JPH0764812B2 - Tetrahydrophthalimide derivative and herbicide containing the same as an active ingredient - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [In the formula, R represents a haloalkyl group, a haloalkenyl group or a haloalkynyl group, and X represents a chlorine atom or a bromine atom. ] The present invention relates to a tetrahydrophthalimide derivative (hereinafter referred to as the compound of the present invention) and a herbicide containing the same as an active ingredient.

Certain tetrahydrophthalimide derivatives, such as 2
-(4-chlorophenyl) -4,5,6,7-tetrahydro-2
The fact that H-isoindole-1,3-dione can be used as an active ingredient of herbicides is described in JP-B-48-11940. However, these compounds are not always sufficient as active ingredients of herbicides.

The compound of the present invention, in the foliar treatment and soil treatment of upland fields, various weeds that are problematic, for example, buckwheat vine, Sanaetade, purslane, white clover, Aogatetow, Japanese radish, Noragarashi, Nazuna, Astragalus membranaceus, Ebisugusa, Shikoku, American stag deer, Broad-leaved weeds such as field pansies, American morning glory, Malaga morning glory, Convolvulus vulgaris, White-billed Morning Glory, Pygmy puffin, Scutellaria baicalensis, Onami fir, Sunflower, dog chafer, etc. Grass weed,
It has herbicidal activity against Cyperaceae weeds such as Kogomegayatsu and the like, and the compound of the present invention does not show a serious phytotoxicity to major crops such as corn, wheat, soybean and cotton.

Further, the compound of the present invention is a variety of weeds that are problematic in the flooding treatment of paddy fields, for example, grass weeds such as Taenia japonicus, azena, yellow sedge, broad-leaved weeds such as Mizohakobe, cyperaceae weeds such as matsubai, urinary kawari etc. It has a herbicidal effect and does not show any harmful phytotoxicity to rice.

The compound of the present invention has the general formula [In the formula, X represents the same meaning as described above. ] The hydroxyphenyl tetrahydrophthalimide derivative shown by these, and general formula RY [III] [In formula, R represents the same meaning as the above, Y is a chlorine atom,
It represents a bromine atom or a substituted phenylsulfonyloxy group. ] It can manufacture by making the compound shown by these react in a solvent in the presence of a dehydrohalogenating agent at 20 ° C to 150 ° C for 1.0 hour to 48 hours.

The amount of the reagent used in this reaction is 1 equivalent of the hydroxyphenyl tetrahydrophthalimide derivative [II],
Compound [III] and the dehydrohalogenating agent are respectively
1.0 to 1.5 equivalents and 1.0 to 1.2 equivalents.

As the solvent, diisopropyl ether, dioxane,
Tetrahydrofuran, ethylene glycol, ethers such as dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, ketones such as cyclohexanone, acetonitrile, nitriles such as isobutyronitrile, formamide, N, N-dimethylformamide, N, N Examples thereof include acid amides such as dimethylacetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, and mixtures thereof.

Examples of the dehydrohalogenating agent include inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal alkoxides such as sodium methoxide and sodium ethoxide.

After completion of the reaction, the reaction solution is subjected to usual post-treatments such as organic solvent extraction and concentration, and if necessary, chromatography,
The desired compound of the present invention can be obtained by purification by operations such as distillation and recrystallization.

In the compounds of the present invention, R is the formula, ZCHFCF ₂ - in [wherein, Z represents a perfluoroalkyl group or a fluorine atom. A haloalkyl group is a compound represented by] can hydroxyphenyl tetrahydrophthalimide derivative [II], in the general formula CF ₂ = CF-Z [IV] [wherein, Z is as defined above. ] It can also manufacture by making the fluoro olefin shown by these react in a solvent in presence of a base at 10 degreeC-30 degreeC for 1 hour-96 hours.

The amount of the reagent used in this reaction is 1 equivalent of the hydroxyphenyl tetrahydrophthalimide derivative [II],
The fluoroolefins [IV] and the base are 1.
0 to large excess equivalent and 1.0 to 1.1 equivalent.

Examples of the solvent include amides such as N, N-dimethylformamide and N-methylpyrrolidone and ethers such as dioxane.

Examples of the base include sodium hydride, potassium hydride, potassium hydroxide and the like.

After completion of the reaction, the reaction solution is added with water, then subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, purified by an operation such as chromatography to obtain the target compound of the present invention. be able to.

Next, production examples of the compound of the present invention will be shown.

