JPH0247465B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention is based on the general formula () [In the formula, R represents an alkyl group having 5 to 8 carbon atoms. ] The present invention relates to an N-phenyltetrahydrophthalimide derivative represented by the following, a method for producing the same, and a herbicide containing the same as an active ingredient. The present inventors have noticed that N-phenyltetrahydrophthalimide derivatives have excellent herbicidal efficacy, and have found that they are less harmful to important crops such as soybean, rice, corn, and wheat, and are effective at low doses. We have continued research into herbicides that have less impact on the environment. As a result, the compound group represented by the general formula () has excellent herbicidal activity at an extremely low dose in field foliage treatment, and has selectivity for important crops such as corn and soybean. They also discovered that when used as a herbicide for rice fields, it exhibits excellent herbicidal power at a low dose, and has excellent properties such as not causing any chemical damage to rice, leading to the completion of the present invention. Ivy. More specifically, the compound of the present invention () exhibits particularly high activity when used in field foliar treatments, and shows that it exhibits particularly high activity when used in field foliar treatments.
theophrasti), sunflower (Helianthus annuus),
It can control Datura stramonium, Ipomoea purpurea, Xanthium strumarium, Solanum nigrum, etc. with a low dose, and at the same time shows good selectivity against corn or soybean. Furthermore, when the compound of the present invention () is used in paddy fields, it is not only highly effective against broad-leaved weeds such as Japanese millet and Japanese grasshopper, azalea, and common grass, but is also effective against problem weeds such as Japanese grasshopper and Japanese grasshopper. There is little chemical damage to paddy rice. As a compound similar to the compound of the present invention,
There is N-(4-chloro-2-fluorophenyl)-3,4,5,6-tetrahydrophthalimide (comparative compound A) described in JP-A-51521, but as shown in the examples below, the compound of the present invention () shows much higher efficacy in post-germination foliage treatment,
The selectivity for corn and soybean was also excellent. When used as a herbicide for paddy fields, the compound () of the present invention can be used to treat annual weeds such as Japanese millet and Japanese grasshopper.
It is highly effective against perennial weeds such as weeds, and can be controlled with lower doses than comparative compounds. Furthermore, the safety against rice was also superior to that of the comparative compound. The compound of the present invention represented by the general formula () is synthesized by the reactions represented by the following reaction formulas (a) and (b). [In the formula, R is as described above, X represents a halogen atom, and M represents an alkali metal atom. ] Reaction (a) is carried out by refluxing the aniline derivative () and 3,4,5,6-tetrahydrophthalic anhydride in the presence of an inert solvent such as acetic acid. In reaction (b), the N-phenyltetrahydrophthalimide derivative () and the alkyl halide () are reacted at room temperature to 100°C, preferably 60 to 80°C, in the presence of a solvent such as acetonitrile, dimethylformamide, or dimethylsulfoxide. It is done by letting When actually using the compound of the present invention, the active substance itself may be sprayed, or it may be used in the form of granules, wettable powders, or emulsions. In preparing these pharmaceutical products, solid carriers such as mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiyquilite, gypsum,
Calcium carbonate, apatite, etc.), vegetable powders (soybean flour, wheat flour, wood flour, tobacco powder, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin,
Polyvinyl chloride, dammar gum, ketone resin, etc.), alumina, waxes, etc. Examples of liquid carriers include alcohols (methyl alcohol, ethyl alcohol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, methylnaphthalene, etc.), chlorinated hydrocarbons (chloroform, (carbon tetrachloride, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexane, etc.), esters (ethyl acetate, butyl acetate, ethylene glycol acetate, etc.), acid amides (dimethylformamide, etc.) ), acetonitrile, ethylene glycol ethyl ether, water, etc. The surfactant used for the purpose of emulsification, dispersion, spreading, etc. may be nonionic, anionic, cationic, or amphoteric. Examples of surfactants used include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl ether, polyoxyethylene fatty acid ester, sorbitan fatty acid ester, oxyethylene oxypropylene polymer, polyoxyethylene sorbitan fatty acid ester, polyoxy These include ethylene alkyl phosphates, fatty acid salts, alkyl sulfate salts, alkyl sulfonates, alkylaryl sulfonates, alkyl phosphate salts, polyoxyethylene alkyl sulfate esters, quaternary ammonium salts, etc. It is not limited to only. For these purposes, gelatin, casein, sodium alginate, starch, agar,
