EP1080077A1

EP1080077A1 - Substituted 1,3-diaza-2-(thi)oxo-cycloalkanes

Info

Publication number: EP1080077A1
Application number: EP99952091A
Authority: EP
Inventors: Klaus Helmut MÜLLER; Markus Dollinger; Mark Wilhelm Drewes; Ingo Wetcholowsky; Randy Allen Myers
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1998-05-20
Filing date: 1999-05-18
Publication date: 2001-03-07
Also published as: CA2332443A1; DE19822678A1; WO1999059977A1; AU4263999A; JP2002515492A; BR9910610A; CN1301257A; KR20010043505A

Abstract

The invention relates to new substituted 1,3-diaza-2-(thi)oxo-cycloalkanes of general formula (I), in which n is 1, 2 or 3, Q is oxygen or sulphur, R1 is alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl or cycloalkylalkyl, whereby each of these groups is possibly substituted, and R2 is a monocyclic or bicyclic aromatic grouping which is possibly substituted and possibly heterocyclically anellated. The invention also relates to a method for producing these compounds and to their use as herbicides.

Description

Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes

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 known from the literature (cf. J. Chem. Eng. Data 13 (1968), 582-585 - cited in Chem. Abstracts 69: 106613) . However, nothing is known about the biological properties of these compounds.

The new substituted 1,3-diaza-2- (thi) oxocycloalkanes 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 hydrogen, formyl or optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, and

R2 represents an optionally substituted, optionally heterocyclically fused, monocyclic or bicyclic aromatic group. In the definitions, the hydrocarbon chains, such as alkyl, are also straight-chain or branched, in each case in conjunction with heteroatoms, such as in alkoxy.

n is preferably 1, 2 or 3;

Q preferably represents oxygen or sulfur;

Rl preferably represents hydrogen, formyl or for alkyl, alkoxy, alkylamino, dialkylamino, each substituted by cyano, halogen, C1-C4-alkoxy, C 1 -C 4 -alkylcarbonyl, C [-C4-alkoxycarbonyl or morpholinyl 1 to 6 carbon atoms in the alkyl groups, for alkenyl or alkynyl, each optionally substituted by cyano, halogen or C 1 -C 4 -alkoxycarbonyl, or 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;

R ² preferably represents the aromatic group defined below

wherein

R3 for hydrogen, nitro, amino, cyano, formylamino, halogen, or for each optionally by cyano, halogen or Cj-C4-alkoxy substituted alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino each having 1 to 6 carbon atoms in the alkyl groups, or for cycloalkylcarbonylamino having 3 to 6 carbon atoms optionally substituted by cyano, halogen, Cj-C4-A_kyl or Cj-C4-haloalkyl in the cycloalkyl part, or phenylcarbonylamino which is optionally substituted by cyano, nitro, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 halooxy;

R ^ represents hydrogen, nitro, cyano, fluorine, chlorine or bromine;

R5 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;

R6 represents the grouping below:

-Ai-A ^ A ³

in which

A represents a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ^ -, where A ^ represents hydrogen, hydroxy, C1-C4-alkyl, C3-C4-alkenyl, C3-C -alkynyl, C1-C4-

Alkoxy, phenyl, -C-C4-alkyl-carbonyl, phenylcarbonyl, C1-C4-alkyl-sulfonyl or phenylsulfonyl,

A ^ furthermore for Cj-Cö-alkanediyl, C2-C6-alkenediyl, C2-C6-azaalkenes which are optionally substituted by fluorine, chlorine or bromine is diyl, C2-Cö-alkindiyl, Cß-Cö-cycloalkanediyl, C3-C6-cycloalkendiyl or phenylene,

A ^{2 represents} a single bond, represents oxygen, sulfur, -SO-, -SO2-, -CO- or the group -NA ^ -, where A ^ represents hydrogen,

Is hydroxy, C1-C4-alkyl, Cj ^ -alkoxy, phenyl, C _] -C4-alkylsulfonyl or phenylsulfonyl,

A ² furthermore for C 1 -Cg-alkanediyl, C2-C6-alkenediyl, C2-Cg-azaalkenediyl, C2-Cö-alkynediyl, C3-C6-alkynediyl, C3-C6-cycloalkanediyl, C3-C6-, C3-C6- Cycloalkenediyl or phenylene,

