JPH042589B2 - - 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, and X represents a chlorine atom or a bromine atom. ] The present invention relates to a 3a-chloro-hexahydro-2H-isoindole-1,3-dione 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. Certain hexahydro-2H-isoindole-1,3-dione derivatives, such as 3a-chloro-2-(4-chloro-2-fluorophenyl)-
3a,4,5,6,7,7a-hexahydro-2H-
Isoindole-1,3-dione can be used as an active ingredient in herbicides as disclosed in US Pat.
It is described in the specification of No. 4120693. However, these compounds cannot always be said to be sufficient as active ingredients for herbicides. The compound of the present invention can be used to treat various problematic weeds in upland foliage treatment, such as freckle currant, Japanese knotweed, purslane, whiteweed, blueberry, white chestnut, shepherd's purse, American hornwort, Japanese commonweed, common goldenrod, yellowtail, and morning glory. , Marba Sagao, Seiyou Hill Gao, Himeodrikosou, Hottokenza, Youshi Yuchiyousen Azagao, Inunozuzuki, Gouinnofuguri, Furasabasou, Onamomi, Himawari, Inukamitsu, Inoukamizure, Inouvi, Innocorogusa, Mechisha, Mae -Kyushibira, Cat Rasugi, Seiban Mororo, etc. The compound of the present invention has a herbicidal effect on weeds of the Cyperaceae family, such as dayflowers, and weeds of the Cyperaceae family, such as Cyperaceae and Cyperaceae, and some of the compounds of the present invention have a problem with major crops such as corn, wheat, soybeans, and cotton. It does not show any drug damage. In addition, the compound of the present invention can be applied to various weeds that are problematic in paddy fields, such as grass weeds such as Japanese millet, broad-leaved weeds such as azalea, azalea, and chickweed; It has a herbicidal effect on paddy field weeds, and does not cause any harmful effects on rice. 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 or non-agricultural lands. The compound of the present invention has the general formula [In the formula, R and X have the same meanings as above. ] The hexahydro-2H-isoindole-1,3-dione derivative represented by the formula and a mixture of phosphorus pentachloride and phosphorus oxychloride are heated at 50°C to 100°C for 1 hour to
It can be produced by reacting for 24 hours. The amount of reagents used in the reaction is hexahydro-
Per equivalent of 2H-isoindole-1,3-dione derivative [], phosphorus pentachloride is used in an amount of 1.0 to 2.0 equivalents, and phosphorus oxychloride is used in a catalytic amount to an excess amount. 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 2 of the Invention) 2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-3a,4,5,6,
7,7a-hexahydro-2H-isoindole-
1 g of 1,3-dione was refluxed for 2 hours with 0.1 g of phosphorus oxychloride and 1.2 g of phosphorus pentachloride. After concentration,
Saturated sodium hydrogen chloride solution and chloroform were added for extraction.
The chloroform layer was washed with saturated sodium hydrogen chloride solution, dried, and concentrated. The residue was crystallized from methanol to give 3a-chloro-2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-3a,4,5,6,
7,7a-hexahydro-2H-isoindole-
0.7 g of 1,3-dione was obtained. mp121.5-122°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 raw material compound hexahydro-2H-isoindole-1,3
-Dione derivative [] has the general formula [In the formula, R and X have the same meanings as above. ] Aniline derivative and cyclohexane represented by
1,2-dicarboxylic anhydride in a solvent at 0℃~
It can be produced by reacting at 200°C for 1 to 24 hours. The amount of reagent to be used in this case is 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1.0 to 1 of cyclohexane-1,2-dicarboxylic anhydride per equivalent of aniline derivative [].
It is 1.1 equivalent. Solvents include water, acetic acid, propionic acid, toluene, xylene, 1,4-dioxane, and the like. After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, recrystallization, etc. Next, a production example of this hexahydro-2H-isoindole-1,3-dione derivative [] will be shown. Production example 2 4-chloro-2-fluoro-5-(1-methylethoxy)aniline 4.5g cyclohexane-1,
3.4 g of 2-dicarboxylic anhydride was heated under reflux with 20 ml of acetic acid for 3 hours. After cooling, water was added and extracted with ether. The ether layer was washed with sodium chloride water, dried, and concentrated. The residue is crystallized from ether/petroleum ether,
2-[4-chloro-2-fluoro-5-(1-methylethoxy)phenyl]-3a,4,5,6,7,
7a-hexahydro-2H-isoindole-1,
3.4 g of 3-dione was obtained. mp107-108°C When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, liquid carrier, surfactant, or other formulation auxiliary to form an emulsion, wettable powder, or
Formulate into suspensions, granules, etc. These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 1 to 95%, preferably 2 to 80%. Solid carriers include fine powders or granules such as kaolin clay, attapalgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrated silicon oxides. Liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isopropanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide,
Examples include acetonitrile and water. Surfactants used for emulsification, dispersion, wetting, etc. include anionic surfactants such as alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, and polyoxyethylene alkylaryl ether phosphate salts. Examples include nonionic surfactants such as surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. Formulation auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), and PAP (isolopyl acid phosphate).
etc. 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 50 parts of Compound 1 of the present invention, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate, 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 3 of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene and 40 parts of isophorone are thoroughly mixed to obtain an emulsion. Formulation Example 3 Compound 2 of the present invention, 2 parts, synthetic hydrated silicon oxide 1
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 25 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water are mixed and wet-pulverized until the particle size becomes 5 microns or less to obtain a suspension. These preparations are used as they are or diluted with water for soil treatment, foliage treatment, or flooding treatment.
In addition, soil treatment includes soil surface treatment, soil mixing treatment, etc., and foliage treatment includes spraying from above the crops and weeds, as well as spraying in a limited direction to prevent the chemicals from adhering to the crops. How to do it (local treatment)
etc. are included. 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 0.2 g per are.
~50g, preferably 0.5g~20g, emulsion,
Wettable powders, suspending agents, etc. are diluted with water (adding a spreading agent such as a spreading agent if necessary) and applied at a rate of 1 liter to 10 liters per are; granules, etc. , applied as is without any dilution. In addition to the above-mentioned surfactants, the spreading agent includes polyoxyethylene resin acid (ester), lignin sulfonate, abietate, dinaphthylmethane disulfonate, paraffin, 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. Evaluation is made on a 6-level scale from 0 to 5, with a score of 5 indicating that the test plant has died or its growth has been completely inhibited.
Indicated by 0, 1, 2, 3, 4, 5. Test example 1 Upland soil mixing treatment test Upland soil was packed into a vat with an area of 33 x 23 cm ² and a depth of 11 cm, and Seiban sorghum, crabgrass, European morning glory, Maruva morning glory, Japanese trumpet, and American golden deer were sown. It was covered with soil to a thickness of 2 cm. Make an emulsion of the test compound according to Formulation Example 2, dilute the specified amount with water, spray it on the soil surface with a miniaturized sprayer at a rate of 10 liters per are, and then apply it to the soil up to a depth of 4 cm. The surface layer was thoroughly mixed. In addition, corn, soybean, and cotton seeds were embedded to a depth of 2 cm. After spraying, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 3.

