DE19822678A1 - New 1,3-diaza-2-oxo-cycloalkane derivatives, useful as pre- or post-emergence, total or selective herbicides - Google Patents

Abstract

Aryl-substituted 1,3-diaza-2-(oxo or thioxo)-cycloalkanes (I) are new. 1,3-Diaza-2-(thi)oxo-cycloalkanes of formula (I) are new. n = 1-3; Q = O or S; R1 = alkyl, alkoxy, mono- or dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl (all optionally substituted); R2 = optionally substituted, optionally heterocyclic fused mono- or bicyclic aromatic group. An Independent claim is included for the preparation of (I).

Description

The invention relates to new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes, processes for their preparation and their use as herbicides.

Some substituted 1,3-diaza-2- (thi) oxo-cycloalkanes are already from the literature known (see J. Chem. Eng. Data 13 (1968), 582-585 - cited in Chem. Abstracts 69: 106613). However, about the biological properties of these compounds nothing became known.

The new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) have now been found

in which
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ¹ represents optionally substituted alkyl, alkoxy, alkylamino, dialkyl amino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, and
R ^{2 represents} an optionally substituted, optionally heterocyclically fused, monocyclic or bicyclic aromatic group.

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

The invention preferably relates to compounds of formula (I), in which cher
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ¹ for each optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl carbonyl or C ₁ -C ₄ alkoxy carbonyl substituted alkyl, alkoxy, alkylamino, dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, each for alkenyl or alkynyl, optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy carbonyl or alkynyl, each having 2 to 6 carbon atoms, or for each optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl Cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, and
R ^{2 represents} the aromatic group defined below,

wherein
R ³ for hydrogen, nitro, amino, cyano, formylamino, halogen, or for alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, each with 1 to 6 carbon atoms in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy the alkyl groups, or for optionally by cyano; Halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl substituted cycloalkylcarbonylamino with 3 to 6 carbon atoms in the cycloalkyl part, or for optionally by cyano, nitro, C ₁ -C ₄ alkyl, C ₁ -C ₄ - Halo genalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted phenylcarbonylamino,
R ^{4 represents} hydrogen, nitro, cyano, fluorine, chlorine or bromine,
R ^{5 represents} nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, fluorine, chlorine, bromine or alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms,
R ^{6 represents} the grouping below,

-A ¹ -A ² -A ³

in which
A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C ₄ alkyl, C ₃ -C ₄ -alkenyl, C ₃ -C ₄ -alkynyl, C ₁ -C ₄ -alkoxy, phenyl, C ₁ -C ₄ -alkylcarbonyl, phenylcarbonyl, C ₁ -C ₄ -alkyl sulfonyl or phenylsulfonyl,
A ¹ furthermore for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C for each optionally substituted by fluorine, chlorine or bromine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, phenyl, C ₁ -C ₄ alkylsulfonyl or phenylsulfonyl,
A ² furthermore for C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ -azaalkenediyl, C ₂ -C ₆ -alkanediyl, C ₂ -C ₆ -alkanediyl, C ₃ -C for each optionally substituted by fluorine, chlorine or bromine _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ³ for hydrogen, hydroxy, mercapto, amino, cyano, isocyano, thio cyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, each optionally with fluorine, chlorine or C ₁ -C ₄ Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxy carbonyl or dialkoxy (thio) phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino, each optionally substituted by fluorine or chlorine, Alkylidenamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, for each optionally by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ alkyl and / or C ₁ -C ₄ alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyl oxycarbonyl or cycloalkylalkoxycarbonyl, each with 3 up to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for any given case by nitro, cyano, carboxy, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkyloxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenoxy, phenyl-C ₁ -C ₄ alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenoxycarbonyl or phenyl-C ₁ -C ₄ -alkoxycarbonyl,
A ³ further for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridrazylyl, pyridrazylyl, pyridinyl, pyridinyl, pyridinyl, pyridinyl -C ₁ -C ₄ -alkyl, furyl-C ₁ -C ₄ -alkyl, thienyl-C ₁ -C ₄ -alkyl, oxazolyl-C ₁ -C ₄ -alkyl, isoxazole-C ₁ -C ₄ -alkyl, thiazole -C ₁ -C ₄ alkyl, pyridinyl-C ₁ -C ₄ alkyl, pyrimidinyl-C ₁ -C ₄ alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, and
R ^{7 represents} hydrogen, fluorine or chlorine,
or two adjacent residues - R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ or R ⁶ and R ⁷ - together represent one of the following groups
-Q ³ -CQ ⁴ -, -Q ³ -CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -,
-Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-Q ³ -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ - ,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -,
-Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -,
-C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = NN (R ¹⁰ ) -,
-Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -
in which
Q ³ , Q ⁴ and Q ^{5 are the} same or different and each represents oxygen or sulfur,
R ⁸ and R ^{9 are the} same or different and individually represent hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl or together represent C ₂ -C ₅ alkanediyl, and
R ^{10 represents} hydrogen, hydroxy, alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxy carbonyl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or bromine, or alkynyl each having 2 to 6 carbon atoms, each optionally substituted by fluorine, chlorine, bromine or C ₁ -C ₄ alkyl Cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 atoms in the alkyl part, for alkoxy or alkenyloxy each optionally substituted by fluorine and / or chlorine, each having up to 6 carbon atoms, or for each optionally containing cyano, Fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ halo alkoxy-substituted benzyl or benzyloxy.

