JPH02178266A - Nicotinic acid anilide compound and herbicide containing the compound - Google Patents

Abstract

NEW MATERIAL:The nicotinic acid anilide compound of formula I (X is methyl or halogen). EXAMPLE:N-(2-methyl-3-chlorophenyl)-2-(3-trifluoromethylphenoxy)-nicot inamide. USE:Useful as a herbicide exhibiting selective herbicidal effect against broad- leaved weeds such as monochoria and toothcup. Broad-leaved weeds in plowed land can be killed without causing phytotoxicity to crops such as wheat or corn. PREPARATION:The compound of formula I can be produced e.g. by reacting a nicotinic acid anilide derivative of formula II (Y is halogen) with 3- trifluoromethylphenol of formula III in a solvent (e.g. benzene) in the presence of a base (e.g. sodium hydroxide or triethylamine) as an acid scavenger. As an alternative method, the compound of formula I is produced by reacting an aniline derivative of formula IV with the compound of formula V.

Description

DETAILED DESCRIPTION OF THE INVENTION Field of Industrial Application The present invention relates to a novel nicotinic acid anilide compound and a herbicide containing the compound as an active ingredient.

BACKGROUND OF THE INVENTION PRIOR ART AND PROBLEMS THEREOF Japanese Patent Application Laid-Open No. 57-118568 describes that certain nicotinic acid amide compounds can be used as active ingredients of herbicides. However, the herbicidal action of the compounds described in this publication is not necessarily satisfactory in terms of selectivity between useful crops and broad-leaved weeds.

An object of the present invention is to provide a selective herbicide that facilitates the control of broad-leaved weeds in areas where these crops are cultivated, without having the same harmful effect on grains such as rice and wheat.

Means for Solving the Problems As a result of extensive research to achieve the above object, the present inventors have found that the present invention provides a nicotinic acid anilide compound represented by the following general formula (I) that has not been described in any literature. It was discovered that the objectives of the period could be achieved. That is, the present invention is based on the general formula (a) [wherein X represents a methyl group or a halogen atom]. ] The present invention relates to a nicotinic acid anilide compound represented by the following, and a herbicide containing the compound as an active ingredient.

The compound of the present invention represented by the above general formula (I) is a novel compound characterized in that it is a 2,3-disubstituted anilide having a methyl group at the 2-position and a halogen atom at the 3-position,
For example, it can be easily produced by the method shown in (a) or (b) below.

[In the formula, X is the same as above. Y represents )\rogen atom. The compound of general formula (I) is produced by reacting the nicotinic acid anilide derivative represented by () with 3-trifluoromethylphenol represented by the formula.

This reaction can be carried out using hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, ethers such as tetrahydrofuran and dioxane, alcohols such as methanol and ethanol, acetone, methyl ethyl ketone, etc. Ketone series, other organic solvents such as acetic acid ethyl ester, acetonitrile, dimethylformamide, dimethyl sulfoxide, or water, or an appropriate mixed solvent thereof, with sodium hydroxide, potassium carbonate, hydrogenation as a deoxidizing agent. This can be easily carried out at room temperature in the presence of an inorganic base such as sodium, or an organic base such as triethylamine, pyridine, sodium methylate, etc., or by heating if necessary.

(b) General formula [wherein, X is the same as above. ] Aniline derivatives represented by the formula and 2-(3-trifluoromethylphenoxy) represented by the formula
The compound of the present invention is produced by reacting with nicotinic acid chloride. This reaction uses hydrocarbons such as benzene and toluene, halogenated hydrocarbons such as dichloromethane and 1,2-dichloroethane, tetrahydrofuran,
A deoxidizing agent in an ether type such as dioxane, a ketone type such as acetone, methyl ethyl ketone, other organic solvents such as ethyl acetate, acetonitrile, dimethyl formamide, dimethyl sulfoxide, water, or an appropriate mixed solvent thereof. The reaction can be easily carried out at room temperature in the presence of an inorganic base such as sodium hydroxide or potassium carbonate, or an organic base such as triethylamine or pyridine, or under heating or cooling as required.

The compound of the present invention thus obtained can be easily isolated and purified from the reaction mixture by conventional separation and purification means.

The compound of the present invention represented by the above general formula (I) causes almost no phytotoxicity to rice in paddy fields, and is effective in selectively weeding broad-leaved weeds such as Prunus japonicus and Prunus japonicus at a low dose. It is also useful for weeding broad-leaved weeds in fields without causing chemical damage to grains such as wheat and corn. The compounds of the present invention can also be used as herbicides in orchards and non-agricultural lands.