[Table] Test example 2 Field soil stem and leaf 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, cotton, soybean, American hornwort, Japanese morning glory, Japanese radish,
Seeds of blueberry and dogfish were sown and grown for 18 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the emulsion was diluted with water containing a spreading agent.
At a rate of 5 liters per area, the mixture was sprayed uniformly over the entire stem and leaves from the top of the plant using a miniaturized sprayer. At this time, the growth of each plant varied depending on the grass species, but it was in the 1-4 leaf stage and the plant height was 2-12 cm. Herbicidal efficacy was investigated 20 days after spraying. The results are shown in Table 4. This test was conducted in a greenhouse throughout the entire period.

[Table] Test example 3 Paddy soil and foliage treatment test Fill a 1/5000a Wagner pot with paddy soil.
Seeds of Japanese millet, broad-leaved weeds (Azeena, Japanese wattle, Japanese chickweed), and bulrush were mixed in at a depth of 1 to 2 cm. After flooding the fields to create a paddy field, tubers of Urikawa were buried at a depth of 1 to 2 cm, and then three-leaf stage rice was transplanted and grown in a greenhouse. Six days later (at the one-leaf stage of Japanese millet), the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the emulsion was diluted with water, and the emulsion was dropped onto the water surface at a rate of 10 milliliters per pot. 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】

Claims (1)

[Claims] 1. General formula [In the formula, R represents a lower alkyl group, and X represents a chlorine atom or a bromine atom. ] A 3a-chloro-hexahydro-2H-isoindole-1,3-dione derivative represented by: 2 General formula [In the formula, R represents a lower alkyl group, and X represents a chlorine atom or a bromine atom. ] A general formula characterized by reacting a hexahydro-2H-isoindole-1,3-dione derivative represented by the formula with a mixture of phosphorus pentachloride and phosphorus oxychloride. [In the formula, R and X have the same meanings as above. ] A method for producing a 3a-chloro-hexahydro-2H-isoindole-1,3-dione derivative shown in the following. 3 General formula [In the formula, R represents a lower alkyl group, and X represents a chlorine atom or a bromine atom. ] A herbicide characterized by containing a 3a-chloro-hexahydro-2H-isoindole-1,3-dione derivative represented by the following as an active ingredient.