group {such as a trifluoromethyl group, etc.}, a C1-C10 alkoxy group {such as a methoxy group, an ethoxy group, a propyloxy group, an isopropyloxy group, etc.}, a C1-C5 haloalkoxy group {such as a trifluoromethoxy group, Difluoromethoxy group, etc., cyano group, C5-C8 cycloalkoxy group {eg, cyclopentyloxy group, cyclohexyloxy group, etc.}, C1
C10 acyl group ｛for example, C1 to C10 such as acetyl group
Alkanoyl group, benzoyl group and the like, phenoxy group, and the phenoxy group is a halogen atom (a chlorine atom, a bromine atom,
A fluorine atom), a C1-C3 alkyl group (methyl group, ethyl group, etc.), a C1-C3 haloalkyl group (trifluoromethyl group, etc.) or a C1-C3 alkylthio group (methylthio group, etc.) For example, a phenoxy group, a 4-chlorophenoxy group or the like, a phenyl group optionally substituted with a cyano group, a 2-pyridyloxy group, wherein the 2-pyridyloxy group is substituted with a trifluoromethyl group or a halogen atom. For example, a 5-trifluoromethylpyridin-2-yloxy group, a 3-chloro-5-trifluoromethylpyridin-2-yloxy group and the like can be mentioned. Even when substituted with a benzyloxy group or a benzoyloxy group, Good. Or a heteroaryl group [eg, a 2-pyridyl group, a 3-pyridyl group, a 4
-Pyridyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 5-pyrimidinyl group, 1-pyrazolyl group, 3-pyrazolyl group, 4-pyrazolyl group, 5-pyrazolyl group, 2-
Thiazolyl group, 4-thiazolyl group, 5-thiazolyl group,
4-isoxazolyl group, 1- (1,2,4-triazolyl) group, 3- (1,2,4-triazolyl) group, 3-oxolanyl group, succinimide-1-yl group, maleic imide-1 -Yl group, phthalimido-1-yl group and the like. The heteroaryl group is a halogen atom ｛a chlorine atom,
A bromine atom, a fluorine atom, etc., a C1-C10 alkyl group {eg, a methyl group, an ethyl group, a tert-butyl group, etc.}, a C3-C10 cycloalkyl group {eg, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group, etc.},
C1-C5 haloalkyl group {eg, trifluoromethyl group etc.}, C1-C10 alkoxy group {eg, methoxy group, ethoxy group, etc.} or C1-C10 alkylthio group {eg, methylthio group, ethylthio group, etc.} . ] Etc. are given,

Examples of the alkyl group represented by R ² include a methyl group, an ethyl group, a propyl group, an isopropyl group,
Butyl, isobutyl, 1-methylpropyl, pentyl, 1-methylbutyl, 1-ethylbutyl, 2
-Methylbutyl group, 3-methylbutyl group, 2,2-dimethylpropyl group, 1,2-dimethylpropyl group, 1,1
C1 such as -dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethylpentyl group, 3,3-dimethylbutyl group, heptyl group, 3,7-dimethyloctyl group, etc.
~C10 alkyl group and the like, the cycloalkyl group represented by R ^2, for example, cyclopropyl group, cyclopentyl group, etc. C3~C10 cycloalkyl groups such as cyclohexyl group and the like, alkoxyalkyl represented by R ² as the base, for example, methoxymethyl group, 2-ethoxyethyl group, 4-methoxybutyl group, 5-pentyloxy pentyl C2~C10 alkoxyalkyl group such as and the like, as the haloalkyl group represented by R ^2, For example, trifluoromethyl group, chloromethyl group, 2
C1 to C5 haloalkyl groups such as -fluoroethyl group and the like;

The halogen atom represented by R ³ , R ⁴ and R ³³ includes, for example, a chlorine atom, a bromine atom and a fluorine atom, and the alkyl group represented by R ³ , R ⁴ and R ³³ includes, for example, methyl Group, ethyl group, propyl group, isopropyl group, butyl group, isobutyl group, 1-methylpropyl group, pentyl group, 1-methylbutyl group, 1-ethylbutyl group, 2-methylbutyl group, 3-methylbutyl group, 2,
2-dimethylpropyl group, 1,2-dimethylpropyl group, 1,1-dimethylpropyl group, hexyl group, 1-methylpentyl group, 1-ethylpentyl group, 3,3-dimethylbutyl group, heptyl group, 3, 7- C1 -C10 alkyl dimethyl octyl group and the like, R ^3, the alkoxy group represented by R ⁴ and R ³³ include a methoxy group, an ethoxy group, n- propoxy group, i- propoxy, n- butoxy group, sec- butoxy group, i- butoxy group, n-C1 -C10 alkoxy group such as a pentyloxy group and the like, R ^3, examples of a haloalkyl group represented by R ⁴ and R ³³ such as trifluoromethyl group, 2,2
Examples thereof include a C1 to C10 haloalkyl group such as a 2-trifluoroethyl group and a 1,1,2,2-tetrafluoroethyl group. As the haloalkoxy group represented by R ³ , R ⁴ and R ³³ , for example, trifluoro C1-C10 halo such as methoxy group, difluoromethoxy group, difluorobromomethoxy group, difluorochloromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1,2,2-tetrafluoroethoxy group, etc. Alkoxy groups are exemplified. Examples of the alkylthio groups represented by R ³ , R ⁴ and R ³³ include, for example, methylthio, ethylthio, n-propylthio, n-butylthio, i-butylthio, sec-
-Butylthio group, n-pentylthio group, C1-C10 alkylthio groups such as n-hexylthio group,
Examples of the haloalkylthio groups represented by R ³ , R ⁴ and R ³³ include, for example, trifluoromethylthio, difluoromethylthio, difluorobromomethylthio, difluorochloromethylthio, fluoromethylthio, 2,2,2
C1 to C10 haloalkylthio groups such as -trifluoroethylthio group, 1,1,2,2-tetrafluoroethylthio group,

Specific examples of the 6-membered aromatic ring containing T, U, V and W include a benzene ring, a pyridine ring and a pyrimidine ring.

