JPS6054927B2 - Fungicide for agriculture and horticulture - Google Patents

Description

[Detailed explanation of the invention] The present invention is related to a farm -shared sterilizer that is an active ingredient that is represented by NNH [C: C ■ ℃ 2H5 and ON "NNH.

The compound represented by the above formula exhibits strong antibacterial activity that is comparable to that of benzimidazole-2-carbamate esters that have been reported in many cases, and is effective against sesame flaking, blast, sheath blight, and rice blight. It can accurately control gray mold on vegetables, fruit trees, flower bowls, etc., and powdery mildew on stored vegetables, fruit trees, flower petals, etc.

In recent years, with the advancement of agricultural technology, many common fungicides have been used in farms 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 that can optimally control a wide range of crop diseases with the same drug, so there is a strong desire for the emergence of useful drugs. It is rare. In view of these points, the present inventors synthesized various compounds and studied their biological activities in order to develop a new and useful fungicide for common use in farms.

As a result, it was found that the compound represented by the above formula has extremely excellent pesticidal activity as a fungicide for common use in farms.
The active ingredient compound of the present invention can be easily produced by the method shown by the following reaction formula.

The above reaction can be carried out in an inert solvent such as chloroform, tetrahydrofuran, dioxane, acetonitrile, or dimethylformamide in the presence of a tertiary amine such as triethylamine or an aromatic tertiary amine such as pyridine as a deoxidizing agent. At this time, the reaction temperature is in the range of 0°C to 50°C, preferably 5 to 10°C. A method for synthesizing the compound of the present invention will be shown as a reference example.

Reference Example 20.5y of benzimidazole-2-carbamic acid ethyl ester and 14ml of triethylamine were suspended in 500ml of chloroform, and 14.8V of 2-oxoimidazolidine-1-carbonyl chloride was added under ice-cooling for 1 hour. Then, the mixture is stirred and reacted at room temperature for 2 hours.

Unreacted raw materials are filtered off and chloroform is distilled off, leaving a solid residue. Next, add 200ml of water to remove the crystals.
take. The obtained crystals are recrystallized from a mixed solvent of dimethylformamide and water to obtain 20y of 1-(2-oxoimidazolidine-1-carbonyl)-2-penzimidazole-carbamic acid ethyl ester. Melting point 184~
185ruC Elemental analysis value: Cl4Hl5N5O4・114H20 The compound which is the active ingredient of the present invention can be used as it is as an agricultural and horticultural fungicide, but depending on the usage situation. It can also be mixed with various bases and used in the form of powders, granules, wettable powders, tablets, oils, emulsions, aerosols, smokes, etc.

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

These examples include talc, clay, kaolin, diatomaceous earth, calcium carbonate, potassium chlorate, saltpeter, wood powder,
Nitrocellulose, starch, gum arabic, water, alcohol, kerosene, naphtha, xylol, methylnaphthalene, benzene, acetate, air, nitrogen, carbon dioxide, freon, vinyl chloride, propane, butane, etc., as well as agricultural and horticultural uses. Nonionic (polyoxyethylene derivatives, ethylene oxide propylene oxide copolymers, sorbitan esters, etc.) and anionic (polyoxyethylene derivatives, ethylene oxide propylene oxide copolymers, sorbitan esters, etc.) as adjuvants used in drug formulations, such as spreading agents, emulsifiers, dispersants, wetting agents, etc. Soaps, sulfated oils, alkyl sulfate ester salts, petroleum sulfonates, dioctyl sulfosuccinate salts, alkylaryl sulfonates, etc.), cationic (fatty amine salts, quaternary ammonium salts, alkylpyridinium salts, etc.) ) and amphoteric systems (alkylaminoethylglycine, alkyldimethylbetaine, polyglycol sulfate, alkylamine sulfonic acid, etc.)
Examples include surfactants. 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,
By using it in combination with plant growth regulators, miticides, nematicides, attractants, repellents, plant nutrients, fertilizers, etc., a wider range of effects can be expected.

The agricultural and horticultural fungicide of the present invention is preferably used at a concentration of 100 to 500 ppm, 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 to achieve an effect. 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 Rice Mongare Disease Control Effect Test Six true-leaf seedlings of rice field (Motoharu) grown in clay pots in a greenhouse were tested.

An emulsion prepared according to Example 3 was diluted with water to a predetermined concentration and sprayed over the entire surface of rice seedlings. The amount of spraying agent was set at a rate of 30 mt for 5 rice seedlings per 9 cm clay pot. Chemical liquid! It's been 24 years since it dried! ] Leave it in the Terama greenhouse, then inoculate the rice mongare disease bacterium (Pericillaria sasaki) obtained by culturing it on rice straw, and place it in an inoculation box at 26°C and relative humidity of 95% or more. After keeping for a long time, take out the plastic pet in the greenhouse (24~3S7C)
I kept it. One week later, the average number of diseased stems was determined, and the average diseased stem rate for each drug was calculated using the following formula and compared. The results are shown in Table 1.

Experimental Example 2 Test for the control effect of botrytis gray mold disease on cucumber (Tokiwa) grown in clay pots in a greenhouse with 5 true leaves.
Young seedlings were used when they had grown to ~6 pieces.

Using a hydrating agent prepared according to Example 2, it was diluted with water to a predetermined concentration and sprayed over the entire surface of the stems and leaves. The amount of spray liquid is 9
The ratio was 30 mt for 5 lily cucumber seedlings per cm clay pot. After the chemical solution dried, it was left in a two-hashi greenhouse, and then the gray mold fungus (Botrytis cineraria) cultured in potato medium was punched out using a cork borer with a diameter of 5 T$t, and the disk was inoculated into the center of the leaf surface. 27 days after vaccination
/C relative humidity of 95% or more in an inoculation room for 2 hours, and then infected with a humid vinyl pet at a temperature (18-28°C). On the 6th day after inoculation, the average rate of diseased leaves was calculated using the following formula, and the effects of each drug were compared. The results are shown in Table 2.

Experimental Example 3 Measures to control powdery mildew of cucumber. Young seedlings of cucumber (Tokiwa) grown in clay pots in a greenhouse with their first true leaves spread were used as an experiment.

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 30 ml per 5 cucumber seedlings per 9 cm clay pot. After the chemical solution had dried, it was left in a greenhouse for two hours, and conidia of powdery mildew fungus (Sphaeroteica friginea), which had been subcultured on cucumber leaves, were uniformly sprayed and inoculated to cause infection. After that, inside the glass constant temperature room (23
℃), and the average rate of diseased leaves was determined 10 days after inoculation and seeding, and the effects of each chemical were compared. Next, examples of the present invention will be illustrated, but these do not necessarily 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 talc are mixed and crushed to be used as a powder. Example 2 Parts of the compound of the present invention (9), w parts of white carbon, 2 parts of sodium lignin sulfonate, 2 parts of polyoxyethylene nonyl ether, and 56 parts of clay were mixed and pulverized to be used as a wettable powder.

Example 3 Part of the compound of the present invention, part of polyoxyalkyl allyl ether and alkylaryl sulfonate mixture, part of xylol 2? , cyclohexanone (a) 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.▼.