JPS5931761A - Phenoxypyridine compound and herbicide containing the same - Google Patents

Abstract

NEW MATERIAL:The phenoxypyridine compound of formula I (X is halogen, cyano, alkyl, amino, OH, 2-chloro-4-trifluoromethylphenoxy, or alkoxy). EXAMPLE:2-Chloro-3-nitro-6-(2-chloro-4-trifluoromethylphenoxy)pyridine. USE:Herbicide exhibiting excellent effect for the control of noxious weeds such as Deccan grass, galingale, toothcup, bulrush, etc. of paddy field and cocklebur, black nightshade, polygonum, large carb-grass, etc. of plowed land without damaging the crops such as rice, corn, soybean, wheat, etc. PROCESS:The compound of formula I can be prepared by reacting 2-chloro-4- trifluoromethylphenol of formula II with the nitropyridine halide of formula III(Y is halogen) in an aprotic polar solvent in the presence of an alkaline substance such as K2CO3 at 0-100 deg.C for 0.1-24hr.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a phenoxypyridine compound 11 and a herbicide containing the compound as an active ingredient.

Specifically, the present invention relates to a phenoxypyridine system represented by the general formula (wherein X is a halogen atom, a cyano group, an alkyl group, an amino group, a hydroxyl group, a 2-chloro-4-trifluoromethylphenoxy group, or an alkoxy group) Compounds and herbicides containing them as active ingredients.

The halogen atom represented by X in the above general formula is
Examples include fluorine, chlorine, bromine, and iodine, and examples of the alkyl moiety of the furkyl group and alkoxy group include methyl, ethyl, propyl, butyl, and the like.

The compound of the present invention can be produced, for example, by the method described below.

2- In the formula, X is as described above, and Y is a halogen atom, that is, a chlorine atom, a bromine atom, or a iodine atom, although a chlorine atom r- is industrially preferable. The alkaline substances used include alkali metal hydroxides, carbonates, and tertiary amines, including thorium hydroxide, potassium hydroxide, thorium carbonate, potassium carbonate, and triethylamine. are added to the reaction system as they are or as an aqueous solution.

The amount used is usually 1.0 to 1 mole of halogenated nitroviridine per month! '+, l) Mono 1, preferably 1.
It is 0 to 2.0 moles. In addition, as a solvent, it is preferable to use an aprotic polar solvent, such as dimethylformamide, dimethyl sulfoxide, dimethylacetamide, N
-Methylpyrrolidone, hexamethylphosphoramide, sulfolane and the like. The amount used is usually 1 to 1 mρ per 1 mρ of halogenated nitropyridine. i0mρ,
Desirably, it is 3..1() mρ.

This reaction involves halogenated 10-birinone and 2-chloro-
It is common to use approximately equimolar amounts of 4=triple olomethylphenol, which is desirable from an industrial perspective.

The compound obtained by the above method can be further converted into the compound of the present invention by a conventional method if necessary.

Synthesis Example 12-Amino-3-nitro-6-(2-ditro-
Synthesis of 4-trifluoromethyl(1/xy)pyridine 2
-Chloro-4-trifluoromethylphenol 12.5
g.

2-ami7-3-nitro-6-chloropyridine 10. O
g, 0.5 g of potassium carbonate i, and 200+ nQ of dimethyl sulfoxide were charged into a flask, and reacted at 30° C. with stirring overnight.

After the reaction was completed, the product was poured into water and extracted with methylene chloride. Next, the extracted layer was washed with water and dried, and methane chloride was distilled off under reduced pressure to obtain the desired product 14.7 with a melting point of 80-84°C.
I got g.

Synthesis Example 2 Synthesis of 2-hydroxy-3-nitro-6-(2-chloro-4-trifluoromethylphenoxy)pyridine 2-Amino-3-nitro-6-(obtained in Synthesis Example 1 above)
2-chloro-4-trifluoromethylphenoxy)pyridine 14. , Og were poured into concentrated sulfuric acid and heated at 60°
It was heated to C. After that, it was left to cool, and further water-cooled to 0-10°C, and 4.6 g of sodium nitrite and 14 m of water were mixed with stirring.
(! Which aqueous solution was gradually added dropwise to react. After the reaction was completed, the product was poured into water and subjected to the same purification treatment as in Synthesis Example 1 to obtain 10.3 g of the target product with a melting point of 87-93°C. Obtained.

4- Synthesis Example j (Synthesis of 2-chloro-3-nitro-6-(2-chloro-4-trifluoromethylphenoxy)pyridine) 2-hydroxy-3-nitro-6 obtained in Example 2 -(2-chloro-4-trifluoromethylphenoxy)pyridine 5.0□, thionyl chloride 3.55g and dimethylbormamide 0.2m were charged into a flask,
The reaction was allowed to proceed at 80°C for 4 hours with stirring. After the reaction was completed, the product was poured into water and subjected to the same purification treatment as in Synthesis Example 1 to obtain the desired product 2.64bis with a melting point of 53 to 59°C.

Specific examples of the compounds of the present invention produced according to the general production method and synthetic example described above will be described.

51 The compounds of the present invention exhibit excellent effects in controlling noxious weeds. For example, in paddy fields, it effectively controls harmful weeds such as barnyard grass, cyperus japonica, cyperus japonica, cyperus japonica, water cyperus, and other crops without causing any substantial harm to crops such as rice, and in upland fields such as soybeans, corn, wheat, etc. without causing substantial harm to the crops of
It is effective in controlling noxious weeds such as knotweed, crabgrass, Japanese barnyard grass, and blueberry.

The herbicide containing the compound of the present invention as an active ingredient can be used in a wide variety of areas, including rice fields, fields, orchards, mulberry orchards, forests, farm roads, grounds, etc., and can be applied by either soil treatment or foliage treatment. You can also select as appropriate.

=6- The compound of the present invention (can be sprayed as is, but usually,
Emulsions, liquids, etc. can be prepared by mixing carriers and various auxiliaries as necessary.
It is used in formulations such as wettable powders, powders, and granules. The blending ratio at the time of formulation is, for example, 1 to 90% of the active ingredient, preferably 1 to 7%, and 5 to 99% of the phase or solvent.
% by weight, preferably 25-99% by weight, 0 surfactant
A suitable content is 30% by weight, preferably 1 to 20% by weight.

The compound of the present invention may exhibit even better effects depending on whether it is used or used in combination with pesticides such as HV removers, insecticides, and fungicides for ponds, or with fertilizers and soil. .

Furthermore, the appropriate amount of the herbicide of the present invention to be applied cannot be further defined due to weather conditions, soil conditions, drug formulation, application timing, application method, type of target weed, etc., but in general, the amount of active ingredient to be applied per area is 1. ~1oog, preferably 2~
It is 60g.

Next, examples of plant tests and formulations of the herbicide according to the present invention will be described.

Test Example 1 Paddy soil was poured into a 115,000-acre pot and saturated with water, then seeds of wild grass and firefly were sown, and various miscellaneous seeds were germinated in a greenhouse. Invention 7 - The compound was added dropwise so as to be 20 g per are.

20 days after treatment, the degree of growth inhibition was observed with the naked eye, and 1 to 5
The results are shown in Table 2. The results are shown in Table 2. Ta. Comparative compounds were also tested in the same manner, and the results shown in Table 2 were obtained.

Table 2 Test Example 2 Soil was placed in a 1/5,000 are pot in a greenhouse to prepare a field, and soybean, corn, rice, and various weed seeds were sown. The next day, the compound of the present invention was sprayed in a predetermined amount, and on the 25th day after the treatment, the degree of growth inhibition was observed with the naked eye.

8- (3) 5 parts by weight of sodium ligninsulfonate and each component of L were mixed and granulated, and 7 parts by weight of compound No. 5 of the present invention diluted with an appropriate amount of acetone was sprayed onto this to obtain granules. Ta.

Formulation Example 2 (1) Norcrite 78 parts by weight (2) Labelin S (trade name: Kyushu Kogyo Seiyaku Hashiba) 2
〃(3) Tsurupol Fi (139 (product name: manufactured by Toho Chemical Industries) 5 〃 (4) Carplex (product name: manufactured by Shionogi & Co., Ltd.) 15
Hereinafter, a hydrating agent was obtained by mixing a mixture of each of the components in (g) with Compound No. 3 of the present invention in a weight ratio of 4:1.

Formulation Example 3 (1) Compound No. 4 of the present invention 20 parts by weight (2) Xylene 60
(3) Tsurupol 2806B (trade name: Ni-Toho Chemical Industry Co., Ltd.) 20 The above components were mixed and dissolved to obtain an emulsion.

Patent applicant: Ishihara Sangyo Co., Ltd. 111 completed-

Claims (1)

[Scope of Claims] A heptadoxypyridine system represented by (in the formula or a halogen atom, a cyano group, an alkyl group, an amino group, a hydroxyl group, a 2-rihyro-4-trifluoromethylphenoxy group, or an alkoxy group) Compound. (in the formula or halogen atom, Schiff) group, alkyl group, ami7 group, hydroxyl group, 2-chloro-4-trifluoromethyl7
A herbicide characterized by containing a phenoxypyridine compound represented by the following formula (e7xy group or alkoxy group) as an active ingredient. 1-