JPS61210069A - Teraconic acid imide derivative and herbicide containing said derivative as active component - Google Patents

Abstract

NEW MATERIAL:The compound of formula I [R is lower alkyl or lower alkenyl substituted with substituent group selected from H, 1-4C alkyl, lower alkenyl, lower alkynyl, cycloalkyl, halogen, cyano, OH, lower alkoxy, lower alkylthio, epoxy, (substituted) aromatic hydrocarbon residue, etc.]. EXAMPLE:N-(4-chloro-5-hydroxyphenyl)-teraconic acid imide. USE:Highly selective herbicide. It exhibits strong herbicidal activity against a wide variety of weeds in paddy field or plowed land. It is useful as a herbicide of the field of cultivation plants such as rice, wheat, corn, soybean, cotton, etc., for presprouting or post-sprouting application. It is effective at a low rate of application and is harmless to mammals, fish and shellfish. PREPARATION:The compound of formula I can be produced e.g. by reacting the substituted aniline of formula II with teraconic acid of formula III in the absence of a solvent or in an inert high-boiling solvent such as o-chlorobenzene under heating at 130-200 deg.C.

Description

Detailed Description of the Invention (Industrial Application Field) The present invention provides N-substituted phenyl-teraconic acid imide derivatives and The invention relates to a highly selective herbicide containing the same as an active ingredient.

(Prior Art) It is well known that N-substituted phenyl-5,4,5,6-titrahytro7fiAp acid imide derivatives exhibit herbicidal activity as imide herbicides (
For example, see Japanese Patent Publication No. 4a-11940).

However, although these imide herbicides generally exhibit strong herbicidal activity, they lack selectivity and are of no value as practical herbicides.

By the way, ordinary herbicides have strong herbicidal power and high selectivity, as well as low toxicity to warm-blooded animals, and can be commonly used throughout the entire growing season of crops. It is considered ideal to have the requirements of decomposing as quickly as possible and not contaminating the soil, but no herbicide that satisfies these requirements is known yet.

(Problems to be Solved by the Invention) Under these circumstances, the present inventors have overcome the drawbacks of conventional herbicides, and have created a herbicide that is harmless to cultivated crops and other harmful substances that coexist with it. A herbicide with selective and strong herbicidal power that can rapidly eliminate all necessary plants, which can be used consistently throughout the growing period of the crop, and which has low toxicity to warm-blooded animals. After conducting extensive research to develop this %N-substituted phenyluteraconic acid imide derivative, it has been found that it satisfies the above requirements and can be applied to rice and rice with a small amount of application.
It was found that this method is effective against a wide variety of cultivated plants such as wheat, corn, soybeans, and cotton, leading to the completion of the present invention.

(Dangerous Means and Effects for Solving the Problems) To put it into perspective, the present invention uses the general formula ('RFi, a hydrogen atom, a linear chain having 1 to 6 carbon atoms, and a branched alkyl group, Straight chain or branched lower alkenyl group, lower alkynyl group, cycloalkyl group, halogen atom, cyano group, hydroxyl group, lower alkoxy group, lower alkylthio group, epoxy group, substituted or unsubstituted aromatic group hydrocarbon group,
1 selected from acyl group, lower alkoxycarbonyl group
represents a straight-chain or branched lower alkyl group or lower alkenyl group substituted with a species or 281 or more substituents.

The above object can be achieved by using N-substituted phenyluteraconic acid derivatives 1 as an active ingredient as herbicides.

In the present gJJ, in addition to introducing a substituent called an inglopylidene group, which is not found in conventional herbicides, by introducing 4-chlor into the substituent of the Hensen ring and a nee-thyl bond at the 5-position, The selectivity for nine cultivated crops, which cannot be solved by conventional imide compounds, has been greatly improved, and it acts effectively as a pre- and post-emergence herbicide in various agricultural crop cultivation areas, and is effective against mammals, fish and shellfish, etc. □It was completely unexpected that it would become a compound that does no harm.

The range of the alkyl group as R in the compound of the present invention is 1 to 6 carbon atoms, and among the specific substituents that R has, examples of halogen atoms include fluorine atom, chlorine atom, and bromine atom. , an iodine atom.

Further, the acyl group may be either aliphatic or aromatic, and examples include an acetyl group, a propionyl group, and a benzoyl group.

Next, specific examples of the compounds of the present invention represented by general formula (I) 1 include N-(4-chloro-5-hydroxyphenyl)-teraconic acid imide, N-(4-chloro-5-methoxy phenyl)-teraconic acid imide, N-(
4-chloro-5-ethoxyphenyl)-teraconic acid imide, N-(4-chloro-3-n-globoxyphenyl)
N-(4-chloro-3-n-butoxyphenyl)-teraconic acid imide % N-('-chloro-5-impropoxyphenyl)-terraconic acid imide, N-(4-chloro- 5-imbutoxyphenyl)-
Terraconimide, N-(4-chloro-3-see-butoxyphenyl)-terraconimide, N-('-chloro-5-71J-chlorooxyphenyl)-terraconimide b N('-chloro-5-crotyloxyphenyl) )−
Terraconimide% N ('-chloro-5-methallyloxyphenyl)terraconimide, N-[4-chloro-3-(1-methyl71Jruoxy]phenyl]-
Terraconimide, N-(4-chloro-5-propargyloxyphenyl)-terraconimide, N-(4-chloro-5-cyclopropyloxyphenyl)-f laconimide% N-('-chloro-5- cyclopentyloxyphenyl)-terraconimide, N-(4-chloro-5-cyclohexyloxyphenyl)-terraconimide, N-[4-chloro-3-(2-fluoroethyloxy)phenylgoteraconimide, N-[4-chloro-3-(2-chloroethyloxy)phenylgoteraconimide, N-[4-chloro-3-(2-bromoethyloxy)phenylgoteraconimide, N-(
4-chloro-3-(2,2,2-)trifluoroethyloxy)phenylgoteraconic acid imide, N-(4-chloro-5-trifluoromethyloxyphenyl)-teracoacid 4 Mid% N (4 -/col-5-difluoromethyloxyphenyl)-terafunimide, N-[
4-chloro-3-(2-cyanoethyloxy)phenylgoteraconic acid imide, N-[4-chloro-3-(1-
cyanoethyloxy) phenylgoteraconic acid imide,
N-(4-chloro-5-cyanomethyloxyphenyl)
-Teraconic acid imide, N-[4-chloro-3-(2-hydroxyethyloxy)phenylgoteraconic acid imide, N-[4-chloro-3-(2-methoxyethyloxy)phenyl]-terraconic acid imide )', N-(4-chloro-3-(2-ethoxyethyloxy)phenylgoteraconic acid imide, N-[4-chloro-3-(2-impropoxyethyloxy)phenylgoteraconic acid imide,
N-[4-chloro-3-(2-methylthioethyloxyphphenyl]-teraconic acid imide, N-[4-chloro-
3-(2-ethylthioethyloxy]phenyl]-teraconic acid imide, N-[4-/Clue 5-(2,3-epoxyprobyloxy)phenylgoteraconic acid imide,
N-[:4-ri0/l/-3-(α-methylbenzyloxy)phenylgoteraconic acid imide, N-(4-/
Chlor-5-benzyloxyphenyl)-terraconimide, N-(4-chloro-5-phenethyloxyphenyl)-terraconimide, N-[4-chloro-3-(p-
chlorobenzyloxy)phenylgoteraconimide%N-('-chloro-3-(1-methoxycarbonylethyloxy)phenyl]-terraconimide)',N-[
4-/Clue 5-(1-ethoxycarbonylethyloxy)phenylgoteraconic acid imide, N-(4-chloro-5-methoxycarbonylmethyloxyphenyl)-teraconic acid imide, N-(4-chloro-5- ethoxycarbonylmethyloxyphenyl)-terraconic acid imide%N
('-Chloro-5-methylcarbonylmethyloxyphenyl)-Teracorm)', N-(a-chloro-5-
phenylcarbonylmethyloxyphenyl)-terraconic acid imide%N-('-chloro-5-n-amyloxyphenylene/l/) -y 5conic acid imide)', N-(4-
Chlor-5-isoamyloxyphenyl)-teraconic acid imide, N-[4-dichloro-3-(1-methoxy-1
-methoxycarbonylmethyloxy)phenylgoteraconic acid imide and the like.

These compounds can be produced, for example, by any of Method A, Method B, and Method C below.

