EP1503994A1

EP1503994A1 - Substituted (thioxo)carbonylamino phenyl uraciles

Info

Publication number: EP1503994A1
Application number: EP03729934A
Authority: EP
Inventors: Hans-Georg Schwarz; Roland Andree; Dorothee Hoischen; Joachim Kluth; Karl-Heinz Linker; Anton Institut Catala Invt. Quimica VIDAL-FERRAN; Mark Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-05-02
Filing date: 2003-04-22
Publication date: 2005-02-09
Also published as: AU2003240459A1; CA2484280A1; BR0309872A; MXPA04010863A; AU2003240459B2; JP2005535585A; US20060089262A1; US7521396B2; WO2003093244A1; AR039469A1; DE10219434A1

Abstract

The invention relates to compounds of formula (I), in which Q, R1, R2, R3, R4, R5, R6 and R7 have the meanings as cited in the description, to a method for the production thereof, and to their use as herbicides.

Description

Substituted (Thioxo carbonylaminophenyl-uracile

The invention relates to new substituted (thioxo) carbonylaminophenyl-uracils, ner processes for their preparation and their use as plant treatment agents, in particular as herbicides.

Certain substituted aryluracils are already known (for example EP-A-408 382, US 5,084,084, US 5,127,935, US 5,154,755, EP-A-563,384, US 5,356,863, JP-A-09 048 761 - cited in Chem. Abstracts 126: 238387 , WO 99/21837 A,

US 6,303,783). However, these compounds have so far not been particularly important because they have a number of disadvantages.

New substituted (thioxo) carbonylaminophenyluracils of the general formula (I)

in which

represents oxygen or sulfur,

, 1

R represents hydrogen, amino or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy,

R represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, halogen or C 1 -C ₄ -alkoxy-substituted alkyl or alkoxycarbonyl each having 1 to 6 carbon atoms in the alkyl groups, R represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms,

R represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R represents cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted by halogen substituted alkyl or alkoxy each having 1 to 6 carbon atoms,

R for hydrogen, for optionally by cyano, carboxy, halogen, dC ₄ -

Alkoxy, C ₁ -C ₄ alkylthio, CC ₄ -Alkylsulfmyl, C ₁ -C ₄ alkylsulfonyl, Cι-C ₄ - alkylcarbonyl or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkyl having 1 to 6 carbon atoms, in each case optionally by cyano, halogen or -CC ₄ -alkoxy substituted alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each having 3 to 6 carbon atoms in the alkenyl or alkynyl groups, for each cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl or cycloalkylalkylsulfonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally substituted by cyano, halogen or C ₁ -C alkyl 1 to 4 carbon atoms in the alkyl part, each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, - - haloalkyl, -C-C ₄ - A lkoxy, C _! -C ₄ haloalkoxy or C ₁ -C alkoxycarbonyl substituted aryl, arylalkyl, arylcarbonyl, arylalkylcarbonyl,

Arylsulfonyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, halogen, C 1 -C ₄ alkyl, C 1 -C ₄ haloalkyl, C 1 -C ₄ alkoxy , C ₁ -C ₄ -Halogenalkoxy or -C-C ₄ - alkoxy-carbonyl substituted heterocyclylcarbonyl, heterocyclylalkylcarbonyl, heterocyclylsulfonyl or heterocyclylalkylsulfonyl, each with up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms as ring members - the heterocyclyl groups optionally also 1 or 2 -SO groups, 1 or 2 -SO ₂ groups, 1 or 2 Contain -CO groups or 1 or 2 -CS groups, and

R ⁷ for alkoxycarbonylalkoxy, alkoxycarbonylalkylthio, alkenyloxycarbonylalkoxy, alkenyloxycarbonylalkylthio, alkynyloxycarbonylalkoxy, alkynyloxycarbonylalkylthio, carbamoylalkoxy, carbamoylalkylthio, alkylaminocarbonylalkoxy, alkylamino-carbonylalkyloxycarbonylaminoyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyalkylyloxyoxyalkyl N-alkyl-N-alkenylaminocarbonylalkylthio, dialkenylaminocarbonylalkoxy, dialkenylaminocarbonylalkylthio, N-alkyl-N-alkynylaminocarbonylalkoxy, N-alkyl-N-alkynylaminocarbonylalkylthio, each with up to 6 carbon atoms in the alkyl, alkenyl or alkynyl -groups stands, or

R ⁷ for hydroxyamino, for N-alkyl-hydroxyamino, alkoxyamino, N-alkylalkoxyamino, alkoxycarbonylalkoxyamino or N-alkylalkoxycarbonylalkoxyamino each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by halogen, for alkenyloxyamino optionally substituted by halogen, N-alkyl-alkenyloxyamino, N-alkenyl-alkoxyamino or N-alkenyl-alkenyloxyamino, each with 3 to 6 carbon atoms in the alkenyl groups and optionally 1 to 6 carbon atoms in the alkyl groups, for cycloalkyloxyamino or N-alkylcycloalkyloxyamino, each with 3 to 6 carbon atoms in the

Cycloalkyl groups and optionally 1 to 6 carbon atoms in the alkyl group, or for aryloxyamino or N-alkyl-aryloxyamino, each optionally substituted by halogen, each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 6 carbon atoms in the alkyl group, or R ^{7 is} cyanoalkylamino with 1 to 6 carbon atoms, for dialkylamino optionally substituted by cyano, halogen, C ₁ -C alkoxy or C ₁ -C alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by cyano, Halogen or C ₁ -C - alkoxy-carbonyl-substituted N-alkyl-N-alkenyl-amino or N-alkyl-N-alkynylamino, each having up to 6 carbon atoms in the alkyl, alkenyl or alkynyl groups, or for Dialkenylamino or dialkinylamino each having up to 6 carbon atoms in the alkenyl or alkynyl groups, or

R ⁷ represents in each case optionally substituted by nitro, cyano, halo, Cι-C ₄ -alkyl, C - haloalkyl, C ₁ -C ₄ -alkoxy, C ₄ haloalkoxy, C ₁ -C alkylthio, C ₁ - C - haloalkylthio, C ₁ -C -alkoxy-carbonyl, C -C ₆ -cycloalkyl or phenyl-substituted heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-alkyl-heterocyclylamino, N-alkyl-heterocyclylalkylamino or -N = (heterocyclyl), wherein the monocyclic or bicyclic heterocyclyl group up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen atoms and / or 1 or 2 sulfur atoms and optionally additionally 1 or 2 -SO groups and / or 1 or 2-SO ₂ groups and / or 1 or 2 -CO groups and / or 1 or 2 -CS groups, and optionally the

Alkyl group contains 1 to 6 carbon atoms, or

R ⁷ is bonded via a N, optionally substituted by nitro, cyano, halo, Cι-C ₄ -alkyl, C haloalkyl, C ₁ -C alkoxy, C ₁ -C ₄ haloalkoxy, alkylthio CC, Cι- C ₄ haloalkylthio, C ₁ -C alkoxy carbonyl, C ₁ -C ₄ -

Alkoxy-carbonyl-C2-alkoxy, C ₁ -C ₄ alkylcarbonylamino, C ₁ -C alkoxycarbonylamino, C ₂ -C ₄ alkylenedioxy, C ₃ -C ₆ cycloalkyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle with up to 9 carbon atoms, up to 5 nitrogen atoms and optionally additionally 1 or 2 oxygen or sulfur atoms and optionally additionally 1 or 2 -SO-Grappen, 1 or 2 -Sθ ₂ groups, 1 or 2 -CO groups, 1 or 2 -CS groups or a cyanimino group (C = N-CN),

including the possible stereoisomeric forms

found.

In the definitions, the hydrocarbon chains, such as alkyl or alkenyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.

Optionally substituted radicals can be mono- or polysubstituted; in the case of multiple substitution, the substituents can be the same or different.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are defined as follows:

Q preferably represents oxygen.

, 1

R preferably represents hydrogen, amino or alkyl having 1 to 5 carbon atoms substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy.

R preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted alkyl or alkoxycarbonyl each having 1 to 5 carbon atoms in the alkyl groups. 3

R preferably represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 5 carbon atoms which is optionally substituted by fluorine, chlorine or bromine.

R preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,

Chlorine or bromine.

R preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally substituted by fluorine, chlorine or bromine alkyl or alkoxy each having 1 to 5 carbon atoms.

R preferably represents hydrogen, optionally by cyano, carboxy, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl, acetyl, propionyl, n- or i-

Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl-substituted alkyl having 1 to 5 carbon atoms, for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl each having 1 to 5 carbon atoms in the alkyl groups, for alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each optionally substituted by fluorine, chlorine or bromine, each having 3 to 5 carbon atoms in the alkenyl or alkynyl groups, each optionally substituted by cyano, fluorine, Chloro, bromine, methyl, ethyl, n- or i-propyl substituted cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl or cycloalkylalkylsulfonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, each optionally by Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, chloro-difluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted aryl, arylalkyl, arylcarbonyl, arylalkylcarbonyl, arylsulfonyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 3 carbon atoms in the alkyl part, or for each optionally by nitro,

Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n -, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclyl, heterocyclyl Heterocyclyl-sulfonyl or heterocyclylalkylsulfonyl, each with up to 5 carbon atoms, up to 4 nitrogen atoms and / or an oxygen or sulfur atom as ring members - the heterocyclyl groups optionally also being an -SO group, an -SO ₂ group, 1 or contain 2 -CO groups or 1 or 2 -CS groups.

R ⁷ preferably represents in each case optionally substituted by halogen alkoxycarbonylalkoxy, Aikoxycarbonylalkylthio, Alkenyloxycarbonylalkoxy, Alkenyloxycarbonylalkylthio, Alkinyloxycarbonylalkoxy, alkynyloxy carbonylalkylthio, Carbamoylalkoxy, Carbamoylalkylthio, alkylamino carbonylalkoxy, Alkylaminocarbonylalkylthio, dialkylaminocarbonylalkoxy, Dialkylaminocarbonylalkylthio, Dialkenylaminocarbonylalkoxy, dialkenyl aminocarbonylalkylthio, Dialkinylaminocarbonyloxy or carbonylalkylthio with Dialkinylamino- each up to 5 carbon atoms in the alkyl,

Alkenyl or alkynyl groups.

R ⁷ further preferably represents hydroxyamino, in each case optionally by

Halogen substituted N-alkyl-hydroxyamino, alkoxyamino, N-alkylalkoxyamino, alkoxycarbonylalkoxyamino or N-alkylalkoxycarbonylalkoxyamino, each with 1 to 5 carbon atoms in the alkyl groups, for each optionally substituted by halogen-substituted alkenyloxyamino, N-alkyl-alkenyloxyamino, N-alkenyl-alkoxyamino or N-alkenyl-alkenyloxyamino, each with 3 to 5 carbon atoms in the alkenyl groups and optionally 1 to 5 carbon atoms in the alkyl groups, for cycloalkyloxyamino or N- Alkyl-cycloalkyloxyamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl group, or for each aryloxyammo or N-alkyl-aryloxyamino optionally substituted by halogen, each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 3 Carbon atoms in the alkyl group.