The invention relates in particular to compounds of the formula (I) in which
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ¹ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenyl optionally substituted by fluorine or chlorine, Butenyl, propynyl or butynyl, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, and
R ^{2 represents} the aromatic group defined below,

wherein
R ³ for hydrogen nitro, amino, cyano, formylamino, fluorine, chlorine, or for methyl, trifluoromethyl, acetylamino, propionylamino, butyroylamino, i-butyroylamino, trifluoroacetylamino, methoxy carbonylamino, ethoxycarbonylamino, methylaminocarbonylaminoaminoaminoamylaminoamylamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamylaminoamylamethylaminoaminoylamylaminoamylaminoamylaminoamylamylaminoamylaminoamylamylaminoamylaminoamylaminoamylamylaminoamylaminoamylaminoamylaminoamino stands,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
R ^{6 represents} the grouping below,

-A ¹ -A ² -A ³

in which
A ^{1 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 represents} hydrogen, hydroxy, methyl, ethyl, n- or i-propyl , Methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A ³ for hydrogen hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n - or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, dimethoxyphosphoryl, diethoxyphosphoryl or Dipropoxy phosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylidenamino, propenyloxycarbonyl, but each optionally substituted by fluorine or chlorine enyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, Cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylme thyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclo pentylidenyloxyoxycarbonyl, cycloentylyloxyoxycarbonyl, cycloentylyloxycarbonyl Cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl-substituted phenyl, phenyloxy, benzyl , Phenylethyl, benz yloxy, phenyloxy carbonyl, benzyloxycarbonyl,
A ³ furthermore for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylethylmylylylylmethyl, furyl Isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridyl methoxy, and
R ^{7 represents} hydrogen, fluorine or chlorine,
or two adjacent residues - R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ or R ⁶ and R ⁷ - together represent one of the following groups
-Q ³ -CQ ⁴ -, -Q ³ -CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -,
-Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-Q ³ -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ - ,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -,
-Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -,
-C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = NN (R ¹⁰ ) -,
-Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -
in which
Q ³ , Q ⁴ and Q ^{5 are the} same or different and each represents oxygen or sulfur,
R ⁸ and R ^{9 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R ¹⁰ for hydrogen, hydroxy, for methyl, ethyl, n- or i-propyl, n-, i-, s- or optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl t-Butyl, for propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl optionally substituted by fluorine, chlorine, bromine, methyl or ethyl , Cyclopentylmethyl or cyclohexylmethyl, for methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyl oxy or butenyloxy, each optionally substituted by fluorine and / or chlorine, or for each optionally by cyano, fluorine, Chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted benzyl or benzyloxy.

