JPH064575B2 - N- (3-chloro-4-isopropylphenyl) cyclopropanecarboxylic acid amide derivative and selective herbicide - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION [Industrial Field of Application] The present invention is directed to containing N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivatives and these compounds as active ingredients. The present invention relates to a characteristic selective herbicide, particularly to a selective herbicide that effectively and selectively controls harmful weeds by foliar application in the cultivation of wheat, which is an important crop of the Gramineae in the agricultural industry.

[Conventional technology]

The most widely used herbicides for wheat are 2,4-dichlorophenoxyacetic acid (2.4-D), 2
-Methyl-chlorophenoxyacetic acid (MCPA), 4- (2-
Methyl-4-chlorophenoxy) butyric acid (MCPB), 4-
Phenoxy-type herbicides such as (2,4-dichlorophenoxy) butyric acid (2,4-DB) can be mentioned, but these herbicides are foliar treatment agents effective only for controlling broadleaf weeds, and also have a phytotoxic effect on wheat. Therefore, its use is limited to the stage where the crop has grown to some extent.

Moreover, 3- (3,4-dichlorophenyl) -1-methoxy-1-methylurea [linuron], 3-
(3-chloro-4-methoxyphenyl) -1,1-dimethylurea [metoxuron], 3- (3-
Chloro-4-methylphenyl) -1,1-dimethylurea [chlortoluron], 3- (4-isopropylphenyl-1,1-dimethylurea [isoproturon]], 3- (2-benzothiazolyl) ) -1,3-Dimethylurea [metabenzthiazulone (met
Urea herbicides such as habenzthiazuron) are also very important in wheat cultivation, but most of them are used as pre-emergence soil treatment agents because they cause phytotoxicity to crops. Even when it is used as a foliar treatment agent, its selectivity greatly differs depending on the variety and cultivation conditions, and the herbicidal spectral does not reach all problem weeds, and is used as a mixture. Is normal.

In addition, 2- (2-chloro-4-ethylamino-s-triazin-6-ylamino) -2-methylpropionitrile [cyanazine], 3,4-dimethyl-
2,6-Dinitro-N-1-ethylpropylaniline [pendimethalin], α, α, α-trifluoro-2,6-dinitro-N-2-chloroethyl-
N-propyl-p-toluidine [flucloralin (fluc
hloralin)], 2,4-dichlorophenyl-3-methoxycarbonyl-4-nitrophenyl ether [bifenox] and other herbicides are used for wheat cultivation, and used alone against many problem weeds. The effect is insufficient. Further, 4-chloro-2-butynyl-N- (3-chlorophenyl) -carbamate [barban] as a dedicated agent for highly damaging weeds-wild oats,
N-benzoyl-N- (3,4-dichlorophenyl) -2
-Aminopropionic acid ethyl ester [benzoylpropethyl], 1,2-dimethyl-
3,5-diphenyl-1H-pyrazolium methylsulfate [difenzoquat], and (±) -2- [4- (2,4-dichlorophenoxy) phenoxy] propionic acid methyl ester [diclofofol] However, its practical effect is still insufficient.

Herbicides for wheat other than the compounds listed above are 3
-Isopropyl-1H-2,1,3-benzothiadiazine-
(4) -3H-on-2,2-dioxide [Bentazone (bent
azone)], or 2-chloro-N- (4-methoxy-6-methyl-), which has recently attracted attention as a highly active compound.
1,3,5-Triazin-2-ylaminocarbonyl) benzenesulfonamide [chloro-sulfu
ron)] and the like. The former is for foliar application,
Although it is a compound showing extremely excellent safety against wheat, its target weeds are broadleaf weeds, and only some broadleaf weeds. In addition, the latter is a drug with excellent soil treatment effect at extremely low dosage, exceptional residual effect, and extremely high safety against wheat. There is a danger of serious chemical damage and its use is extremely limited. At present, not only excellent performance, but also human safety and environmental safety are strongly required as essential conditions that pesticides must have.

