JPS6133154A - Anilic acid derivative and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound expressed by formula I (R1 is lower alkyl; R2 is lower alkoxycarbonyl or lower alkoxyl). EXAMPLE:Ethyl 4'-chloro-2'-fluoro-5'-ispropoxy-1,2,3,4,5,6-hexahydrophthalanilate. USE:A herbicide useful for weeds in upland field and paddy field. PREPARATION:A 2-haloformyl-1-cyclohexanecarboxylic acid ester expressed by formula II is reacted with a 5-substituted-4-chloro-2-fluoroaniline exprssed by formula III in an inert solvent in the presence of a base, e.g. triethylamine or pyridine, at 0-100 deg.C to give the aimed compound expressed by formula I. The compound is used as herbicide in an amount of 50-1,000g, preferably 50-400g based on 10 ares.

Description

[Detailed Description of the Invention] [Industrial Application Field] The present invention relates to a novel compound, a method for producing the same, and a herbicide characterized by containing the same as an active ingredient.
More specifically, the present invention relates to ethyl hexahydrophthalanilide (hereinafter, the present compound ), its production method, and a herbicide characterized by containing one or more of them as an active ingredient.

[Conventional technology]

Although tetrahydrophthalanilide acid derivatives and herbicides containing this compound as an active ingredient are already known, hexahydrophthalanilide acid derivatives such as the compound of the present invention and herbicides containing this compound as an active ingredient are new. .

[Problem that the invention seeks to solve]

The object of the present invention is to advantageously obtain the compound in the melting industry, and furthermore to provide a herbicide that is extremely useful in upland and paddy rice cultivation.

[Means for solving problems]

The compound of the present invention is a novel compound that has not been described in any literature, and can be produced by various methods. Among the compounds of the present invention, R
An ester derivative in which 1 is an alkyl group having 1 to 4 carbon atoms can be produced, for example, by the reaction of the following formula.

t(2 (wherein, 5-4F[-
It can be produced by reacting with 4-chloro-2-fluoroaniline. Examples of the inert solvent include ethers such as ethyl ether, dioxane and tetrahydrofuran, aromatic hydrocarbons such as benzene and xylene, and ketones such as acetone methyl ether ketone.

Also, triethylamine and pyridine are used as bases.

Examples include amines such as dimethylaniline, aniline as a raw material, sodium hydroxide, potassium hydroxide, sodium carbonate, and potassium carbonate.

The reaction temperature is 0 to 100°C, preferably 10 to 50°C.

When using the compound of the present invention as a herbicide, the active ingredient must be 10A/50Y-1. OO[1i, preferably 50? ~400t is usually mixed with various auxiliaries, such as diluents,
It is used by blending solvents, surfactants, etc. into formulations such as emulsions, aqueous solutions, powders, and granules.

In addition, herbicides containing the compound of the present invention include other types of herbicides, plant growth regulators, fungicides, insecticides, nematicides, acaricides,
Synergists, attractants, repellents, pigments, fertilizers, etc. can be mixed and used.

[Function and effect]

The compounds of the present invention can effectively control weeds in upland fields by treating the soil before or at the early stage of germination, and can also be used to effectively control weeds in paddy fields before or immediately after the weeds emerge after transplantation of paddy rice takes root. It shows excellent herbicidal power when treated with soil, and can be safely used for paddy rice.

EXAMPLES Next, the present invention will be explained with reference to Examples, but the present invention is not limited to these Examples.

Example 1 Ethyl 4t-chloro-22-fluoro-51-isopropoxy-1,2,5,4,5,6-hexahydrophthalanilide (Compound 2) 1.2,3,4,5.6- 1.16F of monoethyl hexahydrophthalate was heated under reflux in 10-thionyl chloride, and excess thionyl chloride was distilled off under reduced pressure. The obtained ethyl 2-chloroformyl-1-cyclohexanecarboxylate was converted into 4-chloro-2-fluoro-
The mixture was added dropwise to an ether solution containing 1.2 t of 5-impropoxyaniline and 0.61 t of triethylamine at room temperature, and stirred for 12 hours. The reaction mixture was filtered and the solvent was distilled off. The resulting residue was subjected to column chromatography [silica gel,
The target product 1.4254 (yield: 65.5%) was obtained.

Table 1 shows representative compounds of the present invention.

Table 1 Example 2 Wettable powder 50 parts of the compound of the present invention 42 (parts mean parts by weight, the same applies hereinafter), 30 parts of diatomaceous earth, 52 parts of clay, 3 parts of sodium ligninsulfonate, Ilioxyethylene 5 parts of nonylphenol ether (pulverized by White Kagen) was ground and mixed to prepare an irrigation agent.

Example 3 Emulsion An emulsion was prepared by dissolving 20 parts of Compound 1 of the present invention, 75 parts of xylene, 3 parts of polyoxyethylene nonylphenol ether, and 2 parts of calcium dodecylbenzenesulfonate.

Example 4 Granules: 5 parts of Compound 2 of the present invention, 15 parts of bentonite, 52.5 parts of talc, 25 parts of clay, 2 parts of sodium ligninsulfonate, 0.0 parts of sodium dodecylbenzenesulfonate.
5 parts were uniformly mixed and pulverized, some water was added, the mixture was made into multi-granules using an extrusion granulator, and the mixture was dried and sieved to obtain granules.

Next, the herbicidal effects of the compounds of the present invention will be explained using test examples.

Test Example 1 Soil treatment test after sowing in a field Weed seeds of crabgrass, blueberry, and pigweed and soybean seeds were sown in clay pots, and after covering with soil, a predetermined amount of the compound of the present invention was made into an emulsion, diluted with water, and sprayed. The soil was treated at The plants were then grown in a greenhouse, and 20 days after treatment, the herbicidal efficacy and crop damage were observed. The results are shown in Table 2.

Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. However, phytotoxicity of crops was also expressed using the same criteria as herbicidal efficacy.

0...Weed suppression rate 0-9%1...
・・・・・・ l 10～29%2・・・・・・・・・
・ ＃30〜49chi5・・・・・・・・・ ＃
50-69chi 4・・・・・・・・・ I 7
0~89%5・・・・・・・・・ I 90~1
0〇-Table 2 Test Example 2 Soil treatment test in transplanted paddy rice s, oo
Fill a 1:00 Ahr Wagner pot with paddy soil, then sow 30 Novie seeds, and then transplant 1 plant (2 plants/plant) of 2-leaf stage paddy rice (variety Nihonbare) per pot.
Moreover, I love ff! Plant the tubers of Yatsuri, approx. 5c.
It was managed under m0 ice-free conditions. The emulsion of the compound of the present invention prepared in Formulation Example 2 at the early stage of the emergence of wild grass and broad-leaved weeds was diluted with a predetermined amount of water and applied uniformly to the water surface.

The herbicidal effect and chemical damage were investigated on the 25th day after the chemical treatment, and the results shown in Table 3 were obtained.

The herbicidal effect in Table 5 was evaluated using the same method as in Example 5.
Represented by the number 5.

Regarding chemical damage, the ratio of plant height, number of tillers, and all types (air-dried weight) to the untreated plot was calculated. It was evaluated on a four-point scale expressed as +10.

Table 5

Claims (2)

[Claims] (1) Hexahydrophthalanilide acid derivatives represented by the general formula ▲ Numerical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 represents a lower alkyl group, R_2 represents a lower alkoxycarbonyl group or a lower alkoxy group). (2) General formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (In the formula, R_1 represents a lower alkyl group, R_2 represents a lower alkoxycarbonyl group or a lower alkoxy group. A herbicide characterized by containing: