JP2000103773A - Acrylic acid derivatives and their uses - Google Patents

Abstract

(57) [Problem] To provide a compound having excellent agricultural and horticultural bactericidal efficacy. SOLUTION: General formula 1 [Wherein, R ¹ represents an A ¹ -ON = CA ² -group or the like.] Here, A ¹ and A ² are the same or different, and represent an optionally substituted alkyl group or the like. ｝, R ² represents a fluoromethyl group or a difluoromethyl group, R ³ represents an alkyl group, one of T, U and V represents a CR ⁴ group, and the other represents a CH group or a nitrogen atom. And the other one represents a CR ⁵ group or a nitrogen atom, W represents a CR ⁴⁴ group or a nitrogen atom. Here, R ⁴ , R ⁵ and R ⁴⁴ are the same or different and represent a hydrogen atom or the like. . ｝, X represents an NR ⁶ group, an oxygen atom or a sulfur atom. ｛Wherein R ⁶ represents an alkyl group. ｝. An acrylic acid derivative represented by the formula:

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

[0001] The present invention relates to an acrylic acid derivative and its use.

[0002]

An object of the present invention is to provide a compound having an excellent germicidal activity for agriculture and horticulture.

[0003]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that acrylic acid derivatives represented by the following general formula (2) have excellent agricultural and horticultural bactericidal efficacy, and have reached the present invention.

That is, the present invention provides a compound represented by the following general formula:

Embedded image [Wherein, R ¹ is an A ¹ -ON = CA ² -group, A ¹ SC
(A ² ) = N-group or A ¹ SC (SA ² ) = N-group, wherein A ¹ and A ² are the same or different, and may be an optionally substituted alkyl group, Good alkenyl group, optionally substituted alkynyl group, optionally substituted cycloalkyl group, optionally substituted cycloalkylalkyl group, optionally substituted cycloalkenyl group, optionally substituted Represents a cycloalkenylalkyl group, an optionally substituted aryl group, an optionally substituted arylalkyl group, an optionally substituted heteroaryl group or an optionally substituted heteroarylalkyl group. ｝, R ² represents a fluoromethyl group or a difluoromethyl group, R ³ represents an optionally substituted alkyl group, one of T, U and V represents a CR ⁴ group, and the other Represents a CH group or a nitrogen atom, the other represents a CR ⁵ group or a nitrogen atom, W represents a CR ⁴⁴ group or a nitrogen atom, wherein R ⁴ , R ⁵ and R ⁴⁴ are the same or different , Hydrogen atom,
Represents a halogen atom, an alkyl group, an alkoxy group, a haloalkyl group, a haloalkoxy group, a cyano group, a nitro group, an alkoxycarbonyl group, an alkylthio group or a haloalkylthio group. ｝, X represents an NR ⁶ group, an oxygen atom or a sulfur atom. ｛Wherein R ⁶ represents an alkyl group. ｝. And a fungicide for agricultural and horticultural use containing the same as an active ingredient.

[0005]

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 A ¹ and A ² include, for example, methyl, ethyl, propyl, isopropyl, butyl, 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 group such as dimethyl octyl group and the like, the alkenyl group in the optionally substituted alkenyl group represented by A ¹ and A ^2, for example, vinyl group, allyl group, 1-methyl-2- Propenyl group, 2-
Methyl-2-propenyl, 2-butenyl, 2-pentenyl, 3-methyl-2-butenyl, etc. C2~C10 alkenyl groups such as geranyl group and the like, A ¹ and A ²
Examples of the alkynyl group in the optionally substituted alkynyl group represented by are, for example, an ethynyl group, a propargyl group, a 1-methyl-2-propynyl group, a 3-methyl-2
And C2 to C10 alkynyl groups such as a propynyl group. The cycloalkyl group in the optionally substituted cycloalkyl group represented by A ¹ and A ² includes, for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like. And C3 to C10 cycloalkyl groups, and the like,
The cycloalkyl group in the optionally substituted cycloalkyl group represented by A ¹ and A ^2, for example, cyclopropylmethyl group, cyclopentylmethyl group, 2-cyclopentylethyl group, C4-C20 such as a cyclohexylmethyl group Examples of the cycloalkenyl group in the optionally substituted cycloalkenyl group represented by A ¹ and A ² include, for example, a C5-C10 cycloalkenyl group such as a cyclopentenyl group and a cyclohexenyl group. Is raised,
Examples of the cycloalkenyl group in the optionally substituted cycloalkenylalkyl group represented by A ¹ and A ² include C6-C20 cycloalkenylalkyl groups such as cyclopenten-1-ylmethyl group and cyclohexen-1-ylmethyl group. Examples of the aryl group in the optionally substituted aryl group represented by A ¹ and A ² include a C6-C10 aryl group such as a phenyl group, an α-naphthyl group and a β-naphthyl group. Examples of the arylalkyl group in the optionally substituted arylalkyl group represented by A ¹ and A ² include a phenylmethyl group, a 2-phenylethyl group and a 3-phenyl-
C7-C2 such as n-propyl group, 4-phenyl-n-butyl group, α-naphthylmethyl group, β-naphthylmethyl group
And a substituted or unsubstituted heteroaryl group represented by A ¹ and A ² is, for example, a 2-pyridyl group or a 4-pyridyl group.
Pyridyl group, 2-pyrimidinyl group, 4-pyrimidinyl group, 3-pyrazolyl group, 2-thiazolyl group, 2-imidazolyl group, 3- (1,2,4-triazolyl) group, 2-
C1~C9 heteroaryl group such as a quinolinyl group, and examples of the heteroarylalkyl group in the optionally substituted heteroarylalkyl group represented by A ¹ and A ^2, for example, 2-pyridylmethyl group, 4-pyridyl Methyl group, 2-pyrimidinylmethyl group, 4-pyrimidinylmethyl group, 3-pyrazolylmethyl group, 2-thiazolylmethyl group, 2-imidazolylmethyl group, 3- (1,2,2
C2-C19 heteroarylalkyl groups such as 4-triazolyl) methyl group and 2-quinolinylmethyl group;

[0006] An optionally substituted alkyl group, an optionally substituted alkenyl group, an optionally substituted alkynyl group, an optionally substituted cycloalkyl group, a substituted or unsubstituted alkyl group represented by A ¹ or A ² A cycloalkylalkyl group, a cycloalkenyl group which may be substituted, a cycloalkenylalkyl group which may be substituted, an aryl group which may be substituted, an arylalkyl group which may be substituted, Examples of the substituent of the heteroaryl group which may be substituted or the heteroarylalkyl group which may be substituted include a halogen atom (a chlorine atom, a bromine atom, a fluorine atom, etc.), an alkyl group (e.g., a methyl group, an ethyl group, a propyl group). Group, 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 etc.], haloalkyl group [for example, C1 such as trifluoromethyl group, 2,2,2-trifluoroethyl group, 1,1,2,2-tetrafluoroethyl group and the like]
To C10 haloalkyl group, etc.], cycloalkyl group [for example, C3 to C10 cycloalkyl group such as cyclopropyl group, cyclopentyl group, cyclohexyl group], and alkoxy group [for example, methoxy group, ethoxy group, n-propoxy group, i-propoxy group] , N-butoxy group, sec-butoxy group, i-butoxy group, n-pentyloxy group, etc.
1-C10 alkoxy group], haloalkoxy group [for example, trifluoromethoxy group, difluoromethoxy group, difluorobromomethoxy group, difluorochloromethoxy group, fluoromethoxy group, 2,2,2-trifluoroethoxy group, 1,1, A C1-C10 haloalkoxy group such as a 2,2-tetrafluoroethoxy group], an alkylthio group [for example, a methylthio group, an ethylthio group, an n-propylthio group, an n-butylthio group, an i-butylthio group, a sec-
A C1-C10 alkylthio group such as a butylthio group, an n-pentylthio group, an n-hexylthio group], a haloalkylthio group [for example, a trifluoromethylthio group, a difluoromethylthio group, a difluorobromomethylthio group, a difluorochloromethylthio group, a fluoromethylthio group, ,
2,2-trifluoroethylthio group, 1,1,2,2-
A C1-C10 haloalkylthio group such as a tetrafluoroethylthio group], an alkylamino group [eg, a methylamino group, an ethylamino group, an n-propylamino group, an i-propylamino group, an n-butylamino group, a sec-butylamino C1, C10 alkylamino groups such as i-butylamino group, n-pentylamino group and the like; dialkylamino groups [for example, C2 groups such as dimethylamino group, diethylamino group, methylethylamino group, ethyl-n-propylamino group and the like] To C20 dialkylamino group], alkoxycarbonyl group [methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, n -Pentyloxycarboni Group, C2-C10 alkoxycarbonyl group such as n-hexyloxycarbonyl group], haloalkoxycarbonyl group [C2-C10 haloalkoxycarbonyl group such as 2,2,2-trifluoroethoxycarbonyl group], alkylaminocarbonyl group [For example, a methylaminocarbonyl group, an ethylaminocarbonyl group, an n-propylaminocarbonyl group, an i-propylaminocarbonyl group, an n-butylaminocarbonyl group,
i-butylaminocarbonyl group, sec-butylaminocarbonyl group, n-pentylaminocarbonyl group, n-
A C2 to C10 alkylaminocarbonyl group such as a hexylaminocarbonyl group; a dialkylaminocarbonyl group (for example, a C3 to C10 such as a dimethylaminocarbonyl group, a diethylaminocarbonyl group, a methylethylaminocarbonyl group, and an ethyl-n-propylaminocarbonyl group).
Dialkylaminocarbonyl group), acylamino group (e.g., acetylamino group, propanoylamino group, C2-C10 acylamino group such as n-butanoylamino group),
An alkoxycarbonylamino group [for example, methoxycarbonylamino group, ethoxycarbonylamino group, n-propoxycarbonylamino group, i-propoxycarbonylamino group, n-butoxycarbonylamino group, etc.
C10 alkoxycarbonylamino group], a cyano group and a nitro group.

The alkyl group represented by R ³ includes, for example, a C1 to C5 alkyl group such as a methyl group and an ethyl group. The halogen atom represented by R ⁴ , R ⁵ and R ⁴⁴ includes, for example, a chlorine atom , A bromine atom, a fluorine atom, and the like. Examples of the alkyl group represented by R ⁴ , R ^5, and R ⁴⁴ include a methyl group, an ethyl group, a propyl group, an isopropyl group, a butyl group, an isobutyl group, and 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, etc. C1~C10 alkyl group such as 3,7-dimethyl octyl group and the like, R ^4, R ⁵
And the alkoxy group represented by R ^44, a methoxy group, an ethoxy group, n- propoxy group, i- propoxy, n- butoxy group, sec- butoxy group, i- butoxy group, such as n- pentyloxy group A haloalkyl group represented by R ⁴ , R ⁵ and R ⁴⁴ includes, for example, a trifluoromethyl group,
2,2,2-trifluoroethyl group, 1,1,2,2-
Examples thereof include C1 to C10 haloalkyl groups such as a tetrafluoroethyl group. Examples of the haloalkoxy groups represented by R ⁴ , R ⁵ and R ⁴⁴ include, for example, a trifluoromethoxy group, a difluoromethoxy group, a difluorobromomethoxy group, and a difluorochloro group. Methoxy group, fluoromethoxy group, 2,
Examples thereof include C1-C10 haloalkoxy groups such as 2,2-trifluoroethoxy group and 1,1,2,2-tetrafluoroethoxy group. Examples of the alkoxycarbonyl group represented by R ⁴ , R ⁵ and R ⁴⁴ For example, methoxycarbonyl group, ethoxycarbonyl group, n-propoxycarbonyl group, i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, sec-butoxycarbonyl group, n-pentyloxycarbonyl group, n-
Etc. C2~C10 alkoxycarbonyl groups such as hexyloxy group. Examples of the alkylthio group represented by R ^4, R ⁵ and R ^44, for example, methylthio group, ethylthio group, n- propylthio group, n- butylthio group,
i- butylthio, sec- butylthio, n- pentylthio group, etc. C1~C10 alkylthio group such as n- hexylthio, and examples of the haloalkylthio group represented by R ^4, R ⁵ and R ^44, for example, tri C1 such as fluoromethylthio, difluoromethylthio, difluorobromomethylthio, difluorochloromethylthio, fluoromethylthio, 2,2,2-trifluoroethylthio, 1,1,2,2-tetrafluoroethylthio, etc. To C10 haloalkylthio groups and the like,

The alkyl group represented by R ⁶ includes, for example, a C ¹ -C 10 alkyl group such as a methyl group and an ethyl group. As the 6-membered aromatic ring containing T, U, V and W, for example, a benzene ring Pyridine ring, pyrimidine ring and the like.

The compounds of the present invention may have (E) and (Z) isomers based on a CＮN bond and a C ＝ C bond, each of which and a mixture thereof are included in 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 can be produced, for example, according to a synthetic scheme shown in the following scheme 3.

Embedded image [Wherein, R ¹ , R ² , R ³ , T, U, V, W and X represent the same meaning as described above, and L ¹ represents a leaving group such as a halogen atom (eg, a chlorine atom, a bromine atom, etc.). Represent. ]

In step 3, compound [I] and compound [II]
And the reaction in a solvent in the presence of a base. The reaction temperature of the reaction is usually -80 to 100
° C, and the reaction time is usually in the range of 1 to 100 hours. The amount of the reagent used in the reaction was 1 to 1000 mol of compound [II] per 1 mol of compound [I],
The base is in a proportion of 1 to 10 mol. Examples of the compound [II] include bromofluoromethane, chlorodifluoromethane and the like. As the base, for example, inorganic bases such as sodium hydroxide, potassium hydroxide, barium hydroxide, calcium hydroxide, sodium carbonate, potassium carbonate, barium carbonate, calcium carbonate, pyridine, 2-picoline, 4-picoline, 4- Dimethylaminopyridine,
Organic bases such as quinoline, triethylamine, ethyldiisopropylamine, N, N-dimethylaniline, N, N-diethylaniline, and mixtures thereof. As the solvent, N, N-dimethylformamide, N, N′-dimethylimidazolidin-2-one, N
Aprotic hydrophilic solvents such as -methyl-2-pyrrolidinone and sulfolane; ether solvents such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether and tert-butyl methyl ether , Hexane, heptane,
Aliphatic hydrocarbon solvents such as ligroin and petroleum ether,
Aromatic hydrocarbon solvents such as toluene and xylene; halogenated hydrocarbon solvents such as chloroform, dichloroethane, carbon tetrachloride, and monochlorobenzene; pyridine, triethylamine, N, N-dimethylaniline, N, N-diethylaniline, etc. Organic base solvents, ester solvents such as ethyl formate, butyl acetate, ethyl acetate, diethyl carbonate,
Examples include nitro compound solvents such as nitroethane and nitrobenzene, nitrile solvents such as acetonitrile and isobutyronitrile, water, and mixtures thereof. After completion of the reaction, the reaction solution is poured into water, extracted with an organic solvent, and subjected to a post-treatment operation such as concentration of the organic layer to obtain the target compound of the present invention. In addition, the compound of the present invention can be purified by recrystallization, chromatography or the like.

Compound [I] in the above-mentioned scheme (3)
Can be produced, for example, according to Scheme 4 below.

Embedded image [Wherein, R ¹ , R ³ , T, U, V, W and X represent the same meaning as described above. ]

In step 4, compound [III] and compound [I
V] in a solvent in the presence of a base. The reaction temperature of the reaction is usually 0 to 150 ° C.
And the reaction time is usually in the range of 1 to 24 hours. The amounts of the reagents used in the reaction were 1 to 100 mol of compound [IV] and 1 to 1 mol of base relative to 1 mol of compound [III].
１００100 mol. Examples of the base include inorganic bases such as sodium hydride and potassium hydride, sodium methoxide, sodium ethoxide, potassium-t
alkali metal alcoholates such as tert-butoxide;
Examples include alkaline earth metal alcoholates such as magnesium ethoxide, alkali metal amides such as sodium amide, lithium amide, lithium diisopropylamide, sodium hexamethyldisilazide, lithium hexamethyldisilazide, and mixtures thereof. Examples of the solvent include methanol, ethanol, and propanol.
Alcohol solvents such as toluene, butanol, and isopropanol; ether solvents such as 1,4-dioxane, tetrahydrofuran, ethylene glycol dimethyl ether, diethylene glycol dimethyl ether, and tert-butyl methyl ether. , Hexane, heptane, ligroin,
Aliphatic hydrocarbon solvents such as petroleum ether, aromatic hydrocarbon solvents such as toluene and xylene, halogenated hydrocarbon solvents such as dichloroethane, carbon tetrachloride, monochlorobenzene, pyridine, triethylamine, N-methylaniline , N, N-dimethylaniline, N, N-diethylaniline and other organic base solvents, acetonitrile, isobutyronitrile and other nitrile solvents, N, N-dimethylformamide, dimethylsulfoxide, N, N-dimethyl-
2-imidazolidone, sulfolane, or a mixture 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 a post-treatment operation such as extraction with an organic solvent and concentration, whereby the target compound [I] can be obtained. The compound [I] can be purified by recrystallization, chromatography or the like.

When the compound of the present invention is used as an active ingredient in agricultural and horticultural fungicides, it may be used as it is without adding any other components, but it is usually used as a solid carrier, a liquid carrier, a surfactant and other pharmaceutical preparations. Mix with adjuvants, emulsions, wettable powders,
It is formulated into suspensions, powders, granules, etc. and used. In these preparations, the compound of the present invention as an active ingredient is usually added in a weight ratio.
The content is 0.1% to 99.9%, preferably 1% to 90%. 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, Ammonium sulfate, fine powder or granular material such as synthetic hydrous silicon oxide, and the like, as a liquid carrier,
For example, aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil,
Examples include dimethyl sulfoxide, acetonitrile, water and the like. Examples of the surfactant include alkyl sulfate, alkyl (aryl) sulfonate, dialkyl sulfosuccinate, and polyoxyethylene alkyl aryl.
Anionic surfactants such as ruthele phosphate salt and naphthalene sulfonic acid formalin condensate; nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkyl polyoxypropylene block copolymer, and sorbitan fatty acid ester And the like. Pharmaceutical adjuvants include, for example, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP
(Acidic isopropyl phosphate). Specific examples of the application method of the compound of the present invention include foliage application, soil treatment, seed disinfection, and the like, and can be used in any application method usually used by those skilled in the art.

When the compound of the present invention is used as an active ingredient in an agricultural and horticultural fungicide, the application rate of the active ingredient depends on the type of the target plant (crop etc.), the type of the target disease, the degree of occurrence of the disease,
Although it may vary depending on the form of formulation, application method, application time, weather conditions, etc., it is usually 0.01 g to 50 g per al,
Preferably it is 0.05 g to 10 g. Emulsions, wettable powders,
When the suspension is diluted with water and applied, the application concentration is 0.0001% to 0.5%, preferably 0.000%.
It is 5% to 0.2%, and dusts, granules and the like are applied without dilution.

