KR20040007541A - Substituted benzoylcyclohexenones and their use as herbicidal agents - Google Patents

Abstract

The present invention relates to novel substituted benzoylcyclohexens of formula (I), methods for their preparation and their use:

Where

Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y and Z have one of the meanings given in the specification.

Description

Substituted benzoylcyclohexenones and their use as herbicidal agents}

Part of substituted benzoylcyclohexenone or benzoylcyclohexanedione, such as compound N- [2,6-dichloro-3-[(3,3-dimethyl-2,6-dioxo-cyclohexyl) -carbonyl] -Phenyl] -acetamide, N- [2-chloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -4-nitro-phenyl] -acetamide, N- [2-chloro- 3-[(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide, N- [2,6-dichloro-3-[(2,6-dioxo-cyclohexyl) -carbo Neyl] -phenyl] -acetamide (see US-A-4 780 127) is already known to have herbicidal properties (see EP-A-090 262, EP-A-135 191, EP-A-137). 963, EP-A-186 118, EP-A-186 119, EP-A-186 120, EP-A 319 075, WO-A-96 / 26200, WO-A-97 / 46530, WO-A-99 / 07688, WO-A-99 / 10327, WO-A-00 / 05221, WO-A-00 / 21924. However, the activity of these compounds is not entirely satisfactory.

The present invention relates to novel substituted benzoylcyclohexenes, their preparation and their use as herbicides.

The present invention provides novel substituted benzoylcyclohexens of formula (I), including all possible tautomeric forms of compounds of formula (I) and possible salts of compounds of formula (I):

Where

Q represents O (oxygen) or S (sulfur),

R ¹ represents hydrogen, halogen or in each case optionally substituted alkyl, alkylthio or aryl,

R ² represents hydrogen, halogen or optionally substituted alkyl, or together with R ¹ represents O (oxygen) or alkanediyl (alkylene),

R ³ is hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, Dialkylaminocarbonyl or dialkylaminosulfonyl;

R ⁴ is hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl, alkylamino, dialkylamino, Dialkylaminocarbonyl or dialkylaminosulfonyl,

R ⁵ is hydrogen or in each occurrence optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylthio, arylsulfinyl, arylsul Phonyl, arylalkyl, or the group -C (Q) -Z,

Y is hydroxyl, halogen or in each case optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy , Alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl Indicates

Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino, Alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydrazino, alkylsulfonylhydrazino, dialkylamino, N-alkyl-alkoxyamino, dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino, al Kenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, Aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyl, he Rosa shows a cycle-yloxy, heterocyclyl thio, heterocyclyl amino, a group -N = (heterocyclyl), heterocyclyl-alkyl, heterocyclyl alkyl, heteroaryl recital days alkylthio or heterocyclyl-alkyl-amino,

Wherein the radicals R ³ and R ⁴ are each preferably located at positions (2) and (4) of the phenyl ring,

The abovementioned compound N- [2,6-dichloro-3-[(3,3-dimethyl-2,6-dioxo-cyclohexyl) known from the patent document (see US-A-4 780 127) -Carbonyl] -phenyl] -acetamide, N- [2-chloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -4-nitro-phenyl] -acetamide, N- [ 2-Chloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide, and N- [2,6-dichloro-3-[(2,6-dioxo- Cyclohexyl) -carbonyl] -phenyl] -acetamide is excluded.

Preferred substituents or groups in the formulas mentioned above and below are illustrated below:

Q preferably represents O.

R ¹ preferably represents hydrogen, halogen, or optionally halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, or phenyl.

R ² preferably represents hydrogen, halogen, optionally halogen-substituted alkyl of 1 to 6 carbon atoms, or O (oxygen) or alkanediyl of 2 to 5 carbon atoms with R ¹ (Alkylene).

R ³ , R ⁴ preferably represent, independently of one another, hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each case up to 4 carbon atoms in the alkyl group, optionally in each case -, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio , Alkylsulfinyl or alkylsulfonyl, or in each case alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl having up to 4 carbon atoms in the alkyl group.

R ⁵ preferably represents hydrogen or in each case has 1 to 6 carbon atoms in the alkyl group and in each case is optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl, alkoxy, alkylthio , Alkylsulfinyl, alkylsulfonyl, or in each case an alkenyl or alkynyl group having 3 to 6 carbon atoms and in each case optionally cyano- or halogen-substituted alkenyl or alkynyl, or In this case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted cycloalkyl or cycloalkyl Alkyl, or in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally nitro-, cyano-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ - halogeno noal -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - halogenoalkyl alkoxy -, C ₁ -C ₄ - alkylthio -, C ₁ -C ₄ - halogenoalkyl thio -, C ₁ -C ₄ - Alkylsulfinyl-, C ₁ -C ₄ -halogenoalkylsulfinyl-, C ₁ -C ₄ -alkylsulfonyl- or C ₁ -C ₄ -halogenoalkylsulfonyl-substituted aryl, arylthio, arylsulphi Nil, arylsulfonyl or arylalkyl, or the group -C (Q) -Z.

Y preferably represents hydroxyl, halogen or in each case an alkyl group has 1 to 6 carbon atoms and in each case is optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkoxy, alkylthio , Alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, in each case 3 to 6 carbon atoms and in each case optionally cyano- or Halogen-substituted alkenyloxy or alkynyloxy, or in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, optionally in each case nitro-, cyano-, C ₁ -C ₄ - alkyl -, C ₁ -C ₄ - halogenoalkyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - halogenoalkyl alkoxy -, C ₁ -C ₄ - alkylthio -, C ₁ -C ₄ -halogenoalkylthio-, C ₁ -C ₄ -alkylsulfinyl-, C ₁ -C ₄ -halogenoalkylsulfinyl-, C ₁ -C ₄ -alkylsulfonyl- or C ₁ -C ₄ -halogenoalkylsulfonyl-substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, Arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl.

Z preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, C ₁ -C ₄ -alkyl-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl, or

In each case optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl Substituted, alkyl having at least two carbon atoms, in each case 1 to 6 carbon atoms in the alkyl group, alkoxy, alkylthio, alkylamino, alkoxyamino, alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydra Zino or alkylsulfonylhydrazino, or

In each case a dialkylamino, N-alkyl-alkoxyamino or dialkylhydrazino having 1 to 4 carbon atoms in the alkyl group, or in each case 2 to 6 carbon atoms and optionally halogen-substituted Kenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino, or

In each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted cycloalkyl, cyclo Alkyloxy, cycloalkylamino, cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino, or

In each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally nitro-, cyano, halogen, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -Halogenoalkyl-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -halogenoalkoxy- or C ₁ -C ₄ -alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy, aryloxy Carbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino, or

Optionally nitro in each case, cyano-, halogen -, C ₁ -C ₄ - alkyl -, C ₁ -C ₄ - halogenoalkyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - haloalkyl Genoalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -halogenoalkylthio- or C ₁ -C ₄ -alkoxy-carbonyl- or C ₃ -C ₆ -cycloalkyl-substituted mono Cyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, group -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio Or heterocyclylalkylamino, where in each case the heterocyclyl group has up to 10 carbon atoms and additionally nitrogen (but at most 5 N atoms), oxygen (but at most 2 O atoms), sulfur (but at most two S atoms), at least one heteroatom and optionally selected from the group consisting of SO or SO ₂ Cattle (C = O), thioxo (C = S), imino (C = NH), cyano noi mino one selected from a (C = N-CN) and niteuroyi diamino (C = N-NO ₂₎ group consisting of It further contains a group of and if appropriate the alkyl moiety contains 1 to 4 carbon atoms.

R ¹ particularly preferably represents hydrogen, fluorine, chlorine or bromine, or in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethyl Thio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, or phenyl.

R ² particularly preferably represents hydrogen, fluorine, chlorine or bromine or in each case is optionally fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl or O (oxygen), ethane-1,2-diyl, propane-1,3-diyl or butane-1,4-diyl together with R ¹ .

R ³ , R ⁴ particularly preferably independently of one another represent hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or in each case optionally fluorine-, chlorine- , Methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i -Propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsul Phenyl or methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl Dimethylaminosulfonyl or Ethyl shows aminosulfonyl.

R ⁵ particularly preferably represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n- , i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- Or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or di Ethylamino, or in each case optionally fluorine-, chlorine- and / or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, or Optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or Ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine -Bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl Or group -C (Q) -Z.

Y particularly preferably represents hydroxyl, formyloxy, fluorine, chlorine or bromine, or in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-pro Foxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyl jade Methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsul Propenyl jade which represents or is fluorine-, chlorine- and / or bromine-substituted or optionally in each case phonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy , Butenyloxy, propynyloxy or butynyloxy, or in each case optionally nitro-, cyano-, fluorine-, chlorine, bromine-, methyl-, ethyl-, n- or i-propyl- , n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, Methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulfinyl-, ethylsulfinyl-, trifluoromethylsulfinyl-, methyl Sulfonyl-, ethylsulfonyl- or trifluoromethylsulfonyl-substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy , Phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.

Z particularly preferably represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino,

Cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, or Ethylsulfonyl-substituted methyl, or

In each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphi Nyl-, ethylsulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl-, or ethylsulfonyl-substituted ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n Or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methy Methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethyl hydrazino, n- or i-propylhydrazino, n- , i-, s- or t-butylhydrazino,

Dimethylamino, diethylamino, N-methyl-methoxyamino or dimethylhydrazino, or

In each case optionally fluorine-, chlorine- and / or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentene Iloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethynyl, propynyl, butynyl Or pentynyl, propynyloxy, butynyloxy, pentynyloxy, propynylamino, butynylamino or pentynylamino,

In each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohex Siloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl Or cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino

In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i- Propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenyl Ethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, petylethylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy, naphthylmethylamino or naphthyl Ethylamino, or

Furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, Dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino, thienylmethyl, tenylmethylamino, dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy, dithiolyl Olanylmethylamino, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrroylylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, already Dazolinyl, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylamino, dihydrooxazolyl (oxazolinyl ), Tetrahydrojade Zolyl (oxazolidinyl), isoxazolyl, isoxazolylamino, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), tetrahydro- (2H) -1,2 -Oxazin-2-yl, oxazolylmethyl, thiazolyl, thiazolylamino, thiazolylmethyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), thiazolinylthio, thiazolin Monoamino, oxothiazolidinyl, cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino, triazolylamino, oxotriazolinyl, thioxotriazolinyl, oxotetrazolinyl, oxoterazolinyl Methyl, tetrazolylmethyl, dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, dithiayl, dithiaylmethyl, dithiaylmethoxy, dithiaylmethylamino, piperidinyl, piperidinyl Amino, oxopiperidinyl, 2-oxo-1,3-diaza-cycle Lohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinyl Thio, pyridinylamino, 2- (1H) -pyridinimino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylthio, pyrimidinylamino, pyrimidinylmethyl or pyrimidine Optionally in each case nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t -Butyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i -Propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n -, i-, s- or t-butyl O-, difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocycles 1, heterocyclyloxy, heterocyclylamino, group -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino.

R ¹ very particularly preferably represents hydrogen or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio Or phenyl.

R ² very particularly preferably represents hydrogen or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, or optionally together with R ¹ ethane-1,2-diyl , Propane-1,3-diyl or butane-1,4-diyl.

R ³ , R ⁴ are very particularly preferably independently of one another hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, Dichloromethyl, trichloromethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl , Ethylsulfinyl, methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl.

R ⁵ very particularly preferably represents hydrogen, or in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n- or represent i-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfy Phenyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, or in each case optionally fluorine- and / or chlor-substituted propenyl, butenyl, pro Pinyl or butynyl, or in each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or Represents cyclohexylmethyl, or in each case Ronitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl- , Methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl Or group -C (Q) -Z.

Y very particularly preferably represents hydroxyl or in each case is optionally fluorine- and / or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n Or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsul Phonyloxy, or

In each case optionally represents fluorine-, chlorine-, and / or bromine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy,

In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, Difluoromethylthio-, trifluoromethylthio-, methylsulfinyl-, ethylsulfinyl-, trifluoromethylsulfinyl-, methylsulfonyl-, ethylsulfonyl- or trifluoromethylsulfonyl-substituted Phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl.

Z very particularly preferably represents amino, cyanoamino, hydrazino, or

Cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethyl Sulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl-, or ethylsulfonyl-substituted methyl,

In each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphi Nyl-, ethylsulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxyamino , n- or i-propoxyamino, methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, or dimethylamine, N- Methylmethoxyamino or dimethylhydrazino, or

In each case optionally fluorine- and / or chlor-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenyl Amino, butenylamino, propenyloxyamino, butenyloxyamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, or

In each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino , Cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Pentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or

In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i- Propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenyl Ethylthio, phenylmethylamino or phenylethylamino, or

Furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, Dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylmethyl, dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl , Pyrrolidinylamino, oxopyrrolidinyl, pyrroylyl, indolyl, pyrrolyylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl, imidazolylmethyl , Imidazolinylmethyl, oxoimidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxa Zolidinyl), isoxazolyl, Dihydroisoxazolyl (isoxazolinyl), tetrahydro- (2H) -1,2-oxazin-2-yl, tetrahydroisoxazolyl (isoxazolidinyl), thiazolyl, thiazolylmethyl, di Hydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), thiazolimino, oxothiazolidinyl, cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino, oxotriazolyl , Oxotetrazolylmethyl, terrazolylmethyl, oxotetrazolinyl, oxotetrazolylmethyl, tetrazolylmethyl, dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, ditianyl, Ditianylmethyl, ditianylmethoxy, ditianylmethylamino, triazolylamino, piperidinyl, piperidinylamino, 2- (1H) -pyridinimino, oxopiperidinyl, 2-oxo-1,3- Diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, Morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy In the group consisting of, in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t- Butyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i- Propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methoxycarbo Nyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy , Heterocyclylamino, group -N = (heterocycleyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino.

R ¹ and R ² most preferably represent hydrogen.

R ³ most preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl.

R ⁴ most preferably represents hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl.

R ⁵ most preferably represents hydrogen.

Y most preferably represents hydroxyl.

Preference is given to compounds of the formula (I) which comprise a combination of the meanings listed above as being preferred according to the invention.

Particular preference is given to compounds of the formula (I) which comprise a combination of the meanings listed above as being particularly preferred according to the invention.

Very particular preference is given to compounds of the formula (I) which comprise combinations of the meanings listed above as very particularly preferred according to the invention.

Most preferred are compounds of formula (I) which comprise a combination of the meanings listed above as most preferred according to the invention.

Wherein the above-mentioned compound N- [2,6-dichloro-3-[(3,3-dimethyl-2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] known in the patent literature -Acetamide, N- [2-chloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -4-nitro-phenyl] -acetamide, N- [2-chloro-3- [ (2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide and N- [2,6-dichloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl]- Phenyl] -acetamide (see US-A-4780127) is excluded.

Very particularly preferred group

Q represents O or S,

R ¹ represents hydrogen or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or phenyl Indicates,

R ² represents hydrogen, or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, or optionally together with R ^{1 is} ethane-1,2-diyl, propane-1, 3-diyl or butane-1,4-diyl,

R ³ , R ⁴ are independently of each other hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloro Methyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, Methylsulfonyl, ethylsulfonyl or dimethylaminosulfonyl,

R ⁵ represents hydrogen or in each case optionally represents cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl Or methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , Ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, or in each case optionally fluorine- and / or chlor-substituted propenyl, butenyl, propynyl or butynyl Or in each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl Or optionally in each case nitro-, cyano-, fire -Chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl, or group -C (Q) -Z,

Y represents hydroxyl or, in each case, optionally fluorine- and / or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl Sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-pro Foxoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy ,

In each case optionally represents fluorine-, chlorine-, and / or bromine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy,

In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, Difluoromethylthio-, trifluoromethylthio-, methylsulfinyl-, ethylsulfinyl-, trifluoromethylsulfinyl-, methylsulfonyl-, ethylsulfonyl- or trifluoromethylsulfonyl-substituted Phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl,

Z represents amino, cyanoamino, hydrazino, or

Cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethyl Sulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl-, or ethylsulfonyl-substituted methyl,

In each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylsulfinyl-, methyl Sulfonyl- or ethylsulfonyl-substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl Thio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, methylhydrazino, ethylhydrazino, n Or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, dimethylamine, N-methylmethoxyamino or dimethylhydrazino,

In each case optionally fluorine- and / or chlor-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenyl Amino, butenylamino, propenyloxyamino, butenyloxyamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, or

In each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino , Cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Pentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or

In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i- Propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenyl Ethylthio, phenylmethylamino or phenylethylamino, or

Furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, Dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylmethyl, dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl , Pyrrolidinylamino, oxopyrrolidinyl, pyrroylyl, indolyl, pyrrolyylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl, imidazolylmethyl , Imidazolinylmethyl, oxoimidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, oxotetrazolinylmethyl, terrazolylmethyl, dihydrooxazolyl ( Oxazolinyl), tetrahi Rooxazolyl (oxazolidinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), thiazolyl, thiazolylmethyl, dihydrothiazolyl (thia Zolinyl), tetrahydrothiazolyl (thiazolidinyl), oxothiazolidinyl, cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl, dioxanyl, dioxanylmethyl, dioxanylmethoxy, Dioxanylmethylamino, dithiayl, dithiaylmethyl, dithiaylmethoxy, dithiaylmethylamino, piperidinyl, piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl , 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, Pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyri Among the groups consisting of dinylmethoxy, in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- Or t-butyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- Or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, Methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino, group -N = ( Heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino.

