JPH0820554A - Cyclohexanedione derivative and herbicide - Google Patents

Abstract

PURPOSE:To obtain a new compound useful as a herbicide, especially exhibiting excellent herbicidal activity against a paddy field weed and upland field weed, free from damage against a useful crop, having little toxicity against human, animal and fish and having high safety. CONSTITUTION:This is a compound of formula I (R' is H or a lower alkyl; X is a lower alkyl, a lower alkenyl, a lower alkoxy, a lower alkyloxy, a halogen, a nitoro, etc.; n=0-2), e.g. 2-(2',4'-dichloro-3'-phnoxymetylbenzoyl)-1,3- cyclohexanedione. The compound of formula I is obtained by reacting a cyclohexanedione derivative of formula II with a benzoyl halide derivative of formula III (Y is a halogen) to obtain a compound of formula IV and subsequently reacting it with a cyanide source compound. The objective compound is useful for controlling a wide range of weeds such as a Gramineae weed, e.g. Echinochlora crus-galli, a broad leaf weed, e.g. Lindemia pyxidaria, Rotala indica and Elatine triandra, a Cyperaceae weed, e.g. Cyperus difformis, Scirpus juncoides, Eleocharis acicularis and Cyperus serotinus, Monochoria vaginalis and Sagittaria pygmaea.

Description

Detailed Description of the Invention

[0001]

[Object of the invention]

FIELD OF THE INVENTION The present invention relates to a novel cyclohexanedione derivative and a herbicide containing the derivative as an active ingredient.

Accordingly, the present invention is useful in the chemical industry as well as agriculture, especially in the agrochemical manufacturing industry.

[0003]

2. Description of the Related Art The compounds similar in chemical structure to the cyclohexanedione derivative of the present invention are described in the following documents.

In Japanese Patent Publication No. Hei 4-501726,
A compound represented by the following general formula is described, which is used as an active ingredient in an amount of 0.28 kg / ha against weeds such as sycamore, annual ryegrass, and oats.
It is described to be processed in. General formula

[Chemical 3]Where R Represents a chlorine atom or a bromine atom, R₁, R₂,
R₃Is a hydrogen atom or C 1-C 4 alkyl group, R_Four
Is a hydroxyl group, hydrogen atom or C 1-C 4 alkyl group is shown
Then R₁, R₂, R_FiveAnd R₆Is all C 1-C 4 Archi
R when R is₃And R_FourAre both carbonyl groups, R
_FiveIs a hydrogen atom or C 1-C 4 alkyl group, R₆Is
Hydrogen atom, C 1-C 4 alkyl group, C 1-C 4-alkyl
Thio group or C 1-C 4 alkylsulfonyl group is shown,
R ₇Represents a methyl group or an ethyl group, R₈Is a halogen source
X, oxygen atom or sulfur atom
Is shown.

US Pat. No. 5,092,919 describes compounds represented by the following general formula:
It is described that this is treated with 0.28 kg / ha as an active ingredient for weeds such as Astragalus chinensis, millet, and annual morning glory. General formula

[Chemical 4]Where R ₁~ R₃Is a hydrogen atom, C 1-C 4 alkyl groups
Show, R _FourIs a hydroxyl group, hydrogen atom, C 1-C Alkyl of 4
Group, etc. _FiveIs a hydrogen atom, C 1-C Alkyl of 4
Group, R₆Is a hydrogen atom, C 1-C 4 alkyl groups
Which shows R ₇Represents a methyl group or an ethyl group, R₈Is
Indicates a halogen atom, nitro group, etc.

US Pat. No. 5,110,979 describes herbicidal compounds represented by the following general formula. General formula

[Chemical 5]Where R ₁Is C 1-C 4 alkyl groups, C 1-C C of 4
Alkyl group, methoxyethyl group or ethoxyethyl
Group, R₇~ R₁₂Is a hydrogen atom or C1-C4
Represents a rutile group, Q is a halogen atom or a nitro group, etc.
Is shown.

[0007] PCT Patent Publication No. 92/19107 describes a method of enhancing the activity of a herbicidal compound by adding an auxiliary agent to the herbicidal compound represented by the following general formula. General formula

[Chemical 6]In the formula, R represents a halogen atom or the like, R₁, R₂, R₃,
R _Four, R_Five, R₆Is a hydrogen atom or C 1-C Alkyl of 2
Group, R₇, R₈Is a halogen atom, methoxyethyl group
Alternatively, it represents an ethoxyethyl group or the like.

[0008]

The compounds described in these documents (1) to (4) are not necessarily satisfactory because they have insufficient herbicidal efficacy or cause phytotoxicity to crops, as shown in the test examples below. It is hard to say kimono. Therefore, development of a herbicide without such a defect is desired.

The present invention is intended to provide a cyclohexanedione derivative having excellent herbicidal activity and safety against crops, and a herbicide for paddy rice and field crops containing the same, instead of these compounds.

[0010]

Means for Solving the Problems The present inventors have synthesized many cyclohexanedione derivatives in order to achieve the above-mentioned object, and have made earnest studies on their usefulness. As a result, the novel cyclohexanedione derivative represented by the following general formula (1) does not cause phytotoxicity to crops, and has excellent herbicidal effect with low dose on weeds of paddy rice and upland crops, especially main weeds of paddy field. Found to show.

Therefore, the gist of the first aspect of the present invention lies in the general formula (1)

[Chemical 7][Wherein, R¹ Represents a hydrogen atom or a lower alkyl group,
X is a lower alkyl group, a lower alkenyl group, a lower alkoxy group
Si group, lower alkynyloxy group, halogen atom, nitro
Group, trifluoromethyl group, -COR²Group (however, group
Medium, R²Is a lower alkyl group, a lower alkoxy group or a low
Represents a primary alkylamino group. ), -NHCOR³Group
But, Motochu, R³Is a lower alkyl group or lower alkyl
Represents an amino group. ), -S (O)_mR^FourGroup (however, group
Medium, R^FourRepresents a lower alkyl group, m represents 0 or 2.
You. ), -C (CH₃) = NOR^FiveGroup (however, in the group, R
^FiveRepresents a lower alkyl group. ) Or-(CH₂)_yCN
Represents a group (wherein y represents 0 or 1),
n represents 0, 1 or 2. ] Cyclohexa
It is in the Nedion derivative.

In the compound represented by the general formula (1),
The lower alkyl group, lower alkoxy group and lower alkylamino group have 1 to 4 carbon atoms and may be linear or branched, and include, for example, methyl group, ethyl group, n-propyl group and isopropyl group. , N-butyl group,
Examples thereof include isobutyl group, sec-butyl group, tert-butyl group, methoxy group, ethoxy group, n-propoxy group, isopropoxy group, methylamino group, dimethylamino group and ethylamino group. The lower alkenyl group and the lower alkylnyloxy group have 3 carbon atoms.
Or 4 and may be linear or branched, and for example, 2-propenyl group, 2-butenyl group, 1-
Methyl-2-propenyl group, 2-propynyloxy group,
1-methyl-2-propynyloxy group etc. are mentioned.

The gist of the second aspect of the present invention is a herbicide containing the compound of formula (1) as an active ingredient.

Next, typical examples of the compounds of the general formula (1) of the present invention are shown in Tables 1 to 3.

Compound No. Is also referred to in the following examples and test examples.

[0016]

[Table 1]

[0017]

[Table 2]

[0018]

[Table 3]

[0019]

The compound of the general formula (1) of the present invention is a novel compound. The compound of the general formula (1) acts as an active ingredient for controlling various weeds in paddy fields and upland fields.

[0020]

EXAMPLES (Production Method of the Compound of the Present Invention) Next, the production method of the compound of the present invention will be described in detail. That is, as the starting material, the general formula (2)

[Chemical 8](In the formula, R¹ Represents the above meaning. ) Cyclo
Hexanedione derivative and general formula (3)

[Chemical 9](In the formula, X , N represents the above meaning, and Y represents a halogen atom.
Represents ) With a benzoyl halide derivative
General formula (4)

Embedded image(In the formula, R¹, X And n have the above-mentioned meanings. )
Is obtained, and then reacted with a cyanide source as a catalyst.
General formula (1)

Embedded image(In the formula, R¹, X And n have the above-mentioned meanings. )
The compound of the present invention is obtained.

In the above reaction process, the step of reacting the compound of formula (2) with the compound of formula (3) to obtain the compound of formula (4) may be carried out as follows. That is, each of the compound of formula (2) and the compound of formula (3) is added in an equivalent amount, and the reaction is carried out in a suitable organic solvent in the presence of one equivalent or more of a dehydrohalogenating agent. The reaction is carried out by stirring these mixtures for 1 to 5 hours.

As the dehydrohalogenating agent, organic bases such as triethylamine, pyridine and N, N-diethylaniline, and inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate and sodium hydrogencarbonate can be used.

Examples of the solvent include hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, dichloromethane and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane, and ketones such as acetone and methyl ethyl ketone. , Acetonitrile and the like can be used.

After completion of the reaction, water may be added to the reaction solution and extracted with an organic solvent, which may be subjected to usual treatment such as concentration and, if necessary, purified by a procedure such as chromatography and recrystallization.

Next, the step of obtaining the compound of formula (1) of the present invention from the compound of formula (4) obtained by the above process, that is, the enol ester intermediate by a rearrangement reaction may be carried out as follows. That is, an excess (preferably about 2 equivalents) of base and a catalytic amount (preferably 0.
(01 to 0.1 equivalent) of a cyanide source is added and reacted in a suitable organic solvent. The reaction temperature is close to the boiling point of the solvent, preferably 20 to 40 ° C., and the reaction is carried out by stirring the mixture for a reaction time of 1 to 6 hours.

As the base, organic bases such as triethylamine, triethanolamine and pyridine, or inorganic bases such as potassium carbonate and trisodium phosphate can be used.

As the cyanide source, alkali metal cyanides such as sodium cyanide and potassium cyanide, cyanohydrins of methylalkylketones such as acetone cyanohydrin and methylisobutylketone cyanohydrin, or cyanohydrins of benzaldehyde, acetaldehyde cyanohydrin and propionaldehyde cyanohydrin can be used. Such aliphatic aldehydes such as cyanohydrin, zinc cyanide, and trimethylsilyl cyanide can be used.

As the solvent, hydrocarbons such as benzene, toluene and xylene, halogenated hydrocarbons such as chloroform, dichloromethane, 1,2-dichloroethane and chlorobenzene, ethers such as diethyl ether, tetrahydrofuran and dioxane, and acetone. , Ketones such as methyl ethyl ketone, acetonitrile, ethyl acetate, dimethylformamide and the like can be used.

After the completion of the reaction, water may be added to the reaction solution and the mixture may be extracted with an organic solvent, subjected to usual treatments such as concentration, and if necessary, purified by chromatography and recrystallization.

Examples of production by this method are shown in Examples 1 and 2.

The compound represented by the general formula (2), which is a starting material, is a known compound and can be obtained as a reagent. Further, the starting material of the general formula (3) is a novel compound, which can be synthesized according to a known method as shown in the following reaction formula, and its production example is shown in the reference production example.

[0032]

[Chemical 12] (X, Y and n have the same meanings as described above, and R represents an alkyl group having 1 to 4 carbon atoms.)

The step of reacting the compound of formula (5) with the compound of formula (6) to obtain the compound of formula (7) may be carried out as follows. That is, 1.0 equivalent of the compound of formula (6) is added to the compound of formula (5), and the mixture is reacted in a suitable organic solvent such as acetonitrile or dimethylformamide with stirring.

The reaction temperature is 10 to 100 ° C., preferably 2
It is performed in the range of 0 to 50 ° C.

The reaction time is 1 to 24 hours, preferably 1 to
Perform within a range of 5 hours. After completion of the reaction, water was added to the reaction mixture and extracted with an organic solvent such as toluene and chloroform,
The compound of formula (7) is obtained by concentrating it.

80% methanol / water (mixing ratio 80:20) was added to the compound of formula (7), and an alkali hydroxide such as sodium hydroxide was added in an amount of 1.5 equivalents to the compound of formula (7). The reaction is carried out by stirring at 10 to 60 ° C, preferably 1 to 5 hours.

Ether is added to this reaction solution, and the organic layer is extracted with an aqueous alkali hydroxide solution such as sodium hydroxide. The extract is acidified with hydrochloric acid and extracted with dichloromethane. The organic layer is dried over anhydrous sodium sulfate, and the solvent is distilled off under reduced pressure to obtain the compound of formula (8).

Dichloromethane was added to the compound of formula (8),
A few drops of a catalyst such as pyridine or dimethylformamide was added thereto, and then a suitable chlorinating agent such as thionyl chloride or oxalyl chloride was added to the compound of the formula (8) in an amount of 1.2.
The equivalent weight is added over 10 to 30 minutes.

Next, the solvent is distilled off from this solution to obtain the compound of formula (3).

The compound of formula (3) thus obtained may be reacted with the compound of formula (2) without isolation.

[0041]

【Example】

Example 1 Preparation of 2- (2 ', 4'-dichloro-3'-phenoxymethylbenzoyl) -1,3-cyclohexanedione (Compound No. 1) 1,3-Cyclohexanedione 6.1 g, triethylamine 6.6 g Then, 17.1 g of 2,4-dichloro-3-phenoxymethylbenzoyl chloride was added to a mixture of 70 ml of chloroform under ice cooling, and the mixture was stirred at room temperature for 1 hour. Then, the reaction solution was mixed with 5% hydrochloric acid aqueous solution and 5%.
% Aqueous sodium hydrogen carbonate solution, the chloroform layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product of this enol ester was dissolved in 70 ml of 1,2-dichloroethane, and 10.1 g (2 equivalents) of triethylamine and 0.3 g (0.07 equivalents) of acetone cyanohydrin were added thereto, and the mixture was added at 40 ° C. for 1 hour. It was stirred. After that, add 5%
It was washed with 70 ml of an aqueous hydrochloric acid solution, and the organic layer was dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel chromatography (eluent, toluene: acetone = 15: 1) to give 15.3 g of the title compound as white crystals (yield 72%, mp. 132). -134
C) was obtained.

Example 2 2- [3 '-(4 "-chlorophenoxymethyl)-
Production of 2 ', 4-dichlorobenzoyl] -1,3-cyclohexanedione (Compound No. 23) 3- (4'-chloro in a mixture of 6.1 g of 1,3-cyclohexanedione, 6.6 g of triethylamine and 70 ml of chloroform. Phenoxymethyl) -2,4-dichlorobenzoyl chloride (19.0 g) was added under ice cooling,
The mixture was stirred at room temperature for 30 minutes. Then, the reaction solution was mixed with a 5% hydrochloric acid aqueous solution and a 5% sodium hydrogencarbonate aqueous solution, respectively.
After washing with 0 ml, the chloroform layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The crude product of this enol ester was dissolved in 70 ml of acetonitrile, and 10.1 g (2 equivalents) of triethylamine and 0.3 g (0.07 equivalents) of acetone cyanohydrin were added thereto, and the mixture was stirred at room temperature for 1 hour. Then, concentrate the reaction solution under reduced pressure, add 70 ml of chloroform, and
% Aqueous hydrochloric acid solution (70 ml), and the chloroform layer was dried over anhydrous sodium sulfate. The solvent is distilled off under reduced pressure,
The residue was purified by silica gel chromatography (eluent, toluene: ethyl acetate = 15: 1) to give 18.5 g of the title compound as white crystals (yield 80%, mp 12).
1-123 ° C) was obtained.

Reference Production Example Production of 3- (4'-chlorophenoxymethyl) -2,4-dichlorobenzoyl chloride [Compound of the general formula (3)] 4-chlorophenol 14.0 g, potassium carbonate 1
Methyl-3-bromomethyl-2,4-dichlorobenzoate (30.0 g) was added to a mixture of 8.0 g and acetonitrile (150 ml), and the mixture was stirred at room temperature for 4 hours. After completion of the reaction, 300 ml of toluene was added to the reaction mixture, washed with water, and then the toluene was distilled off to give methyl-3-.
34.4 g (yield 99%) of (4'-chlorophenoxymethyl) -2,4-dichlorobenzoate was obtained as a pale yellow oil.

The above-obtained ester 15.0 g, 15
0 ml 80% methanol / water (mixing ratio, 80: 2
Sodium hydroxide (2.6 g) was added to the mixture of (0), the mixture was stirred at room temperature for 5 hours, 300 ml of ether was added to separate the layers, and the organic layer was extracted 3 times with 100 ml of 5% aqueous sodium hydroxide solution. This extract was combined with the previously separated aqueous layer and acidified with hydrochloric acid, and then extracted twice with dichloromethane. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and 3- (4'-chlorophenoxymethyl) -2,4-
13.7 g (yield 95%) of dichlorobenzoic acid was obtained as white crystals (mp 169.5 to 171 ° C.).

5 drops of dimethylformamide were added to a mixture of 9.9 g of the above product and 100 ml of dichloromethane, and 5.7 g of oxalyl chloride was slowly added. After the addition was completed, the solution was refluxed for 1 hour, and the solvent was evaporated under reduced pressure to obtain 10.3 g (yield 98%) of the title compound as a pale brown oily substance.

[0046]

Example (Method of formulating a herbicide) When the compound of the present invention is used as an active ingredient of a herbicide,
Usually, it is mixed with solid carrier, liquid carrier, surfactant, and other auxiliaries for preparations, and emulsions, wettable powders, liquids, flowable (sol) agents, powders, driftless agents, granules, and fine particles are prepared by a conventional formulation. It can be prepared in an appropriate form such as an agent or a tablet.

The carrier used here may be either solid or liquid, as long as it is commonly used for agricultural and horticultural chemicals, and is not limited to a particular carrier. For example, as these carriers, mineral powder (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica, vermiculite, gypsum, calcium carbonate,
Apatite, white carbon, slaked lime, silica sand, ammonium sulfate, urea, etc., vegetable powder (soybean flour, wheat flour, wood flour, tobacco powder, starch, crystalline cellulose, etc.), polymer compound (petroleum resin, polyvinyl chloride, Ketone resin, dammal gum, etc.), alumina, silicates, sugar polymers, highly dispersible silicic acid, waxes and the like. Further, as the liquid carrier, water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, iso-propyl alcohol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons (toluene,
Benzene, xylene, ethylbenzene, methylnaphthalene, etc., halogenated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, monochlorobenzene, trichlorofluoromethane, dichlorofluoromethane, etc.), ethers (ethyl ether, Ethylene oxide, dioxane, tetrahydrofuran, etc.),
Ketones (acetone, methyl ethyl ketone, cyclohexanone, methyl isobutyl ketone, isophorone, etc.),
Esters (ethyl acetate, butyl acetate, ethylene glycol acetate, amyl acetate, etc.), acid amides (dimethylformamide, dimethylacetamide, etc.), nitrites (acetonitrile, propionitrile, acrylonitrile, etc.), sulfoxides (dimethyl sulfoxide, etc.) , Alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.), aliphatic or alicyclic hydrocarbons (n-hexane, cyclohexane, etc.), industrial gasoline (petroleum ether, solvent naphtha, etc.), petroleum distillation Minerals (paraffins, kerosene, light oil, etc.) and the like.

