JPH09132567A - Pyrazolecarboxylic acid anilide derivative and agricultural and horticultural fungicide comprising the same as active ingredient - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain the subject compound useful as an agricultural and horticultural fungicide excellent in fungicidal effect, and safe to crops. SOLUTION: This pyrazolecarboxylic acid anilide derivative is shown by formula I (the position of a trifluoromethyl group is the 3- or 4-position; X is H or a halogen) such as N-(4-chloro-3-trifluoromethylphenyl)-1-methyl-3- trifuloromethylpyrazoel-4-carboxylic acid anilide. The compound of formula I is obtained by reacting a pyrazolecarboxylic acid chloride of formula II with an aniline of formula III such as 2-(4-chloro-3-trifluorophenyl)aniline in a molten state or in a solvent such as benzene at 0-150 deg.C. The compound of formula I as agricultural and horticultural fungicide is mixed with an inert liquid carrier or solid carrier and is preferably used in the dosage form such as powder, wettable powder, flowable agent, emulsion, granule, etc.

Description

Detailed Description of the Invention

[0001]

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

[0002]

2. Description of the Related Art It has been conventionally known that pyrazolecarboxylic acid anilide exhibits bactericidal activity. For example, Aus
t. J. Chem. , 36 . 135-147 (198
3) and JP-A-52-87168, it is described that pyrazolecarboxylic acid anilides have activity against Rhizoctonia.
Japanese Patent No. 316559 discloses that pyrazole carboxylic acid anilides have activity against ocular disease of wheat.

Recently, it has been described that a certain kind of heterocyclic carboxylic acid anilide has an effect on Botrytis bacterium, and the pyrazole carboxylic acid anilide is also included therein. For example, JP-A-5-22199
No. 4 discloses various heterocyclic carboxylic acid anilides.
It is described that it has an effect on Botrytis bacterium, and among them, a pyrazolecarboxylic acid anilide derivative represented by the following general formula (2) (chemical formula 2) is also included.

[0004]

Embedded image (In the formula, R ¹ represents a methyl group or a trifluoromethyl group, R ² represents a methyl group or a chlorine atom, and R ³ is C ₂ -C ₁₂ alkyl optionally substituted with halogen, optionally C ₃ optionally substituted by halogen
To C ₁₂ alkenyl, C _{3 to} C ₆ alkynyl, C _{2 to} C ₁₂ alkoxy optionally substituted with halogen,
C ₃ -C ₁₂ optionally substituted by halogen
Alkenyloxy, C ₃ -C ₁₂ alkynyloxy, optionally C ₁ -C ₄ alkyl C ³ optionally substituted with ~
C ₆ cycloalkyl, optionally C ₁ -C ₄ alkyl optionally substituted C ₄ even though -C ₆ cycloalkenyl, optionally C ₁ -C ₄ optionally substituted by alkyl C ₅ -C ₆
Cycloalkyloxy, optionally C ₁ -C ₄ alkyl substituted optionally C ₅ -C ₆ cycloalkenyloxy, optionally C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio However, the 5-position of the pyrazole ring of the present invention is a methyl group or a chlorine atom and does not include a hydrogen atom. The inventors tested the disclosed compounds of the Examples for bactericidal activity, but had little control effect and were not practical.

Further, Japanese Unexamined Patent Publication (Kokai) No. 6-199803 describes that heterocyclic carboxylic acid anilides have an effect on Botrytis bacterium, and among them, the compounds represented by the following general formula (3) (formula 3) are shown. Also included are pyrazole carboxylic acid anilide derivatives.

[0006]

Embedded image (In the formula, R ⁴ is a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group, and R ⁵ is a partially or completely halogenated C ₃ -C ₁₂ alkyl group, C ₂ ~ C
₁₂ alkoxy groups, C ₃ -C ₁₂ alkenyl groups, C ₃ -C
₁₂ alkenyloxy groups, C ₃ -C ₆ alkynyl groups, C
The ₃ -C ₆ alkynyloxy group, 1 to 3 C ₁ -C good C ₃ also have an alkyl group having ₄ -C ₇ cycloalkyl group, cycloalkenyl group C ₄ -C _7, C cycloalkyloxy group ₃ -C _7, cycloalkyl group of C ₄ -C _7, 1 to 5 halogens and / or one to three C ₁ -C ₄ alkyl, haloalkyl C ₁ -C ₄ Base, C ₁
To C ₄ alkoxy group, C _{1 to} C ₄ haloalkoxy group,
(C _{1 to} C ₄ alkylthio group and C _{1 to} C ₄ phenyl group which may have a haloalkylthio group, respectively) As described above, this publication claims a very wide range of compounds. The example compounds in the publication are limited. For example, regarding the compound represented by the general formula (3), R ⁵
Is a substituted phenyl group, the substituents of the phenyl group specifically disclosed in the examples and tables of the publication are hydrogen atom, halogen atom, methyl group and methoxy group, and haloalkyl such as trifluoromethyl group. Those containing groups are not shown. Further, the present inventors tested the bactericidal activity of the compounds disclosed in the Examples of the above publications, but they showed almost no control effect and were not practical.

[0007]

Judging from the above-mentioned conventional techniques, the object of the present invention is to provide an agricultural and horticultural fungicide which exhibits an excellent bactericidal effect and is safe for crops. is there.

[0008]

[Means for Solving the Problems] In order to solve the above problems, the present inventors further researched a pyrazolecarboxylic acid anilide derivative. As a result, the novel pyrazole carboxylic acid anilide derivative in which the aniline moiety is a biphenylamine having a trifluoromethyl group is disclosed in the above-mentioned JP-A-5-221994 and JP-A-6-19980.
The present invention has been completed by finding that a new bactericidal effect that cannot be predicted from the content described in Japanese Patent No. 3 is exhibited.

[0009]

BEST MODE FOR CARRYING OUT THE INVENTION That is, the present invention is based on the general formula (1)
(Chemical formula 4)

[0010]

Embedded image (In the formula, the position of the trifluoromethyl group is the 3-position or 4-position, and X represents a hydrogen atom or a halogen atom), and a pyrazolecarboxylic acid anilide derivative represented by the formula, and agricultural and horticultural sterilization containing the same. Regarding agents.

The compound of the present invention is characterized in that the aniline moiety is biphenylamine having a trifluoromethyl group. On the other hand, JP-A-5-221994 describes that a pyrazolecarboxylic acid anilide derivative represented by the following general formula (2) (formula 5) has an effect on Botrytis bacterium.

[0012]

Embedded image (In the formula, R ¹ represents a methyl group or a trifluoromethyl group, R ² represents a methyl group or a chlorine atom, and R ³ is C ₂ -C ₁₂ alkyl optionally substituted with halogen, optionally C ₃ optionally substituted by halogen
To C ₁₂ alkenyl, C _{3 to} C ₆ alkynyl, C _{2 to} C ₁₂ alkoxy optionally substituted with halogen,
C ₃ -C ₁₂ optionally substituted by halogen
Alkenyloxy, C ₃ -C ₁₂ alkynyloxy, optionally C ₁ -C ₄ alkyl C ³ optionally substituted with ~
C ₆ cycloalkyl, optionally C ₁ -C ₄ alkyl optionally substituted C ₄ even though -C ₆ cycloalkenyl, optionally C ₁ -C ₄ optionally substituted by alkyl C ₅ -C ₆
Cycloalkyloxy, optionally C ₁ -C ₄ alkyl substituted optionally C ₅ -C ₆ cycloalkenyloxy, optionally C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio However, the 5-position of the pyrazole ring of the present invention is a methyl group or a chlorine atom and does not include a hydrogen atom. The inventors tested the disclosed compounds of the Examples for bactericidal activity, but had little control effect and were not practical.

Further, Japanese Unexamined Patent Publication (Kokai) No. 6-199,803 also describes that heterocyclic carboxylic acid anilides have an effect on Botrytis bacteria. Among them, the following general formula (3) The indicated pyrazole carboxylic acid anilide derivative is also included.