The compound according to the present invention has a C ＝ N bond,
The isomers (E) and (Z) based on the C ＝ C bond may exist, and each and a mixture thereof are included in the compounds involved in the method of the present invention. (The terms (E) and (Z) as used herein are those defined by the Cahn-Ingold-Prelog rule, which is widely used to indicate geometric isomers.)

The compound of the present invention has the general formula [Wherein, R ¹ and R ² represent the same meaning as described above. Is produced by reacting the compound represented by the formula (1) with methanol in the presence of an acid (hereinafter referred to as production step 1 of the present invention). In the reaction, the yield of the compound of the present invention is improved,
Alternatively, for the purpose of shortening the reaction time, methyl orthoformate can be coexisted. The reaction can be performed without a solvent or in a solvent. The reaction temperature of the reaction is usually in the range of 25 ° C. to the reflux temperature of methanol,
The reaction time is usually in the range of 1 to 20 hours. The amount of the reagent used for the reaction is determined by the amount of the compound 1 represented by the above general formula (6).
Methanol ranges from 2 moles to a large excess, and the acid ranges from 0.0001 to 10 moles, based on moles. Examples of the acid used include hydrochloric acid, sulfuric acid, nitric acid, boric acid,
Minerals such as phosphoric acid and polyphosphoric acid, acetic acid, trifluoroacetic acid,
Oxalic acid, carboxylic acids such as benzoic acid, chlorosulfonic acid,
Sulfonic acids such as tosylic acid, camphorsulfonic acid, methanesulfonic acid, trifluoromethanesulfonic acid, zinc chloride, boron trifluoride diethyl ether complex,
And Lewis acids such as trimethylsilyl chloride.
Examples of the solvent include ether solvents such as 1,4-dioxane and tetrahydrofuran; aliphatic hydrocarbon solvents such as hexane and heptane; aromatic hydrocarbon solvents such as benzene, toluene and xylene; chloroform; 1
Halogenated hydrocarbon solvents such as trichloroethane and monochlorobenzene; sulfur compound solvents such as dimethyl sulfoxide and sulfolane; and mixtures thereof. When coexisting with methyl orthoformate,
The amount used is in the range of 2 mol to a large excess with respect to 1 mol of the compound represented by the general formula (6). After completion of the reaction, the reaction solution is neutralized with a base, if necessary, concentrated, and then diluted with an organic solvent. An inventive compound can be obtained. The compound of the present invention can be purified by recrystallization, chromatography, or the like.

The compound represented by the general formula 6 used in the production process 1 of the present invention is, for example, a compound represented by the formula

Embedded image Wherein R ¹ , R ² , T, U, V and W have the same meaning as described above. ] Can be produced. The production method can be carried out by reacting compound [1] with methyl formate in a solvent in the presence of a base. The reaction temperature of the reaction is usually in the range of 0 to 150 ° C, and the reaction time is usually in the range of 1 to 24 hours. The amount of the reagent used for the reaction is 1 to 100 mol of methyl formate and 1 to 100 mol of the base per 1 mol of the compound [1].
As the base, for example, sodium hydride, inorganic bases such as potassium hydride, sodium methoxide, sodium ethoxide, alkali metal alkoxides such as potassium tert-butoxide, alkaline earth metal alkoxides such as magnesium ethoxide, Sodium amide,
Examples thereof include alkali metal amides such as lithium amide, lithium diisopropylamide, sodium hexamethyldisilazide, and lithium hexamethyldisilazide, and mixtures thereof. Examples of the solvent include methanol, ethanol, propanol, butanol, and isopropanol.
Alcohol-based solvents such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether,
Ether solvents such as diethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbon solvents such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbon solvents such as toluene and xylene; Halogenated hydrocarbon solvents such as dichloroethane, carbon tetrachloride, and monochlorobenzene; organic base solvents such as pyridine, triethylamine, N-methylaniline, N, N-dimethylaniline, N, N-diethylaniline; nitroethane; nitrobenzene; Nitro compound solvent,
Examples thereof include nitrile solvents such as acetonitrile and isobutyronitrile, N, N-dimethylformamide, dimethylsulfoxide, N, N-dimethyl-2-imidazolidone, sulfolane and the like, and mixtures thereof. After completion of the reaction, the reaction solution is poured into an acidic aqueous solution such as dilute hydrochloric acid, and the resulting compound is subjected to post-treatment operations such as extraction and concentration with an organic solvent to obtain the desired compound represented by the above general formula 6. Can be. The compound can be purified by recrystallization, chromatography or the like.

Next, the compounds of the present invention obtained by the production process 1 of the present invention are shown in Tables 1 to 8, but the present invention is not limited thereto.

Embedded image A compound represented by the formula:

[0013]

[Table 1]

[0014]

[Table 2]

[0015]

[Table 3]

[0016]

[Table 4]

[0017]

[Table 5]

[0018]

[Table 6]

[0019]

[Table 7]

[0020]

[Table 8] [In Tables 1 to 8, Me is a methyl group, Et is an ethyl group, n-Pr is a propyl group, i-Pr is an isopropyl group, n-Bu is a butyl group, and t-Bu is tert-
A butyl group, Am is an amyl group, Bz is a benzyl group,
Ph represents a phenyl group, Py represents a pyridyl group, c represents cyclo, and sec represents secondary. ]

The compound of the present invention obtained as described above can be reacted in the presence of an acid to produce an oxime ether compound represented by the general formula (4) (hereinafter, the compound of the present invention). Step 2). In the reaction, methanol may be removed from the reaction system in some cases for the purpose of shortening the reaction time. Specifically, any one of the following methods or a method using them in combination is used. 1) Methanol is distilled out of the reaction system under normal pressure or reduced pressure conditions. 2) Coexist with a reagent (eg, acid anhydride, acid halide, etc.) that reacts with methanol under the reaction conditions of the reaction. The reaction can be performed without a solvent or in a solvent.
The reaction temperature of the reaction is usually in the range of 50 to 200 ° C, and the reaction time is usually in the range of 1 to 20 hours. The amount of the reagent used for the reaction is in the range of 0.0001 to 10 mol of the acid based on 1 mol of the compound of the present invention. Examples of the acid used include minerals such as hydrochloric acid, sulfuric acid, nitric acid, boric acid, phosphoric acid, and polyphosphoric acid; carboxylic acids such as acetic acid, trifluoroacetic acid, oxalic acid, and benzoic acid; chlorosulfonic acid, tosylic acid, and camphorsulfonic acid; Sulfonic acids such as methanesulfonic acid and trifluoromethanesulfonic acid; and Lewis acids such as zinc chloride, boron trifluoride diethyl ether complex, and trimethylsilyl chloride. Examples of the solvent include 1,4-dioxane, tetrahydrofuran,
Ether solvents such as ethylene glycol dimethyl ether, diethylene glycol dimethyl ether and tert-butyl methyl ether; aliphatic hydrocarbon solvents such as hexane, heptane, ligroin and petroleum ether; aromatic hydrocarbon solvents such as toluene and xylene; chloroform; , 2-dichloroethane, carbon tetrachloride, monochlorobenzene and other halogenated hydrocarbon solvents, ethyl formate,
Examples include ester solvents such as butyl acetate, ethyl acetate and diethyl carbonate, nitro compound solvents such as nitroethane and nitrobenzene, nitrile solvents such as acetonitrile and isobutyronitrile, and mixtures thereof. When a reagent reacting with methanol is used, the amount of the reagent used is in the range of 1 to 10 mol per 1 mol of the compound of the present invention. Examples of the acid halide of the reagent used to react with methanol include acetyl chloride and methanesulfonyl chloride. Examples of the acid anhydride include acetic anhydride and methanesulfonic anhydride.
After completion of the reaction, the reaction solution is neutralized and concentrated with a base, if necessary, diluted with an organic solvent, and the solution is washed with water.
By performing post-treatment such as concentration, the desired oxime ether compound represented by the above general formula (4) can be obtained. The compound can be purified by recrystallization, chromatography or the like.

Next, the oxime ether compounds represented by the general formula 4 obtained by the production step 2 of the present invention are shown in Tables 9 to 16, but the present invention is not limited to these.

Embedded image A compound represented by the formula:

[0023]

[Table 9]

[0024]

[Table 10]

[0025]

[Table 11]

[0026]

[Table 12]

[0027]

[Table 13]

[0028]

[Table 14]

[0029]

[Table 15]

[0030]

[Table 16] [In Tables 9 to 16, Me represents a methyl group, Et represents an ethyl group, n-Pr represents a propyl group, i-Pr represents an isopropyl group, n-Bu represents a butyl group, and t-Bu represents tert.
-Butyl group, Am represents an amyl group, Bz represents a benzyl group, Ph group represents a phenyl group, Py represents a pyridyl group, c represents cyclo, and sec represents secondary. ]

When the oxime ether compound represented by the general formula (4) is used as an active ingredient of an agricultural and horticultural fungicide, it may be used as it is without adding any other components.
Usually, it is mixed with a solid carrier, a liquid carrier, a surfactant, and other auxiliaries for formulation and formulated into emulsions, wettable powders, suspensions, powders, granules and the like. In these preparations, an oxime ether compound represented by the general formula 4 is used as an active ingredient.
Usually 0.1 to 99.9% by weight, preferably 1 to 9
It contains 0%. Examples of the solid carrier used in the preparation include, for example, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corn cob powder, walnut shell powder, urea, Examples of the liquid carrier include fine powders or granular substances such as ammonium sulfate and synthetic hydrous silicon oxide. Examples of the liquid carrier include aromatic hydrocarbons such as xylene and methylnaphthalene, and alcohols such as isopropanol, ethylene glycol and cellosolve. And ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethylsulfoxide, acetonitrile, water and the like. Examples of the surfactant include anions such as alkyl sulfate, alkyl (aryl) sulfonate, dialkyl sulfosuccinate, polyoxyethylene alkyl aryl ether phosphate, and naphthalenesulfonic acid formalin condensate. Examples of the surfactant include nonionic surfactants such as surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkyl polyoxypropylene block copolymers, and sorbitan fatty acid esters. Pharmaceutical adjuvants include, for example, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PA
P (acidic isopropyl phosphate) and the like. Examples of the method of applying the oxime ether compound represented by the general formula 4 include foliage application, soil treatment, seed disinfection, and the like. Further, any method commonly used by those skilled in the art can be used. Can be used.

When the oxime ether compound represented by the general formula (4) is used as an active ingredient of an agricultural and horticultural fungicide,
The application rate of the active ingredient depends on the type of the target plant (crop etc.),
It may vary depending on the type of the target disease, the degree of occurrence of the disease, the form of the preparation, the method of application, the time of application, the weather conditions, etc., but it is usually 0.01 to 50 g per arc, preferably 0.05 to 50 g.
10 g. When the emulsion, wettable powder, suspending agent and the like are diluted with water and applied, the application concentration is 0.0001 to 0.1.
It is 5%, preferably 0.0005 to 0.2%, and dusts, granules and the like are applied without dilution.

The oxime ether compound represented by the general formula (4) can be used as an agricultural and horticultural fungicide for fields, paddy fields, orchards, tea fields, pastures, turf, etc., and other agricultural and horticultural fungicides. By mixing and using, it can be expected that the sterilization effect is also enhanced. Other agricultural and horticultural fungicides that can be mixed include, for example, propiconazole, triadimenol.
, Prochloraz, penconazole, tebuconazole,
Flusilazole, diniconazole, bromconazole,
Epoxyconazole, difenoconazole, cyproconazole, metconazole, triflumizole, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole, triticonazole (RPA400727), bitertanol , Fungicides such as imazalil and furtriahole, bacteric compounds such as fenpropimorph, tridemorph and fenpropidine, and benzimidazoles such as carbendazim, benomyl, thiabendazole and thiophanate methyl. Fungicide, procymidone, cyprodinil, pyrimethanil, dietofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonil, Rujiokisoniru, dichlofluanid, folpet, kresoxim-methyl (or methyl methoxyimino-.alpha.-(o-tolyloxy) -o
-Tolyl acetate or BAS490F), azoxystrobin (or methyl (E)-{2- [6-
(2-cyanophenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate or I
CIA5504), N-methyl-α-methoxyimino-
2-[(2,5-dimethylphenoxy) methyl] phenylacetamide and the like. Further, it can be mixed or used in combination with an insecticide, acaricide, a nematicide, a herbicide, a plant growth regulator, and a fertilizer.

Plant diseases which can be controlled by the oxime ether compound represented by the general formula (4) include, for example, the following diseases. Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliob)
olus miyabeanus), sheath blight (Rhizoctonia solani), wheat powdery mildew (Erysiphe graminis), red mold (Gi)
bberella zeae), rust (Puccinia striiformis, P.
graminis, P. recondita, P. hordei), snow rot (Typhul
a sp., Micronectriella nivalis), naked smut (Ustilago
tritici, U. nuda), Black smut (Tilletia carie)
s), eye spot disease (Pseudocercosporella herpotrichoides),
Scratches (Rhynchosporium secalis), leaf blight (Septoria)
tritici), wilt (Leptosphaeria nodorum), citrus black spot (Diaporthe citri), scab (Elsinoe)
fawcetti), fruit rot (Penicillium digitatum, P.
italicum), Monilia disease of apple (Sclerotinia mali)
, Rot (Valsa mali), powdery mildew (Podosphaera)
leucotricha), spot leaf spot (Alternaria mali), scab (Venturia inaequalis), pear scab (Venturia n
ashicola, V. pirina), black spot (Alternaria kikuchian)
a), scab (Gymnosporangium haraeanum), peach scab (Sclerotinia cinerea), scab (Cladosporium car
pophilum), Phomopsis sp., grape black rot (Elsinoe ampelina), late rot (Glomer)
ella cingulata), powdery mildew (Uncinula necator),
Rust (Phakopsora ampelopsidis), Blacklot disease (Guignardia bidwellii), Downy mildew (Plasmopara vitic)
ola), oyster anthracnose (Gloeosporium kaki), deciduous disease (Ce
rcospora kaki, Mycosphaerella nawae), cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaer
otheca fuliginea), vine blight (Mycosphaerella melon)
is), vine disease (Fusarium oxysporum), downy mildew (Pseu
doperonospora cubensis), plague (Phytophthora sp.)
, Seedling blight (Pythium sp.), Tomato ring spot (Alterna
ria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), eggplant brown spot (Phomopsi)
s vexans), powdery mildew (Erysiphe cichoracearum),
Black spot (Alternaria japonica), white spot (Cercosporella brassicae), and onion rust (Puccin) on cruciferous vegetables
ia allii), soybean purpura (Cercospora kikuchii),
Black spot (Elsinoe glycines), black spot (Diaporthe ph)
aseolorum var. sojae), bean anthracnose (Colletot)
richum lindemthianum), peanut black rot (Cercos
pora personata), brown spot (Cercospora arachidicol)
a), pea powdery mildew (Erysiphe pisi), potato summer blight (Alternaria solani), blight (Phytophthora)
infestans), strawberry powdery mildew (Sphaerotheca hum)
uli), tea leaf rot (Exobasidium reticulatum), white scab (Elsinoe leucospila), tobacco scab (Altern)
aria longipes), powdery mildew (Erysiphe cichoracearu)
m), Anthracnose (Colletotrichum tabacum), Downy mildew (Per
onospora tabacina), plague (Phytophthora nicotiana)
e), sugar beet brown spot (Cercospora beticola), rose scab (Diplocarpon rosae), powdery mildew (Sphaerothe
ca pannosa), chrysanthemum rot of chrysanthemum (Septoria chrysanthemi-
indici), white rust (Puccinia horiana), gray mold on various crops (Botrytis cinerea), sclerotium (Scleroti)
nia sclerotiorum) and the like.

