JPS5965074A - 2-phenyl-4,5,6,7-tetrahydro-2h-isoindole derivative, its preparation and herbicide containing it as active ingredient - Google Patents

Abstract

NEW MATERIAL:A 2-phenyl-4,5,6,7-tetrahydro-2H-isoindole derivative shown by the formula I (R1 is H, or lower alkyl; R2 is lower alkyl, lower alkenyl, cycloalkyl, phenyl, or aralkyl; X is halogen). EXAMPLE:2-( 2-Fluoro-4-chloro-5-ethylthiocarbonylmethoxy )phenyl-4,5,6,7-tetrahydro-2H-isoindole. USE:Useful as a herbicide. Effective against various kinds of weeds in plowed field such as broadleaf weeds, e.g., spleen amaranth, etc., gramineous weeds such barnyard grass, gramineous weeds such as Echinochloa oryzicola Vasing, etc. in paddy field, broadleaf weeds such as false pimpernel, etc., and weeds in paddy field. PROCESS:A compound shown by the formula II is reacted with a haloacetic acid thiol ester shown by the formula III (Y is halogen) to give a compound shown by the formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R1 is a hydrogen atom or a lower alkyl group, R2
represents a lower alkyl group, lower alkenyl group, dichlorofurkyl group, phenyl group or aralkyl group, and X represents a halogen atom. ] 11 phenyl &, j; A
, 7-titrahydro, 2H-isoindole derivative (
Hereinafter, it will be referred to as the compound of the present invention. ), its production method, and herbicides containing it as an active ingredient.

The compounds of the present invention can be used to treat various weeds that are problematic in the treatment of foliage and soil in upland areas, such as broad-leaved weeds such as Japanese radish, Japanese radish, Japanese radish, Japanese radish, Japanese radish, Japanese radish, Japanese moss, Japanese staghorn, and other weeds. , Japanese barnyard grass, Japanese barnyard grass, wild foxtail grass,
Some of the compounds of the present invention have a herbicidal effect on grass weeds such as oat, and do not cause any problematic phytotoxicity to major crops such as corn, wheat, soybean, and cotton.

Furthermore, the compound of the present invention has a herbicidal effect on various weeds that are problematic in paddy fields, such as grass weeds such as Japanese grasshopper, broad-leaved weeds such as 7 xena, kikashigusa, and chickweed, and paddy field weeds such as paddy field weed. It does not show any harmful effects on rice.

The compound of the present invention can be used as an active ingredient of a herbicide in paddy fields, fields, orchards, pastures, forests, non-agricultural lands, etc.

The compound of the present invention has the general formula [wherein, X represents the same meaning as above]. ]Hydroxyphenyl-&, j, A.

7-titrahydrojH-isoindole conductor and/~
/, 5 equivalents of the general formula [wherein R1 and R2 represent the same meanings as above, Y
represents a halogen atom. ] in a solvent, preferably /~/,! It can be produced by reacting for θ°C to /jθ°C, θ, S hours to /θ hours in the presence of an appropriate amount of a dehydrohalogenating agent.

Solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, chloroform, carbon tetrachloride, dichloroethane,
Halogenated hydrocarbons such as chlorobenzene and dichlorobenzene, diethyl ether, diisopropyl ether,
Ethers such as dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone,
Ketones such as cyclohexanone, esters such as ethyl acetate and butyl acetate, nitrides such as nitroethane and nitrobenzene, nitriles such as acetonitrile and isobutyronitrile, pyridine, triethylamine 1. N, N-
Tertiary amines such as diethylaniline, tributylamine, N-methylmorpholine, N,N-dimethylform7
Examples include acid amides such as amide and acetamide, sulfur compounds such as dimethyl sulfoxide and sulfolane, and mixtures thereof.

Dehydrohalogenating agents include lysine, triethylamine,
Examples include organic bases such as N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate, and alkali metal flukoxides such as sodium methoxide and sodium ethoxide.

