JPS58135864A - 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative, its production method and herbicide containing it as an active ingredient - Google Patents

Abstract

NEW MATERIAL:A compound shown by the formulaI(R is saturated or unsaturated cycloalkyl, methyl group-substituted cycloalkyl, or cycloalkylalkyl; X is Cl or Br). EXAMPLE:2-( 4-Chloro-2-fluoro-5-cyclopentoxycarbonylmethoxyphenyl )-4, 5, 6, 7- tetrahydro-2H-isoindole-1,3-dione. USE:A herbicide for soybean. PROCESS:A phenol derivative shown by the formula II is reacted with an alpha-haloacetichaloalkyl ester shown by the formula III in a solvent such as DMF, acetonitrile, etc. in the presence of a dehydrohalogenating agent (e.g., sodium carbonate, sodium hydride) at 40-80 deg.C, to give a compound shown by the formulaI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to general formula (I) υ c, in which generally a saturated or unsaturated cycloalkyl group,
A cycloalkyl group substituted with a methyl 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 studied soybean, cotton, wheat, corn,
In order to protect important crops such as rice from weed damage and maintain high yields, we have continued to research herbicides with high selectivity and excellent herbicidal efficacy. As a result, it was discovered that a tetrahydro-2H-isoindole derivative represented by the general formula , completed the invention.

The fact that phenoxyacetic acid derivatives have strong herbicidal efficacy is that
This is a well-known fact from numerous patents and literature. However, among these known phenoxyacetic acid derivatives, none have a 4.5°6.7-titrahydroisoindole group in the phenyl nucleus, and there is no description regarding this.

10,000, 2-phenyl-4,5,6,7-tetrahydro-
It is described in Japanese Patent Publication No. 11940/1983 that the 2-isoindole conductor has emasculating activity. However, there is no mention of phenoxyacetic acid derivatives, and as is clear from the later examples, the compounds of the present invention do not contain conventionally known phenoxyacetic acid derivatives (such as 2.4.5-T) and It has superior properties compared to 2-phenyltetrahydro-2kl-isoindole derivatives (among the compounds in Examples)). 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 thorns, Japanese purslane, and Japanese 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 compounds of the present invention are also useful as herbicides for paddy fields, sI grains, vegetables, orchards, lawns, pastures, tea, mulberry orchards, rubber plantations, forests, non-agricultural lands, and the like.

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.

0 position) (I) [wherein R and Dehydrohalogenating agents such as salts such as sodium carbonate and potassium carbonate, metalizing agents such as sodium hydride and sodium alkoxide, tertiary amines, etc. in solvents such as methyl ethyl ketone, dimethyl sulfoxide, and hexamethylene triamide phosphate. It can be synthesized by reacting with an a-haloacetic acid haloalkyl ester represented by the general formula (2) at 20 to 100°C, preferably 40 to 86°C, in the presence of an organic base.

Next, Examples will be shown, and more detailed Example 1 of the compound of the present invention 2-(4-chloro-2-fluoro-5-cyclopentoxycarbonylmethoxyphenyl)-4,5,6,7-tetrahydro-2H-iso Indole-1,8-dione (
Compound C2)) 2-(4-chloro-2-fluoro-5-
Hydroxyphenyl)-4,5,6,7-titrahydro 2n-isoindole-1,8-dione (8I) was dissolved in dimethylformamide (20) and anhydrous potassium carbonate (0.
Added 8f.

2.1 # of bromoacetic acid cyclopentyl ester was added to the slurry and stirred at 40°C to 50°C for 8 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 from the P and concentrated under reduced pressure. Silica residue
Purification by gel column chromatography gave 1.41 as a colorless oil.

1 m, lin 1.5491 The compounds shown in Table 1 were synthesized in the same manner as in Example 1.

Table 1 The NMiL spectra of the compounds shown in Table 1 are shown in Table 2. Compound numbers are the same as in Table 1.

Table 2 When the compounds of the present invention are actually used, they are generally formulated into easy-to-use forms such as emulsions, wettable powders, suspensions, granules, and powders according to conventional methods in the agricultural chemical formulation field. It is true.

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 formulations, solid carriers such as kaolin, bentonite, talc, diatomaceous earth,
Examples include gicrite, synthetic hydrated silicon oxide, and the like. Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, ketones such as cyclohexanone and isiphorone, chlorobenzene, dimethylformamide, cellosolve, ethylene glycol, and water. emulsification, dispersion,
Examples of surfactants used for purposes such as expansion include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene fatty acid ester, and polyoxyethylene sorbitan Mufl.
K ester, oxyethylene oxypropylene polymer, and other nonionic surfactants; They may be used alone or in combination. Furthermore, if necessary, lignin sulfonate, privinyl 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 detailed explanation will be given by giving a formulation example, but it goes without saying that the distribution ratio and carrier can be changed. Note that parts in each example indicate parts by weight.

Formulation Example 1 20 parts of compound (1), 2 parts of polyoxyethylene alkylaryl sulfate, 2 parts of lignin sulfonic acid calcium salt, 16 parts of synthetic hydrated silicon oxide (hydrated synthetic silicone dioxide), and 61 parts of diatomaceous earth. Thoroughly grind and mix to obtain a wettable powder.

Formulation Example 2 Parts of the compound ts+so, 7 parts of polyoxyethylene alkylaryl ether, 8 parts of alkylaryl sulfonate and 10 parts of xylene are mixed to obtain an emulsion.

Formulation Example 8 1 part of compound (1), 1 part of synthetic hydrous silicon oxide, 5 parts of lignin sulfonate, and 98 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 4 518 parts of Compound C, 0.5 parts of isopropyl phosphate, 66.5 parts of clay, and 80 parts of talc are thoroughly ground and mixed to obtain a powder.

Formulation Example 6 20 parts of compound (9) was mixed with 60 parts of an aqueous solution containing 8% by weight of polyoxyethylene solhitane monooleate, emulsified and suspended until the particle size of the active ingredient became 10μ or more, and then dispersed. Mix 20 parts of water @f containing 8% by weight of sodium alginate as a stabilizing agent to obtain 100 parts of a suspension preparation.

When the compounds of this invention are used either on germination or post-emergence, the application rate can vary over a fairly wide range, but is usually 0.000. O1-10 (1, preferably 0.
1 to 809.

In addition, the compound of the present invention aims to improve its efficacy as a herbicide,
It is also possible to mix it with other herbicides, and in some cases a synergistic effect can be expected. Furthermore, the compound of the present invention can be mixed with insecticides, nematocides, cocoonicides, plant growth/articulation agents, fertilizers, etc., if necessary. .

Next, the compounds of the present invention will be explained in more detail by giving examples related to herbicidal efficacy.

The control compounds used in the test are listed in Table 8.

Table 8 All evaluations of chemical damage to crops and efficacy against fine leather in each of the following examples were conducted in accordance with the criteria described below.
It was expressed as an evaluation value using an integer from 0 to 5.

At the time of the survey, the dry weight of the above-ground parts of the dead plants is weighed, and the ratio (96) is calculated when compared with the untreated plot.

For crops and weeds, evaluate the medicinal potency and herbicidal efficacy on a scale from 0 to 5 based on the criteria shown in the table below.

Although it varies slightly, the plant height is generally 2 to 12 cm at the 2- to 4-leaf stage.
It was I11.

The herbicidal efficacy and production of crystalline compounds on the 20th day after treatment! g We investigated drug damage. The results are shown in R4.

This test was conducted in a greenhouse throughout the entire period.

Table 4 Crop damage Herbicidal efficacy Application amount
Nu compound ai a 1. A, ho'ba (I/a)
cormorant .

5 Gaz Zuzu Yuobi 0.4 1 55555 (1) 0.2 0 55554 0.4 0 55555 (2) 0.2 0 55555 0.1 0 54664 Example 4 Field soil treatment test 115000a Wagner pot was filled with field soil, Seeds of morning glory, Japanese yam, soybean, and corn were sown and covered with soil to a thickness of 1 clII.

Thereafter, a predetermined amount of the compound formulated into an emulsion was sprayed onto the soil surface using a small sprayer. The amount of water sprayed was set at a ratio of 10/a.

After this, the herbicidal efficacy and crop damage of each compound were investigated after 8 hours outdoors.

The results are shown in Table 5.

Table 6

Claims (1)

[Claims] (1) In the general formula c, 8 is a saturated or unsaturated cycloalkyl group,
A cycloalkyl group substituted with a methyl group or a saturated or unsaturated cycloalkylalkyl group, and X represents a chlorine atom or a bromine atom. ] 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative represented by these. General formula % formula % [In the formula, 2 is a chlorine atom, a bromine atom or an iodine atom,
R represents a saturated or unsaturated cycloalkyl group, a methyl group-substituted cycloalkyl group, or a saturated or unsaturated cycloalkylalkyl group. [In the formula, X represents a chlorine atom or a bromine atom. ] The general formula is characterized by reacting a tetrahydro-2-isoindole conductor represented by the following in the presence of a dehydrohalogenating agent [wherein and X are as described above]. ] 2-phenyl-4,5,6,7-tetrahydro-2■
-Production method of isoindole derivative. ■) General formula [wherein 8 is a saturated or unsaturated cycloalkyl group,
A cycloalkyl group substituted with a methyl group or a saturated or unsaturated cycloalkylalkyl group, and X represents a chlorine atom or a bromine atom. ] 1ζ herbicide characterized by containing the 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole conductor shown as an active ingredient ・′□ (4) The herbicide is for soybean use The herbicide according to claim 8, which is a herbicide.