[0035]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, which should not be construed as limiting the present invention. The compounds are indicated by the numbers in Tables 1 to 8.

Production Example 1 (Example of Production Process 1 of the Invention for Producing Compound 2 of the Invention) Methyl 2- {2-methyl-5- (1-benzyloxyiminoethyl) phenoxy} -3-hydroxyacrylate 25 g (70 mmol) ), 0.10 g (0.5 mmol) of p-toluenesulfonic acid monohydrate, 80 ml (730 mmol) of trimethyl orthoformate and 150 ml (3706 mmol) of methyl alcohol were heated and stirred at the solvent reflux temperature for 3 hours. Thereafter, the reaction solution was allowed to cool, 1 ml of triethylamine was added, and the mixture was concentrated. The residue was diluted with 500 ml of ethyl acetate and washed three times with water. The organic layer was dried over magnesium sulfate and concentrated, and the target methyl 2- {2-methyl-5-
(1-benzyloxyiminoethyl) phenoxy｝-
3,3-dimethoxypropionic acid (the present compound 82)
26 g (65 mmol) were obtained. Yield 93% ¹ H-NMR (TMS, CDCl ₃ ) δ / ppm 7.2-7.5 (5H), 7.16 (1H, s), 7.13 (2H, dAB), 5.21 (2H, s), 4.
79 (1H, d, J = 5.9Hz), 4.72 (1H, d, J = 5.9Hz), 3.74 (3H, s), 3.5
0 (3H, s), 3.48 (3H, s), 2.29 (3H, s), 2.20 (3H, s)

Preparation Example 2 (Example of Preparation Step 2 of the Present Invention Using Compound 2 of the Present Invention) Methyl 2- {2-methyl-5- (1-benzyloxyiminoethyl) phenoxy} -3,3-dimethoxypropionic acid 2.0 g (5.0 mmol), methanesulfonic acid 0.02 ml (0.3 mmol), acetic anhydride 0.52
ml (5.5 mmol) and 15 ml of toluene were heated and stirred at the solvent reflux temperature for 5 hours. Thereafter, the reaction solution was diluted with 50 ml of ethyl acetate, and washed three times with saturated aqueous sodium hydrogen carbonate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (developing solvent: hexane: ethyl acetate = 9: 1) to give the desired methyl 2- {2-methyl-5
-(1-benzyloxyiminoethyl) phenoxy}-
1.3 g (3.5 mmol) of 3-methoxy acrylate
I got Yield 70% ¹ H-NMR (TMS, CDCl ₃ ) δ / ppm 7.0-7.45 (9H, m), 5.20 (2H, s), 3.85 (3H, s), 3.70 (3H, s), 2.
35 (3H, s), 2.19 (3H, s)

Next, the method of synthesizing the raw materials used in the production step 1 of the present invention will be described in more detail by reference production examples. Reference Production Example Potassium hydride (35% oil dispersion) 22
A mixture of 5.0 g (1.963 mol) and 1,2-dimethoxyethane (1,500 ml) was stirred in an argon atmosphere at 10 ° C. or less under ice cooling with methyl 2- {5- (1).
-Benzyloxyiminoethyl) -2-methylphenoxydiacetate 347.4 g (1.061 mol), methyl formate 510.0 g (8.490 mol) and 1,
A solution consisting of 500 ml of 2-dimethoxyethane was added dropwise. After dropping, the temperature was raised to room temperature, and stirring was continued at room temperature for 4 hours. Thereafter, 500 ml of water was added dropwise to the reaction solution, and this was further poured into a mixture of 1.5 kg of ice and 4.5 L of water. The obtained mixture was washed with 3 L of methyl tertiary butyl ether, the aqueous layer was separated, and the pH was adjusted to 2 by dropwise addition of concentrated hydrochloric acid. The precipitated target substance was extracted twice with 3 L of methyl tertiary butyl ether, and the ether layers were collected, washed with water and saturated saline in that order, dried over magnesium sulfate, filtered and concentrated to obtain the target methyl 2
-{2-methyl-5- (1-benzyloxyiminoethyl) phenoxy} -3-hydroxyacrylate 31
0.0 g (0.8723 mol) was obtained. Yield 82% ¹ H-NMR (TMS, CDCl ₃ ) δ (ppm): 7.52 (1H, s), 7.2-7.5 (5H), 7.11 (2H, s), 6.88 (1H,
s), 5.21 (2H, s), 3.66 (3H, s), 2.33 (3H, s), 2.13 (3H, s)

Next, reference examples of the oxime ether compound represented by the general formula (4) are shown. The parts are by weight, and the compounds are indicated by the numbers in Tables 9 to 16. Reference Formulation Example 1 50 parts of each of Compounds 2-1 to 2-200, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed to obtain each wettable powder. obtain. Reference Formulation Example 2 25 parts of each of compounds 2-1 to 2-200, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed until the particle size of the active ingredient becomes 5 microns or less. Each suspension is obtained by wet grinding. Reference Formulation Example 3 2 parts each of Compounds 2-1 to 2-200, kaolin cream
88 parts and 10 parts of talc are well pulverized and mixed to obtain each powder. Reference Formulation Example 4 20 parts of each of Compounds 2-1 to 2-200, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 60 parts of xylene were mixed well to prepare each emulsion. obtain. Reference Formulation Example 5 2 parts of each of Compounds 2-1 to 2-200, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly pulverized and mixed, and water is added. After kneading, each granule is obtained by granulation and drying.