Method A: (II) (1) (In the formula, R has the same meaning as above) Substituted aniline represented by 2〇 and teraconic acid are heated at about 130C to about 2000C in a solvent-free or inert high-boiling solvent.
．． The compound of the present invention represented by formula (I) can be obtained by heating preferably to about 140C to about 170C. Examples of the solvent used here include O-dichlorobenzene.

Method B: (wherein R has the same meaning as above) Substituted aniline represented by formula (JI) and teraconic anhydride g
IJ is heated at about 100 C to about 200 C without a solvent or in an inert high boiling point solvent such as acetic acid or 0-dichlorobenzene.
, preferably about 120C to about 170C. However, this reaction is a dehydration ring-closure reaction through an amide to an imide.The first amidation reaction is carried out in the presence of a solvent under mild conditions, and after removing the solvent, the reaction is carried out under mild conditions using a dehydrating agent. This can also be done by ring closure with .

Solvents used include ether solvents such as tetrahydrofuran and dioxane, aromatic solvents such as toluene, 710 hydrogenated hydrocarbon solvents such as chloroform, and aprotic solvents such as N,N-dimethylformamide and dimethyl sulfoxide. Examples include polar solvents, and in some cases, water can also be used as a solvent.

Further, as a dehydrating agent, acetic anhydride/sodium acetate, thionyl chloride, etc. can be used.

Method C: (IID QV) CI) (wherein,
R/Ii has the same meaning as above, X is a halogen atom, M
represents an alkali metal atom. ) N-substituted phenyl-teraconic acid imide derivative of formula (IIT) and formula (I
By reacting the halide represented by V) in the presence of a solvent such as acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, etc. at room temperature to 10 DC, preferably 50 to 80 C, the formula (D
The compound of the present invention represented by can be obtained. In addition to the above, examples of reaction solvents include tetrahydrofuran and 18-
In addition to CROWN-6 as a phase transfer catalyst, the following system also gives good results.

Next, the herbicidal effect of the compounds of the present invention will be explained using weed control in paddy rice as an example. 1. The compounds of the present invention can be applied over a wide range of periods from before to after transplanting of paddy rice, and especially during the year in paddy fields. Shows strong herbicidal action against sexual weeds. On the other hand, at the effective dose of the compound of the present invention applied to weeds, almost no phytotoxicity is observed in paddy rice. Furthermore, the compound of the present invention is
It also shows strong herbicidal activity against perennial weeds that grow in rice fields, such as firefly and cypress. The general usage amount of the compound of the present invention for paddy rice is 0.5 to 300.
f/10 a, particularly preferably 2 to 100
It shows excellent herbicidal effect at the dose of f710B.

The compounds of the present invention exhibit extremely strong herbicidal activity against upland weeds other than paddy field weeds. The compound of the present invention is, for example,
Broad-leaved weeds such as goldenweed, Japanese knotweed, Japanese knotweed, chickweed, and bindweed;
It exhibits strong herbicidal activity against various weeds such as Poaceae weeds such as Sparrow grass at low doses. The compound of the present invention is characterized by a high degree of selectivity in pre- and post-emergence treatments for broad-leaved crops such as soybeans and cotton, and legume crops such as rice, corn, and wheat. Further, the compound of the present invention can be used as a herbicide for pastures, orchards, lawns, and non-agricultural lands by taking advantage of its wide herbicidal range and strong herbicidal power.

The compounds of the present invention can be used in a wide range of application rates, for example in an amount of 0.5 to 600 f1 per 10 ares, preferably 2 to 100 f1.

When actually using the compound of the present invention, the active substance itself can be sprayed, and f7'? -1 Irrigation agents, emulsions, granules,
Any formulation form such as powder can be used.

In preparing these pharmaceutical products, solid carriers include, for example, mineral powders (kaolin, bentonite, clay, montmorillonite, Merck, diatomite, mica, vermiculite, ceracola, calcium carbonate, phospholime, etc.), vegetable powders, etc. quality powders (soybean flour, wheat flour, wood flour, tobacco flour, starch, crystalline cellulose, etc.), polymer compounds (petroleum resins, polyvinyl chloride, ketone resins, etc.), and
Alumina, waxes, etc. can be used.

Examples of liquid carriers include alcohols (methanol, ethanol, butanol, ethylene glycol, benzyl alcohol, etc.), aromatic hydrocarbons 51[()
toluene, benzene, xylene, etc.), chlorinated hydrocarbons (chloroform, quaternary carbon, monochlorobenzene, etc.), ethers (dioxane, tetrahydrofuran, etc.), ketones (acetone, methyl ethyl ketone, cyclohexanone, etc.), esters (acetic acid (ethyl, butyl acetate, etc.), acid amides (N,N-dimethylacetamide, etc.), nitriles (acetonitrile, etc.), ether alcohols (ethylene glycol ethyl ether, etc.), or water.

As the surfactant used for the purpose of emulsification, dispersion, diffusion, etc., any of nonionic, anionic, cationic, and amphoteric surfactants can be used. Examples of surfactants that can be used in the present invention include polyoxyethylene alkyl ether, polyoxyethylene alkylaryl needle, polyoxyethylene fatty acid ester, nrubitan fatty acid ester, polyoxyethylene sorbitan fatty acid ester, oxyethylene Polymer, oxypropylene polymer, polyoxyethylene alkyl phosphate, fatty acid salt, alkyl sulfate, alkyl sulfonate, alkylaryl sulfonate, alkyl phosphate, polyoxyethylene alkyl sulfate, quaternary ammonium These include salts, oxyalkylamines, etc., but needless to say, they are not limited to these. Next, gelatin, casein, sodium alginate, starch, agar, polyvinyl alcohol, etc. can be used as adjuvants, if necessary.

Furthermore, the compound of the present invention can be used in combination with other herbicides in order to improve its effectiveness as a herbicide, and a synergistic effect can be expected in some cases. For example, the following components can be used together.

Phenoxy herbicides 2.4-dichlorophenoxyacetic acid: 2-methyl-4-chlorophenoxyacetic acid nibutyl-2-(4-(3-)lifluoromethyl-2-pyridyloxy)phenoxyfupropionate (each ethyl-2-(4-(6-chloro-2-quino-zalinyloxy)phenoxyfupropionate);

(B) Diphenyl ether-based IE removing agent 2.4-dichlorophenyl-4'-nitrophenyl ether; 2,
4.6-) Dichlorophenyl-4'-nitrophenyl ether; 2,4-dichlorophenyl-4'-nitrophenyl 3
'-Methoxyphenyl ether; 2,4-dichlorophenyl-5'-methoxycarbonyl-47-nidrophenyl ether; 2-/Rolow 4-) IJ fluoromethylphenyl-3'-ethoxy-4'-nitrophenyl Ether; 5-(2-chloro-4-()!Jfluoromethyl)phenoxy-2-nitrobenzoic acid sodium salt, etc.

(0 triazine herbicide 2-chloro-4,6-pisethylamino-1,3.5-
) IJ azine; 2-chloro-4-ethylamino-6
-Ituprobylamino1. ! , 5-) riazine; 2-
Methylthio-4,6-pisethylamino-1,3゜5-
such as triazines.

(2) Urea herbicide 5-(3,4-dichlorophenyl)-,1,1-dimethylurea: 3-(3,4-dichlorophenyl)-
1-methoxy-1-methylurea: 3-(α, α, α-
trifluoro m-)dyl) -1,1-dimethylurea:3-(4-(4-methylphenethyloxy)phenyl]-1-methoxy1-methylurea:3-(5-1
-butyl-3,4-thiadiazol-2-yl)-4-
Hydroxy-1-methyl-2-imidazolitone and the like.

[Yes]) Carbamate herbicide isofuropyru-N-(3-chlorophenyl)carbamate, methyl-N-(3*4-dichlorophenyl)
Carbamate; 4-chloro-2-butynyl-N-(3-
chlorphenyl) carbamate, etc.

(No) Thiol carbamate herbicide S-ethyl-N,N-hexamethylenethiol carbamate: 5-(4-chlorobenzyl)-N,N-diethylthiol carbamate: S-ethyldipropylthiol carbamate, etc.

(2) Anilide herbicide 3.4-Dichloropropionanilide: N-methoxymethyl-2',6'-diethyl-2-chloroaceto72lide;2-chloro-2',6'-diethyl-N- (buto-dimethyl)-acetanilide: 2-chloro-21,bl
-Diethyl-N-(70,N$diethyl)-acetanilide: α-(2-naphthoxy)propionanilide, etc.