On the other hand, many studies on N-phenylcarboxylic acid amide derivatives have been conducted for a long time, and various excellent herbicides have been known and used. These are CW. Hoffman et al., The Journal of the Agricultural and Food Chemistry (CWHoff
man, et al., J. Agric. Food. Chem.) , 8 , 298 (1960) [N-
(3,4-dichlorophenyl) propionamide; stam; propanil], British Patent No. 869169 [Carcil; Solan], West German Patent No. 1166547 [potarum; monalid], US Patent 3816092, British Patent No. 885043 [ DCM
A; dicryl], U.S. Pat. No. 3,277,107 [clover; cypromide], U.S. Pat. No. 4,166,735, and U.S. Pat. No. 3,277,171, etc., but most of them are extremely effective in killing weeds in foliar treatment. In addition, it shows high selectivity for some important crops and is an excellent herbicide. Further, these compounds can be expected to have characteristics such as relatively rapid decomposition, and it is expected to some extent that the effects on the crops planted after harvest as well as the effects of compound residues in the environment are small. However, many of these prior arts have no disclosure regarding wheat selectivity, or if there is a description, the selectivity is insufficient or the effect is insufficient. In fact, these herbicides described in the prior art are difficult to actually use in wheat cultivation.

Also, Japanese Patent Publication No. 41-14240 and West German Patent 22
49547 and the like disclose N-phenylcarboxylic acid amide derivatives relating to wheat selectivity, but they cannot be said to be sufficient in terms of efficacy and phytotoxicity to crops. Alternatively, JP-A-59-193806 and JP-A-60-23357 also disclose N- (4-isopropylphenyl) -carboxylic acid amide derivatives, but their major drawbacks are Is unstable and does not show herbicidal activity against some important weeds, especially the genus Astragalus, Plutella xylostella, Scutellaria baicalensis, and Commelina communis.

Therefore, important crops of Gramineae-in particular, the development of agents having an intrinsic selectivity for crops in the cultivation of wheat, the development of agents that are less affected by physical factors such as soil conditions, that is, foliar treatment agents, and lower There is a strong demand for the development of a drug that exhibits a wide range of herbicidal spectra from grass weeds to broad-leaved weeds, as well as a drug that is effective at a high dose and that decomposes rapidly and does not adversely affect the environment such as compound contamination. Has become.

[Problems to be Solved by the Invention]

The present invention, in the cultivation of wheat, which is an important crop of the family Gramineae, is a herbicide that is not affected by physical factors such as soil conditions or changes in phytotoxicity, and in particular has a selectivity for wheat in foliar treatment. An object of the present invention is to provide a herbicide, that is, a foliar treatment type highly selective herbicide which is effective at a lower dose and is simple and reliable in the cultivation of important crops of grass, particularly wheat.

[Means and Actions for Solving the Problems]

The present inventors have studied a number of compounds for the purpose of developing highly selective herbicides for cultivating important crops of grass, especially wheat, and as a result, N- (3-chloro-4-isopropylphenyl)- Cyclopropanecarboxylic acid amide derivative, when subjected to foliage treatment using this, does not cause any phytotoxicity at all even with extremely high concentration spraying on important crops of grass, especially wheat, while having an extremely broad herbicidal spectrum. The present invention has been completed by finding that it has an excellent selective herbicidal action and has a characteristic to solve the above-mentioned problems.

In general, it is considered that the compounds of the same system and the structurally similar compounds have similar properties, but in reality, their action characteristics cannot be easily analogized, and only the alkyl chain of one substituent is increased. However, the herbicidal activity against weeds and the phytotoxicity against crops vary greatly.

The N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative according to the present invention has the general formula (I). (In the formula, R represents a hydrogen atom or a methyl group) and is a novel compound.

The herbicide containing the N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative according to the present invention as an active ingredient has the action property that when treated with foliage, it causes problems in most fields. harmful weeds, for example wild oats, giant foxtail made, Western foxtail, foxtail, annual bluegrass, barnyardgrass, crabgrass, gramineous little harm weeds and slender amaranth, such as green foxtail, purslane, cocklebur, cleavers, common lambsquarters, chickweed, Ipomoea purpurea, Miminagusa, velvetleaf,
Ebisugusa, Gumbai Nazuna, Hotokenoza, mustard,
It extremely effectively controls weeds such as communis, serrata sorghum, Scutellaria baicalensis, Scutellaria baicalensis, Astragalus vulgaris, Astragalus chinensis, Chamomile, Rhododendron and nettle.
On the other hand, no phytotoxicity to important gramineous crops, especially wheat, was observed.