R ⁷ further preferably represents cyanoalkylamino having 1 to 5 carbon atoms, dialkylamino optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl in each case 1 to 5 carbon atoms in the alkyl groups, for N-alkyl-N-alkenyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl amino or N-alkyl-N-alkynylamino, each with up to 5 carbon atoms in the alkyl, alkenyl or alkynyl groups, for dialkenylamino or dialkynylamino, each with up to 5 carbon atoms in the alkenyl or alkynyl groups.

R ⁷ further preferably represents in each case optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl , Cyclopentyl, cyclohexyl or phenyl substituted heterocyclyloxy, Heterocyclylthio, heterocyclylamino, N-alkyl-heterocyclylamino, N-alkyl-heterocyclylalkylamino or -N = (heterocyclyl), where the monocyclic or bicyclic heterocyclyl group has up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen atoms and / or 1 or 1 or Contains 2 sulfur atoms and optionally 1 or 2 -SO groups and / or 1 or 2 SO ₂ groups and / or 1 or 2 -CO groups and / or 1 or 2 -CS groups, and optionally the alkyl group 1 to Contains 3 carbon atoms.

R ⁷ is more preferably a bonded via N, optionally through

Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, Difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, acetylamino, propionylamino, methoxycarbonylylyamino, ethendylcarbonylamino, ethylene Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or

Phenyl-substituted, monocyclic or bicyclic nitrogen heterocycle having up to 9 carbon atoms, up to 5 nitrogen atoms and optionally additionally 1 or 2 oxygen or sulfur atoms and optionally additionally 1 or 2 -SO groups, 1 or 2 -SO ₂ groups, 1 or 2 -CO groups, 1 or 2 -CS groups or a cyanimino group (C = N-

CN).

R particularly preferably represents hydrogen, amino or in each case methyl, ethyl, n- or i-propyl, n-, i- or s- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. butyl. R particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, n- or i-propoxycarbonyl.

R particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine or bromine.

.4 R particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine.

R particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i- substituted by fluorine, chlorine or bromine.

Propoxy.

R particularly preferably represents hydrogen, in each case optionally by cyano, carboxy, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl , for acetyl, propionyl, n- or i-butyroyl which are optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,

Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i- or s-butylsulfonyl, each optionally with fluorine , Chlorine or bromine-substituted propenyl, butenyl, propenylsulfonyl, butenylsulfonyl, propynyl or butinyl, for each optionally substituted by cyano, fluorine, chlorine,

Bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentyl, carbonyl, cyclohexylcarbonyl, Cyclopropylmethylcarbonyl, cyclobutyl methylcarbonyl, Cyclopentylmethylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, Cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexyl sulfonyl, Cyclopropylmethylsulfonyl, Cyclobutylmethylsulfonyl, cyclopentyl methylsulfonyl or cyclohexylmethylsulfonyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy,

Trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, phenylpropyl, benzoyl, phenylacetyl, phenylsulfylsulfonyl or optionally through nitro, cyano, fluorine, chlorine, bromine, methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- Butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl,

Heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclylmethylsulfonyl where the heterocyclyl grouping is selected from the series furyl, tetrahydroforyl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxolidoliazolyl, oxazolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolyloloxylololyloloxylololidolazoloylazolidylazolidylazolidylazolidylazolidylazolidylazolidylazolidylazolidylazolidylazole , Imidazolyl,

Imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl.

particularly preferably represents methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n- or i-propoxycarbonylmethoxy, n-, i-, s- or t-butoxycarbonyl- methoxy, methoxycarbonylethoxy, ethoxycarbonylethoxy, n- or i-propoxycarbonylethoxy, n-, i-, s- or t-butoxycarbonylethoxy, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, n- or i-propoxycarbonylmethylthio, n-, i-, s- or t-butoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbonylethylthio, n- or i-propoxycarbonylethylthio, n-, i-, s- or t-

Butoxycarbonylethylthio, Propenyloxycarbonylmethoxy, butenyloxy carbonylmethoxy, Propenyloxycarbonylethoxy, Butenyloxycarbonylethoxy, Propenyloxycarbonylmethylthio, Butenyloxycarbonylmethylthio, propenyl oxycarbonylethylthio, Butenyloxycarbonylethylthio, methoxy propynyloxycarbonyl, Butinyloxycarbonylmethoxy, Propinyloxycarbonylethoxy, butynyl oxycarbonylethoxy, Propinyloxycarbonylmethylthio, butynyloxycarbonyl methylthio, Propinyloxycarbonylethylthio, Butinyloxycarbonylethylthio, carbamoylmethoxy, carbamoylethoxy, carbamoylmethylthio, Carbamoyl-ethylthio, methylaminocarbonylmethoxy, ethylaminocarbonylethoxy, n- or i-propylaminocarbonylmethoxy, n-, i-, s- or t-butylaminocarbonylmethoxy,

Methylaminocarbonylethoxy, ethylaminocarbonylethoxy, n- or i-propylaminocarbonylethoxy, n-, i-, s- or t-butylaminocarbonylethoxy, methylaminocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethylthio, n-, n- t-butylaminocarbonylmethylthio, methylaminocarbonylethylthio, ethylaminocarbonylethylthio, n- or i-

Propylaminocarbonylethylthio, n-, i-, s- or t-Butylaminocarbonylethylthio, dimethylaminocarbonylmethoxy, Diethylaminocarbonylmethoxy, dimethyl- aminocarbonylethoxy, Diethylaminocarbonylethoxy, dimethylamino carbonylmethylthio, Diethylaminocarbonylmethylthio, dimethylamino carbonylethylthio, Diethylaminocarbonylethylthio, Dipropenylaminocarbonyl- methoxy, Dipropenylaminocarbonylethoxy, Dipropenylaminocarbonylmethyl- thio, Dipropenylaminocarbonylethylthio, Dipropinylaminocarbonylmethoxy , Dipropinylaminocarbonylethoxy, Dipropinylaminocarbonylmethylthio or Dipropinylaminocarbonylethylthio. R ⁷ furthermore particularly preferably stands for hydroxyamino, for N-methyl-hydroxyamino, N-ethyl-hydroxyamino, Nn-propylhydroxyamino, Ni-propyl-hydroxyamino, methoxy ino, ethoxyamino, n- or i-propoxyamino, n-, i -, s- or t-butoxyamino, N-methyl-methoxyamino, N-ethylmethoxyamino, N-methylethoxyamino, methoxycarbonylmethoxyamino, ethoxycarbonyl-methoxyamino, n- or i-propoxycarbonylmethoxyamino, methoxycarbonyl-ethoxyamino, ethoxycarbonylethoxyamino, n- or i-propoxy , N-methyl-methoxycarbonylmethoxyamino, N-methyl-ethoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonylmethoxyamino, N-methyl-i-propoxycarbonylmethoxyamino, N-methyl-methoxycarbonylethoxyamino, N-methyl-ethoxycarbonylethoxyamino, N-methyl-n -propoxycarbonyl- ethoxyamino, N-methyl-i-propoxycarbonylethoxyamino, propenyloxyamino, butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl-ethoxyamino, N-propenyl-N-propoxyamino propenyl-i propoxyami no, N-propenyl-propenyloxyamino, for cyclopentyloxyamino, cyclohexyloxyamino, N-methyl-cyclopentyloxy-amino or N-methyl-cyclohexyloxyamino, or for phenoxyamino or N-methyl-phenoxyamino.

R ⁷ furthermore particularly preferably represents cyanomethylamino, cyanoethylamino,

Cyanopropylamino or cyanobutylamino, for each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, dimethylamino, diethylamino, dipropylamino or dibutylamino, each optionally by Cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted N-methyl-N-propenylamino, N-methyl-N-butenylamino, N-ethyl- N-propenylamino, N-ethyl-N-butenylamino, N-propyl-N-propenylamino, N-propyl-N-butenylamino, N-butyl-N-propenylamino, N-butyl-N-butenylamino, N-methyl- N-propynylamino, N-methyl-N-butynylamino, N-ethyl-N-propynylamino, N-ethyl-N-butynylamino, N-propyl-N-propynylamino, N-propyl-N- bμtinylamino, N-butyl-N-propynylamino, N-butyl-N-butinylamino, or for dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino.

R ⁷ further particularly preferably represents in each case optionally through nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, or ethylthio, n- Propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methoxycarbonylmethoxy, acetylamino Ethylenedioxy, propylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-methyl-heterocyclyllamino, N-ethyl-heterocyclylamino, N-methyl-heterocyclylmethylmethylamino = (Heterocyclyι), the heterocyclyl grouping being selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxaz olyl, thiazolyl, thiazolinyl, thiazolidinyl, cyanimine thiazolidinyl, imidazolyl, imidazolinyl, 2-

Oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl, pyrimidinyl.

R ⁷ furthermore particularly preferably represents a bond via N, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, Dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n -, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl Imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxo-oxazolidinyl, isoxazolidinyl, thiazolinyl, 2-oxo-thiazolidinyl, isothiazolidinyl, 1-oxo-isothiazolidinyl, 1.1 -Dioxo-isothiazolidinyl, 2-cyano-iminothiazolidinyl, triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 1,2-oxaza-cyclohexyl, 1,2-oxaza-cyclohexenyl, 2-oxo-l, 3-diaza-cyclohexyl , Morpholinyl, piperazinyl.

R very particularly preferably represents hydrogen, amino or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.

2

R very particularly preferably represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy.

R very particularly preferably represents hydrogen, fluorine, chlorine or methyl or ethyl which is in each case optionally substituted by fluorine or chlorine.

4

R very particularly preferably represents hydrogen, fluorine or chlorine.

R very particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine,

Chlorine, bromine, or in each case optionally substituted by fluorine or chlorine, methyl, ethyl, methoxy or ethoxy.

R very particularly preferably represents hydrogen, in each case optionally by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy,

Methylthio, ethylthio, methylsulfmyl, ethylsulfmyl, methylsulfonyl or Ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally acetyl, propionyl, n- or i-butyroyl, substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i -Propyl-sulfonyl, n-, i- or s-butylsulfonyl, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl , Cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, eth r i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylsulfonyl or optionally through nitro, cyano, fluorine, chlorine, bromine, methyl,

Heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclylmethylsulfonyl where the heterocyclyl grouping is selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolylylylolololylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylolylololiazolylazolidylazolidolazoloylazolidylazolidylazolidylazolidylazolidylazolidylazole , Imidazolyl,

very particularly preferably represents methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n- or i-propoxycarbonylmethoxy, n-, i-, s- or t-butoxycarbonylmethoxy, methoxycarbonylethoxy, ethoxycarbonylethoxy, n- or i- propoxycarbonylethoxy, n-, i-, s- or t-butoxycarbonylethoxy, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, n- or i-propoxycarbonylmethylthio, n-, i-, s- or t-butoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbonylethylthio, n- or i-propoxycarbonylethylthio, n- -, s- or t-butoxycarbonylethylthio, propenyloxycarbonylmethoxy, butenyloxycarbonylmethoxy, propenyloxycarbonylethoxy, butenyloxycarbonylethoxy, propenyloxycarbonylmethylthio, butenyloxycarbonylmethylthio, propenyloxycarbonylethylthio, butenyloxycarbonylethyloxyoxyoxyoxyyloxyoxyoxyoxyoxyyloxyoxyoxyoxyoxyoxyyloxyoxyoxyoxyoxyyloxyethyloxyoxyoxyoxyyloxyethyloxyoxyoxyoxyyloxyethyloxyoxyoxyoxyoxyyloxyethyloxyoxyoxyyloxycarbonyl

Butynyloxycarbonylethoxy, propynyloxycarbonylmethylthio, butynyloxycarbonylmethylthio, propynyloxycarbonylethylthio, butynyloxycarbonylethylthio, methylaminocarbonylmethoxy, ethylaminocarbonylethoxy, n- or i- propylaminocarbonylmethoxy, n-, i-, s- or t-butylaminocarbonylyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyyloxyoxyoxyyloxyoxyyloxyoxyyloxyoxyoxyyloxyoxyoxyyloxyoxyoxyoxyoxyoxyoxyoxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethyloxyoxyoxyethylene , n-, i-, s- or t-butylaminocarbonylethoxy, methylaminocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethylthio, n-, i-, s- or t-butylaminocarbonylmethylthio, methylaminocarbonylethylthio, ethylethyl, ethylaminio Propylaminocarbonylethylthio, n-, i-, s- or t-butylaminocarbonylethylthio,

Dimethylaminocarbonylmethoxy, diethylaminocarbonylmethoxy, dimethylaminocarbonylethoxy, diethylaminocarbonylethoxy, dimethylaminocarbonylmethylthio, diethylaminocarbonylmethylthio, dimethylaminocarbonylethylthio, diethylaminocarbonylethylthio, dipropenylaminocarbonylmethoxy dipropylyloxydipylethylphenyl methoxy, dipropenyl methoxy, dipropenyl methoxy Dipropinylaminocarbonylethoxy, Dipropinylaminocarbonylmethylthio or Dipropinylaminocarbonylethylthio.

R ⁷ furthermore very particularly preferably represents hydroxyamino, N-methyl-hydroxyamino, N-ethyl-hydroxyamino, Nn-propylhydroxyamino, Ni

Propyl-hydroxyamino, methoxyamino, ethoxyamino, n- or i-propoxy-amino, n-, i-, s- or t-butoxyamino, N-methyl-methoxyamino, N-ethyl-methoxyamino, N-methylethoxyamino, methoxycarbonylmethoxyammo, ethoxycarbonylmethoxyamino, n- or i-propoxycarbonylmethoxyamino, methoxycarbonylethoxyamino, ethoxycarbonylethoxyamino, n- or i-

Propoxycarbonylethoxyamino, N-methyl-methoxycarbonylmethoxyamino, N-methyl-e hoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonyl-methoxyamino, N-methyl-i-propoxycarbonylmethoxyamino, N-methyl-methoxycarbonylethoxyamino, N-methyl-ethoxycarbonylethoxyamino, N-methyl -propoxycarbonylethoxyamino, N-methyl-i-propoxycarbonylethoxy-amino, propenyloxyamino, butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl-ethoxy-amino, N-propenyl-n-propoxyamino , N-propenyl-i-propoxyamino, N-propenyl-propenyloxyamino, or for phenoxyamino or N-methyl-phen-oxyamino.

R ^{7 also} very particularly preferably represents cyanoethylamino, cyanopropylamino or cyanobutylamino, dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, di-n-butylamino or di-i-butylamino, for N-methyl-cyanoethylamino, N-ethyl-cyanoethylamino, Nn-propyl-cyano-ethylamino, Ni-propyl-cyanoethylamino, N-methyl-fluoroethylamino, N-ethyl-fluoroethylamino, Nn-propyl-fluoroethylamino, Ni-propyl-fluoroethyl-a ino, N-methyl -methoxyethylamino, N-ethyl-methoxyethylamino, N-methyl-ethoxyethylamino, N-ethyl-ethoxyethylamino, N-methyl-methoxy-carbonylmethylamino, N-methyl-ethoxycarbonylmethylamino, N-methyl-methoxycarbonylethylamino, N-methyl-ethoxycarbonylethylamino, for N- Methyl-N-propenylamino, N-methyl-N-butenylamino, N-ethyl-N-propenylamino, N-ethyl-N-butenylamino, N-propyl-N-propenylamino, N-propyl-N-butenylamino, N- Butyl-N-propenylamino, N-butyl-N-butenylamino, N-methyl-N-propynylamino, N-methyl-N-butynylamino, N-ethyl-N-propynylamino, N-ethyl-N-butynylamino, N- Propyl-N-propynylamino, N-propyl-N-butynylamino, N-butyl-N-propynylamino or N-butyl-N-butynylamino, or for dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino.

R ^{7 also} very particularly preferably represents in each case optionally by nitro,

Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio,

Trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl-substituted heterocyclyloxy, heterocyclyl-thio-hetero-hetero-heterocyclyl-heterocyte cyclylamino, N-methyl-heterocyclylmethylamino or -N = (heterocyclyl), where the heterocyclyl grouping is selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazoloxazoloxazolyl, oxazoloxyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl, oxazolyl , Thiazolyl, thiazolinyl, thiazolidinyl, cyaniminthiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl,

Oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl, pyrimidinyl.

R ^{7 also} very particularly preferably represents a bonded via N, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- , s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl-substituted, substituted or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxo-l, 3-oxaza-cyclopentyl (2-oxo-oxazolidinyl), isoxazolidinyl, thiazolinyl, 2-oxothiazolidinyl, 1,1-dioxo-isothiazolidinyl, 2-cyaniminothiazolidinyl, triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo 1,3-diaza-cyclohexyl, morpholinyl or piperazinyl.

R ⁶ most preferably represents hydrogen, in each case methyl, ethyl, acetyl, methoxycarbonyl or ethoxycarbonyl optionally substituted by fluorine, chlorine, methoxy or ethoxy.

R ⁶ particularly preferably represents hydrogen, methyl or ethyl.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred.

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which a combination of those listed above as being particularly preferred

Meanings exist. A very particularly preferred group are those compounds of the formula (I) in which

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

4

R represents hydrogen, fluorine or chlorine,

, 5 R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine or chlorine, each optionally optionally substituted by fluorine, Chloro or methyl substituted cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, for each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, dif luormethoxy, trifluoromethoxy,

Chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocycliclmethylsulfonyl, where the heterocyclyl-furyl group is selected from T-group, T is selected from the group consisting of T, and t-group, selected from T, , Pyrrolyl, Pyrrolinyl, Pyrrolidinyl, Oxopyrrolidinyl, Pyrrolyl, Pyrazolyl, Oxazolyl, Oxazolinyl, Oxazolidinyl, Isoxazolyl, Thiazolyl, Thiazolinyl, Thiazolidinyl, Cyaniminothiazolidinyl, Imidazolyl, Im idazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imide-azolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl , Piperazinyl, and

for methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n- or i-propoxycarbonylmethoxy, n-, i-, s- or t-butoxycarbonylmethoxy, methoxycarbonylethoxy, ethoxycarbonylethoxy, n- or i-propoxycarbonylethoxy, n-, i-, s- or t -Butoxycarbonylethoxy, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, n- or i-propoxycarbonylmethylthio, n-, i-, s- or t-butoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbonylethylthio, n- or i-propoxycarbonylethylthio, n-, i-, s- or t-butoxycarbonylethylthio,

Propenyloxycarbonylmethoxy, butenyloxycarbonylmethoxy, propenyloxycarbonylethoxy, butenyloxycarbonylethoxy, propenyloxycarbonylmethylthio,

Butenyloxycarbonylmethylthio, propenyloxycarbonylethylthio, butenyloxycarbonylethylthio, propynyloxycarbonylmethoxy, butynyloxycarbonylmethoxy, propynyloxycarbonylethoxy, butynyloxycarbonylethoxy, propynyloxycarbonylmethylthio, butynyloxycarbonylmethylthio, propynyloxycarbonyl ethylthio, butinyloxycarbonylethylthio, methylaminocarbonylmethoxy, ethylaminocarbonylethoxy, n- or i-propylaminocarbonylmethoxy, n-, i-, s- or t-butylaminocarbonylmethoxy, methylaminocarbonylethoxy, ethylaminocarbonylethoxy, n- or i-propylaminocarbonyl- ethoxy, n- Butylaminocarbonylethoxy, methylaminocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethylthio, n-, i-, s- or t-butylaminocarbonylmethylthio, methylaminocarbonylethylthio, ethylamino-carbonylethylthio, n- or i-nyl- , s- or t-butylaminocarbonylethylthio, dimethylaminocarbonylmethoxy, diethylaminocarbonylmethoxy, dimethylaminocarbonylethoxy, diethylaminocarbonylethoxy, dimethylaminocarbonylmethylthio, diethylaminocarbonylmethylthio, dimethylaminocarbonylethylthio, diethylaminocropylylethylaminophenyl, diphenyl Dipropinylaminocarbonylmethoxy, dipropinylaminocarbonylethoxy, dipropinylaminocarbonylmethylthio or dipropinylaminocarbonylethylthio.

Another very particularly preferred group are those compounds of the formula (I) in which

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

.2

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

.4 R represents hydrogen, fluorine or chlorine, R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfmyl, ethylsulfmyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or

Ethoxycarbonyl substituted methyl or ethyl, for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each optionally substituted by fluorine or chlorine methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or chlorine propenyl,

Butenyl, propynyl or butynyl, for cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, each optionally substituted by fluorine, chlorine or methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl,

Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or optionally phenylsulfonyl or phenylsulfonyl through nitro, cyano, fluorine, chlorine,

Bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl-substituted heterocyclylcarbonyl, heterocyclylmethylcarbonylsulfonylcyllylcyllmethylcarbonylsulfonylcyllylcyllmylcarbonylsulfonylcyllmylcarbonylsulfonylcyllylcyllmylcarbonylsulfonylcyllcyllcyllmylcarbonylsulfonylcyllcyllmylcarbonyl Hylcyllcyllcyllmylcarbonyl Hylcyllcyllcyllcyllmylcarbonylsulfyl Hylcylcyllcyllcyllcyllmylcarbonyl Hylcyllcyllcyllmyl Carbonylsilylcyllcyllmyl Carbonylsulfonyl, , wherein the heterocyclyl grouping is selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolididinyl, isoxazolyl, thiazolyl, thiazolylidylidolothiazolinylidiazolidine , Imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imide- azolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

R ⁷ for hydroxyamino, for N-methyl-hydroxyamino, N-ethyl-hydroxyamino, N-n-propylhydroxyamino, Ni-propyl-hydroxyamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s - or t-butoxyamino, N-methyl-methoxyamino, N-ethylmethoxyamino, N-methylethoxyamino, methoxycarbonylmethoxyammo, ethoxycarbonylmethoxyamino, n- or i-propoxycarbonylmethoxyamino, methoxycarbonylethoxyamino, ethoxycarbonylethoxyamino, n- or i-propoxycarbonylethoxyamino methoxycarbonylmethoxyamino, N-methyl-ethoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonylmethoxyamino, N-methyl-i-propoxycarbonylmethoxyamino, N-methyl-methoxycarbonylethoxyamino, N-methyl-ethoxycarbonylethoxyamino, N-methyl-n-propoxycarbonylethoxyamino, N-methyl-i-propoxycarbonylethoxyamino, propenyloxyamino, butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl-ethoxyamino, N-propenyl-n-propoxyamino, N-propenyl-i- propoxyamino, N-propenyl-propenyloxyamino, or represents phenoxyamino or N-methylphenoxyamino.

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

.2

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl, R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy substituted acetyl,

Propionyl, methoxycarbonyl, ethoxycarbonyl, for methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl, each optionally substituted by fluorine, chlorine or methyl Cyclopropylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-Propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenyl or methylylsulfonyl, optionally by nitro, or nitro for methylsulfonyl , Chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- , n-, i-, s- or t-butoxycarbonyl-substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocycliclmethylsulfonyl, the heterocyclyl group being selected from the series furyl, tetrahydrofuryl, thienylrolyl, pyrrole, pyrrole dinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl ( azolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

R ⁷ for cyanoethylamino, cyanopropylamino or cyanobutylamino, for dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, di-n-butylamino or di-i-butylamino, for N-methyl-cyanoethylamino, N-ethyl - cyanoethylamino, Nn-propyl-cyanoethylamino, Ni-propyl-cyanoethylamino, N-methyl-fluoroethylamino, N-ethyl-fluoroethylamino, Nn-propyl-fluoroethylamino, Ni-propyl-fluoroethylamino, N-methyl-methoxyethylamino, N-ethyl - methoxyethylamino, N-methyl-ethoxyethylamino, N-ethyl-ethoxyethylamino, N-methyl-methoxycarbonylmethylamino, N-methyl-ethoxycarbonylmethylamino, N-methyl-methoxycarbonylethylamino, N-methyl-ethoxycarbonyl-ethylamino, for N-methyl-N- propenylamino, N-methyl-N-butenylamino, N-ethyl-N-propenylamino, N-ethyl-N-butenylamino, N-propyl-N-propenylamino, N-propyl-N-butenylamino, N-butyl-N- propenylamino, N-butyl-N-butenylamino, N-methyl-N-propynylamino, N-methyl-N-butynylamino, N-

Ethyl-N-propynylamino, N-ethyl-N-butynylamino, N-propyl-N-propynyl-a ino, N-propyl-N-butynylamino, N-butyl-N-propynylamino or N-butyl-N-butynylamino, or represents dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino.

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl, R represents cyano or trifluoromethyl,

3

R represents hydrogen, chlorine or methyl,

R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl substituted methyl or ethyl, each for acetyl, propionyl, methoxycarbonyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy, Ethoxycarbonyl, for methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine or chlorine, for cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, each optionally substituted by fluorine, chlorine or methyl, for each if necessary

Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylmethyl,

Phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl-substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclicl ethylsulfonyl, where the heterocyclyl grouping is selected from the series furyl, tetrahydrofuryl, pyrienyl, thienyl, thienyl , Oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclo-vinylidyl (2 ), Triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy,

Chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s - or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl-substituted heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-methyl-heterocyclylamino, N-methyl-heterocyclylmethylamino or -N = (heterocyclylation) is selected, where is selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminthiazolidyl, imidazolidinyl, imidazidinyl, imido- l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl, pyrimidinyl. Another very particularly preferred group are those compounds of the formula (I) in which

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

4

R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

.6

R for hydrogen, for each methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy substituted acetyl,

Propionyl, methoxycarbonyl, ethoxycarbonyl, for methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl, each optionally substituted by fluorine, chlorine or methyl Cyclopropylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, phenylmethyl, Phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl, n , i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocycliclmethylsulfonyl, where the heterocyclyl grouping is selected from the series furyl, tetrahydrofuryl, thienyl, oxyryrylylrole, pyrrolrolylrole, pyrrolylrolidol Pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imid-azolidinyl) yl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

for a bonded via N, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- , s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl-substituted, substituted or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl, 2-oxo-1,3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxo-l, 3-oxaza-cyclopentyl (2-oxo-oxazolidinyl), isoxazolidinyl, thiazolinyl, 2-oxo-thiazolidinyl, 1,1-

Dioxo-isothiazolidinyl, 2-cyaniminothiazolidinyl, triazolyl, oxotriazolinyl, Thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl.

The general definitions given above or those specified in preferred areas apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new substituted (thioxo) carbonylaminophenyl-uracile of the general

Formula (I) are characterized by strong and selective herbicidal activity.

The new substituted (thioxo) carbonylaminophenyl uracils of the general formula (I) are obtained if iso (thio) cyanatophenyl uracils of the general formula (II)

in which

Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above,

with compounds of the general formula (III)

HR ⁷ (III)

in which R ^{7 has} the meaning given above,

if appropriate in the presence of one or more reaction auxiliaries and, if appropriate, in the presence of one or more diluents,

and optionally the substituted (thioxo) carbonylaminophenyluracils of the general formula (Ia) thus obtained

in which

Q, R, R, R, R, R and R have the meanings given above,

with compounds of the general formula (IV)

XR ⁶ (TV)

in which

R ⁶ has the meaning given above with the exception of hydrogen and

X represents halogen (in particular chlorine, bromine or iodine), or optionally also acetyloxy, propionyloxy, methoxysulfonyloxy or ethoxysulfonyloxy, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents.

If, for example, 3- (2,4-dichloro-5-isothiocyanato-phenyl) -1-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione and N, O-dimethyl-hydroxylamine are used as starting materials, then the The course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the (thioxo) carbonylaminophenyluracils to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In formula (II), Q, R ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably have those meanings which have already been mentioned above as preferred, particularly preferred or as in connection with the description of the compounds of the formula (I) according to the invention have very particularly preferably been given for Q, R ¹ , R ² , R ³ , R ⁴ and R ⁵ .

With the exception of the compound, the starting materials of the general formula (II) are 3- (4-chloro-2-fluoro-5-isothiocyanato-phenyl) -l-methyl-6-trifluoromethyl-2,4- (1H, 3H) - pyrimidinedione (cf. US-6303783) not yet known from the literature; with the exception of the compound 3- (4-chloro-2-fluoro-5-isothiocyanato-phenyl) -l-methyl-6- trifluoromethyl-2,4- (1H, 3H) -pyrimidinedione also as new substances the subject of the present application.

The iso (thio) cyanatophenyl-uracile of the general formula (II) is obtained if aminophenyl-uracile of the general formula (V)

in which

R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given above,

with phosgene (or diphosgene) or thiophosgene, optionally in the presence of a reaction auxiliary, such as e.g. Diazabicyclo [2.2.2] octane, and in the presence of a diluent, e.g. Acetone, toluene, xylene or chlorobenzene

Implemented temperatures between 0 ° C and 150 ° C and after the reaction, the volatile components were distilled off under reduced pressure (cf. the preparation examples). The compounds of formula (V) are known compounds.

The further compounds to be used as starting materials are by

Formulas (III) and (IV) generally defined. Herein, R ⁶ or R ⁷ preferably have those meanings which are preferred above, particularly preferred in connection with the description of the compounds of the formula (I) according to the invention,

(7 moves, very particularly preferred, or has been given as being most preferred for R or R, respectively.

The starting materials of the formulas (III) and (IN) are known synthetic chemicals. The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium - -methanolate, -ethanolat, -n- or -i-propanolat, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, 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, 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).

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent. Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, 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 or 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-formamide, N-methyl-pyrrolidone or hexamethylphosphoric acid 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, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and

120 ° C.

The process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - 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 equimolar amounts. However, it is also possible to use one of the components in a larger excess. The

The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. The processing is carried out according to customary methods (cf. the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used. The active compounds according to the invention can be used, for example, in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda,

Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lamium, Lammium Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala,

Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon,

Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochlo

Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sciφus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum,

Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants. Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth. The active compounds according to the invention for controlling weeds in permanent crops, for example forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm,

Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds according to the invention can also be used in certain concentrations or application rates for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesired wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Under plant parts, all above-ground and underground

Parts and organs of plants, such as shoot, leaf, flower and root understood are, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and in the case of propagation material, in particular in the case of seeds, furthermore by single- or multi-layer coating.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymers

Substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silica, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite waste liquor and

Methylcellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%. The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine,

Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzfendizone, Benzobicyclon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromoximutide, Bromofen Bromoxynü, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben,

Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidone (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (- propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron sulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, dialate, dicamba,

Dichloφrop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramiqu, Diuronid, Diphenamide, Diphenamid, Diphenamid, Diphenamid, Diphenamid Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), Ethofumesate, Ethoxyfen, Ethoxysulfüron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl), Flazasulfuron Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flufenpyr, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone, Fluoroglycupox (methyl Fluprop-acil, Fluφyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (- butoxypropyl, -meptyl), Fluφrimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Foramsulfuron, Glufosinate (-ammonium), Glyphosate (-isopropyl-ammonium), Halosafen, Haloxyfop (-ethoxyethyl, -P -methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazapyr , Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Isopropalin, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Ketospirodox, Lactofen, Lenacil, Linurecet, MCPA, MCPA mitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, orben oxadazonone, norflurazonon, norflurazonon, norflurazonone Oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazole, profoxydim, pro metryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (sodium), propyzamide, prosulfocarb, prosulfuron, pyrafϊufen (ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (ethyl), pyrazoxyfen, pyribenzoxox, pyridutoximine, pyridutoxim, pyributoxim, pyributoxim Pyridatol, Pyriftalid, Pyriminobac (- methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalofop (-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone - Sulfometurzone - Sulfometurzone methyl), sulfosate, sulfosulfuron, tebutam, tebutihuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamides, thiazo-pyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydiasulfonon, triallonium, triallonate, triallate, triallate, triallate , Triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.

Known safeners are also suitable for the mixtures, for example

AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, Dichlormid, Dymron, Fenclorim, Fenchlorazole (-ethyl), Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl ), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

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

The amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars and their parts occurring wildly or obtained by conventional organic breeding methods, such as crossing or protoplast fusion, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms) and their parts are treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Among plant varieties plants with certain properties ("traits") are obtained which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemicals

Active substances, better growth of the cultivated plants, increased tolerance of the cultivated plants to high or low temperatures, increased tolerance of the cultivated plants against drought or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yield, higher quality and / or higher nutritional value of crop products, higher

Shelf life and / or workability of the harvested products possible, which go beyond the expected effects.

The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants to certain herbicides Agents. Examples of transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton and rapeseed are highlighted. The traits that are particularly emphasized are the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA, CryliTA, CrylTIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF as well as their combinations) are produced in the plants (hereinafter referred to as "Bt plants"). The increased defense of plants against fungi, bacteria and niren by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties ("traits"). The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active ingredients, for example

Imidazolinones, sulfonylureas, glyphosate or phosphinothricin (e.g. "PAT" gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties which are sold under the trade names YIELD

GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Νucotn® (cotton) and ΝewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosates e.g. maize, cotton, soybeans), Liberty

Link® (tolerance against phosphinothricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance against sulfonylureas eg maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to future developed or future plant varieties with these or future-developed genetic properties ("traits").

The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

The active ingredients are also suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials, and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight. The application takes place in a customary manner adapted to the application forms.

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats,

Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infested hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.

The active compounds according to the invention are used in the neterinary sector in a known manner by enteral administration in the form of, for example, tablets,

Capsules, watering, drenching, granules, pastes, boluses, the feed-through method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal Application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), des

Washing, powdering and with the help of shaped bodies containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in

Use formula (I) as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10,000 times dilution, or use them as a chemical bath. The active ingredients are also suitable for controlling animal pests, in particular insects, arachnids and mites, which occur in closed rooms, such as, for example, apartments, factory halls, offices, vehicle cabins and others. To control these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products.

They are effective against sensitive and resistant species and against all stages of development.

They are used in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, as granules or pellets in lures or bait stations.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples:

example 1

A mixture of 2.50 g (6.1 mmol) of 3- (4-bromo-2-fluoro-5-isocyanato-phenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione, 0 , 96 g (6.1 mmol) of ethyl piperidine-3-carboxylate, 2 drops of triethylamine and 30 ml of acetonitrile is stirred for 15 hours at room temperature (approx. 20 ° C.) and then concentrated under reduced pressure. The residue is worked up by column chromatography (silica gel, hexane / ethyl acetate, vol .: 2: 1).

1.50 g (42% of theory) of l- [2-bromo-4-fluoro-5- (3-methyl-2,6-dioxo-4-trifluoromethyl-3, 6-dihydro-2H- pyrimidine-1-yl) -phenylcarbamoyl] -piperidine-3-carboxylic acid ethyl ester.

logP (pH 2): 2.98

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of formula (I). Q stands for oxygen in all cases.

61 -

The logP values specified in the table were determined in accordance with EEC Directive 79/831 Annex N.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ⁾ .

(b) Eluents for determination in the neutral range: 0.01 molar aqueous

Phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^b) .

The calibration was carried out using unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values using the

Retention times by linear interpolation between two consecutive alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals. Starting materials of formula (II):

Example II-1

374.5 g (3.78 mol) of phosgene are placed in 1000 ml of chlorobenzene at about -20 ° C. and after removing the cooling bath with a solution of 241 g (0.63 mol) of 3- (5-amino-4 -bromo-2-fluorophenyl) - 1-methyl-6-trifluoromethyl-1 H-pyrimidine-2,4-dione in 1000 ml of chlorobenzene was added dropwise with stirring over the course of 20 minutes, the internal temperature being raised to approx. 10 ° C. increases. The reaction mixture is then stirred for approx. 30 minutes at room temperature (approx. 20 ° C.), then heated to 120 ° C. while introducing phosgene (approx. 280 g) and finally stirred at this temperature for approx. 60 minutes. For working up, the volatile components are carefully distilled off under reduced pressure (approx. 14 mbar).

276 g (86% of theory, 80.6% strength product) of 3- (4-bromo-2-fluoro-5-isocyanato-phenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2 are obtained , 4-dione, which can be used without further purification to prepare inventive compounds of the formula (I). Example 11-2

0.50 g (1.07 mmol) of 3- (5-amino-4-cyano-2-fluorophenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione are dissolved in 50 ml of acetone submitted with 0.24 g (1.23 mmol) of chloroformic acid trichloromethyl ester ("diphosgene") added dropwise and the mixture is stirred for 2 hours at room temperature (approx. 20 ° C). The volatile components are then carefully distilled off under reduced pressure.

The product obtained in this way as a residue can be used without further purification for the preparation of Nerbindungen of formula (I) according to the invention.

Analogously to Examples II-1 and 11-2, for example, the Nerbindungen of formula II listed in Table 2 below can also be prepared.

Table 2: Examples of the compounds of the formula (II)

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, it is mixed

1 part by weight of active ingredient with the stated amount of solvent, adds the stated amount of emulsifier and dilutes the concentrate with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of active ingredient in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 2, 3, 4, 5, 6, 1, 8, 9, 10, 20, 21, 22, 24, 25, 26, 27, 28, 30, 31, 32, 37 show , 38, 39, 44, 45, 46, 47, 48 and 49 with good tolerance to crops such as corn, wheat, soybeans and sugar beets, strong action against weeds. Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 2, 3, 4, 5, 6, 7, 8, 9, 10, 21, 24, 25, 26, 27, 28, 30, 31, 32, 33, 34, 35 , 36, 37, 38, 39, 40, 41, 42, 44, 45, 46, 47 and 48 with good tolerance to crops, such as Wheat, effective against weeds.

Claims

claims

Compounds of the formula

in which

represents oxygen or sulfur,

R represents hydrogen, amino or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen or C 1 -C 6 -alkoxy,

2

R represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy-substituted alkyl or alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups,

R represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms,

R represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen, R represents cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted by halogen alkyl or alkoxy each having 1 to 6 carbon atoms,

R represents hydrogen, optionally by cyano, carboxy, halogen,

C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfionyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ alkylcarbonyl or C ₁ -C 4 alkoxy- carbonyl-substituted alkyl having 1 to 6 carbon atoms, each for alkyl carbonyl, alkoxycarbonyl or alkylsulfonyl each having 1 to 6 and optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy

Carbon atoms in the alkyl groups, for alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each optionally substituted by halogen, each having 3 to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl optionally substituted by cyano, halogen or C 1 -C ₄ -alkyl, Cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl or cycloalkylalkylsulfonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, halogen, C ₁ -C alkyl, d- GrHalogenalkyl, C ₁ -C ₄ alkoxy,

Cι-C ₄ -haloalkoxy or C ₁ -C ₄ -alkoxy-carbonyl substituted aryl, arylalkyl, arylcarbonyl, arylalkylcarbonyl, arylsulfonyl or aryl alkylsulfonyl having in each case 6 or 10 carbon atoms groups in the aryl and optionally 1 to 4 carbon atoms in the alkyl moiety, or for each optionally by nitro, cyano, halogen, -CC ₄ -

Alkyl, Cι-C haloalkyl, C ₁ -C ₄ -alkoxy, C ₄ -haloalkoxy or Cι-C ₄ -alkoxy-carbonyl-substituted heterocyclylcarbonyl, hetero- cyclylalkylcarbonyl, heterocyclylsulfonyl or heterocyclylalkyl sulfonyl each having up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms as ring members - the heterocyclyl groups in each case optionally also contain 1 or 2 -SO groups, 1 or 2 -SO ₂ groups, 1 or 2 -CO groups or 1 or 2 -CS groups, and

R ⁷ for alkoxycarbonylalkoxy, alkoxycarbonylalkylthio, alkenyloxycarbonylalkoxy optionally substituted by halogen,

Alkenyloxycarbonylalkylthio, alkynyloxycarbonylalkoxy, alkynyloxycarbonylalkylthio, carbamoylalkoxy, carbamoylalkylthio, alkylaminocarbonylalkoxy, alkylaminocarbonylalkylthio, dialkylaminocarbonylalkoxy, dialkylaminocarbonylalkylthio, N-alkyl-N-alkenylalkoxy, alkenylaminoyl aminyl aminylcarbonyl

Dialkenylaminocarbonylalkoxy, dialkenylaminocarbonylalkylthio, N-alkyl-N-alkynyl-aminocarbonylalkoxy, N-alkyl-N-alkynyl-amino-carbonylalkylthio each having up to 6 carbon atoms in the alkyl, alkenyl or alkynyl groups, or

R ⁷ for hydroxyamino, for N-alkyl-hydroxyamino, alkoxyamino, N-alkylalkoxyamino, alkoxycarbonylalkoxyamino or N-alkylalkoxycarbonylalkoxyamino each having 1 to 6 carbon atoms in the alkyl groups, each optionally substituted by halogen, for each optionally substituted by halogen substituted alkenyloxy- amino, N-alkyl-alkenyloxyamino, N-alkenyl-alkoxyamino or N-alkenyl-alkenyloxyamino, each with 3 to 6 carbon atoms in the alkenyl groups and optionally 1 to 6 carbon atoms in the alkyl groups, for cycloalkyloxyamino or N-alkyl-cycloalkyl-oxyamino, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 6 carbon atoms in the alkyl group, or for aryloxyamino or N-alkyl-aryloxyamino, each optionally substituted by halogen, each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 6 carbon atoms in the alkyl group , or R ⁷ for cyanoalkylamino having 1 to 6 carbon atoms, for dialkylamino optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups, each optionally by Cyano, halogen or C ₁ -C ₄ alkoxy-carbonyl-substituted N-alkyl-N-alkenyl-amino or N-alkyl-N-alkynylamino, each having up to 6 carbon atoms in the alkyl, alkenyl or alkynyl groups , or represents dialkenylamino or dialkinylamino, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, or

R ⁷ represents in each case optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ - alkyl, _{Cι-C4-haloalkyl,} Cι-C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ - alkylthio, C ₁ -C haloalkylthio, -C -C alkoxycarbonyl, C ₃ -C ₆ - cycloalkyl or phenyl substituted heterocyclyloxy, heterocyclylthio, heterocyclylamino, N-alkyl-heterocyclylamino, N-alkyl-heterocyclicalkylamino or -N = (Heterocyclyl), the monocyclic or bicyclic heterocyclyl group having up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen atoms and / or 1 or 2 sulfur atoms and optionally additionally 1 or 2 -SO groups and / or 1 or 2 -SO ₂ groups and / or 1 or

Contains 2 -CO groups and / or 1 or 2 -CS groups, and optionally the alkyl group contains 1 to 6 carbon atoms, or

R ⁷ is bonded via a N, optionally substituted by nitro, cyano, halogen, _Cι-C4 alk l, Cι-C ₄ haloalkyl, Ci-C ₄ alkoxy, C ₁ -C ₄ -

Haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C haloalkylthio, Cι-C ₄ - alkoxy-carbonyl, C ₁ -C ₄ -alkoxy-carbonyl-C ₁ -C ₂ -alkoxy, C ₄ alkyl - Carbonylamino, C ₁ -C ₄ alkoxy-carbonylamino, C ₂ -C ₄ alkylenedioxy, C ₃ -C ₆ cycloalkyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle with up to 9 carbon atoms, up to 5 nitrogen atoms and optionally additionally 1 or 2 acid Substance or sulfur atoms and optionally additionally 1 or 2 - SO groups, 1 or 2 -SO ₂ groups, 1 or 2 -CO groups, 1 or 2 -CS groups or a cyanimino group (C = N-CN ) stands.

2. Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen,

, 1 R for hydrogen, amino or optionally by cyano, fluorine,

Chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted alkyl having 1 to 5 carbon atoms,

2

R represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted alkyl or alkoxycarbonyl each having 1 to 5 carbon atoms in the alkyl groups,

3

R represents hydrogen, fluorine, chlorine, bromine or alkyl having 1 to 5 carbon atoms which is optionally substituted by fluorine, chlorine or bromine,

4

R for hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or

Bromine stands,

.5

R represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally substituted by fluorine, chlorine or bromine alkyl or alkoxy each having 1 to 5 carbon atoms,

R for hydrogen, for optionally by cyano, carboxy, fluorine,

Chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl or ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted alkyl with 1 to 5 carbon atoms, each optionally with cyano, fluorine, chlorine, bromine,

Methoxy, ethoxy, n- or i-propoxy substituted alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl, each with 1 to 5 carbon atoms in the alkyl groups, for alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl, each optionally substituted by fluorine, chlorine or bromine, each with 3 to 5 Carbon atoms in the

Alkenyl or alkynyl groups, each for cycloalkyl, cycloalkylalkyl, cycloalkylcarbonyl, cycloalkylalkylcarbonyl, cycloalkylsulfonyl or cycloalkylalkylsulfonyl each having 3 to 6 carbon atoms in each case substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl part, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n- , i-, s- or t-butoxycarbonyl substituted aryl, arylalkyl, arylcarbonyl, arylalkylcarbonyl, arylsulfonyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 3 carbon atoms n in the alkyl part, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy , Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t- Butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylalkylcarbonyl, heterocyclylsulfonyl or heterocyclylalkylsulfonyl each having up to 5 carbon atoms, up to 4 nitrogen atoms and / or one oxygen or sulfur atom as ring members - the heterocyclyl groups optionally also each

-SO group, an -SO ₂ group, 1 or 2 -CO groups or 1 or 2 -CS groups contain, and

Alkenyloxycarbonylalkylthio, alkynyloxycarbonylalkoxy, alkynyloxycarbonylalkylthio, carbamoylalkoxy, carbamoylalkylthio, alkylaminocarbonylalkoxy, alkylaminocarbonylalkylthio, dialkylaminocarbonylalkoxy, dialkylaminocarbonylalkylthio, dialkenylaminocarbonylamyloxycarbonyl, alkylaminoalkylamyloxycarbonyl, alkenylcarbonylalkoxy, dialkylaminocylyloxycarbonyl, alkenyloxycarbonyl -groups stands,

R ⁷ for hydroxyamino, for N-alkyl-hydroxyamino, alkoxyamino, N-alkylalkoxyamino, alkoxycarbonylalkoxyamino or N-alkylalkoxycarbonylalkoxyamino each having 1 to 5 carbon atoms in the alkyl groups, each optionally substituted by halogen, for alkenyloxy optionally substituted by halogen amino, N-alkyl-alkenyloxyamino, N-alkenyl-alkoxyamino or N-

Alkenyl-alkenyloxyamino, each with 3 to 5 carbon atoms in the alkenyl groups and optionally 1 to 5 carbon atoms in the alkyl groups, for cycloalkyloxyamino or N-alkylcycloalkyloxyamino, each with 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 carbon atoms in the alkyl group, or for each optionally substituted by halogen Aryloxyamino or N-alkyl-aryloxyamino, each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 3 carbon atoms in the alkyl group,

R ⁷ for cyanoalkylamino having 1 to 5 carbon atoms, for dialkylamino optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, each having 1 to 5 carbon atoms in the alkyl groups, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, N-alkyl-N-alkenylamino or N- Alkyl-N-alkynylamino, each with up to 5 carbon atoms in the alkyl, alkenyl or alkynyl groups, represents dialkenylamino or dialkynylamino, each with up to 5 carbon atoms in the alkenyl or alkynyl groups,

R for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,

Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxy-carbonyl, n-carbonyl, carbonyl -, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted heterocyclyloxy, heterocyclylthio, heterocycliclarnino, N-alkyl-heterocyclylamino, N-alkyl-heterocyclylalkylamino or -N = (heterocyclyl stands, wherein the monocyclic or bicyclic heterocyclyl group up to 6 carbon atoms, up to 5 nitrogen atoms and / or 1 or 2 oxygen atoms and / or 1 or 2

Sulfur atoms and optionally 1 or 2 -SO groups xmd / or 1 or 2 SO ₂ groups and / or 1 or 2 -CO groups and / or 1 or 2 -CS groups, and optionally the alkyl group contains 1 to 3 carbon atoms, or

R ⁷ for a bonded via N, optionally by nitro, cyano,

Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-

Butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methoxycarbonylmethoxy, ethoxycarbonylmethoxy, acetylamino, propionylamino, ethoxycarbonyl Propylene dioxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle with up to 9 carbon atoms, up to 5 nitrogen atoms and optionally additionally 1 or 2 oxygen or sulfur atoms and optionally additionally 1 or 2 -SO groups, 1 or 2 -SO ₂ -

Groups, 1 or 2 -CO groups, 1 or 2 -CS groups or a cyanimino group (C = N-CN).

3. Compounds of formula (I) according to claim 1, characterized in that

R represents hydrogen, amino or methyl, ethyl, n- or i-propyl, n-, i- or s-butyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,

.2

R for carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

3

R represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine, chlorine or bromine,

R for hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or

Bromine stands,

5

R represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine, chlorine or bromine,

R for hydrogen, for each optionally by cyano, carboxy, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl , Methylsulfonyl or ethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy

Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i - or s-butylsulfonyl, for propenyl, butenyl, propenylsulfonyl, butenylsulfonyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine or bromine, for each optionally by Cyano, fluorine, chlorine, bromine, methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylmethylcarbonyl, cyclohexylmethylcarbonyl, cyclohexylmylcarbonyl, cyclyl Cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, cyclopropylmethylsulfonyl, cyclobutylmethylsulfonyl, cyclopentylmethylsulfonyl or cyclohexylmethylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, phenylpropyl, benzoyl, phenyl, phenyl Phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy .

Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocycliclmethylcarbonyl, heterocyclylsulfonyl or heterocyclylme hylsulfonyl, the heterocyclyl grouping being selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolylyl, pyrrololidinyl, pyrrolidinyl, pyrrolidinyl, pyrrolidinyl Isoxazolyl, thiazolyl, thiazolinyl, thiazolididinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, Thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl, and

for methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n- or i- propoxycarbonylmethoxy, n-, i-, s- or t-butoxycarbonylmethoxy,

Methoxycarbonylethoxy, ethoxycarbonylethoxy, n- or i-propoxycarbonylethoxy, n-, i-, s- or t-butoxycarbonylethoxy, methoxycarbonylmethylthio, ethoxycarbonylmethylthio, n- or i-propoxycarbonylmethylthio, n-, i-, s- or t- Butoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbonylethylthio, n- or i-

Propoxycarbonylethylthio, n-, i-, s- or t-Butoxycarbonylethylthio, Propenyloxycarbonylmethoxy, Butenyloxycarbonylmethoxy, penyloxycarbonylethoxy Pro, Butenyloxycarbonylethoxy, Propenyloxycarbonylmethylthio, Butenyloxycarbonylmethylthio, propenyloxy carbonylethylthio, Butenyloxycarbonylethylthio, propynyloxycarbonyl methoxy, Butinyloxycarbonylmethoxy, Propinyloxycarbonylethoxy, Butinyloxycarbonylethoxy, Propinyloxycarbonylmethylthio, butynyl oxycarbonylmethylthio , Propinyloxycarbonylethylthio, butynyloxycarbonylethylthio, carbamoylmethoxy, carbamoylethoxy, carbamoylmethylthio, carbamoylethylthio, methylaminocarbonylmethoxy,

Ethylaminocarbonylethoxy, n- or i-propylaminocarbonylmethoxy, n-, i-, s- or t-butylaminocarbonylmethoxy, methylaminocarbonylethoxy, ethylaminocarbonylethoxy, n- or i-propylaminocarbonylethoxy, n-, i-, s- or t-butylaminocarbonylethoxy, Methylaminocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethylthio, n-, i-, s- or t-butylaminocarbonylmethylthio, methylaminocarbonylethylthio, ethylaminocarbonylethylthio, n- or i-propylaminocarbonylethylthio, n- or i-propylaminocarbonylethylthio, t-Buxylamino-carbonylethylthio, dimethylaminocarbonylmethoxy, diethylamino-carbonylmethoxy, dimethylaminocarbonylethoxy, diethylamino-carbonylethoxy, dimethylaminocarbonylmethylthio, diethylamino carbonylmethylthio, dimethylaminocarbonylethylthio, diethylamino-carbonylethylthio, dipropenylaminocarbonylmethoxy, dipropenyl-a inocarbonylethoxy, dipropenylaminocarbonylmethylthio, dipropenylaminocarbonylethylthio, dipropinylaminocarbonylmethoxy, dipropinylaminocethylinylaminylethyloxycarbonylethyloxycycloethylocylyloxyoxy, methylpropylaminocarbonylaminoethyl or vinyl

R ⁷ for hydroxyamino, for N-methyl-hydroxyamino, N-ethyl-hydroxyamino, Nn-propylhydroxyamino, Ni-propyl-hydroxyamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, N-methyl-methoxyamino, N-ethylmethoxyamino, N- methylethoxyamino, methoxycarbonylmethoxyammo, ethoxycarbonylmethoxyamino, n- or i-propoxycarbonylmethoxyamino, methoxycarbonylethoxyamino, ethoxycarbonylethoxyamino, n- or i-propoxycarbonylethoxyamino, n- or i-propoxycarbonylethoxyamino N-methyl-ethoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonylmethoxyamino, N-methyl-i-propoxycarbonyl-methoxyamino, N-methyl-methoxycarbonylethoxyamino, N-methyl-ethoxycarbonylethoxyamino, N-methyl-n-propoxycarbonylethoxyamino, N-methyl i-propoxycarbonylethoxyamino, propenyloxyamino,

Butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl-ethoxy-amino, N-propenyl-n-propoxyamino, N-propenyl-i-propoxyamino, N-propenyl-propenyloxyamino, represents cyclopentyloxyamino, cyclohexyloxyamino, N-methylcyclopentyloxyamino or N-methylcyclohexyloxyamino, or represents phenoxyamino or N-methylphenoxyamino,

