JP2547027B2 - Cyclohexane derivative and herbicide containing it as an active ingredient - Google Patents

Description

TECHNICAL FIELD The present invention relates to a novel cyclohexane derivative and a herbicide containing the same as an active ingredient.

<Prior Art> Up to now, JP-A-54-46749 and JP-A-54-115349.
It is described in the publications and the like that a cyclohexane derivative can be used as an active ingredient of a herbicide.

<Problems to be Solved by the Invention> However, these compounds are not necessarily satisfactory because of insufficient herbicidal activity and poor selectivity between crops and weeds.

<Means for Solving Problems> In view of such a situation, the present inventors have conducted various studies in order to develop a compound having excellent herbicidal activity, and as a result, have found that it has excellent herbicidal activity at a low dose. In addition, the present invention has been accomplished by finding a compound that does not show phytotoxicity to crops.

That is, the present invention has the general formula [I] [In the formula, R ¹ represents a hydrogen atom, an alkyl group or an alkoxymethyl group, and R ² represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkylmethyl group, a haloalkenyl group, a cyanoalkyl) group, an alkylthiomethyl group, an alkoxy group. It represents a methyl group or a benzyl group, and R ³ represents a hydrogen atom or a methyl group.

However, the case where R ¹ is a methyl group, R ² is an ethyl group and R ³ is a hydrogen atom is excluded. ] A cyclohexane derivative represented by the following (hereinafter referred to as the compound of the present invention), a salt thereof, and a herbicide containing the same as an active ingredient are provided.

 Next, a method for producing the compound of the present invention will be described.

The compound of the present invention has the general formula [II] [In the formula, R ¹ and R ³ have the same meanings as described above. ] And an acylcyclohexane derivative represented by the general formula [II
I] NH ₂ OR ² [III] [In the formula, R ² has the same meaning as described above. ] It can manufacture by reacting with the hydroxylamine shown by these or its inorganic acid salt.

This reaction is usually carried out without solvent or in a solvent, if necessary in the presence of a base, and the reaction temperature range is 0 to 100 ° C.
The reaction time range is 0.5 to 24 hours, and the amount of the reagent to be used in the reaction is 1 to 2 equivalents of hydroxylamine [III] or its inorganic acid salt with respect to 1 equivalent of acylcyclohexane derivative [II]. The base is 1-2 equivalents.

Examples of the solvent include aliphatic hydrocarbons such as hexane, heptane, ligroin and petroleum ether, aromatic hydrocarbons such as benzene, toluene and xylene, halogenated carbonization such as chloroform, carbon tetrachloride, dichloroethane, chloropentene and dichlorobenzene. Ethers such as hydrogen, diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, isopropanol, t-butanol, octanol, cyclohexanol, methyl cellosolve, diethylene glycol, glycerin, ethyl formate, acetic acid Esters such as ethyl, butyl acetate, diethyl carbonate, nitroethane,
Nitrides such as nitrobenzene, acetonitrile, nitriles such as isobutyronitrile, pyridine, triethylamine, N, N-diethylaniline, tributylamine,
Examples thereof include tertiary amines such as N-methylmorpholine, acid amides such as formamide, N, N-dimethylformamide and acetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, water and the like, or a mixture thereof.

As the base, pyridine, triethylamine, N, N-
Examples thereof include organic bases such as diethylaniline, inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate and sodium hydride, and alkali metal alkoxides such as sodium methoxide sodium ethoxide.

After completion of the reaction, the reaction solution is poured into water, made neutral to acidic, and then subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, purification by operations such as chromatography, distillation and recrystallization. By doing so, the desired compound of the present invention can be obtained.

The compound of the present invention represented by the general formula [I] may have the following tautomeric structure.

Similarly, the acylcyclohexane derivative represented by the general formula [II] is considered to have the following tautomeric structure.

[In the formula, Z is Represents Next, Table 1 shows the compounds of the present invention produced by this production method.

The compound of the present invention forms salts such as metal salts and ammonium salts, and these salts also have herbicidal effect.

Examples of the metal salt include potassium salt, sodium salt, lithium salt, calcium salt, copper salt, magnesium salt, and the like.These salts include the compound of the present invention in a solvent such as water, acetone, alcohol, potassium hydroxide or water. By reacting with sodium oxide by heating, if necessary, to lead to potassium salt or sodium salt, and further reacting the obtained potassium salt or sodium salt with chloride, hydroxide, sulfate, nitrate, etc. of other metals. Obtainable.

Further, the compound of the present invention can be converted to an ammonium salt by reacting the compound of the present invention with a quaternary ammonium hydroxide in a solvent such as water, acetone or alcohol. Examples of ammonium salts include tetrapropylammonium salt, benzyltrimethylammonium salt and the like.

The acylcyclohexanone derivative represented by the general formula [II], which is a starting compound for producing the compound of the present invention, is produced by, for example, a series of reactions shown below.

[In the formula, R ₁ and R ³ have the same meanings as described above. The compound represented by the formula [IV] is obtained by reacting 4-trifluoromethylthiophenol and acrolein in the presence of a catalytic amount of triethylamine in a solvent such as tetrahydrofuran, diethyl ether, toluene, benzene or chloroform at 0 ° C.
~ It can be produced by reacting at room temperature.

The compound represented by the formula [V] can be obtained by reacting the compound represented by the formula [IV] with 1-triphenylphosphoranylidene-2-propanone in a solvent such as chloroform.

The compound represented by the general formula [VII] is produced by heating the compound represented by the formula [V] in a solvent in the presence of a diester of malonic acid or methylmalonic acid and a metal alkoxide. As the solvent alcohol or alcohol and tetrahydrofuran, dioxane, toluene,
A mixed solvent with benzene or the like is used.

The compound represented by the general formula [VIII] is represented by the general formula [VII]
A compound represented by sodium hydroxide, potassium hydroxide, sodium carbonate, alkaline water such as potassium carbonate,
It can be obtained by hydrolysis followed by decarboxylation.

The compound represented by the general formula [IX] is obtained by converting the compound represented by the general formula [VIII] into an acid halide in the presence of a base in an inert solvent such as tetrahydrofuran, diethyl ether, benzene, toluene, chloroform, dichloromethane and acetonitrile. It can be obtained by reacting.

The compound represented by the general formula [II] is produced by heating the compound represented by the general formula [IX] in a solvent such as acetonitrile in the presence of a catalyst such as 4-dimethylaminopyridine for several hours.

The compound of the present invention, in the foliage treatment and soil treatment of upland fields, various weeds that are problematic, for example, purslane, chickweed, white azalea, Aogatetow, Japanese radish, strawberries, stag deer, dog physalis, etc. It has herbicidal activity against grass weeds such as Echinococcus, Mejiba, Astragalus chinensis, Astragalus chinensis, Oat, Oat grass, Seiban sorghum, and Echinacea, and the compound of the present invention is corn, wheat, rice, soybean, cotton, sugar beet, etc. It does not show any harmful effects on major crops of

Further, the compound of the present invention, in the flooding treatment of paddy fields, various weeds that are problematic, for example, grass weeds such as Tainubie, azena, broad-leaved weeds such as Mizohakobe, and the like have a herbicidal effect, and moreover, to rice. On the other hand, it does not show any serious phytotoxicity.

Further, the compound of the present invention can be used as a herbicide for paddy fields, fields, orchards, pastures, lawns, forests, non-agricultural lands, and the like. It can be expected to increase potency. Furthermore, it can be used by mixing with insecticides, acaricides, nematicides, plant growth regulators, fertilizers, soil conditioners and the like.

When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant and other auxiliary agents for formulation to prepare an emulsion, a wettable powder, a suspension, a granule or the like. To use.

These preparations contain the compound of the present invention as an active ingredient in a weight ratio of 0.1 to 90%, preferably 0.2 to 80%.

Examples of the solid carrier include kaolin clay, attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, calcite, walnut powder, urea, ammonium sulfate, fine powder or particles of synthetic hydrous silicon oxide, and the like. As the liquid carrier, xylene, aromatic hydrocarbons such as methylnaphthalene, alcohols such as isopropanol, ethylene glycol, cellosolve, acetone, cyclohexanone, ketones such as isophorone, soybean oil, vegetable oil such as cottonseed oil, dimethyl sulfoxide, N , N
-Dimethylformamide, acetonitrile, water and the like.

Surfactants used for emulsification, dispersion, wet spreading, etc. include alkyl sulfates, alkyl sulfonates, alkyl aryl sulfonates, dialkyl sulfosuccinates, polyoxyethylene alkyl aryl ether phosphates, and the like. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkyl aryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, and polyoxyethylene sorbitan fatty acid esters. .

Other auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol, gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like.

The compound of the present invention is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or after emergence of weeds. The soil treatment includes a soil surface treatment and a soil admixture treatment. The foliage treatment includes a treatment from above a plant body and a local treatment for treating only weeds so as not to adhere to crops.

When the compound of the present invention is used as an active ingredient of a herbicide,
The amount of treatment depends on weather conditions, formulation form, treatment time, method,
Depending on the location, target weed, target crop, etc., it is usually 0.05 g to 200 g per are, preferably 0.1 g to 100 g.
Emulsions, wettable powders, suspending agents, etc. are usually prepared by diluting a predetermined amount thereof with 1 liter to 10 liters of water per 1 are (to which an auxiliary such as a spreading agent is added if necessary). After the treatment, the granules and the like are usually treated without any dilution.

Examples of the spreading agent include polyoxyethylene resin acid (ester), ligninsulfonic acid salt, abietic acid salt, dinaphthylmethanedisulfonic acid salt, and paraffin in addition to the above-mentioned surfactant.

<Example> Hereinafter, the present invention will be described with reference to manufacturing agents, formulation examples and test examples.
Although described in more detail, the present invention is not limited to these examples.

 First, production examples of the compound of the present invention will be shown.

Production Example 1 (Production of Compound (34) of the Present Invention) 2-propionyl-5- [2- (4-trifluoromethylphenylthio) ethyl] cyclohexane-1,3-dione (0.19 g) was dissolved in ethanol (5 ml) to give allyloxy. Amine hydrochloride (0.07 g) and triethylamine (0.06 g) were added, and the mixture was stirred overnight at room temperature. The reaction solution was poured into water, acidified with hydrochloric acid and then extracted with chloroform. After removing chloroform, the residue was purified by thin layer chromatography (developing solvent hexane: ethyl acetate = 5: 1), and 2- (1-allyloxyaminopropylidene) -5- [2- (4-triethyl Fluoromethylphenylthio) ethyl] cyclohexane-1,3-dione (0.13 g) was obtained.

▲ n ^19.5 _D ▼ 1.5399 ¹ H-NMR spectrum (CDCl ₃ ) δ value (ppm) 14.63 (1H, s), 7.46 (4H, ABq), 6.35 to 5.
71 (1H, m), 5.45 (2H, bd), 5.23 (1H, m), 4.54 (2H, m)
d), 3.0 to 1.5 (9H, m), 1.14 (3H, t), 3.01 (2H, t) Production Example 2 (Production of compound (19) of the present invention) 2-acetyl-5- [2- (4- Trifluoromethylphenylthio) ethyl] -4-methylcyclohexane-
0.23 g of 1,3-dione and 0.08 g of ethoxyamine hydrochloride were dissolved in 5 ml of ethanol, and 0.07 g of triethylamine was added,
Stir for 10 hours at room temperature. Water was added to the reaction solution, acidified with hydrochloric acid, and extracted with chloroform. After removing chloroform, the residue was purified by thin layer chromatography (developing solvent hexane: ethyl acetate = 5: 1), and 2- (1-ethoxyaminoethylidene) -5- [2- (4-trifluoromethyl) Phenylthio) ethyl] -4-methylcyclohexane-1,3-dione (0.15 g) was obtained.

▲ n ²³ _D ▼ 1.5181 ¹ H-NMR spectrum (CDCl ₃ ) δ value 15-14 (1H, br), 7.44 (4H, ABq), 4.11 (2H,
q), 3.00 (2H, t), 2.36 (3H, s) 1.28 (6H, t, d), 2.8
~ 1.5 (6H, m) Next, Table 2 shows some of the compounds of the present invention produced in the same manner as above.