The compound of the present invention can be used as a fungicide for agricultural and horticultural use in fields, paddy fields, orchards, tea fields, pastures, lawns, etc., and can be used by mixing with other agricultural and horticultural fungicides. It can also be expected to increase the bactericidal efficacy. Examples of such other agricultural and horticultural fungicides include, for example, propiconazole, triazimenol, prochloraz, penconazole, tebuconazole, flusilazol, diniconazole, bromconazole, epoxyconazole, and difenoconazole.
, Cyproconazole, metconazole, triflumizole, tetraconazole, microbutanyl, fenbuconazole, hexaconazole, fluquinconazole,
Triconasol (RPA400727), Vitertano
Germicidal compounds such as benzyl, imazalil and furtriaphor, cyclized amine bactericidal compounds such as fenpropimorph, tridemorph and fenpropidine, and benzimidazoles such as carbendazim, benomyl, thiabendazole and thiophanate methyl. Fungicidal compounds, procymidone, cyprodinil, pyrimethanil, dietofencarb, thiuram, fluazinam, mancozeb, iprodione, vinclozolin, chlorothalonil, captan, mepanipyrim, fenpiclonil, fludioxonil, diclofluanid, folpet, clesoxime methyl,
Azoxystrobin, famoxadone, fenhexamide, N-methyl-α-methoxyimino-2-[(2,5
-Dimethylphenoxy) methyl] phenylacetamide. The compound of the present invention can be mixed or used in combination with other insecticides, acaricides, nematicides, herbicides, plant growth regulators, and fertilizers. Such insecticides and / or miticides and / or nematicides include, for example, fenitrothion [O, O-dimethyl O- (3-methyl-4
-Nitrophenyl) phosphorothioate], phenylion [O, O-dimethyl O- (3-methyl-4- (methylthio) phenyl) phosphorothioate], diazinon [O, O-diethyl-O-2-isopropyl-6] -Methylpyrimidin-4-yl phosphorothioate], chloropyrifos [O, O-diethyl-O-3,5,6-trichloro-2-pyridyl phosphorothioate], acephate [O, S- Dimethylacetylphosphoramide thioe-
G), methidathion [S-2,3-dihydro-5-methoxy-2-oxo-1,3,4-thiadiazol-3-
Ilmethyl O, O-dimethylphosphorodithioe-
G), disulfoton [O, O-diethyl S-2-ethylthioethyl phosphorothioate], DDVP [2,2
-Dichlorovinyldimethyl phosphate], sulphophos [O-ethyl O-4- (methylthio) phenyl S
-Propyl phosphorodithioate], cyanophos [O-
4-cyanophenyl O, O-dimethyl phosphorothioate], dioxabenzophos [2-methoxy-4H-
1,3,2-benzodioxaphosphinin-2-sulfide], dimethoate [O, O-dimethyl-S- (N-
Methylcarbamoylmethyl) dithiophosphate], phentoate [ethyl 2-dimethoxyphosphinothioylthio (phenyl) acetate], malathion [diethyl (dimethoxyphosphinothioylthio) succinate]
G), trichlorfon [dimethyl 2,2,2-trichloro-1-hydroxyethylphosphonate], azinphosmethyl [S-3,4-dihydro-4-oxo-1,
2,3-benzotriazin-3-ylmethyl O, O-
Dimethyl phosphorodithioate], monocrotophos [dimethyl (E) -1-methyl-2- (methylcarbamoyl) vinyl phosphate], ethion [O, O, O ',
Organic phosphorus compounds such as O'-tetraethyl S, S'-methylenebis (phosphorodithioate)] phosphthiazetate [N- (O-methyl-S-sec-butyl) phosphorylthiazolidine-2-one], BPMC (2 -Sec-butylphenylmethylcarbamate], benfracarb [ethyl N- (2,3-dihydro-2,2-dimethylbenzofuran-7-yloxycarbonyl (methyl) aminothio] -N-isopropyl-β-alanine- G), propoxur [2-isopropoxyphenyl N-methylcarbamate], carbosulfan [2,3-dihydro-
2,2-dimethyl-7-benzo [b] furanyl N-dibutylaminothio-N-methylcarbamate], carbaryl [1-naphthyl-N-methylcarbamate], mesomil [S-methyl-N -[(Methylcarbamoyl) oxy] thioacetimidate], ethiophenecarb [2
-(Ethylthiomethyl) phenylmethylcarbamoy
G], aldicarb [2-methyl-2- (methylthio)
Propionaldehyde O-methylcarbamoyloxime], oxamyl [N, N-dimethyl-2-methylcarbamoyloxyimino-2- (methylthio) acetamide], phenothiocarb [S-4-phenoxybutyl-
Carbamate compounds such as [N, N-dimethylthiocarbamate], ethofenprox [2- (4-ethoxyphenyl) -2-methylpropyl-3-phenoxybenzyl ether], fenvalerate [(RS) -α-cyano-3-phenoxybenzyl (RS) -2- (4-
Chlorophenyl) -3-methylbutyrate], esfenvalerate [(S) -α-cyano-3-phenoxybenzyl (S) -2- (4-chlorophenyl) -3-methylbutyrate], fenpropatrine [(RS) -α
-Cyano-3-phenoxybenzyl 2,2,3,3-
Tetramethylcyclopropanecarboxylate], cypermethrin [(RS) -α-cyano-3-phenoxybenzyl (1RS, 3RS) -3- (2,2-dichlorovinyl) -2,2-dimethylcyclopropanecarboxylate Rate), permethrin [3-phenoxybenzyl (1
RS, 3RS) -3- (2,2-dichlorovinyl)-
2,2-methylcyclopropanecarboxylate], cyhalothrin [(RS) -α-cyano-3-phenoxybenzyl (Z)-(1RS, 3RS) -3- (2-chloro-3,3,3- Trifluoropropenyl) -2,2-
Dimethylcyclopropanecarboxylate], deltamethrin [(S) -α-cyano-m-phenoxybenzyl (1R, 3R) -3- (2,2-dibromovinyl)-
2,2-dimethylcyclopropanecarboxylate],
Cycloprosulin [(RS) -α-cyano-3-phenoxybenzyl (RS) -2,2-dichloro-1- (4
-Ethoxyphenyl) cyclopropanecarboxyle-
Fluvalinate [α-cyano-3-phenoxybenzyl N- (2-chloro-α, α, α-trifluoro-p-tolyl) -D-valinate], bifenthrin [2-methylbiphenyl- 3-ylmethyl (Z)-
(1RS) -cis-3- (2-chloro-3,3,3-trifluoroprop-1-enyl) -2,2-dimethylcyclopropanecarboxylate], acrinasulin [(1R- {1α (S *), 3α (Z)｝]-2,2-
Dimethyl-3- [3-oxo-3- (2,2,2-trifluoro-1- (trifluoromethyl) ethoxy-1-
Propenyl] cyclopropanecarboxylic acid cyano (3-
Phenoxyphenol) methyl ester)], 2-methyl-2- (4-bromodifluoromethoxyphenyl) propyl (3-phenoxybenzyl) ether, tralomethrin [(S) -α-cyano-3-phenoxybenzyl
(1R) -cis-3- (1,2,2,2-tetrabromoethyl) -2,2-dimethylcyclopropanecarboxylate], silafluorene [[4-ethoxyphenyl (3- (4-fluoro-3- Pyrethroid compounds such as phenoxyphenyl) propyl) dimethylsilane, and buprofezin [2-tert-butylimino-3-isopropyl-5-phenyl-1,3,5-triadiadinane-4].
-One], nitroimidazolidine derivatives, cartap [S, S '-(2-dimethylaminotrimethylene) bis (thiocarbamate)], thiocyclam [N, N-dimethyl-1,2,3- Tritian-
Neristoxin derivatives such as 5-ylamine], bensultap [S, S'-2-dimethylaminotrimethylene di (benzenethiosulfonate)], N-cyano-
N-cyanoamidine derivatives such as N'-methyl-N '-(6-chloro-3-pyridylmethyl) acetamidine; endosulfan [6,7,8,9,10,10-hexachloro-1,5,5a, 6,9,9a-hexahydro-
6,9-methano-2,4,3-benzodioxathiepine oxide], gamma-BHC (1,2,3,4,
5,6-hexachlorocyclohexane], 1,1-bis (chlorophenyl) -2,2,2-trichloroethanol-
Chlorinated hydrocarbon compounds such as chlorofluazuron [1
-(3,5-dichloro-4- (3-chloro-5-trifluoromethylpyridin-2-yloxy) phenyl)-
3- (2,6-difluorobenzoyl) urea], teflubenzuron [1- (3,5-dichloro-2,4-difluorophenyl) -3- (2,6-difluorobenzoyl) urea], flufenoxuron [1 − (4- (2-
Benzoylphenylurea-based compounds such as chloro-4-trifluoromethylphenoxy) -2-fluorophenyl) -3- (2,6-difluorobenzoyl) urea]
Amitraz [N, N '[(methylimino) dimethylidine] di-2,4-xylysine], chlorodimform [N'-(4-chloro-2-methylphenyl) -N, N
Formaldehyde derivatives such as dimethylmethinimidamide, thiourea derivatives such as diafenthiuron [N- (2,6-diisopropyl-4-phenoxyphenyl) -N′-tert-butylcarbodiimide], phenylpyrazo-
Compound, tebufenozide [N-tert-butyl-N ′
-(4-ethylbenzoyl) -3,5-dimethylbenzohydrazide], 4-bromo-2- (4-chlorophenyl) -1-ethoxymethyl-5-trifluoromethylpyrrol-3-carbonitrile, bromopropyl [Isopropyl 4,4'-dibromobenzylate], tetradiphone [4-chlorophenyl 2,4,5-trichlorophenyl sulfone], quinomethionate [S, S-6
-Methylquinoxaline-2,3-diyldithiocarbonate], propargate [2- (4-tert-butylphenoxy) cyclohexylprop-2-yl sulfite], fenbutatin oxide [bis [tris (2-methyl -2-phenylpropyl) tin] oxide], hexthiazox [(4RS, 5RS) -5-
(4-chlorophenyl) -N-chlorohexyl-4-methyl-2-oxo-1,3-thiazolidine-3-carboxamide], clofentezine [3,6-bis (2-chlorophenyl) -1,2,4 , 5-tetrazine], pyridathioben [2-tert-butyl-5- (4-tert-butylbenzylthio) -4-chloropyridazine-3 (2H)
-One], fenpyroximate [tert-butyl (E)
-4-[(1,3-dimethyl-5-phenoxypyrazo-
4-yl) methyleneaminooxymethyl] benzoate], tebufenpyrad [N-4-tert-butylbenzyl) -4-chloro-3-ethyl-1-methyl-5-pyrazolcarboxamide], polyna Kuching complex [tetranactin, dinactin, trinactin], milbemectin, avermectin, ivamectin, azadirachtin [AZAD], pyrimidifen [5-chloro-N- [2- {4- (2-ethoxyethyl) -2,3-]
Dimethylphenoxydiethyl] -6-ethylpyrimidin-4-amine], pymetrozine [2,3,4,5-tetrahydro-3-oxo-4-[(pyridin-3-yl)
-Methyleneamino] -6-methyl-1,2,4-triazine] and the like.

