JPS5848549B2 - Acetanilide derivatives and agricultural and horticultural fungicides containing the derivatives - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (wherein X represents a lower alkyl group, a lower alkoxy group, or a halogen atom, n represents O or an integer from 1 to 3, and n is 2 or more This invention relates to a novel acetanilide derivative, which has not been published in any literature, and which is represented by the formula "X" and "X" may be the same or different, and R represents a lower alkyl group, and an agricultural and horticultural fungicide containing the derivative as an active ingredient. .

In recent years, with the advancement of agricultural technology, many agricultural and horticultural fungicides have been used for the purpose of labor saving. Currently, there are few fungicides that can accurately control diseases of a wide range of crops.

Under these circumstances, there is a strong desire for the emergence of new and useful fungicides.
** In view of these circumstances, the present inventors synthesized a large number of compounds and repeated various tests on their usefulness in order to develop new and useful drugs.

As a result, the specific acetanilide derivative represented by the above general formula (I) has an extremely remarkable control effect as an agricultural and horticultural fungicide, especially against rice blast and sesame leaf blight, and furthermore, it has an extremely remarkable control effect on rice blast and sesame leaf blight, and also has a particularly remarkable control effect on tomato blast. It was also found that it has a control activity against late blight that is comparable to that of commercially available fungicides.

The present invention was made based on such knowledge, and provides a new and useful acetanilide derivative and an agricultural and horticultural fungicide containing the derivative as an active ingredient.

The active ingredient compound of the present invention can be easily produced by the method shown in the following reaction formula.

Production example N-benzyl-2,4-xylidine 2.11 (0.01
mol) and triethylamine (1.01 mol) were dissolved in benzene, and while cooling and stirring, 1.2y (o.oi mol) of α-methylthioacetyl chloride was added dropwise.

After the dropwise addition, the reaction solution was cooled under reflux for 1 hour, and then the reaction solution was washed with water and dried over anhydrous sodium sulfate, and then benzene was distilled off.

Distilling the obtained oil under reduced pressure; b. p. 179-184
℃/ ※※0. 2.4P (yield: 8o%) of the desired product (compound No. 2) as a pale yellow oil with 8 mmHg was obtained.

The elemental analysis value of nitrogen is 4.63 wt% (theoretical value 4.68
wt%).

Representative compounds represented by the general formula (I) thus produced are illustrated below, but the effective compounds according to the present invention are not limited to the exemplified compounds below.

The agricultural and horticultural fungicides of the present invention include powders, wettable powders, 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 the solid carrier include various clays, kaolin, clay, giesel earth, talc, and limestone, and examples of the liquid carrier include those that serve as a solvent and non-solvent for the active ingredient compound according to the present invention. However, any auxiliary agent that can disperse or dissolve the effective compound can be used.

Examples include benzene, xylene, toluene, crocin, alcohols, chthons, dimethyl sulfoxide, dimethylformamide, and the like.

A suitable surfactant and other auxiliary agents such as a spreading agent and a fixing agent can be mixed with this to form an aqueous solution or an emulsion.

In addition, the effective compound according to the present invention may be used in combination with other fungicides, insecticides, herbicides, etc. to ensure labor-saving and pesticidal effects.
It can be used in combination with plant growth regulators, etc.

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

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

Example 2 (Wettable powder) 70 parts of the compound No. 5 above, 3 parts of calcium alkylbenzene sulfonate, 5 parts of polyoxyethylene nonyl phenyl ether, and 23 parts of clay were uniformly mixed and pulverized to form a fine powder with a uniform composition. An aqueous phase agent containing an effective proportion of 70% is obtained.

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

Example 3 (Emulsion) By mixing and dissolving 60 parts of the compound No. 6, 723 parts of methyl ethyl keto, and 17 parts of polyoxyethylene nonyl phenyl ether, an emulsion containing 60% of the active ingredient is obtained.

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

Example 4 (Granules) 5 parts of the compound No. 8 above, 1 part lauryl sulfate. 5 parts, +) calcium guninsulfonate 1.5
15 parts of water were added to 25 parts of bentonite and 67 parts of clay, kneaded in a mixer, granulated, and dried in a fluidized fluid dryer to obtain 5% granules.

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 Rice blast disease control effect test A hydrating powder prepared according to Example 2 was applied to third true leaf stage seedlings of paddy rice (variety: Asahi) grown in clay pots with a diameter of 9 cr 1'L in a greenhouse. A chemical solution diluted with water to a predetermined concentration was sprayed, and one day after the spraying, a live spore suspension of rice 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.

Next, the test results are shown in Table 2.

As a comparison agent, a commercially available fungicide whose chemical name is S-penzyldiisopropylphosphorothiolate was used.

Test Example 2 Rice sesame leaf blight control effect test Paddy rice grown in soil in a clay pot with a diameter of 9crfL in a greenhouse (
A chemical solution prepared by diluting a wettable powder prepared according to Example 2 with water to a predetermined concentration was sprayed on seedlings at the fourth true leaf stage of cultivar: Asahi.
One day after the spraying, a conidial suspension of the rice and sesame leaf blight fungus was spray inoculated.

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

As a comparison agent, a commercially available fungicide having a chemical name of 2,4-dichloro-6(o-chloroanilino)-1,3,5-triazine was used.

Test Example 3 Tomato late blight control effect test A hydrating agent prepared according to Example 2 on tomato seedlings (quality 2 world's best, 2nd true leaf stage seedlings) cultivated in clay pots with a diameter of 9 crrL in a greenhouse. A chemical solution diluted with water to a predetermined concentration was sprayed in an amount of 10 ml per pot using a pressure sprayer.

One day after the spraying, zoosporangia of tomato Phytophthora fungi formed on potato tubers were diluted and suspended in water, and the suspension was inoculated onto tomato leaves by drip.

After inoculation, it was kept at a humid temperature of 20°C (humidity 95-98%) and adjusted 3 days later, and the control value was calculated using the following formula.

Next, the test results are shown in Table 3.

As a comparison agent, a commercially available fungicide whose chemical name is Manganese ethylene bisdithiocarbamate was used.

Claims (1)

[Claims] 1 General formula (wherein X represents a lower alkyl group, a lower alkoxy group, or a halogen atom, n represents an integer of 0 or 1 to 3, and when n is 2 or more, X is An acetanilide derivative represented by R represents a lower alkyl group, which may be the same or different. 2 General formula (wherein X represents a lower alkyl group, lower alkoxy group or halogen atom, n represents O or an integer from 1 to 3, and n is 2 or more, even if the Xs are the same) 1. An agricultural and horticultural fungicide characterized by containing an effective portion of an acetanilide derivative represented by the following formulas (which may be different from each other, and R represents a lower alkyl group).