As described above, the N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative according to the present invention is used in the cultivation of important crops of grass, especially wheat,
It is essentially foliar treatment selective and can be used very safely. At present, various herbicides used in wheat cultivation are soil treatment agents, and the drawbacks of these herbicides, namely, effects due to physical factors such as soil conditions and fluctuations in phytotoxicity, are the herbicides according to the present invention. Nothing is observed in the drug. In addition, there is no problem with the effect on subsequent crops.

The N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative according to the present invention is a novel compound and is produced by the following method.

That is, to 3-chloro-4-isopropylaniline,
By reacting the cyclopropanecarboxylic acid anhydride represented by the general formula (II) or the cyclopropanecarboxylic acid halide represented by the general formula (III), the compound can be easily synthesized according to the following formula.

The reaction is carried out without solvent or in an inert solvent. Examples of the inert solvent include aromatics such as benzene, toluene, xylene, chlorobenzene, and dichlorobenzene,
Acetone, ketones such as methyl ethyl ketone, acetonitrile, nitriles such as propionitrile, ethers such as ethyl ether, tetrahydrofuran, dioxane, aprotic polar solvents such as dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid amide, etc. To be When using an acid halide or acid anhydride, triethylamine, pyridine, dimethylaniline, 1,8-diazapicyclo (5,4,0) may be used as necessary.
An organic base such as -7-undecene or an inorganic base such as potassium carbonate, sodium carbonate, caustic soda, caustic potash, and sodium hydrogen carbonate may be used as the deoxidizing agent.
The reaction temperature is -10 ° C to 150 ° C, preferably 5 ° C to 90 ° C.
C., more preferably 15 to 70.degree. The reaction may be carried out at the reflux temperature of the solvent used. The reaction time varies depending on the reaction temperature or the solvent used, but is 1 second to
10 hours, preferably 1 minute to 5 hours, more preferably 2
It is 0 minutes to 3 hours.

The N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative of the present invention can be applied in any amount depending on the necessity of suppressing the growth of weeds, and it is standard. Is in the range of 0.1 to 10 kg per hectare, preferably 0.2 to 3 kg per hectare.

The herbicide according to the present invention contains the compound represented by the general formula (I) according to the present invention as a main component. The compound represented by the general formula (I) according to the present invention may be used as it is as a raw material for plants to be treated. But,
Generally, to the compound represented by the general formula (I) according to the present invention, a carrier and, if necessary, other auxiliary agents are added and mixed, and usually used formulation forms such as powders, granules, wettable powders,
It is used as a herbicide prepared in emulsions and flowable formulations.

As the carrier, inorganic substances such as clays, talc, bentonite, calcium carbonate, diatomaceous earth, zeolite and silicic acid anhydride; plant organic substances such as wheat flour, soybean flour, starch, crystalline cellulose; petroleum resin, polyvinyl chloride , High molecular compounds such as polyalkylene glycols;
Urea; waxes and the like. Further, liquid carriers such as various oils, organic solvents and water can be used.

As the auxiliary agent, for example, a wetting agent, a dispersant, a fixing agent, a spreading agent and the like can be appropriately used alone or in combination as necessary.

As an auxiliary agent used for the purpose of wetting, dispersing, spreading, stabilizing components, stabilizing physical properties, various surfactants or polymers such as gelatin, albumin, sodium alginate, methyl cellulose, polyvinyl alcohol, xanthan gum, etc. Examples include compounds and other auxiliary agents. Further, in the case of a flowable agent, an industrial bactericidal agent or an antibacterial / antifungal agent is optionally added for antibacterial / antifungal purposes.

As the surfactant, nonionic, anionic, cationic and amphoteric surfactants can be appropriately used. Preferred examples include alkylphenols, higher alcohols, alkylnaphthols, higher fatty acids, fatty acid esters, dialkylphosphate amines, etc., which are polymerized with ethylene oxide, ethylene oxide and propylene oxide, and alkyl sulfate ester salts (sodium lauryl sulfate). Etc.), alkyl sulfonates (sodium 2-ethylhexene sulfonate, etc.), and aryl sulfonates (sodium lignin sulfonate, sodium dodecylbenzene sulfonate, etc.).

The content of the compound represented by the general formula (I) in the herbicide according to the present invention varies depending on the formulation form, but is usually 1 to 20% by weight for powders, 20 to 90% by weight for wettable powders,
Granules are 1 to 30% by weight, emulsions are 1 to 50% by weight, flowable formulations are 10 to 90% by weight, and dry flowable formulations are 20 to 70% by weight. Content of auxiliary agent is 0
The content of the carrier is 100% by weight minus the contents of the active ingredient compound and the auxiliary agent.

The herbicide of the present invention is one or more kinds of other herbicides,
Not only can it be used as a mixture with pesticides such as insecticides and plant growth regulators, soil improvement agents or fertilizing substances, but it is also possible to make a mixed preparation with these, and in some cases a synergistic effect. Can be expected.

〔Example〕

A synthesis example of the N- (3-chloro-4-isopropylphenyl) -cyclopropanecarboxylic acid amide derivative according to the present invention is shown below.

Synthesis Example 1 N- (3-chloro-4-isopropylphenyl) -1-methylcyclopropanecarboxylic acid amide 3-chloro-4-isopropylaniline 1.0 g (5.9 × 1)
0 ^-3 mol) was dissolved in toluene 40 ml, triethylamine 0.7g and 1-methyl-cyclopropanecarboxylic acid chloride 0.8g (6.8 × 10 ^-3 mol) and the mixture was stirred for 1 hour at room temperature. After separating the precipitated crystals, the solution was washed with a saturated aqueous solution of sodium hydrogencarbonate, dried over anhydrous sodium sulfate. The oily substance obtained by concentration with an evaporator was separated and purified by silica gel column chromatography (developing solvent; benzene: ethyl acetate = 40: 1 (v / v)) to give N- (3-chloro-4-isopropylphenyl). ) -1-Methylcyclopropanecarboxylic acid amide 1.4 g was obtained. Yield 94.2% based on 3-chloro-4-isopropylaniline.

Other compounds represented by the general formula (I) according to the present invention were also synthesized according to the above synthesis examples.

Table 1 shows the compounds represented by the general formula (I) according to the present invention and their physical properties. The active ingredient compounds in the following formulation examples and test examples are shown by the compound numbers shown in Table 1.

Next, formulation examples and herbicidal activity test examples of the herbicide according to the present invention are shown.

Formulation example 1 (wettable powder) Compound of the present invention (1): 20 parts by weight, sodium alkylbenzenesulfonate: 2 parts by weight, polyoxyethylene alkylphenyl ether: 2 parts by weight and sikhlite:
76 parts by weight were well pulverized and mixed to obtain a wettable powder.

Formulation Example 2 (wettable powder) Compound of the present invention (1): 30 parts by weight, polyoxyethylene alkylphenyl ether ammonium sulfate salt: 6 parts by weight, sodium naphthalenesulfonate formalin condensate: 2 parts by weight, sodium alkylbenzene sulfonate: 1 By weight, 2 parts by weight of polyvinyl alcohol and 59 parts by weight of diatomaceous earth were thoroughly pulverized and mixed to obtain a wettable powder.

Formulation Example 3 (wettable powder) Compound (2) of the present invention: 50 parts by weight, white carbon: 3
By weight, 4 parts by weight of ammonium polyoxyethylene alkylphenyl ether sulfate, 4 parts by weight of sodium alkylbenzenesulfonate and 41 parts by weight of diatomaceous earth were well pulverized and mixed to obtain a wettable powder.

Formulation Example 4 (wettable powder) Compound of the present invention (2): 50 parts by weight, white carbon: 5
By weight, 4 parts by weight of ammonium polyoxyethylene alkylphenyl ether sulfate, 4 parts by weight of sodium lignin sulfonate, and 34 parts by weight of diatomaceous earth were well pulverized and mixed to obtain a wettable powder.

Formulation Example 5 Inventive compound (1): 80 parts by weight, white carbon: 5
Parts by weight, polyoxyethylene alkylphenyl ether sulfate ammonium salt: 7 parts by weight, sodium naphthalene sulfonate formalin condensate: 2 parts by weight, sodium alkylbenzene sulfonate: 2 parts by weight and diatomaceous earth: 4 parts by weight, and water is thoroughly mixed. I got a Japanese medicine.

