JPH11158131A - Allylacetic acid amide derivatives and fungicides for agricultural and horticultural use - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject new compound capable of exhibiting excellent control effects against rice blast, apple scab and so on and excellent residual effects and rain resistance without causing chemical injury on crops, and useful as an antimicrobial agent for agriculture and horticulture. SOLUTION: A compound of formula I A is 1- or 2-naphthyl substituted by the formula: Xn [X is a halogen, a 1-6C alkyl, OH or the like; (n) is 1-3]; R<1> is a halogen, a 1-6C (cyclo)alkoxy, a 1-6C alkylthio or the like; R<2> is a 1-6C (cyclo)alkyl, a 1-4C haloalkyl or the like; R<3> is a 2-6C (cyclo)alkyl, a 2-6C alkenyl or the like; Q is cyano, a group of the formula: COR<4> [R<4> is a 1-6C (cyclo)alkyl, a 1-4C haloalkyl or the like]}. For example, N-(1-cyano-1,2,2- trimethylpropyl)-2-methoxy-2-(4-methoxyphenyl)acetamide. The compound of formula I is obtained by allowing a compound of formula II to react with a compound of formula III in the presence of a condensing agent.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an arylacetic acid amide derivative which is a novel compound not described in any literature, and a fungicide for agricultural and horticultural use containing the same as an active ingredient.

[0002]

2. Description of the Related Art Hitherto, 2- (α-bromophenylacetylamino) isobutyric acids have been known as intermediates for producing nitrogen-containing cyclic compounds (JP-A-8-15136).
No. 4 publication), but its usefulness as an agricultural and horticultural fungicide is not known at all.

[0003]

In recent years, due to the heavy use of fungicides for agricultural and horticultural use, resistant bacteria have emerged, and existing drugs may not show sufficient bactericidal activity. In addition, a new disinfectant capable of efficiently controlling harmful bacteria at a low concentration is demanded due to environmental problems.

[0004]

DISCLOSURE OF THE INVENTION The present inventors have synthesized various novel arylacetic acid amide derivatives in order to develop a drug having a bactericidal activity superior to conventionally known bactericides.
Examination of the physiological activity revealed that the compound of the present invention has excellent bactericidal activity against rice blast and the like and does not cause any harm to useful crops. Thus, the present invention has been completed.

That is, the present invention provides (1) a general formula [1]

[0006]

Embedded image [Wherein the phenyl group A is substituted by _{X n, X n}
Represents has been or 2-naphthyl group substituted by may 1-naphthyl group or _{X n} to be replaced by, X is a halogen _atom, C 1 -C ₆ alkyl _group, C 2 -C ₆ alkenyl _{group, C} 2 ~ C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₄ haloalkyl group, hydroxy group, C
₁ -C ₆ alkoxy _group, C 2 -C ₆ alkenyloxy _group, C 2 -C ₆ alkynyloxy _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ haloalkoxy group, a phenoxy group (said group A C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom.), A C ₁ -C ₆ alkylthio group, ₁ -C ₄ haloalkylthio group, phenylthio group (in which is substituted by _C 1 -C ₆ alkyl _group, C 1 -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom An amino group, a C ₁ -C ₆ alkylamino group, a C ₁ -C ₆ dialkylamino group, a cyano group,
A phenyl group (the group is a C ₁ -C ₆ alkyl group, a C ₁ -C ₄
Haloalkyl group, C ₁ -C ₆ alkoxy group, cyano group,
It may be substituted by a nitro group or a halogen atom. ), An aralkyl group (the group is a C ₁ -C ₆ alkyl group,
C ₁ -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy group,
It may be substituted by a cyano group, a nitro group or a halogen atom. ), A C ₁ -C ₆ alkylcarbonyl group, a benzoyl group (the group is a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom. May be substituted.) Or a C ₁ -C ₆ alkoxycarbonyl group, n represents an integer of 1 to 3, R ¹ represents a halogen atom,
₁ -C ₆ alkoxy _group, C 3 -C ₆ cycloalkoxy _group, C 1 -C ₄ haloalkoxy _groups, C 1 -C ₆ alkylthio _group, C 1 -C ₆ alkylamino group or a _C 1 -C ₆ dialkylamino group And R ² represents a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group or a C ₁ -C ₄ haloalkyl group, and R ³ represents a C ₂ -C ₆ alkyl group, C _2-
A C ₆ alkenyl group, a C ₃ -C ₆ cycloalkyl group (the group may be substituted by a C ₁ -C ₆ alkyl group or a halogen atom) or a C ₁ -C ₄ haloalkyl group;
Alternatively, R ² and R ³ together with the carbon atom to which they are attached represent a 5- to 7-membered cycloalkyl group (the group may be substituted by a C ₁ -C ₆ alkyl group or a halogen atom); Is a cyano group or a group —COR ⁴ (R ⁴ is C ₁ -C ₆
Alkyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₄
Haloalkyl _groups, C 1 -C ₆ alkoxy _group, C 2 -C ₆
An alkenyloxy group, a C ₂ -C ₆ alkynyloxy group,
C ₃ -C ₆ cycloalkyloxy group, an amino _{group, C} 1 ~
Represents a C ₆ alkylamino group or a C ₁ -C ₆ dialkylamino group. ). And (2) a fungicide for agricultural and horticultural use containing the arylacetic acid amide derivative as an active ingredient.

First, terms used in the present specification will be described below. In the present specification, for example, the notation “C _{1 to} C ₆ ” or the like indicates that the number of carbon atoms of the subsequent substituent is 1 to 6 in this case.

The C ₁ -C ₆ alkyl group means a linear or branched alkyl group, such as a methyl group, an ethyl group,
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, n
-Pentyl group, isopentyl group, neopentyl group, n-
Examples include a hexyl group, an isohexyl group, and a 3,3-dimethylbutyl group.