A very particularly preferred group are those compounds of formula (I) in which
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,

wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,

-A ¹ -A ² -A ³

in which
A ^{1 represents} a single bond,
A ^{2 represents} a single bond,
A ³ for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy -, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-prop oxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethyl sulfonyl , n- or i-Propylsulfonyl, methylamino, ethylamino, n- or i-propyl amino, n-, i-, s- or t-butylamino, dimethylamino, diethyl amino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for in each case optionally substituted by fluorine or chlorine, propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenyl amino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butinyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propiny loxycarbonyl or butynyloxy carbonyl, for in each case optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexyl , Cyclohexyloxycarbonyl, Cyclopentylmethoxycarbonyl or Cyclohe xylmethoxycarbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy , Trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenoxy, benzyloxy, phenyloxycarbonyl or benzyloxy carbonyl, and
R ^{7 represents} hydrogen.

Another very particularly preferred group are those compounds of formula (I) in which
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,

wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,

-A ¹ -A ² -A ³

in which
A ^{1 stands} for the grouping -NA ⁴ -, wherein A ^{4 stands} for hydrogen, methyl sulfonyl or ethylsulfonyl,
A ^{2 represents} a single bond or -CO-,
A ³ for hydrogen, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- substituted by fluorine, chlorine, methoxy or ethoxy Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl , for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopro pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropyl methyl, cyclobutylmethyl , Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or eth oxycarbonyl substituted phenyl, phenoxy, benzyl or benzyloxy, and
R ^{7 represents} hydrogen.

Another very particularly preferred group are those compounds of formula (I) in which
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,

wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,

-A ¹ -A ² -A ³

in which
A ^{1 stands} for the grouping -NA ⁴ -, wherein A ^{4 stands} for hydrogen, methyl sulfonyl or ethylsulfonyl,
A ^{2 stands} for -SO ₂ -,
A ³ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine, chlorine, cyano or methyl ized cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for phenyl or benzyl which is optionally substituted in each case by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl, and
R ^{7 represents} hydrogen.

The general or priority areas listed above Definitions apply both to the end products of formula (I) and accordingly to the raw materials or intermediate products required for the production. This Residual definitions can be among themselves, that is, between the specified Be range of preferred connections, can be combined as desired.

The new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) are characterized by strong and selective herbicidal activity.

The new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) are obtained if
1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (II)

in which
n, Q and R ^{1 have} the meaning given above,
with halogen compounds of the general formula (III)

X ¹ -R ² (III)

in which
R ^{2 has} the meaning given above and
X ^{1 represents} halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carry out electrophilic or nucleophilic substitution reactions as part of the substituent definition in the customary manner.

In principle, the compounds of the general formula (I) can also be synthesized as shown schematically in the following:
Reaction of diamines of the general formula (IV) with (thio) carbonic acid derivatives of the general formula (V)

in which
n, Q, R ¹ and R ^{2 have} the meaning given above and
Y ¹ and Y ^{2 are} identical or different and each represents halogen (in particular chlorine), alkoxy (in particular methoxy or ethoxy), alkoxyalkoxy (in particular special (methoxyethoxy or ethoxyethoxy), phenoxy or imidazolyl,
optionally in the presence of a reaction auxiliary, such as. B. pyridine and optionally in the presence of a diluent, such as. B. toluene.

Reaction of 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (VI) with halogen compounds of the general formula (VII)

in which
n, Q, R ¹ and R ^{2 have} the meaning given above and
X ^{2 represents} halogen (in particular chlorine, bromine or iodine),
optionally in the presence of a reaction auxiliary such as. B. ethyl diisopropyl amine, and optionally in the presence of a diluent such as. B. Aceto nitrile.

Reaction of (thio) ureas of the general formula (VIII) with α, ω-disubstituted alkanes of the general formula (IX)

in which
n, Q, R ¹ and R ^{2 have} the meanings given above and
E ¹ and E ^{2 represent} nucleophilically substitutable leaving groups, such as halogen (in particular chlorine or bromine or alkylsulfonyloxy (in particular methylsulfonyloxy),
optionally in the presence of a reaction auxiliary such as. As potassium carbonate, and optionally in the presence of a diluent such as. B. acetone.

If, for example, 1-methyl-imidazolidin-2-one and 2,4,5-trifluorobenzonitrile are used as starting materials, 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 1,3-diaza-2- (thi) oxo-cycloalkanes to be used as starting materials in the process according to the invention for the preparation of compounds of formula (I). In the formula (II), n, Q and R ¹ have preferably or in particular those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention, preferably or as particularly preferred for n, Q and R ^{1 were} specified.

