JPS6023105B2 - α,α-dimethylphenylacetic acid anilide derivative, its production method and herbicide containing the same - Google Patents

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 Q.Q-dimethylphenylacetic acid anilide derivative represented by a lower alkyl group or a lower alkoxy group, n represents an integer of 0 to 2, and when n is 2, the individual Xs may be the same or different. , its production method, and a herbicide containing it as an active ingredient.

Many phenylacetic acid anilide derivatives have been known.

For example, Chemical Abstracts Vol. 85 (1976) 6
Clause 276 describes a research report on the plant physiologically damaging activity of a group of phenylacetic acid anilide derivatives, ie hydroatropic acid anilide, in which the Q-carbon atom is monosubstituted with a methyl group. Also chemical abstract 4
Volume 8 (1954) 819, by Isof. . It has been reported that Q.Q-dimethylphenylacetic acid anilide is produced from pyrphenylacetic acid phenoxyoxime. However, there have been no reports on phenylacetic anide derivatives in which the Q-carbon atom is di-substituted with a methyl group and their biological activities. The present inventors have previously discovered that Q.Q-dimethylphenylacetic acid anilide conductor has herbicidal activity (see Samurai Publication No. 57-144203).

After that, as a result of further research, we created a new Q.Q-dimethylphenylacetic acid anilide conductor [1'], and found that this compound did not cause any phytotoxicity to useful cultivated crops in paddy rice fields.
It has a strong herbicidal and growth effect against weeds that compete with this, has a slow but excellent residual effect, and has no risk of environmental pollution and has low toxicity to humans, livestock, and fish. It has been found that it has various excellent properties such as: The compound of formula 1 has excellent intergeneric selectivity against plants of the family Poaceae in pre-emergence and early-emergence treatments, and is completely harmless to rice, while exhibiting a strong herbicidal effect on nopye. It also exhibits excellent herbicidal and growth-inhibiting effects on weeds of the Cyperaceae family, such as Cyperaceae and Cyperaceae. Accordingly, the present invention further relates to a herbicide containing a compound of formula 1 as an active ingredient. The compound of formula 1 is a Q.Q-dimethylphenylacetic acid derivative or a reactive derivative thereof represented by the general formula (wherein Y has the above meaning), or a reactive derivative thereof, represented by the general formula (wherein Y has the above meaning) It can be produced by reacting with an aniline derivative represented by:

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 ethyl alcohol, ketones such as acetone and methyl ethyl ketone, methylene chloride, Halogenated hydrocarbons such as chloroform and carbon tetrachloride are used.
Examples of reaction aids that can be used include phosphorus pentachloride, trichloride, thionyl chloride, sodium hydroxide, potassium hydroxide, sodium bicarbonate, triethylamine, pyridine, tripropylamine, and N.N-dimethylaniline. In the reaction, it is advantageous to use equimolar amounts of the compounds of formula 0 and m. The reaction temperature is 0.000 to reflux temperature of the solvent, preferably 20 to 40°C, and the reaction is
．． Finishes in 5 to 1q lifespan. The compound of formula 1 can be isolated and purified by recrystallization, vacuum distillation, and the like.

Examples of solvents used for recrystallization include benzene, toluene, methyl alcohol, ethyl alcohol, chloroform, n-hexane, and ethyl acetate. The herbicide of the present invention may be prepared by using the compound of formula 1 as it is, but it is usually mixed with an inert solid or liquid carrier, and optionally using an auxiliary agent, for example, in the form of a wettable powder, emulsion, or granule. ,
It is used in formulations such as powders. Other appropriate additives, fertilizers, agricultural chemicals such as herbicides, insecticides, fungicides, etc. may be added. Examples of solid carriers include clay, talc, kaolin, bennite, diatoms, calcium carbonate, etc., or mixtures thereof; examples of liquid carriers include benzene, xylene, kerosene, alcohol, dimethylformamide, etc., or mixtures thereof.