R ⁷ for cyanomethylamino, cyanoethylamino, cyanopropylamino or cyanobutylamino, for each optionally by cyano, fluorine,

Chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, eth- oxycarbonyl, n- or i-propoxy-carbonyl substituted dimethylamino, diethylamino, dipropylamino or dibutylamino, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i -Propoxy- carbonyl substituted N-methyl-N-propenylamino, N-methyl-N-butenylamino, N-ethyl-N-propenylamino, N-ethyl-N-butenylamino, N-propyl-N-propenylamino, N-propyl-N -butenylamino, N-butyl-N-propenylamino, N-butyl-N-butenylamino, N-methyl-N-propynylamino, N-methyl-N-butynylamino, N-ethyl-N-propynylamino, N-ethyl-N -butinylamino, N-propyl-N-propynylamino, N-propyl-N-butynylamino, N-butyl-N-propynylamino, N-butyl-N-butynylamino, or represents dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino,

for each optionally by nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i- , s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, methoxycarbonylmethoxy, acetylamino, ethylenedioxy, propylenedioxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted heterocyclyloxy, heterocyclylthio,

Heterocyclylamino, N-methyl-heterocyclylamino, N-ethyl-heterocyclyllamino, N-methyl-heterocyclylmethylamino, N-ethyl-heterocycliclmethylamino or -N = (heterocyclyl), the heterocyclyl grouping being selected from the series furyluryl, tetrah Thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl,

Pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, Thiazolinyl, Thiazolidinyl, Cyaniminothiazolidinyl, Imidazolyl, Imidazolinyl, 2-Oxo-l, 3-diaza-cyclopentyl (2-Oxo-imidazolidinyl), Triazolyl, Oxotriazolinyl, Thioxotriazolinyl, Pyridinyl, Piperidinyl, Oxopiperidinyl, 3-Oxo -cyclohexyl, morpholinyl, piperazinyl, pyrimidinyl, or

R ⁷ for a bonded via N, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl,

Cyclohexyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl, 2-oxo-1, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxol dinyl, isoxazolidinyl, thiazolinyl, 2-oxothiazolidinyl,

Isothiazolidinyl, 1-oxo-isothiazolidinyl, 1,1-dioxo-isothiazolidinyl, 2-cyaniminothiazolidinyl, triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 1,2-oxaza-cyclohexyl, 1,2-oxaza-cyclohexenyl, 2- Oxo-l, 3-diaza-cyclohexyl, morpholinyl or piperazinyl.

4. Compounds of formula (I) according to claim 1, characterized in that R represents hydrogen, amino or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

2

R in each case represents methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy,

3

R represents hydrogen, fluorine, chlorine or methyl or ethyl which is in each case optionally substituted by fluorine or chlorine,

4

R represents hydrogen, fluorine or chlorine,

.5

R represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl which is optionally substituted by fluorine or chlorine

Is ethyl, methoxy or ethoxy,

R represents hydrogen, for each optionally by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl,

Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally with cyano , Fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy-substituted acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i- or s-butylsulfonyl, each for propenyl, butenyl, butenyl, propynyl or butynyl optionally substituted by fluorine, chlorine or bromine, for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentyl, optionally substituted by cyano, fluorine, chlorine, methyl or ethyl methyl, cyclohexylmethyl, cyclopropylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s - or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i- or t-butoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i- , s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl-substituted heterocyclylcarbonyl, heterocyclyl-methylcarbonyl, heterocyclylsulfonyl or heterocyclylmethylsulfonyl, the heterocyclyl grouping being selected from the series furyl, pyrryl, tetrahydryl, tetrahydryl Pyrrolinyl

Pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxiazolyl) oxolidiazidolidiazidolidiazidolidiazolylidiazolylidol (2) , Thioxotriazolinyl, Pyridinyl, Piperidinyl, Oxopiperidinyl, 2-Oxo-l, 3-diaza-cyclohexyl, Moφholinyl, Piperazinyl,

for methoxycarbonylmethoxy, ethoxycarbonylmethoxy, n- or i-

Propoxycarbonylmethoxy, n-, i-, s- or t-butoxycarbonylmethoxy, methoxycarbonylethoxy, ethoxycarbonylethoxy, n- or i-propoxycarbonylethoxy, n-, i-, s- or t-butoxycarbonylethoxy, methoxy- carbonylmethylthio, ethoxycarbonylmethylthio, n- or i-propoxycarbonylmethylthio, n-, i-, s- or t-butoxycarbonylmethylthio, methoxycarbonylethylthio, ethoxycarbonylethylthio, n- or i- propoxycarbonylethylthio, n-, i-, s- or t-butoxycarbonylethyloxycarbonyl Butenyloxycarbonylmethoxy, penyloxycarbonylethoxy Pro, Butenyloxycarbonylethoxy, Propenyloxycarbonylmethylthio, Butenyloxycarbonylmethylthio, propenyloxy carbonylethylthio, Butenyloxycarbonylethylthio, propynyloxycarbonyl methoxy, Butinyloxycarbonylmethoxy, Propinyloxycarbonylethoxy, Butinyloxycarbonylethoxy, Propinyloxycarbonylmefhylthio, butynyl oxycarbonylmethylthio, Propinyloxycarbonylethylthio, butynyloxy carbonylethylthio, Methylaminocarbonylmethoxy, Ethylaminocarbonylethoxy, n- or i-Propylaminocarbonylmethoxy , n-, i-, s- or t-butylaminocarbonylmethoxy, methylaminocarbonylethoxy, ethyl aminocarbonylethoxy, n- or i-propylaminocarbonylethoxy, n-, i-, s- or t-butylaminocarbonylethoxy, Met hylaminocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethylthio, n-, i-, s- or t-butylaminocarbonylmethylthio, methylamino-carbonylethylthio, ethylaminocarbonylethylthio, n- or i-propyl-aminocarbonylethylthio t-Butylaminocarbonylethylthio,

Dimethylaminocarbonylmethoxy, diethylaminocarbonylmethoxy, dimethylaminocarbonylethoxy, diethylaminocarbonylethoxy, dimethylaminocarbonylmethylthio, diethylaminocarbonylmethylthio, dimethylaminocarbonylethylthio, diethylaminocarbonylethylthio, dipropenylaminocarbonylaminoxycarbonylethoxy, dipropen

Dipropenylaminocarbonylmethylthio, Dipropenylaminocarbonylethylthio, Dipropinylaminocarbonylmethoxy, Dipropinylaminocarbonylethoxy, Dipropinylaminocarbonylmethylthio or Dipropinylaminocarbonylethylthio, R ⁷ for hydroxyamino, for N-methyl-hydroxyamino, N-ethyl-hydroxyamino, Nn-propylhydroxyamino, Ni-propyl-hydroxyamino,

Methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino, N-methyl-methoxyamino, N-ethylmethoxyamino, N-methylethoxyamino, methoxycarbonylmethoxyammo, ethoxycarbonylmethoxyamino, n- or i-propoxycarbonylmethoxyamino , Methoxycarbonylethoxyamino, ethoxycarbonylethoxyamino, n- or i-propoxycarbonylethoxyamino, N-methyl-methoxycarbonylmethoxyamino, N-methyl-ethoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonylmethoxyamino, N-methyl-i-propoxycarbonyl- methoxyamino, N-methyl-methoxycarbon N-methyl-ethoxycarbonylethoxyamino, N-methyl-n-propoxycarbonylethoxyamino, N-methyl-i-propoxycarbonylethoxyamino, propenyloxyamino, butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl- ethoxyamino, N-propenyl-n-propoxyamino, N-propenyl-i-propoxyamino, N-propenyl-propenyloxyamino, or represents phenoxyamino or N-methylphenoxyamino,

R ⁷ for cyanoethylamino, cyanopropylamino or cyanobutylamino, for

Dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino, di-n-butylamino or di-i-butylamino, for N-methyl-cyanoethylamino, N-ethyl-cyanoethylamino, Nn-propyl-cyanoethylamino, Ni Propyl-cyanoethylamino, N-methyl-fluoroethylamino, N-ethyl-fluoro-ethylamino, Nn-propyl-fluoroethylamino, Ni-propyl-fluoroethylamino,

N-methyl-methoxyethylamino, N-ethyl-methoxyethylamino, N-methyl-ethoxyethylamino, N-ethyl-ethoxyethylamino, N-methyl-methoxycarbonylmethylamino, N-methyl-ethoxycarbonylmethylamino, N-methyl-methoxycarbonylethylamino, N-methyl-ethoxy- carbonylethylamino, for N-methyl-N-propenylamino, N-methyl-N-butenylamino, N-ethyl-N-propenylamino, N-ethyl-N-butenylamino, N-propyl-N-propenylamino, N-propyl-N-butenylamino, N-butyl-N-propenylamino, N-butyl-N-butenylamino, N-methyl-N-propynylamino, N-methyl-N-butynylamino, N-ethyl-N-propynylamino, N-ethyl-N-butynylamino, N-propyl-N-propynylamino, N-propyl-N-butynylamino, N-butyl-N-propynylamino or N-butyl-N-butynylamino, or for Dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino,

R ⁷ for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl,

Dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n -, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyclohexyl or phenyl substituted heterocyclyloxy, heterocyclylthio, heterocycliclamino, N-mexhyl-heterocyclylamino, N-methyl-heterocyclyl-methylamino or -N = (heterocyclyl), the heterocyclyl grouping being selected from the series furyl, texrolydrofuryl, texrahydrofuryl Pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclo dinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, morpholinyl, piperazinyl, pyrimidinyl, or

R ⁷ for a bonded via N, optionally by nitro, cyano,

Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- Propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl, 2-

Oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxo-l, 3-oxaza- cyclopentyl (2-oxo-oxazolidinyl), isoxazolidinyl, thiazolinyl, 2-oxothiazolidinyl, 1, 1 - Dioxo-isothiazolidinyl, 2-cyaniminothiazolidinyl, triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl or

Piperazinyl stands.

5. Compounds of formula (I) according to claim 1, characterized in that

R ^{6 represents} hydrogen, in each case represents methyl, ethyl, acetyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by fluorine, chlorine, methoxy or ethoxy.

6. Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl, 2

R represents cyano or trifluoromethyl,

3

R represents hydrogen, chlorine or methyl,

4

R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine or chlorine, each optionally optionally substituted by fluorine, Chloro or methyl substituted cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, for each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, dif luormethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by fluorine, bromine, bromine, cyano, cyano Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-

Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, Chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclylmethyll sulfonylation is selected from the group consisting of methylsulfonyl and sulfonylation

Furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolinyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl, imidazolyl diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl,

Pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

Propoxycarbonylethylthio, n-, i-, s- or t-butoxycarbonylethylthio, propenyloxycarbonylmethoxy, butenyloxycarbonylmethoxy,

Propenyloxycarbonylethoxy, Butenyloxycarbonylethoxy, Propenyloxycarbonylmethylthio, Butenyloxycarbonylmethylthio, propenyloxy carbonylethylthio, Butenyloxycarbonylethylthio, propynyloxycarbonyl methoxy, Butinyloxycarbonylmethoxy, Propinyloxycarbonylethoxy, Butinyloxycarbonylethoxy, Propinyloxycarbonylmethylthio, butynyl oxycarbonylmethylthio, Propinyloxycarbonylethylthio, butynyloxy carbonylethylthio, Methylaminocarbonylmethoxy, ethylamino carbonylethoxy, n- or i-Propylaminocarbonylmethoxy, n -, i-, s- or t-butylaminocarbonylmethoxy, methylaminocarbonylethoxy, ethyl aminocarbonylethoxy, n- or i-propylaminocarbonylethoxy, n-, i-, s- or t-butylaminocarbonylethoxy, methylammocarbonylmethylthio, ethylaminocarbonylmethylthio, n- or i-propylaminocarbonylmethyl-thio, n-, i-, s- or t-butylaminylcarbonyl carbonylethylthio, ethylaminocarbonylethylthio, n- or i-propyl-aminocarbonylethylthio, n-, i-, s- or t-butylaminocarbonylethylthio, dimethylaminocarbonylmethoxy, diethylaminocarbonylmethoxy, dimethylaminocarbonylethoxythio, diethylaminocarbonylthio, diethylmethylocylylaminomethyl, methylethylaminodio, methylethylethylaminophenyl, dimethylethylaminoethyl, methylethylethylaminoethyl, propenylaminocarbonylmethoxy, dipropenylaminocarbonylethoxy, dipropenylaminocarbonylmethylthio, dipropenylaminocarbonylethylthio, dipropinylaminocarbonylmethoxy, dipropinylaminocarbonylethoxy, dipropinylaminocarbonylmethylthio or dipropinylaminocarbonylethylthio.

7. Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

2

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl, for hydrogen, for each methyl or ethyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, chlorine , Bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine or chlorine, each optionally substituted by fluorine, chlorine or methyl substituted cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, dif luormethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted phenyl, phenylmethyl, phenylethyl, benzoyl, phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by fluorine, cyano, bromine, bromine, cyano

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-Butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcyllyl heteryll heteryll heteryll heterocyllycylsulfyllylcylylcylylcylylsulfylyl heterocylsylcylylcylylsulfylyl heterocylsulfylyl heterocylsylcylylsulfyl, heterylcylglycylsylcylylsulfylyl, heterylcylglycylsulfyl, heterylcylglycylsulfyl, heterylcylsulfylyl, is selected from the series furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyanimino thiazolidinyl, imidazolyl, imidazolinyl, 2-oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclholinyl , Piperazinyl, and

R for hydroxyamino, for N-methyl-hydroxyamino, N-ethyl-hydroxyamino, Nn-propylhydroxyamino, Ni-propyl-hydroxyamino, methoxyamino, ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t -Butoxyamino, N-methyl-methoxyamino, N-ethylmethoxyamino, N- methylethoxyamino, methoxycarbonylmethoxyammo, ethoxycarbonylmethoxyamino, n- or i-propoxycarbonylmethoxyamino, methoxycarbonylethoxyamino, ethoxycarbonylethoxyamino, n- or i-propoxycarbonylethoxy- amino, n- or i-propoxycarbonylethoxyamino, -Methyl-ethoxycarbonylmethoxyamino, N-methyl-n-propoxycarbonylmethoxyamino, N-methyl-i-propoxycarbonyl-methoxyamino, N-methyl-methoxycarbonylethoxyamino, N-methyl-ethoxycarbonylethoxyamino, N-methyl-n-propoxycarbonylethoxyamino, N-methyl-i -propoxycarbonylethoxyamino, propenyloxyamino, butenyloxyamino, N-methyl-propenyloxyamino, N-methyl-butenyloxyamino, N-propenyl-methoxyamino, N-propenyl-ethoxy-amino, N-propenyl-n-propoxyamino, N-propenyl-i-propoxyamino, N - propenyl-propenyloxyamino, or it stands for phenoxyamino or N-methylphenoxyamino.

Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl, 2

R represents cyano or trifluoromethyl,

3

R represents hydrogen, chlorine or methyl,

4 R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

for cyanoethylamino, cyanopropylamino or cyanobutylamino, for dimethylamino, diethylamino, di-n-propylamino, di-i-propylamino,

Di-n-butylamino or di-i-butylamino, for N-methyl-cyanoethylamino, N-ethyl-cyanoethylamino, Nn-propyl-cyanoethylamino, Ni-propyl-cyanoethylamino, N-methyl-fluoroethylamino, N-ethyl-fluorine ethylamino, Nn-propyl-fluoroethylamino, Ni-propyl-fluoroethylamino, N-methyl-methoxyethylamino, N-ethyl-methoxyethylamino, N-

Methyl-ethoxyethylamino, N-ethyl-ethoxyethylamino, N-methyl-methoxycarbonylmethylamino, N-methyl-ethoxycarbonylmethylamino, N-methyl-methoxycarbonylethylamino, N-methyl-ethoxycarbonylethylamino, for N-methyl-N-propenylamino, N-methyl -N-butenylamino, N-ethyl-N-propenylamino, N-ethyl-N-butenylamino,

N-propyl-N-propenylamino, N-propyl-N-butenylamino, N-butyl-N-propenylamino, N-butyl-N-butenylamino, N-methyl-N-propynylamino, N-methyl-N-butynylamino, N-ethyl-N-propynylamino, N-ethyl-N-butynylamino, N-propyl-N-propynylamino, N-propyl-N-butynylamino, N-butyl-N-propynylamino or N-buxyl-N-butynyl- amino, or represents dipropenylamino, dibutenylamino, dipropinylamino or dibutinylamino.

9. Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen or sulfur,

, 1

R represents hydrogen, amino or methyl,

2

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

4 R represents hydrogen, fluorine or chlorine,

, 5th

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

.6

R for hydrogen, for in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl, for each optionally substituted by cyano, fluorine, Chlorine, bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each methylsulfonyl or ethylsulfonyl optionally substituted by fluorine or chlorine, for propenyl, butenyl, propynyl or butynyl optionally substituted by fluorine or chlorine, each optionally optionally substituted by fluorine, Chloropropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl substituted by chlorine or methyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl or ethoxycarbonyl, n i-propoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl,

Phenylacetyl, phenylsulfonyl or phenylmethylsulfonyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy,

Chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclylmethyll-sulfonylation is selected from the group consisting of sulfonylsulfonyls, the

for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl,

Dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n -, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t- Butoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl substituted heterocyclyloxy, heterocyclylthio, heterocycliclamino, N-methyl-heterocyclylamino, N-methyl-heterocyclyl-methylamino or -N = (heterocyclyl) is selected, with the heterocyclyl group being selected from which heterocycyl group of the series furyl, tetrahydrofuryl,

Thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyaniminothiazolidinyl, imidazolyl, imidazolinyl, 2-oxyl-2-oxo-1, 3-oxo-1-cyclo imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, pyrimidinyl.

10. Compounds of formula (I) according to claim 1, characterized in that

Q represents oxygen or sulfur,

R represents hydrogen, amino or methyl,

.2

R represents cyano or trifluoromethyl,

R represents hydrogen, chlorine or methyl,

R represents hydrogen, fluorine or chlorine,

R represents cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R for hydrogen, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxy- carbonyl or ethoxycarbonyl substituted methyl or ethyl, for each optionally substituted by cyano, fluorine, chlorine, bromine, methoxy or ethoxy substituted acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, for each optionally substituted by fluorine or chlorine methylsulfonyl or ethylsulfonyl, each optionally substituted by fluorine or Chlorine-substituted propenyl, butenyl, propynyl or butynyl, for cyclopropyl or cyclopropylmethyl, cyclopropylcarbonyl or cyclopropylsulfonyl, each optionally substituted by fluorine, chlorine or methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl or ethoxycarbonyl, n i-propoxycarbonyl substituted phenyl, phenylmethyl, phenylethyl, benzoyl,

Chlorodifluoromethoxy, fluorodichloromethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl substituted heterocyclylcarbonyl, heterocyclylmethylcarbonyl, heterocyclylsulfonyl or heterocyclylmethyll sulfonylation is selected from the group consisting of methylsulfonyl and sulfonylation

Furyl, tetrahydrofuryl, thienyl, pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl, pyrazolyl, oxazolyl, oxazolinyl, oxazolidinyl, isoxazolyl, thiazolyl, thiazolinyl, thiazolidinyl, cyanimino-thiazolidinyl, oxidazolinyl, 3-imidazolyl, imidazolyl, 2 cyclopentyl (2-oxo-imidazolidinyl), triazolyl, oxotriazolinyl, thioxotriazolinyl, Pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl, and

R for a bonded via N, optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, or ethylthio, n- Propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl or phenyl substituted, monocyclic or bicyclic nitrogen heterocycle from the series pyrrolyl, pyrrolinyl, pyrrolidinyl, oxopyrrolidinyl, pyrazolyl, imidazolyl, imidazolinyl, 2-

Oxo-l, 3-diaza-cyclopentyl (2-oxo-imidazolidinyl), 2-oxo-l, 3-oxazacyclopentyl (2-oxo-oxazolidinyl), isoxazolidinyl, thiazolinyl, 2-oxothiazolidinyl, 1, 1 - Dioxo-isothiazolidinyl, 2-cyaniminothiazolidinyl, triazolyl, oxotriazolinyl, thioxotriazolinyl, pyridinyl, piperidinyl, oxopiperidinyl, 2-oxo-l, 3-diaza-cyclohexyl, Moφholinyl, piperazinyl.

11. A process for the preparation of compounds of the formula (I) according to claim 1, characterized in that compounds of the formula (II)

in which

Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given in Claim 1,

with compounds of the general formula (III)

H-R '(HI)

in which

n

R has the meaning given in claim 1,

if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,

and optionally the compounds of formula (Ia) thus obtained

R ¹

RγNγθ R ⁷

^R3 Π W ^H (Ia) ° _R ⁴ Λ _R5

in which

Q, R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{7 have} the meanings given in Claim 1,

with compounds of the general formula (IV) XR ⁶ (IN)

in which

R with the exception of hydrogen has the meaning given in claim 1 and

X represents halogen or acetyloxy, propionyloxy, methoxysulfonyloxy or ethoxysulfonyloxy,

if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more ner diluents.

12. compounds of the formula (II)

in which

Q, R .1, r R »2, τ R, 3, _π R4 and R have the meaning given in claim 1.

13. Agent, characterized by a content of at least one compound of formula (I) according to claim 1 and conventional extenders and / or surface-active substances.

14. A method for controlling unwanted plants, characterized in that a compound of the formula (I) according to claim 1 or an agent according to claim 13 is allowed to act on the plant and / or its habitat. j

15. Use of compounds of formula (I) according to claim 1 or agents according to claim 13 for controlling unwanted plants.