JPH03169859A - N-phenyltetrahydrophthalimide derivative and herbicide containing the same as active ingredient - Google Patents

Abstract

NEW MATERIAL:An N-phenyltetrahydrophthalimide derivative expressed by formula I (R1 is lower alkoxy, lower alkylthio or cycloalkyloxy; X is Cl or Br). EXAMPLE:2-(4-Bromo-2-fluoro-5-ethoxycarbonylmethyliminophenyl)-4,5,6,7- tetrahydro-2H-isoindole-1,3-dione. USE:Useful as a herbicide, having herbicidal effects on various weeds, e.g. broad- leaved weeds causing problems in foliar and soil treatment of farmland without phytotoxicity to main crops such as soybean and capable of exhibiting effects on weeds causing problems in paddy field without phytotoxicity to rice plant. PREPARATION:An aniline derivative expressed by formula II is reacted with a halocarboxylic acid ester expressed by formula III (Z is Cl or Br) in an amount of 1.0-10equiv. in a solvent at 0-200 deg.C to afford the compound expressed by formula I.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula [wherein R represents a lower alkoxy group, a lower alkylthio group or a cycloalkyloxy group, and X represents a chlorine atom or a bromine atom]. ] The present invention relates to an N-phenyltetrahydrophthalimide derivative (hereinafter referred to as the compound of the present invention) represented by the following and a herbicide containing the same as an active ingredient.

Certain N-phenyltetrahydrophthalimide derivatives, such as 2-(4-chloro-2-fluorophenyl)
The use of -4,5,6,7-tetrahydride-2H-isoindole-1,3-dione as an active ingredient in herbicides is described in JP-A-51-51521. However, these compounds cannot always be said to be sufficient as active ingredients in herbicides.

The compound of the present invention can be used to treat various weeds that are problematic in foliar and soil treatments in fields, such as purslane, whiteweed, Aobu (Aobu spp.), American hornwort,
The compound of the present invention has a herbicidal effect on broad-leaved weeds such as Japanese staghorn, American golden deer, American morning glory, Malva morning glory, European bindweed, European morning glory, Japanese Physalis, Japanese fir, sunflower, ragweed, and the like. It does not cause any harmful chemical damage to major crops.

In addition, some of the compounds of the present invention may be used to control various weeds that are problematic in rice fields, such as grass weeds such as Japanese grasshopper, broad-leaved weeds such as azalea, azalea, and chickweed; 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 an effective herbicide in forests or non-agricultural lands.

The compound of the present invention has the general formula [wherein, X represents the same meaning as above]. ] and 1. 0 to 10 equivalents of the general formula 0 11 Z-CH. CR. (I[I) [In the formula, 2 represents a chlorine atom or a bromine atom, and Rl represents the same meaning as above. ] in a solvent, in the presence or absence of a dehydrohalogenating agent of 0.5 to 1.0 equivalents, at 0°C to 200°C, 1.0
It can be produced by reacting for 96 hours.

Solvents include ethers such as diethyl ether, diisobutyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, methanol, ethanol, isobrobanol, and Alcohols such as butanol, octanol, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, nitrites such as acetonitrile and isobutyronitrile, viridine, triethylamine, N. Tertiary amines such as N-diethylaniline, tributylamine, N-methylmorpholine, formamide, N. N-dimethylformamide,
Acid amides such as acetamide, dimethyl sulfoxide,
These include sulfur compounds such as sulfolane, or mixtures thereof.

Dehydrohalogenation agents include organic bases such as pyridine, triethylamine, and N,N-diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, and sodium hydride, sodium methoxide, and sodium hydroxide. Examples include alkali metal alkoxides such as ethoxides.

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 6 of the Present Invention) 2-(3-amino-4-bromo-6-fluorophenyl') -4.5. 0.85 g of i,7-tetrahydride-2H-isoindole-1,3-dione was dissolved in 5 ml of 1.4-dioxane, 3.3 g of ethyl bromoacetate was added, and the mixture was refluxed for 6 hours. Furthermore, triethylamine 0.2
g was added thereto, and the mixture was refluxed for 1 hour. After cooling, water and toluene were added and extracted with toluene. The toluene layer was dried and concentrated, and the residue was purified using a silica gel column to obtain 2-(4-bromo-2-fluoro-5-ethoxycarbonylmethyliminophenyl)-4.5,6.7-tetrahydro-28-
1.0 g of isoindole-1.3-dione was obtained.
Table 1 shows some of the compounds of the present invention that can be produced by such a production method.

General Formula Table 1 When producing the compound of the present invention, the aniline derivative of the general formula (II) as a raw material compound is prepared by the general formula (wherein, X has the same meaning as above). The nitrobenzene derivative represented by ] and iron powder in an amount of zO to 1O in a solvent, in the presence of a catalytic amount to a large excess amount of acid, at 20°C to 200°C,
It can be produced by reacting for 0.5 to 24 hours.

Solvents include alcohols such as methanol and ethanol,
Examples include tetrahydrofuran, acetic acid, and water.

Examples of acids include hydrochloric acid and acetic acid.

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 the aniline derivative of the general formula (IF) will be shown as a reference example.

Reference example! 2-(4-chloro-2-fluoro5-nitrophenyl)-4.5.6.7-tetrahydro2H-isoindole-1,3-dione 16. 2 g of acetic acid 200-
5% acetic acid water containing 14g of iron powder dissolved in 30-90~
It was added dropwise at 100°C. After the addition, the mixture was refluxed for 1 hour. After cooling, chloroform was added and filtered.