The starting materials of the general formula (II) are known and / or can be according to known processes can be prepared (cf. J. Am. Chem. Soc. 80 (1958), 6409-6412; J. Chem. Soc. Perkin Trans. 1, 1981, 2499-2503; J. Org. Chem. 22 (1957), 1581; J. Org. Chem. 28: 7339-7342 (1992); Synth. Commun. 27 (1997), 3565-3571).

The halogen compounds to be used further as starting materials in the process according to the invention are generally defined by the formula (III). In the formula (III), R ² preferably or in particular has the meaning which has already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention preferably or as particularly preferred for R ² ; X ² preferably represents fluorine or chlorine, in particular fluorine.

The starting materials of the general formula (III) are known and / or can be according to processes known per se (cf. EP-A-191181, EP-A-370332, EP-A-431373, EP-A-441004, EP-A-597360).

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably carried out using a diluent guided. Inert organic solutions are the main diluents medium into consideration. These include in particular aliphatic, alicyclic or aroma tables, optionally halogenated hydrocarbons, such as gasoline, Benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, Dichloromethane, chloroform, carbon tetrachloride, ethers such as diethyl ether, diiso propyl 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-dimethyl acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorus acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide.  

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably carried out using a reaction aid guided. The usual anor are generally used as reaction aids ganic or organic bases or acid acceptors. This includes preferably alkali metal or alkaline earth metal, acetates, amides, carbonates, -hydrogen carbonates, -hydrides, -hydroxides or -alkanolates, such as 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, methanol, -ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basi organic nitrogen compounds such as trimethylamine, triethyl amine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexyl amine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-Di methyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-di methyl-, 3,4-dimethyl- and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-di methylamino-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 reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 150 ° C, preferably between 20 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure leads. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar to lead.

To carry out the process according to the invention, the starting materials in generally used in approximately equimolar amounts. However, it is also possible Lich to use one of the components in a larger excess. The order  settlement is generally in a suitable diluent in the presence carried out a reaction auxiliary and the reaction mixture is generally NEN stirred for several hours at the required temperature. The workup is carried out according to customary methods (cf. the production examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. used in the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abuti lon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum.
Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera.
Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to these Genres limited, but extends in the same way to other plants Zen.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and squares with and without tree cover. Likewise, the connections to weed control fungus in permanent crops, e.g. B. forest, ornamental wood, fruit, wine, citrus, nut, bana nen-, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pastures and for selective weed control in annual cultures are used.

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocotyledon and dicotyledon weeds in monocotyledons Cultures both pre-emergence and post-emergence.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, sol Liche powder, granules, suspension emulsion concentrates, impregnated with active ingredient Natural and synthetic substances as well as very fine encapsulation in polymeric substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid carriers gerstoffe, optionally using surfactants, so Emulsifiers and / or dispersants and / or foaming agents.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkylnaphtha  line, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorine benzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as Cyclohexane or paraffins, e.g. B. 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 solution medium, such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, come as solid carriers for granules in question: e.g. B. broken and fractionated natural rocks such as calcite, marble, Pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules made from organic material such as sawdust, coconut husks, corn cobs and tobacco stems; as emulsifier and / or foam generator Funds are possible: B. non-ionic and anionic emulsifiers, such as poly oxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl poly glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as Dispersants come into question: z. B. lignin sulfite and methyl cellulose.

