JPH0680663A - N-acyldihydroxyquinoline derivative and herbicide containing the same derivative as active component - Google Patents

Abstract

PURPOSE:To provide the subject new compound useful as a herbicide. CONSTITUTION:A compound of formula I [R<1> to R<3> are each H, a 1 to 6C alkyl, a halogen, a 1 to 6C alkoxy, phenyl, phenoxy, etc.; R<4> and R<5> are each H or a 1 to 6C alkyl or a 2 to 5C alkylene may be formed by mutually bonding both the terminals of R<4> and R<5>; R<6> is H, a halogen, a (1 to 6C alkyl)amino, etc., X is CH or N], e.g. 6-chloro-2,2-dimethyl-1-nicotinoyl-1,2-dihydroquinoline. The compound of formula I can be obtained by reacting a dihydroquinoline derivative of formula II with an aromatic halide derivative of formula III (W1 is a halogen).

Description

Detailed Description of the Invention

[0001]

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

[0002]

OBJECT OF THE INVENTION It has been known so far that various compounds can be used as active ingredients of herbicides, but it cannot be said that they are necessarily satisfactory as herbicides.

[0003]

The present inventors have found that an N-acyldihydroquinoline derivative represented by the following general formula 4 is an excellent compound as a herbicide, and completed the present invention. That is, the present invention is represented by the general formula

[0004]

[Chemical 4] [In the formula, R ¹ , R ² and R ³ are the same or different and each represents a hydrogen atom, a C1-C6 alkyl group, a halogen atom,
C1-C6 alkoxy group, halo C1-C6 alkyl group,
Halo C1-C6 alkoxy group, (C1-C6 alkoxy) carbonyl group, C1-C6 alkylthio group, C1-
C6 alkylamino group, di (C1-C6 alkyl) amino group, phenyl group or phenoxy group, wherein R ⁴ and R ⁵ are the same or different and each represents a hydrogen atom or C1-
Represents a C6 alkyl group or represents a C2-C5 alkylene group in which R ⁴ and R ⁵ are bonded at the terminal, and R ⁶ represents a hydrogen atom, a halogen atom, an amino group, a C1-C6 alkylamino group,
Represents a di (C1-C6 alkyl) amino group, a (C1-C6 alkoxy) carbonylamino group, a cyano group, or has the general formula

[0005]

Embedded image —C (═O) —Y—R ⁷ (Y represents an oxygen atom or a sulfur atom, R ⁷ represents a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, Halo C1-C10 alkyl group, halo C2-C10 alkenyl group, halo C2-C
10 alkynyl group, C3-C10 cycloalkyl group, C
3-C10 cycloalkenyl group, C1-C10 alkoxy C1-C10 alkyl group, C1-C10 alkylamino C1-C10 alkyl group, di (C1-C10 alkyl) amino C1-C10 alkyl group, furyl C1-C1
0 alkyl group, thienyl C1-C10 alkyl group, C1
Represents a C10 alkylamino group, a di (C1-C10 alkyl) amino group, or represents a (C1-C6 alkoxy) carbonyl group, a halogen atom or a phenyl group which may be substituted with a C1-C6 alkyl group. Or a (C1-C6 alkoxy) carbonyl group,
Represents a phenyl C1-C6 alkyl group which may be substituted with a halogen atom or a C1-C6 alkyl group,
Alternatively, it represents a group represented by -N = CHR or -N = CRR '. (Wherein R and R ′ are the same or different and each represents a C1-C10 alkyl group)) or are represented by the general formula 6

[0006]

[Chemical 6] (R ⁸ and R ⁹ are the same or different and are a hydrogen atom, C1-
C6 alkyl group, C2-C6 alkenyl group, C2-C6
Alkynyl group, halo C1-C6 alkyl group, halo C2-
C6 alkenyl group, halo C2-C6 alkynyl group, C3
-C6 cycloalkyl group, C3-C6 cycloalkenyl group, amino group, C1-C6 alkylamino group or di (C1-C6 alkyl) amino group, or substituted with a halogen atom or a C1-C6 alkyl group Or a phenyl C1-C6 alkyl group which may be substituted with a halogen atom or a C1-C6 alkyl group. ), X represents CH or N. ] The dihydroquinoline derivative shown by these and the herbicide which makes it an active ingredient are provided.

In R ¹ , R ² , R ³ , R ⁴ , R ⁵ , and R ⁶ , the number of carbon atoms is generally preferably 1 to 3, and in R ⁷ , the number of carbon atoms is generally preferably 1 to 6. That is, R ¹ ,
R ² and R ³ are the same or different and are a hydrogen atom, C
1-C3 alkyl group, halogen atom, C1-C3 alkoxy group, halo C1-C3 alkyl group, halo C1-C3 alkoxy group, (C1-C3 alkoxy) carbonyl group,
A C1-C3 alkylthio group, a C1-C3 alkylamino group, a di (C1-C3 alkyl) amino group, a phenyl group or a phenoxy group is preferable, and R ⁴ and R ⁵ are the same or different and are a hydrogen atom or a C1-C3 alkyl group. ,
Alternatively, a C2-C3 alkylene group in which R ⁴ and R ⁵ are bonded at the terminal is preferable, and R ⁶ is a hydrogen atom, a halogen atom, an amino group, a C1-C3 alkylamino group, di (C1-C3
An alkyl) amino group, a (C1-C3 alkoxy) carbonylamino group, a cyano group, or a group represented by the general formula 5 or 6 is preferable. In the general formulas 5 and 6, R ⁷ is hydrogen atom, C1-C6 alkyl group, C2-
C6 alkenyl group, C2-C6 alkynyl group, halo C1
-C6 alkyl group, halo C2-C6 alkenyl group, halo C2-C6 alkynyl group, C3-C6 cycloalkyl group, C3-C6 cycloalkenyl group, C1-C6 alkoxy C1-C6 alkyl group, C1-C6 alkylamino C1- C6 alkyl group, di (C1-C6 alkyl) amino C1-C6 alkyl group, furyl C1-C6 alkyl group, thienyl C1-C6 alkyl group, C1-C6 alkylamino group, di (C1-C6 alkyl) amino group Or a (C1-C6 alkoxy) carbonyl group,
Represents a phenyl group which may be substituted with a halogen atom or a C1-C6 alkyl group, or (C1-
C6 alkoxy) carbonyl group, a phenyl C1-C6 alkyl group which may be substituted with a halogen atom or a C1-C6 alkyl group, or -N = CHR
Alternatively, a group represented by -N = CRR '(wherein R and R'are the same or different and each represents a C1-C6 alkyl group) is preferable. Further, R ⁴ and R ⁵ are
The same or different, a C1-C3 alkyl group is preferable, and a methyl group is more preferable. Conversion 7

[Chemical 7] The group represented by

[Chemical 8] The group represented by is preferable, and as R ⁶ , a hydrogen atom, a halogen atom, a cyano group or a group represented by the general formula 5 or 6 is preferable, and a group represented by the general formula 5 or 6 is more preferable. R ¹ is preferably 6-position substitution,
A halogen atom, a C1-C3 alkyl group or a phenyl group is preferable, and a halogen atom is more preferable. R ² and R ³ are preferably hydrogen atoms.

