JPH0350721B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [] (In the formula, X represents a halogen atom or a lower alkyl group, Y represents a halogen atom, Q represents a hydrogen atom or a hydroxyl group, m and n represent integers of 0 to 2, and when m and n are 2, , X, and Y may be the same or different. 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 made earnest efforts to develop a drug that exhibits strong effects even in small amounts, and have completed the present invention. The compound of the present invention represented by the general formula [] shows excellent effects against diseases of useful cultivated crops, is highly safe for humans, livestock, and fish, and shows no adverse effects on crops. It's something that doesn't exist. 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. In particular, it shows excellent efficacy against powdery mildew, rust, etc. of useful plants. The method for producing the compound of the present invention represented by the general formula [] is described, for example, in JP-A-57-188571, and it is also described that it has a plant growth regulating effect. 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. The position numbers of substituents X and Y in Table 1 are as follows.

【table】

[Table] Since the compound of the present invention thus obtained has systemic transferability to plants, any treatment method is possible, such as above-ground foliage treatment, seed treatment, water surface treatment, or soil treatment. . 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 processed product 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, it can be used in various solid and liquid forms that are commonly used in the formulation of agricultural chemicals. By mixing with a carrier, it can be manufactured into 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 antifreezing agents can be added to the drug. The carrier referred to herein may be either solid or liquid, or a combination thereof. Examples of these include 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 an appropriate 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. Furthermore, by mixing with other fungicides, herbicides, plant growth regulators, insecticides, acaricides, and other pesticides, 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
0.5-1000ppm, preferably 3-500ppm,
The dosage (as the compound of the present invention) is generally 0.5 to 500 g per 10 ares, preferably 1 g per 10 ares.
~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 Cucumber powdery mildew control test (preventive effect) diameter 15
A cm clay pot was filled with granular soil for gardening, and 10 seeds of cucumber (variety: Takasago) were sown. Do this in a greenhouse
After cultivating for 10 days, the cotyledons expanded and young seedlings were used for testing. 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, the disease state was investigated. The disease severity was calculated by the following method. That is, depending on the lesion area of the investigated leaves, the disease severity index was classified into 0, 1, 2, 3, 4, and 5 as shown below.

[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 )
/(Incidence level in untreated area) x 100 The results are shown in Table 2.

【table】

[Table] Methyl midate test example 2 Cucumber powdery mildew control test (therapeutic effect) diameter 15
A cm clay pot was filled with horticultural soil, and 10 seeds of cucumber (variety: Takasago) were sown, cultivated in a greenhouse for 10 days, and young seedlings with fully expanded cotyledons were used as samples. The seedlings were inoculated with a conidial aqueous solution of Sphaerotheca fuliginea by spraying, and after being left in a greenhouse at 23 to 26°C for 1 day, an emulsion of the compound of the present invention obtained in Formulation Example 3 was added to water. The solution was diluted to a specific concentration and sprayed at 15 ml per pot.
After air-drying and cultivating for 10 days at a temperature of 23 to 26°C, 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 Wheat powdery mildew control test (preventive effect) Arakida soil was filled in a clay pot with a diameter of 12 mm, and wheat (variety: Norin 61)
No.) 15 seeds were sown. This was cultivated in a greenhouse for 12 days, and the young seedlings whose first leaves had developed were used for testing. 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 in accordance with Test 1. The results are shown in Table 4.

【table】

[Table] Dimethyl 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 cultivate it in a greenhouse for 12 days. Young seedlings with one leaf developed were tested. This young seedling is infected with wheat powdery mildew fungus (Erysiphe).
graminis), and after inoculation, leave to stand for 1 day under greenhouse conditions at 20 to 23°C, and then 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. Production Example 1 Powder Compound No. 17 2 parts Clay 98 parts The above ingredients are mixed and pulverized to obtain a powder. Formulation Example 2 Wettable powder Compound No. 7 10 parts Sodium alkylsulfonate 5 parts Clay 85 parts The above ingredients are mixed and pulverized to obtain a wettable powder. Formulation Example 2 Emulsion Compound No. 22 5 parts Calcium alkylbenzenesulfonate 4 parts Polyoxyethylene alkyl phenyl ether
11 parts cyclohexanone 10 parts xylene 70 parts Mix the above to obtain an emulsion. Formulation Example 4 Emulsion Compound No. 27 10 parts Calcium alkylbenzenesulfonate 3 parts Polyoxyethylene alkyl phenyl ether
12 parts dimethylformamide 10 parts xylene 65 parts or more are mixed to obtain an emulsion. Formulation Example 5 Granules Compound No. 25 2 parts Calcium lignin sulfonate 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 Compound No. 33 10 parts ethylene glycol 5 parts xanthan gum 0.2 parts polyoxyethylene sorbitan monooleate
5 parts water 79.8 parts Wet grind the above 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, Q represents a hydrogen atom or a hydroxyl group, m and n represent integers of 0 to 2, and when m and n are 2, , X and Y may be the same or different.