JP2634068B2 - Benzamide derivatives - Google Patents

Description

The present invention relates to a specific benzamide derivative and a herbicide and a plant growth regulator containing the benzamide derivative.

The present inventors have been examining the herbicidal activity of various compounds and the activity of regulating the growth of plants. In some cases, they have been found to exert various effects, such as promoting the development of axillary buds, and have conducted various studies to complete the present invention. That is, the first invention in the present invention is a benzamide derivative shown below, and the second and third inventions are a herbicide and a plant growth regulator containing the benzamide derivative as an active ingredient.

General formula (In the formula, A is a hydrogen atom or a methyl group, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, or a cyclic alkyl group and a cyclic alkenyl group including R ₁ and R _2. A benzamide derivative represented by the following formula:

The herbicide and the plant growth regulator of the present invention are obtained by mixing the active ingredient compound with various carriers due to its physicochemical properties,
It can be obtained by formulating into wettable powders, emulsions, liquids, granules, powders, flowables and the like. In addition, a surfactant may be added in order to impart emulsifiability, dispersibility, spreadability, and the like during preparation of the preparation. Further, if necessary, a fertilizer, a herbicide, an insecticide, a fungicide and a tank mix or an integrated preparation may be applied.

Inert inorganic materials such as bentonite,
Clay, zeolite, talc and the like can be mentioned, and as the organic solvent, a solvent in which each compound is well dissolved, for example, xylene, toluene, cyclohexanone, glycols and the like can be mentioned. Examples of the dispersant, emulsifier, spreading agent, and the like include anionic and nonionic surfactants such as lignin sulfonate, naphthalene sulfonate, dialkyl sulfosuccinate, polyoxyethylene nonylphenyl ether, and polyoxyethylene. Examples include ethylene stearyl ether and polyoxyethylene dodecyl ether.

In order to use the present invention as a herbicide, the active ingredient compound is sufficiently applied so as to exhibit a desired herbicidal effect. The application rate is in the range of 50 to 2000 g / 10a of the active ingredient, but usually 100 to 500 g / 10a is desirable. The active ingredient compound is formulated into a wettable powder, emulsion, powder, granule or the like containing 0.1 to 90 parts by weight, preferably 2 to 80 parts by weight, and used.

When the present invention is used as a herbicide, it mainly suppresses germination of weeds and causes death. In field treatment of upland soil, it exhibits an action as a herbicide having selectivity for corn, soybean and the like.

In order to use the present invention as a plant growth regulator, the application rate varies depending on the crop type, the compound, and the treatment time, but is applied in the range of 1 to 1000 g / 10a of the active ingredient, usually 5 to 200 g / 10a. It is desirable to be done. The active ingredient compound is used in the form of a wettable powder, emulsion, powder, granule or the like containing 0.1 to 80 parts by weight, desirably 1 to 80 parts by weight.

When the present invention is used as a plant growth regulator, it is mainly absorbed from the foliage of the plant, moves in the plant, and exerts an action intensively at a site where growth is active. Although the form of the action varies depending on the compound, concentration, plant species, or growth stage, it is presumed that the action is exerted on the levels of the plant hormones auxin and gibberellin.

As a specific effect, in the grasses, the internodes are shortened immediately after the foliage application, and in some cases, tillering is promoted. Also, in broadleaf plants, the occurrence of new shoots is suppressed, the length of seeds is prevented, or the formation of axillary buds and the formation of flower buds are accelerated.

Therefore, there are a wide range of applications such as a lodging-reducing agent, a hedge-cutting agent, a lawn-cutting agent, a flowering tree dwarfing agent, and a fruit-tree thinning agent.

Next, typical benzamide derivatives according to the present invention are shown in Table 1. In addition, methods for synthesizing representative compounds will be described based on Examples.

 Hereinafter, each compound is indicated by a compound No.

The benzamide derivative of the present invention has the general formula [I] (Wherein A represents H or CH ₃ , X represents a halogen atom) and a compound represented by the general formula [II]: (Wherein, R ₁ and R ₂ have the same meanings as in the above general formula) in an organic solvent such as acetone, toluene, dioxane or the like in an inorganic base such as sodium hydrogen carbonate or potassium carbonate. Alternatively, by reacting in the presence of an organic base such as pyridine and triethylamine, it can be obtained easily and in high yield.

Further, the compound of the general formula [I] comprises 4-hydroxy-N- (2,3-dichlorophenyl) -benzamide,
By reacting haloacetate or 2-halopropionate in an aqueous solution or an organic solvent such as methal, acetonitrile, dioxane or a mixed solvent thereof in the presence of an inorganic base such as sodium hydroxide. Thus, 4- (2,3-dichlorophenylcarbamoyl) -phenoxyacetate acid or 2-
After obtaining [4- (2,3-dichlorophenylcarbamoyl) -phenoxy] -propionite acid, these are treated with an inorganic halide such as thionyl chloride or an organic halide such as phosgene, dioxane, toluene. Can be obtained by reacting in an organic solvent such as

Next, examples of the synthesis of representative compounds of the present invention will be described with reference to examples, but the present invention is not limited thereto.

Example 1 (Synthesis of Compound No. 7 in Table 1) 4-Hydroxy-N- (2,3-dichlorophenyl)-
2.82 g of benzamide and 1.84 g of 2-bromopropionate acid were dissolved in 10 ml of dioxane, and a mixture of 0.97 g of sodium hydroxide and 2 ml of water was added dropwise to this solution over 10 minutes while stirring at 20 ° C. After completion of the dropwise addition, the mixture was stirred at 80 ° C. for 2 hours, poured into 50 ml of water, acidified with hydrochloric acid, and the resulting precipitate was separated and the crude product was recrystallized from toluene-methanol to obtain the desired product. 2- [4- (2,3-
2.6 g of dichlorophenylcarbamoyl) -phenoxy] -propionate acid were obtained. To this compound, 30 ml of dioxane and 3.57 g of thionyl chloride were added, and the mixture was stirred at 80 ° C. for 4 hours. Excessive thionyl chloride, dissolved hydrochloric acid gas, sulfurous acid gas and dioxane were removed by evaporation to obtain 2- [4- (2,3-dichlorophenylcarbamoyl) -phenoxy] -propionyl chloride as a residue.

On the other hand, a solution prepared by dissolving the above acid chloride in 5 ml of acetone in a mixture of 0.54 g of acetone oxime, 0.93 g of sodium hydrogen carbonate and 20 ml of acetone was added dropwise over 5 minutes while stirring at room temperature. After completion of the dropwise addition, the mixture was further stirred at room temperature for 5 hours. After completion of the reaction, 50 ml of dichloromethane was added,
After extraction and washing with water, the solvent is distilled off after drying, and the obtained residue is recrystallized from toluene to give acetone-
2.7 g of o- [2- [4- (2,3-dichlorophenylcarbamoyl) -phenoxy] -propionyl] -oxime were obtained. The yield was 90% and the melting point was 86.5-88 ° C.

Example 2 (Synthesis of No. 31 compound in Table 1) 1.0 g of cyclohexanone oxime and sodium hydrogen carbonate
To a mixture of 1.26 g and 20 ml of acetone, 3.75 g of 4- (2,3-dichlorophenylcarbamoyl) -phenoxyacetyl chloride synthesized in the same manner as in Example 1 and acetone 5
ml of the solution were added dropwise over 5 minutes while stirring at room temperature.
After completion of the dropwise addition, the mixture was further stirred at room temperature for 5 hours. After the reaction,
The same treatment as in Example 1 was carried out, and cyclohexanone-
o- [4- (2,3-dichlorophenylcarbamoyl)-
[Phenoxyacetyl] oxime 3.8 g was obtained. 87.4 yield
In%, the melting point was 105-108.5 ° C.

Next, the herbicide and the plant growth regulator of the present invention will be described with reference to formulation examples and test examples.

Formulation Example 1. Preparation of wettable powder Add 40 parts of compound No. 5 to 52 parts of kaolin clay and 3 parts of white carbon, mix and grind with a grinder, and then powdered surfactant, Solpol 5039 (Toho Chemical Co., Ltd.) (Trademark) 5
And Compound No. 5 to obtain a No. 5 40% wettable powder. Formulation Example 2. Preparation of emulsion 15 parts of Compound No. 13 was dissolved in 42 parts of xylene and 33 parts of cyclohexanone, 10 parts of Solpol 800A was added, and the mixture was stirred and dissolved. A 15% emulsion of No. 13 was obtained.

Formulation Example 3. Preparation of powder 5 parts of a 40% wettable powder of compound No. 15 and 0.3 part of lapizole BB-75 (trademark of NOF Corporation) prepared in the same manner as in Formulation Example 1
Parts and 94.7 parts of clay were mixed well to obtain 2% powder of Compound No. 15.

Formulation Example 4. Preparation of fine granules 3 parts of white carbon and 47 parts of kaolin clay are mixed and pulverized with 50 parts of compound No. 24 to make 50%, and 2 parts thereof are mixed in 96 parts of fine zeolite being stirred in a speed kneader. While diluting with 2 parts of polyoxyethylene dodecyl ether in water while stirring and preparing with a small amount of water until no powder is left.
% Fine granules were obtained.

Test Example 1 Upland Soil Treatment Test Upland soil was filled in a pot of 400 cm ² , and seeds of Aobu, Shiroza and Meishibashi were mixed in a surface layer of 0.5 cm, and wheat, corn and soybean seeds were sown at a depth of 3 cm.

After seeding, a diluted solution of each test compound was sprayed on the soil surface in a predetermined amount of each drug. On the 30th day after the treatment, the herbicidal effect on various weeds and the response of various crops to the drug were investigated. The results are shown in Table 2.

 The criteria for the survey are as follows.

Herbicidal effect Chemical damage of crop 0: Same as no treatment-: No harm 1: 20% control ±: Slight harm 2: 40% control +: Small harm 3: 60% control: Moderate harm 4: 80% control: Major harm 5: Complete Control Test Example 2. Various plant foliage treatment tests (plant growth regulator) Rice, barley, kidney beans, and lettuce are grown separately in unglazed pots of 60 cm, thinned out according to the size of the plant,
After adjusting the growth degree to the 2-3 leaf stage, a spreading agent was added to the diluted solution of each test compound, and 100 / 10a equivalent was sprayed on the foliage using a spray gun. On the 30th day after the treatment, the degree of growth from the time of the treatment was investigated by observation. The results are shown in Table 3.

The criteria for the survey were as follows, assuming that no treatment was 0 and the plant height at the time of treatment was 5.

Plant height control effect 0: Same as no treatment Dark greening: G 1: 20% plant height control Tillering: T 2: 40% plant height control Orthogonal leaf: M 3: 60% plant height control Leaf withering: B 4: 80% plant height Inhibition 5: 100% plant height suppression (no growth of plant height at all) [hereinafter based on this standard] Test Example 3 Azalea foliage treatment test Azalea seedlings (tree height 25 to 30 cm) grown in unglazed pots of 200 cm ²
The diluted solution of each test compound is thoroughly wetted (250
/ 10a) Sprayed, pruned 7 days later, and observed two months later by observation. The results are shown in Table 4.

 The investigation criteria are the same as in Test Example 2.

Test Example 4 Wheat foliage treatment test A field of wheat (Norin 61) sown in early November was 5 m ×
It was divided into 2m and made into one unit area. On the 14th before heading in late April, 100 / 10a of the diluted solution of each compound was sprayed over the whole area using a hand-pressed sprayer.

In mid-June, the culm length, ear length, number of ears per unit area, and grain weight were investigated for 50 stems of average growth. In addition, since the degree of lodging was moderate in the non-treated section, the section in which the reduction effect was clearly recognized was marked with a circle. The results are shown in Table 5.

 Numerical values are percentages of the untreated ratio, and the values in parentheses indicate actual measured values.

Test example 5 Tefton turf spray test Tefton turf (T-328) was divided into 1m x 1m
One unit area. 3 days after pruning 100 dilutions of each compound
Sprayed over the whole area using a hand-pressed sprayer equivalent to / 10a. After spraying, 15 days later, the degree of growth from the time of treatment was examined by observation. The results are shown in Table 6.

 The investigation criteria are the same as in Test Example 2.

Claims (3)

(57) [Claims] (1) General formula (In the formula, A is a hydrogen atom or a methyl group, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, or a cyclic alkyl group and a cyclic alkenyl group including R ₁ and R _2. A benzamide derivative represented by the formula: 2. The general formula (In the formula, A is a hydrogen atom or a methyl group, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, or a cyclic alkyl group and a cyclic alkenyl group including R ₁ and R _2. A herbicide containing a benzamide derivative represented by the following formula: 3. The general formula (In the formula, A is a hydrogen atom or a methyl group, R ₁ and R ₂ are a hydrogen atom, an alkyl group, an alkoxy group, an alkenyl group, an aryl group, or a cyclic alkyl group and a cyclic alkenyl group including R ₁ and R _2. A plant growth regulator containing a benzamide derivative represented by the following formula: