JPS5817441B2 - old man - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an agriculturally and horticulturally useful herbicide containing a diphenyl ether compound as an active ingredient.

Many diphenyl ether herbicidal compounds have been proposed, but the ones that have been put into practical use are, for example, 2,4-dichloro-4'-nitrodiphenyl ether and 2,4-dichloro-3'-meth). #Coo 4/
- to the extent that nitrodiphenyl ether etc. can be mentioned,
Their number is extremely limited.

The present inventors have searched for highly practical herbicidal compounds among newly synthesized compounds of this type, and as a result, the compound represented by the following general formula has been found to have suitable activity as a herbicide in various plant tests. In other words, the present invention is based on the general formula (where X is a halogen atom or a cyano group, R is a lower alkyl group, and n is 2 or 3). ) is a herbicide characterized by containing at least one type of compound represented by the following as an active ingredient.

In the above general formula, the halogen atom represented by X includes, for example, a chlorine atom, a bromine atom, a fluorine atom, and R
Examples of the lower alkyl group represented by include methyl group,
Ethyl group, n-propyl group, 1so-propyl group, n-
Examples include butyl group.

The herbicidal compound according to the present invention can be synthesized according to the usual method for synthesizing diphenyl ether compounds, but it is particularly preferable to use one of the following methods (in each of the above reaction formulas, X, R and n are and halo is a halogen atom) Typical synthesis examples of the herbicidal compound according to the present invention are described below.

Synthesis example 12-chloro-4-)IJ fluoromethyl 3/-
Synthesis of methoxyethoxyethoxy-4'-fluoromodiphenyl ether 2-chloro-
4-) IJ fluoromethyl-37-hydroxy 4'
-7" Romodiphenyl ether 36.8f caustic, /-
6.415 and water 50m/(7), and this suspension was added with methoxyethoxyethyl bromide 27,
51 was added above 50°C.

After reacting these at boiling temperature (100°C) for 5 hours with stirring, the reaction product was extracted with chloroform.

The extracted layer was washed with water, chloroform was distilled off, and then distilled under reduced pressure to obtain 35 da of the target product with a boiling point of 193-200°G/2.5M111Hf.

Synthesis VA22-chloro-4-trifluoromethyl-37
-Medoxyethoxyethoxy 4'-cyanodiphenyl ether synthesis 2-'70low 4-) IJ fluoromethyl-37-medoxyethoxyethoxy 47-cyanodiphenyl ether 17.59 in dimethylformamide (DMF 320
ml, and 3.3 f of cupric cyanide was further added thereto, followed by reaction at 150 to 155° C. for 3 hours with stirring.

The reaction product was poured into an appropriate amount of ferric chloride aqueous solution and extracted with chloroform.

The extracted layer was washed with water, chloroform was distilled off, and then distilled under reduced pressure to obtain 13 g of the target product with a boiling point of 185-1900G15Hy.
I got it.

In addition, herbicidal compounds according to the present invention other than those mentioned above, such as 2-chloro-4-)IJ fluoromethyl-3/-ethoxyethoxyethoxy-4'-7' romodiphenyl ether (
1), p, 195-203°C/3tptyttH'/
l, 2-chloro-4-trifluoromethyl-3'
iso 7'lopoxyethoxyethoxy-4/-chlorodiphenyl ether, 2-chloro-4-trifluoromethyl-37-medoxyethoxyethoxyethoxy4
'-chlorodiphenyl ether (b, p, 185-19
0°C/3 Hfl, 2-chloro-4-trifluoromethyl-37-medoxyethoxyethoxyethoxy47
-promosyphenyl ether (b, p, 203-207
°C/4ffi7ffHy)2-chloro-4-)I to y
fluoromethyl-37-methoxy toxhetoxy-4'-cyanodiphenyl ether (b, p, 193
〜198℃4tttmH da), 2-chloro-4-) I
J Fluoromethyl-3'-ethoxyethoxyethoxyethoxy-4'-cyanodiphenyl ether (b, p, 1
95-203°C 7211MH91 was also synthesized according to the above synthesis method or synthesis example, and when subjected to various plant tests, it showed excellent herbicidal activity as shown in the test examples below.

The herbicidal compound according to the present invention can be used after being dispersed in water, or can be mixed with various auxiliary agents such as diluents, solvents, emulsifiers, and spreading agents to form powders, granules, irrigation agents, solutions, and emulsions. It can be formulated and used in the following forms.

Some examples are given below.

Example 1 20 parts by weight of 2-chloro-4-)IJ fluoromethyl-3'-methoxyethoxyethoxy-47-cyanodiphenyl ether, 60 parts by weight of xylene, and 2 parts by weight of Xylene
20 parts by weight of 806B (trade name: manufactured by Toho Chemical Industries) were uniformly mixed to form an emulsion.

Example 2 12 parts by weight of 2-chloro-4-)IJ fluoromethyl-3/-methoxyethoxyethoxyethoxy-4/-cyanodiphenyl ether, 60 parts by weight of solvent naphtha, N
- 23 parts by weight of methylpyrrolidone and 5 parts by weight of surfactant Neugen EA140L (trade name: Dai-Kogyo Seiyaku Co., Ltd.) were mixed uniformly to form a liquid preparation.

Example 3 5 parts by weight of 2-chloro-4-trifluoromethyl-3'-ethoxyethoxyethoxyethoxy-4/-cyanodiphenyl ether, 90 parts by weight of bentonite and 5 parts by weight of sodium ligninsulfonate were mixed and an appropriate amount of granulation was made. The required water was added and the mixture was granulated into granules.

The herbicide of the present invention is applicable to paddy fields, fields, orchards,
There are a wide variety of applications, including mulberry orchards, mountain forests, farm roads, grounds, and factory sites, and the application method can be selected as appropriate, such as soil treatment in flood conditions and field conditions, or foliage treatment.

Although the appropriate amount of the herbicide of the present invention to be applied cannot be determined unconditionally due to differences in weather conditions, soil conditions, drug formulation, application timing, application method, type of target miscellaneous flowers, etc., it is generally determined as the amount of active ingredient applied per are. 0.5~100f preferably 2
．． It is 5-50f.

In addition to being used alone, the herbicide of the present invention can also be used in combination with other herbicides, pesticides such as insecticides, fungicides, etc., as well as with fertilizers, soil, etc., and the combination of these can provide even better effects. may be indicated.

Test Example 1 Soil was placed in a 1,710,000-acre pot, impregnated with water to a supersaturated state, and a certain amount of air-dried millet seeds were sown.
I lightly covered it with soil.

When the barnyard grass germinated on the ground surface, the pot was placed in a soil state with a water depth of 3 aR, and then the aqueous dispersion of each active ingredient was treated to make it malleable.

On the 14th day after the treatment, the surviving barnyard grasses in the pots were taken out, and then air-dried and their weights were measured.

The percentage of the amount of viable contaminants relative to the untreated area was calculated, and this was used as the growth rate to obtain the results shown in Table 1.

Table 1 Test Example 2 Soil was placed in a 1/10,000 are pot, impregnated with water to a supersaturated state, and the soil was lightly covered with soil containing a certain amount of weed seeds.

After that, it was flooded and maintained at a water depth of fa::3 (7), and on the 7th day, when the emergence of each weed was consistent, a predetermined amount of an aqueous dispersion of active ingredient (active ingredient amount 101i'/a) was added. .

On the 14th day after the chemical solution treatment, the growth state of the weeds was visually observed, and the results shown in Table 2 were obtained.

The degree of growth inhibition in the table is expressed by dividing the degree of growth inhibition obtained by visual observation into five levels according to the following criteria.

Evaluation point Growth suppression degree (Takashi 1
0~〈20 2 20~<40 3 40~<80 4 80~ku100 5 100 Table 2 Test Example 3 No.1
Soil was placed in a 73,000-area pot, and a certain amount of barnyard grass seeds were sown in a field condition, and the soil was covered with soil containing seeds of common weeds such as crabgrass, canopy, and flea weed to a thickness of about ICIn.

After sowing, an aqueous dispersion of the active ingredient was sprayed on the third white of the seed. The growth state of the weeds was visually observed 20 days after the chemical treatment, and the results shown in Table 3 were obtained.

The degree of growth inhibition in the table is expressed by dividing the degree of growth inhibition obtained by visual observation into 10 levels according to the following criteria.

Evaluation point Degree of growth inhibition (@ 1 ° 0 ~ <10 2 ° 10 ~ <25 3 ° 25 ~ <40 4 ° 40 ~ <55 5 ° 55 ~ <70 6 ° 70 ~ <85 7 ° 85 ~ <90 8 ° 90 ~ < 95 9 ° 95 ~ 100 10 ° 100 Table 3 Test Example 4 Soil was put into a 1/10,000 arm pot to prepare a field, and a certain amount of barnyard grass, radish, and soybean seeds were sown there. The area was covered with soil to the thickness of the reserve.

Thereafter, when the barnyard grass reached the two-leaf stage, an aqueous dispersion of the active ingredient at a predetermined concentration was sprayed so as to uniformly cover the stems and leaves.

After the chemical treatment, the growth conditions of the various objects were observed with the naked eye on day 1, and the degree of growth inhibition was expressed using the same criteria as in Test Example 3 to obtain the results shown in Table 4.

Claims (1)

[Claims] 1. At least one compound represented by the general formula (wherein X is a rogen atom or a 7-ano group, R is a lower alkyl group, and n is 2 or 3) A herbicide characterized by containing it as an ingredient.