JPH064593B2 - Pyrazolcarboxamide derivative and fungicide containing the same as an active ingredient - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [In the formula, R ¹ and R ² each represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and at least one of R ^{1 and} R ² represents a trifluoromethyl group. ] The present invention relates to a pyrazole carboxamide derivative (hereinafter referred to as the compound of the present invention) and a fungicide containing the same as an active ingredient.

As a result of intensive studies on the pyrazole carboxamide compound, the present inventors have found that the compound of the present invention represented by the general formula [I] is preventive against many plant pathogenic bacteria,
The present invention has been completed by finding that it has a therapeutic or osmotic transition control ability.

As a plant disease for which the compound of the present invention has excellent efficacy,
For example, rice blight (Rhizoctonia solani), pseudo-blight blight
(Rhizoctonia oryzae, R. solani type IIIB), rust of wheat (Puccinia striiformis, P. graminis, P. recondita, Ph
ordei), snow rot (Typhula incarrata, T. ishikariensi
s), naked smut (Ustilago tritici, V.nuda), wilt of various crops (Rhizoctonia solani), white silkworm (Corticium rolfsi)
i), potato, beet Rhizoctonia
solani), pear scab (Gymnosporangium haraeanu)
m), apple scab (Venturia inaequaris), grass rot, leaf rot (Rhizoctonia solani), white silkworm (Corticium)
rolfsii), leaf rust (Uromyces trifolii), snow rot (Typhu
la incarnata, T. ishikariensis) and the like.

The compound of the present invention has, for example, a general formula: [In the formula, R ¹ and R ² have the same meanings as described above. ]
Can be produced by reacting the pyrazole carboxylic acid chloride represented by and 1,1-dimethyl-4-aminoindan.

Examples of the compound of the present invention are shown below, but of course the present compound is not limited to these examples.

1-methyl-3-trifluoromethyl-N- (1,1-
Dimethylindan-4-yl) pyrazole-4-carboxamide 1-methyl-3-trifluoromethyl-N- (1,1-
Dimethylindan-4-yl) pyrazole-4-carboxamide 3-fluoro-1-methyl-5-trifluoromethyl-
N- (1,1-dimethylindan-4-yl) pyrazole-4-carboxamide 5-fluoro-1-methyl-3-trifluoromethyl-
N- (1,1-dimethylindan-4-yl) pyrazole-4-carboxamide 3-chloro-1-methyl-5-trifluoromethyl-N
-(1,1-Dimethylindan-4-yl) pyrazole-4-carboxamide 5-chloro-1-methyl-3-trifluoromethyl-N
-(1,1-Dimethylindan-4-yl) pyrazole-4-carboxamide 5-bromo-1-methyl-3-trifluoromethyl-N
-(1,1-Dimethylindan-4-yl) pyrazole-4-carboxamide 5-iodo-1-methyl-3-trifluoromethyl-N
-(1,1-Dimethylindan-4-yl) pyrazole-4-carboxamide 1,3-dimethyl-5-trifluoromethyl-N-
(1,1-Dimethylindan-4-yl) pyrazole-
4-carboxamide 1,5-dimethyl-3-trifluoromethyl-N-
(1,1-Dimethylindan-4-yl) pyrazole-
4-carboxamide 3,5-bis (trifluoromethyl) -1-methyl-N
-(1,1-Dimethylindan-4-yl) pyrazole-4-carboxamide Next, a production example of the compound of the present invention will be shown as a reference example.

Reference Example 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid chloride 2 was stirred in a solution of 1.61 g of 1,1-dimethyl-4-aminoindan and 2 ml of pyridine in 50 ml of toluene at room temperature with stirring. A solution of 0.47 g of 10 ml of toluene was added dropwise, and the mixture was then stirred at room temperature for 12 hours. Next, the reaction solution was poured into cold water, and after liquid separation, the aqueous layer was extracted with ethyl acetate, the organic layer was dried over anhydrous magnesium sulfate, and the solvent was distilled off.

The residue was recrystallized from toluene to give 5-chloro-1-methyl-3-trifluoromethyl-N-
3.01 g of (1,1-dimethylindan-4-yl) pyrazolecarboxamide was obtained.

mp. 119.9 ° C. Table 1 shows some typical compounds of the present invention which can be produced by such a production method.

When the compound of the present invention is used as an active ingredient of a bactericide,
Although it may be used as it is without adding any other ingredients, normally,
It is used by mixing with a solid carrier, a liquid carrier, a surfactant, and other auxiliaries for formulation, and formulating into an emulsion, a wettable powder, a suspension, granules, powders, liquids and the like.

These formulations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 99.9%, preferably 0.2 to 80%.

As the solid carrier, kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, corncob powder, walnut shell powder, urea, ammonium sulfate, fine powder of synthetic hydrous silicon oxide or the like. Granules can be mentioned, and as the liquid carrier, xylene, aromatic hydrocarbons such as methylnaphthalene,
Examples thereof include alcohols such as isopropanol, ethylene glycol and cellosolve, ketones such as acetone, cyclohexanone and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile and water.

As the surfactant used for emulsification, dispersion, wet extension, etc., alkyl sulfate ester salt, alkyl (aryl)
Anionic surfactants such as sulfonates, dialkylsulfosuccinates, polyoxyethylene alkylaryl ether phosphates, naphthalene sulfonic acid formalin condensates, polyoxyethylene alkyl ethers,
Examples thereof include nonionic surfactants such as polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. As a formulation auxiliary agent, lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PA
P (acidic isopropyl phosphate) and the like can be mentioned.

Formulation examples are shown below. The compounds of the present invention are shown by the compound numbers in Table 1. Parts are parts by weight.

Formulation Example 1 50 parts of the compound of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain a hydrate.

Formulation Example 2 An emulsion is obtained by thoroughly mixing 10 parts of the present compound 1, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate and 70 parts of xylene.

Formulation Example 3 Compounds of the present invention 1, 2 parts, synthetic hydrous silicon oxide 1 part, calcium lignin sulfonate 2 parts, bentonite 30 parts and kaolin clay 65 parts are well pulverized and mixed, and water is added and kneaded well, then Granules are dried to obtain granules.

Formulation Example 4 25 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed and wet-ground until the particle size becomes 5 microns or less to obtain a suspension agent.

Formulation Example 5 The present compound 3, 2 parts, kaolin clay 88 parts and talc 10 parts are well pulverized and mixed to obtain a powder.

Formulation Example 6 The present compound 5, 10 parts, polyoxyethylene styryl phenyl ether 1 part, and water 89 parts are mixed to obtain a liquid preparation.

These formulations can be used as is or diluted with water to
The foliage is sprayed, and the powder is sprinkled and dispersed in the soil to be mixed or applied to the soil. In addition, it is expected to enhance the bactericidal effect by mixing with other bactericides. In addition, insecticides,
Acaricide, nematicide, herbicide, plant growth regulator, fertilizer,
It can also be used as a mixture with a soil conditioner.

Incidentally, the compound of the present invention, paddy field, upland, orchard, meadow,
It can be used as an active ingredient of a bactericide such as lawn.

When the compound of the present invention is used as an active ingredient of a fungicide, its application amount is usually 1 although it varies depending on weather conditions, formulation form, application time, method, place, target disease, target crop and the like.
1g to 100g per are, preferably 5g to 50g
When an emulsion, a wettable powder, a suspending agent, a liquid agent or the like is diluted with water and applied, the application concentration is 0.001% to 1%,
The content is preferably 0.005% to 0.5%, and granules, powders, etc. are applied as they are without any dilution.

Next, it is shown in Test Examples that the compound of the present invention is useful as an active ingredient of a bactericide. The compounds of the present invention are shown by the compound numbers in Table 1, and the compounds used for comparison and control are shown by the compound symbols in Table 2.