The C ₃ -C ₆ cycloalkyl group includes, for example, a cyclopropyl group, a cyclopentyl group, a cyclohexyl group and the like.

The C ₁ -C ₄ haloalkyl group represents a linear or branched alkyl group substituted by a halogen atom, for example, a fluoromethyl group, a chloromethyl group,
Examples thereof include a difluoromethyl group, a dichloromethyl group, a trifluoromethyl group, and a pentafluoroethyl group.

The C ₂ -C ₆ alkenyl group is a linear or branched alkenyl group such as a vinyl group, a 1-propenyl group, an allyl group, an isopropenyl group, a 1-butenyl group and a 2-butenyl group. And the like.

The C ₂ -C ₆ alkynyl group means a linear or branched alkynyl group such as an ethynyl group and a 1-alkynyl group.
Propynyl group, 2-propynyl group, 1-butynyl group, 2
-Butynyl group, 3-butynyl group, 4-methyl-1-pentynyl group, 3-methyl-1-pentynyl group and the like.

The aralkyl group refers to a linear or branched C ₁ -C ₃ alkyl group substituted by an aryl group, such as benzyl, phenethyl, 1-naphthylmethyl, 2-naphthylmethyl and the like. Can be mentioned.

The halogen atom means a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.

The C ₁ -C ₆ alkoxy group represents a linear or branched alkoxy group, for example, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, sec -Butoxy group, te
Examples thereof include an rt-butoxy group, an n-pentyloxy group, an isopentyloxy group, and an n-hexyloxy group.

The C ₂ -C ₆ alkenyloxy group means a linear or branched alkenyloxy group, such as an allyloxy group, an isopropenyloxy group or a 2-butenyloxy group.

The C ₂ -C ₆ alkynyloxy group means a linear or branched alkynyloxy group.
Examples thereof include a propynyloxy group, a 2-butynyloxy group, and a 3-butynyloxy group.

The C ₃ -C ₆ cycloalkyloxy group is
For example, a cyclopropyloxy group, a cyclopentyloxy group, a cyclohexyloxy group and the like can be mentioned.

The C ₁ -C ₄ haloalkoxy group represents a straight-chain or branched-chain alkoxy group substituted by a halogen atom, such as fluoromethoxy, difluoromethoxy, trifluoromethoxy, and pentafluoroethoxy. And the like.

The C ₁ -C ₆ alkylthio group means a linear or branched alkylthio group such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, isobutylthio, sec
-Butylthio group, tert-butylthio group, n-hexylthio group and the like.

The C ₁ -C ₄ haloalkylthio group represents a straight-chain or branched-chain alkylthio group substituted by a halogen atom, for example, a fluoromethylthio group, a difluoromethylthio group, a trifluoromethylthio group, a pentafluoroethyl group. And thio groups.

The C ₁ -C ₆ alkylamino group represents a linear or branched alkylamino group, such as a methylamino group, an ethylamino group, an n-propylamino group, an isopropylamino group, an n-butylamino group. Group, isobutylamino group, sec-butylamino group, tert-butylamino group, n-hexylamino group and the like.

The C ₁ -C ₆ dialkylamino group includes, for example, a dimethylamino group, a diethylamino group, a dipropylamino group, a dibutylamino group and the like.

The C ₁ -C ₆ alkylcarbonyl group represents a linear or branched alkylcarbonyl group, and includes, for example, an acetyl group, a propionyl group, a butyryl group and an isobutyryl group.

The C ₁ -C ₆ alkoxycarbonyl group is
Represents a linear or branched alkoxycarbonyl group, for example, methoxycarbonyl group, ethoxycarbonyl group, n
-Propoxycarbonyl group, isopropoxycarbonyl group, n-butoxycarbonyl group, isobutoxycarbonyl group, sec-butoxycarbonyl group, tert-butoxycarbonyl group, n-pentyloxycarbonyl group,
and n-hexyloxycarbonyl group.

Some of the compounds of the present invention represented by the general formula [1] have one or two or more asymmetric carbon atoms in the molecule. There are isomers. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.

As a preferable compound of the compound of the present invention represented by the general formula [1], A is a phenyl group or 2-naphthyl group substituted by _Xn , and R ¹ is a chlorine atom, a bromine atom, a methoxy group or A methylthio group, R ² is a methyl group, an ethyl group or an n-propyl group, and R ³ is an ethyl group,
n-propyl group, isopropyl group, n-butyl group, isobutyl group, sec-butyl group, tert-butyl group, cyclopropyl group, 1-methylcyclopropyl group, cyclobutyl group, cyclopentyl group or dichloromethyl group,
Q is a cyano group, a methoxycarbonyl group, an ethoxycarbonyl group or an acetyl group, and X is a fluorine atom, a chlorine atom,
Bromine atom, iodine atom, methyl group, ethyl group, isopropyl group, isobutyl group, tert-butyl group, trifluoromethyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, difluoromethoxy group, trifluoromethoxy Group, phenoxy group, methylthio group, ethylthio group, isopropylthio group, dimethylamino group,
Compounds in which n is an integer of 1-2, such as a diethylamino group or a phenyl group, can be mentioned.

[0028]

BEST MODE FOR CARRYING OUT THE INVENTION Next, specific examples of the compound of the present invention represented by the general formula [1] are shown in Tables 1 to 22, but are not limited thereto.

