JPH0368860B2 - - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to the general formula (In the formula, X represents a halogen atom or a lower alkyl group, Y represents a halogen atom, a lower alkyl group, or a lower alkyloxy group, m represents an integer of 0 to 2, and n represents an integer of 1 or 2. When m or n is 2, X and Y may be the same or different. This invention relates to agricultural and horticultural fungicides. Many synthetic organic compounds and antibiotics with bactericidal properties have already been discovered, and many substances have been developed as fungicides for agriculture and horticulture. However, in recent years, the emergence of resistant bacteria and environmental pollution due to mass spraying have become problems. In addition, in recent years, many inventions related to so-called azole compounds as agricultural and horticultural fungicides have been announced.
For example, JP-A-56-152446, JP-A-57-16870, JP-A-57-48982, JP-A-57-120579, JP-A-57-
There are 126479. However, these compounds often have plant growth inhibitory and herbicidal effects, and have the drawback that they cannot necessarily be said to be safe to use. In order to compensate for these drawbacks, the present inventors have worked diligently to develop a drug that has a novel skeleton and is highly effective even in small amounts, and have completed the present invention. The compound of the present invention represented by the general formula does not show any adverse effects. The compound of the present invention represented by the general formula [] is widely applicable as an agricultural and horticultural fungicide for both prevention and treatment against various pathogenic bacteria belonging to the fungi, ascomycetes, basidiomycetes, and deuteromycetes. You can. It is particularly effective against powdery mildew, rust, etc. of useful plants. In addition, similar compounds to the compound of the present invention represented by the general formula [] are described in JP-A-53-72825 as having bactericidal activity for agricultural and horticultural purposes.
Both have lower activity than the compounds of the present invention. When producing the compound of the present invention represented by the general formula [], the general formula [] (However, in the formula, X, Y, m and n have the same meanings as above.) To the aminobenzophenone derivative represented by the general formula [] (However, in the formula, Hal represents a halogen atom.) It can be easily obtained by reacting isonicotinic acid halide or its hydrohalide salt represented by the following formula. The benzophenone derivative represented by the general formula [] is, for example, SYNTHESIS.
1980, p. 677. In this reaction, use an inert solvent such as benzene, toluene, chloroform, pyridine, dimethylformamide, etc., and further use pyridine, triethylamine, N,N-dialkylaniline, potassium carbonate, soda carbonate, etc. as a deoxidizing agent. This allows the reaction to proceed smoothly.
Room temperature is sufficient for the reaction temperature, but appropriate cooling or heating may be performed depending on the case. Preferably 0
℃~60℃. Next, a manufacturing example will be shown. Production example Isonicotinic acid-2-(4-chlorobenzoyl)anilide (compound number 2) 2-amino-4'-chlorobenzophenone 4.6 g
was dissolved in 100 ml of pyridine, the solution was cooled with ice while stirring, and the solution was dissolved in isonicotinic acid chloride hydrochloride.
Add 3.6g little by little. After adding 2 more
After stirring at room temperature for an hour, approximately 400 ml of water is added to the reaction solution. The precipitated crystals were separated, washed with water, dried, and recrystallized from a mixture of ethyl acetate and n-hexane to give 6.1 g of a compound with a melting point of 179-180°C (yield:
90%). Elemental analysis value C ₁₉ H ₁₃ ClN ₂ O ₂ (molecular weight 336.77) C H N Calculated value (%) 67.76 3.89 8.32 Experimental value (%) 67.68 3.94 8.24 The compounds of the present invention thus obtained are shown in Table 1 . However, the compounds in Table 1 do not limit the compounds of the present invention. The compound numbers in the table also apply to the following test examples and formulation examples. In Table 1, the positions of substituents X and Y are as shown below. [Table] [Table] The compound of the present invention, which has been limited in this manner, has systemic transferability to plants, so any treatment method such as above-ground foliage treatment, seed treatment, water surface treatment, or soil treatment can be used. It is possible. In addition, since the compounds of the present invention do not have any adverse effects on the target useful plants, the compounds of the present invention can be used at any stage of the useful plants, including before sowing, during the sowing period, during