Next, a production example of a raw material compound for producing the compound of the present invention will be shown as a reference example.

Reference Example 1 (Production Example of Compound Represented by General Formula [VII]) 0.81 g of metallic sodium was dissolved in 10 ml of methanol, and 100 ml of tetrahydrofuran was added. Then, 6.39 g of diethyl methylmalonate was added, and the mixture was heated under reflux for 15 minutes.
Stop heating, add 6- (4-trifluoromethylphenylthio) -3-hexen-2-one (9.17 g) dropwise, and add again 45
Heated to reflux for minutes. Tetrahydrofuran was removed, water was added to the residue and the mixture was extracted with diethyl ether to remove impurities, then the aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The solvent was removed to remove 4-methoxycarbonyl-4-methyl-5.
9.2 g of-[2- (4-trifluoromethylphenylthio) ethyl] cyclohexane-1,3-dione was obtained. ¹ H-NMR spectrum (CDCl ₃ + DMSO-d ₆ ) δ value (ppm) 7.45 (4H, ABq), 5.41 (1H, s), 4.01 (3H,
s), 3.01 (2H, t), 2.5 to 1.5 (6H, m), 1.12 (3H, d) Reference Example 2 (Method for producing compound represented by general formula [VIII]) 3.5 g of potassium hydroxide in 50 ml of water It was then dissolved in, and to this was added 4-methoxycarbonyl-4-methyl-5- [2- (4-trifluoromethylphenylthio) ethyl] cyclohexane-1,3-dione (9.5 g), and the mixture was heated under reflux for 1.5 hours. After cooling, impurities were removed by adding diethyl ether for extraction, and then the aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The solvent was removed to remove 4-methyl-5- [2-
5.2 g of (4-trifluoromethylphenylthio) ethyl] cyclohexane-1,3-dione were obtained. ¹ H-NMR spectrum (CDCl ₃ + DMSO-d ₆ ) δ value (ppm) 7.43 (4H, ABq), 5.31 (1H, s), 2.95 (2H,
t), 2.5 to 1.5 (6H, m), 1.15 (3H, d) Reference Example 3 (Production example of compound represented by general formula [IX]) 5- [2- (4-trifluoromethylphenylthio)
1.58 g of ethyl] cyclohexane-1,3-dione was dissolved in 10 ml of tetrahydrofuran, 0.53 g of triethylamine and 0.51 g of propionyl chloride were added, and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into water and extracted with ether. The ether layer was washed successively with diluted hydrochloric acid, aqueous sodium hydrogen carbonate and water to remove the solvent, and 1.73 g of 1-propionyloxy-5- [2- (4
-Trifluoromethylphenylthio) ethyl] -1-cyclohexen-3-one was obtained. ¹ H-NMR spectrum (CDCl ₃ ) δ value (ppm) 7.41 (4H, ABq), 5.91 (1H, s), 3.03 (2H,
t), 2.98 (2H, q), 2.5 to 1.5 (7H, m), 1.31 (3H, t) Some of the compounds represented by the general formula [IX] produced in the same manner as above are shown in Table 3. Show.

Reference Example 4 (Production example of compound represented by general formula [II]) 8.3 g of 1-acetoxy-5- [2- (4-trifluoromethylphenylthio) ethyl] -cyclohexene-3
-One and 0.8 g of 4-dimethylaminopyridine were dissolved in 15 ml of acetonitrile and heated under reflux for 2.5 hours. The reaction solution was poured into water, acidified with hydrochloric acid and extracted with ethyl acetate.
The solvent was removed and 3.3 g of 2-acetyl-5- [2- (4-
Trifluoromethylphenylthio) ethyl] cyclohexane-1,3-dione was obtained. ¹ H-NMR spectrum (CDCl ₃ ) δ value (ppm) 18.16 (1H, s), 7.46 (4H, ABq), 3.03 (2
H, t), 2.58 (3H, s) 2.8 to 1.6 (7H, m), and Table 4 shows some of the compounds represented by the general formula [II] produced in the same manner as above.