[0029]

[Table 1]

[0030]

[Table 2]

[0031]

[Table 3]

[0032]

[Table 4]

[0033]

[Table 5]

[0034]

[Table 6]

[0035]

[Table 7]

[0036]

[Table 8]

[0037]

[Table 9]

[0038]

[Table 10]

[0039]

[Table 11]

[0040]

[Table 12]

[0041]

[Table 13]

[0042]

[Table 14]

[0043]

[Table 15]

[0044]

[Table 16]

[0045]

[Table 17]

[0046]

[Table 18]

[0047]

[Table 19]

[0048]

[Table 20]

[0049]

[Table 21]

[0050]

[Table 22]

The compound of the present invention represented by the general formula [1]
For example, it can be manufactured according to the following manufacturing method.

Production method 1

[0053]

Embedded image (In the formula, R ¹ , R ² , R ³ , A and Q represent the same meaning as described above.)

The compound [1] of the present invention is represented by the general formula [3] by using an arylacetic acid derivative represented by the general formula [2] and optionally using a condensing agent in the presence of a catalyst and / or a base. It can be produced by reacting with amines.

This reaction is usually performed in a solvent. As a solvent that can be used, any solvent that does not inhibit the reaction may be used. Carbon, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, acetone, methyl ethyl ketone,
Ketones such as methyl isopropyl ketone and methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; or aprotic compounds such as dimethyl sulfoxide, N, N-dimethylformamide and sulfolane A polar solvent or a mixed solvent obtained by combining solvents selected from these can be used.

As the condensing agent, for example, 1-ethyl-3-
(3-Dimethylaminopropyl) carbodiimide hydrochloride, N, N'-dicyclohexylcarbodiimide, carbonyldiimidazole, 2-chloro-1,3-dimethylimidazolium chloride and the like.

Examples of the catalyst include 4-dimethylaminopyridine, 1-hydroxybenzotriazole, dimethylformamide and the like.

As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, or triethylamine, trimethylamine, N, N -Dimethylaniline, pyridine, N-methylpiperidine, 1,5-
Diazabicyclo [4.3.0] non-5-ene (DB
N), organic bases such as 1,8-diazabicyclo [5.4.0] -7-undecene (DBU) and the like, and preferably tertiary amines such as triethylamine, pyridine and N-methylpiperidine. Can be

The reaction temperature ranges from -50 ° C to 150 ° C,
It is preferably carried out in the range of 0 ° C to 60 ° C. The reaction time is preferably 1 to 30 hours.

Next, a method for producing a starting compound used in this production method will be described.

First, the compound represented by the general formula [2] is
A publicly known method [for example, Journal of the
American Chemical Society
y, 82, 4062 (1960); Orga
nic Synthesis, Vol. 6, p. 403 (1
988) or a method analogous thereto.

The compound represented by the general formula [3] is
Known methods [for example, Organic Synthesi
s, vol. 3, p. 88 (1955); Journal
of Medicinal Chemistry, 9, 911 (1966); Tetrahedr.
on Letters, vol. 17, p. 1455 (19
77)) or a method analogous thereto.

Production method 2

[0064]

Embedded image (In the formula, R ¹ , R ² , R ³ , A and Q represent the same meaning as described above, and L represents a halogen atom.)

The compound [1] of the present invention can be produced by reacting an aryl acetic acid halide represented by the general formula [4] with an amine represented by the general formula [3] in the presence of a base. .

This reaction is usually performed in a solvent. As a solvent that can be used, any solvent that does not inhibit the reaction may be used. Carbon, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, acetone, methyl ethyl ketone,
Ketones such as methyl isopropyl ketone and methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; nitriles such as acetonitrile and propionitrile; or aprotic polar solvents such as N, N-dimethylformamide and sulfolane Alternatively, a mixed solvent obtained by combining solvents selected from these can be used.

As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, and tertiary amines such as triethylamine and trimethylamine Organic amines such as tertiary amines, pyridine, picoline and the like can be mentioned, and preferred are alkali metal carbonates and tertiary amines.

The reaction temperature ranges from -50 ° C. to 150 ° C.
It is preferably carried out in the range of 0 ° C to 60 ° C. The reaction time is preferably 1 to 30 hours.

The aryl acetic acid halide represented by the general formula [4] can be obtained by converting the aryl acetic acid represented by the general formula [2] produced by the above-mentioned method into, for example, thionyl chloride, phosphorus pentachloride, tribromide. It can be produced by reacting with a halogenating agent such as phosphorus.

Manufacturing method 3

[0071]

Embedded image (Wherein, R ² , R ³ , A, Q and L represent the same meaning as described above, and R ^{1 ′} represents an alkoxy group, a cycloalkoxy group,
Represents a haloalkoxy group, an alkylthio group, an alkylamino group or a dialkylamino group. )

The compound [1] of the present invention has the general formula [1-1]
Can be produced by reacting an α-halogenoarylacetic acid amide represented by the formula with an alcohol, a mercaptan or an amine represented by the general formula [5] in the presence of a base.

This reaction is usually performed in a solvent. As a solvent that can be used, any solvent that does not inhibit the reaction may be used. Carbon, chlorobenzene, halogenated hydrocarbons such as dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran, dioxane, acetone, methyl ethyl ketone,
Ketones such as methyl isopropyl ketone and methyl isobutyl ketone, acetates such as methyl acetate and ethyl acetate, nitriles such as acetonitrile and propionitrile, alcohols such as methanol and ethanol or dimethyl sulfoxide, N, N-dimethylformamide And aprotic polar solvents such as sulfolane or a mixed solvent obtained by combining solvents selected from these.

As the base, those generally used in this type of reaction can be used. For example, alkali metal hydroxides such as sodium hydroxide and potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, alkali metal carbonates such as sodium carbonate and potassium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and the like Alkali metal hydrogen carbonates, alkali metal hydrides such as sodium hydride and potassium hydride, alkali metal alcoholates such as sodium methylate and sodium ethylate, tertiary amines such as triethylamine and trimethylamine, and organic compounds such as pyridine. Bases and the like can be mentioned, and preferred are alkali metal carbonates, alkali metal hydrides and alkali metal alcoholates.