[0014]

[Chemical 6] (In the formula, R ⁴ is a C ₁ -C ₄ alkyl group or a C ₁ -C ₄ haloalkyl group, and R ⁵ is a partially or completely halogenated C ₃ -C ₁₂ alkyl group, C ₂ ~ C
₁₂ alkoxy groups, C ₃ -C ₁₂ alkenyl groups, C ₃ -C
₁₂ alkenyloxy groups, C ₃ -C ₆ alkynyl groups, C
The ₃ -C ₆ alkynyloxy group, 1 to 3 C ₁ -C good C ₃ also have an alkyl group having ₄ -C ₇ cycloalkyl group, cycloalkenyl group C ₄ -C _7, C cycloalkyloxy group ₃ -C _7, cycloalkyl group of C ₄ -C _7, 1 to 5 halogens and / or one to three C ₁ -C ₄ alkyl, haloalkyl C ₁ -C ₄ Base, C ₁
To C ₄ alkoxy group, C _{1 to} C ₄ haloalkoxy group,
A C ₁ -C ₄ alkylthio group and a C ₁ -C ₄ phenyl group which may have a haloalkylthio group, respectively. That is, JP-A-6-199803 contains the compound of the present invention as a superordinate concept. To do. However, although this publication claims a very broad range of compounds, the example compounds of that publication are limited. For example, in the compound represented by the general formula (3), when R ⁵ is a substituted phenyl group, the substituent of the phenyl group specifically disclosed in Examples and Tables of the publication is a hydrogen atom or a halogen atom. , Methyl group,
Only a methoxy group is not shown that contains a haloalkyl group such as a trifluoromethyl group. The present inventors tested the bactericidal activity of the compounds disclosed in the Examples of the above publications as well as the compounds in the table, but they had almost no control effect and were not practical.

Therefore, the compound of the present invention is characterized in that the aniline moiety is biphenylamine having a trifluoromethyl group. The significance of introducing these specific groups is great, and the compounds of the present invention are disclosed in the above-mentioned prior art, JP-A 5-2.
It was found that the compounds described in 21994 and Japanese Patent Application Laid-Open No. 6-199803 have an excellent control effect that cannot be predicted at all against plant diseases that show almost no control effect.

The pyrazolecarboxylic acid anilide derivative represented by the general formula (1) of the present invention is a novel compound and is produced by the method shown in the following reaction formulas (4) and (7).

[0017]

Embedded image (In the formula, the position of the trifluoromethyl group is at the 3-position or 4-position, and X represents a hydrogen atom or a halogen atom.) That is, in the pyrazole carboxylic acid chloride of (4-1) and the general formula (4-2). It can be produced by reacting the represented anilines in a molten state or in a solvent.

Examples of the aniline derivative represented by the general formula (4-2) of the present invention include 2- (4-chloro-3-trifluorophenyl) aniline, 2- (4-trifluoromethylphenyl) aniline and 2 Examples include-(3-trifluoromethylphenyl) aniline and 2- (3-chloro-4-trifluoroomethylphenyl) aniline.

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 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 present invention is also an agricultural and horticultural fungicide containing the compound represented by the general formula (1) as an active ingredient.

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. And plant-derived organic substances and urea.

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 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. . Examples of the adjuvant include surfactants, binders (eg, ligninsulfonic acid, alginic acid, polyvinyl alcohol, gum arabic, sodium CMC, etc.) and stabilizers (eg, phenol for antioxidation, which are usually used in agricultural and horticultural drugs). Compounds, thiol compounds or higher fatty acid esters, phosphates as pH adjusters, and sometimes light stabilizers) can be used alone or in combination as necessary. 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 waxes, stabilizers such as isopropyl hydroperoxide diene phosphate, other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, these components are not limited to those described above.

The content of the compound represented by the general formula (1) in the agricultural and horticultural fungicide according to the present invention varies depending on the formulation form, but is usually 0.05 to 20% by weight for powders and 0.1 to 20 for wettable powders. 80% by weight, 0.05-30% by weight for granules, 1-50% by weight for emulsions, 1-50% by weight for flowable formulations, 1-80% by weight for dry flowable formulations, preferably 0.5- for powders. 5% by weight, 5-80% by weight of wettable powder,
Granules are 0.5 to 8% by weight, emulsions are 5 to 20% by weight, flowable formulations are 5 to 30% by weight, and dry flowable formulations are 5 to 50% by weight. Auxiliary agent content 0-80% 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 agricultural or horticultural chemical of the present invention include seed disinfection, foliar application, etc., but any application method usually used by those skilled in the art is sufficiently effective.
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 spraying, 50-1,000 g per hectare as the active ingredient amount. Suitable, preferably 100 to 500 g per hectare. When a wettable powder, a flowable agent or an emulsion is diluted with water and then sprayed, a dilution ratio of 200 to 20,000 is appropriate, preferably 1,00.
It is 0 to 5,000 times.