Plant diseases which can be controlled by the compound of the present invention include the following diseases. Rice blast (Pyricularia oryzae), sesame leaf blight (Cochliobolus miyabeanus), sheath blight (Rhizoc)
tonia solani, wheat powdery mildew (Erysiphe grami)
nis), Fusarium head blight (Gibberella zeae), Rust (Puccinia
striiformis, P. graminis, P. recondita, P. horde
i), snow rot (Typhula sp., Micronectriella nivalis),
Nude smut (Ustilago tritici, U. nuda), black smut (Tilletia caries), eye spot disease (Pseudocercosporella h)
erpotrichoides), scald disease (Rhynchosporium secalis),
Leaf blight (Septoria tritici), Fusarium wilt (Leptosphaeria)
nodorum), citrus black spot (Diaporthe citri), scab (Elsinoe fawcetti), fruit rot (Penicillium)
digitatum, P. italicum), Monilia disease of apples (Sclero
tinia mali), rot (Valsa mali), powdery mildew (Pod
osphaera leucotricha), spot leaf spot (Alternaria mal
i), scab (Venturiainaequalis), pear scab (Ven
turia nashicola, V. pirina), black spot (Alternaria ki
kuchiana), scab (Gymnosporangium haraeanum), peach scab (Sclerotinia cinerea), scab (Cladospo)
rium carpophilum), Phomopsis rot
sp.), black scab (Elsinoe ampelina), late rot (Glomerella cingulata), powdery mildew (Uncinula neca)
tor), rust (Phakopsora ampelopsidis), black lot disease (Guignardia bidwellii), downy mildew (Plasmopara)
viticola), oyster anthracnose (Gloeosporium kaki), leaf rot (Cercospora kaki, Mycosphaerella nawae), cucumber anthracnose (Colletotrichum lagenarium), powdery mildew (Sphaerotheca fuliginea), vine blight (Mycosphaerella)
melonis), Fusarium oxysporum, Downy mildew (Ps
eudoperonospora cubensis), plague (Phytophthora s
p.), seedling wilt (Pythium sp.), tomato ring rot (Altern
aria solani), leaf mold (Cladosporium fulvum), plague (Phytophthora infestans), eggplant brown spot (Phomopsis)
vexans), powdery mildew (Erysiphe cichoracearum), black spot on cruciferous vegetables (Alternaria japonica), white spot (Cercosporella brassicae), rust on leek (Puccinia)
allii), soybean purpura (Cercospora kikuchii), black rot (Elsinoe glycines), black spot (Diaporthe phaseo)
lorum var. sojae), kidney anthracnose (Colletotrichu)
m lindemthianum), Peanut black spot (Cercospora p.
ersonata), brown spot (Cercospora arachidicola), pea powdery mildew (Erysiphe pisi), potato summer blight (Alternaria solani), blight (Phytophthora infesta)
ns), strawberry powdery mildew (Sphaerotheca humuli), tea net blast (Exobasidium reticulatum), white scab (El)
sinoe leucospila), tobacco scab (Alternaria long
ipes), powdery mildew (Erysiphe cichoracearum), anthracnose (Colletotrichum tabacum), downy mildew (Peronospora tab)
acina), plague (Phytophthora nicotianae), sugar beet brown spot (Cercospora beticola), rose scab (Diploc
arpon rosae), powdery mildew (Sphaerotheca pannosa),
Brown spot of chrysanthemum (Septoria chrysanthemi-indici), white rust (Puccinia horiana), gray mold on various crops (B
otrytis cinerea), Sclerotinia sclerotioru (Sclerotinia sclerotioru)
m) and the like.