Polyvinyl alcohol or the like can be used as an adjuvant. Furthermore, the active ingredient in the formulation can be adjusted to various proportions from 1% to 50%, and the herbicidal effect can be exerted by applying 1 to 80 g per 1a of the active ingredient. Examples of formulations of this herbicide are shown below. Formulation Example 1 25 parts by weight of compound (1), 2.5 parts by weight of dodecylbenzenesulfonate, 2.5 parts by weight of lignosulfonate and 70 parts by weight of diatomaceous earth are thoroughly ground and mixed to obtain a wettable powder. Formulation example 2 Compound (3) 30 parts by weight, emulsifier Sorbol SM100
(Toho Chemical registered trademark name) 10 parts by weight and xylene
Mix 60 parts by weight thoroughly to obtain an emulsion. Formulation example 3 5 parts by weight of compound (1), 1 part by weight of white carbon, 5 parts by weight of lignin sulfonate and clay
89 parts by weight are thoroughly ground and mixed, water is added and the mixture is thoroughly kneaded, followed by granulation and drying to obtain granules. Formulation Example 4 4 parts by weight of compound (2), 1 part by weight of isopropyl phosphate, 65 parts by weight of clay and 30 parts by weight of talc are thoroughly ground and mixed to obtain a powder. Formulation Example 5 40 parts by weight of bentonite, 5 parts by weight of lignin sulfonate and 55 parts by weight of clay are pulverized and mixed, added with water, kneaded and then granulated and dried to obtain granules containing no active ingredient. Granules are obtained by impregnating 95 parts by weight of the granules with 5 parts by weight of compound (4). Formulation Example 6 20 parts by weight of compound (2) was mixed with 60 parts by weight of an aqueous solution containing 3% by weight of polyoxyethylene sorbitan monolactate, wet-pulverized until the particle size of the active ingredient became 3μ or less, and then added as a dispersion stabilizer. By mixing 20 parts by weight of an aqueous solution containing 3% by weight of sodium alginate, 100 parts by weight of a suspension preparation is obtained. Furthermore, the compound of the present invention can be used in combination with other herbicides to improve its effectiveness as a herbicide, and in some cases, a synergistic effect can be expected. Examples include 2,4-dichlorophenoxyacetic acid; 2-methyl-4-chlorophenoxyacetic acid (including esters and salts), γ-(2-methyl-
Phenoxy herbicides such as 4-chlorophenoxy) butyric acid, 2,4-dichlorophenyl-4'-nitrophenyl ether; 2,4,6-trichlorophenyl-4'-nitrophenyl ether; 3-methylphenyl-4' -nitrophenyl ether; 2,4-
Dichlorophenyl-4'-nitro-3'-methoxyphenyl ether; 2,4-dichlorophenyl-
Diphenyl ether herbicides such as 3'-methoxycarbonyl-4'-nitrophenyl ether, 2-chloro-4,6-bisethylamino-1,3,5-
Triazine; 2-chloro-4-ethylamino-6
-isopropylamino-1,3,5-triazine; 2-methylthio-4,6-bisethylamino-1,3,5-triazine; 2-methylthio-
4,6-bisisopropylamino-1,3,5-
Triazine; 2-methylthio-4-ethylamino-6-(1,2-dimethylpropyl)amino-1,
Triazine herbicides such as 3,5-triazine, 3
-(3,4-dichlorophenyl)-1,1-dimethylurea; 3-(3,4-dichlorophenyl)-1
-Methoxy-1-methylurea; 3-(3-chloro-4-difluorochloromethylthiophenyl)
-1,1-dimethylurea; 1-(2-phenylpropyl)-3-(4-methylphenyl)urea;
Urea herbicides such as N-(α,α-dimethylbenzyl)-N′-(4-methylphenyl)urea, isopropyl N-(3-chlorophenyl) carbamate;
Carbamate herbicides such as methyl N-(3,4-dichlorophenyl) carbamate; thiols such as S-(4-chlorobenzyl)-N,N-diethylthiol carbamate; S-ethyl-N,N-hexamethylenethiol carbamate; Carbamate herbicide, 3,4-dichloropropionanilide; N-methoxymethyl-2,6-diethyl-2
-Chloracetanilide; 2-chloro-2',6'-
Diethyl-N-(butoxymethyl)-acetanilide; N-chloroacetyl-N-(2,6-diethylphenyl)glycine ethyl ester, N-(α,
Acid amide herbicides such as α-dimethylbenzyl)-α-bromtertiary-butylacetamide, 5-
Bromo-3-secondary-butyl-6-methyluracil; Uracil herbicides such as 3-cyclohexyl-5,6-trimethyleneuracil, 1,1'-dimethyl-4,4'-bisviridinium dichloride, etc. Pyridinium salt herbicide, N,N-bis(phosphonomethyl)glycine; 0-ethyl 0-(2-
Nitro-5-methylphenyl)N-Secondary-
Butyl phosphoramidothioate; S-(2-methyl-1-piperidylcarbonylmethyl)0,0
-dipropylphosphorodithioate; phosphorus herbicides such as 0-methyl 0-(2-nitro-4-methylphenyl) N-isopropylphosphoramidothionate, α,α,α-trifluoro-2,6- Toluidine herbicides such as dinitro-N,N-dipropyl-p-toluidine, 5-tert-butyl-3-
(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one; 3-isopropyl-1H-2,1,3-benzothiadiazine-(4)- 3H-one-2,2-dioxide; α-(β-naphthoxy)propionanilide; 2-(α-naphthoxy)-N,N-diethylpropionamide: 3,3'-dimethyl-4-methoxybenzophenone, 4-(2,4-dichlorobenzoyl)-1,3-dimethylpyrazole-5-
Examples include, but are not limited to, yl-p-toluenesulfonate. The herbicide of the present invention can also be used in combination with fungicides, microbial pesticides, pyrethroid insecticides, other insecticides, plant growth regulators, fertilizers, and the like. Next, the present invention will be explained in more detail with reference to Examples. Example 1 N-(4-chloro-2-fluoro-5-n-amyloxyphenyl)-3,4,5,6-tetrahydrophthalimide N-(4-chloro-2-fluoro-5-hydroxyphenyl )-Dissolve 2.95 g of 3,4,5,6-tetrahydrophthalimide in 20 ml of DMF, add 7.6 g of potassium carbonate, and further add 1.6 g of n-amyl bromide. This is stirred at 70-80°C for 3 hours. Water was added to the reaction solution and extracted with ether. The ether layer was washed with water, dried and concentrated, and the residue was purified by silica gel chromatography to obtain 0.63 g of crystals. mp100.8℃ This is N-(4-chloro-2-
fluoro-5-n-amyloxyphenyl)-3,
It was confirmed that it was 4,5,6-tetrahydrophthalimide. The compounds shown in Table 1 were synthesized in exactly the same manner as in Example 1.

【table】

[Table] Example 2 (Paddy field-like pre-emergence soil treatment test) Fill a 1/5000a Wagner pot with soil, fill it with water to make it flooded, then transplant rice at the 3-leaf stage, and then add Japanese millet, Japanese grass, and broad-leaved weeds. , planted with seeds or tubers of pine buffalo and urticaria. 5
A day later, when each weed started to germinate, a predetermined amount of the active substance was made into an emulsion and dropped onto the water surface. Three weeks after the chemical treatment, the herbicidal efficacy and rice damage were investigated, and the results are shown in Table 2. Evaluation of herbicidal efficacy was expressed as a number from 0 to 5 as shown below. Rice damage was also expressed using the same criteria as herbicidal efficacy. 0... Weed suppression rate 0-9% 1... 10-29% 2... 30-49% 3... 50-69% 4... 70-89% 5... 90-100%

[Table] Example 3 (Treatment of foliage after germination in upland fields) Pack field soil into plastic trays measuring 35 cm in length, 25 cm in width, and 10 cm in height, and plant soil for corn, soybeans, Japanese crocodile, sunflowers, morning glories, mulva morning glories, Japanese fir trees, and Japanese cornsopia. After sowing and cultivating green foxtail for two weeks in a greenhouse, two of these trays were arranged in a frame measuring 50 cm in height, 100 cm in width, and 40 cm in height, and a predetermined amount of each chemical was applied from above the plants using a small sprayer. The entire area within the frame was treated with stems and leaves. After being grown in a greenhouse for three more weeks after spraying the chemicals, each plant was examined for phytotoxicity or herbicidal efficacy on a scale of 0 to 5, as in Example 2. The results are shown in Table 3. The processing agent used was an emulsion made according to the recipe in Formulation Example 3, and water with a spreading agent added.
A 25 ml emulsion was used for testing. The size of the plants at the time of chemical treatment varied depending on the species, but they were approximately 2 to 20 cm tall at the 1 to 3 true leaf stage.

【table】

Claims (1)

[Claims] 1. General formula [In the formula, R represents an alkyl group having 5 to 8 carbon atoms. ] N-phenyltetrahydrophthalimide derivative represented by these. 2 General formula [In the formula, R represents an alkyl group having 5 to 8 carbon atoms. ] General formula characterized by reacting the aniline derivative represented by and 3,4,5,6-tetrahydrophthalic anhydride [In the formula, R is as described above. ] A method for producing an N-phenyltetrahydrophthalimide derivative shown in the following. 3 General Formula RX [In the formula, R represents an alkyl group having 5 to 8 carbon atoms, and X represents a halogen atom. ] Halogen compounds and general formula shown by [In the formula, M represents an alkali metal atom. ] A general formula characterized by reacting with an N-phenyltetrahydrophthalimide derivative represented by [In the formula, R is as described above. ] A method for producing an N-phenyltetrahydrophthalimide derivative shown in the following. 4 General formula [In the formula, R represents an alkyl group having 5 to 8 carbon atoms. ] A herbicide characterized by containing an N-phenyltetrahydrophthalimide derivative as an active ingredient.