A ³ for hydrogen, hydroxy, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, chlorine, bromine, each optionally with fluorine, chlorine or C1-C4 - Alkoxy substituted alkyl, alkoxy, alkylthio, alkylsulfmyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) phosphoryl, each with 1 to 6 carbon atoms in the alkyl groups, each for optionally by

Fluorine or chlorine-substituted alkenyl, alkenyloxy, alkenylamino, alkylidene amino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally by fluorine, chlorine, cyano , Carboxy, -C-C4-alkyl and / or C \ -C4-alkoxy-carbonyl substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl groups, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, C - C4- alkyl, -C-C4-haloalkyl, C \ -C4-alkyloxy, Cι-C4-haloalkyloxy and / or Cι-C4-alkoxy-carbonyl substituted phenyl, phenoxy, phenyl-Cι-C4-alkyl, phenyl-Cι -C4-alkoxy, phenoxy-carbonyl or phenyl -CC-C4-alkoxycarbonyl,

A ³ continues for (in some cases fully or partially hydrogenated)

Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl,

Dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl,

Oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl -CC-C -alkyl, furyl -CC-C4-alkyl, thienyl -CC-C ₄ -alkyl, oxazolyl-

-C-C4-alkyl, isoxazole-C [-C4-alkyl, thiazole-C -C4-alkyl, pyridinyl-Cι-C4-alkyl, pyrimidinyl-Cι-C4-alkyl, pyrazolylmethoxy, furyl methoxy, for perhydropyranylmethoxy or pyridylmethoxy ,

R ^ represents hydrogen, fluorine or chlorine,

or two adjacent residues - R ³ and R4, R4 and R ^, R ^ and R ^ or R ^ and R ^ - together represent one of the following groups

-Q ³ -CQ ⁴ -, -Q3-CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R ⁸ , R9) -CQ ⁴ -,

-C (R ⁸ , R9) -Q -CQ -, -Q ³ -C (R ⁸ , R9) -C (R8, R9) -,

-Q ³ -C (R8, R9) -C (R ⁸ , R ⁹ ) -Q ⁵ -, -C (R8, R9) .C (R8, R9) -CQ4.,

-Q ³ -C (R) = C (R ⁸ ) -, -C (R8) = C (R8) -CQ4-, -Q -C (R, R ⁹ ) -CQ ⁴ -,

-N (R10) -C (R ⁸ ; R9) -CQ -, -C (R) = N-, -Q -CQ ⁴ -C (R ⁸ , R ⁹ ) -, -Q ³ -CQ4-N ( R ¹⁰ ) -, -Q ³ -C (R ⁸ , R9) -CQ4-N (RlO) -,

-C (R ⁸ , R9) -Q ³ -CQ4-N (R ¹ 0) -, -C (R8, R9) -C (R8, R9) .N (Rl0) -,

-C (R8, R9) .C (R8, R9) -CQ4-N (R ¹ 0) -, -C (R ⁸ ) = C (R8) -N (R ¹ 0) -,

-C (R ⁸ ) = C (R ⁸ ) -CQ4-N (R ¹ 0) -, -C (R8, R9) .CQ4.N (R1 °) -,

-N (R ¹⁰⁾ -C (R ^8; R 9) -CQ4-N (R ¹ 0) -, -C (R) = NN (R10) -, -Q ³ -CQ ⁴ -C (R ^8, R 9 ) -N (R ¹⁰ ) -, Q ³ -C (R ⁸ , R9) -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 are identical or different and individually represent hydrogen, fluorine, chlorine, bromine or C1-C4-alkyl or together represent C2-C5-alkanediyl, and

R ¹⁰ for hydrogen, hydroxy, for optionally by cyano, fluorine, chlorine, C -

C4-Alkoxy, Cι-C4-alkyl-carbonyl or C 1 -C4-alkoxy-carbonyl substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for each optionally substituted by fluorine, chlorine or bromine or Alkynyl each having 2 to 6 carbon atoms, each optionally by fluorine, chlorine,

Bromine or C1-C4-alkyl substituted 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 by cyano, fluorine,

Chlorine, C 1 -C 4 -alkyl, C 1 -C 4 -haloalkyl, C 1 -C 4 -alkoxy or C 1 -C -haloalkoxy substituted benzyl or benzyloxy.