After the reaction is completed, usual post-treatments are carried out, and if necessary, purification is carried out by chromatography, distillation, recrystallization, etc.

Next, a production example of the compound of the present invention will be shown. Production Example (Production of Compound of the Present Invention) -1(-1 fluorauderchloro-5-hydroxy)phenyl-'l,3,A,? -Tetrahydro +2
H-isoindol, gy, e-ethyl α-bromothioacetic acid 31 and anhydrous potassium carbonate q, sy were heated under reflux for 3.5 hours in 30 ml of acetonitrile. The reaction solution was poured into diluted hydrochloric acid, extracted with ethyl acetate, and the solvent was distilled off under reduced pressure to give 1,2-(j-fluoro-guchloro-j-ethylthiocarbonylmethoxy)phenylrug, t, g, 7
-Tetrahydro-2H-isoindole S¥ was obtained. This was purified by silica gel chromatography (developing solvent: hexane-ethyl acetate), m, 1), //6~//
White crystals were obtained at 2°C.

This product can be manufactured by such a manufacturing method.

Some of the intermediate compounds are shown in Table 1.

Table 1: When using the compound of the present invention as an active ingredient of a herbicide,
It is usually mixed with solid carriers, liquid carriers, surfactants, and other formulation auxiliaries to formulate emulsions, aqueous solutions, suspensions, granules, etc.゛These preparations contain the compound of the present invention as an active ingredient in a weight ratio of θ, /~? It contains S%, preferably / ~ θ.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and synthetic hydrous silicon oxide. 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, and acetonitrile. , water, etc.

Surfactants used for emulsification, dispersion, wetting, etc. include negative salts such as alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, and polyoxyethylene alkylaryl ether phosphate salts. ionic surfactant, polyoxyethylene alkyl ether, polyoxyethylene furkyl 7-lyl ether,
Examples include nonionic surfactants such as polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxysorbitan fatty acid esters.

Formulation auxiliaries include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, 0M0 (carboxymethylcellulose), PAP (isopropyl acid 9phosphate), and the like.

Examples of formulations are shown below. The compounds of the present invention are shown by compound numbers in Table 7. Parts indicate parts by weight.

Formulation Example: 50 parts of the compound of the present invention, 3 parts of calcium lignosulfonate, part of sodium lauryl sulfate, and part of synthetic hydrous silicon oxide are thoroughly ground and mixed to obtain an irrigation agent.

Formulation Example 2 70 parts of the compound of the present invention, 4 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzenesulfonate, 30 parts of xylene and 1290 parts of cyclohexane are thoroughly mixed to obtain an emulsion.

Formulation Example 3 Compound of the present invention/θ, 2 parts, synthetic hydrous silicon oxide/part, calcium lignosulfonate 2 parts, bentonite 30 parts, and 6 parts of kaolin clay were thoroughly pulverized and mixed, water was added, and the mixture was thoroughly kneaded. The granules are dried to obtain granules.

Formulation Example: 7.23 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, OMC+ 'A'.

A suspension is obtained by mixing with 6 parts of water and wet grinding until the particle size of the active ingredient is less than 5 microns.

These preparations can be used as is or diluted with water, etc., and treated with foliage or soil. For soil treatment, the preparation can be applied to the soil surface (if necessary, mixed with the soil after application) or irrigated into the soil.

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 θ, /7 to /θθ7 per are, preferably θ, 22 to sot, and is applied in emulsions, wettable powders, suspensions, etc. should be applied by diluting it with water (if necessary, adding a spreading agent such as a spreading agent) at a rate of /liter to /θliter per area, and granules, etc., should be applied as is without any dilution. .

Spreading agents include the surfactants mentioned above, 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 7, and the compounds used for comparison are indicated by the compound symbols in Table 7.

