JPH0480024B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula () [In the formula, R represents a saturated or unsaturated cycloalkyl group, a methyl group-substituted cycloalkyl group, or a saturated or unsaturated cycloalkylalkyl group, and X represents a chlorine atom or a bromine atom. ] The present invention relates to a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following, a method for producing the same, and a herbicide containing the same as an active ingredient. The present inventors have continued to research herbicides with high selectivity and excellent herbicidal efficacy in order to protect important crops such as soybean, cotton, wheat, corn, and rice from damage from weeds and maintain high yields. It's here.
As a result, it was discovered that the tetrahydro-2H-isoindole derivative represented by the general formula () exhibits extremely high herbicidal efficacy, especially in the post-emergence treatment of upland weeds, and has a high degree of selectivity for soybeans. , completed the invention. It is a well-known fact from numerous patents and literature that phenoxyacetic acid derivatives have strong herbicidal efficacy. However, some of these known phenoxyacetic acid derivatives have 4,5,6,7 on the phenyl nucleus.
- There is no one having a tetrahydroisoindole group, and no description regarding it has been made. On the other hand, it is described in Japanese Patent Publication No. 11940/1983 that 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivatives have herbicidal activity. However, there is no mention of phenoxyacetic acid derivatives, and as is clear from the later examples, the compounds of the present invention are based on conventionally known phenoxyacetic acid derivatives (for example, 2, 4, 5
-T) and 2-phenyltetrahydro-2H-
Isoindole derivatives (compound (A) in Examples,
It has superior properties compared to (B)). The compounds of the present invention exhibit high herbicidal efficacy against upland weeds in pre- and post-emergence treatments, and have excellent properties that cause little harm to soybeans, wheat, and corn. As mentioned above, when the compound of the present invention is used in a post-emergence treatment, it is extremely effective against broad-leaved weeds such as morning glory, Japanese sagebrush, Japanese snail, purslane, and brilliance, which are important weeds in soybean fields. As is clear from the examples, it is characterized by being less harmful and exhibiting high soybean selectivity, and is expected to be used in soybean fields. The compound of the present invention can also be used in rice fields, various grains, vegetables, orchards,
It is also useful as a herbicide for lawns, pastures, tea gardens, mulberry gardens, rubber gardens, forests, non-agricultural lands, etc. Next, a method for synthesizing the compound of the present invention will be described. The compound of the present invention is synthesized according to the following reaction formula. [In the formula, R and X are as described above, and Z represents a chlorine atom, a bromine atom, or an iodine atom. ] The phenol derivative represented by the general formula () is hydrogenated in a solvent such as dimethylformamide, acetonitrile, methyl ethyl ketone, dimethyl sulfoxide, or hexamethylene triamide phosphate, using a dehydrohalogenating agent such as a salt such as sodium carbonate or potassium carbonate, etc. By reacting with an α-haloacetate represented by the general formula () at 20 to 100°C, preferably 40 to 80°C, in the presence of a metallizing agent such as sodium or sodium alkoxide, or an organic base such as a tertiary amine. Can be synthesized. Next, Examples will be shown to provide a more detailed explanation of the compounds of the present invention. Example 1 2-(4-chloro-2-fluoro-5-cyclopentoxycarbonylmethoxyphenyl)-4,
5,6,7-tetrahydro-2H-isoindole-1,3-dione (compound (2)) 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-4,5,6,7- 3 g of tetrahydro-2H-isoindole-1,3-dione was dissolved in 20 ml of dimethylformamide, and 0.8 g of anhydrous potassium carbonate was added. Further, 2.1 g of bromoacetic acid cyclopentyl ester was added and stirred at 40°C to 50°C for 3 hours. After cooling, water was added and extracted with toluene. The extract was thoroughly washed with water and dried over anhydrous magnesium sulfate. The desiccant was removed and the mixture was concentrated under reduced pressure.
The residue was purified by silica gel column chromatography to obtain 1.4 g of colorless oil. n ^22.5 _D 1.5491 The compounds shown in Table 1 were synthesized in the same manner as in Example 1.

【table】

[Table] Table 2 shows the NMR spectra of the compounds shown in Table 1.
Shown below. Compound numbers are the same as in Table 1.

【table】

[Table] When actually using the compound of the present invention, it is recommended that it be manufactured into easy-to-use forms such as emulsions, wettable powders, suspension agents, granules, and powders according to conventional methods in the agricultural chemical formulation field. Common. In this case, the content of the compound of the present invention in each preparation is 0.1 to 90%, preferably 1 to 80%. In preparing these pharmaceutical products, solid carriers include, for example, carrion, bentonite, talum, diatomaceous earth, ziecrite, and synthetic hydrous silicon oxide.
Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, ketones such as cyclohexanone and isophorone, chlorobenzene, dimethylformamide, cellosolve, ethylene glycol, and water. Surfactants used for purposes such as emulsification, dispersion, and spreading include:
For example, polyoxyethylene alkyl ether,
polyoxyethylene alkylaryl ether,
polyoxyethylene styryl aryl ether,
Nonionic surfactants such as polyoxyethylene fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene oxypropylene polymer, and alkyl sulfate ester salts, alkyl sulfonates, dialkyl sulfosuccinates,
Examples include anionic surfactants such as alkylaryl sulfonates, and these may be used alone or in combination. Furthermore, if necessary, lignin sulfonate, polyvinyl alcohol, or cellulose derivatives such as methyl cellulose can be used as adjuvants. Of course, the carriers, surfactants, etc. that can be used are not limited to those shown here. Next, a specific explanation will be given by giving a formulation example, but it goes without saying that the formulation ratio and carrier can be changed. Note that parts in each example indicate parts by weight. Formulation example 1 Compound (1) 20 parts, polyoxyethylene alkylaryl sulfate 2 parts, lignin sulfonic acid calcium salt 2 parts, synthetic hydrated silicon oxide (hydrated synthetic silicone dioxide) 15 parts, and diatomaceous earth 61 parts Thoroughly grind and mix to obtain a wettable powder. Formulation Example 2 80 parts of compound (3), 7 parts of polyoxyethylene alkylaryl ether, 3 parts of alkylaryl sulfonate and 10 parts of xylene are thoroughly mixed to obtain an emulsion. Formulation Example 3 1 part of compound (1), 1 part of synthetic hydrated silicon oxide, 5 parts of lignin sulfonate and 93 parts of clay are thoroughly ground and mixed, water is added, the mixture is thoroughly kneaded, and then granulated and dried to obtain granules. . Formulation Example 4 3 parts of compound (5), 0.5 parts of isopropyl phosphate, 66.5 parts of clay and 30 parts of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 20 parts of compound (9) was mixed with 60 parts of an aqueous solution containing 3% by weight of polyoxyethylene sorbitan monooleate, emulsified and suspended until the particle size of the active ingredient became 10μ or less, and then a dispersion stabilizer was added. 20 parts of an aqueous solution containing 3% by weight of sodium alginate were mixed to obtain 100 parts of a suspension preparation. When the compound of the present invention is used either before or after germination, the application rate can vary over a fairly wide range, but is usually 0.01 to 100 g per are;
Preferably it is 0.1-30g. Furthermore, the compound of the present invention can be mixed with other herbicides in order to improve its effectiveness as a herbicide, and in some cases, a synergistic effect can be expected. Furthermore, the compound of the present invention can be mixed with insecticides, nematicides, fungicides, plant growth regulators, fertilizers, etc., if necessary. Next, the compounds of the present invention will be explained in more detail by giving examples related to herbicidal efficacy. Note that control compounds in Examples are listed in Table 3. All evaluations of chemical damage to crops and efficacy against weeds in the following Examples were expressed as integer evaluation values from 0 to 5 in accordance with the criteria described below. The dry weight of the above-ground parts of the plants that remained withered at the time of the survey was measured, and the ratio (%) compared to the untreated area was calculated. The chemical damage and herbicidal efficacy of crops and weeds are evaluated from 0 to 5 based on the criteria shown in the table below.
Evaluated by numbers up to.

[Table] Example 2 Field-like stem and foliage treatment test Field soil was filled in a vat with an area of 33 x 23 cm ² , and purslane, common morning glory, Japanese commonweed, Japanese commonweed,
Seeds of Japanese soybean and soybean were sown and grown for 18 days. Thereafter, each compound was made into an emulsion, a predetermined amount was diluted with water, and the mixture was uniformly treated from the top of the plant to the entire stem and leaf area using a small sprayer. The amount of water sprayed is 10
The ratio was set to /a. The growth status of each weed at the time of treatment differed slightly depending on the grass species, but it was generally in the 2-4 leaf stage and the plant height was 2-12 cm. Twenty days after treatment, the herbicidal efficacy and crop damage of each compound were investigated. The results are shown in Table 4. This test was conducted in a greenhouse throughout the entire period.

【table】

[Table] Example 3 Field soil treatment test Fill a 1/5000a Wagner pot with field soil,
Seeds of morning glory, Japanese crocodile, soybean, and corn were sown and covered with soil to a thickness of 1 cm. Thereafter, a predetermined amount of the compound formulated into an emulsion was sprayed onto the soil surface using a small sprayer. In addition, the amount of water sprayed is
The ratio was set at 10/a. After 3 weeks in the open air, the herbicidal efficacy and crop damage of each compound were investigated.

【table】

【table】

Claims (1)

[Claims] 1. General formula [In the formula, R represents a saturated or unsaturated cycloalkyl group, a methyl group-substituted cycloalkyl group, or a saturated or unsaturated cycloalkylalkyl group, and X represents a chlorine atom or a bromine atom. ] A 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following. 2 General formula ZCH ₂ CO ₂ R [In the formula, Z is a chlorine atom, a bromine atom, or an iodine atom, and R is a saturated or unsaturated cycloalkyl group, a methyl group-substituted cycloalkyl group, or a saturated or unsaturated cycloalkyl group. Represents a cycloalkylalkyl group. ] α-Haloacetic acid ester and the general formula [In the formula, X represents a chlorine atom or a bromine atom. ] A general formula characterized by reacting the tetrahydro-2H-isoindole derivative represented by in the presence of a dehydrohalogenating agent. [In the formula, R and X are as described above.] ] A method for producing a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative. 3 General formula [In the formula, R represents a saturated or unsaturated cycloalkyl group, a methyl group-substituted cycloalkyl group, or a saturated or unsaturated cycloalkylalkyl group, and X represents a chlorine atom or a bromine atom. ] A herbicide characterized by containing a 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by the following as an active ingredient. 4. The herbicide according to claim 3, wherein the herbicide is a soybean herbicide.