The reaction temperature ranges from -50 ° C. to 150 ° C.
It is preferably carried out in the range of 0 ° C to 60 ° C. The reaction time is preferably 1 to 30 hours.

[0076]

The production method, the preparation method and the use of the compound of the present invention will be specifically described below with reference to examples.

Production Example 1 N- (1-cyano-1,2,2-trimethylpropyl)
Production of -2-methoxy-2- (4-methoxyphenyl) acetamide (Compound No. A-37)

A) Ethyl 2- in 30 ml of ethanol
5.0 g of methoxy-2- (4-methoxyphenyl) acetate was dissolved. 15 ml of a 10% aqueous sodium hydroxide solution was added dropwise to this solution. After stirring at room temperature for 12 hours, the reaction solution was poured into water, diluted hydrochloric acid was added, and the mixture was extracted with diethyl ether. After drying over anhydrous magnesium sulfate,
Diethyl ether was distilled off under reduced pressure to give a melting point of 55-57.
3.6 g (82% yield) of 2-methoxy-2- (4-methoxyphenyl) acetic acid at <RTIgt;

B) 15.4 g of sodium cyanide and 300 ml of ammonium chloride in 300 ml of 25% aqueous ammonia.
0 g was added. 30.0 g of 3,3-dimethyl-2-butanone was added dropwise to this mixture under ice cooling. After stirring at room temperature for 24 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure, and 28.2 g of 2-amino-2,3,3-trimethylbutyronitrile having a melting point of 107 to 110 ° C.
(74% yield).

C) 0.4 g of 2-methoxy-2- (4-methoxyphenyl) acetic acid in 20 ml of dichloromethane,
1.1 g of -ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride were added. After stirring for 10 minutes, 0.5 g of 2-amino-2,3,3-trimethylbutyronitrile was added. After stirring at room temperature for 3 hours, the reaction solution was poured into water and extracted with dichloromethane. After drying over anhydrous magnesium sulfate, dichloromethane was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and the target substance having a refractive index of 1.5223 (20 ° C.) was purified.
g (79% yield).

Production Example 2 2-bromo-2- (4-chlorophenyl) -N- (1-
Production of (cyano-1,2-dimethylpropyl) acetamide (Compound No. A-1)

A) 5.8 g of bromine was added to a mixture of 3.0 g of 2- (4-chlorophenyl) acetic acid and 3.5 g of phosphorus tribromide.
Was added dropwise at room temperature. After stirring for 30 minutes, heat to 80-90 ° C
For 6 hours. The reaction solution was poured into ice water and extracted with toluene. After drying over anhydrous magnesium sulfate, toluene was distilled off under reduced pressure, and 2-bromo-2- (4
5.3 g of (-chlorophenyl) acetyl bromide (yield 9
6%).

B) 2-to 50 ml of tetrahydrofuran
2.2 g of amino-2,3-dimethylbutyronitrile and 2.4 g of triethylamine were added. To this mixture, 6.2 g of 2-bromo-2- (4-chlorophenyl) acetyl bromide was added dropwise under ice cooling. After stirring at room temperature for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 5.6 g (yield: 83%) of the desired product having a melting point of 110 to 113 ° C.

Production Example 3 2- (4-chlorophenyl) -N- (1-cyano-1,
Production of 2-dimethylpropyl) -2-methoxyacetamide (Compound No. A-2)

2-bromo-2- in 30 ml of methanol
(4-chlorophenyl) -N- (1-cyano-1,2-
1.0 g of dimethylpropyl) acetamide and 0.6 g of sodium methylate (28% methanol solution) were added. After stirring under heating and refluxing for 3 hours, the reaction solution was poured into water and extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.6 g of the target product having a refractive index of 1.5105 (20 ° C.) (yield 70
%).

Production Example 4 2- (4-chlorophenyl) -N- (1-cyano-1,
Production of 2-dimethylpropyl) -2-methylthioacetamide (Compound No. A-9)

2-Bromo-2-ethanol in 30 ml of methanol
(4-chlorophenyl) -N- (1-cyano-1,2-
1.0 g of dimethylpropyl) acetamide and 1.4 g of methyl mercaptan sodium salt (15% aqueous solution) were added. After stirring at room temperature for 12 hours, the reaction solution was poured into water and extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, melting point 121
0.7 g (yield 78%) of the target product at ~ 124 ° C was obtained.

Production Example 5 Production of 2-bromo-N- (1-cyano-1,2,2-trimethylpropyl) -2- (2-naphthyl) acetamide (Compound No. B-8)

To 30 ml of tetrahydrofuran were added 5.5 g of 2-amino-2,3,3-trimethylbutyronitrile and 6.1 g of triethylamine. To this mixture was added 2-bromo-2- (2-naphthyl) acetyl bromide 16.4.
g was added dropwise under ice cooling. After stirring at room temperature for 5 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 13.5 g of the desired product having a melting point of 128 to 131 ° C (yield: 8).
3%).

Production Example 6 N- (1-cyano-1,2,2-trimethylpropyl)
Production of -2-methoxy-2- (2-naphthyl) acetamide (Compound Nos. B-4 and B-5)

2-Bromo-N- in 30 ml of methanol
(1-cyano-1,2,2-trimethylpropyl) -2
3.5 g of-(2-naphthyl) acetamide and 1.9 g of sodium methylate (28% methanol solution) were added. After stirring under heating and refluxing for 3 hours, the reaction solution was poured into water and extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure. The residue is purified by silica gel column chromatography, and diastereomer A of the target compound having a melting point of 117 to 119 ° C.
(Low polar substance) 1.3 g (yield 43%) and refractive index 1.5
Diastereomer B of the target compound at 574 (20 ° C.)
(Highly polar substance) 1.1 g (yield 36%) was obtained.

