JPH07145156A - Thiazolecarboxylic acid amide derivative and agricultural and horticultural germicide containing the same as active component - Google Patents

Abstract

PURPOSE:To obtain a new thiazolecarboxylic acid amide derivative having a preventive effect on e.g. gray mold and powdery mildew of a crop such as cucumber or tomato and Brown rust of wheat and useful as an agricultural and horticultural germicide, etc. CONSTITUTION:A compound of formula I (R is H or methyl), e.g. N-(2- phenylphenyl)-2-methyl-4-trifluoromethylthiazole-5-carboxylic acid amide. In addition, the compound of formula I is produced by reacting a thiazolecarboxylic acid halide of formula II (X is a halogen) with 2-aminobiphenyl in the presence of a base such as triethylamine in a solvent such as THF.

Description

Detailed Description of the Invention

[0001]

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

[0002]

BACKGROUND OF THE INVENTION It has been widely known that a wide variety of carboxylic acid amides exhibit physiological activity as herbicides and fungicides. Among them, benzoic acid amides and heterocyclic carboxylic acid amides are not only patents, Many medicines are marketed as germicides. For example, as benzoic acid amide, 3′-isopropyloxy-2-methylbenzanilide, or α, α, α-trifluoro-
3'-Isopropyloxy-2-toluanilide is commercially available as a fungicide against rice blight, wheat rust and the like. Further, as the heterocyclic carboxylic acid amide, 5,6
-Dihydro-2-methyl-1,4-oxathiin-3-
Carboxanilide-4,4-dioxide is chrysanthemum white rust, 3,4-dihydro-6-methyl-2H-pyran-5.
-Carboxanilide is marketed as a fungicide against rust of wheat.

Further, in the case of Pestic. Sci. , 38 ,
1 to 7 (1993), thiazolecarboxylic acid amides inhibit the action of succinate dehydrogenase,
Having activity against Rhizoctonia
Aust. J. Chem. , 36 . 135-147 (1
983) describes that pyrazolecarboxylic acid amides likewise have activity against Rhizoctonia.

Further, Japanese Patent Application Laid-Open No. 5-221994 describes various heterocyclic carboxylic acid anilides including nicotinic acid anilides, among which the following general formulas (2) and (2) are shown. It is described that the thiazolecarboxylic acid amide derivative also has an effect on Botrytis bacteria.

[0005]

[Chemical 2]

Wherein A is thiazol-5-yl substituted by hydrogen, methyl, chlorine, trifluoromethyl at the 2- and 4-positions, hydrogen, methyl, chlorine, trifluoro at the 2- and 5-positions. Means thiazol-4-yl substituted by methyl, R being C ₂ -C ₁₂ alkyl optionally substituted by halogen, C ₃ -optionally substituted by halogen
C ₁₂ alkenyl, C ₃ -C ₆ alkynyl, C ₂ -C ₁₂ alkoxy optionally substituted with halogen, C ₃ -C ₁₂ alkenyloxy optionally substituted with halogen, C ₃ -C ₁₂ alkynyloxy, C ₄ -C ₆ optionally substituted with C ₁ -C ₄ alkyl
Cycloalkyl, optionally C ₁ -C ₄ optionally substituted by alkyl C ₄ -C ₆ cycloalkenyl, optionally C ₁ -C ₄ alkyl optionally substituted C ₅ -C ₆ cycloalkyloxy, C ₅ -C ₆ cycloalkenyloxy optionally substituted with C ₁ -C ₄ alkyl, optionally C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁
To C ₄ alkylthio and phenyl optionally substituted with halogen, respectively)

However, the bactericidal activity of the thiazoles specifically disclosed in the examples of the present invention is that thiazol-5-yl in which A is substituted with a trifluoromethyl group at the 4-position is used. , And R is an alkyl group. Further, in this publication, R is a phenyl group,
Although the case of a fluorine-substituted phenyl group is also described in the table, the examples show that A is a thiazol-5-yl group substituted with a methyl group at the 4-position, and R is This is only one example in the case of a phenyl group. Moreover, no bactericidal activity is shown in this example either.
The present inventors tested the fungicidal activity of the compounds specifically disclosed in the Examples and the compounds in the table, but the control effect was low and not practical.