The timing of its use can be selected as appropriate, such as before sowing, at the time of sowing, at the time of transplanting, at the time of young seedlings, during the growing season, etc., and the method of use can be appropriately selected from water surface treatment, soil treatment, foliage treatment, etc. .

When actually using the compounds of the present invention, solids commonly used in the preparation of agricultural chemicals, so that they can be used more conveniently,
Mixed with various liquid carriers to form wettable powders, emulsions, oils, powders,
It can be manufactured into granules, flowables, etc. Furthermore,
Auxiliary agents such as dispersants, diluents, emulsifiers, spreading agents, wetting agents, adsorbents, thickeners, antifoaming agents, and antifreeze agents can also be added to the drug.

The carrier referred to herein may be either solid or liquid, or a combination thereof. A typical example is
Talc, clay, bentonite, kaolin, diatom, calcium carbonate, charcoal, starch, gum arabic, water, alcohol, kerosene, naphtha, xylene, cyclohexane,
Examples include methylnaphthalene, benzene, acetone, dimethylformamide, glycol ether, and N-methylpyrrolidone.

Examples of adjuvants include polyoxyethylene alkylphenyl ether, polyoxyethylene sorbitan monooleate, ethylene oxypropylene oxide copolymer, lignin sulfonate, sorbitan ester, soaps, sulfated oils, alkyl sulfate ester salts, Petroleum sulfonates, dioctyl sulfosuccinate salts, alkylbenzene sulfonic acids, aliphatic amine salts, quaternary ammonium salts, alkylpyridinium salts, alkyl dimethyl betaines, alkylaminoethyl glycine, polyglycol sulfate esters, alkyl amine sulfonic acids,
Isopropyl phosphate, carboxymethyl cellulose, polyvinyl alcohol, hydroxypropyl cellulose,
Examples include xanthan gum.

In formulation, the mixing ratio of the compound of the present invention can generally be freely selected within the range of 0.05 to 95% by weight, but preferably 0.5 to 50%. Contains a carrier of 40 to 99%, preferably 40 to 90%
, formulations containing 0 to 20%, preferably 1 to 7% of adjuvants are preferred.

In addition, by mixing with other fungicides, herbicides, plant growth agents, insecticides, acaricides, and other agricultural chemicals and fertilizers,
A wider range of effects can be expected.

When actually using the compound of the present invention, it goes without saying that the amount used should be selected appropriately depending on the time of use, weather conditions, method of use, dosage form, place of use, target weeds, target crops, etc. The dosage for the compound of the present invention is generally 0.0. The amount is about 1 to 500 g, preferably about 1 to 50 g per 10 ares.

EXAMPLES Hereinafter, Examples, Test Examples, and Formulation Examples will be given to further clarify the present invention.

Example 1 (a) Preparation of N-(2-methyl-3-chlorophenyl)-2-(3-trifluoromethylphenoxy)nicotinamide [Compound No. (2)] 2 g of 3-'ylorophenyl) nicotinamide and 5 g of 3-trifluoromethylphenol
8% sodium methylate was added to 2.2 g of methanol solution, then the methanol was distilled off and the residue was
It was heated at 81 to 190°C for 2 hours and 30 minutes. After cooling, the reaction mixture was dissolved in 100 me of methylene chloride and washed twice with 50 g of 8% sodium hydroxide solution. This methylene chloride solution was dried over anhydrous sodium sulfate, and under reduced pressure (2
The mixture was evaporated to dryness at 0 mmHg) to obtain 2.2 g of evaporated to dryness.

This evaporated product was recrystallized from a mixed solvent of 45 parts of n-hexane and 20 parts of toluene to produce N-(2-methyl-3-chlorophenyl)-2-(3-trifluoromethylphenoxy)nicotinamide 1. 2 g was obtained as white crystals.

Melting point 158-159°C Example 2 Preparation of N-(2-methyl-3-chlorophenyl)-2-(3-trifluoromethylphenoxy)nicotinamide [Compound No. (2)] by method (b) 2-(3) 4 g of nicotinic acid chloride was dissolved in 30'w2 of toluene, 2.8 g of triethylamine and 2.0 g of 2-amino-6-chlorotoluene were added, and the mixture was heated at 80-85°C for 6 hours. .

After cooling, the reaction solution was evaporated to dryness under reduced pressure (20 mmHg). The residue was ground with 50 ml of water, extracted with 2 x 50 ml of methylene chloride, and the methylene chloride extract was mixed with 50 ml of water.
e, dried over anhydrous sodium sulfate, and dried under reduced pressure (2
The mixture was evaporated to dryness at 0 mmHg) to obtain 5.0 g of evaporated to dryness. This evaporated dry product was mixed with 90 g of n-hexane and 40 g of toluene.
N-(2-methyl-3-
chlorophenyl)-2-(3-trifluoromethylphenoxy)nicotinamide4. Obtained Og.

In the same manner, the compounds shown in Table 1 below were produced.

Table 1 Test Example 1 A 115,000 are Wagnerbot was filled with paddy soil (clay loam), water was added and plowed, and seeds of Japanese millet, Japanese cabbage, broad-leaved weeds (Azaena, Apsyllium, Kikashigusa, Chickweed), and Firefly were sown. Then, three rice plants at the two-leaf stage were planted at a depth of 2 cm.

The drug treatment was carried out by manually scattering a predetermined amount of granules obtained in accordance with Formulation Example 1 described later on the water surface at the time of germination of Japanese millet. The plants were managed and grown in a greenhouse, and the herbicidal effect and chemical damage to rice were investigated 4 weeks after the chemical treatment. The results are shown in Table 2.

In addition, the numerical values in the table indicate the herbicidal effect and the chemical damage to rice, and the specific values are as follows.

Numerical weeding effect Crop damage 5 Weed suppression rate 90% or more Death (almost complete death) 4 Weed suppression rate 70-89% Severe damage 3 Weed suppression rate 4
0-69% Medium Harm 2 Weed suppression rate 20-39%
Slight damage 1 Weed suppression rate 6-19% Slight damage 0
Weed suppression rate 5% or less Harmless (almost no effect) In addition, the following were used as control compounds for comparison.

Comparative compound A: Compound C1 described in JP-A No. 57-118568 Comparative compound B: Compound described in JP-A-57-118568 Melting point 128-129°C Mass spectrometry (m/e) 406 (M"' ), 266 (Base Beak) Comparative Compound C: Compound manufactured as a comparative drug Test Example 2 Field soil (clay loam) was filled in a 115,000 are Wagner pot, wheat seeds were sown, and seeds of crabgrass, snail grass, and white loam were sown. The soil was covered to a depth of 2 cm with field soil containing the soil. Immediately thereafter, a predetermined amount of the emulsion obtained according to Formulation Example 3 below was weighed, diluted with 5 yoke of water per pot, and sprayed using a small sprayer. It was sprayed on the soil surface. Management and cultivation were carried out in a greenhouse. Four weeks after the chemical treatment, the herbicidal effect and phytotoxicity of wheat were investigated. The results are shown in Table 3.

The numerical values in the table are the same as those shown in Test Example 1.

Next, formulation examples of the herbicide of the present invention will be shown.

Formulation Example 1 Granule Test Example 3 A 115,000 are Wagner pot was filled with field soil (clay loam), and wheat and radish seeds were sown.
The seedlings were covered with soil to a depth of 100 ml and grown in a greenhouse for 10 days. after that,
A predetermined amount of the wettable powder obtained according to Formulation Example 2 described later was diluted with water containing a spreading agent equivalent to 10 liters per are, and the foliage was treated from above the plant using a small sprayer. Growth management was carried out in a greenhouse, and the herbicidal effect and chemical damage to wheat were investigated 4 weeks after the chemical treatment. The results are shown in Table 4. The numerical values in the table are the same as those shown in Test Example 1.

Compound No. 2 0.3 parts by weight Sodium ligninsulfonate 2 Bentonite
30 Talc
67.7 Mix these ingredients well until homogeneous and granulate to obtain granules.

Formulation Example 2 Wettable Powder Compound No. 2 10 parts by weight Sodium alkyl sulfate 2.5 Polyoxyethylene alkyl 2.5 Phenyl ether clay 85 Mix these ingredients well until homogeneous, pulverize and hydrate get the agent.

Formulation Example 3 Emulsion Compound No. 3 10 parts by weight Alkylbenzene sulfonate 3 Polyoxyethylene alkyl 10 Aryl ether Quidylol 77 parts by weight These components are thoroughly mixed until uniform and dissolved to obtain an emulsion.

(Hereafter Up)

Claims (2)

[Claims] (1) General formula ▲Contains mathematical formulas, chemical formulas, tables, etc.▼ [In the formula, X represents a methyl group or a halogen atom. ] A nicotinic acid anilide compound represented by (2) A herbicide containing the nicotinic acid anilide compound according to claim 1 as an active ingredient.