Production Example 7 2-bromo-N- (1-isopropyl-1-methyl-2)
Production of -oxopropyl) -2- (4-trifluoromethylphenyl) acetamide (Compound No. A-65)

A) 12.5 g of N- (1-isopropyl-1-methyl-2-oxopropyl) acetamide was added to 300 ml of 6N hydrochloric acid. After stirring for 5 hours under reflux,
The mixture was concentrated under reduced pressure. The residue was washed with acetone and 3-amino-3,4-dimethyl-melting point 202 ° C.
5.7 g (36% yield) of 2-pentanone hydrochloride was obtained.

B) 3-Amino-3,4-dimethyl-2-pentanone hydrochloride 1.0 in 20 ml of acetonitrile
g of potassium carbonate and 1.8 g of potassium carbonate. 2-
2.0 g of bromo-2- (4-trifluoromethylphenyl) acetyl bromide was added dropwise under ice cooling. After stirring at room temperature for 7 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 1.0 g (yield: 40%) of the desired product having a melting point of 165 to 167 ° C.

Production Example 8 N- (1-Isopropyl-1-methyl-2-oxopropyl) -2-methoxy-2- (4-trifluoromethylphenyl) acetamide (Compound Nos. A-66 and A-6)
7) Manufacturing

2-Bromo-N- in 30 ml of methanol
0.8 g of (1-isopropyl-1-methyl-2-oxopropyl) -2- (4-trifluoromethylphenyl) acetamide and 0.6 g of sodium methylate (28% methanol solution) were added. After stirring under heating and refluxing for 3 hours, the reaction solution was poured into water and extracted with ethyl acetate. After drying over anhydrous magnesium sulfate, ethyl acetate was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.2 g (29% yield) of diastereomer A (low-polar substance) of the target compound having a melting point of 120 to 122 ° C.
And 0.2 g (yield 29%) of diastereomer B (highly polar substance) of the target compound having a melting point of 79 to 81 ° C.

Production Example 9 (S)-(+)-2- (4-bromophenyl) -N-
(1-Isopropyl-1-methyl-2-oxopropyl) -2-methoxyacetamide (Compound No.A-9
5, A-96)

A) 2- (4-) was added to 200 ml of ethyl acetate.
7.2 g of (bromophenyl) -2-methoxyacetic acid were dissolved. 2. Add (S)-(−)-phenethylamine to this solution.
6 g was added, and the mixture was stirred under reflux for 2 hours. Cool to room temperature,
The precipitated diastereomer salt was collected by filtration and recrystallized three times with water. Dilute hydrochloric acid was added to this salt, and extracted with chloroform. After drying over anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure to give (S)-having a melting point of 87 to 89 ° C.
1.6 g (yield 32%) of (+)-2- (4-bromophenyl) -2-methoxyacetic acid was obtained. Specific rotation: [α] _D
²⁴ = + 103.3 ° (c = 0.13, CHCl ₃ ) b) (S)-(+)-2- in 30 ml of dichloromethane
1.0 g of (4-bromophenyl) -2-methoxyacetic acid,
0.8 g of 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride was added. After stirring for 30 minutes, 0.63 g of 3-amino-3,4-dimethyl-2-pentanone was added. After stirring at room temperature for 5 hours, the reaction solution was poured into water and extracted with dichloromethane. After drying over anhydrous magnesium sulfate, dichloromethane was distilled off under reduced pressure. The residue was purified by silica gel column chromatography, and 0.36 g (yield 25%) of diastereomer A (low-polar substance) of the target compound having a melting point of 71 to 72 ° C and a target compound having a refractive index of 1.5321 (20 ° C) were obtained. Of diastereomer B (highly polar substance) in an amount of 0.17 g (yield: 12%). Optical purity: diastereomer A = 97.0%
e. e. , Diastereomer B = 99.2% e. e.
(High performance liquid chromatography, Daicel Chiral Cell O
D)

Examples of the compounds of the present invention produced according to the methods shown in Production Examples 1 to 9 are shown in Tables 23 to 28 together with the compounds shown in the above Production Examples.

It should be noted that isomer A indicates diastereomer A, isomer B indicates diastereomer B, and isomer M indicates a diastereomer mixture. Isomer RA refers to diastereomer A in which the acid moiety is optically active (R), isomer RB refers to diastereomer-B in which the acid moiety is optically active (R), and isomer RM "" Means a diastereomer mixture in which the acid moiety is an optically active form (R). Isomer SA refers to diastereomer A in which the acid moiety is optically active (S), isomer SB refers to diastereomer B in which the acid moiety is optically active (S), and isomer SM and Represents a diastereomer mixture in which the acid moiety is the optically active form (S). Diastereomer A refers to a low-polarity diastereomer separated by silica gel column chromatography or high performance liquid chromatography, and diastereomer B refers to a high-polarity diastereomer similarly separated. Show.

[0101]

[Table 23]

[0102]

[Table 24]

[0103]

[Table 25]

[0104]

[Table 26]

[0105]

[Table 27]

[0106]

[Table 28]

The fungicide for agricultural and horticultural use of the present invention comprises an arylacetic acid amide derivative represented by the general formula [1] as an active ingredient. When the compound of the present invention is used as an agricultural and horticultural fungicide, the active ingredient can be used in an appropriate dosage form according to the purpose. Usually the active ingredient is diluted with an inert liquid or solid carrier and, if necessary, a surfactant,
In addition to the above, it can be used in the form of powders, wettable powders, emulsions, granules and the like.

