JPS58113159A - Alkyl-substituted cyclohexenylacetamide derivative, its preparation and herbicide - Google Patents

Abstract

NEW MATERIAL:A compound of formulaI(R is lower alkyl; m is 1, 2; X is lower alkyl, halogen, CF3; n is 0-2). EXAMPLE:N-3,5-Dimethylphenyl-(2-methyl-1-cyclohexenyl)-acetamide. USE:Herbicide: it has a wide herbicidal spectrum against annual as well as perennial weeds in rice plant fields. Especially it develops high herbicidal effect, when used in soil treatment. Sine it causes no injury to major crops such as rice plant, it can be used safely. PREPARATION:The reaction between cyclohexenylacetic acid of formula II or its reactive derivative and a substituted aniline is carried out using a reaction assistant such as thionyl chloride to give the compound of formulaI.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to ruacetamide derivatives, their production methods, and herbicides containing these derivatives as active ingredients.

More specifically, the first aspect of the present invention represents an alkyl group represented by the general formula (1), m represents an integer of 1 to 2, and X represents a lower alkyl group, customarily. represents an alkyl group having 1 to 6 carbon atoms, a halogen atom or a l-lifluoromethyl group, and nld,
The second present invention is directed to an alkyl fi1-substituted cyclohexenyl acetamide conductor represented by the formula (representing an integer from 0 to 2), wherein R , X , m cyclohexenyl acetic acid or its reactive derivative represented by (and n has the same pronunciation as above) and a substituted aniline represented by general formula (III) n are reacted. The gist is a method for producing an alkyl-substituted cyclohexenyl acetamide derivative represented by formula (1).

Furthermore, the third invention relates to a herbicide characterized by containing an alkyl-substituted cyclohexenyl acetamide derivative represented by the general formula (1) as an active ingredient.

The present inventors succeeded in synthesizing a novel compound represented by general formula (I), and this present compound is
Annual weeds in paddy fields such as Cyperus japonica, Cyperus japonica, and Kikashigusa;
It has been found that it exhibits strong herbicidal activity against woodpeckers, black breams, etc. Furthermore, it has been found that the compound of the present invention has a herbicidal effect on upland weeds such as turmeric, lily, and soybean.

Thus, the compounds of the present invention have a broad herbicidal spectrum when used as herbicides. In order to effectively kill these weeds, the compound of the present invention is preferably applied to the soil or foliage in areas where useful crops are cultivated.
The compound of the present invention exhibits a weed-harvesting effect, particularly in soil treatment.

Moreover, the compounds of the present invention have excellent properties that do not cause phytotoxicity to major crops such as paddy rice, and can be used safely. Therefore, the compound of the present invention can be effectively used as a wood herbicide, and
It can be widely used as a herbicide in areas where various grains and vegetables are cultivated, as well as in orchards, lawns, reed fields, tea gardens, mulberry gardens, rubber gardens, etc.

Known compounds similar to the compound of the present invention are listed in "Journal of Chemical Society" p. 1080 (
1915) and [Journal of the American Kebakal Society, Volume 71, Page 3216 (
1949) describes 1-cyclohexenyl acetanilide and 1-cyclohexenyl acetanilide. Also,
"Chemical Abstracts" Volume 65 +0504 d
describes 4-methyl-3-cyclohexenyl acetanilide and 2-methyl-3-cyclohexenyl acetanilide. In particular, the latter two compounds differ from the compounds of the present invention in the position of the double bond in the cyclohexenyl ring.

However, there is no description of the herbicidal activity of these known compounds. Furthermore, as is clear from the test examples described later, these known compounds exhibit almost no herbicidal activity.

The compound of the present invention has a chemical structure similar to that of the compound described in the above literature, but is a new compound that has not been described in the literature. The compounds of the present invention are significantly superior to similar known compounds in that they have excellent herbicidal effects and have no phytotoxic effects on useful crops such as paddy rice. The present invention was completed based on such new findings.