Particular emphasis is given to compounds of the formulas (I-1) to (I-3):

here,

Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y and Z each have the meanings listed above as very particularly preferred.

Again, the radicals R ³ and R ⁴ are preferably located at positions (2) and (4) of the phenyl ring, respectively.

The general or preferred radical definitions mentioned above apply to both the final product of the formula (I) and correspondingly the starting material or in each case the intermediates required for preparation. These radical definitions may be combined with one another, if necessary, including combinations between the preferred ranges provided.

Unless otherwise specified, the following definitions apply to the definitions given above and below:

Saturated or unsaturated hydrocarbon chains such as alkyl, alkanediyl, alkenyl or alkynyl, also in combination with heteroatoms such as alkoxyl, alkylthio or alkylamino are in each case straight or branched chain. Unless otherwise specified, hydrocarbon chains having 1 to 6 carbon atoms are preferred.

Aryl is an aromatic mono- or polycyclic hydrocarbon ring, such as phenyl, naphthyl, anthranyl, phenanthryl, preferably phenyl or naphthyl, especially phenyl.

Heterocycleyl refers to a saturated, unsaturated or aromatic cyclic compound wherein at least one ring member is a heteroatom, ie an atom other than carbon. If the ring contains a plurality of heteroatoms, they may be the same or different. Preferred heteroatoms are oxygen, nitrogen or sulfur. If the ring contains a plurality of oxygen atoms, they are not adjacent. If appropriate, the cyclic compound forms a polycyclic ring system with additional fused or bridged carbocyclic or heterocyclic rings. Polycyclic ring systems can be bonded by heterocyclic rings or fused carbocyclic rings. Mono- or bicyclic ring systems are preferred, with monocyclic ring systems having 5 or 6 ring members and bicyclic ring systems having 7 to 9 ring stops being particularly preferred.

Cycloalkyl refers to a saturated carbocyclic compound capable of optionally forming a polycyclic ring system with other carbocyclic rings fused or bridged. Unless otherwise specified, cyclopropyl, cyclopentyl and cyclohexyl are preferred.

Newly substituted benzoylcyclohexens of formula (I) have strong and selective herbicidal activity.

Newly substituted benzoylcyclohexenes of formula (I) are suitable for cyclohexanedione of formula (II) (“hydroxycyclohexenone”) in the presence of a dehydrating agent, if appropriate, in the presence of one or more reaction aids, and if appropriate Reacting with a substituted benzoic acid of formula (III) or a reactive derivative thereof, such as a corresponding acid halide, acid anhydride, acid cyanide or ester, in the presence of at least one diluent,

If appropriate, the resulting compound of formula (I) is then subjected to an electrophilic or nucleophilic substitution and / or oxidation or reduction reaction in the usual manner within the definition of the substituent, or to the compound of formula (I) Obtained by the conversion into salts in the manner of:

Where

R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Q and Z have the meanings given above.

In principle, the novel substituted benzoylcyclohexens of formula (I) can also be obtained as shown in the following scheme:

Reaction of the halogeno (thio) carbonyl compound of formula (V) or the corresponding iso (thio) cyanate, if appropriate, with the aminobenzoylcyclohexenone of formula (IV), wherein Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y and Z have the meanings given above and X represents halogen):

Formulas (IV) and (V) provide general definitions of the compounds to be used as starting materials in the processes (α) and (β) according to the invention. In formulas (IV) and (V), Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y and Z are preferably in connection with the detailed description of the compounds of formula (I) according to the invention It has the meaning already mentioned above as preferred, particularly preferred, very particularly preferred or most preferred for, Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Y and Z.

Starting materials of formula (V) are compounds known to those skilled in the art.

Starting materials of formula (IV) may be obtained in a manner known to those skilled in the art.

Reaction of the nucleophilic compound of formula (VII) with iso (thio) cyanatobenzoylcyclohexenone of formula (VI), wherein Q, R ¹ , R ² , R ³ , R ⁴ , Y and Z are Has the meaning given):

For example, using cyclohexane-1,3-dione and 2-chloro-4-[(dimethylaminocarbonyl)-(methylamino)]-benzoic acid as starting materials, the reaction route in the process according to the invention For example, the following scheme is shown:

Formula (II) provides a general definition of cyclohexanedione to be used as starting material in the process according to the invention for preparing compounds of formula (I). In formula (II), R ¹ and R ² are preferably preferred, particularly preferred, very particularly preferred, for R ¹ and R ² with respect to the detailed description of the compounds of formula (I) according to the invention Or most preferred as already mentioned above.

Starting materials of formula (II) are known and / or may be prepared by methods known per se.

Formula (III) provides a general definition of substituted benzoic acid to be used further as starting material in the process according to the invention. In formula (III), Q, R ³ , R ⁴ , R ⁵ and Z are preferably Q, R ³ , R ⁴ , R ⁵ and in connection with the detailed description of the compounds of formula (I) according to the invention It has the meanings already mentioned above as preferred, particularly preferred, very particularly preferred or most preferred for Z.

Starting materials of formula (III) are known and / or can be prepared by methods known per se (see JP-A-11292849, Preparation).

Substituted benzoic acid of formula (III) may be prepared by reacting the benzoic acid ester of formula (IIIa) in the presence of a hydrolysis aid, such as aqueous sodium hydroxide solution, if appropriate in the presence of a diluent, such as tetrahydrofuran, from 0 ° C to 100 ° C. Obtained by reaction with water at a temperature of (see Preparation Example):

Where

Q, R ³ , R ⁴ , R ⁵ and Z have the meanings given above,

R represents alkyl, in particular methyl or ethyl.

The benzoic acid esters of formula (IIIa) required as precursors are known and / or can be prepared by methods known per se (see JP-A-11292849, Preparation).

The benzoic acid ester of formula (IIIa)

(α) from 0 ° C. to 100 in the presence of an acid acceptor, such as potassium carbonate or triethylamine, if appropriate, in the presence of a diluent, such as methyl isobutyl ketone or acetonitrile, if appropriate Reacting with a halogeno (thio) carbonyl compound of formula (VI) or, if appropriate, the corresponding iso (thio) cyanate at a temperature of < RTI ID = 0.0 >

(β) the iso (thio) cyanatobenzoic acid ester of formula (X) is suitably in the presence of a reaction aid, such as triethylamine, if appropriate in the presence of a diluent, such as acetonitrile or toluene, from 10 ° C. to 120 Obtained by reaction with a nucleophilic compound of formula (VIII) at a temperature of < RTI ID = 0.0 >

Where

Q, R ³ , R ⁴ , R ⁵ and Z have the meanings given above,

R represents alkyl, in particular methyl or ethyl,

X represents halogen, in particular fluorine, chlorine or bromine.

Formulas (IX), (VI), (X) and (VIII) provide general definitions of the compounds to be used as starting materials in the methods (α) and (β) according to the invention. In formulas (IX), (VI), (X) and (VIII), Q, R ³ , R ⁴ , R ⁵ and Z are preferably in connection with the detailed description of the compounds of formula (I) according to the invention It has the meaning already mentioned above as preferred, particularly preferred, very particularly preferred or most preferred for, Q, R ³ , R ⁴ , R ⁵ and Z.

Starting materials of formula (VI) and (VIII) are compounds known to those skilled in the art.

Starting materials of formulas (IX) and (X) can be obtained in a manner known to those skilled in the art.

The process according to the invention for preparing the new substituted benzoylcyclohexenone of formula (I) is preferably carried out using a dehydrating agent. Here, suitable dehydrating agents are usually suitable chemical agents for binding water.

One example that may be mentioned is dicyclohexylcarbodiimide, propanephosphonic anhydride and carbonyl-bis-imidazole.

Dehydrating agents which may be mentioned as being particularly suitable are dicyclohexylcarbodiimide and propanephosphonic anhydride.

The process for the preparation of the novel substituted benzoylcyclohexenes of formula (I) according to the invention is carried out using reaction aids as appropriate.

Examples of reaction aids that may be mentioned are sodium cyanide, potassium cyanide, acetone cyanohydrin, 2-cyano-2- (trimethylsilyloxy) -propane and trimethylsilyl cyanide.

It may be mentioned that trimethylsilyl cyanide is a particularly suitable reaction aid.

The process according to the invention is preferably carried out using one or more reaction aids. Reaction aids suitable for the process according to the invention are generally customary inorganic or organic base or acid acceptors. They are preferably alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkoxides, such as sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, potassium amide or calcium amide , Sodium carbonate, potassium carbonate or calcium carbonate, sodium, bicarbonate, potassium bicarbonate or calcium bicarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, sodium hydroxide, potassium Hydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- or i-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide, n- or i -Propoxide, n-, i-, s- or t-butoxide; Basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexyl-amine, dicyclohexylamine, ethyl-dicyclohexyl Amine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl Piperidine, N-methyl-morpholine, N-ethyl-morpholine, 1,4-diazabicyclo [2.2.2] -octane (DABCO), 1,5-diazabicyclo [4.3.0]- Non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] -undec-7-ene (DBU).

Further reaction aids suitable for the process according to the invention are phase transfer catalysts. Examples of the following catalysts may be mentioned as such catalysts:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogensulfate, methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, benzyl-trimethylammonium chloride, benzyl -Triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tri Butyl-hexadecylphosphonium bromide, butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide, tetraphenylphosphonium bromide.

The process for preparing the compound of formula (I) according to the invention is preferably carried out in each case with one or more diluents. Suitable diluents for carrying out the process according to the invention are especially inert organic solvents. These are in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, Diethylene glycol monoethyl ether.

When carrying out the process according to the invention, the reaction temperature can vary within a relatively wide range. In general, the process is carried out at temperatures of 0 ° C to 150 ° C, preferably 10 ° C to 120 ° C.

The process according to the invention is generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention at elevated or reduced pressures-generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials are generally used in approximately equal molar amounts. However, it is also possible to use one component in a relatively excess amount. The reaction is generally carried out in a suitable diluent in the presence of a reaction aid and the reaction mixture is generally stirred for several hours at the required temperature. Work-up is carried out in a conventional manner (see Preparation Example).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killer and especially weed killer. Weeds, in the broadest sense, mean all plants that grow in unwanted places. Whether the substance according to the invention acts as a total or selective herbicide depends essentially on the amount used. The active compounds according to the invention can be used, for example, in connection with the following plants:

To in the dicotyledonous weed Abu epothilone (Abutilon), probably Lantus (Amaranthus), Ambrosia (Ambrosia), Arnaud is (Anoda), Ante Miss (Anthemis), sick ness (Apanes), art Reflex (Atriplex), belriseu (Belis) , a non-dense (Bidens), capsule La (Capsella), carboxylic Douce (Carduus), cassia (Cassia), center urea (Centaurea), Ke-established rhodium (Chenopodium), unsealing syum (Cirsium), convolution bulruseu (Convolvulus), the Natura (Datura), des modyum (Desmodium), the Mex (Emex), Erie during drought (Erysimum), yuporeubiah (Euphorbia), Gale option system (Galeopsis), ground Soga (Galinsoga), gallium (Galium), Hi-bis Hibiscus , Ipomoea , Kochia , Lamium , Lepidium , Lindernia , Matricaria , Mentha , Mer Alice Kurihara (Mercurialis), and Mulu (Mullugo), Mio bovine teeth (Myosotis), Papa Bell (Papaver), Parque non-Tees (Pharbitis), flan And (Plantago), Polygonum (Polygonum), Fort Tula car (Portulaca), La nunkul Ruth (Ranunculus), Rafa Augustine (Raphanus), roripa (Rorippa), as Tala (Rotala), Lou Mex (Rumex), buy Lola ( Salsola ), Senecio , Sesbania , Sida , Sinapis , Solanum , Sonchus , Sphenoclea , Stellaria ), fall sakum (Taraxacum), teulra RY (Thlaspi), Tripoli Titanium (Trifolium), Ur urticae (Urtica), Veronica (Veronica), viola (viola) and greater santyum (Xanthium).

To the genus dicotyledonous crops: arachis (Arachis), beta (Beta), Brassica (Brassica), Cucumis (Cucumis), Cuckoo Le Vita (Cucurbita), tooth not patronize (Helianthus), Dow Syracuse (Daucus), Glee Cinemax (Glycine), announced europium (Gossypium), Ipoh Moe Oh (Ipomoea), Rock Dukas (Lactuca), rinum (Linum), Rico Percy cone (Lycopersicon), Nico tiahna (Nicotiana), Pace come loose (Phaseolus), pisum ( Pisum ), Solanum and Vicia ,

Monocotyledonous weeds in the To: Oh the way ropseu (Aegilops), Agrobacterium Piron (Agropyron), Agrobacterium seutiseu (Agrostis), Alor page kuruseu (Alopecurus), ahpera (Apera), ABE or (Avena), beuraki Aria (Brachiaria), Bro Moose (Bromus), Sen Cruz (Cenchrus), nose Melina (Commelina), Sino money (Cynodon), between Peru's (Cyperus), daktil lock'll help (Dactyloctenium), D. other Ria (Digitaria), Echinacea-no claws ah ( Echinochloa , Eleocharis , Eleusin , Eragrotis , Eriochloa , Festuca , Fimbristylis , Heteranthera , Imperata , Ischaemum , Leptochloa , Lolium , Monochoria , Panicum , Paspalum , Phalaris , Phleum , Poa , Rottboellia , Sagitta ria ), Scirpus , Setaria and Sorghum .

To the genus monocotyledonous crops: Allium (Allium), Ananas (Ananas), aspartate Goose (Asparagus), ABE or (Avena), Johor deum (Hordeum), duck party (Oryza), Trapani Qom (Panicum), Saccharomyces Room (Saccharum ), three-Calais (Secale), sorbitol gum (Sorghum), Tea tree Calais (Triticale), the tree tikum (Triticum) and Jea (Zea).

However, the use of the active compounds according to the invention is not limited at all in the above, but also extends to other plants in the same way.

The active compounds according to the invention are suitable for the overall control of weeds, depending on concentration, for example on industrial zones and railway lines, and on walkways and plazas, with or without trees. Similarly, the active compounds according to the invention are perennial crops such as plantations, ornamental water plantations, orchards, vineyards, citrus fields, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, palm plantations, cocoa plantations, It can be used to control weeds in soft fruit plantations and hop fields, grass, turf and pasture, and to selectively control weeds in annual crops.

The compounds of the formula (I) according to the invention show a strong herbicidal activity and a broad spectrum of activity when used on the ground of soils and plants. They are also suitable to some extent selectively control monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops by both pre- and post-germination methods.

At certain concentrations or rates of application, the active compounds according to the invention can also be used to control animal pests and fungal or bacterial plant diseases. In some cases, the active compounds according to the invention can also be used as intermediates or precursors for synthesizing other active compounds.

According to the invention, all plants and plant parts can be treated. Plant is to be understood here as meaning all plants and plant populations, such as desired or unwanted wild plants or crops (including naturally occurring crops). Crops include plant varieties and transgenic plants that may or may not be protected by the authority of a plant breeder, by conventional plant breeding and optimization methods, by biotechnology and recombinant methods, or by these methods. It may be a plant obtainable in combination. The plant part is to be understood as all the ground and underground parts and organs of the plant, for example, shoots, leaves, flowers and roots, for example leaves, needles, stalks, stems, flowers, Fruits, fruits, seeds, roots, tubers and rhizomes may be mentioned. Plant parts also include harvesting materials, and nutritional and reproductive materials such as seedlings, tubers, rhizomes, cuttings and seeds.

Treatment of plants and plant parts with the active compounds according to the invention is also carried out by conventional treatment methods, for example by dipping, spraying, evaporating, spraying, spraying, brushing, and in the case of propagating substances, in particular seeds. Or by acting directly or on its surroundings, environment or storage space by means of a multilayer coating.

The active compounds are usually used as solutions, emulsions, hydrating powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials in which the active compound is injected, and microcapsules in polymers. It can be converted into the formulation of.

These formulations are prepared by known methods, for example by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, optionally using surfactants, ie emulsifiers and / or dispersants and / or foam formers.

If the extender used is water, for example an organic solvent can also be used as cosolvent. Suitable liquid solvents are mainly aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils. Strong polar solvents such as aliphatic hydrocarbons, alcohols such as butanol or glycol and ethers and esters thereof, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, dimethylformamide and dimethyl sulfoxide .

Suitable solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly dispersed silica, alumina and silicates. Suitable granular solid carriers are, for example, pulverized and classified natural rocks such as calcite, marble, pumice, calcite and dolomite, and synthetic granules of inorganic and organic powders, and organic such as sawdust, coconut husk, corncobs and tobacco stems. Granules of matter. Suitable emulsifiers and / or foam formers are for example nonionic and anionic emulsifiers, for example polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates , Arylsulfonates and protein hydrolysates. Suitable dispersants are for example lignin-sulfite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latex, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, and synthetic phospholipids Can be used. Other additives may be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and prussian blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants and salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Micronutrients can be used.

The formulations generally contain 0.1 to 95% by weight, preferably 0.5 to 90% by weight of active compound.

In the control of weeds, the active compounds according to the invention are mixtures with substances ('safeners') which improve their compatibility with known herbicides and / or crops, on their own or in preparations. It can be used as a finished product formulation or tank mix is possible. Also possible is a mixture with a weed-killer comprising one or more known herbicides and safeners.

Possible components in the mixture are known herbicides such as acetochlor, acifluorfen (-sodium), acloniphene, alachlor, alkoxydim (-sodium), amethrin, amikabazone, amidochlor, amido Dosulfuron, anilophos, asulam, atrazine, azaphenidine, azimsulfuron, beflutamide, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), betazone, benzfendizone, Benzobicyclone, benzophenab, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromophenoxime, bromoxynil, butachlor, butafenacyl ( Allyl), butoxydim, butyrate, carfenstrol, caroxydim, carbetamid, carpentrazone (-ethyl), clomethoxyphene, chlorambene, chloridazone, chlorimuron (-ethyl) , Chlornitropen, chlorsulfuron, chlortoluron, cinidon (-ethyl), citmethyline, cynosulfuron, clepoxydim, cletodim, chlor Dinapov (-propargyl), clomazone, clomeprop, clopyralide, clopyrasulfuron (-methyl), cloransullam (-methyl), cumyluron, cyanazine, cybutrin, cycloate , Cyclosulfamuron, cyacryldim, sihalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, diallate, dicamba, dichlorprop (-P), Diclofo (-methyl), Diclosulam, Dietatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethamethrin, Dimetholin Metheneamide, dimexiflom, dinitramine, diphenamide, diquat, dithiopyr, diuron, dimron, eprofodan, EPTC, esprocarb, etafluralin, etamethsulfuron (-methyl), eto Fumesate, ethoxyphene, ethoxysulfuron, etobenzanide, phenoxaprop (-P-ethyl), pentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), plazasul Ron, Florasullam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, Flumichlorak (-pentyl), Flumioxazine, Flumi Propine, flumetsulam, fluoromethuron, fluorochloridone, fluoroglycopene (-ethyl), flupoxam, flupropacyl, flupyrsulfuron (-methyl, -sodium), flurenol (-butyl ), Flulidone, fluoroxypyr (-butoxypropyl, -octyl), fluprimidol, flutamone, fluthiacet (-methyl), flutiamide, pomessafen, foramsulfuron, glufosinate (-Ammonium), glyphosate (-isopropylammonium), halosafen, halooxyphosph (-ethoxyethyl, -P-methyl), hexazinone, imazamethabenz (-methyl), imazamethafil, Imazomax, imazapic, imazaphyr, imazaquin, imazetapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), Ioxynyl, isoprophalin, isoprotu , Isourone, isoxaben, isoxaclortol, isoxaplutol, isoxapyrifop, lactofen, lenacil, linuron, MCPA, mecoprop, mefenacet, mesotrione, metamitrone, meta Zaclor, metabenzthiazuron, methopenzuron, methopromurone, (alpha-) metolachlor, methotsalam, methoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron , Naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzaline, oxadiargyl, oxadione, oxasulfuron, oxazilomethone, oxyfluorfen, Paraquat, pelargonic acid, pendimethalin, pendralline, pentoxazone, penmedipharm, picolinafen, piperophosph, pretilachlor, primisulfuron (-methyl), profluzol, promethrin, Propachlor, propanyl, propazazapov, propisochlor, procarbazone (-sodium), propizamide, prosulpoca Bro, Prosulfuron, Piraflufen (-ethyl), Pirazogil, Pyrazolate, Pirazosulfuron (-ethyl), Pyrazoxifen, Pyribenzoxime, Pyributycarb, Pyridate, Pyriditol, Pyrup Thalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinclolac, quinmerac, quinoclamine, quizaropof (-P-ethyl, -P-tefuryl), rimsulfuron, seb Toxidim, simazine, cymetrine, sulforion, sulfentrazone, sulfomethuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebutiuuron, tetraproxydim, terbutylazine, terbu Trine, tenylchlor, thiafluamide, thiazopyr, thiadiazimine, thifensulfuron (-methyl), thiobencarb, thiocarbazil, tracoximide, trialate, triasulfuron, tribenuron ( -Methyl), triclopyr, tridiphane, trituraline, trilockulfurfuron, triflusulfuron (-methyl) and tritosulfuron.

Known safeners, for example AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl), cymetrinyl, 2,4-D, DKA-24, dichlormide, dimrone, fenkle Rorim, fenchlorazole (-ethyl), flurazole, fluxofimem, furylazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG -191, oxavetrinyl, PPG-1292, R-29148 are also suitable for the mixture.

Mixtures with other known active compounds are also possible, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil remediators.

The active compounds can be used on their own, in the form of their preparations or in the form of further dilution thereof, for example in ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in conventional manner, for example by spraying, spraying, spraying or spraying.

The active compounds according to the invention can be applied both before and after germination of plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a relatively wide range. This is essentially dependent on the nature of the desired effect. Generally the amount used is 1 g to 10 kg, preferably 5 g to 5 kg of active compound per hectare of soil surface.

As mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, wild plant species and plant varieties or plant species and plant varieties obtained by conventional biological breeding methods such as hybrid breeding or protoplast fusion as well as these parts are treated. In another preferred embodiment, transgenic plants and plant varieties (genetically modified organisms) obtained genetically and in combination with conventional methods, if appropriate, are treated. The terms 'part', 'part of the plant' or 'plant part' have been described above.

Particularly preferably, plants of the plant variety which are commercially available or in use in each case are treated according to the invention. Plant varieties are to be understood as plants having certain properties ('characteristics') obtained by conventional breeding, mutagenesis or recombinant DNA techniques. These may be of cultivar, biotype or genotype.

Depending on the plant species or plant variety, their location and growing conditions (soil, climate, growing season, nutrients), an additive ('raising') effect may also be produced by treatment according to the invention. Thus, for example, reduction in the application rate of substances and compositions (also in combination with other agrochemically active compounds) and / or broadening the activity spectrum and / or increasing the activity, improving plant growth, high or low temperatures, for example, which can be used according to the invention. Increased resistance, drought, or increased resistance to water or soil salts, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality and / or nutritional value of harvested products, and storage stability and / or harvested products Effects such as improved throughput may appear beyond what is actually expected.

Transgenic plants or plant varieties (ie, genetically engineered) which are preferably treated in accordance with the present invention are those that accept all plants that contain genetic material that provides particularly beneficial beneficial properties ('characteristics') to these plants upon genetic modification. Include. Examples of such properties include improved plant growth, increased high or low temperature resistance, drought, or increased resistance to water or soil salts, increased flowering, ease of harvest, increased maturity, increased crop yields, improved quality of harvested products, and / or Increased nutritional value, and increased storage stability and / or processability of the harvested product. Further particularly notable examples of such properties include increased plant defense against animal and microbial pests such as insects, mites, phytopathogenic fungi, bacteria and / or viruses, and also increased plant resistance to certain herbicidally active compounds. Examples of transgenic plants may include important crops such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, oilseed rape, and also fruit trees (opening apples, pears, citrus fruits and grape fruits), Of particular interest are corn, soybeans, potatoes, cotton and oilseed rape. Particularly important properties are the toxins formed in plants, in particular genetic material obtained from Bacillus thuringiensis (for example genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CryIF and combinations thereof) is an increase in the plant's defense against insects due to toxins formed in plants (hereinafter referred to as 'Bt plants'). Also of particular emphasis is the increased protection of the plant against fungi, bacteria and viruses due to systemically acquired resistance (SAR), cystemine, phytoalexius, eliminator and resistance genes and correspondingly expressed proteins and toxins. will be. A further particularly highlighted property is an increase in plant tolerability to certain herbicidally active compounds such as imidazolinone, sulfonylurea, glyphosate or phosphinothricin (eg the 'PAT' gene). Genes that confer the desired properties of interest can also be present in the transgenic plant in mutual combination. Examples of 'Bt plants' include YIELD GARD ^R (e.g. corn, cotton, soy), KnockOut ^R (e.g. corn), StarLink ^R (e.g. corn), Bollgard ^R (e.g. cotton), Nucotn ^R (e.g. cotton) And corn varieties, cotton varieties, soybean varieties and potato varieties available under the name NewLeaf ^R (eg potatoes). Examples of herbicide-tolerant plants include Roundup Ready ^R (glyphosate tolerant, eg corn, cotton, soybean), Liberty Link ^R (phosphinothricin tolerant, e.g. oilseed rape), IMI ^R (imidazolinone tolerant) And corn varieties, cotton varieties and soybean varieties available under the trade name STS ^R (sulfonylurea tolerant, eg maize). Examples of herbicide-tolerant plants (plants bred by conventional methods for herbicide tolerability) may also be mentioned varieties sold under the name Clearfield ^R (eg corn). Of course, the above description also applies to plant varieties which are to be developed and / or marketed in the future, having the above-mentioned characteristics or where the genetic characteristics are still left to be developed.

The above-mentioned plants can be treated in a particularly advantageous manner according to the invention using the compounds of formula (I) or mixtures of the active compounds according to the invention, in which, besides good control of weed plants, transgenic plants or plants The synergistic effects mentioned above for varieties appear. The abovementioned preferred ranges for the active compounds or mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the compounds or mixtures specifically mentioned in the present text.

The following examples illustrate the preparation and use of the active compounds according to the invention.

Preparation Example:

Example 1-1

2.80 g (8.43 mmol) of 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid, 0.945 g (8.43 mmol) A mixture of cyclohexane-1,3-dione, 2.10 g (10.1 mmol) dicyclohexylcarbodiimide and 30 ml of acetonitrile is stirred at room temperature (about 20 ° C.) for 18 hours and then filtered. The filtrate is treated with 0.335 g (3.37 mmol) trimethylsilyl cyanide and 1.70 g (16.9 mmol) triethylamine, and the mixture is stirred at room temperature for 18 hours and then concentrated under reduced pressure. The residue is stirred with 10% aqueous sodium carbonate solution and then extracted with diethyl ether. The organic phase is separated (and discarded) and the aqueous solution is acidified with concentrated hydrochloric acid and the resulting crystal product is separated by suction filtration.

This gives 2.20 g (49% of theory) of N- [2,6-dichloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -3-methyl-2-oxo-1 -Imidazolidinecarboxamide is provided.

log P (pH = 2.3): 2.07.

Similar to Example 1 and according to the general description of the preparation process according to the invention, for example, the compounds of the formula (I) listed in the following Tables 1-1 to 1-5 or the formulas (I-1), (I-) 2) or compounds of (I-3) can be prepared.

Table 1-1: Examples for Compounds of Formula (I), wherein R ¹ and R ² each represent hydrogen and Y represents hydroxyl.

Table 1-2: Examples for compounds of formula (I), wherein in each case R ¹ represents methyl in the 4-position, R ² represents methyl in the 4-position and Y represents hydroxyl.

Table 1-3: Examples for Compounds of Formula (I), wherein in each case R ¹ represents methyl at the 5-position, R ² represents hydrogen and Y represents hydroxyl.

Table 1-4: Examples for compounds of formula (I), wherein in each case R ¹ represents methyl at the 5-position, R ² represents methyl at the 5-position and Y represents hydroxyl.

Table 1-5: Examples for Compounds of Formula (I), wherein in each case R ¹ and R ² are dimethylene groups between positions 4 and 6-"(4) -CH ₂ CH _2- (6)" -Represents Y and hydroxyl.

The logP values given in Tables 1-1, 1-2, 1-3, 1-4 are determined according to EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using reversed phase column (C 18). It became. Temperature: 43 ° C.

(a) Mobile phase for determination in acidic range: 0.1% aqueous phosphoric acid, acetonitrile; 10% acetonitrile → linear gradient with 90% acetonitrile—corresponding data is shown in Table 1 as ^a) .

(b) mobile phase for measurement in the neutral range: 0.01 molar aqueous phosphate buffer, acetonitrile; 10% acetonitrile → linear gradient with 90% acetonitrile—corresponding data is shown in ^b) in ^b) .

Calibration was performed using unbranched alkan-2-ones (3-16 carbon atoms) with known logP values (determining logP values by residence time using linear interpolation between two consecutive alkanones).

UV spectra of 200-400 nm were used to determine the lambda max value as the maximum of the chromatographic signal.

Starting material of formula (III):

Example (III-1)

11.3 g (32.9 mmol) of methyl 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoate, 50 ml of water, A mixture of 50 ml of tetrahydrofuran and 1.3 g of sodium hydroxide is stirred at room temperature (about 20 ° C.) for 18 hours and then concentrated to about half of the initial volume under reduced pressure. The mixture is then extracted with diethyl ether, the organic phase is separated (and discarded) and the aqueous phase is acidified with concentrated hydrochloric acid. The obtained crystal product is separated by suction filtration.

This gave 9.1 g (81.5% of theory) of 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoic acid.

log P (pH = 2.3): 1.35.

Similar to Example (III-1), compounds of formula (III) may be prepared, for example, listed in Table 2 below.

Table 2: Examples for Compounds of Formula (III)

Starting material of formula (IIIa):

Example (IIIa-1)

12.3 g (50 mmol) methyl 2,4-dichloro-3-isocyanato-benzoate, 5.0 g (50 mmol) 1-methyl-2-oxo-imidazolidine, few drops of triethylamine And 100 ml of acetonitrile are stirred at room temperature (about 20 ° C.) for 18 hours and then concentrated under reduced pressure. The residue is then immersed in diethyl ether and the crystalline product is separated by suction filtration.

This gives 11.4 g (60% of theory) of methyl 2,4-dichloro-3-[[(3-methyl-2-oxo-1-imidazolidinyl) -carbonyl] -amino] -benzoate .

log P (pH = 2.3): 1.94.

Similar to Example (IIIa-1), for example, compounds of formula (III) listed in the following Table 3 may be prepared:

Table 3: Examples for Compounds of Formula IIIa

Example usage:

Example A

Germination test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvent in the amount mentioned above, the emulsifier in the amount mentioned above is added, and the concentrate is then diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Seeds of the test plants are sown in soil. After 24 hours, the soil is sprayed with the active compound preparation to apply a specific amount of the desired active compound per unit area. The concentration of the active compound in the spray solution is chosen such that a specific amount of the desired active compound is applied to 1000 liters of water per hectare.

After 3 weeks, the degree of damage of the plant is reported as percent damage compared to the development of the untreated control. The figures represent the following:

0% = no effect (same as untreated control)

100% = complete control

In this test, for example, the compounds of Preparation Examples 1-1, 1-2, 1-3, 1-4, 1-5 and 1-6 show very potent activity against weeds, some of which are crops, For example, it has good resistance to corn.

Example B

Post Germination Test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

1 part by weight of the active compound is mixed with the solvent in the amount mentioned above, the emulsifier in the amount mentioned above is added, and the concentrate is then diluted with water to the desired concentration to prepare a suitable formulation of the active compound.

Test plants of 5 to 15 cm in height are sprayed with the active compound preparation to apply a specific amount of the desired active compound per unit area. The concentration of the spray liquid is selected such that a specific amount of the active compound of interest is applied to 1000 l / ha of water.

After 3 weeks, the degree of damage of the plant is reported as percent damage compared to the development of the untreated control.

The figures represent the following:

0% = no effect (same as untreated control)

100% = complete control

In this test, for example, the compounds of Preparation Examples 1, 2, 3 and 4 show very potent activity against broad leaf weeds and weed grass, some of which have good crop resistance.

Example C

Test in sowing rice (greenhouse)

Solvent: 5 parts by weight of acetone

Emulsifier: alkylaryl polyglycol ether 1 part by weight

1 part by weight of the active compound is mixed with the solvents and emulsifiers in the amounts mentioned above and diluted to the desired concentration by mixing with water to prepare a suitable spray formulation.

Plant containers (dimensions: 20 cm x 20 cm x 9 cm; surface: 1/200 are) are filled with paddy soil. Sprinkle rice weeds and weeds into the soil and keep it wet. To 1.5-2 blades of rice, a dilute formulation of the active compound is applied as a spray (leaving treatment).

After 1 day treatment, the test container is watered with a depth of 3 cm. The test batch is then kept watered (water depth 3 cm).

Four weeks after application of the active compound, the degree of damage of the plant is reported as percent damage (or action on weeds) compared to the untreated control.

The figures represent the following:

0% = no effect (same as untreated control)

100% = complete control

In this test, the compounds of Production Examples 1, 2, 3, 4, 10, 16, 23, 108 exhibit very potent activity against weeds, and resistance to rice is good.

Claims (10)

Compounds of formula (I), and all possible tautomeric forms and possible salts thereof: Where Q represents O (oxygen) or S (sulfur), R ¹ represents hydrogen, halogen or in each case optionally substituted alkyl, alkylthio or aryl, R ² represents hydrogen, halogen or optionally substituted alkyl, or together with R ¹ represents O (oxygen) or alkanediyl (alkylene), R ³ is hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, Dialkylaminocarbonyl or dialkylaminosulfonyl; R ⁴ is hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl, alkylamino, dialkylamino, Dialkylaminocarbonyl or dialkylaminosulfonyl, R ⁵ is hydrogen or in each occurrence optionally substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylthio, arylsulfinyl, arylsul Phonyl, arylalkyl, or the group -C (Q) -Z, Y is hydroxyl, halogen or in each case optionally substituted alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy, alkylsulfonyloxy, alkenyloxy , Alkynyloxy, aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio, arylalkylsulfinyl or arylalkylsulfonyl Indicates Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or in each case optionally substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino, alkoxyamino, Alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydrazino, alkylsulfonylhydrazino, dialkylamino, N-alkyl-alkoxyamino, dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino, al Kenyloxyamino, alkynyl, alkynyloxy, alkynylamino, cycloalkyl, cycloalkyloxy, cycloalkylamino, cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylamino, aryl, arylcarbonyl, Aryloxy, aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio, arylalkylamino, heterocyclyl, he Rosa shows a cycle-yloxy, heterocyclyl thio, heterocyclyl amino, a group -N = (heterocyclyl), heterocyclyl-alkyl, heterocyclyl alkyl, heteroaryl recital days alkylthio or heterocyclyl-alkyl-amino, Provided that the compound N- [2,6-dichloro-3-[(3,3-dimethyl-2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide, N- [2-chloro- 3-[(2,6-dioxo-cyclohexyl) -carbonyl] -4-nitro-phenyl] -acetamide, N- [2-chloro-3-[(2,6-dioxo-cyclohexyl) -Carbonyl] -phenyl] -acetamide, and N- [2,6-dichloro-3-[(2,6-dioxo-cyclohexyl) -carbonyl] -phenyl] -acetamide. The method of claim 1, Q represents O, R ¹ represents hydrogen, halogen, or optionally halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C _1- C ₄ -alkylsulfonyl-substituted alkyl having 1 to 6 carbon atoms, alkylthio having 1 to 6 carbon atoms, or phenyl; R ² represents hydrogen, halogen, optionally halogen-substituted alkyl having 1 to 6 carbon atoms, or O (oxygen) or alkanediyl (alkylene) having 2 to 5 carbon atoms with R ¹ ), R ³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or in each case up to 4 carbon atoms in the alkyl group and in each case optionally halogen-, C ₁ -C ₄ -alkoxy -, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl Each occurrence represents an alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl having up to 4 carbon atoms in the alkyl group, R ⁴ represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen or in each case up to 4 carbon atoms in the alkyl group and in each case optionally halogen-, C ₁ -C ₄ -alkoxy -, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl Or in each case an alkylamino, dialkylamino, dialkylaminocarbonyl or dialkylaminosulfonyl having up to 4 carbon atoms in the alkyl group, R ⁵ represents hydrogen or in each case has 1 to 6 carbon atoms in the alkyl group and in each case is optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkyl, alkoxy, alkylthio, alkylsulphi Or in each case an alkenyl or alkynyl group having from 3 to 6 carbon atoms and optionally in each case a cyano- or halogen-substituted alkenyl or alkynyl, or in each case cyclo In the alkyl group 3 to 6 carbon atoms and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally representing cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted cycloalkyl or cycloalkylalkyl Or in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally nitro-, cyano-, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ - halogenoalkyl -, C ₁ -C ₄ - Al When -, C ₁ -C ₄ - halogenoalkyl alkoxy -, C ₁ -C ₄ - alkylthio -, C ₁ -C ₄ - halogenoalkyl thio -, C ₁ -C ₄ - alkyl sulfinyl -, C ₁ - C ₄ -halogenoalkylsulfinyl-, C ₁ -C ₄ -alkylsulfonyl- or C ₁ -C ₄ -halogenoalkylsulfonyl-substituted aryl, arylthio, arylsulfinyl, arylsulfonyl or arylalkyl Or a group -C (Q) -Z, Y represents hydroxyl, halogen, or in each case an alkyl group has 1 to 6 carbon atoms and in each case is optionally cyano-, halogen- or C ₁ -C ₄ -alkoxy-substituted alkoxy, alkylthio, alkylsulfy Aryl, alkylsulfonyl, alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy or alkylsulfonyloxy, in each case 3 to 6 carbon atoms and in each case optionally cyano- or halogen-substituted Alkenyloxy or alkynyloxy, or in each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety and optionally in each case nitro-, cyano-, C ₁ -C ₄ - alkyl -, C ₁ -C ₄ - halogenoalkyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - halogenoalkyl alkoxy -, C ₁ -C ₄ - alkylthio -, C ₁ -C ₄ -halogenoalkylthio-, C ₁ -C ₄ -alkylsulfinyl-, C ₁ -C ₄ -halogenoalkylsulfinyl-, C ₁ -C ₄ -alkylsulfonyl- Or C ₁ -C ₄ -halogenoalkylsulfonyl-substituted aryloxy, arylthio, arylsulfinyl, arylsulfonyl, arylcarbonyloxy, arylcarbonylalkoxy, arylsulfonyloxy, arylalkoxy, arylalkylthio , Arylalkylsulfinyl or arylalkylsulfonyl, Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, C ₁ -C ₄ -alkyl-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl, or In each case optionally cyano-, halogen-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -alkylsulfinyl- or C ₁ -C ₄ -alkylsulfonyl Substituted, alkyl having at least two carbon atoms, in each case 1 to 6 carbon atoms in the alkyl group, alkoxy, alkylthio, alkylamino, alkoxyamino, alkylhydrazino, alkylcarbonylhydrazino, alkoxycarbonylhydra Zino or alkylsulfonylhydrazino, or In each case a dialkylamino, N-alkyl-alkoxyamino or dialkylhydrazino having 1 to 4 carbon atoms in the alkyl group, or in each case 2 to 6 carbon atoms and optionally halogen-substituted Kenyl, alkenyloxy, alkenylamino, alkenyloxyamino, alkynyl, alkynyloxy or alkynylamino, or In each case 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted cycloalkyl, cyclo Alkyloxy, cycloalkylamino, cycloalkylhydrazino, cycloalkylalkyl, cycloalkylalkoxy or cycloalkylalkylamino, or In each case 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally nitro-, cyano, halogen, C ₁ -C ₄ -alkyl-, C ₁ -C ₄ -Halogenoalkyl-, C ₁ -C ₄ -alkoxy-, C ₁ -C ₄ -halogenoalkoxy- or C ₁ -C ₄ -alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy, aryloxy Carbonyl, arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy, arylalkylthio or arylalkylamino, or Optionally nitro in each case, cyano-, halogen -, C ₁ -C ₄ - alkyl -, C ₁ -C ₄ - halogenoalkyl -, C ₁ -C ₄ - alkoxy -, C ₁ -C ₄ - haloalkyl Genoalkoxy-, C ₁ -C ₄ -alkylthio-, C ₁ -C ₄ -halogenoalkylthio- or C ₁ -C ₄ -alkoxy-carbonyl- or C ₃ -C ₆ -cycloalkyl-substituted mono Cyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylthio, heterocyclylamino, group -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy, heterocyclylalkylthio Or heterocyclylalkylamino, where in each case the heterocyclyl group has up to 10 carbon atoms and additionally nitrogen (but at most 5 N atoms), oxygen (but at most 2 O atoms), sulfur (but at most two S atoms), SO and SO ₂ and optionally at least one heteroatom selected from the group consisting of octanoic (C = O), thioxo (C = S), one imino (C = NH), cyano noi mino (C = N-CN) and selected from niteuroyi diamino (C = N-NO ₂₎ group consisting of A compound of formula (I), which further contains a group and, where appropriate, the alkyl moiety contains 1 to 4 carbon atoms. The method of claim 1 or 2, R ¹ represents hydrogen, fluorine, chlorine or bromine, or in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n Or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t -Butyl, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, or phenyl, R ² represents hydrogen, fluorine, chlorine or bromine, or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl Or optionally O together with R ¹ O (oxygen), ethane-1,2-diyl, propane-1,3-diyl or butane-1,4-diyl, R ³ represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, methylthio -Ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s Or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl , R ⁴ represents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or in each case optionally fluorine-, chlorine-, methoxy-, ethoxy-, methylthio -Ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s Or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl Indicates R ⁵ represents hydrogen or in each case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propyl Sulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or dimethylamino or diethylamino Or in each case optionally represent fluorine-, chlorine- and / or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, or in each case optionally No-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted Ropropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine- , Methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy Difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl, or C (Q) -Z, Y represents hydroxyl, formyloxy, fluorine, chlorine or bromine, or in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methyl Thio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted methoxy, ethoxy, n- or i-propoxy , Methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxy Carbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethyl Sulfenyloxy, n- or i-propylsulfonyloxy, or in each case optionally fluorine-, chlorine- and / or bromine-substituted propenyloxy, butenyloxy, pro Pinyloxy or butynyloxy, or in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i- , s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio -, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methylsulfinyl-, ethylsulfinyl-, trifluoromethylsulfinyl-, methylsulfonyl-, ethylsul Phenyl- or trifluoromethylsulfonyl-substituted phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenyl Methylsulfinyl or phenylmethylsulfonyl, Z represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino, or Cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, or Ethylsulfonyl-substituted methyl, or In each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphi Nyl-, ethylsulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl-, or ethylsulfonyl-substituted ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n Or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, methy Methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, methylhydrazino, ethyl hydrazino, n- or i-propylhydrazino, n- , i-, s- or t-butylhydrazino, Dimethylamino, diethylamino, N-methyl-methoxyamino or dimethylhydrazino, or In each case optionally fluorine-, chlorine- and / or bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl, pentynyl, propenyloxy, butenyloxy, pentene Iloxy, propenylthio, butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino, propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethynyl, propynyl, butynyl Or pentynyl, propynyloxy, butynyloxy, pentynyloxy, propynylamino, butynylamino or pentynylamino, In each case optionally cyano-, fluorine-, chlorine-, bromine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohex Siloxy, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylhydrazino, cyclobutylhydrazino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl Or cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i- Propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl, naphthyloxy, naphthylthio, naphthylamino, phenylmethyl, phenyl Ethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, petylethylthio, phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy, naphthylmethylamino or naphthyl Ethylamino, or Furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, Dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylamino, thienylmethyl, tenylmethylamino, dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy, dithiolyl Olanylmethylamino, pyrrolidinyl, pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrroylylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, already Dazolinyl, imidazolylmethyl, imidazolinylmethyl, oxoimidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylamino, dihydrooxazolyl (oxazolinyl ), Tetrahydrojade Zolyl (oxazolidinyl), isoxazolyl, isoxazolylamino, dihydroisoxazolyl (isoxazolinyl), tetrahydroisoxazolyl (isoxazolidinyl), tetrahydro- (2H) -1,2 -Oxazin-2-yl, oxazolylmethyl, thiazolyl, thiazolylamino, thiazolylmethyl, dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), thiazolinylthio, thiazolin Monoamino, oxothiazolidinyl, cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino, triazolylamino, oxotriazolinyl, thioxotriazolinyl, oxotetrazolinyl, oxoterazolinyl Methyl, tetrazolylmethyl, dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, dithiayl, dithiaylmethyl, dithiaylmethoxy, dithiaylmethylamino, piperidinyl, piperidinyl Amino, oxopiperidinyl, 2-oxo-1,3-diaza-cycle Lohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinyl Thio, pyridinylamino, 2- (1H) -pyridinimino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylthio, pyrimidinylamino, pyrimidinylmethyl or pyrimidine Among the groups consisting of monomethoxy, in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-, s- or t-part Thio-, difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocycles 1, heterocyclyloxy, heterocyclylamino, group -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino. The method according to any one of claims 1 to 3, R ¹ represents hydrogen or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, or phenyl Indicates, R ² represents hydrogen, or in each case optionally represents fluorine- or chlorine-substituted methyl, ethyl, n- or i-propyl, or optionally together with R ^{1 is} ethane-1,2-diyl, propane-1, 3-diyl or butane-1,4-diyl, R ³ is hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, Methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsul Phonyl or dimethylaminosulfonyl, R ⁴ is hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl, Methylthiomethyl, methylsulfinylmethyl, methylsulfonylmethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsul Phonyl or dimethylaminosulfonyl, R ⁵ represents hydrogen or in each case optionally represents cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl Or methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl , Ethylsulfonyl, methylamino, ethylamino, n- or i-propylamino or dimethylamino, or in each case optionally fluorine- and / or chlor-substituted propenyl, butenyl, propynyl or butynyl Or in each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl Or optionally in each case nitro-, cyano-, fire -Chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylmethyl or phenylethyl, or group -C (Q) -Z, Y represents hydroxyl or, in each case, optionally fluorine- and / or chlorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methyl Sulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyloxy, propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-pro Foxoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy, methylsulfonyloxy, ethylsulfonyloxy, n- or i-propylsulfonyloxy , In each case optionally represents fluorine-, chlorine-, and / or bromine-substituted propenyloxy, butenyloxy, propynyloxy or butynyloxy, In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, Difluoromethylthio-, trifluoromethylthio-, methylsulfinyl-, ethylsulfinyl-, trifluoromethylsulfinyl-, methylsulfonyl-, ethylsulfonyl- or trifluoromethylsulfonyl-substituted Phenyloxy, phenylthio, phenylsulfinyl, phenylsulfonyl, phenylcarbonyloxy, phenylcarbonylmethoxy, phenylsulfonyloxy, phenylmethoxy, phenylmethylthio, phenylmethylsulfinyl or phenylmethylsulfonyl Z represents amino, cyanoamino, hydrazino, or Cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulfinyl-, ethyl Sulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl-, or ethylsulfonyl-substituted methyl, In each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-, methylsulphi Nyl-, ethylsulfinyl-, n- or i-propylsulfinyl-, methylsulfonyl- or ethylsulfonyl-substituted ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, methoxyamino, ethoxyamino , n- or i-propoxyamino, methylhydrazino, ethyl hydrazino, n- or i-propylhydrazino, n-, i-, s- or t-butylhydrazino, or dimethylamino, N- Methylmethoxyamino or dimethylhydrazino, or In each case optionally fluorine- and / or chlor-substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenyl Amino, butenylamino, propenyloxyamino, butenyloxyamino, ethynyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino or butynylamino, or In each case optionally cyano-, fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylamino , Cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopentylhydrazino, cyclohexylhydrazino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Pentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino, or In each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluor Rhomethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- or i- Propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy, phenylmethylthio, phenyl Ethylthio, phenylmethylamino or phenylethylamino, or Furyl, tetrahydrofuryl, furyloxy, tetrahydrofuryloxy, furylamino, tetrahydrofurylamino, furylmethyl, tetrahydrofurylmethyl, furylmethoxy, tetrahydrofurylmethoxy, furylmethylamino, tetrahydrofurylmethylamino, Dioxolanyl, dioxolanylmethyl, dioxolanylmethoxy, dioxolanylmethylamino, thienyl, thienylmethyl, dithiolanyl, dithiolanylmethyl, dithiolanylmethoxy, dithiolanylmethylamino, pyrrolidinyl , Pyrrolidinylamino, oxopyrrolidinyl, pyrroylyl, indolyl, pyrrolyylmethyl, pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl, imidazolinyl, imidazolylmethyl , Imidazolinylmethyl, oxoimidazolinyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, oxazolylmethyl, dihydrooxazolyl (oxazolinyl), tetrahydrooxazolyl (oxa Zolidinyl), isoxazolyl, Dihydroisoxazolyl (isoxazolinyl), tetrahydro- (2H) -1,2-oxazin-2-yl, tetrahydroisoxazolyl (isoxazolidinyl), thiazolyl, thiazolylmethyl, di Hydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl), thiazolimino, oxothiazolidinyl, cyanoiminothiazolidinyl, oxadiazolylamino, thiadiazolylamino, oxotriazolyl , Oxotetrazolylmethyl, terrazolylmethyl, oxotetrazolinyl, oxotetrazolylmethyl, tetrazolylmethyl, dioxanyl, dioxanylmethyl, dioxanylmethoxy, dioxanylmethylamino, ditianyl, Ditianylmethyl, ditianylmethoxy, ditianylmethylamino, triazolylamino, piperidinyl, piperidinylamino, 2- (1H) -pyridinimino, oxopiperidinyl, 2-oxo-1,3- Diaza-cyclohexyl, 2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diaza-cycloheptyl, Morpholinyl, morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino, pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy, pyrimidinylmethyl or pyrimidinylmethoxy In the group consisting of, in each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t- Butyl-, difluoromethyl-, trifluoromethyl-, dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- or i- Propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, difluoromethylthio-, trifluoromethylthio-, methoxycarbo Nyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl, heterocyclyloxy , Heterocyclylamino, group -N = (heterocyclyl), heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino. The method according to any one of claims 1 to 4, R ¹ and R ² represent hydrogen, R ³ represents hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl, R ⁴ represents hydrogen, fluorine, chlorine, methyl, ethyl, trifluoromethyl, trichloromethyl, methoxy, ethoxy, methylsulfonyl or ethylsulfonyl, R ⁵ represents hydrogen, Y represents hydroxyl, the compound of formula (I). Compound of Formula (I-2): Where Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and Z have one of the meanings set forth in any one of claims 1 to 5. Reaction of cyclohexanedione of formula (II) with the substituted benzoic acid of formula (III) or reactive derivatives thereof, if appropriate in the presence of a dehydrating agent, if appropriate in the presence of one or more reaction aids and, if appropriate Let's If appropriate, the resulting compound of formula (I) is then subjected to an electrophilic or nucleophilic substitution and / or oxidation or reduction reaction in the usual manner within the definition of the substituent, or to the compound of formula (I) A process for the preparation of a compound of formula (I) according to any one of claims 1 to 5 and a compound of formula (I-2) according to claim 6 characterized in that it is converted to a salt by means of: Where R ¹ , R ² , R ³ , R ⁴ , R ⁵ , Q and Z have the meanings set forth in any one of claims 1 to 5. A herbicidal composition comprising at least one compound of formula (I) according to any one of claims 1 to 5 and a conventional bulking agent. Use of at least one compound according to any one of claims 1 to 5 or a composition according to claim 8 for controlling unwanted plants. A method for controlling unwanted plants, characterized in that at least one compound according to any one of claims 1 to 5 or a composition according to claim 8 acts on unwanted plants and / or their habitats.