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , R ⁶ , R
⁸ , R ^{9 represents} an alkyl group, a haloalkyl group, an alkylthio group, an alkylamino group, a dialkylamino group,
As the alkyl moiety of the phenylalkyl group, for example,
Methyl group, ethyl group, n-propyl group, i-propyl group, n-
Examples thereof include a butyl group, sec-butyl group, tert-butyl group, n-hexyl group and the like. An alkoxy group, a haloalkoxy group,
Examples of the alkoxy moiety of the alkoxycarbonyl group and the alkoxycarbonylamino group include a methoxy group, an ethoxy group, an n-propoxy group, an i-propoxy group, an n-butoxy group and a hexyloxy group. Examples of the alkenyl group and the alkenyl portion of the haloalkenyl group include a vinyl group, an allyl group, a 1-butenyl group, a 2-butenyl group, a 3-butenyl group, a 2-pentenyl group, a 3-pentenyl group and a 2-hexenyl group. Is mentioned. Examples of the alkynyl group and the alkynyl group portion of the haloalkynyl group include an ethynyl group, a propargyl group, a 1-butynyl group,
Examples thereof include a 2-butynyl group, a 2-pentynyl group, a 3-pentynyl group and a 2-hexynyl group. Examples of the cycloalkyl group include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group and the like. Examples of the cycloalkenyl group include a cyclopropenyl group, a cyclobutenyl group, a cyclopentenyl group, a cyclohexenyl group and the like. Examples of the halogen moiety of the halogen atom, haloalkyl group, haloalkenyl group, haloalkynyl group and haloalkoxy group include a fluorine atom, a chlorine atom and a bromine atom. More specifically, examples of the haloalkyl group include a 2-chloroethyl group, a 2-bromoethyl group, a 3-fluoropropyl group, a 2-chloropropyl group, a 4-chlorobutyl group and a 6-chlorohexyl group. Examples of the haloalkoxy group include fluoromethoxy group, dibromomethoxy group, trifluoromethoxy group, 1,1-dichloroethoxy group, 1-chloro, 2
Examples include -bromobutoxy group and 1,1,2,2-tetrafluorohexyloxy group. Examples of the haloalkenyl group include 1-chlorovinyl group, 3-chloroallyl group, 5-bromo-2-pentenyl group, 6-fluoro-
Examples thereof include 2-hexenyl group and 5,5,5-trifluoro-2-pentenyl group. Examples of the haloalkynyl group include a 2-chloroethynyl group and 5-bromo-2.
-Pentynyl group, 6-fluoro-2-hexynyl group,
Examples include 5,5,5-trifluoro-2-pentynyl group and the like. Examples of the alkylamino group include, for example, a methylamino group, an ethylamino group, a propylamino group, a hexylamino group, and the like, and examples of the dialkylamino group include:
Examples thereof include a dimethylamino group, a methylethylamino group, a dipropylamino group and a methylhexylamino group. Examples of the phenyl group which may be substituted with a halogen atom, an alkyl group or an alkoxycarbonyl group include a phenyl group, a 2-methylphenyl group, a 3-ethylphenyl group, a 4-hexylphenyl group and a 2,6-dimethylphenyl group. Group, 2-fluorophenyl group, 2-chlorophenyl group, 3-bromophenyl group, 2,4-dichlorophenyl group, 2,4,5-trichlorophenyl group, 2-chloro-4-methylphenyl group, 2-methoxycarbonylphenyl Group, 3-ethoxycarbonylphenyl group, 5-hexyloxycarbonylphenyl group and the like. Examples of the alkylene group include ethylene group, tetramethylene group, pentamethylene group and the like.

In R ⁷ , the alkyl moiety of an alkyl group, a haloalkyl group, an alkoxyalkyl group, an alkylaminoalkyl group, a dialkylaminoalkyl group, a phenylalkyl group, a furylalkyl group, a thienylalkyl group, an alkylamino group or a dialkylamino group. In addition to the above specific examples, examples thereof include a heptyl group, an octyl group, a nonyl group, and a decyl group. Examples of the alkenyl group of the alkenyl group and the haloalkenyl group include a heptenyl group, an octenyl group and a decenyl group, in addition to the above specific examples. The alkynyl group and the alkynyl moiety of the haloalkynyl group include, in addition to the above specific examples, for example,
Examples thereof include a heptynyl group, an octynyl group and a decynyl group. As the haloalkyl group, other than the above specific examples, for example, a 2-fluoroheptyl group, a 3-chlorooctyl group,
2-bromodecyl group etc. are mentioned. As the haloalkenyl group, in addition to the above specific examples, for example, 1-chloro-2
-Heptenyl group, 3-chloro-2-octenyl group, 5-
A bromo-2-decenyl group, a 6-fluoro-2-heptenyl group, a 5,5,5-trichloro-2-heptenyl group and the like can be mentioned. As the haloalkynyl group, other than the above specific examples, for example, a 2-chloro-2-heptinyl group, a 3-bromo-2-octynyl group, a 5-chloro-2-decynyl group, a 6-fluoro-2-heptynyl group. , 5,5,5-trifluoro-2-heptinyl group and the like. Examples of the cycloalkyl group include, in addition to the above specific examples, a cycloheptyl group, a cyclooctyl group, a cyclodecyl group, and the like. Examples of the cycloalkenyl group include, in addition to the above specific examples, a cycloheptenyl group, a cyclooctenyl group, a cyclodecenyl group, and the like. Examples of the alkoxyalkyl group include a methoxymethyl group, an ethoxymethyl group, a 1-methoxyethyl group, a 2-methoxyethyl group, a 3-ethoxypropyl group, a 4-n-butoxybutyl group, and a 6-n-hexyloxyhexyl group. , 2-ethoxyheptyl group, 3-i-butoxydecyl group, 4-n-decyloxybutyl group and the like. Examples of the alkylaminoalkyl group include a methylaminomethyl group, an ethylaminomethyl group, a butylaminomethyl group, a hexylaminoethyl group, an octylaminoethyl group, a methylaminopropyl group, an ethylaminohexyl group, and a methylaminodecyl group. Examples of the dialkylaminoalkyl group include a dimethylaminomethyl group, a diethylaminomethyl group, a methylbutylaminomethyl group, a methylhexylaminoethyl group, a dipropylaminobutyl group, a diethylaminohexyl group, and a dimethylaminodecyl group. To be Examples of the alkylamino group include, in addition to the above specific examples, a heptylamino group, an octylamino group, a decylamino group, and the like, and examples of the dialkylamino group include a diheptylamino group, a methyloctylamino group, and ethyldecyl. An amino group etc. are mentioned. -N = The CHR group, e.g., -N = CHCH _{3,
-N = CHC 2 H 5, -N} = CHC 3 H 7, -N = CH
_{C 6 H 13, -N = CHC} 10 H 21, as is -N = CRR 'group, for _{example, -N = C (CH 3)} 2, -N = C (C 2 H 5)
_{2, -N = C (CH 3} ) C 2 H 5, -N = C (CH 3)
_{C 6 H 13, -N = C} (CH 3) C 10 H 21 group, and the like.

Examples of the phenyl group or phenylalkyl group which may be substituted with an alkoxycarbonyl group, a halogen atom or an alkyl group include, in addition to the above-mentioned specific examples, for example, a 3-methoxycarbonylphenyl group and 4-
i-propoxycarbonylphenyl group, 3-hexyloxycarbonylphenyl group, phenyl group methyl group, phenyl group ethyl group, phenyl group hexyl group, phenyldecyl group, 2-methoxycarbonylphenylethyl group, 2-ethoxycarbonylphenylbutyl group, 2-n-propoxycarbonylphenylmethyl group, 2-hexyloxycarbonylphenylhexyl group, 2-methoxycarbonylphenyldecyl group, 2-fluorophenylbutyl group, 3-
Fluorophenylmethyl group, 2-chlorophenylhexyl group, 3-bromophenyldecyl group, 2,4-dichlorophenethyl group, 2,4,5-trichlorophenylethyl group, 2-methylphenylethyl group, 3-ethylphenylhexyl group Group, 4-hexylphenylbutyl group, 2-methylphenyldecyl group, 2,6-dimethylphenyl group ethyl group, 2-chloro, 4-methylphenylethyl group, 2
Examples thereof include -fluoro and 4-methoxycarbonylphenylethyl groups.

Next, the manufacturing method will be described in detail. The compound of the present invention has the general formula

[Chemical 9] [In the formula, R ¹ , R ² , R ³ , R ⁴ and R ⁵ have the same meanings as described above. ] The dihydroquinoline derivative represented by

[0012]

[Chemical 10] [In the formula, R ⁶ and X have the same meanings as described above, and W ₁ represents a halogen atom. ] It can manufacture by making it react with the aromatic halide derivative shown by these.
This reaction is usually carried out without solvent or in a solvent in the presence of a dehydrohalogenating agent, the reaction temperature is in the range of room temperature to the boiling point of the solvent, and the reaction time is in the range of 1 to 24 hours. The amount of the reagent is 1 to 3 equivalents for the aromatic halide derivative represented by the general formula 10 and 1 to 5 equivalents for the dehydrohalogenating agent to 1 equivalent of the dihydroquinoline derivative represented by the general formula 9. . When using a solvent, as a solvent that can be used, hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene, aromatic hydrocarbons such as xylene, chloroform, carbon tetrachloride,
Halogenated hydrocarbons such as dichloroethane, chlorobenzene and dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran and diethylene glycol dimethyl ether,
Acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, and other ketones, ethyl formate, ethyl acetate, butyl acetate, and other esters, nitroethane, nitrobenzene, and other nitro compounds, acetonitrile, isobutyronitrile, and other nitriles, pyridine , Tertiary amines such as triethylamine, N, N-diethylaniline, tributylamine and N-methylmorpholine, acid amides such as formamide, N, N-dimethylformamide and acetamide, sulfur compounds such as dimethylsulfoxide and sulfolane, water and the like Alternatively, a mixture thereof can be used. When a dehydrohalogenating agent is used, examples of the dehydrohalogenating agent that can be used include organic bases such as pyridine, triethylamine, N, N diethylaniline, and 4- (N, N dimethylamino) pyridine, sodium carbonate, potassium carbonate, Examples thereof include inorganic bases such as sodium hydride. After completion of the reaction, the reaction solution is added with water and subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, purification by chromatography, distillation, recrystallization, etc. to obtain the desired product. Invention compounds can be obtained.

Further, among the compounds of the present invention, the compound of the general formula 4 in which R ⁶ is a COOH group (referred to as compound I) is represented by the general formula 11

[Chemical 11] [Wherein R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X represent the same meaning as described above, R ¹⁰ represents a C1-C6 alkyl group, C
1-C6 alkenyl group, C1-C6 alkynyl group, halo C1-C6 alkyl group, halo C1-C6 alkenyl group,
Halo represents a C1-C6 alkynyl group, a C3-C6 cycloalkyl group, a C3-C6 cycloalkenyl group, a C1-C6 alkoxy C1-C6 alkyl group, a C1-C6 alkylamino C1-C6 alkyl group, a halogen atom or C1- Represents a phenyl group which may be substituted with a C6 alkyl group, or represents a phenyl C1-C6 alkyl group, a furyl C1-C6 alkyl group or a thienyl C1
Represents a -C6 alkyl group. ] It can also manufacture by hydrolyzing the compound shown by these. This reaction is generally carried out without solvent or in the presence of water, acid or base, in the range of reaction temperature from room temperature to boiling point of solvent, and in reaction time from 5 minutes to 24 hours. The amount of the reagent used is the dihydroquinoline derivative 1 represented by the general formula 11
Water is 1-1000 equivalents, and acids and bases are 0.01-100 equivalents based on equivalents. When a base is used, usable bases include pyridine, triethylamine, N,
Organic bases such as N-diethylaniline, sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate,
Inorganic base such as sodium hydride, sodium methoxy,
Examples thereof include alkali metal alkoxides such as ethoxy sodium. When an acid is used, the acid that can be used is
Examples thereof include Lewis acids such as zinc chloride and aluminum chloride, inorganic acids such as hydrochloric acid, sulfuric acid and nitric acid, and organic acids such as acetic acid and p-toluenesulfonic acid. When a solvent is used, the same solvent as described above can be used as the solvent. After completion of the reaction, the reaction solution is added with water and subjected to usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, purification by chromatography, distillation, recrystallization, etc. to obtain the desired product. Invention compounds can be obtained. Further, among the compounds of the present invention, the compound in which R ⁶ in the general formula 4 is a group represented by the formula 5 or 6 (however, R ⁶ is not a COOH group) is a compound I and an acid halogenating agent. Alternatively, after reacting with an active esterifying agent (reaction (i)),
Then, the reaction product and the compound of the general formula

