JPS581081B2 - Nouengeiyousatsukinzai - Google Patents

Description

Detailed Description of the Invention The present invention is based on the general formula (I) (wherein R1 and R2 represent a lower alkyl group, and
represents a lower alkyl group or a halogen atom, and n is 0.1
or 2) as an active ingredient.

In recent years, with the advancement of agricultural technology, many pest control agents have been used for the purpose of labor saving, but in order to improve productivity, it is necessary to use agents that simultaneously control various diseases, or to use the same agent to control rice and horticultural crops. There is a strong desire for the emergence of drugs that can be applied to a wide range of crop diseases.

The present inventors conducted extensive research to develop agriculturally or horticulturally useful fungicides, and found that a series of compounds represented by the general formula (I) have extremely high fungicidal activity, especially against rice. It shows remarkable control activity against rice blast, sesame leaf blight, cucumber powdery mildew, etc., and is useful as an agricultural fungicide and a horticultural fungicide, and does not cause any phytotoxicity to useful plants. It was discovered that it is an excellent drug.

The compound group represented by the general formula (I) is a new compound not described in Document 3, and can be easily produced by the method shown in the following reaction formula.

(However, in the formula, R1, R2, X and n have the same meanings as above.) Next, specific production examples will be shown.

Production Example Dehydroacetic acid 16.1' and aniline 9.31 were dissolved in 90 ml of ethanol, refluxed on a hot water bath for 4 hours, cooled to room temperature, collected a lot of precipitated crystals, and recrystallized from ethanol. Colorless columnar crystals of phenyliminoacetopyrone (compound No. 1) with a melting point of 119-121°C
I got 191.

Examples of representative compounds represented by the general formula (I) produced in this manner are as follows; however, the active ingredient compounds according to the present invention are not limited to only the exemplified compounds below. do not have.

In addition, the compound number is also referred to in the test examples shown below.

The agricultural and horticultural fungicides of the present invention include powders, aqueous phase agents, emulsions, granules,
It can be used as microgranules and other commonly practiced forms of medicament.

The carrier used in the present invention may be either solid or liquid,
Moreover, it is not limited to a specific carrier.

Examples of solid carriers include various clays, kaolin, clay, diatomaceous earth, talc, silica, etc., and liquid carriers include those that serve as solvents and non-solvents for the active ingredient compound according to the present invention. It can also be used as long as the active ingredient compound can be dispersed or dissolved by the adjuvant.

Examples include benzene, quinolene, toluene, kerosene, alcohols, ketones, dimethyl sulfoxide, dimethylformamide, and the like.

Surfactants and other adjuvants suitable for this purpose, such as spreading agents,
It can be mixed with a fixing agent and used as an aqueous solution or emulsion.

Furthermore, the active ingredient compound according to the present invention can be used in combination with other fungicides, insecticides, herbicides, plant growth regulators, etc. in order to ensure labor-saving and pest control effects.

Next, some examples of the present invention will be shown, but the main compounds and additives are not limited to the following examples.

Example 1 (Powder) 2 parts of the compound No. 1 and 98 parts of clay are uniformly mixed and ground to obtain a powder containing 2% of the active ingredient.

Example 2 (Aqueous phase agent) 70 parts of the compound No. 5, 3 parts of calcium alkylbenzenesulfonate, 5 parts of polyoxyethylene nonyl phenyl ether, and 24 parts of clay were uniformly mixed and ground to form a fine powder with a uniform composition. A hydrating powder containing 70% of the active ingredient is obtained.

When using this product, dilute it 600 to 1000 times with water and spray it on plants.

Example 3 (Emulsion) 60 parts of the compound No. 6, 23 parts of methyl ethyl ketone, and 17 parts of polyoxyethylene nonyl phenyl ether are mixed and dissolved to obtain an emulsion containing 60% of the active ingredient.

When using this product, dilute it 600 to 1000 times with water and spray it on plants.

Example 4 (Granules) 15 parts of water was added to 5 parts of the compound No. 7 above, 1.5 parts of lauryl sulfate, 1.5 parts of calcium lignin sulfonate, 25 parts of ben-1-night, and 67 parts of clay. After kneading with a kneader, it is granulated and dried with a fluidized fluid dryer.
% granules are obtained.

Next, the pest control effect of the agricultural and horticultural fungicide according to the present invention will be specifically explained using test examples.

Test Example 1 Paddy rice blast disease control test Paddy rice grown in soil in a clay pot with a diameter of 9 crrL in a greenhouse (
A powder (equivalent to 3 kg per 10 ares) prepared according to Example 1 was uniformly sprinkled on third leaf stage seedlings of the cultivar Sasanishiki using a bell jar duster.

After spraying, leave overnight under humid room conditions (humidity 95-100%, temperature 24%).
One day after the spraying, a spore suspension of the potato blast fungus was inoculated by spraying.

Five days after inoculation, the number of lesions per leaf on the third leaf was investigated, and the control value was calculated using the following formula.

Next, the test results are shown in Table 1.

As a control agent, a commercially available fungicide containing O-O-diisopropyl-S-penzyl phosphorothiolate as an active ingredient was used.

Test Example 2 Paddy rice sesame flake disease control effect test A hydrating powder prepared according to Example 2 was applied to fourth true leaf stage seedlings of paddy rice (variety: Asahi) grown in clay pots with a diameter of 9 cm in a greenhouse. A chemical solution diluted with water to a predetermined concentration was sprayed, and one day after the spraying, a conidial suspension of the rice blight fungus was inoculated by spraying.

Five days after inoculation, the number of lesions per fourth leaf was investigated, and the control value was calculated using the following formula.

Next, the test results are shown in Table 2.

Note that 2,4-dichloro-6-(0-chloroanilino)-1,3,5-triazine was used as a control drug.

Test Example 3 Cucumber Powdery Mildew Control Efficacy Test 10 ml of a test chemical solution of a prescribed concentration was sprayed on the first leaf stage seedlings of cucumber (cultivar: Kitamsan) grown in soil pots, left overnight, and then powdery mildew spore suspension was applied. Inoculation was carried out by spraying using a spray gun at a pressure of 1 kg/cm2.

Ten days after inoculation, the lesion area ratio (C%) on the leaves sprayed with the chemical was investigated, and the control value (%) was calculated in comparison with the non-sprayed area.

This test was conducted in three consecutive sessions in one section. The test results are shown in Table 3.

Note that SS-6-methylquinoxaline-2,3-diyludithiocarbonate was used as a control drug.

Claims (1)

[Claims] 1 General formula (wherein R1 and R2 represent a lower alkyl group,
represents a lower alkyl group or a halogen atom, n is 0,
1 or 2)
An agricultural and horticultural fungicide characterized by containing seeds or more as an active ingredient.