the seedling stage, during the growing season, and during the fruiting stage. It is possible to use When actually using the compound of the present invention, it is possible to use it as it is without adding other ingredients, but in order to make it more convenient to use, various solid and liquid carriers used in the preparation of general agricultural chemicals may be used. It can be mixed with powder to produce wettable powders, emulsions, oils, powders, granules, flowables, etc. Furthermore, auxiliary agents such as dispersants, diluents, emulsifiers, spreading agents, wetting agents, adsorbents, thickeners, antifoaming agents, and antifreeze agents can be added to the drug. The carrier referred to herein may be either solid or liquid, or a combination thereof. Listing these examples are talc, clay, bentonite,
Kaolin, diatomaceous earth, calcium carbonate, wood flour, starch, gum arabic, water, alcohol, kerosene,
Examples include naphtha, xylene, cyclohexanone, methylnaphthalene, benzene, acetone, dimethylformamide, glycol ether, and N-methylpyrrolidone. Examples of adjuvants include polyoxyethylene alkyl phenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxide propylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate ester salts, Petroleum sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonates, aliphatic amine salts,
Quaternary ammonium salts, alkylpyridinium salts, alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose,
Examples include ethylene glycol and xanthan gum. It can also be used as an aerosol agent by mixing with a propellant such as fluorotrichloromethane or dichlorodifluoromethane, or as a fumigant or smoke agent by mixing with a suitable blowing agent or combustion agent. In formulation, the mixing ratio is generally 0.05 to 95%, preferably 0.1% by weight of the compound of the present invention.
~80%, particularly preferably 1~70%, optimally 70~99% as a carrier and 0~20% as an adjuvant. Further, by mixing with other fungicides, herbicides, plant growth regulators, insecticides, acaricides, and other agricultural chemicals, fertilizers, etc., a wider range of effects can be expected. When actually using the compound of the present invention, it is natural that the concentration should be selected appropriately depending on the time of use, weather conditions, method of use, dosage form, place of use, target disease, target crop, etc. In general
The amount is 0.5 to 1000 ppm, preferably 3 to 500 ppm, and the amount used (as the compound of the present invention) is generally 0.5 to 500 g per 10 are, preferably 1 to 1 to 500 g per 10 are.
It is 250g. Next, the usefulness of the compound of the present invention as a fungicide for agriculture and horticulture will be explained using test examples. Test Example 1 Powdery mildew control test on cucumber (preventive effect) A clay pot with a diameter of 15 cm was filled with granular soil for horticulture, and 10 seeds of cucumber (variety: Takasago) were sown. This was cultivated in a greenhouse for 10 days, and the young seedlings with expanded cotyledons were used as samples. The hydrating powder of the compound of the present invention obtained in Formulation Example 2 was diluted with water to a predetermined concentration on these young seedlings, and 15% of the powder was added per pot.
ml was sprayed. After the chemical solution was air-dried, a conidial aqueous solution of Sphaerotheca Fuliginea was spray inoculated onto the shoots and leaves. After inoculation, 23-26
After cultivating for 10 days under greenhouse conditions at ℃, the disease state was investigated. The disease severity was calculated by the following method. That is, the lesions were classified into disease severity indexes of 0, 1, 2, 3, 4, and 5 as shown below, depending on the lesion area of the investigated leaves. [Table] Based on the disease severity index thus obtained, the disease severity was calculated using the formula below, and the control value was further calculated from the comparison with the disease severity in the untreated area using the formula below. Disease severity (%) = Σ ( disease severity index ) × ( number of leaves ) / 5 × ( number of inspected leaves ) × 100 Control value ( % ) = ( disease severity in untreated area ) – ( disease severity in treated area ) / ( non-treated area ) Disease severity in treatment area) x 100 The results are shown in Table 2. [Table] [Table] Methyl bamate test example 2 Powdery mildew control test on cucumber (therapeutic effect) A clay pot with a diameter of 15 cm was filled with horticultural soil, 10 seeds of cucumber (variety: Takasago) were sown, and 10 seeds were placed in a greenhouse. The seedlings were cultivated for one day and the seedlings with fully expanded cotyledons were used as samples. This young seedling is infected with the powdery mildew fungus (Sphaerotheca).