In the preparation of emulsions, wettable powders, flowable agents, etc., various surfactants (or emulsifiers) are used for the purpose of emulsification, dispersion, solubilization, wetting, foaming, lubrication, spreading and the like. . Such surfactants include nonionic type (polyoxyethylene alkyl ether, polyoxyethylene alkyl ester, polyoxyethylene sorbitan alkyl ester, etc.), anionic type (alkylbenzene sulfonate, alkyl sulfosuccinate, alkyl sulfate, polysulfate). Oxyethylene alkyl sulfate, aryl sulfonate, etc.), cationic type [alkyl amines (lauryl amine, stearyl trimethyl ammonium chloride, alkyl dimethyl benzyl ammonium chloride, etc.), polyoxyethylene alkyl amines], amphoteric type [carboxylic acid (betaine type ), Sulfate ester salts, etc.]
Of course, it is not limited to these examples.

In addition to these, polyvinyl alcohol (PVA), carboxymethyl cellulose (CMC),
Various auxiliary agents such as gum arabic, polyvinyl acetate, sodium alginate, gelatin and tragacanth gum can be used.

In the present invention, when producing the above-mentioned various preparations, 0.001% to 95% of the compound of the present invention is added.
(% By weight; the same applies hereinafter), preferably 0.01% to 75%
It can be formulated so as to contain in the range of. For example, in the case of powder, DL powder, and fine powder (F),
0.01% to 5%, in the case of granules 0.01% to 10%
%, Wettable powders, emulsions, and liquid preparations can be contained in the range of 1% to 75%.

In the case of granules, for example, the thus-prepared preparation may be sprayed as it is on the soil surface, in the soil or in water in an amount of about 0.3 g to 300 g per 10 ares as an active ingredient amount. In the case of a wettable powder, an emulsion, a sol and the like, they may be diluted with water or a suitable solvent and diluted in the range of about 0.3 to 300 g per 10 ares as an active ingredient amount.

When the compound of the present invention is used as a herbicide, it can be used in combination with a known herbicide, insecticide or plant regulator to expand its applicability, and in some cases, a synergistic effect is expected. You can also do it.

The method of formulating the compound of the present invention represented by the general formula (1) as a herbicide is described in Examples 3 to 6 below.
Explain. However, the present invention is not limited only to these examples, it can be mixed with various other additives in any proportion, and other herbicides and the like can be mixed in any proportion to prepare a formulation. You can also

Compound No. Is shown in Tables 1 to 3 above, and all parts in the examples are parts by weight.

Example 3 (Granule) Compound No. Compound 1 of 3, lauryl sulphate 1 part, calcium lignin sulfonate 1 part, bentonite 30 parts and white clay 67 parts were added with 15 parts of water and kneaded with a kneader, then granulated with a granulator, and then fluidized dryer. And dried to obtain granules containing 1% of active ingredient.

Compound No. 3 instead of compound N
o. Similar granules are obtained using 1, 2, 4 to 77.

Example 4 (Wettable powder) Compound No. 18 parts of compound, 15 parts of white carbon, 3 parts of calcium lignin sulfonate, 3 parts of polyoxyethylene nonyl phenyl ether, 5 parts of diatomaceous earth and 60 parts of clay are uniformly mixed with a pulverizing mixer to obtain 15% of active ingredient. A wettable powder containing is obtained.

Compound No. Instead of Compound No. 18, Compound No. Similar wettable powders are obtained using 1-17 and 19-77.