Examples of suitable carriers include solid carriers such as talc, bentonite, clay, kaolin, diatomaceous earth, white carbon, vermiculite, slaked lime, silica sand, ammonium sulfate, and urea; and liquid carriers such as isopropyl alcohol, xylene, cyclohexanone, and methylnaphthalene. And the like. As the surfactant and dispersant, for example, dinaphthyl methanesulfonate, alcohol sulfate, alkylaryl sulfonate, lignin sulfonate,
Polyoxyethylene glycol ether, polyoxyethylene alkyl aryl ether, polyoxyethylene sorbitan monoalkylate and the like can be mentioned. Examples of the auxiliary include carboxymethyl cellulose. These preparations are diluted to an appropriate concentration and sprayed or applied directly.

The fungicide for agricultural and horticultural use of the present invention can be used by foliage application, soil application or water surface application. The compounding ratio of the active ingredient is appropriately selected according to need, but is 0.1 to 20% (by weight) in the case of powder and granules, and 5 to 80% (by weight) in the case of emulsion and wettable powder. Appropriate.

The application rate of the agricultural and horticultural fungicide of the present invention varies depending on the kind of the compound used, the target disease, the tendency to occur, the degree of damage, the environmental conditions, the dosage form used, and the like. For example, when used as is, such as powders and granules,
The active ingredient may be appropriately selected from the range of 0.1 g to 5 kg, preferably 1 g to 1 kg per 10 ares. When used in liquid form such as emulsions and wettable powders, 0.1
ppm to 10,000 ppm, preferably 1 to 3000 ppm
It is preferable to appropriately select from the range of 0 ppm.

The compounds according to the invention can be used according to the above-mentioned application forms, for example, algal fungi (Oomycetes), ascomycetes (Asc)
omycetes), deuteromycetes (Deuteromy)
cetes), and Basidiomycete
tes) can be controlled. Next, specific bacterial names are given as non-limiting examples. Genus Pseudoperonospora (Pseudoperonospora),
For example, downy mildew (Pseudoperonospora)
cubensis), sphaeroteca (Sphaero)
theca), such as powdery mildew (Sphaero)
theca fuliginea), Venturia (V
enturia), such as the scab fungus (Venturi)
a inaequalis), Pyricularia (Pyr)
icularia), such as blast fungus (Pyric)
ularia oryzae), Gibberella (Gibbe)
rella), for example, Gibberel
la fujikuroi, Botrytis (Botry)
tis) genus, for example, Botrytis
cinerea), Alternari (Alternari)
a) Genus, for example, Komatsuna black spot fungus (Alternar)
ia brassicicola), Rhizoctonia (R
genus hizoctonia, for example, Rhizobium (Rhiz)
octonia solani), pacnia (Puc)
cinia) genus, for example, rust fungus (Puccinia)
recondita).

Further, the compound of the present invention may be mixed with an insecticide, other fungicides, herbicides, plant growth regulators, fertilizers and the like, if necessary. Next, the formulation method will be specifically described with reference to typical formulation examples of the agricultural and horticultural fungicides of the present invention. In the following description, “%” indicates weight percentage.

Formulation Example 1 Dust 2% of compound (B-3), 5% of diatomaceous earth, and 93% of Cray-93 were uniformly mixed and pulverized to give a dust.

Formulation Example 2 Wettable powder 50% of the compound (A-31), 45% of diatomaceous earth, 2% of sodium dinaphthylmethanedisulfonate and 3% of sodium ligninsulfonate were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 3 Emulsion 30% of compound (A-65), 20% of cyclohexanone,
11% polyoxyethylene alkyl aryl ether,
An emulsion was prepared by uniformly dissolving 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene.

Formulation Example 4 Granules Compound (A-21) 5%, lauryl alcohol sulfate sodium salt 2%, lignin sulfonate sodium 5%, carboxymethyl cellulose 2% and clay 8
6% is uniformly mixed and pulverized. The mixture was kneaded by adding an amount of water equivalent to 20%, processed into granules of 14 to 32 mesh using an extrusion granulator, and then dried to obtain granules.

Next, the effect of the fungicide for agricultural and horticultural use of the present invention will be specifically described with reference to test examples.

Test Example 1 Test for Rice Blast Preventive Effect About 1 paddy rice seed (variety: Asahi Aichi) was placed in a clay pot with a diameter of 7 cm.
Five seeds were sowed and grown in a greenhouse for 2 to 3 weeks. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and the rice seedling having the fourth leaf completely developed was sprayed with 10 ml per pot. After air-drying, a conidia suspension of rice blast fungus (Pyricularia oryzae) was sprayed and inoculated, and immediately placed in a moist chamber at 25 ° C for 24 hours.
I put the time. Thereafter, they were transferred to a greenhouse, and the number of lesions on the fourth leaf was examined 5 days after the inoculation. The control value was determined from Equation 1 and Table 29 was obtained.
Tables 30 to 33 show the results of evaluation according to the above criteria.

[0119]

(Equation 1)

[0120]

[Table 29]

[0121]

[Table 30]

[0122]

[Table 31]

[0123]

[Table 32]

[0124]

[Table 33]

Test Example 2 Rice Blast Water Surface Application Test Rice seedlings (variety: Asahi Asahi) at the 1.5 leaf stage were transplanted to four locations of three stems each at four places in a white porcelain bowl having a diameter of 9 cm and grown in a greenhouse. The wettable powder prepared according to Formulation Example 2 at the 2.5 leaf stage was subjected to water application to a pot such that the active ingredient concentration was 300 g per 10 ares. Ten days after the treatment, a conidia suspension of rice blast fungus (Pyricularia oryzae) was spray-inoculated and immediately placed in a 25 ° C moist chamber for 24 hours. Then, they were transferred to a greenhouse, and five days after the inoculation, the number of lesions on the highest leaf at the time of the inoculation was examined. The control value was determined by Equation 1, and the results evaluated according to the criteria in Table 29 are shown in Tables 34 to 35
It was shown to.