HYR ⁷ [In the formula, Y and R ⁷ have the same meanings as described above.] However, -YR ⁷ is not a -OH group. ] The compound or general formula 13

Embedded image HNR ⁸ R ⁹ wherein, R ^8, R ⁹ are as defined above. ] It can manufacture also by making it react with the compound shown by (reaction (ii)). In the above reaction (i),
Examples of the acid halogenating agent include thionyl chloride, thionyl bromide, phosphorus trichloride, phosphorus tribromide, phosphorus pentachloride, phosphorus oxychloride, phosgene, oxalic acid dichloride and the like.
Examples of the active esterifying agent include N, N'-dicyclohexylcarbodiimide, N, N'-diisopropylcarbodiimide, and N, N'-disubstituted carbodiimide such as 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride. , Arylsulfonyl chlorides such as 2,4,6, -trimethylbenzenesulphonyl chloride, 2,4,6, -triisopropylbenzenesulfonyl chloride, N, N '
-Carbonyldiimidazole, diphenylphosphoryl azide, N-ethoxycarbonyl-2-ethoxy-1,2
-Dihydroquinoline, N-ethyl-2'-hydroxybenzisoxazolium trifluoroborate, N-ethyl-5-phenylisoxazolium-3'sulfonate and the like. By such a reaction, the compound of the general formula

[Chemical 14] [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X have the same meanings as described above. ] The compound shown by this is produced.

In the above reaction, the substituent W represents a halogen atom when an acid halogenating agent is used, and when an N, N'-disubstituted carbodiimide is used as an active esterifying agent, N, N′-disubstituted-2-isoureido group is represented, and when arylsulfonyl chloride is used, it represents an arylsulfonyloxy group, and N, N ′.
When -carbonyldiimidazole is used, it represents an imidazolyl group, and when diphenylphosphoryl azide is used, it represents an azido group, and N-ethoxycarbonyl-
When 2-ethoxy-1,2-dihydroquinoline is used, it represents an ethoxycarbonyloxy group, and when N-ethyl-2′-hydroxybenzisoxazolium trifluoroborate is used, it is 3 Represents a-(N-ethylaminocarbonyl) -2-hydroxyphenoxy group, N
When using -ethyl-5-phenylisoxazolium-3'-sulfonate,

[Chemical 15] Represents a group represented by. In the reaction system, W is
Conversion 16

[Chemical 16] [In the formula, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and X have the same meanings as described above. ] It can also take the form of the acid anhydride shown. The amount of the acid halogenating agent or active esterifying agent used is usually 1 to 10 equivalents relative to 1 equivalent of the compound I. The amount of the compound represented by the general formula 12 or 13 is usually 1 with respect to 1 equivalent of the compound I.
~ 5 equivalents. The reactions (i) and (ii) can be carried out in the presence of a base, if necessary. Such bases include 1-methylimidazole, 3-nitro-1H-
1,2,4-triazole, 1H-tetrazole, 1H
Examples thereof include organic bases such as -1,2,4-triazole, imidazole, pyridine and triethylamine, and inorganic bases such as potassium carbonate, and the amount thereof is 1 to 20 equivalents relative to 1 equivalent of the compound I. Reactions (i) and (ii)
Is usually carried out in the presence of an inert solvent, such solvents include hexane, heptane, ligroin, aliphatic hydrocarbons such as petroleum ether, benzene, toluene, aromatic hydrocarbons such as xylene, Halogenated hydrocarbons such as chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene, ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran, diethylene glycol dimethyl ether, acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone, etc. Ketones, esters of ethyl formate, ethyl acetate, butyl acetate, etc., nitro compounds such as nitroethane, nitrobenzene, etc.
Nitriles such as acetonitrile and isobutyronitrile,
Tertiary amines such as pyridine, triethylamine, N, N-diethylaniline, tributylamine, N-methylmorpholine, acid amides such as N, N-dimethylformamide, sulfur compounds such as dimethylsulfoxide, sulfolane, etc., or a mixture thereof. Is mentioned. Further, in general, the reaction temperature is 0 ° C. or higher for both reactions (i) and (ii).
It is the boiling point of the solvent and the reaction time depends on the reaction (i) and (ii).
Per 1 hour to 24 hours, and about 1 hour to 48 hours throughout the reactions (i) and (ii). After completion of the reaction, water is added to carry out usual post-treatments such as extraction with an organic solvent and concentration, and if necessary, chromatography, distillation,
The desired compound of the present invention can be obtained by purification by an operation such as recrystallization. The compound of the present invention has optical isomers, and all optical isomers having herbicidal activity are also included in the present invention. In the case of producing the compound of the present invention, the dihydroquinoline derivative represented by the general formula 9 which is a raw material compound is prepared according to Journal of Medicinal Chemistry,
It can be produced according to the method described in 16 251 (1973).