Reference Formulation Example 6 20 parts of each of compounds 2-1 to 2-200 and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol, and finely mixed with a sand grinder. After pulverization (particle size 3μ or less), xanthan gum
0.05 parts and aluminum magnesium silicate 0.1
Then, 40 parts of an aqueous solution containing 10 parts of propylene glycol are added, and 10 parts of propylene glycol are further added, followed by stirring and mixing to obtain a 20% suspension in water. Reference Formulation Example 7 0.1 part of each of Compounds 2-1 to 2-200 was dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this was deodorized kerosene.
Mix with 89.9 parts to obtain 0.1% oil for each. Reference Formulation Example 8 0.1 part of each of compounds 2-1 to 2-200, 0.2 part of tetramethrin, 0.1 part of d-phenothrin, 10 parts of trichloroethane and 59.6 parts of deodorized kerosene were mixed and dissolved, and the mixture was filled in an aerosol container, and the valve portion was filled. Then, 30 parts of a propellant (liquefied petroleum gas) is charged under pressure through the valve portion to obtain each oily aerosol. Reference Preparation Example 9 0.2 parts of each of Compounds 2-1 to 2-200, 0.2 part of d-aresulin, 0.2 part of d-phenothrin, 5 parts of xylene, 3.4 parts of deodorized kerosene, and emulsifier @Atmos 300 (registered trademark of Atlas Chemical Company) ｝ 1 part mixed and dissolved,
50 parts of pure water is charged into an aerosol container, a valve is attached, and 40 parts of a propellant (liquefied petroleum gas) is charged under pressure through the valve to obtain each aqueous aerosol. Reference Formulation Example 10 0.3 g of each of Compounds 2-1 to 2-200 was added with 0.3 g of d-allethrin, dissolved in 20 ml of acetone, and a carrier for mosquito coil (tab flour: lees flour: wood flour 4: 3: 3)
After uniformly stirring and mixing with 99.4 g, 120 ml of water was added, and the mixture was sufficiently kneaded and dried to obtain each mosquito coil.

Reference Formulation Example 11 Acetone was added to 0.4 g of each of Compounds 2-1 to 2-200, 0.4 g of d-arlesrin and 0.4 g of pipenylbutoxide, and dissolved to make 10 ml with total. This solution 0.
5 ml of a 2.5 cm × 1.5 cm, 0.3 cm thick base for electric mat (a fibril of a mixture of cotton syringe and pulp solidified into a plate) is evenly impregnated with each electric mosquito. Get a mat. Reference Formulation Example 12 100 mg of each of Compounds 2-1 to 2-200 is dissolved in an appropriate amount of acetone, and impregnated into a porous ceramic plate having a size of 4.0 cm × 4.0 cm and a thickness of 1.2 cm to obtain each of the heated smokers. Reference Formulation Example 13 10 mg of each of Compounds 2-1 to 2-200 was added to acetone 0.5
The resulting solution is treated with 5 g of a solid feed powder for animals (solid feed powder for breeding and breeding, CE-2, trade name of Nippon Clea Co., Ltd.) and uniformly mixed. The acetone is then air-dried to obtain each 0.5% bait.

Next, test examples show that the oxime ether compound represented by the general formula (4) is useful as an agricultural and horticultural fungicide. The compounds are indicated by the numbers in Tables 9 to 16. The controlling effect of the oxime ether compound represented by the general formula 4 was evaluated by visually observing the area ratio of lesions on the test plant at the time of the investigation. (The area ratio is a percentage of the area of the lesion in the treated section relative to the area of the lesion in the untreated section.)

Reference Test Example 1: Rice Blast Control Test (Preventive Effect) A plastic pot was filled with sandy loam, rice (Nipponbare) was sown, and grown in a greenhouse for 20 days. Then, compound 2
-1, 2-2, 2-3, 2-82, 2-83, 2-8
5, 2-91, 2-94, 2-95, 2-99, 2-1
00, 2-102, 2-104, 2-107, 2-11
0, 2-111, 2-114, 2-116, 2-11
9, 2-120, 2-122, 2-123, 2-12
5, 2-129, 2-134, 2-136, 2-13
7, 2-140, 2-146, 2-156, 2-17
7, 2-180, 2-181, 2-182, 2-18
4, 2-185, 2-186, 2-193, 2-19
6, 2-197, 2-198, and 2-199 were prepared as wettable powders according to Reference Formulation Example 1, and then diluted with water to a predetermined concentration (500 or 200 ppm). Foliage was sprayed so as to sufficiently adhere to the leaves. After spraying, the plants were air-dried and sprayed with a suspension of the blast fungus. 28 ° C after inoculation,
After 6 days in humid conditions, the control effect was investigated. As a result, all the compounds suppressed the occurrence of blast to an area ratio of 30% or less.