[0126]

[Table 34]

[0127]

[Table 35]

Test Example 3 Apple Scab Prevention Effect Test Apple seeds (variety: Kodama) in a 9 cm × 9 cm PVC bowl
Were sown five by five and grown in a greenhouse for 20 days. A wettable powder prepared according to Formulation Example 2 was diluted with water so that the active ingredient concentration became 500 ppm, and sprayed 20 ml per pot onto the seedlings in which four true leaves had been developed. After air-drying, a spore suspension of apple scab (Venturia inaequalis) was spray-inoculated and immediately placed in a moist chamber at 22 ° C for 48 hours.
I put the time. Thereafter, the apple seedlings were transferred to a greenhouse to cause disease, and 14 days after inoculation, the diseased area of the top two leaves at the time of inoculation was examined. Based on the criteria shown in Table 36, the disease severity was evaluated, and from the disease severity and the number of corresponding leaves, the damage degree was determined by Equation 2, and the control value was further determined by Equation 3. The resulting control values were evaluated based on the criteria in Table 29, and the results are shown in Table 37.

[0129]

[Table 36]

[0130]

(Equation 2)

[0131]

(Equation 3)

[0132]

[Table 37]

[0133]

The compound of the present invention has a high control effect against rice blast, apple scab and the like, and also has the characteristics of being excellent in residual effect and rain resistance without causing phytotoxicity to crops. Because they have both, they are useful as agricultural and horticultural fungicides.

──────────────────────────────────────────────────続 き Continued on the front page (51) Int.Cl. ⁶ Identification code FI A01N 37/38 A01N 37/38 37/44 37/44 37/46 37/46 47/04 47/04 C07C 233/51 C07C 233 / 51 235/34 235/34 237/22 237/22 255/29 255/29 323/60 323/60 323/62 323/62 (72) Inventor Junko Suzuki 408, Shioda, Fukuda-machi, Fukuda-gun, Iwata-gun, Shizuoka (1) Inside KI Research Institute Co., Ltd. (72) Atsushi Yasuda, Inventor 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka Prefecture Inside (72) Inventor Katsumi Furuse, Kamo Kikugawa-cho, Ogasa-gun, Shizuoka Prefecture 1809 (72) Inventor Kazuo Kumakura 532-1, Morishita, Toyota-machi, Iwata-gun, Shizuoka Prefecture (72) Inventor Ichiro Miura 18-9, 3-9-1 Kitamachi, Furukawa-shi, Miyagi Prefecture 11 at 3-15, Kuzugaoka

Claims (5)

