JPH10182616A - Amino acid amide derivative, and agricultural and horticultural fungicide - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain a new compound effective for agricultural and horticultural fungicides harmless to useful crops, having germicidal actions and excellently treating activity against tomato late blight, comprising an alkylamine connected to a condensed hetero ring such as a benzothiazole ring as an amine part. SOLUTION: This new compound is shown by formula I [R is a 1-6C alkyl, a 3-6C cycloalkyl, etc.; Y is a 2-3C alkylene; Z is a 3-5C alkylene; Het is a group of formula II (X is a halogen, methyl, etc.; (n) is 0-2), etc.] such a N<1> -[2-(6- fluorobenzothiazol-2-yl)ethyl]-N<2> -isopropoxycarbnonyl)-L-valina-mide. An amino acid derivative of formula III is reacted with an amine of the formula NH2 -Y- Het in the presence of a catalyst such as 4-dimethylamionpyridine and a base such as KOH to give a compound of formula I. Preferably, the reaction is carried out in a reaction temperature in a range of 75-100 deg.C for 1-20 hours.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

TECHNICAL FIELD The present invention relates to an amino acid amide derivative and an agricultural and horticultural fungicide containing the same as an active ingredient.

[0002]

BACKGROUND ART Already, N 1 ^- [1- (2- furanyl) ethyl] -N 2 ^- amino acid amide derivatives such as phenoxycarbonyl -L- valinamide are known to be useful as fungicides (JP JP-A-3-153657). ^Further, N 1 - [1- (2- benzothiazolyl)
^Ethyl] -N 2-tert-butoxycarbonyl -L-
Amino acid amide derivatives such as valinamide are known to be useful as fungicides (International Publication No. 9604).
252). However, the compound of the present invention and its bactericidal activity are not yet known.

[0003]

When a fungicide is used repeatedly, a resistant bacterium against the drug may appear and a sufficient control effect may not be exhibited. Also, due to environmental problems, a new fungicide that can efficiently control harmful bacteria at a low concentration is required. Therefore, the present invention has solved such a problem.
It is intended to provide an amino acid amide derivative having a novel and excellent bactericidal activity.

[0004]

DISCLOSURE OF THE INVENTION In order to develop a fungicide for agricultural and horticultural use having a controlling effect superior to that of a conventionally known fungicide, the present inventors have developed an alkyl group having a fused heterocyclic ring such as a benzothiazole ring. Various amino acid amide derivatives having an amine as an amine moiety were synthesized, and their bactericidal activity was examined. As a result, the compound of the present invention has high prophylactic activity against tomato late blight, grape downy mildew, cucumber downy mildew, potato late blight, and tomato late blight, grape downy mildew,
The present inventors have found that they have excellent therapeutic activity against cucumber downy mildew and the like and do not cause any harm to useful crops, and have completed the present invention based on these findings.

[0005] The present invention relates to the general formula

[0006]

Embedded image [In the formula, R is a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group (the group is the same or different halogen atom, methyl group or A methoxy group may be substituted at one or more places) or an aralkyl group (the group is a halogen atom,
It may be substituted with a methyl group or a methoxy group. Y represents a linear or branched alkylene group having 2 to 3 carbon atoms, and Z represents a branched alkyl group having 3 to 5 carbon atoms or a cycloalkyl group having 3 to 5 carbon atoms. Represent, Het
Is the expression

[0007]

Embedded image In the formula, X represents a halogen atom, a methyl group, a methoxy group or a trifluoromethyl group, and n represents 0 or an integer of 1 to 2. Represents｝. And a fungicide for agricultural and horticultural use containing the amino acid amide derivative as an active ingredient.

The compound of the present invention represented by the general formula [I]
Having one or more asymmetric carbon atoms in the molecule, these compounds have various diastereomers and enantiomers which can be resolved in an appropriate manner. Pure individual diastereomers, enantiomers and mixtures thereof are also included in the compounds of the present invention.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION In the general formula [I], preferred compounds are those in which R is a branched alkyl group or phenyl group having 3 to 4 carbon atoms, Y is a group —CH ₂ CH ₂ —, and Z is Compounds having an isopropyl group, Het being a benzothiazol-2-yl group, X being a halogen atom, n being 0 or 1, and an amino acid in L form can be mentioned. Particularly preferred compounds are N ^1- [2- (6-fluoro-2-
Benzothiazolyl) ethyl] -N ² - is isopropoxycarbonyl -L- valinamide.

