JPS5967261A - Aminophenyltetrahydrophthalimide derivative, its preparation and herbicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The aminophenyltetrahydrophthalimide derivative of formula I (X is Cl or Br). EXAMPLE:N-(3-Amino-4-chloro-6-fluorophenyl)-3,4,5,6-tetrahydrophthalim ide. USE:A herbicide effective to broad-leaved weeds such as Indian mallow, Ipomea purpurea and graminaceous weeds such as Deccan grass, oats, etc. in plowed land or paddy field, and to the paddy field weeds such as monochoria, free from phytotoxicity to corn, wheat, rice, etc., and useful as an active component of a herbicide of paddy field, plowed land, orchard, pasture, lawn, etc. by foliar or soil treatment. PROCESS:The compound of formula I can be prepared by reducing the nitrophenyltetrahydrophthalimide derivative of formula II with 2-10 equivalent of iron powder in a solvent such as acetic acid in the presence of catalytic amount or large excess of an acid such as acetic acid, hydrochloric acid, etc. at 90- 120 deg.C for 1-24hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein X represents a chlorine atom or a bromine atom]. The present invention relates to an aminophenyltetrahydrophthalimide derivative represented by (hereinafter referred to as the compound of the present invention) and 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 foliar and soil treatments in upland areas, such as freckle currant, snail knotweed, purslane, whiteweed, and sagebrush.
, Japanese radish, Japanese radish, shepherd's purse, Japanese radish, Japanese radish, Japanese radish, field pansy, Japanese morning glory, American morning glory, Japanese morning glory,
It has a herbicidal effect against broad-leaved weeds such as staghorn grass, hotokenoza, japonica japonicus, spermia japonica, spermia japonica, sycamore, grasshopper, and grass weeds such as Japanese barnyard grass, barnyard grass, foxtail grass, blackgrass, black grass, oat, oat, etc. Moreover, the compounds of the present invention do not cause any problematic phytotoxicity to major crops such as corn and wheat.

In addition, the compound of the present invention can be applied to various weeds that are problematic in paddy fields, such as HIK of the Poaceae family such as Japanese millet, broadweeds of the Cyperaceae family such as Japanese cypress and Japanese chickweed, weeds of the Cyperaceae family such as Cyperus japonica and Japanese chickweed, and paddy fields such as Prunus japonicus and Prunus japonicum. It has a herbicidal effect on weeds and does not cause any harmful effects on rice.

The compounds of the present invention can be used in rice fields, fields, orchards, pastures, lawns,
It can be used as a sealing ingredient in forest or non-agricultural herbicides.

The compound of the present invention has the general formula [wherein, X is the same as 1. Represents M taste. ] and a nitrophenyltetrahydrophthalimide derivative represented by
It can be produced by reacting and reducing 10 equivalents of iron powder in a solvent in the presence of a catalytic amount to a large excess of acid at 90°C to 120°C for 11 to 24 hours.

Iron powder includes electrolytic iron, reduced iron, etc.

Solvents include diethyl ether, diisopropyl ether,
Ethers such as dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, fatty acids such as acetic acid and oleic acid, alcohols such as ethanol, isopropanol, t-butanol, octatool, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, water, etc. , a mixture of them (5) There is hardware.

Acids include organic acids such as acetic acid and mineral acids such as hydrochloric acid.

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

N-(4-chloro-2-fluoro-5-nitrophenyl)-8,4,5,6-titrahydrophthalimide 16.
2 g was dissolved in 200° C. of acetic acid and added dropwise to 30 g of 5% acetic acid water containing 14 g of iron powder at 90 to 100°C. After dropping, reflux for 1 hour. After cooling, chloroform was added and the mixture was distributed from house to house.

The organic layer of the ρ solution was separated, washed with saturated sodium bicarbonate solution, dried, and concentrated. The residue was crystallized and recrystallized from ether/petroleum ether to obtain 7.5 g of N-(8-amino-4-chloro-6-fluorophenyl)-8,4,5,6-te-1-rahydrophthalimide. Ta. mp 145.5~146.5°C
(6) Table 1 shows the compounds of the present invention that can be produced by such a production method.

Table 1 When producing the compounds of the present invention, the nitrophenyltetrahydrophthalimide derivative of the general formula [1r], which is a starting compound, is prepared by the general formula [1r], where X has the same meaning as above. ] and 1.0 to 1.1 equivalents of anhydrous 8
．． 4.5.6-titrahydrophthalic acid in a solvent at 0°
It can be produced by reacting at C to 200°C for 11 to 48 hours.

Solvents include toluene, xylene, 1,4-dioxane, acetic acid, propionic acid, water, and the like.