Spray inoculation with conidial aqueous solution of 23
After being left in a greenhouse at ~26°C for one day, the emulsion of the compound of the present invention obtained in Formulation Example 3 was diluted with water to a predetermined concentration and sprayed at 15 ml per pot. After air drying, 23-26
After cultivation for 10 days under greenhouse conditions at ℃, the disease state was investigated. The disease severity index, disease severity, and control value are as in Test Example 1.
According to. The results are shown in Table 3. [Table] [Table] Test Example 3 Powdery Mildew Control Test (Preventive Effect) A clay pot with a diameter of 12 cm was filled with Arakida soil, and 15 grains of wheat (variety: Norin No. 61) were sown. Do this in a greenhouse
Seedlings that had been cultivated for 12 days and had developed their first leaves were tested. The emulsion of the compound of the present invention obtained by the method of Formulation Example 4 was diluted with water to a predetermined concentration on the seedlings, and 15 ml was added to each pot.
was sprayed. After air drying, wheat powdery mildew (Erysiphe
graminis) was inoculated by spraying with an aqueous solution of conidia.
After inoculation, the plants were cultivated for 10 days under greenhouse conditions at 20-24°C, and then the disease state was investigated. The disease severity index, disease severity, and control value are as in Test Example 1.
According to. The results are shown in Table 4. [Table] [Table] Test example 4 Wheat powdery mildew control test (therapeutic effect) Fill a clay pot with a diameter of 12 cm with Arakida soil, sow 15 grains of wheat (variety: Norin No. 61), and grow in a greenhouse for 12 days. Young seedlings with the first leaf developed were used for testing. This young seedling is infected with wheat powdery mildew fungus (Erysiphe).
After inoculation by spraying with an aqueous solution of conidial spores of A. graminis) and leaving it for one day under greenhouse conditions at 20 to 23°C, add a wettable powder of the compound of the present invention obtained by the method of Formulation Example 2 to a predetermined concentration with water. Dilute and spray 15ml per pot.
After air-drying, the plants were cultivated in a greenhouse at 20-24°C for 10 days, and then the disease state was investigated. The disease severity index, disease severity, and control value are as in Test Example 1.
According to. The results are shown in Table 5. [Table] [Table] Examples of formulations are shown below. "Parts" in the examples are "parts by weight"
shows. Formulation Example 1 Powder Compound No. 2 2 parts Clay 98 parts The above ingredients are mixed and pulverized to obtain a powder. Formulation Example 2 Wettable powder Compound No. 4 10 parts Sodium alkylsulfonate 5 parts Clay 85 parts The above ingredients are mixed and pulverized to obtain a wettable powder. Formulation Example 3 Emulsion Compound No. 3 5 parts Calcium alkylbenzenesulfonate
4 parts polyoxyethylene alkyl phenyl ether 11 parts cyclohexanone 10 parts xylene 70 parts The above ingredients are mixed to obtain an emulsion. Formulation Example 4 Emulsion Compound No. 24 10 parts Calcium alkylbenzenesulfonate
3 parts polyoxyethylene alkyl phenyl ether 12 parts dimethylformamide 10 parts xylene 65 parts Mix the above to obtain an emulsion. Formulation Example 5 Granules Compound No. 18 2 parts Calcium ligninsulfonate 2 parts Bentonite 30 parts Talc 66 parts The above ingredients are mixed, water is added, kneaded, granulated, and dried to obtain granules. Formulation Example 6 Flowable agent Compound No. 33 10 parts Ethylene glycol 5 parts Xanthan gum 0.2 parts Polyoxyethylene sorbitan monooleate 5 parts Water 79.8 parts The above is wet-pulverized to obtain a flowable agent.

Claims (1)

[Claims] 1. General formula (In the formula, X represents a halogen atom or a lower alkyl group, Y represents a halogen atom, a lower alkyl group, or a lower alkyloxy group, m represents an integer of 0 to 2, and n represents an integer of 1 or 2. When m or n is 2, X and Y may be the same or different.) An isonicotinic acid anilide derivative represented by: 2 General formula (In the formula, X represents a halogen atom or a lower alkyl group, Y represents a halogen atom, a lower alkyl group, or a lower alkyloxy group, m represents an integer of 0 to 2, and n represents an integer of 1 or 2. When m or n is 2, X and Y may be the same or different. disinfectant.