The method for producing the compound of the present invention, that is, the second method of the present invention, is carried out as follows. First, substituted anilines of the general formula (m) are treated with a suitable organic solvent, such as benzene,
Dissolve it in toluene, xylene, chlorobenzene, dioxane, tetrahydrofuran, methylene chloride, acetone, chloroform, methyl alcohol, etc., and add an equivalent or slightly excess amount of 1-cyclohexenyl acetic acid or its reactive derivative to it. -Or dissolve it in an organic solvent such as benzene and add it. Then, the reaction is carried out at room temperature or with heating or cooling as necessary. In addition, reactive derivatives of 1-cyclohexenyl acetic acid include acid anhydrides, acid chlorides, acid bromides, carboxylic acid esters, etc.
- Can be easily obtained from cyclohexenyl acetic acid by applying known methods.

When reacting substituted anilines with 1-cyclohexenyl acetic acid or its reactive derivatives, suitable reaction aids such as thionyl chloride, phosphorus trichloride,
Phosphorus pentachloride, phosphorus oxychloride, synchhexylcarposiimide, triethylamine, pyridine,
N-methylmorpholine, quinoline, N,N-dimethylaniline, N,N-Gichia, sodium hydroxide, water (potassium oxide, sodium methylate) can be used. The reaction aid is preferably selected and used depending on the type of 1-cyclohexenyl acetic acid and its reactive derivative.

After the completion of the reaction, the reaction product of the reaction aid is removed by filtration or washing with water, and the organic solvent used is distilled off to obtain the nocyclohexenyl acetamide derivative of the general formula (I), which is the compound of the present invention. It can be obtained with good purity and high yield. This compound can be further purified by recrystallization from acetone, methyl alcohol, ethyl alcohol, benzene, toluene, chloroform, etc.

Specific examples of the compound of general formula (1>) according to the present invention are as follows.
Examples are shown in the table. However, the compounds of the present invention are not limited to these examples, and it goes without saying that many other compounds included in general formula (I) can also be used effectively in the same way as the specific example compounds.

In addition, the compound number is also referred to in the following examples and formulation examples.

Incidentally, among the cyclohexenyl acetic acids represented by the general formula (II) used in the method of the present invention, the method for producing 1-cyclohexenyl acetic acid e is described in [Organic Reaction] Volume 1, page 17. There is.

In addition, the method for producing 2-methyl-1-cyclohexenyl acetic acid is described in "Chemical Abstracts", Vol. 25, 2gO (Journal of Chemical Society (1930)).
22+7 pages), and 4-methyl-1-
The method for producing cyclohexenyl acetic acid is described in the above-mentioned document, as well as in [Chemical Abstracts] Vol. 19, 3.
25 is also mentioned. "4ta,5-methyl-1
-The method for producing cyclohexenyl acetic acid is described in [Chemical Abstracts] Volume 38, 36243 (comp, ren
a, page 2148881) and volume 42, 1900
a (Bull, Soc, Chin, Fr-a
nce, (1947), p. 459. In addition, the manufacturing method of 2,6-dimethyl-1-cyclohexenyl acetic acid is described in "Chemical Abstracts" 858.
63 u [J, Org, Chern, Vol. 32, p. 575 (1967) IK.

In the present invention, the above compounds were produced by the methods described in these documents. 1, the other compounds are new substances,
It can be produced by the method shown in the following reaction formula.

11m Note that preparation examples between the starting compounds are illustrated in Reference Examples below.

When the compound of the present invention of the general formula (1) is actually used as a herbicide, the compound of the present invention may be sprayed in the form of one part onto the soil of the crop cultivation area or on the foliage, etc. ,
In order to fully exhibit the herbicidal action of the compound of the present invention, the compound of the present invention is mixed with a suitable phase and auxiliary agents such as surfactants, binders, stabilizers, etc.
It is preferably used in the form of a formulation such as an emulsion, an aqueous solution, an oil suspension, a powder, a granule, a fine granule, or a coarse powder.

In the above, the carrier may be either solid or liquid, as long as it is commonly used for agricultural and horticultural chemicals, and is not limited to a specific carrier. For example, solid carriers include mineral powders (kaolin, bentonite, clay, montmorillonite, talc, diatomaceous earth, mica,
vermiculite, gypsum, calcium carbonate, apatite white carbon, slaked lime, silica sand, ammonium sulfate, urea, etc.),
Vegetable powders (soybean flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resin,
polyvinyl chloride, ketone resin, dammar gum, etc.),
Examples include alumina, silicates, sugar polymers, highly dispersed silicic acid, and waxes.

Liquid carriers include water, alcohols (methyl alcohol, ethyl alcohol, n-propyl alcohol, 1ao-7' lobil alcohol, butanol, ethyl alcohol, benzyl, alcohol, etc.), aromatic hydrocarbons (toluene, benzene, xylene, ethylbenzene, chlorobenzene, methylnaphthalene, etc.), halodanated hydrocarbons (chloroform, carbon tetrachloride, dichloromethane, chloroethylene, monochlorobenzene, trichlorofluoromethane, dichlorosofluoromethanate)
, 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 acedate, amyl acetate, etc.) , acid amides (dimethylformamide, dimethylacetamide, etc.), nitriles (acetonitrile, propionitrile, acrylonitrile, etc.)
, sulfoxides (dimethylformhokind, etc.), alcohol ethers (ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, etc.),
Aliphatic or alicyclic hydrocarbons M Cn-hexane, cyclohexane, industrial gasoline (petroleum ether, solvent naphtha, etc.), petroleum fractions (paraffins, kerosene, light oil, etc.) can be mentioned.

1. During IJ, surfactants (or emulsifiers) are used for purposes such as emulsification, dispersion, solubilization, wetting, foaming, lubrication, and spreading. Such surfactants include nonionic types (polyoxyethylene alkyl ethers, polyoxyethylene alkyl esters, polyoxyethylene sorbitan alkyl esters, sorbitan alkyl esters, etc.) and anionic types (alkylbenzene sulfonates, alkyl sulfosuccinates, alkyl sulfate, ?lioxychetylene alkyl sulfate, aryl sulfonate),
Cationic type [alkylamines (laurylamine, stearyltrimethylammonium chloride, alkyldimethylbenzylammonium chloride, etc.) polyoxyethylene alkylamines], amphoteric type [carboxylic acid (
betaine type), sulfate ester salts], etc.
Of course, the invention is not limited to these examples.

In addition to these, polyvinyl alcohol carboxymethyl cellulose, gum arabic, etc. Various adjuvants such as ribinyl acetate, gelatin, casein, sodium alginate, arabic gum, gum tragacanth, etc. can be used.

However, the compound of the present invention is intended to improve herbicidal efficacy9, and can be used in combination with other herbicides in order to expect a synergistic herbicidal effect. Examples of this include, for example, phenoxy-based removal agents (2,4-dichlorophenoxyacetic acid, 2-methyl-4-chlorophenoxyacetic acid,
2-methyl-4-chlorophenoxybutyric acid and its esters, thioesters, salts), diphenyl fk herbicides (2,4-dichlorophenyl-4'
-nitrophenyl ether, 2,4.6-dolichlorophenyl-4'-nitrophenyl ether, 2-chloro-4-trifluoromethyl-3'-ethoxy-4'-
Nitrophenyl ether, 2,4-dichlorophenyl-4'-nitro-3'-methoxyphenyl ether,
2.4-dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether, etc.), triazine herbicides (2-dichlorophenyl-3'-methoxycarbonyl-4'-nitrophenyl ether, etc.)

Rho 4.6-pisenalamino1. 3. 5-) riazine, 2-chloro-4-ethylamino-6-isozolobylamino-1,3.5-) riazine, 2-methylthio-4,6-bisethylamino-1°3.5-triazine, 2-methylthio-4,6-pisisopropylamino-1,3,5-triazine, etc.), draft herbicides (3-(3,4-dichlorophenyl)-1,1-dimethylurea, 3-(3, 4-dichlorophenyl)-1-methoxy-1-methylurea, 1-(2,2-dimethylbenzyl)-3-p-tolylurea), carbamate herbicides (isopropyl-N-(3-chlorophenyl)carbamate, methyl- N-(3,4-diclophenyl)-carbamate), thiol carbamate herbicides (S-(4-chlorobenzyl)N, N-noethylthiolcar/(l-t, S-ethyl-N, N- hexamethylenethiol carbamate), acid anilide herbicides (3,4-dichloropro-1?onanilide, N
-methoxymethyl-2,6-danityl-α-chloroacetanilide, 2-chloro-2', 6'-diethyl-N-butoxymethyl)-acetanilide, 2-chloro-2', 6'-soethyl-N-( n-propoxyethyl)-acetanilide, N-chloroacetyl-N-(2,6-dinitylphenyl)-glycine ethyl ester, etc.), uracil herbicides (5-bromo-3
~Secondary-butyl-6-methyluracil, 3-
Cyclohexyl-5,6 = trimetherene uranyl)
, pyridinium chlorine herbicides (1,1'-dimethyl-4,4'-bispyridinium chloride, etc.), phosphorus herbicides (N,N-bis(phosphonomethyl)-glycine, thioate, 5-(2-methyl- 1-piperidylcarbonylmethyl)-0,0-di-n-propyldithiophosphate, 5-(2-methyl-1-piperidylcarbonylmethyl)0.0-diphenyldithiophosphate, etc.), toluidine herbicides (α, α , α-trifluoro2,6-sinitro-N, N-dipropyl-
1)-toluidine, etc.), others (5-tert-dityl-3-(2,4-dichloro-5-isopropoxyphenyl)-1,3,4-oxadiazolin-2-one,
3-isopropyl-IH-2,I, 3-benzothiacyanone-+41-3 H-one-2,2-dioxide,
α-(β-naphthoxy)-propionanilide,
Examples include, but are not limited to, 4-('2,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate).

1. The compound of the present invention can be used in combination with insecticides, nematicides, fungicides, water-applied insecticides and fungicides, soil-applied fungicides and insecticides, plant growth regulators, fertilizers, etc., as necessary. .

The application amount of the compound of the present invention of general formula (1) varies depending on the type of specific compound to be used, the type of weeds to be weeded, etc., but is generally 0.02kli per H + O area.
It is preferably in the range of 1 to 2 kg.

Next, an example of the preparation of the starting compound (Irl) used in the method of the present invention will be explained in detail with reference to Reference Examples, and an example of the preparation of the compound of the present invention (Il) will be explained in detail with reference to Example 1.

Reference fl11 fil 3. Synthesis of 5-dimethyl-1-hydroxycyclohexyl acetic acid ethyl ester In a 500 m capacity reaction flask equipped with a stirrer, a thermometer, a reflux condenser with a calcium chloride tube, and a dropping funnel, was added zinc flakes + 3i (o, Add 2 moles). Separately, bromoacetic acid ethyl ester 33.4v (0.2 mol L)
3,5-dimethylcyclohegisanone 25.3v (0.2
mol), 70 me of toluene, and 70 me of benzene, put it into a dropping funnel, and put 30 d of it into a reaction flask.
Add iodine O and IP. When heated while stirring, a violent reaction occurs and reflux begins. Dripping is started from the dropping funnel, and the reaction is carried out while adjusting the dropping rate to maintain a reflux state. 2 hours after completion of dripping 85~qo
When the reaction is carried out under OC, zinc disappears and the completion of the reaction is confirmed. The reaction solution was cooled to room temperature, 105 d of a 10% aqueous sulfuric acid solution was added thereto, stirred, and then transferred to a 500 ml separatory funnel and allowed to stand to separate into two layers.