[0018]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Production Examples, Preparation Examples, Test Examples, and the like, but the present invention is not limited to only these examples. First, a production example will be described.
The numbers of the compounds of the present invention are the compound numbers described in Tables 1 to 40 below.

Production Example 1 1.0 g (2.8 mmol) of methyl 2- {5- (1-benzyloxyiminoethyl) -2-methylphenoxy} -3-hydroxy-acrylate, 0.50 g of bromofluoromethane (4. 4 mmol), 0.32 g (3.1 mmol) of sodium carbonate and 4.0 ml of dimethylformamide were stirred in a sealed tube at room temperature for 3 hours. Thereafter, 30 ml of ethyl acetate was added to the reaction solution, which was added twice with dilute hydrochloric acid, once with aqueous sodium bicarbonate, and once with saturated saline.
Washing was performed successively. Next, the organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel thin-layer chromatography (hexane: ethyl acetate = 3: 1) to give methyl 2- {5- (1-benzyloxyiminoethyl) -2-methylphenoxy} -3-fluoromethoxy-acrylate ( The present compound number 1-14)
1.0 g (2.6 mmol) was obtained. Yield 92%. ¹ H-NMR (CDCl ₃ , TMS): δ (ppm): 7.50 (1
H, s), 7.3-7.5 (5H), 7.20 (1H, dd, J = 7.8,1.6Hz), 7.14 (1H,
d, J = 7.9Hz), 7.04 (1H, d, J = 1.5Hz), 5.47 (1H, d, J = 59Hz), 5.
20 (2H, s), 3.72 (3H, s), 2.36 (3H, s), 2.18 (3H, s)

Production Example 2 0.50 g (1.4 mmol) of methyl 2- {5- (1-benzyloxyiminoethyl) -2-methylphenoxy} -3-hydroxy-acrylate, N, N-dimethylimidazoline-2- While stirring a mixture of 5 ml of potassium hydroxide, 0.50 g (8.9 mmol) of potassium hydroxide, 1 ml of water and 30 mg (0.11 mmol) of 18-crown-6 under ice-cooling, chlorodifluoromethane gas was supplied for 2 hours. Introduced. Thereafter, the reaction solution was poured into 50 ml of a mixture of dilute hydrochloric acid and ice, and after confirming that the solution was acidic, this was extracted with 50 ml of ethyl acetate. The organic layer was washed with diluted hydrochloric acid, aqueous sodium bicarbonate solution and saturated saline solution in that order.
The organic layer was dried over magnesium sulfate and concentrated, and 0.50 g of methyl 2- {5- (1-benzyloxyiminoethyl) -2-methylphenoxy} -3-difluoromethoxy-acrylate (1. 23 mmol)
(Compound No. 1-139 of the present invention) was obtained. Yield 87
%. ¹ H-NMR (CDCl ₃ , TMS): δ (ppm): 7.67 (1
H, s), 7.25-7.45 (5H), 7.20 (1H, dd, J = 7.8,1.4Hz), 7.14 (1
H, d, J = 7.9Hz), 7.03 (1H, d, J = 1.1Hz), 6.39 (1H, t, J = 71Hz),
5.19 (2H, s), 3.72 (3H, s), 2.35 (3H, s), 2.17 (3H, s)

Reference Production Example 1 Potassium hydride (35% oil dispersion) 225.
0 g (1.963 mol) and 1,2-dimethoxyethane 1500 m
while stirring the mixture in an argon atmosphere at 10 ° C. or lower under ice-cooling, methyl 2- {5- (1-benzyloxyiminoethyl) -2-methylphenoxy} acetate 347.
A solution consisting of 4 g (1.061 mol), 510.0 g (8.490 mol) of methyl formate and 500 ml of 1,2-dimethoxyethane was added dropwise. After completion of the dropwise addition, 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 product was extracted twice with 3 l of methyl tertiary butyl ether, and the ether layer was collected, washed sequentially with water and saturated saline, dried over magnesium sulfate, filtered, and concentrated to obtain the desired methyl 2- {2-}. 5- (1-
310.0 g of benzyloxyiminoethyl) -2-methylphenoxy} -3-hydroxy-acrylate (about 0.872
3 mol yield: 82.2%). 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, examples of the compounds of the present invention are shown in the table together with the compound numbers. A compound represented by the formula:

[0023]

[Table 1]

[0024]

[Table 2]

[0025]

[Table 3]

[0026]

[Table 4]

[0027]

[Table 5]

[0028]

[Table 6]

[0029]

[Table 7]

[0030]

[Table 8]

[0031]

[Table 9]

[0032]

[Table 10]

[0033] A compound represented by the formula:

[0034]

[Table 11]

[0035]

[Table 12]

[0036]

[Table 13]

[0037]

[Table 14]

[0038]

[Table 15]

[0039]

[Table 16]

[0040]

[Table 17]

[0041]

[Table 18]

[0042]

[Table 19]

[0043]

[Table 20]

[0044] A compound represented by the formula:

[0045]

[Table 21]

[0046]

[Table 22]

[0047]

[Table 23]

[0048]

[Table 24]

[0049]

[Table 25]

[0050]

[Table 26]

[0051]

[Table 27]

[0052]

[Table 28]

[0053]

[Table 29]

[0054]

[Table 30]

[0055] A compound represented by the formula:

[0056]

[Table 31]

[0057]

[Table 32]

[0058]

[Table 33]

[0059]

[Table 34]

[0060]

[Table 35]

[0061]

[Table 36]

[0062]

[Table 37]

[0063]

[Table 38]

[0064]

[Table 39]

[0065]

[Table 40] In the above table, Me represents a methyl group, Et represents an ethyl group, Pr represents a propyl group, Bu represents a butyl group, and Pe represents a butyl group.
nt represents a pentyl group, Hex represents a hexyl group, Ph represents a phenyl group, Py represents a pyridyl group, and Bn represents a benzyl group. Also, n- is normal-, i- is iso-
, Sec- represents secondary-, t- represents tertiary-, and c- represents cyclo-.