[0008]

SUMMARY OF THE INVENTION An object of the present invention is to provide an agricultural and horticultural fungicide which exhibits an excellent bactericidal effect as compared with the prior art and is safe against crops.

[0009]

Means and Actions for Solving the Problems In order to solve the above problems, the present inventors further researched a thiazolecarboxylic acid amide derivative. As a result, a novel thiazolecarboxylic acid amide derivative having a trifluoromethyl group at the 4-position of the thiazole ring and an amine moiety of 2-aminobiphenyl is disclosed in the above-mentioned JP-A-5-221994.
The present invention has been completed by finding that a new bactericidal effect which cannot be predicted from the content described in the publication is exhibited. That is, the present invention provides a compound represented by the general formula (1)

[0010]

[Chemical 3]

A thiazolecarboxylic acid amide derivative represented by the formula (wherein R represents a hydrogen atom or a methyl group) and an agricultural and horticultural fungicide containing the thiazolecarboxylic acid amide derivative as an active ingredient.

The compound of the present invention is characterized in that a trifluoromethyl group is introduced at the 4-position of the thiazole ring and 2-aminobiphenyl is introduced at the amine portion. On the other hand, Japanese Patent Application Laid-Open No. Hei 5-221994 discloses the following general formula (2)
It is described that the thiazolecarboxylic acid amide derivative shown in (Chemical Formula 4) has an effect on Botrytis bacteria.

[0013]

[Chemical 4]

Where A is water at the 2- and 4-positions.
Replaced by elemental, methyl, chlorine, trifluoromethyl
Thiazol-5-yl, 2- and 5-position odors
Replaced by hydrogen, methyl, chlorine, trifluoromethyl
Is thiazol-4-yl, where R is
More optionally C substituted with halogen₂~ C₁₂Archi
C, optionally substituted with halogen, optionally halogen₃~
C₁₂Alkenyl, C₃~ C ₆Alkynyl, optionally halo
C optionally substituted with gen₂~ C₁₂Alkoxy, place
Optionally substituted by halogen C₃~ C₁₂A
Lucenyloxy, C₃~ C₁₂Alkynyloxy, in some cases
Than C₁~ C_FourC optionally substituted with alkyl_Four~ C₆
Cycloalkyl, optionally C₁~ C_FourSubstituted with alkyl
May be C_Four~ C₆Cycloalkenyl, optionally
C₁~ C_FourC optionally substituted with alkyl_Five~ C₆Shiku
Roalkyloxy, optionally C₁~ C_FourSubstitute with alkyl
May be C_Five~ C₆Cycloalkenyloxy, field
C in combination₁~ C_FourAlkyl, C₁~ C_FourAlkoxy, C₁
~ C_FourAlkylthio, optionally substituted with halogen
Each means phenyl)

That is, JP-A 5-221,994 contains the compound of the present invention as a superordinate concept. However, although this publication claims a very broad range of compounds, the example compounds are limited. For example, regarding the compound represented by the general formula (II), it is shown that bactericidal effect is thiazol-5-yl in which A is substituted with a trifluoromethyl group at the 4-position, and R
Is limited to an alkyl group. Also, (a) A is 4-
Thiazol-5-yl substituted in position by a trifluoromethyl group, and R is a fluorine-substituted phenyl group, and (b) A thiazol-5-yl substituted in position 4-by a methyl group. And the case where R is a phenyl group is described in the table, but only one example of (b) is shown in the examples. Moreover, no bactericidal activity is shown in this example either. The present inventors tested the bactericidal activity of the disclosed compounds of the examples and the compounds in the table, but the control effect was low and not practical.

Therefore, the compound of the present invention is thiazole-5.
-In the carboxamide, a trifluoromethyl group is introduced at the 4-position of the thiazole ring, and 2
-Characterized by the introduction of aminobiphenyl. The significance of introducing these specific groups is great, and the compounds of the present invention, which are described in the above-mentioned prior art and JP-A-5-221994, show almost no control effect or only extremely weak effect. It was found that it has an excellent control effect against plant diseases that cannot be predicted at all.
The thiazolecarboxylic acid amide derivative represented by the general formula (1) of the present invention is a novel compound and has the following reaction formula (1)
It is manufactured by the method shown in Chemical formula 5.