Formulation examples are shown below. The compounds of the present invention are shown by the compound numbers in Table 2. Parts are parts by weight.

Formulation Example 1 50 parts of the present compound (30), 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain a wettable powder.

Formulation Example 2 10 parts of the present compound (31), 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate, 30 parts of xylene and 40 parts of cyclohexanone are mixed well to obtain an emulsion.

Formulation Example 3 2 parts of the present compound (43), 1 part of synthetic hydrous silicon oxide,
2 parts of calcium lignin sulfonate, 30 parts of bentonite and 65 parts of kaolin clay are well pulverized and mixed, water is added and further kneaded, and then granulated and dried to obtain granules.

Formulation Example 4 25 parts of the present compound (41), 3 parts of polyoxyethylene sorbitan monooleate, 3 parts of CMC, and 69 parts of water are mixed,
The suspension is obtained by wet grinding until the particle size is below 5 microns.

Next, Test Examples will show that the compound of the present invention is useful as an active ingredient of a herbicide. The compound of the present invention is
The compound number shown in the table is the compound used for comparison and control.
It is shown by the compound symbol in the table.

The herbicidal effect is "0" when the germination and the growth inhibition of the test plant at the time of the survey are visually observed and there is no or almost no difference from the case where the compound is not tested,
The test plant in which the death or growth was completely inhibited was evaluated as "5" and evaluated in 6 levels of 0 to 5, 0, 1,
Shown by 2, 3, 4, and 5.

Test Example 1 Field soil treatment test Field soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and then, roots and oats were sown and covered with soil. The test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount was 1
The mixture was diluted with 10 liters of water per are and applied to the soil surface with a small atomizer. Grow in a greenhouse for 20 days after treatment,
The herbicidal efficacy was investigated. The results are shown in Table 6.

Test Example 2 Field and foliage treatment test Field soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and roots and oats were sown and grown in a greenhouse for 10 days. Then, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the compound was diluted with water containing 10 liters of spreading agent per are, and the leaves were treated from above the plant with a small sprayer. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 7.

Test Example 3 Field foliage treatment test Field soil was packed in a cylindrical plastic pot with a diameter of 10 cm and a depth of 10 cm, and Japanese radish and hornbill were sown.
Nurtured for days. Then, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount of the compound was diluted with water containing 10 liters of spreading agent per are, and the leaves were treated from above the plant with a small sprayer. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. Table 8 shows the results.

Test Example 4 Paddy Water Submersion Treatment Test Paddy soil was filled in a cylindrical plastic pot having a diameter of 8 cm and a depth of 12 cm, and Tainubie seeds were mixed to a depth of 1 to 2 cm. After flooding to make paddy fields, rice at the second leaf stage was further transplanted and grown in a greenhouse. Six days later (the initial stage of the development of each weed), the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount thereof was diluted with 5 ml of water and treated on the water surface. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 9.

Test Example 5 Field soil treatment test Field soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm, and soybean, cotton, dog millet, sorghum, and white foxtail were sown and covered with a thickness of 1 to 2 cm. According to Formulation Example 2, the test compound was made into an emulsion, and a predetermined amount thereof was diluted with water equivalent to 10 liters per are, and the soil surface was treated with a small sprayer. After treatment, the plants were grown in a greenhouse for 20 days, and the herbicidal efficacy was investigated. The results are shown in Table 10.

Test Example 6 Field Stem / Leaf Treatment Test Field soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm, and soybean, cotton, dog millet, crabgrass, sycamore sorghum, green croaker, oat, and grasshopper were cultivated for 18 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount thereof was diluted with 5 liters of water equivalent to 1 are containing a spreading agent, and uniformly sprayed from above the plant body over the entire foliage with a small sprayer. Processed. At this time, the growth conditions of weeds and crops differed depending on the grass species, but the cotyledon expansion to the 3-leaf stage and the plant height was 5 to 19 cm. Twenty days after the treatment, the herbicidal efficacy was investigated. The results are shown in Table 11. This test was conducted in a greenhouse throughout the entire period.

