JPS5951951B2 - 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 X represents a lower alkyl group, m represents an integer of 0, 1 or 2, and R represents an alkyl group, an alkoxyalkyl group, an alkylthio It represents an alkyl group, a furyl group or a 7-enyl group, and the phenyl group may be substituted with a lower alkyl group, a lower alkoxy group or a halogen atom.

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

X can be bonded to any position from 2 to 6 of the phenyl group to which it is bonded, particularly at the 2-, 6-, or 2-,
Preferably, it is attached at the 6-position. In R, examples of alkyl groups include methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl and octyl; examples of alkoxyalkyl include methoxymethyl and ethoxymethyl; alkylthioalkyl Examples of groups include isopropylthiomethyl groups, respectively.

When R is a lower alkyl group, a lower alkoxy group, or a halogen-substituted funynyl group, examples of the lower alkyl group are methyl, ethyl, propyl, and butyl; examples of the lower alkoxy group are methoxy ethoxy, propoxy, and butoxy groups; examples of halogen atoms include chlorine, bromine, iodine, and fluorine, respectively. These groups can be bonded to any position from the 2nd to 6th positions of the phenyl group to which they are bonded, and bonding to the 2nd, 4th, or 2,4th positions is particularly preferable. We synthesized a large number of 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.

In the formula, X, m and R have the same meanings as above.

Next, examples will be shown regarding the production of the compounds of the present invention. Example 1N-furfuryl-2-Blue 2/,6/-dimethylanilide (compound 7f61) N-furfuryl-2,6-
2-furoyl chloride 1.39 (0.01 mol) was added to a solution of 2.09 (0.01 mol) of dimethylaniline and 1.09 (0.01 mono(c)) of triethylamine dissolved in 50 ml of benzene while stirring at room temperature. ) was added dropwise.

After the dropwise addition, the mixture was refluxed for 3 hours to complete the reaction. After cooling, the mixture was washed with dilute hydrochloric acid and water in that order, and dehydrated with 39% of anhydrous sodium sulfate. Concentrate the solution, add hexane to precipitate crystals, and obtain the desired colorless prism crystal 0.7f! I got it. This product showed a melting point of 101.6°C. Cl8Hl7NO3
The results of elemental analysis were as follows. Example
2 N-Furfuryl-methoxyacetanilide (Compound.4
67) 2.09 (0.02 mol) of methoxyacetyl chloride was added to a solution of 3.4 g (0.02 mol) of N-furfuryl-aniline and 2.09 (0.02 mol) of triethylamine dissolved in 50 d of benzene while stirring on ice. ) was added dropwise.

The mixture was returned to room temperature and further heated at 50°C for 3 hours to complete the reaction. After cooling, the mixture was washed with dilute hydrochloric acid and water in that order, and then dehydrated with anhydrous magnesium sulfate (29g). After the solvent was distilled off, the residue was recrystallized from a small amount of a mixed solvent of benzene/hexane to obtain the desired product 1.0f1 in the form of colorless brism crystals. This product showed a melting point of 52.7°C. Nuclear magnetic resonance spectrum δ(
Solution) 3.3 (0CH3, 1 piece), 3.8 ( - N -
CH2-), 4.8(-CO- CH2- O-
, 1), and the compounds of the present invention produced according to such Examples are illustrated in Table 1.

Note that the compound considerations in the table are also referred to in the following examples and tests. 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. Any carrier or liquid used in the present invention may be used, and the carrier 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 a solvent for the active ingredient compound according to the present invention, and those that are non-solvents. Any auxiliary agent that can disperse or dissolve the active ingredient compound can also be used. Examples include benzene, xylene, toluene, kerosene, alcohols, ketones, dimethyl sulfoxide, and dimethylformamide. It can be used as an aqueous solution or emulsion by mixing a suitable surfactant and other auxiliary agents such as a spreading agent and a fixing agent. 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 the compound of Compound Taki 1 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 4k9 per 10 are.

Example 4 (Wettable powder) 70 parts of the compound of Compound Rinse 2, 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 in a hydrating powder in an amount of 30 to 75% by weight as an active ingredient, and this is diluted 600 to 3,000 times with water to give 10% by weight per 10 ares.
Spray at a rate of 0 to 200e.

Example 5 (Emulsion) 60 parts of Compound 4 and 60 parts of Compound 4. 23 parts of thyl ethyl ketone, 1 part of polyoxyethylene nonyl phenyl ether
By mixing and dissolving 7 parts, an emulsion containing 60% of the active ingredient is obtained.

When using this product, dilute it 600 to 3000 times with water and spray it on plants. Generally, the compound of the present invention is contained in an emulsion in an amount of 30 to 75% by weight as an active ingredient, 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 ~200e.

Example 6 (Granules) 5 parts of Compound 7, 1.5 parts of lauryl sulfate
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 fluid 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 in a greenhouse with a diameter of 9cm? A test chemical prepared by diluting a hydrating powder prepared according to Example 4 to a predetermined concentration was sprayed on third-leaf stage seedlings of paddy rice (variety: Asahi) cultivated in soil in clay pots.

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%).
~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. "IBP" which is a comparative drug
is a commercially available fungicide containing 0,0-diisopropyl S-benzyl phosphorothiolate (trade name Kitazine P emulsion)
It is.

Test example 2 Paddy rice sesame leaf blight control effect test in a greenhouse with a diameter of 9cm! A chemical solution diluted to a predetermined concentration was sprayed on the fourth true-leaf stage seedlings of paddy rice (variety: Asahi) cultivated in soil in clay pots, and one day after spraying, a conidial suspension of rice sesame leaf blight fungus was sprayed. Spray inoculated.

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, group, alkylthioalkyl group, furyl group, or phenyl group, and the phenyl group may be substituted with a lower alkyl group, a lower alkoxy group, or a halogen atom). 2 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, X represents a lower alkyl group, m is 0, 1 or 2
and R represents an alkyl group, an alkoxyalkyl group, an alkylthioalkyl group, a furyl group, or a phenyl group, and this phenyl group may be substituted with a lower alkyl group, a lower alkoxy group, or a halogen atom). An agricultural and horticultural fungicide characterized by containing an anilide derivative as an active ingredient.