[0017]

[Chemical 5]

(Wherein X represents a halogen atom and R is the same as above), that is, the thiazolecarboxylic acid halide represented by the general formula (3) and 2-aminobiphenyl are melted or in a solvent. It can be produced by reacting.

The solvent used in this reaction may be any solvent inert to the reaction, for example, aromatic compounds such as benzene, toluene, chlorobenzene, ethers such as dioxane, tetrahydrofuran, diethyl ether, ethyl acetate, etc. Ester, dichloromethane, chloroform, 1,2-dichloroethane and other halogenated hydrocarbons,
Examples include aprotic polar solvents such as dimethylformamide and dimethylsulfoxide.

This reaction may also be carried out in the presence of a base, and examples of the base include triethylamine, pyridine,
Examples thereof include organic bases such as N, N-dimethylaniline and inorganic bases such as sodium hydride, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydrogen carbonate. The reaction temperature is 0 to 150 ° C. The carboxylic acid halide of the general formula (4) is produced by a known method.

The agricultural and horticultural fungicides containing the compound represented by the general formula (1) of the present invention as an active ingredient are cucumber,
Excellent against gray mold of various crops such as tomato, strawberry, grape, cucumber powdery mildew, barley powdery mildew, wheat powdery mildew, strawberry powdery mildew, grape powdery mildew, apple powdery mildew, wheat leaf rust, etc. Shows the control effect.

When the compound represented by the general formula (1) according to the present invention is used as an agricultural and horticultural fungicide, the raw material may be used as it is for the plant to be treated, but it is generally inactive. It is mixed with various liquid carriers or solid carriers and used as a commonly used formulation such as powders, wettable powders, flowables, emulsions, granules and other commonly used formulations. Further, an auxiliary agent can be added if necessary for formulation.

The term "carrier" as used herein means a synthetic or natural inorganic or organic substance that is formulated to help the active ingredient reach the site to be treated and to facilitate storage, transportation and handling of the active ingredient compound. Means The carrier may be either solid or liquid as long as it is usually used for agricultural and horticultural agents, and is not limited to a particular carrier.

Examples of solid carriers include clays such as montmorillonite and kaolinite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean powder, sawdust, and wheat flour. The plant-based organic substances and urea, etc.

Liquid carriers include toluene, xylene,
Aromatic hydrocarbons such as cumene, kerosene, paraffinic hydrocarbons such as mineral oil, ketones such as acetone and methyl ethyl ketone, ethers such as dioxane and diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, propanol and ethylene glycol, Examples thereof include dimethylformamide, dimethylsulfoxide, water and the like.

Further, in order to enhance the potency of the compound of the present invention, the following auxiliary agents may be used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene and the like. . As the auxiliary agent, a surfactant, a binder (for example, ligninsulfonic acid, alginic acid, polyvinyl alcohol, gum arabic, CMC sodium, etc.) usually used in agricultural and horticultural chemicals, a stabilizer (for example, phenol for antioxidant) Compounds, thiol compounds or higher fatty acid esters, phosphates as pH adjusters, and sometimes light stabilizers), etc., can be used alone or in combination as required. Further, in some cases, an industrial bactericidal agent, an antibacterial and antifungal agent, etc. may be added for antibacterial and antifungal agents.

The auxiliary agent will be described in more detail. Emulsification,
Anionic interfaces such as lignin sulfonate, alkylbenzene sulfonate, alkyl sulfate ester salt, polyoxyalkylene alkyl sulfate salt, polyoxyalkylene alkyl phosphate ester salt for the purpose of dispersing, spreading, wetting, binding, stabilizing, etc. Activator, polyoxyalkylene alkyl ether, polyoxyalkylene alkyl aryl ether, polyoxyalkylene alkyl amine, polyoxyalkylene alkyl amide, polyoxyalkylene alkyl amide, polyoxyalkylene alkyl thioether, polyoxyalkylene fatty acid ester, glycerin fatty acid ester, Nonionic surfactant such as sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, polyoxypropylene polyoxyethylene block polymer Agents, calcium stearate, lubricants such as wax, stabilizers such as isopropyl hydroperoxide diene phosphate, other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, these components are not limited to the above.

The content of the compound represented by the general formula (1) in the fungicide for agricultural and horticultural use according to the present invention varies depending on the formulation form, but is usually 0.05 to 20% by weight in a dusting agent,
The wettable powder is 0.1 to 80% by weight, the emulsion is 1 to 50% by weight, the flowable formulation is 1 to 50% by weight, and the dry flowable formulation is 1 to 80% by weight, and preferably 0.5 for powders. -5% by weight, wettable powder 5-80% by weight, granules 0.5-8% by weight, emulsion 5-20% by weight, flowable formulation 5-30% by weight and dry flowable formulation 5-5% by weight. It is 50% by weight.

The content of the auxiliary agent is 0 to 80% by weight,
The content of the carrier is 100% by weight minus the contents of the active ingredient compound and the auxiliary agent.

Examples of the application method of the composition of the present invention include seed disinfection, foliage spraying, etc., but any application method usually used by those skilled in the art exerts sufficient efficacy. The application rate and application concentration vary depending on the target crop, target disease, degree of disease occurrence, compound dosage form, application method and various environmental conditions, but when sprayed, the amount of active ingredient is 50 to 1,000 g per hectare. Is suitable, and preferably 100 to 500 g per hectare. When a wettable powder, a flowable agent or an emulsion is diluted with water and sprayed, the dilution ratio is appropriately 200 to 20,000 times, and preferably 1,000 to 5,000 times.

The agricultural and horticultural fungicides of the present invention can be used not only as a mixture with other fungicides, insecticides, herbicides and plant growth regulators as pesticides, soil conditioners or fertilizers, but also with them. Mixed formulations are also possible. Examples of the fungicides include triadimefon, hexaconazole, prochloraz, azole fungicides such as triflumizole, metalaxyl, acylalanine fungicides such as oxadixyl, thiophanate methyl, benzimidazole fungicides such as benomyl, manzeb and the like. Examples of the dithiocarbamate fungicides and tetrachloroisophthalonitrile, sulfur and the like, insecticides such as fenitrothion, diazinon, pyridafenthion, chlorpyrifos, marathon,
Fentate, dimethoate, methylthiomethone, prothiophos, DDVP, acephate, salicione, E
Examples include phosphorus insecticides such as PN, carbamate insecticides such as NAC, MTMC, BPMC, pirimicarb, carbosulfan, and mesomil, and pyrethroid insecticides such as etofenprox, permethrin, and fenvalerate, but are not limited thereto. It is not something that will be done.

[0032]

EXAMPLES Next, the production method of the compound of the present invention will be specifically described with reference to examples. Example 1 Preparation of N- (2-phenylphenyl) -2-methyl-4-trifluoromethylthiazole-5-carboxylic acid amide (Compound 1) 2-Methyl-4-trifluoromethylthiazole-5-
4 g of carboxylic acid was suspended in 50 ml of toluene, 4.74 g of phosphorus pentachloride was charged therein, and the mixture was heated under reflux for 3 hours for chlorination, and the solvent was distilled off under reduced pressure. Tetrahydrofuran (30 ml) and pyridine (1.8 g) were added to the precipitate, and 2-aminodiphenyl (3.56 g) was added with stirring at room temperature, followed by stirring for 2 hours. After the reaction, the mixture is discharged into water, extracted with ethyl acetate, the organic layer is washed with 2N-hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by column chromatography on silica gel to obtain 5.3 g of the desired product (yield 73%). mp: 121.6 to 122.8 ° C ¹ H-NMR (CDCl ₃ , δ value): 2.70 (3H, s), 7.22 to 7.51 (m, 8H), 7.7
3 (brs, 1H), 8.34 (d, J = 8.8,1H), IR (cm ^-1 ): 3273,1681,1520,1173,755