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 this nitrophenyltetrahydrophthalimide derivative having the general formula rID will be shown.

Production example 2 4-chloro-2-fluoro-5-nitroaniline 19g
8.4.5.6-titrahydrophthalic anhydride 15.2
The mixture was refluxed for 6 hours with g and 50 tnl of acetic acid. After cooling,
Water was added and extracted with toluene. The toluene layer was washed with water, saturated sodium bicarbonate solution, and water, dried, and concentrated. The residue was crystallized with methanol to give N-(4-chloro-2-fluoro-5-
Nitrophenyl)-8,4,5.

6-titrahydrophthalimide 209 was obtained.

mT) 157-157.5°C 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, wettable powders, suspensions, granules, etc.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.03 to 95%, preferably 0.1 to 80%.

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; liquid carriers Examples include aromatic group (9) 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, and dimethyl Examples include sulfoxide, acetonitrile, water, etc.

Surfactants used for emulsification, dispersion, wet layer, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Ionic surfactant J polyoxyethylene alkyl ether, polyoxyethylene alkylaryl 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, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate), and the like.

(10) Next, formulation examples will be shown. The compounds of the present invention are indicated by compound numbers in Table 1. Parts indicate parts by weight.

Formulation Example 1 2.50 parts of the compound of the present invention, 3 parts of calcium lignosulfonate, 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 1.10 parts of the compound 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 2.2 parts of the compound of the present invention, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignosulfonate, 30 parts of bentonite, and 65 parts of kaolin clay were thoroughly ground and mixed, water was added, and the mixture was thoroughly kneaded. The granules are dried to obtain granules.

Formulation Example 4 1.25 parts of the compound of the present invention, 8 parts of polyoxyethylene sorbitan monooleate), 3 parts of 0M0, 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. get.

These preparations can be used as they are 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 0.5 g to 100 g per are, preferably 1 g to 50 g, and emulsions, wettable powders, suspensions, etc. It is diluted with 1 to 10 liters of water (if necessary, a spreading agent such as a spreading agent is added) and applied. Granules and the like are applied as is without any dilution.

Spreading agents include, in addition to the above-mentioned surfactants, 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 2 In addition, the herbicidal efficacy against weeds and crops was determined by visual observation of the degree of germination and growth inhibition of the test plants during the survey. 0 to 5Q)6.
It is evaluated in stages and indicated as 0, 1.2.3.4.5.

Test Example 1 Upland Soil Mixing Treatment Test A cylindrical plastic pot with a diameter of 1 Ocrn and a depth of 10 parts M 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 diluted with water equivalent to 10 liters per are, and a predetermined amount of it was sprayed on the soil surface with a small sprayer, and then the surface layer of the soil up to a depth of 4 parts M was sprayed. Mixed well. After spraying, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 3.

Table 3 Test Example 2 Field soil stem and leaf treatment test Filled with field soil of Bat Yuuko with an area of 33 x 23 cm and a depth of 1 m, and seeded with corn, wheat, American staghorn, Japanese fir tree, Japanese velvet, Japanese morning glory, Aobifolia, and Japanese broom. , grown for 18 days. after that,
The test compound made into an emulsion according to Formulation Example 2 was diluted with water equivalent to 5 liters per area containing a spreading agent, and a predetermined amount of it was sprayed uniformly over the entire stem and leaves from above the plant using a small 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 m.

The 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.

Test Example 3 Paddy Soil Treatment Test A cylindrical plastic pot with a diameter of 8α and a depth of 12 cr IH was filled with paddy soil and treated with rice field weeds, broad-leaved weeds (Azaena, azalea, etc.).
Seeds (Kikashigusa, Chickweed) were mixed in to a depth of 1 to 2 cm. After flooding to create a paddy field condition, 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. 6 days later (initial stage of emergence of each weed)
The test compound prepared as an emulsion according to Formulation Example 2 was diluted with 5 milliliters of water per pot, and a predetermined amount of the solution was dropped onto the water surface.

After dropping, the plants were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated.

The results are shown in Table 5.

Table 5

Claims (3)

[Claims] (1) General formula [wherein, X represents a chlorine atom or a bromine atom]. ] An aminophenyltetrahydrophthalimide derivative represented by (2) General formula [wherein, X represents a chlorine atom or a bromine atom]. [In the formula, X represents the same meaning as above.] [In the formula, X represents the same meaning as above. ] A method for producing an aminophenyltetrahydrophthalimide derivative. (3) General formula [wherein, X represents a chlorine atom or a bromine atom]. ] A herbicide characterized by containing an aminophenyltetrahydrophthalimide derivative represented by the following as an active ingredient.