The aqueous solution in the lower layer was removed, washed twice with 50 m of water at 100 mA', added with 5 v of sodium sulfate, shaken thoroughly, dehydrated and filtered. Benzene and toluene in the P solution were distilled off under reduced pressure,
Then, when vacuum distillation is performed, the boiling point is 84-86°C/2
3,5-dimethyl-1-hydroxychlorohexyl acetic acid ethyl ester represented by the following formula at mmHg is obtained as a colorless transparent liquid. Collection! i'30.7 r, yield 71.6 element cumulative analysis value (as C12I■2□03) actual measurement value C67,
23%, H10, 32%, 022.45 % Calculated value C67, 25%, H10, 35%, 022.40
Synthesis of 213,5-dimethyl-1-cyclohequinanyl acetic acid ethyl ester In a 500 d reaction flask equipped with a stirrer, a thermometer, and a reflux condenser with a calcium chloride tube, 2 g of dehydrated benzene and 5 d of dehydrated benzene were added. 80? (0.56 mol) of phosphorus oxide and the previously synthesized ethyl 3,5-dimethyl-1-hydroxycyclohexyl acetate 30 F (0.14 mol) were heated under reflux for 3 hours while stirring vigorously. The reaction solution was cooled to room temperature, and the benzene layer was collected by the decanting method, washed with water, dried with sodium sulfate, and filtered.The benzene in the P solution was distilled off under reduced pressure, and the remaining liquid was distilled using vacuum distillation. 3,5-dimethyl-1-cyclohequinanyl acetic acid ethyl ester represented by the following formula is obtained as a colorless transparent liquid with a boiling point of 53-55°C/O-5mmHg. Yield I21.7?
, collected vehicle 7g, 97% cumulative analysis value (C22H2o02
)Actual measurement value C73,46chi, H10,25%,
016.2'? Calculated value C73, 43, H10
, 27, and 016.30 The double bond is located within the ring, as determined by nuclear magnetic resonance measurements, where 2H of the acetate group is 2.1
This is proven by the observation of 30 ppm K.

+313.Synthesis of 5-dimethyl-1-cyclohexenyl acetic acid 500d equipped with stirrer, thermometer and reflux condenser 8
Ethyl alcohol 100-1 in the fii reaction flask
Water 200rnt, potassium hydroxide 72 (0.13 mol)
and 3,5-dimethyl-1-cyclohexenyl acetic acid ethyl ester 205' (0.10 mol), and
The mixture was heated under reflux for 2 hours from the time of birth. Next, vacuum distillation was performed to concentrate the content to 100 d, and then the solution was cooled to room temperature. Pour this into a separating funnel and add 50σ of ether.
f was added and shaken well to separate the liquids. Take the aqueous solution layer and
Neutralize with 0% sulfuric acid aqueous solution to make P)I2 acidic again, and add 70% methylene chloride to this. Add d and extract. Extract two more times using methylene chloride '70d for a total of three extractions.

Add Glauber's Salt 52 to the methylene chloride layer and shake well! )→1
After dehydration and drying, it was filtered. When methylene chloride in the r liquid is distilled off and the mixture is left in a cool place, 3,5-dimethyl-I-cyclohexenyl acetic acid represented by the following formula is obtained as white crystals. Melting point 44-466Co yield-i
, 16-7f In the same manner as in the above reference example, various other cyclohexenyl acetic acids of the general formula (m) were produced and used for the production of cyclohexenyl acetamide derivatives of the general formula (1).

Example 1 2-Methyl-1-cyclohexenyl acetic acid 7.7r (50
Thionyl chloride 18F (152 mmol) was added to the mixture and heated under reflux for 2 hours. Excess thionyl chloride was distilled off under reduced pressure to obtain 2-methyl-1-cyclohexenyl acetic acid chloride 8.69 (yield 100%) as a yellow oil. Next, a solution of 0.6 oy (3.48 mmol) of this 2-methyl-1-cyclohexenyl acetic acid chloride in benzene t.