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

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine substances 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example
Acetochlor, Acifluorfen (-sodium), Aclonifen, Alachlor, Alloxydim (-sodium), Ame tryne, Antidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl) Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromo fenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chloromethoxyid, Chloromethoxyid , Chlorimuron (-ethyl), Chloronitrofen, Chlorsulfuron, Chlortoluron, Cinmethylin, Cino sulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulazine (Cyclomethyl), Cumyl Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, Desmedi pham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzo quat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimetha metryn, dimethenamid, dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Di uron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop - (- P-ethyl), Flamprop (-isoprop Flamprop (-isopropyl-L), Flamprop (-methyl), Flazasulf uron, Florasulam, Fluazifop (-P-butyl), Flumetsulam, Flumiclorac (-pentyl), Flumiox azine, Flumipropyn, Flumetsulam, Fluometuron, Fluorochloridone-Fluoroglyofen ), Flupoxam, Flupropacil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium) Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imaza methabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynouronuron, Isoxynilonuron, Isoxynilonuron, Isoxynilroton , Isoxaben, Isoxaflutole, Is oxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitr on; Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metola chlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolin uron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazonz, Orbencarb Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Para quat, Pelargonic Acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pre tilachlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyarbonethyl, Prosulfuron, Prosulfuron, Prosulfur Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyrimino bac (-methyl), Pyrithiobac (-sodium), Quinchlorac, Quinmerac, Quinoclamine, Quizalo fop (-P-ethyl), Quizalofuryl (-P-t- ), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thia zopyr, Thidiazimin sulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin and triflusulfuron.

Also a mixture with other known active ingredients, such as fungicides, insecticides den, acaricides, nematicides, bird repellants, plant nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used the. The application is done in the usual way, e.g. B. by pouring, spraying, spraying hen, scatter.

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

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

The manufacture and use of the active compounds according to the invention are based on following examples.

Manufacturing examples

example 1

A mixture of 5.8 g (50 mmol) of 1-methylimidazolidin-2-thione, 8.6 g (55 mmol) 2,4,5-trifluoro-benzonitrile, 7.6 g (55 mmol) of potassium carbonate and 50 ml of dimethyl sulfoxide is stirred at 80 ° C for 16 hours. After cooling, the mixture is under Stir in a mixture of approximately equal volumes of methylene chloride and Poured water and acidified with 2N hydrochloric acid. The organic phase is removed separates, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diethyl ether and the crystalline product is isolated by suction.

9.5 g (75% of theory) of 1-methyl-3- (4-cyano-2,5-difluorophenyl) imida are obtained zolidin-2-thione with a melting point of 143 ° C.

Example 2

(Follow-up implementation)

A mixture of 2.0 g (8 mmol) of 1-methyl-3- (4-cyano-2,5-difluorophenyl) imida zolidln-2-thione, 1.8 g (16 mmol) ethanesulfonic acid amide, 2.2 g (16 mmol) potassium carbonate and 50 ml of dimethyl sulfoxide is stirred at 100 ° C for 16 hours. After The mixture is cooled while stirring into a mixture of approximately the same volume Quantities of methylene chloride and water poured and acidified with 2N hydrochloric acid. The organic phase is separated off, washed with water and ge with sodium sulfate dries and filtered. The filtrate is concentrated in a water jet vacuum, the back stood digested with isopropanol and the crystalline product obtained by suction isolated.

1.9 g (68% of theory) of 1-methyl-3- (4-cyano-2-fluoro-5-ethylsulfonyl) are obtained aminophenyl) imidazolidin-2-thione with a melting point of 174 ° C.

Analogously to the preparation examples 1 to 2 and in accordance with the general description of the preparation process according to the invention, for example the compounds of the formula (I) listed in Table 1 below can also be prepared.

Table 1

Examples of the compounds of the formula (I)

Examples of use Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether.

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours the soil is sprayed with the active ingredient preparation so that the respective desired amounts of active ingredient are applied per unit area. The Concentration of the spray liquor is chosen so that each in 1000 l of water / ha 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 annihilation.

In this test, for example, the compounds according to Preparation Example 2 show 5, 8, 9, 10, 11 and 12 with partially good tolerance to crops, such as B. corn, 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, mix 1 Part by weight of active ingredient with the specified amount of solvent, gives the specified the same amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l of 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 annihilation.

In this test, for example, the compounds according to Preparation Example 2 show 8, 9, 10 and 12 with good tolerance to crops, such as. B. Barley, strong action against weeds.

Claims (9)

1. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I)
in which
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ^{1 represents} in each case optionally substituted alkyl, alkoxy, alkylamino, di alkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, and
R ^{2 represents} an optionally substituted, optionally heterocyclically fused, monocyclic or bicyclic aromatic group. 2. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ¹ for each optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl carbonyl or C ₁ -C ₄ alkoxy carbonyl substituted alkyl, alkoxy, alkylamino, dialkylamino each having 1 to 6 carbon atoms in the alkyl groups, represents in each case optionally cyano-, halogen or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkenyl or alkinyl each having 2 to 6 carbon atoms, or represents in each case, where appropriate by cyano, halogen or C ₁ -C ₄ alkyl substituted cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, and
R ^{2 represents} the aromatic group defined below,
wherein
R ³ for hydrogen, nitro, amino, cyano, formylamino, halogen, or for alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, each with 1 to 6 carbon atoms in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy the alkyl groups, or for cycloalkylcarbonylamino with 3 to 6 carbon atoms in the cycloalkyl part which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ haloalkyl, or for optionally by cyano, nitro, C ₁ -C ₄ -Alkyl, C ₁ -C ₄ -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy-substituted phenylcarbonylamino,
R ^{4 represents} hydrogen, nitro, cyano, fluorine, chlorine or bromine,
R ^{5 represents} nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, hydroxy, fluorine, chlorine, bromine or alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms,
R ^{6 represents} the grouping below,
-A ¹ -A ² -A ³
in which
A ^{1 stands} for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for What serstoff, hydroxy, C ₁ -C ₄ alkyl, C ₃ -C ₄ alkenyl, C ₃ -C ₄ alkynyl, C ₁ -C ₄ alkoxy, phenyl, C ₁ -C ₄ alkylcarbonyl, phenyl carbonyl, C ₁ -C ₄ alkylsulfonyl or phenylsulfonyl ,
A ¹ furthermore represents in each case optionally substituted by fluorine, chlorine or bromine-substituted C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ aza alkenediyl, C ₂ -C ₆ alkynediyl, C ₃ -C _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ^{2 stands} for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for What serstoff, hydroxy, C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, phenyl, C ₁ -C ₄ alkyl sulfonyl or phenylsulfonyl,
A ² furthermore represents in each case optionally substituted by fluorine, chlorine or bromine, C ₁ -C ₆ -alkanediyl, C ₂ -C ₆ -alkenediyl, C ₂ -C ₆ aza alkenediyl, C ₂ -C ₆ alkynediyl, C ₃ -C _6- cycloalkanediyl, C ₃ -C ₆ -cycloalkenediyl or phenylene,
A ³ for hydrogen, hydroxyl, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for each case where appropriate by fluorine, chlorine or C ₁ -C ₄ - Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkyl amino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) - phosphoryl each having 1 to 6 carbon atoms in the alkyl groups, for alkenyl, alkenyloxy, alkenylamino optionally substituted by fluorine or chlorine , Alkylidene amino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, for each optionally by fluorine, chlorine, cyano, carboxy, C ₁ -C ₄ alkyl and / or C ₁ -C ₄ alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalky lidenamino, cycloalkyloxycarbonyl or cycloalkylalkoxy carbonyl with each 3 to 6 carbon atoms in the cycloal kylgruppen and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C ₁ -C ₄ alkyl, C ₁ -C ₄ halogen alkyl, C ₁ -C ₄ alkyloxy, C ₁ -C ₄ haloalkyloxy and / or C ₁ -C ₄ alkoxycarbonyl substituted phenyl, phenoxy, phenyl-C ₁ -C ₄ -alkyl, phenyl-C ₁ -C ₄ -alkoxy, phenoxycarbonyl or phenyl-C ₁ -C ₄ -alkoxycarbonyl,
A ³ furthermore for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyridinyl, pyridinyl, pyriminyl, pyridinyl, pyriminyl C ₁ -C ₄ alkyl, furyl C ₁ -C ₄ alkyl, thienyl C ₁ -C ₄ alkyl, oxazolyl C ₁ -C ₄ alkyl, isoxazole C ₁ -C ₄ alkyl, thiazole C ₁ -C ₄ alkyl, pyridinyl-C ₁ -C ₄ alkyl, pyrimidinyl-C ₁ -C ₄ alkyl, pyrazolylmethoxy, furylmethoxy, represents perhydropyranylmethoxy or pyridylmethoxy, and
R ^{7 represents} hydrogen, fluorine or chlorine,
or two adjacent radicals - R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ or R ⁶ and R ⁷ - together represent one of the following groups
-Q ³ -CQ ⁴ -, -Q ³ -CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -,
-Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -C (R ⁵ , R ⁹ ) -CQ ⁴ -,
-Q ³ -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ - ,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -,
-Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -,
-C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = NN (R ¹⁰ ) -,
-Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -
in which
Q ³ , Q ⁴ and Q ^{5 are the} same or different and each represents oxygen or sulfur,
R ⁸ and R ^{9 are the} same or different and are individually hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ alkyl or together are C ₂ -C ₅ alkanediyl, and
R ¹⁰ for hydrogen, hydroxy, for alkyl, alkylcarbonyl, alkoxycarbonyl or optionally substituted by cyano, fluorine, chlorine, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ alkoxycarbonyl Alkylsulfonyl, each with 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or bromine, or alkynyl, each with 2 to 6 carbon atoms, for each optionally by fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl substituted cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and, if appropriate, 1 to 3 atoms in the alkyl part, for alkoxy or alkenyloxy, each optionally substituted by fluorine and / or chlorine, each having up to 6 carbon atoms, or for each, if appropriate alkyl substituted by cyano, fluorine, chlorine, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halo, C ₁ -C ₄ alkoxy or C ₁ -C ₄ -haloalkoxy sub stituiertes benzyl, or benzyloxy. 3. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that
n represents 1, 2 or 3,
Q represents oxygen or sulfur,
R ¹ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for propenyl optionally substituted by fluorine or chlorine, Butenyl, propynyl or butynyl, or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, and
R ^{2 represents} the aromatic group defined below,
wherein
R ³ represents hydrogen, nitro, amino, cyano, formylamino, fluorine, chlorine, or represents methyl, trifluoromethyl, acetylamino, propio nylamino, butyroylamino, i-butyroylamino, trifluoroacetyl amino, methoxycarbonylamino, ethoxycarbonylamino, methyl aminocarbonylamino, ethylaminocarbonylamino, cyclopropyl carbonylamino or phenylcarbonylamino (Benzoylamino) stands,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,
R ^{6 represents} the grouping below,
-A ¹ -A ² -A ³
in which
A ^{1 stands} for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, where A ^{4 stands} for hydrogen, hydroxy, methyl, ethyl, n- or i- Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,
A ¹ furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propen-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A ^{2 stands} for a single bond, for oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for hydrogen, hydroxy, methyl, ethyl, n- or i- Propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,
A ² furthermore for methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane-1,3-diyl, ethene-1, 2-diyl, propen-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-1,3-diyl,
A ³ for hydrogen, hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n- or in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy , i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n- , i-, s- or t-pentyloxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, Ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethyl amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, Dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxy phosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidenamino, butylidene amino, propenyloxycarbonyl, each optionally substituted by fluorine or chlorine, Butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for each cyclopropyl, cyclobutyl, optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxy carbonyl , Cyclopentyl, Cyclohexyl, Cyclopropyloxy, Cyclobutyloxy, Cyclopentyloxy, Cyclohexyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclo pentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclo butylmethoxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylylyloxyoxyoxy, Cyclopentylyloxyoxyoxy, Cyclo Pentylylyloxyoxyoxy, Cyclopentylyloxyoxyoxy, Cyclo Pentylyloxy Methyloxy, Cyclo Pentylyloxy Methyloxy Cyclo Nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxy carbonyl and / or ethoxycarbonyl substituted phenyl, phenyloxy , Benzyl, phenylethyl , Benzyloxy, phenyloxy carbonyl, benzyloxycarbonyl,
A ³ furthermore for (in each case wholly or partly hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylylyl, furyl Oxazolylmethyl, isoxazole methyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, and
R ^{7 represents} hydrogen, fluorine or chlorine,
or two adjacent radicals - R ³ and R ⁴ , R ⁴ and R ⁵ , R ⁵ and R ⁶ or R ⁶ and R ⁷ - together represent one of the following groups
-Q ³ -CQ ⁴ -, -Q ³ -CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -,
-Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -,
-Q ³ -C (R ⁸ ) = C (R ⁸ ) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -, -Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ - ,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -,
-Q ³ -CQ ⁴ -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -,
-C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -,
-C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -,
-N (R ¹⁰ ) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = NN (R ¹⁰ ) -,
-Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R ¹⁰ ) -
in which
Q ³ , Q ⁴ and Q ^{5 are the} same or different and each represents oxygen or sulfur,
R ⁸ and R ^{9 are the} same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and
R ¹⁰ for hydrogen, hydroxy, for methyl, ethyl, n- or i-propyl, n-, i-, s or optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxy carbonyl or ethoxycarbonyl t-Butyl, for propenyl, butenyl, propynyl or butynyl, each optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl Cyclohexylmethyl, for methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each optionally substituted by fluorine and / or chlorine, or, if appropriate, in each case by cyano, fluorine, chlorine, Methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromoxy substituted benzyl or benzyloxy. 4. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,
wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,
-A ¹ -A ² -A ³
in which
A ^{1 represents} a single bond,
A ^{2 represents} a single bond,
A ³ for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, for methyl, ethyl, n- or i-propyl, n-, i-, which is optionally substituted by fluorine, chlorine, methoxy or ethoxy -, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, n-, i -, s- or t-pentyloxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n - or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethyl amino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, each for optionally by Fluorine or chlorine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxyca rbonyl or butynyloxycarbonyl, for cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethoxy, cyclobutyl methoxy, cyclopentylmethoxy, cyclohexylmethoxy, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl Cyclopen tyloxycarbonyl, cyclohexyloxycarbonyl, cyclopentylmethoxy carbonyl or cyclohexylmethoxycarbonyl, or for each ge optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenoxy, benzyloxy, phenyloxycarbonyl or benzyloxy carbonyl, and
R ^{7 represents} hydrogen. 5. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,
wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,
-A ¹ -A ² -A ³
in which
A ^{1 stands} for the grouping -NA ⁴ -, in which A ^{4 stands} for hydrogen, methylsulfonyl or ethylsulfonyl,
A ^{2 represents} a single bond or -CO-,
A ³ for hydrogen for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-prop each optionally substituted by fluorine, chlorine, methoxy or ethoxy oxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propyl thio, n-, i-, s- or t-butylthio, methylsulfonyl, ethyl sulfonyl, n- or i- Propylsulfonyl, for each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopro pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclo propylmethyl, cyclo propylmethyl , Cyclopentylmethyl, Cyclohe xylmethyl, Cyclopropylmethoxy, Cyclobutylmethoxy, Cyclo pentylmethoxy, Cyclohexylmethoxy, or for each where appropriate by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or Ethoxycarbonyl substituted phenyl, phenoxy, benzyl or benzyloxy, and
R ^{7 represents} hydrogen. 6. Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that
n represents 1 or 2,
Q represents oxygen or sulfur,
R ^{1 represents} in each case methyl, ethyl, n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, and
R ^{2 represents} the aromatic group defined below,
wherein
R ^{3 represents} hydrogen, fluorine or chlorine,
R ^{4 represents} hydrogen,
R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,
R ^{6 represents} the grouping below,
-A ¹ -A ² -A ³
in which
A ^{1 stands} for the grouping -NA ⁴ -, in which A ^{4 stands} for hydrogen, methylsulfonyl or ethylsulfonyl,
A ^{2 stands} for -SO ₂ -,
A ³ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl optionally substituted by fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by fluorine, chlorine, cyano or methyl Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl, and
R ^{7 represents} hydrogen. 7. A process for the preparation of substituted 1,3-diaza-2- (thi) oxo-cycloal kanen according to one of claims 1 to 6, characterized in that
1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (II)
in which
n, Q and R ^{1 have} the meaning given in one of claims 1 to 6,
with halogen compounds of the general formula (III)
X ¹ -R ² (III)
in which
R ^{2 has} the meaning given in one of claims 1 to 6 and
X ^{1 represents} halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent and if appropriate subsequently carrying out electrophilic or nucleophilic substitution reactions as part of the substituent definition in the customary manner. 8. Herbicidal agent, characterized by the content of at least one Substituted 1,3-diaza-2- (thi) oxo-cycloalkane according to one of claims 1 until 6. 9. Use of at least one substituted 1,3-diaza-2- (thi) oxo cycloalkane according to one of claims 1 to 6 for combating imm wanted plants.