The organic layer of the filtrate was separated, washed with saturated aqueous sodium bicarbonate, dried, and concentrated. The residue was crystallized and recrystallized from ether/petroleum ether to give 2-(3-amino-4-9ro-6-fluorophenyl)-4.5.6.7-tetrahydro-2H-isoindole-1.3-dione 7 .5g was obtained.

mp 144.5 ~ 1 4 6. 5°C Reference Example 2 In the same manner as in Reference Example 1, from 2-(4-bromo-2-fur-5-nitrophenyl)-45.6.7-tetrahydro-2H-isoindole-1.3-dione 2-
(3-amino-4-bromo-6-fluorophenyl)-
4.5,6.7-tetrahydride-2H isoindole-
I got 1,3-di.

mp 163-16 4. 5°C When using the compound of the present invention as an active ingredient of a herbicide,
Usually, solid carriers, liquid carriers, surfactants and other formulation auxiliaries are mixed to prepare emulsions, wettable powders, suspensions, granules, powders, etc.

These preparations contain the compound of the present invention as an active ingredient at a weight ratio of 0. It contains 1 to 95%, preferably 1 to 80%.

Solid carriers include fine powders or granules such as kaolin clay, attapulgite clay, bentonite, acid clay, pie phyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, and hydrated silicon oxide; liquid carriers Examples include aromatic hydrocarbons such as xylene and methylnaphthalene, alcohols such as isoprobanol, ethylene glycol, and cellosolve, ketones such as acetone, cyclohexanone, and isophorone, vegetable oils such as soybean oil and cottonseed oil, dimethyl sulfoxide, acetonitrile, There is water etc.

Surfactants used for emulsification, dispersion, wetting, etc. include alkyl sulfate salts, alkyl (aryl) sulfonate salts, dialkyl sulfosuccinate salts, polyoxyethylene alkylaryl ether phosphate salts, etc. Anionic surfactant, polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether,
Examples include nonionic surfactants such as polyoxyethylene polyoxybrobylene block copolymer sorbitan fatty acid ester and polyoxysorbitan fatty acid ester. Formulation adjuvants include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethylcellulose), PAP (isobrobyl acid phosphate), and the like.

Examples of formulations are shown below. The compounds of the present invention are indicated by compound numbers in Table 1. Parts indicate parts by weight.

Formulation example! Compound 4 of the present invention, 10 parts, 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.

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 agents, 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 0.01g to 100g per are.
Preferably, it is 0.1 g to 50 g, and emulsions, hydrating agents,
Suspension agents, etc. should be diluted with 1 liter to 10 liters of water per area (if necessary, a spreading agent such as a spreading agent may be added) and applied; granules, powders, etc. should be applied without any dilution. Apply as is.

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 effective 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 The chemical damage to crops and herbicidal efficacy against weeds are determined by measuring the dry weight of the above-ground parts of the test plants that remained withered at the time of the survey, and calculating the ratio (%) to the case where no compound was tested. Evaluate according to the categories in the table, and indicate the chemical damage and herbicidal efficacy as numbers from 0 to 5.

'J$3 Table Test Example 1 Field soil stem and leaf treatment test A vat with an area of 33 x 23 al and a depth of 10 m was filled with field soil, and soybean, Japanese morning glory, Japanese radish, Japanese Physalis, Japanese fir tree, and American hornwort were sown and grown for 18 days.

Thereafter, the emulsion of the test compound was diluted with water containing a spreading agent in an amount equivalent to 10 liters per are, and the sample was uniformly sprayed from above the plant over the entire stem and leaves using a small sprayer. At this time, the growth of each plant differed by 1 gil, but it was at the 2-4 leaf stage and the plant height was 2-12 cm. 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.

Table 4 Test Example 2 Upland Soil Mixture Treatment Test A cylindrical plastic pot with a diameter of 10 cx and a depth of 10 cm was filled with upland soil,
Seed #I of Ichibi and cover with soil. The test compound made into an emulsion was diluted with water equivalent to 10 liters per area, and a predetermined amount of it was sprayed on the soil surface with a small sprayer, and then sprayed at a depth of 4e+.
The soil surface layer up to n was thoroughly mixed.

After spraying, they were grown in a greenhouse for 20 days and their herbicidal efficacy was investigated. The results are shown in Table 5.

Table 5 Test Example 3 Paddy Soil Treatment Test A round crocodile-shaped plastic pot with a diameter of 8 cm and a depth of 12 cm is filled with paddy soil, and seeds of Japanese millet and broad-leaved weeds (Azaena, Kikashigusa, Chickweed) are mixed to a depth of 1 to 2 ann. It was crowded. After flooding the fields to create a paddy field, 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 made into an emulsion was diluted with 5 ml of water per pot, and a predetermined amount of it 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 6.

Table 6

Claims (2)

[Claims] (1) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents a lower alkoxy group, a lower alkylthio group, or a cycloalkyloxy group, and X represents a chlorine atom or a bromine atom. ) An N-phenyltetrahydrophthalimide derivative represented by: (2) General formula▲ Numerical formula, chemical formula, table, etc.▼ [In the formula, R_1 represents a lower alkoxy group, a lower alkylthio group, or a cycloalkyloxy group, and X represents a chlorine atom or a bromine atom. ) A herbicide characterized by containing an N-phenyltetrahydrophthalimide derivative represented by the following as an active ingredient.