Example 2 Preparation of N- (2-phenylphenyl) -4-trifluoromethylthiazole-5-carboxylic acid amide (Compound 2) In Example 1, 4-trifluoromethylthiazole-5-as the carboxylic acid. The target product was obtained in exactly the same manner except that carboxylic acid was used (yield 70%). mp: 117-120 ° C ¹ H-NMR (CDCl ₃ , δ value): 7.25-7.32 (m, 2H), 7.35-7.38 (m, 2
H), 7.41 ~ 7.45 (m, 4H) 7.81 (brs, 1H), 8.37 (d, J = 8.1,1H), 8.81 (s, 1H) IR (cm ^-1 ): 3242,3070,1651,1548, 1510,1190,1132,750

Reference Example 1 N- (2-fluorophenylphenyl) -2-methyl-
4-Trifluoromethylthiazole-5-carboxylic acid amide (reference compound A) In Example 1, 2'-fluoro-2- as the amine
The same method was used except that aminodiphenyl was used. mp: 98.5-100.3 ° C ¹ H-NMR (CDCl ₃ , δ value): 2.76 (s, 3H), 7.15-7.24 (m, 2H), 7.3
0〜7.77 (m, 6H), 7.86 (brs, 1H) IR (cm ^-1 ): 3293,1657,1601,1556,1359,991,758

Reference Example 2 N- (2-isopropylphenyl) -2-methyl-4-
Trifluoromethylthiazole-5-carboxylic acid amide (control compound B) The procedure of Example 1 was repeated except that 2-isopropylaniline was used as the amine. mp: 114.0-115.2 ° C ¹ H-NMR (CDCl ₃ , δ value): 1.25 (d, J = 6.6,6H), 2.77 (s, 3H), 3.0
4 (septet, J = 6.6,1H) 7.24 ~ 7.27 (m, 2H), 7.29 ~ 7.36 (m, 1H), 7.58 ~ 7.69 (m, 1H) 7.73 (brs, 1H) IR (cm ^-1 ): 3205 , 2968,1649,1561,1527,1173,1131

Reference Example 3 N- (2-phenylphenyl) -2,4-dimethylthiazole-5-carboxylic acid amide (control compound C) In Example 1, 2,4-dimethylthiazole-5-carboxylic acid was used as the carboxylic acid. The procedure was exactly the same except that an acid was used. mp: 132-133 ° C ¹ H-NMR (CDCl ₃ , δ value): 2.34 (s, 3H), 2.62 (s, 3H), 7.17-7.2
9 (m, 3H), 7.37 ~ 7.77 (m, 6H), 8.42 (d, J = 8.1,1H) IR (cm ^-1 ): 3373,1667,1525,1310,1177,755

Formulation Examples and Physiological Test Examples Formulation examples and test examples of the fungicide for agricultural and horticultural use according to the present invention are shown below. Formulation Example 1 Dust 3 parts of compound No. 1, 20 parts of diatomaceous earth, 3 parts of clay
0 parts and 47 parts of talc are uniformly pulverized and mixed to give a powder 10
I got 0 copies.

Formulation Example 2 Wettable Powder 30 parts of the compound of Compound No. 2, 47 parts of diatomaceous earth, 20 parts of white clay, 1 part of sodium lignin sulfonate and 2 parts of sodium alkylbenzene sulfonate are uniformly pulverized and mixed to prepare a wettable powder 100. I got a part.

Formulation Example 3 Emulsion 10 parts of the compound of Compound No. 1, 10 parts of cyclohexane,
50 parts of xylene and 20 parts of sorbole (surfactant manufactured by Toho Kagaku) were uniformly dissolved and mixed to obtain 100 parts of emulsion.

Formulation Example 4 Wettable Powder 50 parts of the compound of Compound No. 1, 40 parts of talc, 5 parts of sodium lauryl phosphate and 5 parts of sodium alkylnaphthalene sulfonate were mixed to obtain 100 parts of a wettable powder.

Formulation Example 5 Wettable powder 50 parts of the compound of Compound No. 1, 10 parts of sodium lignin sulfonate, 5 parts of sodium alkylnaphthalene sulfonate, 10 parts of white carbon and 25 diatomaceous earth
Parts were mixed and pulverized to obtain 100 parts of a wettable powder.

Formulation Example 6 Floating Agent 40 parts of the compound of Compound No. 1, 3 parts of carboxymethyl cellulose, 2 parts of sodium lignin sulfonate, 1 part of dioctyl sulfosuccinate sodium salt and 54 parts of water.
Part is wet pulverized with a sand grinder, and a flowable agent 1
I got 00 parts.

Next, the efficacy of the compound of the present invention as an agricultural and horticultural fungicide will be described with reference to test examples. In addition, in the test example, the compound of the above reference example was used as a control agent.

Test Example 1 Test for controlling green mold disease of kidney bean According to Formulation Example 5, kidney beans (variety: Tsurunashi Top Crop) were grown in a greenhouse in a 7.5 cm diameter vinyl pot until two cotyledons were developed. The wettable powder prepared as described above was diluted to a predetermined concentration and sprayed at 50 ml per 4 pots. After the drug solution was air-dried, a conidial suspension (1 × 10 ⁵ cells / m 2) prepared from Botrytis cinerea cultivated on PDA medium was used.
l) is spray-inoculated on the cotyledon, 20-23 ° C, humidity 95%
It was kept in the above greenhouse for 7 days. Seven days after the inoculation, the area occupied by gray mold disease lesions per leaf of kidney bean was investigated according to the following indexes. The results are shown in Table 1 (Table 1).

Severity 0: No illness 1: Area of disease group is 5% or less 2: Area of disease group is 5 to 25% 3: Area of disease group is 25 to 50% 4: Area of disease group is 50% The control value (%) where the average value of each of the treated and non-treated plots is the degree of disease control = (1-the degree of disease of the treated group / the degree of disease of the untreated group) × 100

[0046]

[Table 1]

Test Example 2 Cucumber Powdery Mildew Control Effect Test For the first leaf stage seedlings of cucumber (variety: Forcing Nippon) grown in a 7.5 cm diameter vinyl pot in a greenhouse, two plants each were prepared according to Formulation Example 5. The wettable powder prepared as described above was diluted to a predetermined concentration and sprayed at 50 ml per 4 pots. After the drug solution was air-dried, the cucumber powdery mildew spores that had been generated on the cucumber leaves in advance were gently shaken on the leaves to inoculate. Ten days after the inoculation, the area occupied by powdery mildew disease groups per cucumber leaf was investigated according to the following index. The results are shown in Table 2 (Table 2).

Degree of illness 0: No illness 1: Area of illness is 5% or less 2: Area of illness is 5 to 25% 3: Area of illness is 25 to 50% 4: Area of illness is 50% The control value (%) where the average value of each of the treated and non-treated plots is the degree of disease control = (1-the degree of disease of the treated group / the degree of disease of the untreated group) × 100

[0049]

[Table 2] In the table, ₊ to ₊₊ indicate the degree of chemical damage (whitening). No mark indicates no drug damage.

The results of Test Examples 1 and 2 are obtained by using the general formula (1).
It is shown that the compound of the present invention represented by the formula (3) has an excellent control effect against cucumber gray mold and cucumber powdery mildew as compared with the control compound, and is safe against crops. Such a result is completely unexpected from the above prior art.

[0051]

The fungicide for agricultural and horticultural use containing the compound represented by the general formula (1) of the present invention as an active ingredient is a gray mold disease of various crops such as cucumber, tomato, strawberry and grape.
Cucumber powdery mildew, barley powdery mildew, wheat powdery mildew, strawberry powdery mildew, grape powdery mildew, apple powdery mildew, wheat powder rust, etc., showing an excellent control effect against
It is useful as a fungicide for agriculture and horticulture.

 ─────────────────────────────────────────────────── ─── Continuation of front page (72) Inventor Yuji Yanase 1144 Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd. (72) Atsushi Takashi 1144 Togo, Mobara-shi, Chiba Mitsui Toatsu Chem.

Claims (3)

[Claims] 1. A general formula (1) (Chemical Formula 1): (In the formula, R represents a hydrogen atom or a methyl group) A thiazolecarboxylic acid amide derivative. 2. An agricultural and horticultural fungicide containing the compound of general formula (1) according to claim 1 as an active ingredient. 3. A method for controlling plant diseases, which comprises applying the compound of general formula (1) according to claim 1 to plant pathogenic fungi or their habitat.