Evaluation of chemical damage to crops and efficacy against weeds in each test example below in Table 1 was made by measuring the dry weight of the above-ground parts of the plants that remained withered at the time of the survey, and comparing the dry weight with the untreated plot (
＠ is calculated and shown in 6 levels of numbers from θ to j based on the criteria in Table 3. Table μ Experimental example / Upland soil mixing treatment test Diameter / θ (7), Depth / θ□□ Field soil was filled in □ cylindrical plastic pots, and cotton, morning glory, Japanese radish, and soybean were sown and preserved. The test compound made into an emulsion according to Formulation Example λ was diluted with 10 liters of water per volume. Grow in a greenhouse for 2θ days after spraying,
The herbicidal efficacy was investigated. The results are shown in Table 4.

Test Example - Upland Stem and Leaf Treatment Test A cylindrical plastic pot with a diameter of /θ saw and a depth of /θcnr was filled with field soil, and barnyard grass, oat, radish, and Japanese radish were sown and grown in a greenhouse for /θ days. After that, the test compound made into an emulsion according to the formulation example
It was diluted with water containing a spreading agent equivalent to θ liters, and its grass efficacy was examined in 8:14. The results are shown in Table 3.

Table 3 Test Example 3 Paddy soil treatment test A cylindrical plastic pot with a depth of 12 cm was filled with paddy soil, and seeds of Japanese millet and broad-leaved weeds (Azaena, Kikashigusa, Chickweed) were added to the diameter. After soaking the rice and making it into a paddy field, tubers of Urikawa were buried at a depth of 7 to 2 cm, and then rice at the small leaf stage was transplanted and grown in a greenhouse. After 6 days ( At the early stage of each weed's emergence, apply 70% of the test compound prepared as an emulsion according to Formulation Example 2.
It was diluted with S milliliters of water per pot, and a predetermined amount of it was dropped onto the water surface. After dripping! The plants were grown in a greenhouse for θ days and their herbicidal efficacy was investigated. The results are shown in Table 6.

Table 6 Test Example q Field soil stem leaf treatment test area-'l 3x, 2 J td,, depth //Ca1
Fill the 1st vat with field broom, corn, wheat,
Seeds of daisies, American hornworts, Japanese fir trees, Japanese croakers, Japanese morning glories, bluebells, and goldenrods;
/I grew it for days. After that, formulation examples! The test compound made into an emulsion according to
Sprayed evenly over the entire stem and leaves from above one object. At this time, the growth of each plant differed depending on the grass species, but the plant height was 2 to 2 cvr at the leaf stage. The herbicidal efficacy was investigated 30 days after spraying. The results are shown in Table 7. In addition, the actual performance (
The experiment was conducted in a greenhouse throughout the entire period.

Claims (1)

[Claims] (1) General formula [In the formula, "1 represents a hydrogen atom or a lower aralkyl group, R
2 represents a lower alkyl group, lower alkenyl group, cycloalkyl group, phenyl group or aralkyl group, and X represents a halogen atom. ] 1-1 phenylrug, 3,6.7-titrahydro 2H-isoindole derivative. (λ) General formula [in the formula, or represents a halogen atom. ]Hydroxyphenyl- &, 'j, 4゜7-titrahydro,
2H-isoindole derivative and the general formula [wherein, R1 is a hydrogen atom or a lower alkyl group, R2
represents a lower alkyl group, lower alkenyl group, cycloalkyl group, phenyl group or aralkyl group, and Y represents a halogen atom. [In the formula, R1, R2 and X have the same meanings as above. ] Indicated by! - A method for producing a phenylrug, j, 4,7-titrahydro, 2H-isoindole derivative. (3) General formula [In the formula, R1 is a hydrogen atom or a lower alkyl group, R2
represents a lower alkyl group, lower alkenyl group, cycloalkyl group, phenyl group or aralkyl group, or a halogen atom. ] A herbicide characterized by containing as an active ingredient a cophenylinyl, S, A, 7-titrahydro, 2H-isoindole derivative.