n particularly preferably represents 1, 2 or 3;

Q particularly preferably represents oxygen or sulfur;

Rl particularly preferably represents hydrogen, formyl or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, each optionally propenyl, butenyl, propynyl or substituted by fluorine or chlorine Butinyl, or for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl or cyclohexylmethyl or cyclohexylmethyl, which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl;

R ³ preferably stands for hydrogen, nitro, amino, cyano, formylamino, fluorine, chlorine, or for methyl, trifluoromethyl, acetylamino, propionylamino, butyroylamino, i-butyroylamino, trifluoroacetylamino, methoxycarbonylamino, ethoxycarbonylamino, methylaminocarbonocylylylylyl, ethylaminoaminocarbonylamyl, ethylaminoaminocarbonylamyl, ethylaminoamino carbonylamylcarbonyl or phenylcarbonylamino (benzoylamino);

R preferably represents hydrogen, fluorine or chlorine;

R5 preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

R6 particularly preferably stands for the following grouping:

-Ai-A ² ^ ³

in which

Al stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁴ -, in which A4 stands for hydrogen,

Hydroxyl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,

A ^ furthermore for methylene, ethane-l, l-diyl, ethane-l, 2-diyl, propane-1,1-diyl, propane-l, 2-diyl, propane-l, 3-diyl, ethene-l, 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-, -SO2-, -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 also 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 ^J for hydrogen, hydroxy, amino, cyano, nitro, carboxy,

Carbamoyl, sulfo, fluorine, chlorine, bromine, for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i- optionally substituted by fluorine, chlorine, methoxy or ethoxy -, 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, methylsulfmyl, ethylsulfonyl, 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-propoxycarbonyl, dimethoxyphosphoryl,

Diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphoryl, for propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, propynyl, propynyl, propenyloxycarbonyl

Butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or Butynyloxycarbonyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclopentylmethyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutylmeth- oxy, Cyclopentylmethoxy, Cyclohexylmethoxy, Cyclopentylidenamino, Cyclohexylidenamino, Cyclopentyloxycarbonyl, Cyclohexyloxycarbonyl, Cyclopentylmethoxycarbonyl or Cyclohexyl or Cyoxy, optionally through, Nitro

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, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,

A ³ continues for (in some cases fully or partially hydrogenated)

Pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl,

Isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrylmethoxymethyl, pyylmethoxy, pyrylmethoxy, pyrylmethoxy, pyryl methoxy, pyryl methoxy, pyryl methoxy, pyryl methoxy, pyryl methoxy, furyl

R ^ preferably represents hydrogen, fluorine or chlorine.

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 preferably represent one of the following groups:

-Q ³ -CQ ⁴ -, -Q3-CQ ⁴ -Q ⁵ -, -Q ³ -C (R ⁸ , R9) -Q ⁵ -, -C (R ⁸ , R9) -CQ ⁴ -,

-C (R ⁸ , R9) -Q ³ -CQ ⁴ -, -Q ³ -C (R, R9) -C (R ⁸ , R9) -, -Q ³ -C (R ⁸ , R9) -C (R ⁸ , R9) -Q5-, -C (R, R9) -C (R, R9) -CQ ⁴ -, -Q ³ -C (R) = C (R ⁸ ) -, -C (R) = C (R) -CQ ⁴ -, -Q ³ -C (R ⁸ , R9) -CQ ⁴ -, -N (R ¹ 0) -C (R ; R9) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R9) -, -Q ³ -CQ ⁴ -N (Rl ⁰ ) -, -Q ³ -C (R, R9) -CQ ⁴ -N (Rl0) -, -C (R ⁸ , R9) -Q ³ -CQ ⁴ -N (R1 °) -, -C (R, R9) -C ( R, R ⁹ ) -N (R10) -, -C (R ⁸ , R9) -C (R ⁸ , R ⁹ ) -CQ ⁴ -N (R10) -, -C (R) = C (R) - N (R10) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R1 °) -, -C (R, R9) -CQ ⁴ -N (R10) -, -N (R ! 0) -C (R ⁸ ; R ⁹ ) -CQ ⁴ -N (R ¹ 0) -, -C (R ⁸ ) = NN (R! °) -, -Q -CQ ⁴ -C (R ⁸ , R9) -N (Rl °) -, Q ³ -C (R ⁸ , R9) -C (R ⁸ , R9) -CQ ⁴ -N (Rl 0) -

in which

Q ³ , Q ⁴ and Q ^ are the same or different and each represents oxygen or sulfur,