Example 5 (Emulsion) Compound No. 21 compounds, 20 parts, Solpol 700
20 parts of H (Emulsifier manufactured by Toho Chemical Industry Co., Ltd.) and 60 parts of xylene are mixed to obtain an emulsion containing 20% of the active ingredient.

Compound No. 21 instead of Compound No. 21. Similar emulsions are obtained with 1-20, 22-77.

Example 6 (powder) Compound No. 12 parts of compound 0.5 parts, silicic acid fine powder 0.5 parts, calcium stearate 0.5 parts, clay 50 parts and talc 48.5 parts are uniformly mixed and ground, and a powder containing 0.5% of the active ingredient. To get

Compound No. 12 instead of Compound No. Similar powders are obtained using 1 to 11 and 13 to 77.

Next, Test Examples 1 and 2 are shown to demonstrate the herbicidal effect of the compound of the present invention.

Test Example 1. Herbicidal effect test for paddy field weeds and phytotoxicity test for transplanted paddy rice Paddy soil (planting soil) is filled in a plastic pot with a size of 1 / 5,000 are, and rice paddy, broad-leaved weeds (Azena, Kishigusa, Mizohakobe) and firefly seeds are filled. 30 seeds were seeded at a depth of 1-2 cm.
One day after sowing, the water was flooded to keep the water depth at 2 cm. Three days after sowing, paddy rice at the 2.5 leaf stage was transplanted and grown in a greenhouse. One day after transplanting the paddy rice, the emulsion prepared according to Example 5 was diluted with water to a predetermined amount, and 10 ml was dropped per pot.

This test was carried out in duplicate for each chemical concentration group, and 21 days after the treatment, the herbicidal rate (%) was calculated by the following formula,
The herbicidal effect and phytotoxicity were investigated based on the following evaluation indexes. The results are shown in Tables 4-5.

[0066]

[Equation 1]

[0067]

[0068]

[Table 4]

[0069]

[Table 5]

[0070]

Embedded image Comparative drug A; (Compounds described in JP-A-4-501726)

[0071]

Embedded image Comparative drug B; (Compounds described in JP-A-4-501726)

[0072]

Embedded image Comparative drug C; (Compounds described in US Pat. No. 5,092,919)

[0073]

Embedded image Comparative drug D; (Compounds described in US Pat. No. 5,110,979)

Test Example 2 Herbicidal effect on upland weeds and phytotoxicity test on crops 1) Herbicidal effect test on upland weeds Field soil (alluvial loam soil) was packed in a biscuit pot with a size of 1/5000 are, and a soil of 1 cm in surface layer. And 50 seeds of various kinds of weed seeds such as crabgrass, locust, white foxtail, white squirrel, white squirrel, and sardine were uniformly mixed, and the surface layer was lightly pressed. Two days after sowing, the emulsion prepared according to Example 5 was diluted with water, and 100 liters per 10 ares (corresponding to 100 g per 10 ares in terms of application amount of active ingredient) was sprayed onto the soil surface.

This test is carried out in a double system for each chemical concentration group,
30 days after the chemical treatment, the herbicidal effect was investigated based on the same evaluation index as in Test Example 1.

2) Chemical damage test for crops Field soil (alluvial loam soil) was packed in a biscuit pot with a size of 1 / 10,000 are and seeds of each crop (5 soybeans,
5 corns, 10 beets, 10 rapeseed and 10 wheats) were sown in separate pots, and the surface layer was lightly pressed. One day after sowing, the emulsion prepared according to Example 5 was diluted with water, and 100 liters per 10 ares (corresponding to 100 g per 10 ares in active ingredient amount) was sprayed onto the soil surface.

This test is carried out in a double system for each chemical concentration group,
30 days after the chemical treatment, the degree of phytotoxicity to each crop was investigated based on the same evaluation index as in Test Example 1. The results are shown in Tables 6-7.