[Claims] 1. A compound of the general formula [1] [Wherein the phenyl group A is substituted by _{X n, X n}
Represents has been or 2-naphthyl group substituted by may 1-naphthyl group or _{X n} to be replaced by, X is a halogen _atom, C 1 -C ₆ alkyl _group, C 2 -C ₆ alkenyl _{group, C} 2 ~ C ₆ alkynyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C ₄ haloalkyl group, hydroxy group, C
₁ -C ₆ alkoxy _group, C 2 -C ₆ alkenyloxy _group, C 2 -C ₆ alkynyloxy _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ haloalkoxy group, a phenoxy group (said group A C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom.), A C ₁ -C ₆ alkylthio group, ₁ -C ₄ haloalkylthio group, phenylthio group (in which is substituted by _C 1 -C ₆ alkyl _group, C 1 -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom An amino group, a C ₁ -C ₆ alkylamino group, a C ₁ -C ₆ dialkylamino group, a cyano group,
A phenyl group (the group is a C ₁ -C ₆ alkyl group, a C ₁ -C ₄
Haloalkyl group, C ₁ -C ₆ alkoxy group, cyano group,
It may be substituted by a nitro group or a halogen atom. ), An aralkyl group (the group is a C ₁ -C ₆ alkyl group,
C ₁ -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy group,
It may be substituted by a cyano group, a nitro group or a halogen atom. ), A C ₁ -C ₆ alkylcarbonyl group, a benzoyl group (the group is a C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom. May be substituted.)
Or a C ₁ -C ₆ alkoxycarbonyl group, wherein n is 1
And R ¹ represents a halogen atom, a C ₁ -C ₆ alkoxy group, a C ₃ -C ₆ cycloalkoxy group, a C ₁ -C
₄ haloalkoxy _groups, C 1 -C ₆ alkylthio group, _{C 1}
Represents a C ₁ to C ₆ alkylamino group or a C _{1 to} C ₆ dialkylamino group, and R ² represents a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆
Represents a cycloalkyl group or a C ₁ -C ₄ haloalkyl group, wherein R ³ is a C ₂ -C ₆ alkyl group, a C ₂ -C ₆ alkenyl group, a C ₃ -C ₆ cycloalkyl group (the group is a C ₁ -C ₆
It may be substituted by an alkyl group or a halogen atom. ) Or _C 1 -C ₄ haloalkyl group, or ^{R 2} and ^{R 3} combine to form a cycloalkyl group (in which the 5-membered to 7-membered ring together with the carbon atom _C 1 -C ₆ alkyl group, a halogen atom And Q may be a cyano group or a group —COR ⁴ (R ⁴ is a C ₁ -C ⁴
₆ alkyl group, C ₃ -C ₆ cycloalkyl group, C ₁ -C
₄ haloalkyl _groups, C 1 -C ₆ alkoxy _group, C 2 -C
₆ alkenyloxy group, C ₂ -C ₆ alkynyloxy group, C ₃ -C ₆ cycloalkyloxy group, amino group, C
₁ -C represents a ₆ alkylamino group or a _C 1 -C ₆ dialkylamino group. ). The arylacetic acid amide derivative represented by these. In 2. A general formula [1], A represents a phenyl group, which may be substituted also a 2-naphthyl group by or 1-naphthyl group or X _n to be replaced by X _n replaced by X _n , X represents a halogen atom, a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a C ₃ -C ₆ cycloalkyloxy group, ₁ -C ₄ haloalkoxy _{group, C} 1 ~
A C ₆ alkylthio group, a C ₁ -C ₄ haloalkylthio group or a phenyl group (the group may be a C ₁ -C ₆ alkyl group, a C ₁ -C
₄ haloalkyl groups, C ₁ -C ₆ alkoxy group, a cyano group, may be substituted by nitro group or a halogen atom. ) Represents, n represents an integer of 1 to 3, ^{R 1} is a halogen _atom, C 1 -C ₆ alkoxy _group, C 3 -C ₆ cycloalkoxy _group, C 1 -C ₄ haloalkoxy _groups, C 1 -C ₆
An alkylthio group, a C ₁ -C ₆ alkylamino group or C ₁
Represents a C ₁ to C ₆ dialkylamino group, and R ² represents a C _{1 to} C ₆ alkyl group, a C _{3 to} C ₆ cycloalkyl group or a C _{1 to} C ₄
Represents a haloalkyl group, R ³ is a C ₂ -C ₆ alkyl group,
C ₂ -C ₆ alkenyl _group, C 3 -C ₆ cycloalkyl group (said group _C 1 -C ₆ alkyl group may be substituted by a halogen atom.) Or an _C 1 -C ₄ haloalkyl group, or R ² and R ³ are a 5- to 7-membered cycloalkyl group together with the carbon atom to which they are attached (the group is a C ₁ -C ₆
It may be substituted by an alkyl group or a halogen atom. Q is a cyano group or a group -COR
^{4 (R 4} is _C 1 -C ₆ alkyl _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy _group, C 2 -C ₆ alkenyloxy _{group, C} 2 ~ C ₆
Alkynyloxy _group, C 3 -C ₆ cycloalkyloxy group, an amino _group, C 1 -C ₆ alkylamino group or a _C 1 ~
Represents a C ₆ dialkylamino group. ). 3. In the general formula [1], A represents a phenyl group, 1-naphthyl group or 2-naphthyl group substituted by _Xn , X represents a halogen atom, a C ₁ -C ₆ alkyl group, C ₃
-C ₆ cycloalkyl group, C ₁ -C ₄ haloalkyl group,
C ₁ -C ₆ alkoxy _group, C 3 -C ₆ cycloalkyl _group, C 1 -C ₄ haloalkoxy _groups, C 1 -C ₆ alkylthio _group, C 1 -C ₄ haloalkylthio group or a phenyl group (said group A C ₁ -C ₆ alkyl group, a C ₁ -C ₄ haloalkyl group, a C ₁ -C ₆ alkoxy group, a cyano group, a nitro group or a halogen atom.), And n is an integer of 1-3 R ¹ represents a halogen atom, C ¹
₁ -C ₆ alkoxy _group, a C 3 -C ₆ cycloalkoxy _group, C 1 -C ₄ haloalkoxy groups, or _C 1 -C ₆ alkylthio group, ^{R 2} represents a _C 1 -C ₆ alkyl group,
R ³ represents a C ₂ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group (the group may be substituted by a C ₁ -C ₆ alkyl group or a halogen atom) or a C ₁ -C ₄ haloalkyl group. Or R ² and R ³ are a 5- to 7-membered cycloalkyl group together with the carbon atom to which they are attached (the group is a C ₁ to C
It may be substituted by a C ₆ alkyl group or a halogen atom. Q is a cyano group or a group -COR
^{4. An} arylacetic acid amide derivative, wherein R ⁴ represents a C ₁ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group, a C ₁ -C ₄ haloalkyl group or a C ₁ -C ₆ alkoxy group. 4. In the general formula [1], A represents a phenyl group or a 2-naphthyl group substituted by _Xn , and X represents a halogen atom, a C ₁ -C ₆ alkyl group, or a C ₁ -C ₄ haloalkyl group. , A C ₁ -C ₆ alkoxy group, a C ₁ -C ₄ haloalkoxy group or a phenyl group (the group is a C ₁ -C ₆ alkyl group,
C ₁ -C ₄ haloalkyl _groups, C 1 -C ₆ alkoxy group,
It may be substituted by a cyano group, a nitro group or a halogen atom. N represents an integer of 1 to 3, R ¹ represents a halogen atom or a C ₁ -C ₆ alkoxy group, and R ² represents
Represents a C ₁ -C ₆ alkyl group, R ³ represents a C ₂ -C ₆ alkyl group, a C ₃ -C ₆ cycloalkyl group (the group is a C ₁ -C ₆ alkyl group).
_{6 It} may be substituted by an alkyl group or a halogen atom. ) Or _C 1 -C ₄ haloalkyl group, or ^{R 2} and ^{R 3} combine to form a cycloalkyl group (in which the 5-membered to 7-membered ring together with the carbon atom _C 1 -C ₆ alkyl group, a halogen atom And Q may be a cyano group or a group —COR ⁴ (R ⁴ is a C ₁ -C ⁴
Represents a ₆ alkyl group or a C ₁ -C ₆ alkoxy group. ). 5. A fungicide for agricultural and horticultural use containing the arylacetic acid amide derivative according to claim 1, 2, 3, or 4 as an active ingredient.