The agricultural and horticultural fungicides of the present invention can be used not only in combination with other fungicides, insecticides, herbicides, plant growth regulators and other pesticides, soil improvers or fertilizers, but also with these. 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. Dithiocarbamate fungicides and tetrachloroisophthalonitrile, sulfur and the like,
Examples of insecticides include 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. Not something that is done.

[0031]

EXAMPLES The production method of the compound of the present invention will be specifically described below with reference to examples.

Embodiment 1 Method for producing N- (4-chloro-3-trifluoromethylphenyl) -1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide [Compound No. 1] (1-1): 4-chloro-3 -Production of trifluoromethylphenylboric acid To 0.85 g of magnesium, 117 ml of a THF solution of 1M-borane and 7.5 g of 4-chloro-3-trifluoromethyl-1-bromobenzene were sequentially added under a nitrogen stream, and ultrasonic waves were applied. Was irradiated for 1 hour. The mixture was discharged into ice water, acidified with 5% hydrochloric acid, extracted with diethyl ether, and washed with saturated brine. After drying over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain the desired product as an oil.
5.0 g (quantitative).

(1-2): 2-nitro- (4-chloro-
Preparation of 3-trifluoromethylphenyl) benzene 2-bromonitrobenzene 1.0 in 50 ml toluene.
g, 4-chloro-3-trifluoromethylphenylboronic acid 1.66 g, 2M potassium carbonate aqueous solution 5 ml, and ethanol 2 ml were added, and the mixture was stirred under a nitrogen stream for 30 minutes.
0.28 g of Pd (PPh ₃ ) ₄ was added, and the mixture was heated under reflux for 3 hours. After separating the two layers, the organic layer was washed with water and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain the desired product as yellow crystals. 1.26 g (85% yield). ¹ H-NMR (CDCl ₃ , δ value): 7.40 to 7.71 (6H, m), 7.98 (1H, d, J =
7.3).

(1-3): Production of 2- (4-chloro-3-trifluoromethylphenyl) aniline 1.48 g of 2-nitro- (4-chloro-3-trifluoromethylphenyl) benzene, 5 ml of concentrated hydrochloric acid. Was added to 20 ml of methanol, 1.37 g of iron powder was added little by little, and the mixture was heated at 60 ° C. for 2 hours. The mixture was discharged into 50 ml of water, neutralized with sodium hydrogen carbonate, extracted with ethyl acetate, and washed with saturated brine. After drying over sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography to obtain the desired product as an oil. 0.71 g (57% yield). ¹ H-NMR (CDCl ₃ , δ value): 3.68 (2H, bs), 6.77 (1H, dd, J = 8.1,
1.5), 6.88 (1H, dd, J = 8.1,1.5), 7.07 (1H, dd, J = 8.1,1.
5), 7.19 (1H, dd, J = 8.1,1.5), 7.54 to 7.62 (2H, m), 7.80
(1H, s)

(1-4): Preparation of N- (4-chloro-3-trifluoromethylphenyl) -1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide 2- (4-chloro-3) -Trifluoromethylphenyl)
10 ml of pyridine in which 0.7 g of aniline was dissolved
, 3-trifluoromethyl-1-methylpyrazole-
0.55 g of 4-carboxylic acid chloride was added, and the mixture was stirred for 1 hour at room temperature. The mixture was discharged into a 5% aqueous hydrochloric acid solution, extracted with ethyl acetate, washed successively with saturated sodium hydrogen carbonate and saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography, and then crystallized with hexane to obtain the desired product as colorless crystals. 0.65 g (yield 56%). mp: 130.9-132.6 ° C ¹ H-NMR (CDCl ₃ , δ value): 3.95 (3H, s), 7.24-7.31 (2H, m), 7.
43 ~ 7.50 (3H, m), 7.58 (1H, d, J = 8.1), 7.71 (1H, d, J = 2.2),
7.90 (1H, s), 8.18 (1H, d, J = 8.1)