Formulation Example 6 (flowable agent) Inventive compound (2): 20 parts by weight, sodium lignin sulfonate: 2 parts by weight, xanthan gum: 0.3 parts by weight and polyoxyethylene alkylaryl ether: 1
To the parts by weight, 76.7 parts by weight of water was added and mixed, and then finely pulverized using a sand grinder to obtain a flowable agent.

Formulation Example 7 (flowable agent) Compound (2) of the present invention: 40 parts by weight, naphthalene sulfone
Sodium acid formalin condensate: 3 parts by weight, lignin
Sodium ruphonate: 2 parts by weight, xanthan gum: 0.
1 part by weight, Dell Top (Takeda Pharmaceutical Industrial sterilization
Agent): 0.1 part by weight and polyoxyethylene alkyl alcohol
Add 22.8 parts by weight of reel ether and 52.8 parts by weight of water.
After mixing, use a sand grinder to finely pulverize the floor
I got a bull pill.

Formulation Example 8 (Dust) Compound of the present invention (1): 3 parts by weight, sodium lignin sulfonate: 3 parts by weight, polyoxyethylene alkylaryl ether: 2 parts by weight and clay: 92 parts by weight are mixed and pulverized to obtain a powdery product. It was

Formulation Example 9 (Dust) The present compound (1): 20 parts by weight, sodium lignin sulfonate: 5 parts by weight, polyoxyethylene alkylaryl ether: 4 parts by weight and clay: 71 parts by weight are mixed and pulverized to obtain a powdery product. It was

Formulation Example 10 (Dry flowable agent) The compound (1) of the present invention: 60 parts by weight, sodium alkylbenzene sulfonate: 5 parts by weight and polypropylene glycol polyethylene glycol ether: 35 parts by weight are mixed, and the mixture is slightly mixed using a Jet-O-mizer. It was pulverized to obtain a dry flowable agent.

Formulation Example 11 (dry flowable agent) The compound (2) of the present invention: 70 parts by weight, sodium alkylbenzene sulfonate: 2 parts by weight, polypropylene glycol polyethylene glycol ether: 18 parts by weight and white carbon: 10 parts by weight are mixed, and Jet- O-
It was finely pulverized using a mizer to obtain a dry flowable agent.

Formulation Example 12 (Granule) Finely pulverized compound (2) of the present invention: 20.5 parts by weight, Gohsenol GL-05S (Nippon Gosei Kagaku Co., Ltd. PVA): 2.0 parts by weight, Sun Extract P-252 (Sanyo Kokusaku) 2.0 parts by weight of lignin sulfonic acid soda manufactured by Pulp Co., Ltd. and 75.5 parts by weight of clay were thoroughly mixed, then an appropriate amount of water was added to wet them, and then extrusion granulation was carried out by an injection molding machine. This is air-dried at 60-90 ℃ and crushed, then 0.3-1mm with a sizing machine.
The granules were sized to obtain granules.

Formulation Example 13 (Granule) Finely ground compound (2) of the present invention: 5 parts by weight, bentonite: 72 parts by weight, talc: 20 parts by weight, calcium dodecylbenzene sulfonate: 2 parts by weight and calcium lignin sulfonate: 1 part by weight After thoroughly mixing the parts, an appropriate amount of water was added to wet them, and the mixture was extruded and granulated by an injection molding machine. This was air-dried at 60 to 90 ° C. and crushed, and then sized to 0.5 to 1.2 mm with a sizing machine to obtain a granule.

Formulation Example 14 (Granule) Finely ground compound (1) of the present invention: 12 parts by weight, bentonite: 60 parts by weight, talc: 25 parts by weight, sodium naphthalene sulfonate formalin condensate: 2 parts by weight and dioctyl sulfosuccinate After thoroughly mixing 1 part by weight, an appropriate amount of water was added to wet the mixture, and then extrusion granulation was performed using an injection molding machine. Air dry this at 60-90 ° C,
After disintegration, the granules were granulated with a granulator to 0.3 to 1 mm.

Formulation Example 15 (Emulsion) 10 parts by weight of the present compound (2), 10 parts by weight of Solpol 800A (trade name of Toho Chemical Co., Ltd .: mixture of nonionic surfactant and anionic surfactant) and benzene :
Emulsion was obtained by mixing and dissolving 80 parts by weight.

Formulation Example 16 (emulsion) Compound (1) of the present invention: 50 parts by weight, Gaffac RS-610 [General Anil & Film (General Anil
ine & Film Corporation) trade name: polyoxyethylene phosphate]: 15 parts by weight and o-xylene: 35 parts by weight were mixed and dissolved to obtain an emulsion.

Formulation Example 17 (emulsion) Inventive compound (1): 25 parts by weight, Plysurf A-21
OG (Daiichi Kogyo Seiyaku Co., Ltd. product name: polyoxyethylene phosphate): 15 parts by weight and o-xylene:
An emulsion was obtained by mixing and dissolving 60 parts by weight.

Test Example 1 1 / 10.000 Earl resin pots are filled with field soil, and test plants are sown one by one and grown in a greenhouse.
When each plant had 2-3 leaves, each compound was made into a solution with acetone containing polyoxyethylene sorbitan monooleate and sorbitan monolaurate, and a predetermined amount was sprayed with a pressurized micro-sprayer. 2K per hectare
1 equivalent amount. The effects on crops and weeds were observed 21 days after the drug was sprayed. The results are shown in Table 2.
The degree of damage to the test plant was expressed as follows, with complete death being 5 and no effect at all.

Table Degree of damage (%) Damage status 5 100 Death (complete control in the case of weeds) 4 80 Injury (80% control) 3 60 Moderate damage (60% control) 2 40 Small damage (40% control) 1 20 Little Small harm (20% control) 0 0 Harmless (complete control) Test Example 2 1 / 1.000 areal resin planters were filled with field soil, and weeded seeds of wild oats, blue-green amberjack, bluegrass, chickweed, white rosa, and wild mustard were planted on the planters. At the same time, seeds of wheat (variety: Norin 61) and barley (variety: Tochigi Sekitori 1) were sown as crops and cultivated in Phytotron (12 to 18 ° C.). When 2 to 3 leaves of wheat were reached, a predetermined amount of the test compound prepared according to Formulation Example 15 was diluted with 500 equivalents of water per hectare,
Treated with a micro-pressure sprayer. 3 weeks after drug treatment,
The effects on weeds and crops were observed and evaluated. Table 3 shows the test results. The degree of damage to the plant to be examined is Test Example 1
Displayed in the same manner as.

Test Example 3 (Upland vegetation period herbicidal test) packed soil in the planter capacity a / 1.000, wheat, wild oats, giant foxtail, Western foxtail, foxtail, annual bluegrass, Thlaspi arvense, cleavers, common lambsquarters, henbit, Miminagusa, Rotala, Lindernia and chickweed Seeds were sown and grown in a greenhouse. When the test plant grew in the 2-3 leaf stage, a predetermined amount of the flowable agent prepared according to Formulation Example 6 was diluted with 10 equivalents of water per are, and sprayed with a fine sprayer. After 30 days from the treatment, the growth conditions of crops and weeds were investigated, and the results shown in Table 4 were obtained.

In this table, the degree of phytotoxicity to crops and the herbicidal effect on weeds were expressed according to the following evaluation criteria by comparing the growth state of the crops or weeds with the dry weight of the untreated plot.

As the control agents, metabenzthiazulone, diclofop-methyl and propanil, commercially available tribunyl wettable powder, wheyone emulsion and stam emulsion were used.

[Effect of the invention] As is clear from the test results, the general formula according to the present invention
Herbicides containing a compound represented by (I), in foliar treatment that is not affected by soil conditions, etc., while showing a significant herbicidal effect even at low doses against all weeds tested, For useful crops of Gramineae, especially wheat, no phytotoxicity was observed even at extremely high doses, showing excellent selectivity, and comparative drugs (metabenzthiazulone,
(Bentazone, propanil, carcil, etc.) or other known compounds.

Claims (2)

[Claims] 1. A general formula (I) (In the formula, R represents a hydrogen atom or a methyl group.) N- (3-chloro-4-isopropylphenyl)
-Cyclopropanecarboxylic acid amide derivatives. 2. The general formula (I) (In the formula, R represents a hydrogen atom or a methyl group.) N- (3-chloro-4-isopropylphenyl)
-A selective herbicide containing a cyclopropanecarboxylic acid amide derivative as an active ingredient.