Production Example 1 (Production of Inventive Compound 3) 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -4,5,6,7-tetrahydro-isoindole-1,3
-3.4 g of 2-bromoethoxy p-toluenesulfonate was added to a mixed solution of 3 g of dione, 0.8 g of anhydrous potassium carbonate and 20 ml of dimethylformamide, and the mixture was stirred at 60 to 80 ° C for 3 hours. After allowing to cool, water was added and the mixture was extracted with ethyl acetate. Wash the extract with water,
Dry, concentrate under reduced pressure, and purify the residue by silica gel column chromatography (eluent = n-hexane: ethyl acetate).
2.1 g of [4-chloro-2-fluoro-5- (2-bromoethoxy) phenyl] -4,5,6,7-tetrahydro-2H-isoindole-1,3-dione were obtained. ▲ n ^19.3 _D ▼ 1.5650 Production Example 2 (Production of the present compound 8) 2- (4-chloro-2-fluoro-5-hydroxyphenyl) -4,5,6,7-tetrahydro -2H- isoindole -1 It was dissolved in 1.0 g of 3,3-dione in 20 ml of dimethylformamide and placed in a stainless steel autoclave. This is 0
After cooling to 0 ° C and adding 0.15 g of sodium hydride to stop gas evolution, the mixture was cooled to -40 ° C. To this, 5 ml of hexafluoropropene (captured by gas trap at -40 ° C or lower) was added and sealed. The mixture was left standing at 20 to 10 ° C overnight, and then stirred for 8 hours. The reaction mixture was poured into water, extracted with ether, washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel thin layer chromatography to give 2- [4-chloro-2-fluoro-5- (1,1,2,3,3,3-hexafluoropropoxy) phenyl] -4,5,6, 0.9 g of 7-tetrahydro-2H-isoindole-1,3-dione was obtained.

Table 1 shows some of the compounds of the present invention which can be produced by such a production method.

When the compound of the present invention is used as an active ingredient of a herbicide,
Usually, it is mixed with a solid carrier, a liquid carrier, a surfactant and other auxiliaries for formulation to prepare an emulsion, a wettable powder, a suspension, a granule and the like.

These formulations contain the compound of the present invention as an active ingredient in an amount of 0.1 to 90% by weight, preferably 0.3 to 80%.

Examples of the solid carrier include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, fine powder or particles of synthetic hydrous silicon oxide, and the like. As the liquid carrier, xylene, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol, cellosolve, acetone, cyclohexanone, ketones such as isophorone, soybean oil, vegetable oil such as cottonseed oil, dimethyl sulfoxide, acetonitrile. , Water, etc.

Surfactants used for emulsification, dispersion, moistening, etc. include anionic surface active agents such as alkyl sulfate ester salts, alkyl aryl sulfonates, dialkyl sulfosuccinates, and polyoxyethylene alkyl aryl ether phosphate ester salts. Agent, polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether,
Examples thereof include nonionic surfactants such as polyoxyethylene polyoxypropylene block copolymer, sorbitan fatty acid ester, and polyoxyethylene sorbitan fatty acid ester. Examples of the auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like.

Formulation examples are shown below. The compounds of the present invention are shown by the compound numbers in Table 1. Parts indicate parts by weight.

Formulation Example 1 50 parts of the present compound 1, 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain a wettable powder.

Formulation Example 2 The compound of the present invention 2, 5 parts, polyoxyethylene styryl phenyl ether 14 parts, calcium dodecylbenzene sulfonate 6 parts, xylene 30 parts and cyclohexanone 45 parts are thoroughly mixed to obtain an emulsion.

Formulation Example 3 1 part of the present compound 5, 1 part of synthetic hydrous silicon oxide, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 66 parts of kaolin clay are well pulverized and mixed, and water is added and kneaded well, and Granules are dried to obtain granules.

Formulation Example 4 25 parts of the compound of the present invention, 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC and 69 parts of water are mixed and wet-ground until the particle size becomes 5 microns or less to obtain a suspension agent.

The compound of the present invention thus prepared is subjected to soil treatment, foliar treatment or flooding treatment before or after emergence of weeds. The soil treatment includes a soil surface treatment, a soil admixture treatment, and the like, and the foliage treatment includes a treatment from above the plant body and a local treatment such that only the weeds are treated so as not to adhere to the crop.

In addition, the herbicidal effect can be expected to be enhanced by using it in combination with other herbicides. Furthermore, it can be used by mixing with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners and the like.

Incidentally, the compound of the present invention, paddy field, upland, orchard, meadow,
It can be used as an active ingredient of a herbicide for lawn, forest or non-cultivated land.

When the compound of the present invention is used as an active ingredient of a herbicide, its treatment amount is different depending on weather conditions, formulation form, treatment time, method, place, target weed, target crop, etc., but usually 1
The amount is 0.05 g to 100 g, preferably 0.1 g to 50 g per are, and emulsions, wettable powders, suspending agents and the like are usually provided in a predetermined amount of 1 to 10 liters per are (if necessary, spreading It is diluted with water (to which an auxiliary agent such as an agent is added) and treated, and granules and the like are usually treated without any dilution.

As the spreading agent, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate,
Paraffin and the like can be mentioned.

Next, Test Examples will show that the compound of the present invention is useful as an active ingredient of a herbicide. The compounds of the present invention are shown by the compound numbers in Table 1, and the compounds used for comparison and control are shown by the compound symbols in Table 2.

Regarding the herbicidal efficacy, the degree of budding and growth inhibition of the test plant at the time of the survey was visually observed, and when there was no or almost no difference from when the compound was not tested, the test plant died. Or, the one whose growth is completely inhibited is defined as "5" and evaluated in 6 levels of 0 to 5, 0, 1, 2,
Shown as 3, 4, and 5.

Test Example 1 Upland soil treatment test Field soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and seeds of green flesh, Malaga morning glory and velvetleaf were sown.
Covered with soil. The test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the compound was diluted with 10 liters of water per ares, and the soil surface was treated with a small sprayer. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 3.

Test Example 2 Field and foliage treatment test Field soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and seeds of millet, oats, radish, and velvetleaf were sown and grown in a greenhouse for 10 days. Then, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount thereof was diluted with water containing 10 liters of spreading agent per are, and the leaves were treated from above the plant with a small sprayer. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 4.

Test Example 3 Paddy Water Submersion Treatment Test Paddy soil was packed in a cylindrical plastic pot having a diameter of 8 cm and a depth of 12 cm, and seeds of Taenia japonicus and broad-leaved weeds (Azena, Kishigusa, Mizojabe) were mixed at a depth of 1 to 2 cm. After flooding to make it into a paddy field, 2-leaf stage rice was transplanted and grown in a greenhouse. Six days later (the initial stage of the development of each weed), the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount thereof was diluted with 5 ml of water and treated on the water surface. After treatment
It was cultivated in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 5.

Test Example 4 Upland soil treatment test Field soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm,
Soybean, cotton, corn, velvetleaf, physalis,
Aogatetou, Sanaetade, Enokurogusa, and Seibanmokoshi were sown, and the soil was covered to a thickness of 1 to 2 cm. Formulation example 2
The test compound was made into an emulsion in accordance with the procedure of 1. and a predetermined amount thereof was diluted with water equivalent to 10 liters per are, and the soil surface was treated with a small sprayer. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 6.

Test Example 5 Upland field foliage treatment test Field up soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm,
Soybean, cotton, corn, malaga morning glory, velvetleaf, physalis sycamore, and blue-spotted gall were sowed and grown for 18 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount thereof was diluted with 5 liters of water per 1 are containing a spreading agent, and then uniformly sprayed on the entire foliage from above the plant with a small sprayer. Processed. At this time, the growth conditions of weeds and crops differed depending on the grass species, but at the 1 to 4 leaf stage, the plant height was 2 to 12 cm. The herbicidal efficacy was investigated 20 days after the treatment. The results are shown in Table 7. This test was conducted in a greenhouse throughout the entire period.

Test Example 6 Upland soil treatment test Field up soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm,
Wheat, Poa annua, Shiroza, Neoinudoguri, and buckwheat vine were sown and covered with a soil having a thickness of 1 to 2 cm.
The test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the compound was diluted with 10 liters of water per ares, and the soil surface was treated with a small sprayer. After the treatment, the plants were grown in a greenhouse for 27 days and the herbicidal effect was investigated. The results are shown in Table 8.

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Koichi Morita 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (56) Reference JP-A-57-56403 (JP, A)

Claims (2)

[Claims] 1. A general formula [In the formula, R represents a haloalkyl group, a haloalkenyl group, or a haloalkynyl group, and X represents a chlorine atom or a bromine atom. ] The tetrahydrophthalimide derivative shown by these. 2. General formula [In the formula, R represents a haloalkyl group, a haloalkenyl group or a haloalkynyl group, and X represents a chlorine atom or a bromine atom. ] A herbicide characterized by using a tetrahydrophthalimide derivative represented by the following as an active ingredient.