[0078]

[Table 6]

[0079]

[Table 7]

[0080]

INDUSTRIAL APPLICABILITY The compound of the present invention has an excellent herbicidal effect as compared with known similar compounds, and exhibits excellent selectivity between crops and weeds. That is, in flooding treatment of paddy fields, various weeds that are problematic, for example, grass weeds such as Taenia japonicus, azena, yellow grass, broad-leaved weeds such as Mizochabe,
It can act on a wide variety of cyperaceous weeds, such as Pleurotus cornucopiae, firefly, pine nuts, and cyperus edulis, eels, urchins, etc., to be almost completely weeded, and it is not harmful to paddy rice.

The compounds of the present invention are also problematic in foliage treatment and soil treatment of upland fields, such as buckwheat vine, Aedes persicae,
Broad-leaved weeds such as starfish, chickweed, white lobster, blue-spotted gall, tuna, velvetleaf, and morning glory, Tainubie, Inobie, Enokurogusa, Mejisiba, Scutellaria barbata,
It can act on a wide range of grass weeds such as oats and cyperaceae weeds such as pearl nuts, and can almost completely weed it, and it is also harmful to major crops such as corn, wheat, rice, soybean, rape and beet. Do not give.

In addition, there is little human toxicity and fish toxicity. Therefore, it can be used safely.

─────────────────────────────────────────────────── ─── Continuation of the front page (51) Int.Cl. ⁶ Identification code Internal reference number FI technical display location A01N 37/34 110 37/40 41/10 A 47/30 F C07C 69/92 205/45 233 / 32 235/82 251/48 255/37 255/54 275/36 317/24 323/22 (72) Inventor Umeda Ten Kanagawa Prefecture Sagamihara City Sagamidai housing complex No. 2-306 (72) Inventor Hirokazu Yoshizawa Kanagawa Prefecture 1 Clover Heights 303, 72, Toda, Atsugi-shi 303 (72) Inventor Takashi Takeuchi 2385, Toda, Atsugi, Kanagawa Prefecture

Claims (2)

[Claims] 1. A general formula:[Wherein, R¹ Represents a hydrogen atom or a lower alkyl group,
X is a lower alkyl group, a lower alkenyl group, a lower alkoxy group
Si group, lower alkynyloxy group, halogen atom, nitro
Group, trifluoromethyl group, -COR²Group (however, group
Medium, R²Is a lower alkyl group, a lower alkoxy group or a low
Represents a primary alkylamino group. ), -NHCOR³Group
But, Motochu, R³Is a lower alkyl group or lower alkyl
Represents an amino group. ), -S (O)_mR^FourGroup (however, group
Medium, R^FourRepresents a lower alkyl group, m represents 0 or 2.
You. ), -C (CH₃) = NOR^FiveGroup (however, in the group, R
^FiveRepresents a lower alkyl group. ) Or-(CH₂)_yCN
Represents a group (wherein y represents 0 or 1),
n represents 0, 1 or 2. ] Cyclohexa
Ndione derivative. 2. A general formula:[Wherein, R¹ Represents a hydrogen atom or a lower alkyl group,
X is a lower alkyl group, a lower alkenyl group, a lower alkoxy group
Si group, lower alkynyloxy group, halogen atom, nitro
Group, trifluoromethyl group, -COR²Group (however, group
Medium, R²Is a lower alkyl group, a lower alkoxy group or a low
Represents a primary alkylamino group. ), -NHCOR³Group
But, Motochu, R³Is a lower alkyl group or lower alkyl
Represents an amino group. ), -S (O)_mR^FourGroup (however, group
Medium, R^FourRepresents a lower alkyl group, m represents 0 or 2.
You. ), -C (CH₃) = NOR^FiveGroup (however, in the group, R
^FiveRepresents a lower alkyl group. ) Or-(CH₂)_yCN
Represents a group (wherein y represents 0 or 1),
n represents 0, 1 or 2. ] Cyclohexa
Characterized in that it contains a dianion derivative as an active ingredient.
Herbicide to do.