KR820002292B1 - Process for the manufacture herbicidally active chloracetanilides - Google Patents

Abstract

Title compds. (I; R1,R2,R3 = H, C1-4 alkyl, halo, CF3; R4 = C1-6 alkyl; n = 1-3), useful as herbicide, were prepd. Thus 60.5g 2,6-dimethyl andiline and 68.50g (p-tolyl)-(l, 4, 7-trioxaoctyl)-sulphone in 100ml C6H4CH3 was heated for 20 hr to give N-(3,6-dioxaheptyl)-2,6-dimethylaniline(II). 13.82 g K2CO3 was added to 11.15 g II in 50 ml ethylacetate to give 12.23 g chloroacetate ≮N-(3,6-dioxaheptyl)-2,6-dimethyl anilide≉.

Description

Method for preparing chloroacet anilide effective as a herbicide

The present invention relates to a process for the preparation of novel chloroacet anilide of general formula (I), which is an effective compound as a herbicide.

In the above formula

R ₁ , R ₂ and R ₃ may be the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a torifluoromethyl group,

R ₄ represents an alkyl group having 1 to 6 carbon atoms,

n represents 1, 2 or 3.

Halogeno-acet anilide derivatives with herbicide action have already been known (see US Pat. No. 3,547,620). However, their range of action is extremely narrow and its action is highly dependent on soil.

Therefore, it has been required to develop herbicides that have a wide range of action and are irrelevant to soil.

This problem has been solved by the above general formula (I) compound.

Compounds of the present invention are characterized by extensive soil-herbicide action. It can be used to remove these sweet and dicotyledonous weeds.

Examples of weeds that can treat the present compounds by pre-germination methods include onions, eggplants, cineraria, metolicaria, brown vines, knotweed, shamrocks, gold films, digidalis, phaselias, rinses, green onions. , Ragweed, leek, fangs, poaful, ear of wheat, sparrow oats, lygras, timothy, orchardgrass and laver.

Generally 0.5 to 5 kg of active substance per hectare is used to remove weeds. It has also been demonstrated that the active compounds of the present invention act surprisingly selectively on useful crops such as, for example, cotton, peanut, rape, cabbage, cauliflower, soybean, pea, beet, spinach and lettuce. When two or more compounds of formula (I) are used in combination, the range of 0.5 to 5 kg per hectare is of course related to the total dosage of these compounds.

Another advantage of the active compounds of the invention is the fact that they also exhibit growth-regulatory action.

Other technically effective changes in plant growth caused by the compounds of the present invention include vertical growth inhibition, inhibition of muscle growth, growth of shoots or side branches, increased production of new pigments and improved storage capacity of plant components. Can be mentioned.

Accordingly, the present invention provides a herbicide composition consisting of the general formula (I) compound and an appropriate weighting agent. The herbicide composition may, of course, contain one or more compounds of general formula (I).

The present invention also provides a method of protecting a plant from weeds by treating the plant area with a general formula (I) compound.

The present invention also provides a method for treating crop areas with general formula (I) compounds to protect the crop areas from weeds.

The present invention also provides a method of controlling the growth of a plant by treating the plant with a compound of formula (I).

The present invention provides a pack comprising general formula (I) compounds and their use as herbicides and / or instructions for plant growth regulators.

The compounds of the present invention can be used alone or in mixtures thereof or with other active substances. If necessary, other plant protection agents or pesticides may be added, depending on the purpose of use.

If you want to extend the range of action, you can add other herbicides. As suitable co-components having herbicide effect, triazine, aminotriazole, anilide, diazine, uracil, aliphatic carboxylic acid and halogen-carboxylic acid, substituted benzoic acid and aryloxy-carboxylic acid, hydrazide, amide, nitrile, Examples include active substances belonging to esters of carboxylic acids, carbamic acid esters and thiocarbamic acid esters, urea, 1,3,6-trichlorobenzyl-oxypropanyl and thiocyanate-containing agents. Other additives include hydrating agents, emulsifiers, solvents, and the like, which have a synergistic effect on the action of herbicides and are straight on plants.