In addition, surfactants such as sodium lauryl sulfate, alkyldimethylbenzylammonium chloride, polyoxyethylene alkylaryl ether, , polyoxyethylene fatty acid ester, alkyl dimethyl betaine, etc., polymer compounds such as polyvinyl alcohol, sodium alginate, etc. are used. The above formulations generally contain the active ingredients in a weight ratio of 0.
It is contained in a proportion of 5 to 95%, preferably 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, and 10 to 800% in the case of wettable powders.
0, 1-15% for powders, and 1 for emulsions.
~50% is preferred. The amount of the herbicide of the present invention to be used depends on the dosage form,
It varies depending on weather conditions, time of use, soil conditions, type of target weed, etc., but usually 0 as the active ingredient per 1 are.
．． 5 to 50 evenings, preferably 1 to 30 evenings.

Synthesis Example: In a 1100' four-bottle flask, add 5 benzene.
0', 2.02 hours of triethylamine and 2.21 hours of m-ethylaniline were added, and while cooling in water, Q.
Q-dimethyl-p-methylphenylacetic acid chloride 3.
Slowly drip Kiyu.

After completing the dripping, attach a dehydration tube to the flask and leave it 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. The obtained residue is n
- Recrystallization from hexane gives 4.01 units of Q.Q-dimethyl-p-methylphenylacetic acid-m-ethylanilide (Compound No. 23). Melting point 90-9100I
R-value gain &-1:3300 (NH), 1650 (C
=○) Elemental analysis value: C, CHN as Niji 230N Calculated value (%) 81.108.244. Actual job value (%)
81.078.284.97 Synthesis Example In a 2100 Z four-neck flask, 50 parts of benzene, 1 part of m-anisidine
．． Add 1.11 g of triethylamine and 1.11 g of triethylamine, and dropwise add 2.17 g of Q.Q-dimethyl-m-chlorophenylacetic acid chloride while stirring at room temperature.

After the addition is complete, the mixture is kept at room temperature for 5 hours. 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 removed under reduced pressure. The obtained residue is recrystallized from n-hexane to obtain 2.37 g of Q.Q-dimethyl-m-chlorophenylacetic acid-m-methoxyanilide (Compound No. 43). Melting point 79.5-8100 1R value Obi Mai-1:3370 (NH), 1665 (
C=0) Elemental analysis value: C, 7 days, C as 802NCI
Day N CI calculated value (%) 67.215.97
4.6111.67 Actual value (%) 67.135.95
4.6311.69 Examples of compounds obtained in the same manner are shown in Table 1.

Table 1 Formulation Example 1 Compound of the present invention (No. 27) 3 parts isopropyl phosphate 1 part clay
66 part talc
3. The above ingredients are ground and mixed to obtain 10 powder powders.

Formulation example 2 Compound of the present invention (No. 3)
Part 5 Pentonite
2 parts sodium dodecylbenzenesulfonate 2 parts clay? 3 parts of the above ingredients are ground 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 Pennite 2 parts Clay 77 parts Lignosulfonate 3 parts The above ingredients are pulverized and mixed, water-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 (No. 10) to obtain 10 parts of granules. Formulation example 4 Compound of the present invention (No. 46) 5 parts polyvinyl alcohol 2 parts sodium dodecylbenzenesulfonate 3 parts diatom
45 parts of the above ingredients are mixed;
Crush it to obtain 10 hydrating powders.

Formulation Example 5 Compound of the Invention (No. 23) 3 Base: Polyoxyethylene alkylaryl ether 10 parts Xylene 6 Base The above components were mixed and dissolved to obtain 10 parts of an emulsion.

Test Example Fill a pot of 1/5000 are with rice paddy ± rice, transplant 2nd season paddy rice, sow Nobye, Tamagaya 1'' and Hotaru seeds, plant Mizugajari tubers, and make the water depth 3 skins. It was filled with water.

On the fourth day after the germination of weeds, a predetermined amount of the wettable powder produced according to the formulation example was applied to flooded soil. 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. −: Harmless shi: 100 million small harm 10: 小書 佀中筈 川: Jinsho Table 2

Claims (1)

[Claims] 1 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, 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, the individual Xs may be the same or different. 2 General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, Y represents a methyl group or a chlorine atom) , tables, etc. ▼ (In the formula, There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼(in the formula, Y, X and n
has the above-mentioned meaning). 3 General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, Y is a methyl group or halogen atom, X is a halogen atom, lower alkyl group or lower alkoxy group, n is 0 to 2
(where n is 2, the individual Xs may be the same or different); agent.