Next, specific examples of the compound of the present invention represented by the general formula [I] are shown in Tables 1 to 5. However, the compounds of the present invention are not limited to these compounds. The compound numbers will be referred to in the following description.

[0011]

[Table 1]

[0012]

[Table 2]

[0013]

[Table 3]

[0014]

[Table 4]

[0015]

[Table 5]

In the table, compounds 10, 11, 12 and 13 are DL-amino acid amide derivatives, and the other compounds are L-amino acid amide derivatives.

The compound of the present invention represented by the general formula [I] is
For example, it can be manufactured according to the following manufacturing method. <Production method A>

[0018]

Embedded image (In the formula, R, Y, Z and Het represent the same meaning as described above.)

The compound of the present invention represented by the general formula [I]
Reaction of an amino acid derivative represented by the general formula [II] or a compound having its carboxyl group activated with an amine represented by the general formula [III] in the presence or absence of a catalyst and / or a base It can be manufactured by doing.

In this reaction, the compound in which the carboxyl group of the amino acid derivative represented by the general formula [II] is activated includes, for example, an acid halide such as an acid chloride, an amino acid represented by the general formula [II] An acid anhydride obtained by dehydration-condensation of two molecules of a derivative, a mixed acid anhydride composed of an amino acid derivative represented by the general formula [II] and another acid or O-alkyl carbonate, p-nitrophenyl ester, 2- Activated esters such as tetrahydropyranyl ester and 2-pyridyl ester can be exemplified.

This reaction is carried out using N, N'-dicyclohexylcarbodiimide, carbonyldiimidazole,
It can also be carried out using a condensing agent such as -chloro-1,3-dimethylimidazolium chloride.

The solvent that can be used in this reaction may be any solvent that does not inhibit the reaction, for example, hydrocarbons such as pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, dichloromethane, Dichloroethane, chloroform,
Halogenated hydrocarbons such as carbon tetrachloride, chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, acetone, methyl ethyl ketone, methyl isopropyl ketone,
Ketones such as methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; nitriles such as acetonitrile, propionitrile and benzonitrile; and aprotic polar solvents such as dimethyl sulfoxide, dimethylformamide and sulfolane; and A mixed solvent obtained by combining solvents selected from the following 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, further, triethylamine, trimethylamine, dimethylaniline , Pyridine, N-methylpiperidine, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN),
1,8-diazabicyclo [5.4.0] undec-7-
Organic bases such as ene (DBU) and the like are preferable, and tertiary amines such as triethylamine, pyridine and N-methylpiperidine are preferable.

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

The reaction temperature ranges from -75 ° C to 100 ° C,
It is preferably carried out in the range of -60C to 40C.
The reaction time is preferably 1 to 20 hours.

The compound represented by the general formula [II] as a raw material is, for example, L-valine and dicarbonate di (tert).
-Butyl) in the presence of sodium hydrogen carbonate to give N-tert-butoxycarbonyl-L-
It can be manufactured as valine. Moreover, it can be produced as N-benzyloxycarbonyl-DL-valine by reacting DL-valine with carbobenzoxycyclolide in the presence of sodium hydrogen carbonate.
These are already known methods [Methoden del Organischen Chemie
er Organischen Chemie), 1st
Vol. 5, No. 2, page 2; Georg Thieme Vermek Stuttgart (Georg Thieme Ver.)
lagStattgart (1974), Chemistry of the Amino Acids (Chemistr)
y of the Amino Acids), 2nd
Vol. 891, John Wiley and Sons,
New York (John Wiley & Sons,
N. Y. ) (1964), Journal of the American Chemical Society (Journal)
of the American Chemical
Society, Vol. 79, p. 4686 (1957)
Year)〕.

Among the compounds in which the carboxyl group of these amino acid derivatives is activated, for example, a mixed acid anhydride is
It can be produced by reacting the amino acid derivative represented by the general formula [II] with isobutyl chloroformate in the presence of an organic base. The p-nitrophenyl ester can be produced by reacting the amino acid derivative represented by the general formula [II] with p-nitrophenol in the presence of a condensing agent. These are already known methods [Methoden der Organis hemi.
chen Chemie), Vol. 15, No. 2, No. 2
Page; Georg Thieme Verlag Stut
tgart) (1974), Chemische Berichte, 38.
Vol. 605 (1905), Journal of the American Chemical Society (Journa)
l of the American Chemica
l Society), Vol. 74, p. 676 (195
2 years), Journal of the American Chemical Society (Journal of the Am
erican Chemical Society),
86, 1839 (1964)].

