JPS5951952B2 - Anilide derivatives and agricultural and horticultural fungicides - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel anilide derivatives represented by the following general formula and agricultural and horticultural fungicides containing these derivatives as active ingredients.

The novel anilide derivatives of the present invention are represented by the general formula, where R represents a hydrogen atom or a lower alkyl group, X represents a lower alkyl group, a halogen atom, or a lower alkoxy group, and Y represents a lower It represents an alkyl group or a halogen atom, m represents an integer of 0.1 to 3, and n represents an integer of 0.1 to 2.

Examples of the lower alkyl group in R, X and Y above include methyl group, ethyl group, propyl group and butyl group.

Examples of halogen atoms in X and Y include chlorine atom, bromine atom, iodine atom and fluorine atom. X
Examples of lower alkoxy groups include methoxy, ethoxy, propoxy and butoxy groups. Furthermore, X can be bonded to any position from the 2nd to 6th positions of the phenyl group to which it is bonded, particularly the 2nd, 4th,
Preferably, it is bonded to the 2,4 or 2,4,5 positions.
Further, Y can be bonded to any position from the 2nd to 6th position of the phenyl group to which it is bonded, and is particularly preferably bonded to the 2nd, 4th, or 2nd and 4th positions. The present inventors synthesized a large number of anilide derivatives and conducted intensive research on their practicality as agricultural and horticultural fungicides.

As a result, it has been found that the novel compound group represented by the general formula (1) has control activity against rice blast, tomato late blight, and cucumber rot, and is useful as a fungicide for agriculture and horticulture. The compound of general formula (1) according to the present invention can be produced by the method of the following formula.

reaction formula Next, examples will be shown regarding the production of the compounds of the present invention.

Example 1N-benzyl-N-(furan-2'-carbonyl)-2,6-dimethylaniline (compound 1)N-
Benzyl-2,6-dimethylaniline 84.49 (0.
57.2 g (0.4 mol) of 2-furoyl chloride
4 mol), triethylamine 50f! (0.5 mol) and benzene 500a were added and the mixture was stirred at 40-50°C for about 2 hours, then the reaction was washed with alkali and water and concentrated.

The concentrate was recrystallized from methanol and water to obtain the desired product 1099 in the form of colorless needles. Melting point: 76.5-77.5°C.
Example 2 N-(1'-phenyl-ethyl)-N-(furan-(2
') monocarbonyl)-2,6-dimethylaniline (compound 2) N-(1'-phenyluethino(he)-2,6
- Dimethylaniline 90.09 (0.4 mol), 2-fukyl chloride 57.29 (0.44 mol), potassium carbonate 60.79 (0.44 mol) and acetone 250 d
was added, and the resulting mixture was heated at 50-60°C for 2-3 hours.
After stirring for an hour, the mixture was poured into ice water.

After filtering out the precipitated crystals, the crystals were recrystallized from methanol and water to obtain the desired product 1109 as pale yellow needle-like crystals. melting point 12
9-130℃. Next, Table 1 illustrates the compounds of the present invention obtained according to the method of the above examples.

Note that the compound considerations in the table are also referred to in the following Examples and Test Examples. When the compound of the present invention is used as an agricultural and horticultural fungicide, it can be used as a powder, wettable powder, emulsion, granule, fine granule, or other commonly used forms.

The carrier used in the present invention may be either solid or liquid, and is not limited to a specific carrier. Examples of solid carriers include various clays, kaolin, clay,
Examples include diatomaceous earth, talc, silica, etc. Liquid carriers include those that serve as a solvent for the active ingredient compound according to the present invention, and those that can disperse or dissolve the active ingredient compound with an auxiliary agent even if they are non-solvents. If so, you can use it. Examples include benzene, xylene, toluene, kerosene, alcohols, ketones, dimethyl sulfoxide, and dimethylformamide. A suitable surfactant and other auxiliary agents such as a spreading agent and a fixing agent are mixed with this,
Can be used as an aqueous solution or emulsion. Furthermore, the compound of the present invention can be used in combination with other fungicides, insecticides, herbicides, plant growth regulators, etc. to ensure labor-saving and pesticidal effects. Next, some examples of using the compounds of the present invention as agricultural and horticultural fungicides will be shown, but the main compounds and additives are not limited to the following examples. Example 3 (Powder) 2 parts of Compound A6l and 98 parts of clay are uniformly mixed and ground to obtain a powder containing 2% of the active ingredient.

Usually, the compound of the present invention is added to the powder as an active ingredient at a concentration of 1.5 to 1.
It contains 3% by weight and is powdered at a rate of 3 to 4 kg per 10 ares.

Example 4 (Wettable powder) 70 parts of Compound/162, 3 parts of calcium alkylbenzenesulfonate, 5 parts of polyoxyethylene nonyl phenyl ether, and 22 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 3000 times with water and spray it on plants. Usually, the compound of the present invention is contained as an active ingredient in a hydrating powder in an amount of 30 to 75% by weight, and this is diluted 600 to 3000 times with water to give 10% by weight per 10 ares.
Spray at a rate of 0 to 2001.

Example 5 (Emulsion) 60 parts of compound 4 and methyl ethyl ketone 2
3 parts, polyoxyethylene nonyl phenyl ether 17
By mixing and dissolving these parts, an emulsion containing 60 fl of the active ingredient is obtained.

When using this product, dilute it 600 to 3000 times with water and spray it on plants. Usually, the compound of the present invention is contained as an active ingredient in an emulsion in an amount of 30 to 75% by weight, and this is diluted 600 to 3000 times with water to give a concentration of 100% by weight per 10 ares.
Spray at a rate of ~2001.

Example 6 (granules) 5 parts of compound 7167, 1 part of lauryl sulfate
．． 5 parts of calcium ligninsulfonate, 1.5 parts of calcium ligninsulfonate, 25 parts of bentonite, and 67 parts of clay are mixed with 15 parts of water in a kneader, granulated, and dried in a fluidized fluidized dryer to obtain 5% granules.

Usually, the compound of the present invention is contained in granules as an active ingredient for 5 to 15 days.
The content is 3 to 4 kg per 10 ares by weight.

Next, the pesticidal effect when the compound of the present invention is used as an agricultural and horticultural fungicide will be explained using test examples.

Test Example 1 Rice blast control effect test A hydrating powder prepared according to Example 4 was applied to third leaf stage seedlings of paddy rice (variety: Asahi) cultivated in clay pots with a diameter of 9 CfL in a greenhouse. A test chemical solution diluted to a specific concentration was sprayed.

One day after the spraying, a spore suspension of the blast fungus was inoculated by spraying.
After inoculation, leave overnight under humid room conditions (humidity 95-100%, temperature 24%).
The temperature was maintained at ~25°C. 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. In addition, chemical damage to rice was investigated using the following indicators.
The results are shown in Table 2. Indicator test example for investigation of chemical damage 2 Tomato late blight control effect test Prepared according to Example 4 on tomato seedlings (variety: Sekai Ichi, second true leaf stage seedlings) cultivated in clay pots with a diameter of 9C1n in a greenhouse. The wettable powder was diluted with water to a predetermined concentration, and a chemical solution was sprayed using a pressure sprayer.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R represents a hydrogen atom or a lower alkyl group,
represents a lower alkyl group, a halogen atom, or a lower alkoxy group, Y represents a lower alkyl group or a halogen atom, m represents an integer of 0, 1 to 3, and n represents 0, 1 to 3.
Anilide derivatives represented by (representing an integer of 2). 2 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R represents a hydrogen atom or a lower alkyl group,
represents a lower alkyl group, a halogen atom, or a lower alkoxy group, Y represents a lower alkyl group or a halogen atom, m represents an integer of 0, 1 to 3, and n represents 0, 1 to 3.
An agricultural and horticultural fungicide characterized by containing as an active ingredient an anilide derivative represented by (representing an integer of 2).