JPS606321B2 - Fungicide for agriculture and horticulture - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a fungicide for screen gardening that contains a compound represented by the formula as an active ingredient.

The compound represented by the above formula exhibits strong antibacterial activity comparable to that of penzimidazole-2-carbamic acid ster, which has been reported in many cases, and is effective against sesame flaking disease, blast disease, sheath blight disease, and wisteria disease of rice. It is capable of accurately controlling Botrytis blight on rapeseed, fruit trees, Hanai, etc., and powdery mildew on Grandson's cabbages, fruit trees, Hanai, etc.

In recent years, with the advancement of agricultural technology, many agricultural and horticultural fungicides have been used for the purpose of saving labor.

However, in order to improve productivity, there are few drugs that can simultaneously control various diseases in the same crop, or drugs that can accurately control a wide range of crop diseases with the same drug, so the emergence of useful drugs is slow. Highly desired. In view of these points, the present inventors synthesized various compounds and studied their biological activities in order to develop new and useful agricultural and horticultural fungicides.

As a result, it has been found that the compound represented by the above formula is stable against ultraviolet rays and rain, and has extremely excellent pesticidal activity as an agricultural and horticultural fungicide with a long shelf life. The active ingredient compound of the present invention can be easily produced by the method shown by the following reaction formula.

The above reaction uses acetone, In an inert solvent such as tetrahydrofuran, dioxane, acetonitrile, or dimethylformamide, alkaline salts such as sodium carbonate, potassium carbonate, or sodium bicarbonate, or tertiary amines such as triethylamine, or aromatic tertiary amines such as pyridine are added as deoxidizing agents. The reaction temperature can be carried out in the presence of a class amine.The reaction temperature is in the range of 0°C to 7 pm, preferably 5 to 30 qO.The method for synthesizing the compound of the present invention is shown as a reference example.

Reference Example 10.25 hours of penzimidazole-2-carbamic acid methyl ester and 12 hours of diluted potassium carbonate were suspended in 200 minutes of acetone, and 8 hours of 2-oxoimidazolidine-1-carbonyl chloride was added at room temperature for 5 hours at room temperature. Allow time to react.

After the reaction, remove the acetone by concentrating it and pour 500 ml of cold water on the Isosasa.
When the crystals are heated and dried, 1-(2
-oxoimidazolidine-1-benzimidazole-2-benzimidazole-carbamic acid methyl ester is obtained. This was recrystallized from a mixed solvent of dimethylformamide and water to obtain 11.6 ta. Melting point 147-14 is ○ Elemental analysis value: C, 3 days, 3N504・1' Rainbow LO as C day N calculated value (%) 50.73 4.42
22.75 Actual value (many) 50.78 4.55
22.57 The compound that is the active ingredient of the present invention can be used as an agricultural and horticultural fungicide as it is, but it may be mixed with various bases depending on the usage situation. , powders, granules, wettable powders, tablets, oils, emulsions,
It can also be used in dosage forms such as aerosols and laxatives.

The base mentioned herein may be solid, liquid, or gas, or a combination thereof.

These examples are talc, clay, kaolin, -
Keibushi, calcium carbonate, potassium chlorate, saltpeter, wood flour, nitrocellulose, starch, gum arabic, water, alcohol, kerosene, naphtha, xylol, methylnaphthalene, benzene, acetone, air, nitrogen, carbon dioxide, freon, Vinyl chloride, propane, butane, etc. are used as adjuvants used in the formulation of agricultural and horticultural chemicals, such as spreading agents, emulsifiers, dispersants, wetting agents, etc. Nonionic (polyoxyethylene derivatives, ethylene oxide) propylene oxide copolymers, sorbitan esters, etc.), anionic (soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), cationic ( (aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, etc.) and amphoteric surfactants (alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, etc.). However, it goes without saying that the embodiments of the present invention are not necessarily limited to the above-mentioned dosage form.

In addition, in the present invention, various insecticides, fungicides, herbicides,
A wider range of effects can be expected by using it in combination with plant growth regulators, acaricides, bran insecticides, attractants, repellents, plant nutrients, fertilizers, etc.

The agricultural and horticultural fungicide of the present invention is generally desirably adjusted to a concentration of 100 to 50Q blood, although it depends on the type of pathogenic microorganism.

Not only can this be applied directly to areas where harmful microorganisms are occurring to achieve an effect, but it can also be applied to areas where harmful microorganisms are expected to occur. As a treatment method, a spraying method, a soil application method, etc. are used. Experimental examples of the agricultural and horticultural fungicide of the present invention are shown below.