Test Example 7 Field and foliage treatment test A field vat having an area of 33 × 23 cm ² and a depth of 11 cm was filled with field soil, and soybean, cotton, honeygrass, syringa sorghum, Enocologsa, oat and Poa annua were sown.
Nurtured for days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the compound was spread per 10 are containing a spreading agent.
It was diluted with water equivalent to 1 liter, and the whole foliage was uniformly treated from above the plant with a small sprayer. At this time, the growth conditions of weeds and crops differed depending on the grass species, but the cotyledon expansion to the 3-leaf stage and the plant height was 5 to 19 cm. Twenty days after the treatment, the herbicidal efficacy was investigated. The results are shown in Table 12. This test was conducted in a greenhouse throughout the entire period.

Test Example 8 Field foliage treatment test A field vat having an area of 33 × 23 cm ² and a depth of 11 cm was filled with field soil, and corn, Inhibitor japonicus, Mejibushi, Seibanmokoshi, Enokurogusa, and oat were sown and cultivated for 18 days. Thereafter, the test compound was emulsified according to Formulation Example 2,
The predetermined amount was diluted with water equivalent to 10 liters per are, and the whole foliage was uniformly treated from above the plant with a small sprayer. At this time, the growth status of weeds and crops differed depending on the species of grass, but at the 1-2 leaf stage, the plant height was 7 to 15 cm. Twenty days after the treatment, the herbicidal efficacy was investigated. The result is the thirteenth
Shown in the table. This test was conducted in a greenhouse throughout the entire period.

Test Example 9 Paddy field flooding test 1 / 5000a Wagner pots were filled with paddy field soil, and seeds of Taenia nuvier were mixed to a depth of 1 to 2 cm. After being submerged into a paddy field, rice at the three leaf stage was transplanted and grown in a greenhouse. After 4 days, emulsify the test compound according to Formulation Example 2,
The predetermined amount was diluted with 10 ml of water and treated on the water surface to make the water depth 4 cm. After the treatment, the plants were grown in a greenhouse for 20 days and the herbicidal efficacy was investigated. The results are shown in Table 14. In addition, from the day after the treatment, water was leaked in an amount corresponding to a water depth of 3 cm per day for 2 days.

<Effects of the Invention> The compound of the present invention has an excellent herbicidal activity against various weeds which are problematic in soil treatment and foliage treatment of upland fields, and in flooding treatment of paddy fields, and between the main crops and weeds. Since it shows excellent selectivity, it can be used for various purposes as an active ingredient of a herbicide.

Claims (2)

(57) [Claims] 1. A general formula [In the formula, R ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a methoxymethyl group, and R ² represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, and 3 carbon atoms. ~ 4
Alkynyl group, (cycloalkyl having 3 to 6 carbon atoms) methyl group, haloalkenyl group having 3 carbon atoms, cyano (alkyl group having 1 to 3 carbon atoms) group, (alkylthio group having 1 to 3 carbon atoms) methyl group, ( It represents an alkoxy) methyl group having 1 to 3 carbon atoms or a benzyl group, and R ³ represents a hydrogen atom or a methyl group. However, R ¹ is a methyl group, R ² is an ethyl group and R ³
Except when is a hydrogen atom. ] The cyclohexane derivative and its salt shown by these. 2. General formula [In the formula, R ¹ represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms or a methoxymethyl group, and R ² represents an alkyl group having 1 to 12 carbon atoms, an alkenyl group having 3 to 4 carbon atoms, and 3 to 4 carbon atoms. 4 alkynyl group, (cycloalkyl having 3 to 6 carbon atoms) methyl group, haloalkenyl group having 3 carbon atoms, cyano (having 1 carbon atom)
~ 3 alkyl) group, (alkylthio having 1 to 3 carbon atoms)
It represents a methyl group, (alkoxy having 1 to 3 carbon atoms) methyl group or a benzyl group, and R ³ represents a hydrogen atom or a methyl group. However, the case where R ¹ is a methyl group, R ² is an ethyl group and R ³ is a hydrogen atom is excluded. ] A herbicide containing the cyclohexane derivative and its salt shown by these as an active ingredient.