Next, preparation examples will be shown. Parts represent parts by weight, and the compounds of the present invention are indicated by the compound numbers shown in Tables 1 to 40.

Formulation Example 1 Compounds 1-1 to 1-250, 2-1 to 2-25 of the present invention
50 parts of each of 0, 3-1 to 3-250 and 4-1 to 4-250, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are thoroughly pulverized and mixed, respectively. To obtain a wettable powder. Formulation Example 2 Compounds 1-1 to 1-250 of the present invention, 2-1 to 2-25
25 parts of each of 0, 3-1 to 3-250 and 4-1 to 4-250, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water were mixed. Each suspension is obtained by wet grinding to submicron size. Formulation Example 3 Compounds 1-1 to 1-250, 2-1 to 2-25 of the present invention
0, 3-1 to 3-250 and 4-1 to 4-250, 2 parts of each, 88 parts of kaolin clay and 10 parts of talc are thoroughly pulverized and mixed to obtain each powder. Formulation Example 4 Compounds 1-1 to 1-250, 2-1 to 2-25 of the present invention
0, 3-1 to 3-250 and 20 parts of 4-1 to 4-250, 14 parts of polyoxyethylene styrylphenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 60 parts of xylene are mixed well. To obtain the respective emulsions. Formulation Example 5 Compounds 1-1 to 1-250 and 2-1 to 2-25 of the present invention
0, 3-1 to 3-250 and 2 parts of 4-1 to 4-250, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium ligninsulfonate, 30 parts of bentonite and kaolin clay-6
5 parts are crushed and mixed well, water is added and kneaded well,
Each granule is obtained by granulation and drying. Formulation Example 6 Compounds 1-1 to 1-250 and 2-1 to 2-25 of the present invention
20 parts of each of 0, 3-1 to 3-250 and 4-1 to 4-250 and 1.5 parts of sorbitan trioleate were mixed with 28.5 parts of an aqueous solution containing 2 parts of polyvinyl alcohol,
After finely pulverized with a sand grinder (with a particle size of 3μ or less),
To this, 40 parts of an aqueous solution containing 0.05 part of xanthan gum and 0.1 part of aluminum magnesium silicate are added, and 10 parts of propylene glycol are further added and mixed by stirring to obtain a 20% suspension in water. Formulation Example 7 Compounds 1-1 to 1-250 of the Present Invention, 2-1 to 2-25
0, 3-1 to 3-250 and 4-1 to 4-250
0.1 part is dissolved in 5 parts of xylene and 5 parts of trichloroethane, and this is mixed with 89.9 parts of deodorized kerosene to obtain a 0.1% oil solution for each.

Next, test examples show that the compounds of the present invention are useful as fungicides for agricultural and horticultural use. In addition, this invention compound is shown by the compound number of Table 1-Table 40. The control effect of the compound of the present invention was evaluated by visually observing the area of the lesion on the test plant at the time of the investigation, and comparing the area of the lesion in the untreated section with the area of the lesion in the section treated with the compound of the present invention. did.

Test Example 1: Rice Blast Control Test (Preventive Effect) Sandy loam was packed in a plastic pot, and rice (Nipponbare) was sowed and grown in a greenhouse for 20 days. Thereafter, the compounds of the present invention 1-14 and 1-139 were made into a wettable powder according to Formulation Example 1, and then diluted with water to a predetermined concentration (500 ppm) so as to sufficiently adhere to the rice leaf surface. Foliage was sprayed.
After spraying, the plants were air-dried and sprayed with a suspension of the blast fungus. After inoculation, the plants were placed in a humid atmosphere at 28 ° C. for 6 days, and the control effect was examined. As a result, the compounds of the present invention 1-14 and 1
The lesion area on the plant in the -139 treatment group was 30% or less of the lesion area in the non-treatment group.

Test Example 2: Wheat powdery mildew control test (therapeutic 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. The wheat seedlings, which had developed the second leaf, were sprinkled with wheat powdery mildew spores and inoculated. After inoculation, they were placed in a greenhouse at 23 ° C. for 2 days.
After preparing Compounds 1-14 and 1-139 of the present invention as suspensions according to Formulation Example 2, the suspension was diluted with water to a predetermined concentration (500 ppm), and then applied to the leaves of wheat inoculated with powdery mildew fungi. The foliage was sprayed so as to adhere sufficiently. After spraying, it was further placed under lighting for 7 days, and the control effect was investigated. as a result,
The lesion area on plants in the treated areas of the present compounds 1-14 and 1-139 was 30% or less of the lesion area in the untreated area.

Test Example 3: Wheat 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. The compound of the present invention 1-14 was made into an emulsion according to Formulation Example 4, then diluted with water to a predetermined concentration (500 ppm), and sprayed on the leaves of the wheat so as to sufficiently adhere to the leaves. 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, the compound of the present invention 1-
The lesion area on the plants in the 14 treatments was 30% or less of the lesion area in the non-treatment.

Test Example 4: Test for Controlling Effect of Cucumber Gray Mold (Preventive Effect) Sandy loam was packed in a plastic pot, cucumber (Sagami Hanjiro) was sowed, and grown in a greenhouse for 12 days. After preparing Compound 1-14 of the present invention as a wettable powder according to Formulation Example 1, it was diluted with water to a predetermined concentration (500 ppm), and sprayed with foliage so as to sufficiently adhere to the cucumber leaves. After spraying, the plants were air-dried, and a PDA medium containing a hypha of cucumber gray mold fungus was placed on the cucumber leaves. After inoculation, the plants were placed in a humid environment at 10 ° C. for 4 days, and the control effect was examined. As a result, the compound of the present invention 1-
The lesion area on the plants in the 14 treatments was 30% or less of the lesion area in the non-treatment.

The compound of the present invention has excellent agricultural and horticultural bactericidal efficacy.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁷ Identification symbol FI Theme coat ゛ (Reference) A01N 43/54 A01N 43/54 D C07C 251/52 C07C 251/52 251/60 251/60 323/54 323 / 54 327/42 327/42 333/00 333/00 C07D 213/64 C07D 213/64 213/70 213/70 213/74 213/74 F term (reference) 4C055 AA01 BA01 BA02 BA03 BA06 BA16 BA30 BA42 BA47 BA52 BA54 BB01 BB02 BB04 BB07 BB10 BB11 CA01 CA02 CA03 CA06 CA13 CA39 CA52 CB01 CB02 DA01 DA30 DA54 DB01 DB02 DB04 DB07 DB10 DB11 EA01 4H006 AA01 AB03 BW20 BW21 TA04 TB21 TB32 TB53 TN10 TN30 TN50 ATN01 4H01

Claims (10)

[Claims] 1. A compound represented by the general formula: [Wherein, R ¹ is an A ¹ -ON = CA ² -group, A ¹ SC
(A ² ) = N-group or A ¹ SC (SA ² ) = N-group, wherein A ¹ and A ² are the same or different, and may be an optionally substituted alkyl group, Good alkenyl group, optionally substituted alkynyl group, optionally substituted cycloalkyl group, optionally substituted cycloalkylalkyl group, optionally substituted cycloalkenyl group, optionally substituted Represents a cycloalkenylalkyl group, an optionally substituted aryl group, an optionally substituted arylalkyl group, an optionally substituted heteroaryl group or an optionally substituted heteroarylalkyl group. ｝, R ² represents a fluoromethyl group or a difluoromethyl group, R ³ represents an alkyl group, one of T, U and V represents a CR ⁴ group, and the other represents a CH group or a nitrogen atom. And the other one represents a CR ⁵ group or a nitrogen atom, W represents a CR ⁴⁴ group or a nitrogen atom, wherein R ⁴ , R ⁵ and R ⁴⁴ 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, a cyano group, a nitro group, an alkoxycarbonyl group, an alkylthio group or a haloalkylthio group. ｝, X
R ⁶ {wherein representing the the NR ⁶ group, an oxygen atom or a sulfur atom
Represents an alkyl group. ｝. ] The acrylic acid derivative shown by these. 2. In the acrylic acid derivative represented by the general formula 1, R ¹ is the same or different, and A ¹ and A ² are the same or different, and a halogen atom, an alkyl group, a haloalkyl group, a cycloalkyl group, an alkoxy group, a haloalkoxy group. Group, alkylthio group, haloalkylthio group, alkylamino group,
Dialkylamino group, alkoxycarbonyl group, haloalkoxycarbonyl group, alkylaminocarbonyl group,
2. A group selected from the following group which may be substituted with one or more groups selected from the group consisting of a dialkylaminocarbonyl group, an acylamino group, an alkoxycarbonylamino group, a cyano group and a nitro group. The acrylic acid derivative according to 1. [Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, cycloalkylalkyl group, cycloalkenyl group, cycloalkenylalkyl group, aryl group, arylalkyl group, heteroaryl group and heteroarylalkyl group] 3. A ¹ and A ² in R ¹ of the acrylic acid derivative represented by the above general formula 1 are the same or different, and may be a C1-C10 alkyl group which may be substituted, or may be substituted. C2-C10 alkenyl group, optionally substituted C2-C10 alkynyl group, optionally substituted C3-C10 cycloalkyl group, optionally substituted C4-C20 cycloalkylalkyl group, optionally substituted A good C5-C10 cycloalkenyl 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 heteroaryl a group or an optionally substituted C2~C19 heteroarylalkyl group, R ³ is C1~C5 alkyl group, R ^4, R ⁵ and R ⁴⁴ are identical or different, a hydrogen atom, a halogen atom, C1-C10 alkyl group, C1
-C10 alkoxy group, C1-C10 haloalkyl group,
C1-C10 haloalkoxy group, cyano group, nitro group,
The acrylic acid derivative according to claim 1, which is a C2 to C10 alkoxycarbonyl group, a C1 to C10 alkylthio group or a C1 to C10 haloalkylthio group, and wherein R ⁶ is a C1 to C10 alkyl group. 4. An acrylic acid derivative represented by the general formula ¹ wherein A ¹ and A ² in R ¹ are the same or different,
Halogen atom, C1-C10 alkyl group, C1-C10
Haloalkyl group, C3-C10 cycloalkyl group, C1
-C10 alkoxy group, C1-C10 haloalkoxy group, C1-C10 alkylthio group, C1-C10 haloalkylthio group, C1-C10 alkylamino group, C2-
C20 dialkylamino group, C2-C10 alkoxycarbonyl group, C2-C10 haloalkoxycarbonyl group, C2-C10 alkylaminocarbonyl group, C3-
1 selected from the group consisting of a C10 dialkylaminocarbonyl group, a C2-C10 acylamino group, a C2-C10 alkoxycarbonylamino group, a cyano group and a nitro group
The acrylic acid derivative according to claim 1 or 3, which is any group selected from the following group which may be substituted with at least one kind of group. [C1-C10 alkyl group, C2-C10 alkenyl group, C2-C10 alkynyl group, C3-C10 cycloalkyl group, C4-C20 cycloalkylalkyl group, C5-C10 cycloalkenyl group, C6-C20 cycloalkenylalkyl group, C6 A -C10 aryl group,
C7-C20 arylalkyl group, C1-C9 heteroaryl group and C2-C19 heteroarylalkyl group] 5. An acrylic acid derivative represented by the above general formula ¹ wherein A ¹ and A ² in R ¹ are the same or different,
Halogen atom, C1-C10 alkyl group, C1-C10
Haloalkyl group, C3-C10 cycloalkyl group, C1
-C10 alkoxy group, C1-C10 haloalkoxy group, C1-C10 alkylthio group, C1-C10 haloalkylthio group, C2-C10 alkoxycarbonyl group,
The acrylic according to claim 1 or 3, which is any group selected from the following group which may be substituted with one or more groups selected from the group consisting of a C2 to C10 haloalkoxycarbonyl group, a cyano group, and a nitro group. Acid derivatives. [C1 to C1
0 alkyl group, C2-C10 alkenyl group, C2-C1
0 alkynyl group, C3-C10 cycloalkyl group, C4
-C20 cycloalkylalkyl group, C5-C10 cycloalkenyl group, C6-C20 cycloalkenylalkyl group, C6-C10 aryl group, C7-C20 arylalkyl group, C1-C9 heteroaryl group and C2-C
19 heteroarylalkyl group] 6. An acrylic acid derivative represented by the above general formula 1, wherein R ³ is a methyl group, and R ⁴ , R ⁵ and R
The acrylic acid derivative according to any one of claims 1 to 5, wherein ⁴⁴ are the same or different and are a hydrogen atom, a halogen atom, a C1 to C10 alkyl group or a C1 to C10 haloalkyl group, and R ⁶ is a methyl group. 7. The acrylic acid derivative according to claim 6, wherein R ⁴ , R ⁵ and R ⁴⁴ are the same or different and are a hydrogen atom or a methyl group. 8. The acrylic acid derivative according to claim 1, wherein in the general formula 1, X is an oxygen atom. 9. In the general formula 1, one of T, U and V is a CR ⁴ group, the other is a CH group,
Further, a remaining one is CR ⁵ group, W is CR ⁴⁴ group (R ^4, R ⁵ and R ⁴⁴ are,. As defined above) acrylic according to claim 1 Acid derivatives. 10. A fungicide for agricultural and horticultural use, comprising the acrylic acid derivative according to claim 1 as an active ingredient.