-, 3,5-dimethylaniline 0.44 F (3,
63 mmol) and triethylamine 0.372 (3
・63 mmol) was added dropwise to 20 d of a benzene solution containing 63 mmol) at room temperature. After the addition, the mixture was heated under reflux for 2 hours. After the reaction solution was cooled to room temperature, a 3-cycle acid aqueous solution IOme was added and stirred, and then transferred to a separating funnel to separate and remove the hydrochloric acid aqueous layer. Next, after washing twice with water in the order of 20 to 110 and separating the layers to remove the aqueous layer, 5 f of Glauber's salt was added to the organic layer, shaken well, and left to dry. , and filtered. When the p-liquid benzene was distilled under reduced pressure, white crystals were obtained. This white crystal is re-crystallized from benzene, and the title N-3,
5-dimethylphenyl-(2-methyl-1-cyclohexenyl)-acetamide o,b2y (yield 70%) was obtained. The melting point and elemental analysis results of this compound are shown below.

Melting point 118-120°C Elemental analysis value (C17H23NO) Actual value C7' 7.35 壬, T (9,02 easy, N 5
．． Section 41.

06.20 coefficient calculation value C79,33%, H9,01%, N5.
Article 44.

06.22 Next, examples of the formulation of the herbicide of the present invention will be shown, but the proportions of active ingredients, carriers, and adjuvants as well as their types are not limited to the following examples.

In addition, all parts in the formulation examples indicate -1 part by weight.

Formulation example 1. A water use agent is obtained by thoroughly crushing and mixing 30 parts of water use agent compound point 1, 2 parts of lignosulfonic acid calcium salt, 3 parts of dodecylbenzenesulfonic acid sodium salt, and 65 parts of diatomaceous earth.

Formulation Example 20 505 parts of granule compound, 2 parts of white carbon, 5 parts of calcium lignin sulfonate salt and 88 parts of clay were thoroughly ground and mixed, water was added and kneaded well, followed by granulation and drying. Obtain granules.

Formulation example 3: 60 parts of granular clay, 35 parts of bentonite, and 5 parts of lignin sulfonic acid calcium salt are ground and mixed, water is added, mixed, granulated, and dried to form granules containing no active ingredients. to make. Granules are obtained by impregnating 95 parts of the granules with 5 parts of the compound AIO.

Formulation example 40 granules Bentonite 96 sieved to 300-850 microns
1 part is impregnated with 4 parts of Compound Point 14 to obtain granules.

Formulation example 5. 3 parts of the powder compound 20, 36 parts of clay, 60 parts of Merck and 1 part of isopropyl phosphate are added and mixed by pulverization in an atomizer at a rotation speed of 12,000 rpm to obtain a powder.

Formulation example 6. 30 parts of emulsion compound M25, 60 parts of xylene and 10 parts of Tsurpol 5M100 (trade name of a surfactant manufactured by Toho Chemical Industry Co., Ltd. containing a mixture of a nonionic surfactant and an anionic surfactant) Mix well and dissolve to obtain an emulsion.

Next, the herbicidal effects of the compounds of the present invention will be shown in Examples.

Example 2 Submergence soil destruction treatment weed killing test 1 / Paddy soil was filled in a porcelain pot of 15,500 are, and the seeds of wild grass, firefly, Japanese cypress, Japanese cypress, and cypress were evenly sown on the surface layer, and the seeds of Japanese cypress were evenly sown in the soil. After transplanting the tubers and submerging them in water to a depth of 2G, two paddy rice seedlings at the two-leaf stage (variety Nihonbare) were transplanted. When weeds germinated, a predetermined amount of a diluted solution of a hydrating powder obtained according to Formulation Example 1 was uniformly dropped onto the water surface for treatment. Thereafter, the pots were kept in a greenhouse and watered from time to time. 20 days after steam treatment,
The herbicidal effect and the degree of chemical damage to paddy rice were investigated using the following criteria.

This test was conducted using a 1-drug M'3-pot system, and the average value was determined. The results are shown in Table 2.

Weeding effect 5: Weed killing rate 95 or more - complete death 4: Weed killing rate 80 or more - less than 95 3: Weed killing rate 50% or more - less than 80% 2: Weed killing rate 30% or more - less than 50 1: Weed killing rate 10 % or more to less than 30% 0: Herbicidal rate less than 10% Chemical damage level m: Harmless, ±: Slight harm Comparative drugs A and B had the following chemical structures, and were formulated and tested in the same manner as the uninvented compound. .

Comparative drug A (Journal of Chemical Research)
o page 2 and Journal of American Chemical
Compound described in Society Vol. 71, page 3216) Comparative drug B (same as above) Example 3 Seed germination inhibition test 10 kg of test compound was accurately weighed, and 0.3 ml of acetone was added. Add and dissolve the emulsifier (equal mixture of Tsurupol 355H (trade name, manufactured by Toho Chemical Co., Ltd.) and Nucor (trade name, manufactured by Nippon Nyukazai Co., Ltd.)) O-
Add 3 ml and emulsify by adding 9.4 ml of distilled water.
This was used as a test liquid.

P paper (A2) 2 in a glass petri dish with a diameter of 5.5 (, rn)
After laying a sheet and injecting 4 of the above chemicals, crush 10 radish seeds (variety: Tokinashi) and put them in a 288C humidifier.7
Germination was carried out under dark conditions for 1 day. The germination inhibition rate was expressed as a ratio of 100 for the plot without chemical addition.

As shown in Table 3, the results showed that the compound of the present invention had a higher ability to inhibit seed germination than the comparative compound.

Table 3 Procedural Amendment (Voluntary) September 20, 1980 Commissioner of the Japan Patent Office 1 Indication of the case Patent Application No. 209988 of 1982 2 Name of the invention Alkyl-substituted cyclohexenyl acetamide derivatives, their manufacturing process and herbicides 3. Relationship with the case of the person making the amendment Special tt'l Applicant address: 4-2, Nihonbashimotoki-cho, Chuo-ku, Tokyo Name: Hokuko Chemical Industry Co., Ltd. 4. Agent: 5. Details of the invention in the specification to be amended. Explanation column 6, Contents of amendment (1) Next to page 16 of the specification (at the end of Table 1), there is a table attached as Table 1 (continued) (compound numbers 34 to 41).
).

(2) In the reaction formula on page 18, line 4, r(1:)J is corrected to r(1:1)J.

(3) Insert "," after "apatite" on page 19, line 11 of the same.

+41 Same, page 20, line 1, 1 benzyl, alco.”
is corrected to "benzylalco".

15) Delete "chlorobenzene" from lines 3 and 4 on page 20.

(6) Same, page 22, line 19, "trifluoromethyl" is corrected to "all 1 trifluoromethyl phenyl".

(7) Insert "Acid" next to "1 Inglobil" on page 34, line 3.

(8) Delete page 37 (continued from Table 2) and insert a separate table (compound numbers 31 to 41, comparative drugs A and B, and untreated group) in its place.

(9) Insert "1560" after "New Call" in the first line of page 39.

+10) Ibid., page 39, line 2" 560, J
Delete.

Claims (1)

[Claims] 1. General formula (wherein R represents a lower alkyl group, m represents an integer of 1 to 2, X represents a lower alkyl group, a herogone atom or a trifluoromethyl group, and n is an integer of O to 2). 2, general formula (wherein R represents a lower alkyl group, rnFi, l~2
Cyclohexenyl acetic acid, represented by the integer of 1, and its reactive conductor and the general formula (where X represents a lower alkyl group, a halocarbon atom or a hatrifluoromethyl group, A method for producing an alkyl-substituted cyclohexenyl acetamide derivative represented by the general formula (wherein RXm%, 8. General formula Rm A herbicide characterized by containing an alkyl-substituted cyclohexenyl acetamide derivative represented by (integer) as an active ingredient.