Reference Test Example 2: Wheat Leaf Rust Control Test (Preventive Effect) A plastic pot was filled with sandy loam, and wheat (Agriculture and Forestry 73)
No. 2) and grown in a greenhouse for 10 days. Compound 2-
82, 2-83, 2-85, 2-91, 2-95, 2-
99, 2-100, 2-102, 2-104, 2-10
7, 2-110, 2-111, 2-114, 2-11
6, 2-119, 2-120, 2-122, 2-12
3, 2-125, 2-129, 2-134, 2-13
6, 2-137, 2-140, 2-146, 2-15
6, 2-180, 2-181, 2-182, 2-18
4, 2-185, 2-186, 2-193, 2-19
6, 2-197, 2-198, and 2-199 were made into an emulsion in accordance with Reference Formulation Example 4, and then diluted with water to a predetermined concentration.
(500 or 200 ppm), which was sprayed with foliage so as to adhere well to the wheat leaf surface. After spraying, air-dry the plants,
Spores of wheat rust fungus were inoculated. 23 after inoculation
C., 1 day under dark and humid, and further 6 days under illumination, and the control effect was investigated. As a result, all compounds
The incidence of leaf rust was suppressed to 30% or less.

Reference Test Example 3: Test for controlling cucumber powdery mildew (preventive effect) A plastic pot was filled with sandy loam, cucumber (Sagami Hanjiro) was sown, and grown in a greenhouse for 12 days. Compound 2-
1, 2-2, 2-3, 2-82, 2-83, 2-85,
2-99, 2-100, 2-102, 2-104, 2-
107, 2-110, 2-111, 2-114, 2-1
16, 2-119, 2-120, 2-122, 2-12
3, 2-125, 2-129, 2-134, 2-13
6, 2-137, 2-140, 2-146, 2-15
6, 2-177, 2-180, 2-181, 2-18
2, 2-184, 2-185, 2-186, 2-19
3, 2-196, 2-197, 2-198, 2-199
Was prepared as a suspension in accordance with Reference Formulation Example 2 and diluted with water to a predetermined concentration (500 or 200 ppm), which was sprayed on the foliage so as to sufficiently adhere to the cucumber leaves. After spraying, the plants were air-dried and inoculated with spores of cucumber powdery mildew. After 12 days at 23 ° C after inoculation, the control effect was investigated. As a result, all the compounds suppressed the onset of cucumber powdery mildew to an area ratio of 30% or less.

Reference Test Example 4: Test for controlling the effect of grape downy mildew (preventive effect)
A) were sown and grown in a greenhouse for 40 days. Compound 2-
82, 2-83, 2-85, 2-91, 2-99, 2-
100, 2-102, 2-104, 2-107, 2-1
10, 2-111, 2-114, 2-116, 2-11
9, 2-120, 2-122, 2-123, 2-12
5, 2-129, 2-134, 2-136, 2-13
7, 2-140, 2-146, 2-156, 2-18
0, 2-181, 2-182, 2-184, 2-18
5, 2-186, 2-193, 2-196, 2-199
Was prepared as a suspension in accordance with Reference Formulation Example 2, diluted with water to a predetermined concentration (500 or 200 ppm), and sprayed with foliage so as to sufficiently adhere to the grape leaf surface. After spraying, the plants were air-dried and spray-inoculated with a zoosporangial suspension of grape downy mildew. After the inoculation, they were first placed in a humid environment at 23 ° C. for 1 day, and further placed in a greenhouse for 6 days. As a result, all compounds reduced the incidence of grape downy mildew by an area ratio of 30.
%.

[0047]

According to the present invention, the oxime ether represented by the above general formula (4) can be easily produced.

 ────────────────────────────────────────────────── ─── Continued on the front page F term (reference) 4C055 AA01 BA01 BA02 BA08 BA16 BA39 BA42 BB02 CA01 CA02 CA06 CA13 CA16 CA39 CB02 DA01 DA06 DA16 DB02 FA01 FA32 FA37 4H006 AA01 AB84 AC13 AC43 BA66 BW21 BW31 BW33

Claims (9)

