JPS6029711B2 - Oxadiazole compound - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides 3-methyl-5-{1-[4-(2-chloro-
The present invention relates to a 4-trifluoromethylphenoxy)phenoxyethyl}-1,2,4-oxadiazole compound and a herbicide containing it as an active ingredient.

The present inventors conducted research with the aim of developing a herbicide that is selective between Poaceae crops and Poaceae weeds, found that the compound of the present invention was suitable for that purpose, and developed the compound. The compounds of the present invention can be used against weeds of the Poaceae family, such as Japanese grasshopper, Japanese grasshopper, hackberry grass, oat grass, Psyllium japonica, Setogaya, Japanese grasshopper, Chikarashinozu, Novie, Japanese grasshopper, as well as perennial problems such as Seiban sorghum, Japanese sorghum, and Shibagi. It has been found that it exhibits a herbicidal effect when treated with soil and hollyhock, and has the excellent feature of not causing any phytotoxicity to rice, a crop that uses the same rice material.

Of course, no chemical damage was observed in crops such as dicotyledonous soybeans, cotton, and beets. In rice cultivation, there is a desire for a herbicide that is harmless to rice seedlings transplanted and has a weed-killing effect from the beginning of emergence to the growing season, and the compounds of the present invention have been found to meet these requirements.
Ta. The compound according to the present invention completely controls rice vine at an active ingredient dose of 1 night/a, but against transplanted paddy rice at a dose of 100 days/a.
Even the well-known 3,4-dichloropropion ani IJ, which has selectivity between corn and rice in foliage treatment, causes severe chemical damage to rice at a dose of 100/a. However, the compound of the present invention has the unique property of being completely harmless and exhibiting extremely excellent intergeneric selectivity within grass family plants, which is unimaginable for conventional herbicides.

Next, a method for synthesizing the compound of the present invention will be explained.

3-methyl-5-1-(1-chloroethyl)-1,2,4-oxadiazole 2.2 hours, 2-chloro-4-trifluoromethylphenylene-4-hydroxyphenyl ether 4.3 hours and anhydrous potassium carbonate 1.1 was dissolved in 30 ml of dimethylformamide and stirred at 10,000 ml for 3 hours to react.

After the reaction was completed, the reaction mixture was poured into water above 300 ml,
The mixture was thoroughly mixed with Benzene 200 Matsukami and extracted and separated. Next, the dilute aqueous alkali solution was mixed well with water, separated, and the organic layer was taken out. After dehydration with anhydrous sodium sulfate, benzene was distilled off to obtain a liquid target product with a refractive index of No. 25: 1.5296, 4.7 I got the evening. Elemental analysis value (%) (C, 8 days.
4CIF3N203) is as follows.

C day CI F N Calculated value: 54.22 3.54 8.89 14.2
97.02 Actual value: 54.03 3.59 9.04
14.516.86 When the compound of the present invention is used as a herbicide, one or more other herbicides, agricultural chemicals such as insecticides, fungicides, and plant growth regulators, soil conditioners, or fertilizers may be used. Not only can it be used in combination with other substances, but also mixed preparations with these substances are also possible.

In the herbicide formulation of the present invention, the content of the active ingredient is 1 to 10% in granules, 20 to 40% in wettable powders, and 10 to 50% in emulsions (all weight/gc). desirable.

Next, examples of formulations of herbicides containing the compound of the present invention as an active ingredient will be shown.

In the examples, "parts" represent "parts by weight." Example 1 Granules 5 parts of the compound of the present invention, 72 parts of bentonite, 2 parts of talc, 2 parts of sodium dodecylbenzenesulfonate, and 1 part of sodium ligninsulfonate were mixed, and an appropriate amount of water was added to form a bran. The mixture was granulated in a conventional manner using an extrusion granulator to obtain 100 parts of granules.

Example 2 Wettable powder Three parts of the compound of the present invention, ±6 parts of Diatom, and one part of sodium dodecylbenzenesulfonate were mixed and ground to obtain 10 parts of a wettable powder.

Example 3 Emulsion Compound 1 of the present invention, Solpol 800A (Toho Chemical Co., Ltd.)
Emulsifier) Mix 1 Ikarito and 8 Ikarito benzene to make emulsion 1
Obtained 0 anchor countries.

Next, the excellent herbicidal effects of the compounds of the present invention will be specifically disclosed through test examples.

Test Example 1 Paddy Field Initial Weed Killing Test A/5000 Wagner pots were filled with soil, and seeds of Japanese millet, Heraomodaka, Kikashigusa, and Tamagalli were sown and flooded.

Two paddy rice plants (two-leaf stage) that had been grown in advance were used as one plant, and the two plants were transplanted and grown in a greenhouse. Five days after transplanting paddy rice, at the beginning of weed emergence, a predetermined amount of the compound of the present invention was submerged in water using a granule prepared according to the method described in Example 1 above. One month after the treatment, weed growth and chemical damage to paddy rice were investigated, and the results shown in Table 1 were obtained. The display method in this table is based on the following standards. Evaluation criteria: Survival rate 0 as shown by air dry weight ratio vs. untreated area
90-100% 1 60-89% 2 30-59% 3 10-29% 4 5-9% 5 0-4% Table 1 Known Compound A: 2,4-dichloro-3'-methoxy-4'nitrodipheny 'Reetenore test example 2 Field crop weed control test by foliar treatment A/5000 Wagner pots were filled with soil, soybean, rice,
Seeds of crabgrass, foxtail grass, Japanese wildflower, Japanese grasshopper, and white grass were sown and grown in a greenhouse.

When each grass species grew to the 2-4 leaf stage, a predetermined amount of the compound of the present invention was treated with a hydrating powder prepared according to the method described in Example 2 above. An investigation was conducted 20 days after the treatment, and the results shown in Table 2 were obtained. The display method in this table is based on Test Example 1.
Table 2 Known compounds DCPA: 3,4-dichloropropionanilide

[Brief explanation of drawings]

FIG. 1 shows an infrared absorption spectrum diagram of the compound of the present invention. Figure 1

Claims (1)

[Claims] 1 3-methyl-5-{1-[4-(2-chloro-4-
trifluoromethylphenoxy)phenoxy]ethyl}
-1,2,4-oxadiazole 2 3-methyl-5-
A herbicide containing {1-[4-(2-chloro-4-trifluoromethylphenoxy)phenoxy]ethyl}-1,2,4-oxadiazole as an active ingredient.