<Production method B>

[0029]

Embedded image (In the formula, R, Y, Z and Het represent the same meaning as described above, and L represents a halogen atom or a group ROC (O) O-.)

The compound of the present invention represented by the general formula [I]
An amine represented by the general formula [V] or an inorganic acid salt such as a hydrochloride thereof, or an organic acid salt such as a tosylate in the presence or absence of a compound represented by the general formula [IV] Can be produced by reacting

The solvent which can be used in the present reaction may be any solvent which does not inhibit the reaction, for example, pentane, hexane, heptane, cyclohexane, petroleum ether, ligroin, hydrocarbons such as benzene, toluene and xylene, dichloromethane, Dichloroethane, chloroform,
Halogenated hydrocarbons such as carbon tetrachloride, chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, ethylene glycol dimethyl ether, tetrahydrofuran and dioxane, acetone, methyl ethyl ketone, methyl isopropyl ketone,
Ketones such as methyl isobutyl ketone; acetates such as methyl acetate and ethyl acetate; nitriles such as acetonitrile, propionitrile and benzonitrile; aprotic polar solvents such as dimethyl sulfoxide, dimethylformamide and sulfolane; water; and A mixed solvent obtained by combining solvents selected from the following can be used.

As the base, those generally used in this type of reaction can be used. For example, sodium hydroxide, alkali metal hydroxides such as potassium hydroxide, alkaline earth metal hydroxides such as calcium hydroxide, sodium carbonate, alkali metal carbonates such as potassium carbonate, further, triethylamine, trimethylamine, dimethyl Aniline, N-methylmorpholine, pyridine, N-methylpiperidine, 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), 1,8-diazabicyclo [5.4.0] undec-7 And organic bases such as -ene (DBU). Preferably triethylamine, N-
Tertiary amines such as methylmorpholine, pyridine and N-methylpiperidine are exemplified. Reaction temperature is -20 ° C
To 100 ° C, preferably 0 ° C to 40 ° C. The reaction time is preferably 30 minutes to 20 hours.

The intermediate of the general formula [II] which is an intermediate of the compound of the present invention:
The amines represented by the formula I] are described, for example, in JP-A-8-176.
It can be produced in accordance with the specification of JP-A-115-115 and JP-A-8-198865.

The compound of the general formula [V] which is an intermediate of the compound of the present invention
For example, a fused heterocyclic derivative represented by the formula (I) can be obtained by converting a carbamic acid ester of the compound [I] synthesized by the method of Production Method A into a generally known method for removing an amino protecting group of an amino acid, for example, It can be produced by a catalytic reduction method or a treatment with an acid such as liquid hydrogen fluoride, sulfonic acids, hydrogen chloride, hydrogen bromide and formic acid.

Next, a production example of a compound represented by the general formula [III] which is an intermediate of the compound of the present invention will be described as a reference example.

Reference Example 1 Preparation of 2- (6-fluorobenzothiazol-2-yl) ethylamine N-tert-butoxycarbonyl-β-alanine
8 g was dissolved in 100 ml of tetrahydrofuran, and 7 g of carbonyldiimidazole was added little by little. After stirring for 30 minutes, 6 g of 2-amino-5-fluorothiophenol was added to the reaction solution, and the mixture was heated under reflux for 3 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate.
The solvent was distilled off under reduced pressure, and the obtained residue was purified by silica gel column chromatography to obtain 3.5 g of tert-butyl N- [2- (6-fluorobenzothiazol-2-yl) ethyl] carbamate as crystals. (Melting point 74-75
° C). Further, 3.5 g of the obtained crystals were dissolved in 50 ml of ethyl acetate, and hydrogen chloride gas was blown in for 3 hours. After completion of the reaction, the solvent was distilled off under reduced pressure, and the obtained crude crystals were washed with ethyl acetate, and 2- (6-fluorobenzothiazol-2-yl) ethylamine hydrochloride 2.5
g (26% yield).

Reference Example 2 Production of 2- (5-chlorobenzofuran-2-yl) ethylamine N-tert-butoxycarbonyl-β-alanine
6 g was dissolved in 50 ml of tetrahydrofuran, and 2.2 g of carbonyldiimidazole was added little by little. After stirring for 30 minutes, the solution was added to (5-chloro-2-hydroxyphenyl) methyltriphenylphosphonium bromide 6
g was added and stirred at room temperature for 1 hour. Then, 1.3 g of triethylamine was added, and the mixture was heated under reflux for 1 hour. After cooling,
The resulting crystals were separated by filtration, the filtrate was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography.
0.7 g of tert-butyl N- [2- (5-chlorobenzofuran-2-yl) ethyl] carbamate (mp 80
８１81 ° C.). Furthermore, 0.6 g of the obtained crystals
Was dissolved in 20 ml of dichloromethane, and hydrogen chloride gas was added in 3 ml.
I blew the time. After completion of the reaction, the solvent was distilled off under reduced pressure,
The obtained crude crystals were washed with ethyl acetate, melting point 229-2.
0.5 g (yield 20%) of 2- (5-chlorobenzofuran-2-yl) ethylamine hydrochloride showing 34 ° C was obtained.

Next, a production example of a compound represented by the general formula [V] which is an intermediate of the compound of the present invention will be described.

[0039] (Reference Example ^{3) N 1 - [2- (} 6- fluoro-benzothiazol-2-yl) ethyl] -L- valinamide manufacturing N ^{2-tert-butoxycarbonyl -N} 1 - [2-
(6-Fluorobenzothiazol-2-yl) ethyl]
1.7 g of -L-valinamide was dissolved in 50 ml of ethyl acetate, and hydrogen chloride gas was introduced at room temperature for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure and the resulting crude crystals were washed with ethyl acetate, N 1 ^- [2- (6- fluoro-benzothiazol-2-yl) ethyl] -L- valinamide hydrochloride 1.4 g (100% yield) were obtained.

[0040]

EXAMPLES Next, the production method, formulation method and use of the compound of the present invention will be specifically described with reference to examples.

(Production Example 1) Production of N ^1- [2- (6-fluorobenzothiazol-2-yl) ethyl] -N ² -isopropoxycarbonyl) -L-valinamide (Compound No. 6) N ^1- [ 2- (6-Fluorobenzothiazol-2-yl) ethyl] -L-valinamide hydrochloride (0.5 g) is suspended in tetrahydrofuran (30 ml), N-methylmorpholine (0.5 g) is added at -20 ° C, and the mixture is heated at this temperature for 10 minutes. Stirred. Then isopropyl chloroformate at -20 ° C.
2 g was added, and the mixture was stirred at room temperature for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate.
Washing was carried out in the order of a 5% aqueous sodium hydrogen carbonate solution and water. Further, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude crystals were purified by silica gel column chromatography to obtain 0.5 g of the desired product as a white powder.
(87% yield).

(Production Example 2) N ² -tert-butoxycarbonyl-N ^1- [3- (benzothiazol-2-yl) propyl] -L-valinamide (Compound No. 39)
Production of 0.3 g of N-tert-butoxycarbonyl-L-valine was dissolved in 25 ml of tetrahydrofuran, 0.15 g of N-methylpiperidine was added at −20 ° C., and then 0.2 g of isobutyl chloroformate was added. Furthermore, -60 ° C
In this reaction solution is added 3- (benzothiazol-2-yl)
0.3 g of propylamine was added, and the mixture was stirred at room temperature for 5 hours. After completion of the reaction, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with 2N hydrochloric acid, a 5% aqueous sodium hydrogen carbonate solution and water in this order. Further, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The obtained crude crystals were purified by silica gel column chromatography to obtain 0.3 g (yield 48%) of the target compound as colorless granular crystals.

The fungicide for agricultural and horticultural use of the present invention comprises an amino acid amide derivative represented by the general formula [I] 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 and the like can be added to the active ingredient to be used in the form of powders, wettable powders, emulsions, granules and the like.

Suitable carriers include, for example, 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 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 of occurrence, 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, cucumber downy mildew (Pseudoperonos)
Pora cubensis, Fight ftora (Ph
ytophthora), for example, tomato late blight (P
hyphothora infestans, Plasmopara genus, such as grape downy mildew (Plasmopara viticol)
a).

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 A compound (2), 2% of diatomaceous earth and Cle-93% were uniformly mixed and pulverized to give a dust.

Formulation Example 2 Wettable powder 50% of compound (3), 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 (6), 20% of cyclohexanone, 11% of polyoxyethylene alkylaryl ether, 4% of calcium alkylbenzenesulfonate and 35% of methylnaphthalene were uniformly dissolved to form an emulsion.

Formulation Example 4 Granules Compound (8) 5%, sodium salt of lauryl alcohol sulfate 2%, sodium lignin sulfonate 5
%, Carboxymethylcellulose 2% and clay 86%
Is uniformly mixed and pulverized. 20% of water was added to the mixture, and the mixture was kneaded, 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 Cucumber Downy Mildew Preventive Effect Test Cucumber seeds (variety: 9 cm × 9 cm)
(Sagami Hanjiro) were sowed at 10 grains and grown in a greenhouse for 7 days. The wettable powder prepared according to Formulation Example 2 was diluted with water to 500 ppm of the active ingredient to cucumber seedlings in which cotyledons had developed, and 10 ml per pot was sprayed. After air drying,
Cucumber downy mildew (Pseudoperonospor)
a cubensis) was spray-inoculated and immediately placed in a humidity chamber at 22 ° C. for 24 hours. After that, they were transferred to a greenhouse, and 7 days after inoculation, the diseased area of the entire pot was investigated.
The evaluation was based on the criteria in Table 6. The results are shown in Table 7.

[0054]

[Table 6]

[0055]

[Table 7]

Test Example 2 Cucumber downy mildew treatment effect test Cucumber seeds (variety: 9 cm × 9 cm)
(Sagami Hanjiro) were sowed at 10 grains and grown in a greenhouse for 7 days. Cucumber seedlings that have developed cotyledons are planted with cucumber downy mildew (Pseudoperonospora cuben)
sis) by spray inoculation with a zoosporangial suspension, immediately at 22 ° C.
For 24 hours. After air-drying, the wettable powder prepared according to Formulation Example 2 was diluted with water to 500 ppm with an active ingredient, and 10 ml was sprayed per pot. After that, they were transferred to a greenhouse, and 7 days after inoculation, the diseased area of the entire pot was investigated.
The evaluation was based on the criteria in Table 6. The results are shown in Table 8.

[0057]

[Table 8]

[0058]

INDUSTRIAL APPLICABILITY The agricultural and horticultural fungicide of the present invention has a high preventive effect against cucumber downy mildew, and is also effective against tomato late blight, grape downy mildew and potato late blight. Also, by treating the agricultural and horticultural fungicide of the present invention after the pathogen invades the plant body, an excellent control effect is exhibited. In addition, it does not cause phytotoxicity to crops, and has excellent characteristics of systemic migration, residual effect, and rain resistance.

────────────────────────────────────────────────── ─── Continued on the front page (51) Int.Cl. ⁶ Identification code FI C07D 277/64 C07D 277/64 307/81 307/81 333/58 333/58 333/62 333/62 333/64 333/64 (72) Inventor Norihisa Yonekura 408-1, Shioda, Fukuda-cho, Iwata-gun, Shizuoka Pref. Inside the K-I Research Institute Co., Ltd. ) Inventor Yoshiyuki Kojima 69 Takagosho, Kakegawa City, Shizuoka Prefecture (72) Inventor Kenichi Muramatsu 3-15-15, Kuzugaoka, Kakegawa City, Shizuoka Prefecture

Claims (3)

[Claims] 1. A compound of the general formula [In the formula, R is a linear or branched alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, a phenyl group (the group is the same or different halogen atom, methyl group or A methoxy group may be substituted at one or more places) or an aralkyl group (the group is a halogen atom,
It may be substituted with a methyl group or a methoxy group. Y represents a linear or branched alkylene group having 2 to 3 carbon atoms, and Z represents a branched alkyl group having 3 to 5 carbon atoms or a cycloalkyl group having 3 to 5 carbon atoms. Represent, Het
Is the formula In the formula, X represents a halogen atom, a methyl group, a methoxy group or a trifluoromethyl group, and n represents 0 or an integer of 1 to 2. Represents｝. ] The amino acid amide derivative shown by these. 2. A compound of the general formula [In the formula, R is a branched alkyl group having 3 to 4 carbon atoms, a cycloalkyl group having 4 to 6 carbon atoms, a phenyl group (the groups are the same or different and are a halogen atom, a methyl group or a methoxy group. May be substituted at one or more positions) or an aralkyl group (the group may be substituted with a halogen atom, a methyl group or a methoxy group), and Y is a straight-chain having 2 to 3 carbon atoms. Represents a chain or branched alkylene group,
Z represents a branched alkyl group having 3 to 4 carbon atoms or a cycloalkyl group having 3 to 5 carbon atoms, and Het is represented by the formula: In the formula, X represents a halogen atom, a methyl group, a methoxy group or a trifluoromethyl group, and n represents 0 or an integer of 1 to 2. Represents｝. ] The amino acid amide derivative shown by these. 3. A fungicide for agricultural and horticultural use comprising the amino acid amide derivative according to claim 1 as an active ingredient.