Experimental Example 1 Test of effect on control of rice mongare disease Six seedlings of paddy rice (Nipponbare) grown in clay pots in a greenhouse were used as test samples.

An emulsion prepared according to Example 3 described later was diluted with water to a predetermined concentration and sprayed all over the stems and leaves of rice seedlings. The amount of spraying agent was set at a ratio of 30° to 5 rice seedlings per 9° clay pot. After the chemical solution dries, leave it in the greenhouse for 2 hours, and then inoculate it with o-related humidity of 95% or more. After keeping it in the box for 4 hours, it was taken out and kept in a greenhouse in a plastic pet (24-3 ○). After one week, the average number of infected stems was calculated.
The average diseased stalk rate for each drug was calculated using the following formula and compared. Average diseased stem rate (%) = Kouyo Urawarabishi X. .

. The results are shown in Table 1.

Table 1 *1) Average disease - Zhang Yushen length... Average length of the top developed lesions *2) Benomyl: 1-(butylcarbamoyl)
-2-penzimigsol methyl carbamate *3)
Palidamycin A Experimental Example 2 Cucumber gray mold control effect test Cucumber (Tokiwa) grown in a clay pot in a greenhouse has 5 true leaves.
Young seedlings were used when they had grown to ~6 pieces.

A hydrating agent prepared according to Example 2 described later was diluted with water to a predetermined concentration and sprayed over the entire surface of the foliage. The amount of spray liquid is 30' for 5 cucumber seedlings per 9' clay pot.
The percentage of After the chemical solution dried, the chestnuts were returned to the greenhouse for 2 feeding hours, and then the botrytis cineraria cultured in the potato pottery was punched out using a cork pole with a diameter of 5 legs, and the disk was inoculated in the center of the chestnut surface. . After vaccination 2
The animals were kept in an inoculation room with a relative humidity of 95% or higher for two hours, and then infected with a humid vinyl pet at a temperature of 18 to 2 crabs. On the 6th day after inoculation, the average rate of diseased hollyhock was calculated using the following formula, and the effects of each drug were compared. Average rate of diseased hollyhocks (%); Number of leaves examined in the clump x 100 The results are shown in Table 2.

Table 2 *1) Thiophanate methyl: 4.4-0-phenylenebis(3-thioallophane) dimethyl, *2) Benomyl: 1-(butylcarbamoyl)-2-penzimitazole-methylcarbamate Experimental example 3 Test for controlling powdery mildew in cucumbers Young seedlings of cucumber (Tokiwa) grown in clay pots in a greenhouse with their first true leaves developed were examined.

Wettable powders for each drug prepared according to Example 2 below were diluted with water to a predetermined concentration and sprayed on cucumber leaves. The amount of sprayed liquid was set at a ratio of 30 to 5 cucumber seedlings per 9-skin clay pot. After the chemical solution had dried, it was left in a greenhouse for two hours, and conidia of the powdery mildew fungus (Sphaerotica friginea), which had been subcultured on cucumbers, were uniformly inoculated and infected. Thereafter, the plants were kept in a glass greenhouse (20cm), and on the 10th day after inoculation, the average rate of diseased hollyhock was determined and the effects of each drug were compared. The results of the total number of affected hearts are shown in Table 3.

Table 3 *1) DPC: Dinitromethylhebutyl phenyl cronate *2) Benomyl: 1-(butylcarbamoyl)
-2-Penzimiguzole Methyl carpamate Next, examples of the present invention will be illustrated, but these are not necessarily intended to limit the formulation, compounds, usage standards, etc. of the present invention.

Example 1 5 parts of the compound of the present invention (parts by weight are shown).

The same applies to the following examples), 1 part of white carbon, 60 parts of clay, and 34 parts of turk are mixed and ground to use as a powder. Example 2 3 parts of the compound of the present invention, 1 part of white carbon, 2 parts of sodium lignin sulfonate, 2 parts of polyoxyethylene nonyl ether, and 56 parts of clay are mixed and pulverized to be used as a wettable powder.

Example 3 Two parts of the compound of the present invention, one part of a mixture of polyoxyalkyl allyl ether and alkylaryl sulfonate, two parts of xylene, and five parts of cyclohexanone are mixed and dissolved and used as an emulsion.

Claims (1)

[Scope of Claims] 1. An agricultural and horticultural fungicide characterized by containing as an active ingredient a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼.