JPS58216177A - Phenylthiadiazolidinedione derivative, its preparation and herbicide containing said compound as active constituent - Google Patents

Abstract

NEW MATERIAL:A compound of formula I (R is methyl, ethyl or cyclopropyl; n is 1 or 2). EXAMPLE:2-(2',5'-Difluorophenyl)-4-methyl-thiadiazolidine-3,5-dione. USE:A herbicide, capable of exhibiting herbicidal efficacy in either one of the foliar or soil treatment, and sufficient efficacy against weeds in question, e.g. Sida spinosa L., Indian mallow, morning glory, etc. in fields of cotton or corn, lower spear grass, fat hen, chickweed, etc. in fields of wheat, etc. PROCESS:A fluorophenylurea derivative of formula II is reacted with chlorocarbonylsulfenyl chloride in an inert solvent, e.g. hexane or methylene chloride, at 50-80 deg.C to give the aimed compound of formula I .

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a compound of the general formula (I) [wherein R represents a methyl group, an ethyl group, or a cyclopropyl group, and n represents/or a cyclopropyl group. ] The present invention relates to a phenylthiadiazolidinedione derivative represented by the following, a method for producing the same, and a herbicide containing the same as an active ingredient.

Certain 7-enylthiadiazolidine dione derivatives (L example ld'1.!-(,,?, a-dichlorophenyl)-termethylthiadiazolidine-3,s-dione,
J-(,?-chloro-44-trifluoromethylphenyl)-termethylthiadiazolidine-3,S-dione 1
．． The usefulness of 2-(<<-chlorophenyl)-9-methylthiadiazolidine-3,s-sion as an active ingredient in herbicides has been reported in Japanese Patent Publication Sho'I! ; -/, No. 229/ and Japanese Patent Publication No. 4Ij-, No. 20//9. However, these compounds are not always sufficient as active ingredients in herbicides.

The compound of the present invention has a herbicidal effect against a variety of problematic weeds in both foliage and soil treatments, and it also has a herbicidal effect on major crops as well as problem weeds in sorghum fields, such as American goldenrod, common weed, It has sufficient weeding effect against morning glory, morning glory, dogweed, and problem weeds in wheat fields such as sycamore, white ν, chickweed, chamomile, etc., and is also a problem for each crop. Do not show such drug damage.

The compound of the present invention has the general formula (II) [wherein R and n represent the same childish taste as described above]. ] (3) The phenylurea derivative shown in (3) and chlorocarbonylsulfenyl chloride are mixed in an inert solvent, for example, hydrocarbons such as hexane, benzene, toluene, etc., chlorine such as methylene chloride, chloroform, ethylene dichloride, chlorobenzene, etc. In a solvent such as hydrogenated hydrocarbons, tetrahydrofuran, acetonitrile, etc., s o ? :'-♂It can be produced by reacting with OC.

That is, to a solution or suspension of the heptanyl urea derivative of the general formula (If) is added an equivalent to a slightly excessive amount of chlorocarbonylsulfenyl chloride in terms of 5oc-, roc,
Keep at 0C until the generation of hydrogen chloride gas stops. Next, the solvent is distilled off, and if necessary, the product is purified by column chromatography.

Next, a manufacturing example will be shown.

Production example/[Production of compound (1) of the present invention] N-(,2',
s'-dichlorophenyl)-N'-methylurea 80
g (0,00!; 17 mol) was suspended in toluene IOC,G and kept at OC. While stirring, 7 qg (o, oo, sq mol) of chlorocarbonylsulfenyl chloride (da) was added dropwise over about 10 minutes.

After the dropwise addition, the same temperature was maintained and stirring was continued for 2 hours. Next, after cooling to room temperature, toluene and other low-boiling mixtures were distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent: chloroform). -difluorophenyl)-termethylthiadiazolidine-3,s-dione 0,3.
3 g was obtained.

m, p, zaza, yC Production Example 2 [Production of Compound (, 2) of the Present Invention] In the same manner as in Production Example/, N~(,2'-fluorophenyl) -
N'-methylurea/, Og.

Co(2'-fluorophenyl)-termethyl-thiadiazolidine-3,J-dione 0.37 g I got g.

m, p, 7co, SC Production Example 3 [Production of Compound (3) of the Present Invention] In the same manner as in Production Example/, N -(,?'-fluorophenyl) -
N'-methylurea/, Og (0,0039 mol) and chlorocarbonylsulfenyl chloride OJt g (0
J-(,?'-fluorophenyl)-termethyl-thiadiazolidine-3,
5-dione 0. II/g obtained O m, p, //3. I C Production Example [Production of Compound (Da) of the Present Invention] In the same manner as Production Example/, N-(λI, 111-difluorophenyl), /-methylurea/, 00 g (0,0
0! ;Q mole) and 0.77 g (0,00!; tamol) of chlorocarbonylsulfenyl chloride to form 2-(,2',4''-difluorophenyl)-termethyl-thiadiazolidine=3,S -Zion 0.2.2
g k get 7'C.

m, p, 9no, 4C Production Example S [Production of the compound of the present invention (→)] In the same manner as in Production Example 1, N (J-fluorophenyl) , /-cyclopropylurea/, oo g
(o, oosy mol) and chlorocarbonylsulfenyl chloride o, q, s g (c, oosy mol) to form J-(J'-fluorophenyl)-<=-cyclopropyl-thiadiazolidine-3. , S-dione o,
o7 g was obtained.

25.0 n D/,! ;Ate Production Example 2 [Production of Compound (J) of the Invention] In the same manner as in Production Example/, N -(,2'-fluorophenyl)
N/-ethyl urea i,oo g (o,oOJ!r mol) and chlorocarbonylsulfenyl chloride o,7q
g (o, ooa moles), λ-(λ'-
fluorophenyl)-+-ethyl-thiadiazolidine-
0.7 g of 3,S-dione was obtained.

24.5 nD/-j"? Table 1 shows some of the compounds of the present invention that can be produced by such a production method.

(7) Table 1: The compounds of the present invention can be formulated into emulsions, aqueous agents, suspensions, granules, powders, etc. by mixing and adding them to solid carriers, liquid carriers, surfactants, and other formulation auxiliaries. Can be used as a herbicide.

The content of the compound of the present invention as an active ingredient in the preparation is 0.1 to 90% by weight, preferably 0.1 to 90% by weight. Solid carriers include kaolin, bentonite, talc,
There are diatomaceous earth, gicrite, synthetic hydrated silicon oxide, etc.
Examples of liquid carriers include aromatic hydrocarbons such as xylene and methylnaphthalene, ketones such as cyclohexanone and isophorone, halogenated hydrocarbons such as chlorobenzene and dichloroethane, dimethylformamide, cellosolve, ethylene glycol, and water.

Surfactants used for emulsification, dispersion, spreading, etc. include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene styryl aryl ether, polyoxyethylene fatty ester, and polyoxyethylene sorbitan fatty acid. Examples include nonionic surfactants such as esters and oxyethylene oxypropylene polymers, and anionic surfactants such as alkyl sulfate ester salts, alkyl sulfonates, dialkyl sulfosuccinates, and furkylaryl sulfonates.

Salt, alginate, polyvinyl alcohol, cellulose, acidic isopropyl phosphate, BHT (,2,x-di-
t-butyluda-methyl-phenol), etc.

Examples of formulations are shown below.

Formulation example/Wettable powder: 0 parts of the compound of the present invention (1), part S of polyoxyethylene alkylaryl ether, and 7.3 parts of synthetic hydrated silicon oxide
Part 1 is thoroughly ground and mixed to obtain a wettable powder.

Formulation Example Emulsion 0 parts of the compound of the present invention (2), S part of polyoxyethylene alkylaryl ether, 5 parts of alkylaryl sulfonate, and 7 S parts of cyclohexanone are thoroughly mixed to obtain an emulsion.

Formulation Example 3 Granules 7 parts of the compound of the present invention (3), 1 part of synthetic hydrous silicon oxide, 5 parts of lignin sulfonate and 93 parts of clay were thoroughly ground and mixed, water was added and the mixture was thoroughly kneaded, followed by granulation and drying. to obtain granules.Powder: 3 parts of the compound of the present invention (5'), acidic isopropylene phosphate.

Building θ. Part 5, Kaolin Otsu 4. Part J and 3θ part of talc are thoroughly ground and mixed to obtain a powder.

The mixture was mixed with 60 parts of an aqueous solution containing 3% by weight of Rubitan monooleate, wet-milled until the particle size of the active ingredient became 3μ or less, and then mixed with 30 parts of an aqueous solution containing 3% by weight of sodium alginate as a dispersion stabilizer. A suspension is obtained by doing this.

Emulsions, irrigation agents, suspensions, etc. prepared in this way are usually diluted with water, etc. and applied as single grains, and powders, etc., are applied as is by spraying on foliage or mixing with the soil.In addition, the compounds of the present invention are used as herbicides. It can be mixed with other herbicides to enhance their efficacy, or they can be applied simultaneously without mixing, and in some cases, a synergistic effect can be expected. Furthermore, it can be used in combination with insecticides, acaricides, insecticides, fungicides, plant growth regulators, fertilizers, soil conditioners, and the like.

When the compound of the present invention is used for either foliage treatment or soil treatment, the application rate can be varied over a fairly wide range, but it is usually /y/y~〃θ1 per are, preferably -2F-4
It is 07. The amount of application depends on the type of preparation, the place of application,
The amount can be increased or decreased depending on the method, season, crop, type of weed, degree of weed damage, weather conditions, etc. without being affected by the above range.

Next, test examples will be given to show that the compounds of the present invention are useful as active ingredients of herbicides.

To determine chemical damage to crops and herbicidal efficacy against weeds, measure the fresh weight of the stems and leaves of the plants that remained withered at the time of the survey, calculate the ratio (@) to that of the untreated area, and evaluate each from θ to J according to the classification in Table 2. Shown in numerical value.

(/-) Table 1. Regarding the test compounds, the compounds of the present invention are the compound numbers in Table 1, and the comparison group I! The compounds used in the furnace are shown by compound number in Table 3.

Table 3 Test example of pre-emergence soil in a field (for high-temperature crops) Field soil was placed in a cylindrical plastic pot with a diameter of θ and a height of 70 m. Seeds of corn, cotton, American goldfish, morning glory, Japanese radish, Datura, and Japanese millet were sown.After covering the soil, a predetermined amount of the emulsion of the test compound prepared according to "Formulation Example" was diluted with water. Soil surface treatment was performed using a small sprayer.

Thereafter, the mixture was grown in a greenhouse at 25''C during the day at 3θ°C and at night, and the chemical damage to crops and herbicidal efficacy against weeds were observed on the θ day after treatment.

The results are shown in Table 9.

(/S) Table d (/B) Trial sales example Upland pre-germination soil treatment test (for low-temperature crops) Seeds of wheat, whitegrass, sycamore, and chamomile were sown in the same manner as in test example/, and after covering with soil, Dilute the specified amount of the emulsion of the test compound prepared according to Formulation Example with water,
Soil surface treatment was performed using a small sprayer. After that, they were grown in a low-temperature greenhouse at a temperature of θ6C1 during the day and θ°C at night, and after treatment,
On the 27th day, chemical damage to crops and herbicidal efficacy against weeds were observed.

The results are shown in Table 5.

Table S Test Example 3 Post-germination foliage treatment test for upland fields Field soil was packed into plastic trays measuring 36 cm (vertical), 26 cm (horizontal), and 70 m (height) to test wheat, corn, cotton, purslane, American hornwort, Japanese croaker,
Japanese radish, buckwheat, white radish, and dogberry
[L, After growing in a greenhouse for 3 weeks, two of these trays were arranged in a frame of length 50 m, width 100 cm, S height 'IOtwr, and prepared according to the formulation example - using a small sprayer from above the plants. A predetermined percentage of the emulsion of the test compound was diluted with water and sprayed on the entire surface of the frame. After being grown in a greenhouse for an additional three weeks after spraying, the phytotoxicity of the crops and herbicidal efficacy against dark blue grass were observed and evaluated.

The results are shown in Table 6.

The size of the plants at the time of spraying differed depending on the mulch, but the plant height at the leaf stage was approximately 4,000 yen.

Table 6

Claims (1)

[Claims] (1) General formula [wherein R represents a methyl group, ethyl group or cyclopropyl group, and n represents 1 or 2]. ] Phenylthiadiazolidinedione derivative (,2) general formula [wherein R represents a methyl group, an ethyl group or a cyclopropyl group, and represents n u /or 2]. [In the formula, R and n represent the same meanings as described above. ] Method for producing phenylthiadiazolidinedione derivatives represented by the following formula (3) General formula [wherein RU represents a methyl group, an ethyl group or a cyclopropyl group, and n represents/or all groups. ] It is characterized by containing a phenylthiadiazolidinedione derivative shown as an active ingredient.