The control efficacy is "5", 10% if the disease state of the test plant at the time of the survey, that is, the flora of leaves, stems, etc. If it is admitted, it is "4", if about 30% is admitted, it is "3", if it is admitted about 50%, it is "2", if it is admitted about 70%, it is "1". If it is not recognized, it is evaluated as “0” on a scale of 0 to 5, 0,
Shown as 1, 2, 3, 4, and 5.

Test Example 1 Rice blight prevention effect test A plastic pot was filled with sandy loam soil, and rice (Kinki 33
No.) was sowed and grown in a greenhouse for 60 days. To a rice seedling having 6 to 7 leaves developed, a test compound which was made into an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration, and the foliage was sprayed so that it was sufficiently attached to the leaf surface. 4 hours after spraying, agar-containing agar pieces of rice wilt disease bacteria were applied and inoculated. 28 ℃ after inoculation,
It was grown under high humidity for 4 days, and the control efficacy was investigated. The results are shown in Table 3.

Test Example 2 Test for controlling rice blight disease by application to water surface 1/10000 Wagner pot was filled with sandy loam soil, rice (Kinki No. 33) was sown, and grown in a greenhouse for 80 days.
A rice seedling having 9 to 10 leaves developed was diluted with water to give a test compound as a wettable powder according to Formulation Example 1, and a predetermined amount thereof was irrigated into the soil. After irrigation, the plants were grown in a greenhouse for 7 days, and agar pieces containing rice wilt disease bacteria were applied and inoculated. After inoculation, the plant was grown at 28 ° C. under high humidity for 4 days, and the control efficacy was investigated. The results are shown in Table 4. Test Example 3 Wheat leaf rust therapeutic effect test A plastic pot was filled with sandy loam, and wheat (Agriculture 73
No.) was sowed and grown in a greenhouse for 10 days. Wheat seedlings developed on the second to third leaves were inoculated with spores of wheat leaf rust fungus. After inoculation, the mixture was grown at 23 ° C. under high humidity for 1 day, and the test compound which was made into an emulsion according to Formulation Example 2 was diluted with water to a predetermined concentration and sprayed on foliage so that it adhered sufficiently to the leaf surface.
After spraying, the seedlings were grown for 7 days under illumination at 23 ° C., and the control efficacy was investigated. The results are shown in Table 5.

Test Example 4 Ring Scab Disease Prevention Effect Test A plastic pot was filled with sandy loam soil, seeded with apples, and grown in a greenhouse for 30 days. A test compound prepared as a wettable powder in accordance with Formulation Example 1 was diluted with water to a predetermined concentration on apple seedlings having the fifth true leaf developed, and the foliage was sprayed so that the test compound was sufficiently adhered to the leaf surface. . Four hours after spraying, a spore suspension of ring scab was inoculated by spraying. After inoculation, the plants were grown at 15 ° C. under high humidity for 14 days, and the control efficacy was investigated. The results are shown in Table 6.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kenzo Matsuo 4-2-1 Takashi Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Kiyoto Maeda 4-2-1 Takashi Takarazuka-shi, Hyogo No. Sumitomo Kagaku Kogyo Co., Ltd. (72) Inventor Satoru Inoue 4-2-1 Takashi Takarazuka, Hyogo Prefecture Sumitomo Kagaku Kogyo Co., Ltd.

Claims (2)

[Claims] 1. A general formula [In the formula, R ¹ and R ² each represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and at least one of R ^{1 and} R ² represents a trifluoromethyl group. ] The pyrazole carboxamide derivative shown by these. 2. General formula [In the formula, R ¹ and R ² each represent a hydrogen atom, a halogen atom, a methyl group or a trifluoromethyl group, and at least one of R ^{1 and} R ² represents a trifluoromethyl group. ] The fungicide characterized by using the pyrazole carboxamide derivative shown by these as an active ingredient.