(b) Uracil herbicide 5-bromo-3-sec-butyl-6-methyluracil: 3-cyclohexyl-5,6-trimethyleneuracil, etc.

(I) Dipyridinium salt herbicides 1.1'-dimethyl-4,4'-diviridinium dichloride; t,1'-ethylene-2,21-diviridinium dipromide and the like.

(J) Phosphorus herbicide N-(phosphonomethyl)glycine:〇-ethyl-Q-(
2-2) o-5-methyl 7z-nyl)-N-butylphosphoramide thioate; O-methyl-〇-(2-nido-o-4-methylphenyl)-N-isopropyl phosphoramide thioate: 5-(2-Methyl-1,1-piperidylcarbonylmethyl)-0,0-di-n-propyldithiophosphate: (2-methyl-4-methylphosphinobutyryl)-tinylalanine monosodium salt Such.

(6) Toluidine herbicide α,α,α-trifluoro2,6-sinitro N,N
-dibu-avir-p-)luidine: N-(cycloflovirmethyl)-α,α,α-trifluoro2,6-dinitro-N-propyl-p-toluidine, etc.

(L) Other herbicides 5-1-butyl-3-(2,4-dichloro-5-impropoxyphenyl) -1,! 1,4-oxacyasily/-2-one; 5-improvir-2,1,3-benzothiacyazino 7-4.2.2-dioxide: 2-(α
-naphthoxy)-N,N-diethylpropionamide:
3-amino-2,5-dichlorobenzoic acid; 4- (2
,4-dichlorobenzoyl)-1,3-dimethylpyrazol-5-yl-p-toluenesulfonate:2-chloro-N-((4-methoxy-6-methyl-1,5,5
-triazin-2-yl)aminocarbonyl]benzenesulfonylamide; 2-((4,6-cymethoxypyrimidin-2-yl)aminocarbonylaminosulfonylmethyl)benzokashun methyl ester: 1lJ-(1-methyl- 1-phenylethyl)-2-7"lomo5,5-')
if Luptanamide: 2-(1-(N-aryoloxyamino)butylidene 4-methoxycarbonyl-5,5
-dimethylcyclohexane-1,5-dione sodium salt: 2-(1-<ethoxyimino)butyl)-5-(2
-ethylthiopropyl)-3-hydroxy-2-cyclohexane-1-onato.

The above herbicides are merely examples, and it goes without saying that other herbicides that can be used in combination with the compound of the present invention are not limited to these. The herbicide of the present invention can also be used in combination with pyrethroid insecticides, other insecticides, fungicides, plant regulators, microbial agents, and fertilizers.

(Example) Next, the present invention will be explained in further detail by reference examples regarding the production of the present compound and examples showing the formulation and effect of the present compound as a herbicide.

Example 1 Production of N-(4-chloro-5-hy)”-xyphenyl)-terraconic acid imide (compound 5) Terraconic anhydride 11
1 and 4-chloro-5-aminephenol 11? was dissolved in 250% acetic acid and heated under reflux for 5 hours. After the reaction, acetic acid was distilled off under reduced pressure and purified by column chromatography (solvent: 10 to 7 tons of toluene), with a melting point of 164.8.
Yellow-white crystals 14f of N-(4-chloro-5-hydroxyphenyl)-teraconic acid imide of ~165.7C were obtained.

Example 2 N-(4-chloro-5-propargyloxyphenyl)
-Preparation of teraconic acid imide (compound 7) Potassium salt of N-(4-chloro-5-hydroxyphenyl)-terraconic acid imide 1,5 f/ (!: Propargyl bromide 0.61 is dissolved in tetrahydrofuran, 18- 0611 of Crown-6 was added and stirred for 3 hours at 40-soC. After the reaction was completed, tetrahydrofuran was distilled off under reduced pressure and purified by column chromatography (solvent: toluene + acetone), with a melting point of 161.5- 162.2 C N-(4-chloro-5-propargyloxyphenyl)
- Obtained 0.77 yellowish white crystals of teraconic acid imide.

Example 3 Various N-substituted phenyl-teraconic acid imides were prepared from the corresponding raw materials in the same manner as in the previous examples.

Table 1 shows the physical properties and analytical values of these compounds. The viscous liquid shown in the physical properties column of Table 1 is the property at room temperature during synthesis.