Example 2 Method for producing N- (4-trifluoromethylphenyl) -1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide [Compound No. 2] (2-1): 2-nitro Preparation of-(4-trifluoromethylphenyl) benzene In Example 1, 4-chloro-
3-trifluoromethylphenyl boric acid instead of 4-
Synthesis was carried out in exactly the same manner except that trifluoromethylphenyl boric acid was used. Yield 95%, oil. ¹ H-NMR (CDCl ₃ , δ value): 7.30 to 7.35 (1H, m), 7.42 to 7.47 (2
H, m), 7.55 (1H, dt, J = 8.1,1.5), 7.64 ~ 7.73 (3H, m), 7.94 (1
H, d, J = 8.1).

(2-2): Preparation of 2- (4-trifluoromethylphenyl) aniline In Example 1, 2-nitro- (4-chloro-3-trifluoromethylphenyl) benzene was replaced by 2-nitro. Synthesis was performed in exactly the same manner except that-(4-trifluoromethylphenyl) benzene was used. 72% yield,
oil.

(2-3): Preparation of N- (4-trifluoromethylphenyl) -1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide 2- (4-trifluoromethylphenyl) aniline
0.53 g of 3-trifluoromethyl-1-methylpyrazole-4-carboxylic acid chloride was added to 10 ml of pyridine in which 0.4 g was dissolved, and the mixture was stirred at room temperature for 1 hour. The mixture was discharged into a 5% aqueous hydrochloric acid solution, extracted with ethyl acetate, washed successively with saturated sodium hydrogen carbonate and saturated brine, and dried over sodium sulfate. The solvent was distilled off under reduced pressure, the residue was purified by silica gel column chromatography, and then crystallized with hexane to obtain the desired product as colorless crystals. 94% yield. mp: 156-158 ° C ¹ H-NMR (CDCl ₃ , δ value): 3.94 (3H, S), 7.42-7.55 (5H, m), 7.
70 (2H, d, J = 8.1), 7.88 (1H, S), 8.26 (2H, d, J = 8.1)

Next, formulation examples of the fungicide for agricultural and horticultural use according to the present invention are shown. Formulation Example 1 Dust agent 3 parts of the compound of Compound No. 1 described in Example 1, 20 parts of diatomaceous earth, 30 parts of clay and 47 parts of talc were uniformly pulverized and mixed to obtain 100 parts of a powder agent.

Formulation Example 2 Wettable powder 30 parts of the compound of Compound No. 2 described in Example 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 ground and mixed to obtain 100 parts of a wettable powder. Got

Formulation Example 3 Emulsion 10 parts of compound No. 1, cyclohexane 10 parts,
60 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 alkylnaphthalenesulfonate were mixed to obtain 100 parts of a wettable powder.

Formulation Example 5. Wettable powder 50 parts 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. FLOWABLE AGENT 40 parts 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 the test examples, the following compounds were used as control agents. Control compound 1. Procymidone, trade name: Sumirex, chemical name: N- (3,5-dichlorophenyl) -1,2-
Dimethylcyclopropane-1,2-dicarboximide Control compound 2. Compound (No. 41) described in JP-A-6-199803 Chemical name: N- (2-tolyl) -1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide Control compound 3. Compound described in JP-A-5-221994 (No. 5.10) Chemical name: N- (2-phenyl) -5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid anilide Control Compound 4. Triadimefone, trade name: Bayreton, chemical name: 1- (4-chlorophenoxy) -3,3-dimethyl-1- (1,2,4-triazol-1-yl)-
2-butanone

Test Example 1 Green Bean Mold Control Control Test (1) On green beans (variety: Tsurunashi Top Crop) grown in a greenhouse in a plastic pot having a diameter of 7.5 cm until two cotyledons were spread, Formulation Example 5 was prepared. The water-dispersible powder prepared according to 1. was diluted to a predetermined concentration and sprayed at 50 ml per 4 pots. A conidial suspension (1 × 10 ⁵ cells / ml) prepared from Botrytis cinerea (MBC resistant, RS bacterium) cultured on a PDA medium after the drug solution was dried was spray-inoculated on the cotyledons, and 20
It was kept in a greenhouse at -23 ° C and a humidity of 95% or more for 7 days. Seven days after the inoculation, the area occupied by gray mold disease lesions per leaf of kidney bean was investigated, and the degree of disease was determined according to the following index, and the average value of each treated group and untreated group was used as the degree of disease. The control value was calculated according to the following formula based on the obtained disease severity.
The results are shown in Table 1 (Table 1). Severity 0: No illness 1: Area of lesion is 5% or less 2: Area of lesion is 5 to 25% 3: Area of lesion is 25 to 50% 4: Area of lesion is 50% or more (each) The average value of the treated and non-treated plots was used as the disease severity.) Control value (%) = (1-treatment disease severity / untreated treatment risk) × 100

[0047]

[Table 1]

Test Example 2 Green Bean Mold Control Control Test (2) In a greenhouse (cultivar: Craneless Top Crop) grown in a plastic pot having a diameter of 7.5 cm, two cotyledons were grown, and Formulation Example 5 was used. The water-dispersible powder prepared according to 1. was diluted to a predetermined concentration and sprayed at 50 ml per 4 pots. Botrytis cinerea (MBC resistant / dicarboximide drug resistant, R
Conidial spore suspension (1 × 10 ⁵ cells / m) prepared from R bacteria
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 disease severity was determined and the control value was calculated in the same manner as in Test Example 1. The results are shown in Table 2 (Table 2).

[0049]

[Table 2]

Test Example 3 Cucumber powdery mildew control test 1.5 in a plastic pot with a diameter of 7.5 cm in a greenhouse
A wettable powder prepared according to Formulation Example 5 was diluted to a predetermined concentration in cucumbers (cultivar: Sagamihanjiro) that had been grown in duplicate until the leaf stage, and sprayed at 50 ml per 3 pots. After the drug solution dries, a conidia suspension prepared by suspending cucumber powdery mildew conidia in water containing a small amount of spreader (1 x
10 ⁶ cells / ml) were spray inoculated and kept in the greenhouse for 7 days. Seven days after the inoculation, the disease severity was determined and the control value was calculated in the same manner as in Test Example 1. The results are shown in Table 3 (Table 3).

[0051]

[Table 3]

Test Example 4 Wheat Leaf Rust Control Test Wheat (cultivar: Norin 6) grown in a plastic pot with a diameter of 6 cm in a greenhouse in an amount of 15 to 20 till 1.5 leaf stage
No. 4), the wettable powder prepared according to Formulation Example 5 was diluted to a predetermined concentration and sprayed at 50 ml per 3 pots. After the drug solution dried, summer spores of wheat leaf rust were sprayed and left in a humidified state for 2 days and then transferred to a room at 18 ° C. Ten days after the inoculation, the disease severity was determined in the same manner as in Test Example 1 and the control value was calculated. The results are shown in Table 4 (Table 4).

[0053]

[Table 4] The results of Test Examples 1 to 4 show that the compound of the present invention represented by the general formula (1) exhibits an excellent control effect against cucumber gray mold, cucumber powdery mildew and wheat leaf rust as compared with the control compound. Is shown. Such results are shown in the above-mentioned prior art, JP-A-5-221994 and JP-A-6-1994.
It is completely unpredictable from the contents of Japanese Patent Laid-Open No. 199803.

[0054]

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 or cucumber powdery mildew of various crops such as cucumber, tomato, strawberry and grape. , Has an excellent control effect against powdery mildew of wheat, strawberry powdery mildew, grape powdery mildew, apple powdery mildew, wheat leaf rust and the like, and is useful as a fungicide for agriculture and horticulture.

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

Claims (3)

[Claims] 1. A general formula (1) (Chemical Formula 1): (In the formula, the position of the trifluoromethyl group is at the 3- or 4-position, and X represents a hydrogen atom or a halogen atom), and a pyrazolecarboxylic acid anilide derivative. 2. An agricultural and horticultural fungicide containing the compound according to claim 1 as an active ingredient. 3. A method for controlling plant diseases, which comprises applying the compound according to claim 1 to plant pathogenic fungi or their habitat.