[Claims] 1. A compound represented by the general formula: [In the formula, R ¹ is an optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted Cycloalkylalkyl group,
An optionally substituted cycloalkenyl group, an optionally substituted cycloalkenylalkyl group, an optionally substituted aryl group, an optionally substituted arylalkyl group, an optionally substituted heteroaryl group or Represents an optionally substituted heteroarylalkyl group, R ² represents an alkyl group, a cycloalkyl group, an alkoxyalkyl group, a haloalkyl group or a cyano group,
One of T, U and V represents a CR ³ group, the other represents a CH group or a nitrogen atom, and the other represents a CR ³ group.
Represents ⁴ groups or a nitrogen atom. W represents a CR ³³ group or a nitrogen atom, wherein R ³ , R ⁴ and R ³³ are the same or different and are a hydrogen atom, a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylthio group or Represents a haloalkylthio group. ｝. ] The compound shown by these. 2. The compound represented by the above general formula 1 wherein R ¹ is a halogen atom or an OR ⁸ group [where R ⁸ is C 1
-C10 alkyl group, C1-C5 haloalkyl group, C3
Represents a C6 cycloalkyl group or a phenyl group (the phenyl group may be substituted with a halogen atom, a C1 to C5 alkyl group or a trifluoromethyl group). ],
C (R ¹³ ) = NOR ¹⁴ group [where R ¹³ and R ¹⁴ are the same or different and are a hydrogen atom, a C1-C10 alkyl group, a C3-C6 cycloalkyl group or a phenyl group (the phenyl group is a halogen atom, C1-C5 alkyl group, trifluoromethyl group or cyano group). ], A C1-C5 alkylthio group, C1
-C5 haloalkylthio group, C1-C10 acyl group, C
2-C11 alkoxycarbonyl group, N- (C1-C1
0 alkyl) carbamoyl group, N, N-di (C1-C1
0 alkyl) carbamoyl group, cyano group, aryl group [the aryl group is a halogen atom, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 haloalkyl group, a C1-C10 alkoxy group, a C1 -C5 haloalkoxy group, cyano group, C5-C8 cycloalkoxy group, C1-C10 acyl group, phenoxy group (the phenoxy group is a halogen atom, a C1-C3 alkyl group, a C1-
A C3 haloalkyl group or a C1-C3 alkylthio group, which may be substituted, a phenyl group, which may be substituted with a cyano group, a 2-pyridyloxy group (the 2-pyridyloxy group is a trifluoromethyl group or a halogen atom; Or a benzyloxy group or a benzoyloxy group. And a heteroaryl group wherein the heteroaryl group is a halogen atom, a C1-C10 alkyl group, a C3-C10 cycloalkyl group, a C1-C5 haloalkyl group, a C1-C10
It may be substituted with an alkoxy group or a C1-C10 alkylthio group. The compound according to claim 1, which is any group selected from the following group which may be substituted with one or more groups selected from the group consisting of: (Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, cycloalkenylalkyl group, aryl group, arylalkyl group,
Heteroaryl group and heteroarylalkyl group] 3. The compound represented by the above general formula 1, wherein R ¹ is an optionally substituted C1-C10 alkyl group, an optionally substituted C2-C10 alkenyl group,
C2-C10 alkynyl group which may be substituted, C3-C10 cycloalkyl group which may be substituted, C4-C20 cycloalkylalkyl group which may be substituted, C5-C10 cycloalkenyl which may be substituted Group, an optionally substituted C6-C20 cycloalkenylalkyl group, an optionally substituted C6-C10 aryl group, an optionally substituted C7-C20 arylalkyl group, an optionally substituted C1-C9 A heteroaryl group or an optionally substituted C2 to C19 heteroarylalkyl group, wherein R ² is a hydrogen atom,
C10 alkyl group, C3-C10 cycloalkyl group, C
A 2-C10 alkoxyalkyl group, a C1-C5 haloalkyl group or a cyano group, wherein R ³ , R ⁴ and R ³³ are the same or different and are a hydrogen atom, a halogen atom,
C10 alkyl group, C1-C10 alkoxy group, C1-
The compound according to claim 1, which is a C10 haloalkyl group, a C1 to C10 haloalkoxy group, a C1 to C10 alkylthio group or a C1 to C10 haloalkylthio group. 4. A compound represented by the above general formula 1 wherein R ¹ is a halogen atom or an OR ⁸¹ group wherein R ⁸¹ is
A 1-C5 alkyl group or a C2-C5 alkoxyalkyl group or a phenyl group (the phenyl group is a halogen atom,
A C1-C5 alkyl group or a trifluoromethyl group). ], C (R ⁶³ ) = NO
R ⁶⁴ groups [where R ⁶³ and R ⁶⁴ are the same or different and each represent a hydrogen atom, a C1-C10 alkyl group, a C3-C6 cycloalkyl group or a phenyl group (the phenyl group is a halogen atom, a C1-C5 alkyl group; Which may be substituted with a trifluoromethyl group or a cyano group). ], A C1-C5 alkylthio group, a C1-C5 acyl group, a cyano group, an aryl group [the aryl group is a halogen atom, a C1-C5 alkyl group, a C3-C6 cycloalkyl group, a C1-C5 haloalkyl group or a C1 It may be substituted with a -C5 alkoxy group. ] And a heteroaryl group [the heteroaryl group is a halogen atom,
5-alkyl group, C3-C6 cycloalkyl group, C1-C
5-haloalkyl group, C1-C5 alkoxy group or C1
It may be substituted with a -C5 alkylthio group. 3. The compound according to claim 1, which is any group selected from the following group which may be substituted with one or more groups selected from the group consisting of: [Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, cycloalkenylalkyl group, aryl group, arylalkyl group, heteroaryl group and heteroarylalkyl group] 5. An aryl group in a compound represented by the general formula 1 is a phenyl group, an α-naphthyl group or a β-naphthyl group, and a heteroaryl group is a 2-pyridyl group, a 4-pyridyl group or a 2-pyridyl group. Pyrimidinyl group, 4-pyrimidinyl group, 3-pyrazolyl group, 2-thiazolyl group, 2-
The compound according to any one of claims 1 to 4, which is an imidazolyl group or a 3- (1,2,4-triazolyl) group. 6. A compound represented by the general formula:
One of T, U and V is a CR ³ group, the other is a CH group, and the other is a CR ⁴ group,
There CR ^{3 3} group (R ^3, R ⁴ and R ^33. Represent the same meanings as described above) A compound according to any one of claims 1 to 5 is. 7. A compound of the general formula [Wherein, R ¹ , R ² , V, U, T and W represent the same meaning as described above. The method for producing a compound represented by the general formula (1) according to claim 1, wherein the compound represented by the general formula (1) is reacted with methanol in the presence of an acid. 8. A compound represented by the general formula 1 wherein the compound represented by the general formula 1 is reacted in the presence of an acid. [Wherein, R ¹ , R ² , V, U, T and W represent the same meaning as described above. ] The process for producing an oxime ether compound represented by the formula: 9. An oxime represented by the general formula 3, wherein the compound represented by the general formula 1 according to claim 1 is reacted with an acid in the presence of an acid anhydride or an acid halide. A method for producing an ether compound.