JPS6259693B2 - - Google Patents

Description

[Detailed description of the invention]

The present invention relates to certain benzamide derivatives and herbicides containing the benzamide derivatives. The present inventors investigated the herbicidal activity of various compounds and discovered the unique action of a specific benzamide derivative, leading to the completion of the present invention. That is, the first invention of the present invention is a benzamide derivative shown below, and the second invention is
This is a herbicide containing the benzamide derivative as an active ingredient. general formula (R in the formula is a lower dialkylamino group different from each other, an N-alkylcyclohexylamino group,
It represents a dialkyl-substituted-1-pyrrolidyl group, a dialkyl-substituted piperidino group, a morpholino group, or a 1-thiazolidyl group. ) Next, typical benzamide derivatives according to the present invention are shown in Table 1.

[Table] The compounds of the present invention are 4-hydroxy-N-
(2,3-dichlorophenyl)-benzamide and various carbamoyl chlorides are mixed in the presence of inorganic basic salts such as potassium carbonate and sodium carbonate, or organic basic substances such as pyridine and triethylamine, etc. in acetone, benzene, toluene, Alternatively, 4-hydroxy-
4-chlorocarbonyloxy-N-(2,3-dichlorophenyl)-benzamide obtained by reacting N-(2,3-dichlorophenyl)-benzamide with phosgene and various secondary amines,
It can be synthesized by a reaction method in an organic solvent such as acetone, tetrahydrofuran, dioxane, and dimethyl sulfoxide in the presence of an organic basic substance such as pyridine and triethylamine. Next, a typical synthesis example will be shown. Synthesis Example 1 (Synthesis of Compound No. 1 in Table 1) 2.00 g of 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide, 1.31 g of n-butylmethylcarbamoyl chloride, and 10 ml of acetone.
To the suspension consisting of the above, 0.90 g of triethylamine was added dropwise little by little at room temperature while stirring. After the dropwise addition, the mixture was further stirred at acetone reflux temperature for 5 hours to complete the reaction. The solvent was then recovered on a rotary evaporator and the residue was dissolved in 300 ml of toluene. This solution was added twice with 150 ml of 5% hydrochloric acid water, then with 150 ml of water.
After washing twice with water and dehydrating with anhydrous salt water, toluene was recovered using a rotary evaporator. The obtained residue was recrystallized from toluene to obtain the desired 4-n-butylmethylcarbamoyloxy-N-(2,3-
2.03 g of dichlorophenyl)-benzamide was obtained. The yield is 72.5% and the melting point of this compound is 89.0~
It was 90.0℃. Synthesis Example 2 (Synthesis of Compound No. 2 in Table 1) In Synthesis Example 1, 1.43 g of n-butylethylcarbamoyl chloride was used instead of 1.31 g of n-butylmethylcarbamoyl chloride, and the following Synthesis Example 1 and Reacts in the same way, melting point 78.0 ~
2.14 g of the target product 4-n-butylethylcarbamoyloxy-N-(2,3-dichlorophenyl)-benzamide having a temperature of 79.5°C was obtained. The yield is
It was 73.8%. Synthesis Example 3 (Synthesis of Compound No. 3 in Table 1) 1.53 g of N-methylcyclohexylcarbamoyl chloride was used instead of 1.31 g of n-butylmethylcarbamoyl chloride in Synthesis Example 1, and the following procedure was the same as in Synthesis Example 1. reacts with melting point
4-(N-methylcyclohexylcarbamoyloxy)-N- of the target product having a temperature of 121.0 to 123.0°C
(2,3-dichlorophenyl)-benzamide 2.05
g was obtained. The yield was 68.9%. Synthesis Example 4 (Synthesis of compound No. 4 in Table 1) 4-chlorocarbonyloxy-N-(2,3-
2.00 g of (dichlorophenyl)-benzamide was dissolved in 20 ml of acetone, and 1.72 g of 2,5-diethylpyrrolidine was added dropwise little by little at room temperature while stirring. After the dropwise addition, the mixture was further stirred at room temperature for 8 hours to complete the reaction. The solvent was then recovered on a rotary evaporator and the residue was dissolved in 200 ml of ethyl acetate.
This solution was added twice with 150 ml of 5% hydrochloric acid water and then with 150 ml of water.
After washing twice with water and dehydrating with anhydrous salt water, ethyl acetate was recovered using a rotary evaporator. The obtained residue was washed with methanol to obtain the desired 4-(2,
1.66 g of 5-dimethyl-1-pyrrolidylcarbonyloxy)-N-(2,3-dichlorophenyl)-benzamide was obtained. The yield was 70.5%, and the melting point of this compound was 96.0-100.0°C. Synthesis Example 5 (Synthesis of Compound No. 5 in Table 1) In Synthesis Example 4, 2,5-dimethylpyrrolidine
Using 1.97 g of 3,5-dimethylpiperidine instead of using 1.72 g, the following reaction was carried out in the same manner as in Synthesis Example 4, and the target product 4-
1.70 g of (3,5-dimethylpiperidinocarbonyloxy)-N-(2,3-dichlorophenyl)-benzamide was obtained. The yield was 69.5%. Synthesis Example 6 (Synthesis of Compound No. 6 in Table 1) In Synthesis Example 4, 2,5-dimethylpyrrolidine
Using 1.51 g of morpholine instead of 1.72 g and reacting in the same manner as in Synthesis Example 4, the melting point was 164.0.
1.66 g of the desired product, 4-morpholinocarbonyloxy-N-(2,3-dichlorophenyl)-benzamide, having a temperature of -167.0°C was obtained. The yield is
It was 72.4%. Synthesis Example 7 (Synthesis of Compound No. 7 in Table 1) 2,5-dimethylpyrrolidine in Synthesis Example 4
If 1.44 g of thiazolidine is used instead of 1.72 g and the reaction is carried out in the same manner as in Synthesis Example 4, the melting point
1.47 g of the desired product, 4-(1-thiazolidylcarbonyloxy)-N-(2,3-dichlorophenyl)-benzamide, having a temperature of 139.5 to 141.5°C was obtained. The yield was 64.8%. The herbicide of the present invention is obtained by mixing the active ingredient compound with various carriers and formulating the mixture in the form of a wettable powder, emulsion, powder, granule, or the like. Among the carriers, liquid carriers include ordinary organic solvents, solid carriers include
Ordinary mineral fines are used. Additionally, a surfactant can be added to impart emulsifying properties, dispersibility, spreading properties, etc. during preparation of the formulation. Furthermore, it can also be used in combination with agricultural chemicals such as fertilizers, herbicides, insecticides, and fungicides. For use as a herbicide, the active ingredient compound is applied in a sufficient amount to achieve the desired herbicidal action. The application amount is 1 to 2000g of active ingredient/10a
Within the range of 1 to 1000 g/10a, preferably 100 to 500 g/10a. Active ingredient
It is used in formulations such as wettable powders, emulsions, powders, and granules containing 0.1 to 50%. To form an emulsion, the active ingredient is dissolved in an agriculturally acceptable organic solvent and a solvent-soluble emulsifier is added.
Suitable solvents are usually water-immiscible and are organic solvents such as hydrocarbons, chlorinated hydrocarbons, ketones, esters, alcohols and amides. Useful solvents include toluene, xylene, naphtha,
Mention may be made of perchlorethylene, cyclohexanone, isophorone and dimethylformamide or mixtures thereof. Particularly suitable solvents are:
Aromatic hydrocarbons and ketones, but usually mixtures of solvents are used. The surfactant used as an emulsifier is approximately
It accounts for 0.5 to 20 parts by weight and may be anionic, cationic, or nonionic. Anionic surfactants include alcohol sulfates or sulfonates, alkylaryl sulfonates or sulfosuccinates, such as calcium dodecylbenzenesulfonate or sodium dioctylsulfosuccinate. Cationic surfactants include fatty alkyl amine salts and fatty acid alkyl quaternary salts, such as laurylamine hydrochloride or lauryldimethylbenzylammonium chloride. Nonionic emulsifiers that can be used include ethylene oxide adducts of alkylphenols, fatty alcohols, mercaptans or fatty acids, such as polyethylene glycol esters of stearic acid or polyethylene glycol ethers of palmityl alcohol or octylphenol. The concentration of active ingredient is between 5 and 80 parts by weight, especially 10
A suitable range is from 30 parts by weight. Wettable powders are prepared by adding the active ingredient to an inert, finely divided solid carrier and a surfactant. Active ingredients are 5
50 parts by weight, and the surfactant is 0.5 parts by weight.
It is usually present in amounts ranging from 20 parts by weight. Solid carriers commonly used for formulating the active ingredients are naturally occurring clays, silicates and silicas, limes and carbonates and organic carriers. Typical examples of these are kaolin, ziecrite, fuller's earth, talc, diatomaceous earth, magnesium lime, dolomite and walnut flour. Commonly used emulsifiers and wetting agents are polyoxyethylenated alkylphenols, fatty alcohols, fatty acids and alkylamines, alkylarylsulfonates and dialkylsulfosuccinates, and the like. Spreading agents include glycerin mannitutraureate and condensates of oleic acid and polyglycerin modified with phthalic anhydride, and dispersants include copolymers of maleic anhydride and olefins such as diisobutylene. The sodium salt of a combination, sodium lignin sulfonate, sodium formaldehyde-naphthalene sulfonate, and the like are used. Powders are prepared by combining the active ingredient with inert carriers customary for the manufacture of powders, such as talc, finely divided clay, pylori, diatomaceous earth, magnesium carbonate or wheat flour. Concentrated powders containing active ingredient present in the range of 10 to 80 parts by weight are commonly prepared, but for application as herbicides, further solids are added to dilute to about 1 to 20 parts by weight. Granules contain the active ingredient in granulated or pelleted form in an agriculturally acceptable carrier, e.g.
Made by mixing 60 to 60 mesh of granular clay, vermiculite, charcoal, or bran. Such granules contain 1 to 50 parts by weight of the active ingredient. The herbicide of the present invention mainly suppresses the germination and growth of weeds, and exhibits an outstanding control effect on grass weeds such as field weeds, slime grass, and azaleas, as well as grass weeds of the water mallow family, especially in soil treatment under flooded conditions. It is also a highly selective herbicide that has a growth-suppressing effect on broad-leaved weeds such as chickweed and weed, and has almost no effect on transplanted paddy rice. Next, the herbicide of the present invention will be explained using formulation examples and test examples. Formulation example 1 (Preparation of hydrating powder) Zeeklite (trademark of Zeeklite Chemical Co., Ltd.)
97 parts by weight, 1.5 parts by weight of Neopellex powder (trademark of Kao Atlas Co., Ltd.) and 1.5 parts by weight of Solbol 800A (trademark of Toho Chemical Industries, Ltd.) were ground and mixed to obtain a carrier for a wettable powder. 90 parts by weight of this carrier and 10 parts by weight of 4-(n-butylmethylcarbamoyloxy)-N-(2,3-dichlorophenyl)-benzamide (compound No. 1 in Table 1) were uniformly pulverized and mixed, and then mixed with water. It was used as a Japanese medicine. Formulation Example 2 (Preparation of emulsion) 4-morpholinocarbonyloxy-N-(2,
10 parts by weight of 3-dichlorophenyl)-benzamide (compound obtained in Synthesis Example 6: Compound No. 6 in Table 1), 40 parts by weight of dichlorohexanone, 40 parts by weight of xylene, and 10 parts by weight of Solpol 800A were uniformly mixed. It was dissolved to form an emulsion. Test Example A 1/15,500 are porcelain pot was filled with paddy soil, and seeds of wild grass, slime grass, and azalea were uniformly sown on the surface layer, and the pot was flooded to a depth of 2 cm. Furthermore, two paddy rice seedlings (variety: Nipponbare) at the second leaf stage were transplanted. Thereafter, before the weeds germinate, a predetermined amount of a diluted hydrating powder of each test compound was dropped into water. On the 20th day after drug treatment, novies,
The herbicidal efficacy against slimy grass and Azegaya, and the response of transplanted paddy rice to the drug were observed and investigated according to the following criteria. Weeding effect Plant damage to transplanted paddy rice 0: No effect (no effect) −: Harmless 1: Slight ±: Slight damage 2: Small +: Slight damage 3: Medium 〓: Medium damage 4: Large 〓: Large damage 5: Extremely large (100%) Weeding) The results are shown in the table below.

【table】

[Table] As is clear from Table 2, the herbicide containing the compound of the present invention has an excellent herbicidal effect and causes almost no phytotoxicity to paddy rice.

Claims (1)

[Claims] 1. General formula (R in the formula represents a lower dialkylamino group, an N-alkylcyclohexylamino group, a dialkyl-substituted 1-pyrrolidyl group, a dialkyl-substituted piperidino group, a morpholino group or a 1-thiazolidyl group) . 2 General formula (R in the formula represents a lower dialkylamino group, an N-alkylcyclohexylamino group, a dialkyl-substituted 1-pyrrolidyl group, a dialkyl-substituted piperidino group, a morpholino group or a 1-thiazolidyl group) Herbicide containing.