JPS5976045A - Alpha,alpha-dimethylphenylacetic acid anilide derivative, its preparation and herbicide containing the same - Google Patents

Abstract

NEW MATERIAL:The compound of formula I (Y is methyl or Cl; X is halogen, lower alkyl or lower alkoxy; n is 0-2). EXAMPLE:alpha,alpha-Dimethyl-p-methylphenylacetic acid m-ethylanilide. USE:A herbicide having excellent inter-genus selectivity to gramineous plants by the treatment in the presprouting or the growing stage, absolutely harmless to rice plant, and exhibiting strong herbicidal activity to cockspur-grass. PROCESS:The compound of formula I can be prepared by reacting the alpha,alpha-dimethylphenylacetic acid derivative of formula II or its reactive derivative with the aniline derivative of formula III preferably in a solvent (e.g. benzene) in the presence of a reaction assistant (e.g. phosphorus pentachloride) at a temperature between 0 deg.C and the refluxing temperature of the solvent, preferably at 20-40 deg.C.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention is based on the general formula (where Y is a methyl group or a chlorine atom, X is a halogen atom,
A novel α, α-dimethylphenylacetic acid anilide represented by a lower alkyl group or a lower alkoxy group, n is an integer of 0 to 2, and when n is 2, the individual Xs may be the same or different. This invention relates to a method for producing a derivative and a herbicide containing it as an active ingredient.

Many phenylacetic acid anilide derivatives have been known. For example, Chemical Abstracts Volume 85 (1976
) 62766t describes a research report on the plant physiological damage activity of a group of phenyl acetic acid anilide derivatives, ie, hydroatrobic acid anilide, in which the α-carbon atom is monosubstituted with a methyl group. Also, Chemical Abstracts Volume 48 (195
4) No. 8193b reports that α,α-dimethylphenylacetic acid anilide is produced from inglovir non-enylacetic acid phenoxyoxime. However, there have been no reports on phenylacetic acid anilide derivatives in which the α-carbon atom is di-substituted with a methyl group and their biological activities.

The present inventors have previously discovered that α,α-dimethylphenylacetic acid anilide derivatives have herbicidal activity (see Japanese Patent Application No. 56-29319). Subsequently, as a result of further research, we discovered and produced a new α,α-dimethylphenylacetic acid anilide derivative (1), and found that this compound did not cause any phytotoxicity to useful crops in paddy rice cultivation areas. It has strong herbicidal and growth-inhibiting effects against competing weeds, has a slow but excellent residual effect, and has no risk of environmental pollution, and is 4- effective against humans, livestock, and fish. It was discovered that it has various excellent properties such as low toxicity.

The compound of formula (2) has excellent selectivity against rice plants in pre-emergence and growing season treatments, and is completely harmless to rice plants, while exhibiting strong herbicidal activity against grasshoppers. It also exhibits excellent herbicidal and growth-inhibiting effects on weeds of the Cyperaceae family, such as Cyperus japonica and Cyperus japonica. Therefore, the present invention further provides a herbicide containing the compound of formula (1) as an active ingredient.

Compounds of formula I are represented by the general formula: α,α-
It can be produced by reacting a dimethylphenylacetic acid derivative or a reactive derivative thereof with an aniline derivative represented by the general formula (in the formula or having the above meaning).

This reaction is preferably carried out in a solvent in the presence of a suitable reaction aid. Examples of solvents include aromatic hydrocarbons such as benzene, toluene, and xylene, ethers such as diethyl ether, tetrahydrofuran, and dioxane, alcohols such as methanol and ethanol, ketones such as acetone and methyl ethyl ketone, methylene chloride, chloroform, and tetrahydrofuran. Hydrogenated hydrocarbons such as carbon chloride are used. Examples of reaction aids used include phosphorus pentachloride, phosphorus trichloride, thionyl chloride, sodium hydroxide, potassium hydroxide, sodium bicarbonate, triethylamine, pyridine, tripropylamine, N,N-dimethylaniline, and the like.

In the reaction, it is advantageous to use equimolar proportions of the compounds of formula I and formula (2). The reaction temperature is 0°C to the reflux temperature of the solvent, preferably 20 to 40°C, and 5 reactions are 1
Finishes in ~3 hours.

The compound of formula (■) can be isolated and purified by recrystallization, vacuum distillation, etc. As a solvent for recrystallization,
For example, benzene, toluene, methyl alcohol, ethyl alcohol, chloroform, n-hexane, ethyl acetate, etc. are used.

Although the herbicide of the present invention may be used as a compound of formula I, it is usually mixed with an inert solid or liquid carrier, and optionally with the aid of an adjuvant, for example, in a conventional manner such as a wettable powder, emulsion, etc.
It is used in formulations such as granules, powders, etc. Other suitable additives, fertilizers, agricultural chemicals 2, such as herbicides, insecticides, fungicides, etc. may be added.

Solid carriers include, for example, clay, talc, kaolin, bentonite, diatomaceous earth, calcium carbonate, etc., or mixtures thereof; liquid carriers include, for example, evabenzene, xylene,
Examples include kerosene, alcohol, dimethylformamide, etc. or mixtures thereof. Also, drug dispersion, suspension,
Auxiliary agents for improving properties such as wetting, emulsification, adhesion, and fixation include surfactants such as sodium lauryl sulfate, alkyldimethylbenzylammonium chloride, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, and alkyldimethyl. High molecular compounds such as polyvinyl alcohol, such as betaine,
Sodium alginate etc. are used.

The above formulations generally contain 0.5 to 95% active ingredient by weight.
, preferably in a proportion of 1 to 90%. The content of the active ingredient varies depending on the dosage form, but for example, it is 1 to 15% in the case of granules, 10 to 80% in the case of wettable powders, 1 to 15% in the case of powders, and 1 to 15% in the case of emulsions. In some cases, 1 to 50% is preferable.

The amount of the herbicide of the present invention to be used depends on the dosage form, weather conditions, timing of use,
The amount of active ingredient per are is usually 0.5 to 50 g, preferably 1 to 30.9 g, although it varies depending on soil conditions and the type of target weed.

Synthesis example 1 Benzene S in a 100 ml four-loop flask.

Add 2.02 g of me1 triethylamine and 2.219 g of Iη-ethylaniline, cool and stir in water, then add α,
α-dimethyl-p-methylphenylacetic acid chloride 3.
549 slowly. After the addition is complete, attach a water pipe to the flask and stir overnight at room temperature. After the reaction is completed, the reaction solution is washed with water to remove triethylamine hydrochloride, the benzene layer is dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure. When the obtained device is recrystallized from n-hexane, α,α-dimethyl-p-methylphenylacetic acid-m-
4.01 g of ethylanilide is obtained (compound number 23
).

Melting point 90-91°C IR value νmaxCfrL-': 3300 (NH)
, 1650 (C=O) elemental analysis value: C,9H23O
CHN as N Calculated value (%) 81.10 8,24 4.98 Actual value (%) 81.07 8.28 4.97 Synthesis example 2 In a 100-me four-loop flask, 5 benzene 1.
Add 1 g of α,α-dimethyl-m-chlorophenylacetic acid chloride and stir at room temperature.2. 1 7
Drop 9. After the addition is complete, the mixture is stirred at room temperature for 5 hours. After the reaction is completed, the reaction solution is washed with water to remove triethylamine hydrochloride, and the benzene layer is dried over anhydrous sulfuric acid (IJ) and the solvent is distilled off under reduced pressure. When the obtained device is recrystallized from n-hexane, α,α-dimethyl-m-chlorophenylacetic acid-m-methoxyanilide 2.
37 g are obtained (compound no. 46).

Melting point 795-81°G IR value νmax 2”: 3 3 7 0 (N-H
), 1665 (C-O) elemental analysis value” Cl7HI80
CH N as 2NC1
C1 calculated value (%) 67, 21 5.97
4.61 11.67 Actual value (%J 67, 1
3 5.95 4.63 11.69 Examples of compounds obtained in the same manner are shown in Table 1.

No. 1 Formulation Example 1 Compound of the present invention (A 27 ) 6 parts Isopropyl phosphate 1 part Clay
66 parts talc
30 parts of the above ingredients are ground and mixed to obtain 100 parts of a powder.

Formulation Example 2 Compound of the present invention (Platform 3) 5 parts bentonite 2o parts sodium dodecylbenzenesulfonate 2 parts clay
76 parts of the above ingredients are pulverized and mixed, an appropriate amount of water is added and kneaded, granulated using a granulator, and dried to obtain 100 parts of granules.

Formulation example 3 bentonite 2o parts clay
77 parts lignin sulfonate 3 parts The above phase components are pulverized and mixed, water is added and kneaded, and then granulated and dried to produce granules containing no active ingredient.

95 parts of the granules are impregnated with 5 parts of the compound of the present invention (Alo) to obtain 100 parts of granules.

Formulation Example 4 Compound of the present invention (A 46 ) 50 parts Polyvinyl alcohol 2 parts Sodium dodecylbenzenesulfonate 6 parts Diatom ±
45 parts of the above ingredients are mixed and ground to obtain 100 parts of a wettable powder.

Formulation Example 5 Compound of the present invention (A 23 ) 30 parts Polyoxyethylene alkylaryl 10 parts Etherxylene 60 parts The above components are mixed and dissolved to obtain 10 parts of an emulsion.

Test Example 115 O o o Earl's pot was filled with paddy soil, two-leaf stage paddy rice was transplanted, seeds of Japanese wildflower, Japanese cypress, and bulrush were sown, tubers of Japanese cypress were planted, and the pot was flooded to a depth of 3 cm. did. On the fourth day after the germination of weeds, flooded soil was treated with a predetermined amount of the wettable powder produced according to Formulation Example 4.

Three weeks after the chemical treatment, the herbicidal efficacy and degree of chemical damage were observed for the paddy rice and each weed. The results are shown in Table 2.

The criteria for the degree of chemical damage to rice were as follows.

-2 Harmless +: Minor harm ±: Slight damage 廿: Moderate damage +++: Severe damage Applicant: Yasu Chemical Industry Co., Ltd. Agent Masao Hayashi Patent attorney

Claims (1)

[Claims] 1. General formula (wherein Y is a methyl group or a chlorine atom, X is a halogen atom,
an α,α-dimethylphenylacetic acid anilide derivative represented by a lower alkyl group or a lower alkoxy group, n is an integer of 0 to 2, and when n is 2, it may be individual or the same or different. 2. An α,α-dimethylphenylacetic acid derivative or a reactive derivative thereof represented by the general formula (wherein Y represents a methyl group or a chlorine atom) an alkoxy group, n represents an integer from D to 2, and when n is 2, the individual Xs may be the same or different). Y, X and n have the above-mentioned meanings). 6. General formula (in the formula, Y is a methyl group or a halogen atom, X is a halogen atom, a lower alkyl group or a lower alkoxy group, n is 0 to 2
, and when n is 2, the individual Xs may be the same or different).