JPH0369907B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula [In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkoxycarbonylmethyl group, and X represents a halogen atom. ] The present invention relates to the N-phenyltetrahydroisophthalimide derivative (hereinafter referred to as the compound of the present invention) represented by the formula (hereinafter referred to as the compound of the present invention), a method for producing the same, and a herbicide containing the same as an active ingredient. The compounds of the present invention can be used to treat various weeds that are problematic in pre-emergence soil treatment of upland fields, such as broad-leaved weeds such as Aspergillus spp., Japanese commonweed, Common morning glory, Aspergillus spp. It has a herbicidal effect on grass weeds such as grasses, and does not cause any harmful effects on major crops such as wheat, soybean, and cotton. In addition, the compound of the present invention has a herbicidal effect on broad-leaved weeds such as A. japonica, A. japonica, A. japonica, and a. It does not cause any harmful chemical damage to major crops such as. The compound of the present invention can be used in rice fields, fields, orchards, pastures,
It can be used as an active ingredient in herbicides for lawns, forests, non-agricultural lands, etc. The compound of the present invention has the general formula [In the formula, R and X have the same meanings as above. ] It can be produced by reacting the anilide derivative represented by the formula with 1 to 2 equivalents of a dehydration condensation agent in a solvent at -20°C to 100°C for 0.5 to 10 hours. Solvents include hexane, heptane, ligroin,
Aliphatic hydrocarbons such as petroleum ether, benzene,
Aromatic hydrocarbons such as toluene and xylene, halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, and diethylene glycol dimethyl ether; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, and cyclohexanone; esters such as ethyl formate, ethyl acetate, butyl acetate, and diethyl carbonate; nitrites such as nitroethane and nitrobenzene; and nitriles such as acetonitrile and isobutyronitrile. , tertiary amines such as pyridine, triethylamine, N,N-diethylaniline, tributylamine, and N-methylmorpholine, acid amides such as formamide, N,N-dimethylformamide, and acetamide, and sulfur such as dimethylsulfoxide and sulfolane. There are compounds, or mixtures thereof. The dehydration condensation agent includes carbodiimides such as dicyclocarbodiimide and diethylcarbodiimide, acid halogenating agents such as thionyl chloride, phosgene, and phosphorous oxychloride, or acylating agents such as ethyl chlorocarbonate, benzoyl chloride, and trifluoroacetic anhydride, and pyridine. Examples include organic bases such as triethylamine, and alkali metal salts such as potassium carbonate and sodium bicarbonate. After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, recrystallization, etc. Next, production examples of the compounds of the present invention will be shown. Production Example 1 (Production of Compound 5 of the Invention) 1 g of N-(2-fluoro-4-chloro-5-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalamic acid and 1 g of dicyclohexylcarbodiimide were added to toluene. Stirred in 20 ml for 4 hours at room temperature. It was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (eluent: hexane-ethyl acetate) to give N-(2-fluoro-4-
Chloro-5-propargyloxyphenyl)-3,
4,5,6-tetrahydroisophthalimide 0.7
I got g. Melting point: 114 DEG -116 DEG C. Some of the compounds of the present invention that can be produced by such a production method are shown in Table 1.

[Table] When producing the compound of the present invention, the anilide derivative of the general formula [], which is a raw material, has the general formula [In the formula, R and X have the same meanings as above. ] It can be produced by reacting the aniline derivative represented by 1 to 1.1 equivalents of 3,4,5,6-tetrahydrophthalic anhydride in a solvent at 10°C to 60°C for 0.5 to 10 hours. can. Solvents include hexane, toluene, chlorobenzene, tetrahydrofuran, dioxane, acetone, acetonitrile, N,N-dimethylformamide, dimethyl sulfoxide, or mixtures thereof. After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, recrystallization, etc. Next, an example of producing an anilide derivative of the general formula [] will be shown. Production Example 2 Add 0.8 g of 2-fluoro-4-chloro-5-propargyloxyaniline and 0.6 g of 3,4,5,6-tetrahydrophthalic anhydride to 20 ml of acetone,
Stirred at 40°C for 2 hours. The solvent was distilled off under reduced pressure, and N
1.4 g of -(2-fluoro-4-chloro-5-propargyloxyphenyl)-3,4,5,6-tetrahydrophthalamic acid was obtained. Melting point 110~112
℃ Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfate ester salts, alkyl (aryl) sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, etc. Examples include anionic surfactants, nonionic surfactants such as polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene polyoxypropylene brochure copolymer, sorbitan fatty acid ester, and polyoxysorbitan fatty acid ester. Formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol,
Examples include gum arabic, CMC (carboxymethyl cellulose), and PAP (isopropyl acid phosphate). When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant, and other formulation auxiliaries to form an emulsion, wettable powder, etc.
Formulate into suspensions, granules, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.05 to 95%, preferably 0.2 to 80%. Solid carriers include kaolin clay, attapulgiaite clay, bentonite, acid clay, pyrofluorite, talc, diatomaceous earth, calcite, walnut powder,
There are fine powders or granules such as urea, ammonium sulfate, and synthetic hydrous silicon oxide, and liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, acetone, cyclohexanone, Examples include ketones such as isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, and water. Examples of formulations are shown below. In addition, the compound of the present invention is the first
Indicated by compound number in the table. Parts indicate parts by weight. Formulation Example 1 Compound 1 of the present invention, 50 parts, calcium lignin sulfonate, 3 parts, sodium lauryl sulfate, 2 parts, and 45 parts of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain a wettable powder. Formulation Example 2 10 parts of Compound 2 of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene and 40 parts of cyclohexanone are thoroughly mixed to obtain an emulsion. Formulation Example 3 6, 2 parts of the compound of the present invention, 1 part of synthetic hydrated silicon oxide
1 part, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 4 5.25 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water were mixed and wet-pulverized until the particle size of the active ingredient became 5 microns or less to form a suspension. obtain. These preparations can be used as is or diluted with water, etc., and treated with foliage or soil. For soil treatment, the preparation is sprayed on the soil surface (if necessary, mixed with the soil after spraying) or the soil is irrigated. Furthermore, by mixing it with other herbicides, it can be expected to increase the herbicidal efficacy. Furthermore, it can be used in combination with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like. When the compound of the present invention is used as an active ingredient of a herbicide, the application amount is usually 0.03g per are.
~100 g, preferably 0.1 g to 30 g, and the amount of emulsions, wetting agents, suspending agents, etc. is 1 liter to 10 liters per are (if necessary, a spreading aid such as a spreading agent may be added). ) Dilute with water and apply; powders etc. should be applied as is without any dilution. In addition to the above-mentioned surfactants, spreading agents include polyoxyethylene resin acids (esters), lignin sulfonates, abietates, dinaphthylmethane disulfonates, paraffins, and the like. Next, test examples demonstrate that the compounds of the present invention are useful as active ingredients of herbicides. The compounds of the present invention are indicated by the compound numbers in Table 1, and the compounds used for comparison are indicated by the compound symbols in Table 2.

【table】

[Table] In addition, the herbicidal efficacy against weeds and crops is determined by visually observing the degree of germination and growth inhibition of the test plants during the survey, and ``0'' indicates that there is no or almost no difference from when no compound is tested. , rated on a 6-point scale from 0 to 5, with a score of 5 indicating that the test plant is dead or its growth is completely inhibited;
Shown as 1, 2, 3, 4, 5. Test Example 1 Upland Soil Mixing Treatment Test A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with upland soil, and barnyard grass, oats, morning glory, and Japanese radish were sown and covered with soil. The test compound made into an emulsion according to Formulation Example 2 was added per are.
It was diluted with 10 liters of water, and a predetermined amount of it was sprayed on the soil surface using a small sprayer, and the soil surface layer up to a depth of 4 cm was thoroughly mixed. After spraying, the plants were grown at room temperature for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 3.

【table】

[Table] Test Example 2 Field soil treatment test A cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm was filled with field soil, and barnyard grass, oats, radish, and Japanese radish were sown and grown in a greenhouse for 10 days.
Thereafter, the test compound made into an emulsion according to Formulation Example 2 was diluted with water containing a spreading agent equivalent to 10 liters per are, and a predetermined amount of the emulsion was sprayed on the foliage from above the plant using a small sprayer. After spraying, the plants were grown at room temperature for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 4.

【table】

[Table] Test Example 3 Paddy soil treatment test A cylindrical plastic pot with a diameter of 8 cm and a depth of 12 cm was filled with paddy soil, and 1 to 2 seeds of Japanese millet and broad-leaved weeds (Azaena, Azalea, and Chickweed) were added.
Mixed to a depth of cm. After flooding to create a paddy field, tubers of Urikawa were buried at a depth of 1 to 2 cm, and then rice at the two-leaf stage was transplanted and grown in a greenhouse. Six days later (at the beginning of each weed's emergence), the test compound made into an emulsion according to Formulation Example 2 was diluted with 5 milliliters of water per pot, and a predetermined amount thereof was dropped onto the water surface. After application, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 5.

【table】

[Table] Test example 4 Upland soil treatment test Upland soil was filled in a vat with an area of 33 x 23 cm ² and a depth of 11 cm, and soybeans, cotton, corn, morning glory, Japanese radish, blueberry, European morning glory, ragweed, and foxtail were sown. , 1~2cm
It was covered with soil to a thickness of . The test compound made into an emulsion according to Formulation Example 2 was diluted with water equivalent to 10 liters per are, and a predetermined amount thereof was sprayed onto the soil surface using a small sprayer. After spraying, the plants were grown outdoors for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 6.

【table】

[Table] Test example 5 Field soil treatment test Field soil was filled in a vat with an area of 33 x 23 cm ² and a depth of 11 cm, and corn, wheat, sugar beet, cotton, etc.
Soybeans, American hornworts, Japanese croakers, Japanese morning glories, blue-eyed violets, white-spotted violets, and white-spotted snails were sown and grown for 18 days. Thereafter, the test compound made into an emulsion according to Formulation Example 2 was diluted with water equivalent to 5 liters per are containing a spreading agent, and a predetermined amount of this was sprayed uniformly over the entire stem and leaf area from above the plant using a small sprayer. did. At this time, the growth of each plant differs depending on the grass species, but the plant height is 2 to 4 leaves at the 1- to 4-leaf stage.
It was ~12cm. Herbicidal efficacy was investigated 20 days after spraying. The results are shown in Table 7. This test was conducted in a greenhouse throughout the entire period.

【table】

Claims (1)

[Claims] 1. General formula [In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkoxycarbonylmethyl group, and X represents a halogen atom. ] N-phenyltetrahydroisophthalimide derivative represented by these. 2 General formula [In the formula, R represents a lower alkyl group, a lower alkenyl group, a lower alkynyl group, or a lower alkoxycarbonylmethyl group, and X represents a halogen atom. ] A herbicide characterized by comprising an N-phenyltetrahydroisophthalimide derivative represented by the following as an active ingredient.