In addition, elemental analysis was performed using MT-5 type (Yanagimoto g), 'H-N
MR analysis was performed using PNX-6D model (manufactured by Nippon Seiko).

Example 4 Formulation Example 1 (Irrigation agent) 25 parts by weight of the compound of the present invention, 5 parts by weight of Nlubol 5039 (manufactured by Toho Chemical Industry Co., Ltd., trade name), and Merck 7
Thoroughly crush and mix 1 part of 0g to prepare a wettable powder.

Formulation example 2 (emulsion) Compound of the present invention 5-layered portion, Nluball 3005X (manufactured by Toho Chemical Industry Co., Ltd.) 10-layered portion, n-fi/-le 45
Parts by weight and parts by weight of xylene are thoroughly mixed to form an emulsion.

Formulation example 5 (granules) 1 part by weight of the compound of the present invention, 45 parts by weight of bentonite, pV
-44-fold pupil, ligninsulsodium 5ffi
11 parts and 5 parts of sodium dodecylbenzenesulfonate
Parts by weight are thoroughly ground and mixed, water is added, and the mixture is thoroughly kneaded, followed by granulation and drying to form granules.

Formulation Example 4 (Powder) 1 part by weight of the compound of the present invention and 99 parts by weight of clay are thoroughly ground and mixed to form granules.

The amount of the herbicide of the present invention to be used varies depending on the method of use, place of use, and type of target weed, but it is usually sufficient to use an amount of 2 to 10 Of (active ingredient) per 10 ares.

Usage Example 1 A paddy soil filled with 1/5,000 Rbot) K was prepared in a greenhouse. For rice, seedlings at the 3-leaf stage are grown in the soil surface layer 2-5-
It was transplanted to In addition, for Japanese barnyard grass, Japanese grasshopper, annual broad-leaved weed seeds, and azalea, a method was used in which the seeds were mixed with dry paddy soil and mixed into the surface layer. Furthermore, as a perennial weed, 1. I sowed firefly seeds. For chemical treatment, barnyard grass is treated with 1.
At the 5-2.0 leaf stage, an emulsion of a predetermined concentration (Formulation Example 2) was dropped with a pipette. After 21 days of drug teaching, the degree of chemical damage to rice and weed control ability was observed. The results are shown in Table 20:
No effect 2nd vote Example 2 A 17-liter pot filled with field soil was prepared in a greenhouse. Seeds of soybean, corn, crabgrass, Japanese knotweed, and Japanese knotweed were sown in each pot.

The treatment was carried out by applying 10 y per 10 are using a sickle for 24 hours after sowing. The spraying method was as follows: emulsion (formulation 2) of a predetermined m degree was diluted with 15 tons of water per area, and the mixture was sprayed using a glass sprayer. After the chemical treatment, the degree of weed control ability was observed on the 14th day, and the degree of chemical damage to the crops was observed on the 30th day. The results are shown in Table @3.

Note that the criteria in the table are the same as in Use Example 1.

Claims (2)

[Claims] (1) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R is a hydrogen atom, a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched lower alkenyl group,
lower alkynyl group, cycloalkyl group, halogen atom,
Substituted with one or more substituents selected from a cyano group, a hydroxyl group, a lower alkoxy group, a lower alkylthio group, an epoxy group, a substituted or unsubstituted aromatic hydrocarbon group, an acyl group, and a lower alkoxycarbonyl group. represents a straight-chain or branched lower alkyl group or lower alkenyl group. ) An N-substituted phenyl-teraconic acid imide derivative represented by: (2) General formula ▲ Numerical formula, chemical formula, table, etc. ▼ (I) (In the formula, R is a hydrogen atom, a straight chain or branched alkyl group having 1 to 6 carbon atoms, a straight chain or branched lower alkenyl group,
lower alkynyl group, cycloalkyl group, halogen atom,
Substituted with one or more substituents selected from a cyano group, a hydroxyl group, a lower alkoxy group, a lower alkylthio group, an epoxy group, a substituted or unsubstituted aromatic hydrocarbon group, an acyl group, and a lower alkoxycarbonyl group. represents a straight-chain or branched lower alkyl group or lower alkenyl group. ) A herbicide containing an N-substituted phenyl-teraconic acid imide derivative as an active ingredient.