The compound of the present invention has an excellent herbicidal effect,
Some also show excellent selectivity between crops and weeds.
That is, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in the foliage treatment of fields (including ridges, fallow land, etc.) and soil treatment. Polygonum convolvulus, Weed Polygonum, Polygonum convolvulus
ygonum lapathifolium), American scepter (Polygon
um pensylvanicum), Hartade (Polygonum persicari)
a), Rumex crispus, Rumex crispus
(Rumex obtusifolius), Weeds of the purslane family Purslane (Portulaca oleracea) Weeds of the family Caryophyllaceae (Stellaria media) Weeds of the family Schizophyllum (Chenopodium album), Hochigi (Kochia scopar)
ia) Amaranthaceous weeds Amaranthus retroflexus, Aconanthus amaranthus hybridns Brassica weeds Wild radishes Raphanus raphanistrum, Brassica Kaber, Capsella bursa-pa
storis) Leguminous weed American hemlock (Sesbania exaltata), Ebisugusa (Cassia obtusifolia), Florida begger weed (Des
modium tortuosum), white clover (Trifolium repens) mallow weed Abutilon theophrasti, American stag deer (S
ida spinosa) Violet arvensis (Viola arvensis), wild pansies (Viola tricolor) Rubiaceae weeds (Galium aparine) bindweed weeds American morning glory (Ipomoea hederacea)
ea hederacea var.integriuscula), Yellow-faced morning glory (Ipo
moea lacunosa), bindweed (Convolvulus arven)
sis) Lamiaceae weeds (Lamium purpureum)
ium amplexicaure) Weeds of Solanaceae, Datura stramonium, Solanum nigrum, Weeds of Veronica persica and Veronica persica.
eronica hederaefolia) Weeds Asteraceae (Xanthium pensylvanicum), Wild sunflower (Hel
ianthus annuus), dog chamomile (Matricaria inodor)
a), corn marigold (Chrysanthemum segetum),
Forsythia (Matricaria matricarioides), Ragweed
(Ambrosia artemisiifolia), Black ragweed (Ambrosia
trifida), Erioderma canadensis (Erigeron canadensis), weeds (Myosotis arvensis) Eno Kologsa (Set
aria viridis), Achinoe foxtail (Setaria faber)
i), Crabgrass (Digitaria sanquinalis), Crabgrass (Ele
usine indica), Bluegrass (Poa annua), Blackgrass (Alopecurus myosuroides), Oat (Ave)
na fatua), Seiban sorghum (Sorghum halepense),
Wheatgrass (Agropyron repens), Japanese horse chestnut (Bromus)
tectorum), Cynodon dactylon, Panicum dichotomiflorum, Texas Panicum
(Panicum texanum), Shatter cane (Sorghum vulgar
e) Commelina communis Commelina communis Commelina weed Equisetum arvense Cyperus weed (Cyperus iria), Cyperus rot
undus), Cyperus esculentus, and some of the compounds of the present invention are corn (Z
ea mays), wheat (Triticum aestivum), barley (Hor)
deum vulgare), rice (Oryza sativa), soybean (Glycine
max), cotton (Gossypium spp.), sugar beet (Beta vulgar)
is), peanuts (Arachis hypogaea), sunflowers (Helia
nthus annuus), rapeseed (Brassica napus), and other horticultural crops such as flowers and vegetables. Further, the compound of the present invention can effectively weed out various weeds that are problematic in non-tillage cultivation of soybean, peanut, corn and the like. Moreover, some of the compounds of the present invention do not show any harmful phytotoxicity to these crops. In addition, the compound of the present invention has herbicidal activity against various weeds which cause the following problems in the flooding treatment of paddy fields. Weeds of grass family Echinochloa oryzicola Weeds of Sesameaceae Lindernia procumbens Weeds of the family Lythraceae (Rotala indica), Lathyrus serrata (Ammannia)
multiflora) Weeweed (Elatine triandra) Weed weed (Cyperus difformis), Firefly (Scirpus)
juncoides), pine nuts (Eleocharis acicularis), Cyperus serotinus, crocoy (Eleocha)
ris kuroguwai) Weasel weed, Kokonagi (Monochoria vaginalis) Weeds, weed Urikawa (Sagittaria pygmaea), Soda (Sagittaria)
trifolia), Heraomodaka (Alisma canaliculatum), Weed Shiro (Potamogeton distinctus), Weed Seri (Oenan the javanica) In addition, some of the compounds of the present invention cause harmful effects on transplanted rice or direct-seeded paddy rice. Not shown. Further, the compounds of the present invention can control a wide range of weeds that occur in orchards, meadows, lawns, forestry or waterways, canals or other non-agricultural lands.

When the compound of the present invention is used as an active ingredient of a herbicide, it is usually mixed with a solid carrier, a liquid carrier, a surfactant or other auxiliaries for formulation to prepare emulsions, wettable powders, suspending agents and granules. Used as an active ingredient of a herbicide by formulating it into a herbicide or granule wettable powder. In these formulations, the compound of the present invention is used as an active ingredient in a weight ratio of 0.03 to 75%, preferably 0.05 to
Contains 70%. As the solid carrier, kaolin clay,
Mineral powders such as attapulgite clay, bentonite, acid clay, pyrophyllite, talc, diatomaceous earth, and calcite, organic powders such as walnut shell powder, water-soluble organic powders such as urea, inorganic salt powders such as ammonium sulfate and Examples thereof include fine powders of synthetic hydrous silicon oxide and the like, and liquid carriers include methylnaphthalene, phenylxylylethane,
Aromatic hydrocarbons such as alkylbenzene such as xylene,
Alcohols such as isopropanol, ethylene glycol and 2-ethoxyethanol, esters such as dialkyl phthalate, ketones such as acetone, cyclohexanone and isophorone, mineral oil such as machine oil, soybean oil,
Vegetable oils such as cottonseed oil, dimethyl sulfoxide, N, N-dimethylformamide, acetonitrile, N-methylpyrrolidone, water and the like can be mentioned. Surfactants used for emulsification, dispersion, wet extension, etc. include alkyl sulfate ester salts, alkyl sulfonates, alkylaryl sulfonates, dialkylsulfosuccinates, polyoxyethylene alkylaryl ether phosphate ester salts, etc. Nonionic surfactants such as anionic surfactants, polyoxyethylene alkyl ethers, polyoxyethylene alkylaryl ethers, polyoxyethylene polyoxypropylene block copolymers, sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, and the like. . Other auxiliaries for formulation include lignin sulfonate, alginate, polyvinyl alcohol,
Examples include gum arabic, CMC (carboxymethyl cellulose), PAP (isopropyl acid phosphate) and the like. The compound of the present invention is usually formulated and subjected to soil treatment, foliage treatment or flooding treatment before or after emergence of weeds. The soil treatment includes a soil surface treatment, a soil admixture treatment, and the like, and the foliage treatment includes a treatment from above the plant body and a local treatment for treating only the weeds so as not to adhere to the crop.
Further, when used in combination with other herbicides, the herbicidal effect may be enhanced. Furthermore, it can be used by mixing with insecticides, acaricides, nematicides, fungicides, plant growth regulators, fertilizers, soil conditioners and the like. When the compound of the present invention is used as an active ingredient of a herbicide, the amount to be treated varies depending on weather conditions, formulation form, treatment time, method, place, target weed, target crop, etc., but usually 10 g to 10,000 g per hectare, Preferably 20 g to 800
The amount of emulsion, wettable powder, suspension, hydrated granule, etc. is usually 10 liters to 10 liters per hectare.
Dilute with 00 liters of water (if necessary, an auxiliary agent such as a spreading agent is added) for treatment, and granules or the like are usually treated without any dilution. As the auxiliary agent, in addition to the above-mentioned surfactant, polyoxyethylene resin acid (ester), lignin sulfonate, abietic acid salt, dinaphthylmethane disulfonate, crop oil concentrate (crop oil concentrate), soybean oil, Vegetable oils such as corn oil, cottonseed oil, sunflower oil and the like can be mentioned.

[0017]

INDUSTRIAL APPLICABILITY The compound of the present invention has an excellent herbicidal activity against various weeds which are problematic in the soil treatment and foliage treatment of upland fields, and the flooding treatment of paddy fields, and various compounds as an active ingredient of herbicides. It can be used for various purposes.

[0018]

The present invention will be described in more detail below with reference to production examples, formulation examples and test examples, but the present invention is not limited to these examples. First, production examples of the compound of the present invention will be shown. Production Example 1 5.34 g of nicotinic acid chloride hydrochloride was added to methylene chloride 5
Suspended in 0 ml, to which triethylamine 7.56 g
Was added. After stirring for 30 minutes at room temperature, 6-chloro-
2,2-Dimethyl-1,2-dihydroquinoline 3.88
g was dissolved in 20 ml of methylene chloride and added. further,
1.00 g of 4-dimethylaminopyridine was added. After refluxing for 7 hours, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to thin layer chromatography (silica gel, ethyl acetate / hexane (1: 1 (V / V)) to give 6-chloro-2,2-dimethyl-1. - nicotinoyl-1,2-dihydroquinoline (present compound (1)) was obtained _{^{1.01g 1 H-NMR (CDCl 3}} ) δ:. 1.67 (s, 6H) 5.92 (d, 1H, J = 10.0Hz) 6.48 (d, 1H, J = 10.0Hz) 6.25〜7.44 (m, 4H) 7.85〜8.07 (m, 1H) 8.66〜8.86 (m, 2H) Production Example 2 1.43 g of pyrazinecarboxylic acid chloride in 20 ml of methylene chloride. Dissolved, 1.21 g of triethylamine
Was added. After stirring at room temperature for 30 minutes, 6-methyl-
2,2-Dimethyl-1,2-dihydroquinoline 1.73
g was dissolved in 5 ml of methylene chloride and added. Furthermore, 4
-0.3 g of dimethylaminopyridine was added. After refluxing for 7 hours, the reaction solution was poured into water and extracted with ethyl acetate.
The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the obtained residue was subjected to thin layer chromatography (silica gel, ethyl acetate / hexane (1: 1 (V / V)) to give 6-methyl-2,2-dimethyl-1. 0.76 g of -pyrazinecarbonyl-1,2-dihydroquinoline (inventive compound (7)) was obtained ¹ H-NMR (CDCl ₃ ) δ: 1.63 (s, 6H) 2.08 (s, 3H) 5.63 (d, 1H, J = 10.0Hz) 6.23 (d, 1H, J = 10.0Hz) 5.97 ~ 8.00 (m, 3H) 8.23 (s, 2H) 8.50 (s, 1H) Production Example 3 1N sodium hydroxide aqueous solution 20ml methanol 20
ml was added, and to this, 3.56 g of the present compound (28) was added. After heating and stirring at 60 to 80 ° C. for 1 hour, most of methanol was distilled off under reduced pressure, water was poured, and the mixture was made weakly acidic with concentrated hydrochloric acid. The precipitated solid was taken out by filtration with a glass filter, dried at 50 ° C. under reduced pressure, and 6-chloro-2,2-dimethyl-1- (4-carboxynicotinoyl) -1,2-dihydroquinoline (the present invention was used. 2.90 g of compound (30) was obtained. ¹ H-NMR (DMSO-d ₆ ) δ: 1.62 (s, 6H) 5.90 (d, 1H, J = 10.0Hz) 6.48 (d, 1H, J = 10.0Hz) 6.65 ~ 8.17 (m, 3H) 7.58 ( d, 1H, J = 5.0Hz) 8.20 (s, 1H) 8.63 (d, 1H, J = 5.0Hz) Production Example 4 6-chloro-2,2-dimethyl-1- (4-carboxynicotinoyl) -1 , 2 dihydroquinoline (the present compound (30)) (1.03 g) was dissolved in tetrahydrofuran (30 ml), and mesitylene sulfonyl chloride (0.98 g) was added to the solution.
0.73 g of 1-methylimidazole was added. 1 at room temperature
After stirring for 0 minutes, 0.22 g of monomethylamine hydrochloride and 0.34 g of triethylamine were added, and the mixture was stirred at room temperature for 15 minutes. The reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The obtained residue was subjected to thin layer chromatography (silica gel chloroform
/ Methanol 9: 1 (V / V)), 6-chloro-2,2-
Dimethyl-1- (4-N-methylcarbamoylnicotinoyl) -1,2-dihydroquinoline (the compound of the present invention (7
2)) 0.80 g was obtained. ¹ H-NMR (CDCl ₃ ) δ: 1.66 (s, 6H) 3.05 (d, 3H, J = 4.89Hz) 5.86 (d, 1H, J = 9.68Hz) 6.36 (d, 1H, J = 9.68Hz) 6.50 (br.d, 1H, J = 4.89Hz) 6.75 (dd 1H, J ₁ = 8.57Hz, J ₂ = 2.45Hz) 6.98 (d, 1H, J = 2.45Hz) 7.09 (d, 1H, J = 8.57Hz ) 7.33 (d, 1H, J = 4.96Hz) 8.30 (s, 1H) 8.56 (d, 1H, J = 4.96Hz) Next, the compound of the present invention which can be produced according to the above Production Example 1.2 and its physical properties Are shown in Table 1-24. In the table,
A compound in which R ⁶ is a COOH group is prepared in Production Example 3, R ⁶ is
Alternatively, the compound represented by Chemical formula 6 can also be produced according to Production Example 4.

[0019]

[Table 1]

[Table 2]

[Table 3]

[Table 4]

[Table 5]

[Table 6]

[Table 7]

[Table 8]

[Table 9]

[Table 10]

[Table 11]

[Table 12]

[Table 13]

[Table 14]

[Table 15]

[Table 16]

[Table 17]

[Table 18]

[Table 19]

[Table 20]

[Table 21]

[Table 22]

[Table 23]

[Table 24]

Next, formulation examples are shown. In addition, this invention compound is shown by the compound number of Table 1-21. Parts are parts by weight. Formulation Example 1 50 parts of each of the present compounds (1) to (117), 3 parts of calcium ligninsulfonate, 2 parts of sodium lauryl sulfate and 45 parts of synthetic hydrous silicon oxide are well pulverized and mixed to obtain each wettable powder. Formulation Example 2 10 parts of each of the compounds (1) to (117) of the present invention, 14 parts of polyoxyethylene styryl phenyl ether, 6 parts of calcium dodecylbenzene sulfonate, 35 parts of xylene and 35 parts of cyclohexanone were mixed well to prepare each emulsion. obtain. Formulation Example 3 Inventive compounds (1) to (117) 2 parts each, synthetic hydrous silicon oxide 2
Parts, 2 parts of calcium lignin sulfonate, 30 parts of bentonite and 64 parts of kaolin clay are well pulverized and mixed,
After adding water and kneading well, it is granulated and dried to obtain each granule. Formulation Example 4 Compounds of the present invention (1) to (4), (6), (8)-(13), (21), (22), (30)-
(33), (35)-(37), (38) (39), (41)-(49), (52)-(78), (80),
(82)-(86), (88), (90)-(91), (95)-(106), (111) (112), (1
17) 25 parts, polyvinyl alcohol 10% aqueous solution 50
And 25 parts of water are mixed, and wet pulverization is performed until the average particle size becomes 5 μm or less to obtain each suspension agent. Formulation Example 5 The present compound (5), (7), (14)-(20), (23)-(29), (34), (40), (50) in 40 parts of a 10% aqueous solution of polyvinyl alcohol. ,(Five
1), (79), (81), (87), (89), (92)-(94), (107)-(110), (113)
-(116) Add 5 parts each and use a homogenizer to get an average particle size of 1
It is emulsified and dispersed until it becomes 0 μm or less, and then 55 parts of water is added to each to obtain a thick emulsion. Next, Test Examples will show that the compound of the present invention is useful as an active ingredient of a herbicide. The compounds of the present invention are shown in Tables 1 to 21.
Comparative compounds shown in Table 25 were used as comparison targets.

[0021]

[Table 25] For the evaluation of herbicidal efficacy and phytotoxicity, the test plants (weeds and crops) at the time of the survey were evaluated as "0" when they had no or almost no emergence and growth condition compared to those of the untreated plants. A plant whose plant is completely dead or whose budding or growth is completely suppressed is defined as "10", and 0 to 10
It is divided into 11 stages of 0, 1, 2, 3, 4, 5, 6, 7,
Shown as 8, 9, and 10.

Test Example 1 Field soil treatment test Field soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and barnyard grass was sown to cover the soil. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount thereof was diluted with water equivalent to 1000 liters per hectare, and the whole soil surface was uniformly treated with an automatic sprayer. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Tables 26-27.

[Table 26]

[Table 27] Test Example 2 Field soil treatment test Field soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and American morning glory was sown. The test compound was made into an emulsion according to Formulation Example 2, a predetermined amount thereof was diluted with water equivalent to 1000 liters per hectare, and the whole soil surface was uniformly treated with an automatic sprayer. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Table 28.

[Table 28] Test Example 3 Field foliage treatment test Field soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and barnyard grass was sown and grown in a greenhouse for 7 days. Then, the test compound was made into an emulsion according to Formulation Example 2, a predetermined amount thereof was diluted with water containing 1000 liters of spreading agent per hectare, and foliage treatment was performed from above the plant with an automatic sprayer. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Table 29.

[Table 29] Test Example 4 Field foliage treatment test Field soil was filled in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and barley grass, morning glory and velvetleaf were sown and grown in a greenhouse for 7 days. Then, Formulation Example 2
The test compound was made into an emulsion in accordance with the procedure of 1. and a predetermined amount thereof was diluted with water containing 1000 liters of spreading agent per hectare, and foliage treatment was performed from above the plant with an automatic sprayer. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Tables 30-31.

[Table 30]

[Table 31] Test Example 5 Field foliage treatment test Field soil was packed in a cylindrical plastic pot having a diameter of 10 cm and a depth of 10 cm, and American morning glory was sown and grown in a greenhouse for 7 days. Thereafter, the test compound was made into an emulsion according to Formulation Example 2, and the predetermined amount thereof was adjusted to 1000 per hectare.
Diluted with water containing a spreading agent equivalent to 1 liter, and foliage-treated from above the plant with an automatic sprayer. After the treatment, the plants were grown in a greenhouse for 19 days, and the herbicidal efficacy was investigated. The results are shown in Table 32-3.
3 shows.

[Table 32]

[Table 33] Test Example 6 Paddy Submerged Water Treatment Test Soil was filled in a cylindrical plastic pot having a diameter of 8 cm and a depth of 12 cm, and seeds of the rice barley were sown. After flooding to make paddy fields, rice at the two-leaf stage was transplanted and grown in a greenhouse. After 5 days, emulsify the test compound according to Formulation Example 2,
The predetermined amount was diluted with water and treated on the water surface. After processing 19
The plants were cultivated in a greenhouse for one day, and their herbicidal efficacy and efficacy were investigated. The results are shown in Tables 34-35.

[Table 34]

[Table 35] Test Example 7 Upland soil treatment test Field up soil was packed in a vat having an area of 33 × 23 cm ² and a depth of 11 cm, and soybean, cotton, corn, Ainoenochogusa, Ambergrass, and Seibanmokoshi were sown, and 1-2 cm
It was covered with soil. According to Formulation Example 2, the test compound was made into an emulsion, and a predetermined amount thereof was diluted with water equivalent to 1000 liters per hectare, and the soil was treated with a sprayer. After treatment,
The plants were grown in a greenhouse for 18 days and examined for herbicidal efficacy. The results are shown in Table 36.

[Table 36] Test Example 8 Upland soil treatment test Soil was filled in a plastic pot having an area of 25 × 18 cm ² and a depth of 7 cm, and corn, Achinochonoecogosa, Inubiae, and Seiban Sorghum were sown, and soil was covered to a thickness of 1 to 2 cm. Emulsify the test compound according to Formulation Example 2,
The predetermined amount was diluted with water equivalent to 1000 liters per hectare and treated with a sprayer. After the treatment, the plants were grown in a greenhouse for 18 days, and herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 37.

[Table 37] Test Example 9 Upland Field Stem Treatment Test A bat having an area of 33 × 23 cm ² and a depth of 11 cm was filled with upland field soil, and corn, morning glory, velvetleaf,
Dog physalis was sown and cultivated for 16 days. Then, according to Formulation Example 2, the test compound was made into an emulsion, and a predetermined amount thereof was diluted with 1000 liters of water equivalent to 1 hectare containing the spreading agent, and sprayed from above the plant body to the entire leaf portion. Treated uniformly. At this time, the growth status of weeds and crops varies depending on the grass species, but at the 1 to 4 leaf stage, the plant height is 2 to 12c.
It was m. The phytotoxicity and herbicidal efficacy were investigated 18 days after the treatment. The results are shown in Table 38. The test was conducted in a greenhouse throughout the entire period.

[Table 38] Example 10 Paddy Submerged Water Treatment Test Soil was packed in a Wagner pot of 1/5000 are and seeded with sardines, eels, and stilts. After flooding to make it into a paddy field, 2-leaf stage rice was transplanted and grown in a greenhouse. After 5 days (the germination stage of Laminariae), the compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the compound was diluted with water and treated on the water surface. After the treatment, the plants were grown in a greenhouse for 20 days, and herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 39-42.
Shown in. In addition, in this test, it is 1 for 2 days from the day after the treatment.
A leak operation was performed in an amount corresponding to a water depth of 3 cm per day.

[Table 39]

[Table 40]

[Table 41]

[Table 42] Example 11 Paddy Submerged Water Treatment Test Soil was filled in a Wagner pot of 1/5000 are, and seeds of rice barley, eel, and short-spotted pearl millet were sown. After flooding to make it into a paddy field, 2-leaf stage rice was transplanted and grown in a greenhouse. After 12 days (Tainubie 1.5-2 leaf stage), the compound was made into an emulsion according to Formulation Example 2, and a predetermined amount of the compound was diluted with water and treated on the water surface. After the treatment, the plants were grown in a greenhouse for 20 days, and herbicidal efficacy and phytotoxicity were investigated. The results are shown in Table 43.
-44. In addition, in this test, the water leak operation was performed for the amount of 3 cm per day for 2 days from the day after the treatment.

[Table 43]

[Table 44]

 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Inventor Kazuo Saito 4-2-1 Takashi, Takarazuka-shi, Hyogo Sumitomo Kagaku Kogyo Co., Ltd. (72) Hiroyuki Kogai 4-2-1 Takashi, Takarazuka-shi, Hyogo No. Sumitomo Chemical Industry Co., Ltd.

Claims (2)

[Claims] 1. A general formula: ## STR1 ## [In the formula, R ¹ , R ² and R ³ are the same or different and each represents a hydrogen atom, a C1-C6 alkyl group, a halogen atom,
C1-C6 alkoxy group, halo C1-C6 alkyl group,
Halo C1-C6 alkoxy group, (C1-C6 alkoxy) carbonyl group, C1-C6 alkylthio group, C1-
C6 alkylamino group, di (C1-C6 alkyl) amino group, phenyl group or phenoxy group, wherein R ⁴ and R ⁵ are the same or different and each represents a hydrogen atom or C1-
Represents a C6 alkyl group or represents a C2-C5 alkylene group in which R ⁴ and R ⁵ are bonded at the terminal, and R ⁶ represents a hydrogen atom, a halogen atom, an amino group, a C1-C6 alkylamino group,
Di (C1-C6 alkyl) amino group, (C1-C6 alkoxy) carbonyl amino group, or a cyano group, or the formula of 2 ## STR2 ## -C (= O) -Y-R 7 (Y is oxygen Represents an atom or a sulfur atom, R ⁷ is a hydrogen atom, a C1-C10 alkyl group, a C2-C10 alkenyl group, a C2-C10 alkynyl group, a haloC1-C10 alkyl group, a haloC2-C10 alkenyl group, a haloC2-C.
10 alkynyl group, C3-C10 cycloalkyl group, C
3-C10 cycloalkenyl group, C1-C10 alkoxy C1-C10 alkyl group, C1-C10 alkylamino C1-C10 alkyl group, di (C1-C10 alkyl) amino C1-C10 alkyl group, furyl C1-C1
0 alkyl group, thienyl C1-C10 alkyl group, C1
Represents a C10 alkylamino group, a di (C1-C10 alkyl) amino group, or represents a (C1-C6 alkoxy) carbonyl group, a halogen atom or a phenyl group which may be substituted with a C1-C6 alkyl group. Or a (C1-C6 alkoxy) carbonyl group,
Represents a phenyl C1-C6 alkyl group which may be substituted with a halogen atom or a C1-C6 alkyl group,
Alternatively, it represents a group represented by -N = CHR or -N = CRR '. (Wherein R and R ′ are the same or different and each represents a C1-C10 alkyl group) or are represented by the general formula: (R ⁸ and R ⁹ are the same or different and are a hydrogen atom, C1-
C6 alkyl group, C2-C6 alkenyl group, C2-C6
Alkynyl group, halo C1-C6 alkyl group, halo C2-
C6 alkenyl group, halo C2-C6 alkynyl group, C3
-C6 cycloalkyl group, C3-C6 cycloalkenyl group, amino group, C1-C6 alkylamino group or di (C1-C6 alkyl) amino group, or substituted with a halogen atom or a C1-C6 alkyl group Or a phenyl C1-C6 alkyl group which may be substituted with a halogen atom or a C1-C6 alkyl group. ), X represents CH or N. ] N-
Acyl dihydroquinoline derivatives. 2. A herbicide containing the N-acyl dihydroquinoline derivative according to claim 1 as an active ingredient.