The active compounds of general formula (I) or mixtures thereof, together with surfactants such as liquids and / or solid excipients or diluents, if necessary, wetting agents, adhesives, emulsifiers and / or dispersants, may be used in powders, sprays, granules, liquids, It is advantageously used in the form of preparation compositions such as emulsions or suspending agents.

Examples of suitable liquid extenders are aliphatic hydrocarbons such as water, benzene, toluene and xylene, cyclohexanone, isophorone, dimethylsulfoxide and dimethylformamide, aromatic hydrocarbons, and mineral oil fractions.

As the solid extender, inorganic products such as tonsil, silica gel, talc, kaolin, attach clay, limestone and silicic acid and vegetable products such as meal are suitable.

Examples of the surfactant include calcium lignin sulfonate, polyoxyethylene alkylphenol ether, naphthalene sulfonic acid and salts thereof, phenol sulfonic acid and salts thereof, formaldehyde condensates, aliphatic alcohol sulfates and substituted benzene sulfonic acids and salts thereof.

The total content of one or more active substances in various herbicide compositions can vary widely.

For example, the composition may contain from about 5 to 95% by weight of active substance, from about 95 to 5% by weight of a liquid or solid extender and, if desired, also up to 20% by weight of surfactant.

The active substance can be used in conventional manner, for example in the case of spraying liquids with water as an extender in an amount of about 100 to 1000 liters per hectare. The active substance can also be applied by so-called low-dose and over-low-dose methods. It may be applied by the so-called low-dose method and the over-low-dose method, or may be applied in the form of so-called fine particles.

Examples of the substituents represented by R ₁ , R ₂ and R ₃ in formula (I) include methyl, ethyl, n-propyl, isopropyl, n-butyl secondary-butyl, isobutyl, tert-butyl, fluoro , Chloro, bromo, urethra and trifluoromethyl groups.

R ₄ may represent methyl, ethyl, propyl, isopropyl, secondary-butyl, isobutyl, tert-butyl, n-pentyl or n-hexyl group.

Among the compounds of the present invention, compounds which are distinguished by excellent effects are in particular the same as or different from R ₁ and R ₂ , each representing an alkyl group having 1 to 4 carbon atoms, R ₃ representing a hydrogen atom, and R ₄ representing 1 to 4 carbon atoms. N is a compound of formula (I) wherein n is 1 or 2.

Compounds of general formula (I), which have not been known so far, can be prepared, for example, by the process of the present invention described later.

In the general formula (I) compound of the present invention, the aniline of the general formula (II) is a compound of the general formula (III), preferably in a molar weight ratio of 2: 1 to 3: 1, wherein x represents a hydroxyl group. Under pressure, if necessary in the presence of water and a catalyst, preferably a nickel catalyst, and within 20 to 200 ° C. when x represents a halogen atom or a 4-CH ₃ -C ₆ H ₄ -SO ₂ -O- group. If necessary, the reaction is carried out using an inert solvent such as an organic solvent such as toluene or xylene to generate a compound of formula (IV), which is an organic base such as pyridine or tri-ethylamine, or sodium hydroxide, potassium hydroxide, sodium carbonate, Acid acceptors such as inorganic bases such as potassium carbonate or magnesium oxide and, if necessary, prepared by reacting with chloroacetyl chloride within -10 to 105 캜 in the presence of an organic solvent.

In the above formula

R ₁ , R ₂ , R ₃ , R ₄ and n are as described above,

x represents a hydroxyl group, a halogen atom or a 4-CH ₃ -C ₆ H ₄ -SO ₂ -O- group.

The final reaction product can be separated by known methods.

In the reaction of the product of general formula (IV) with chloroacetyl chloride, these reactants may be used in equimolar amounts, but it is preferable to use an excess of chloroacetyl chloride.

The compounds of the present invention are generally colorless, odorless, slightly fluid, easily soluble in polar organic solvents such as acetone, dimethylformamide and dimethyl sulfoxide, but insoluble in water and gasoline.

The following examples illustrate the invention.

Example 1 describes the preparation of the compound of the present invention,

Examples 2 and 3 illustrate possible uses and excellent functions of the compounds of the present invention.

Example 1

Chloroacetic acid [N- (3,6-dioxaheptyl) -2,6-dimethylanilide]

A solution of 60.50 g (0.5 mol) of 2,6-dimethylaniline and 68.50 g (0.25 mol) of (para-tolyl) -1,4,7-trioxoctyl) -sulfone in 100 ml of toluene was dissolved for 20 hours. During reflux. After cooling, water and 25 ml of sodium hydroxide solution are added, diluted with ethyl acetate, and the organic layer is separated. It is washed with water until it is almost neutral, dehydrated on magnesium sulphate, filtered and concentrated in vacuo.

The residue was vacuum distilled to yield N- (3,6-dioxaheptyl) -2,6-dimethylaniline having a boiling point of 119 to 131 ° C (0.4 Torr).

Yield: 32.44 g = 58.1% of theory

To 13.15 g (0.05 mole) N- (3,6-dioxaheptyl) -2,6-dimethylaniline solution in 50 ml of ethyl acetate is added 13.82 g (0.1 mole) of anhydrous potassium carbonate.

After the suspension is stirred, 11.29 g (0.1 mole) of chloro acetyl chloride is added dropwise at 25 to 30 DEG C while ice-cooling, and this is stirred for another hour. The mixture is allowed to stand at room temperature for several hours. Water is added and the mixture is shaken several times with ethyl acetate. The ethyl acetate layers were combined, dehydrated on magnesium sulfate, filtered and concentrated in vacuo.

Drying at room temperature and under high vacuum yields an almost colorless oil.

Yield: 12.23 g (81.6% of theory) of chloro acetic acid [N- (3,6-dioxaheptyl) -2,6-dimethylanilide].

The following compounds according to the invention can also be prepared in a similar manner.

Example 2

In a series of in-greenhouse tests performed on the compounds of the present invention listed in the following table, pre-germination methods were carried out at the rate of 3 kg of the active substance emulsified in 500 liters of water per hectare, each of which was tested as zombie and blood. Partial processing by After 3 weeks of treatment, the result is judged and graded from 0 to 4, with 0 indicating no effect and 4 indicating that the plant has been destroyed. As shown in the table, the test plants are destroyed by the compounds of the present invention.

Example 3

In a series of in-greenhouse tests performed on two soil types, the plants listed in the following table are sown and then treated before use, at a rate of 1 kg of active substance per hectare as a test compound. To this end, the test compound is sprayed evenly onto the plants in the form of an aqueous emulsion with in each case 500 liters of water per hectare. After three weeks of treatment, it can be seen that the compound of the present invention exhibits good selectivity and excellent herbicide effect in its action on weeds in conjunction with this minimum soil dependency. Compounds used for comparative purposes show only a much weaker effect on the test results, moreover, depending on the type of soil. The results are graded from 0, with 0 indicating that the plant is destroyed and 10 indicating that the plant has not suffered any damage.

0 = destruction of plants

10 = No damage.

Claims (1)

The reaction product of formula (IV), obtained by reacting aniline of formula (II) with a compound of formula (III), is reacted with chloroacetyl chloride in the presence of an acid acceptor. How to manufacture.

In the above formula R ₁ , R ₂ and R ₃ each represent a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, a halogen atom or a trifluoromethyl group, R ₄ represents an alkyl group having 1 to 6 carbon atoms n represents 1,2 or 3 X represents a hydroxyl group, a halogen atom or a 4-CH ₃ -C ₆ H ₄ -SO ₂ -O- group.