R ⁸ and R9 are the same or different and individually represent hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene), and

RIO for hydrogen, hydroxy, for optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, for propenyl, butene, which are optionally substituted by fluorine, chlorine or bromine - nyl, propynyl or butynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, for methoxy optionally substituted by fluorine and / or chlorine , Ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, or for each optionally by cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted benzyl or benzyloxy; n very particularly preferably represents 1 or 2;

Q very particularly preferably represents oxygen or sulfur;

Rl very particularly preferably represents methyl, ethyl, n- or i-propyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;

R ³ particularly preferably represents hydrogen, fluorine or chlorine;

R ⁴ particularly preferably represents hydrogen;

R5 particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl;

R "particularly preferably stands for the following grouping:

-A! -A ² -A ³

in which

A ^ represents a single bond,

A ^{2 represents} a single bond,

A ³ for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo,

Fluorine, chlorine, bromine, each optionally by fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i-

Propoxy, n-, i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methyl thio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfmyl, 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-propoxycarbonyl, for propenyl or butenyl, each optionally substituted by fluorine or chlorine , Propenyloxy, butenyloxy, propenylamino, butenylamino, propylidene amino, butylidene amino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or

Butynyloxycarbonyl, for each cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylmethoxy, cyclohexyl methoxy, cyclopentyl methoxy, cycloentyl methoxy, cyclohexyl methoxy , Cyclohexyloxycarbonyl, Cyclopentylmethoxycarbonyl or Cyclohexylmethoxycarbonyl, or for each optionally by nitro, cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro- methoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl substituted phenoxy, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl;

R ⁷ particularly preferably represents hydrogen.

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 there is a combination of the meanings listed above as being particularly preferred.

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,

woπn

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen,

R5 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl, represents the grouping below,

-A ^ -A ³

in which

A ^ 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 in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i- propylthio, n-, i-, s- or t-butylthio, methylsulfonyl, ethylsulfonyl, n- or i- Propylsulfonyl, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl

Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyl pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, or represents in each case optionally substituted by nitro, cyano, carboxyl, 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.

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

n represents 1 or 2,

Q represents oxygen or sulfur,

Rl is in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, and

R ^{2 represents} the aromatic group defined below,

wherein

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen,

R5 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl,

R6 represents the grouping below, -Al-A ² -A ³

in which

A 'stands for the grouping -NA ⁴ -, in which A ^{4 represents} hydrogen,

Methylsulfonyl or ethylsulfonyl,

A ^{2 stands} for -SO ₂ -,

A ^J for each optionally by fluorine, chlorine, methoxy or

Ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine, cyano or methyl, or for each optionally phenyl or benzyl substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl, and

R ^{7 represents} hydrogen.

The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These residual definitions can be among themselves, that is, between the specified

Areas of preferred connections, can be combined as desired.

The new substituted 1,3-diaza-2- (thi) oxo-cycloalkanes of the general formula (I) are notable for 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! -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, as part of the substituent definition, carrying out electrophilic or nucleophilic substitution reactions in the customary manner.

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

(IV) (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 represent halogen (in particular chlorine), alkoxy (in particular methoxy or ethoxy), alkoxyalkoxy (in particular (methoxyethoxy or ethoxyethoxy), phenoxy or imidazolyl,

optionally in the presence of a reaction auxiliary, e.g. Pyridine and optionally in the presence of a diluent, e.g. Toluene.

Reaction of l, 3-diaza-2- (thi) oxo-cycloalkanes of the general formula (VI) with

Halogen compounds of the general formula (VII)

(VI) (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 e.g. Ethyl diisopropyl amine, and optionally in the presence of a diluent such as e.g. Acetonitrile.

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

(VIII) (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 e.g. Potassium carbonate, and optionally in the presence of a diluent such as e.g. Acetone.

If, for example, l-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) oxocycloalkanes 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), n, Q and R ¹ preferably or in particular have 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.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (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 (1992), 7339-7342; Synth. Commun. 27 (1997), 3565-3571).

The halogen compounds to be used further as starting materials in the process of the invention are generally defined by the formula (III). In 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 as preferred, particularly preferred or as very particularly preferred for

R ^{2 was} specified; X ² preferably represents fluorine or chlorine, in particular fluorine.

The starting materials of the general formula (III) are known and / or can be prepared by 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. Inert organic solvents are particularly suitable as diluents. 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-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric 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 auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction auxiliaries. 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 methoxide, - ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, 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 1,5-diazabicyclo [5,4,0] undec-7-ene (DBU).

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 20 ° 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 mög _¬ lich to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. 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: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Sonuum, Carduus , Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, 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, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means limited to these

Limited genera, but extends in the same way to other plants.

The compounds are suitable, depending on the concentration, for total weed control, for example on industrial and track systems and on paths and squares with and without tree cover. Likewise, the compounds for weed control in permanent crops, for example forests, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, be used on ornamental and sports turf and pastures and for selective weed control in annual crops. The compounds of formula (I) according to the invention are particularly suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon crops both in the pre-emergence and in the post-emergence process.

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

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, that is liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can 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, e.g. 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.

The following are suitable as solid carriers: for example 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 Question: eg broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; Possible emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example

Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

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 for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example

Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium),

Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Benazolin (-ethyl), Benfuresate, Bensulfuron (-methyl), Bentazon, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydafenole, Butylate, Butylate, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, chloridazone, chlorimuron (-ethyl), chloronitrofen, chlorosulfuron,

Chlortoluron, Cinmethylin, Cinosulfuron, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloransulam (- methyl), Cumyluron, Cyanazine, Cycloate, Cyclosulfamurb-, Cyclutyl, Cycloxydimim, Cyclofydimimon 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialallate, dicamba, diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufen- zopyr, dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate - Ethoxyan, Fenoxapuronone P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, florasulam,

Fluazifop (-P-butyl), flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), fluopoxam, flupropacil, flurpyrsulfuron (-methylurenols- (-butyl), Fluri- done, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium),

Halosafen, Haloxyfop (-ethoxyethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Ioxynil, Isopropalin, Isoproturon, Isouron, Isouron, Isouron, Isouron, Isouron, Isouron, Isouron Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron,

(alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfyefuron, Paras Pelargonic acid, pendimethalin, pentoxazone, phenmedipham, piperophos, pretilachlor, primisulfuron (methyl), prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-ethyl), Pyrazolate, Pyrazosulfuron (-ethyl), Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridate, Pyriminobac (-methyl) - Pyrithiacin, Pyrithiobin Quinmerac, Quinoclamine, Quizalofop (-P-ethyl), Quizalofop (-P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfefrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebutam uron, terbuthylazine, terbutryn, thenyl chlorine, thiafluamide, thiazopyr, thidiazimine, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, triduralin, tridiphonone, tridiphonone.

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

Manufacturing examples:

example 1

A mixture of 5.8 g (50 mmol) of l-methylimidazolidin-2-thione, 8.6 g (55 mmol) of 2,4,5-trifluorobenzonitrile, 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 poured into a mixture of approximately equal volumes of methylene chloride and water while stirring and acidified with 2N hydrochloric acid. The organic phase is separated off, 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 l-methyl-3- (4-cyano-2,5-difluorophenyl) imidazolidin-2-thione with a melting point of 143 ° C. are obtained.

Example 2

(Follow-up implementation) A mixture of 2.0 g (8 mmol) l-methyl-3- (4-cyano-2,5-difluorophenyl) imidazolidin-2-thione, 1.8 g (16 mmol) ethanesulfonic acid amide, 2 , 2 g (16 mmol) of potassium carbonate and 50 ml of dimethyl sulfoxide is stirred at 100 ° C. for 16 hours. After cooling, the mixture is poured into a mixture of approximately equal volumes of methylene chloride and water with stirring and acidified with 2N hydrochloric acid. The organic phase is separated off, washed with water, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with isopropanol and the crystalline product is isolated by suction.

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

Analogous to preparation examples 1 to 2 and in accordance with the general

Description of the production processes according to the invention can also be used, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

Table 1: Examples of the compounds of the formula (I)

9/59977

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The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase inversion 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 ^a) .

(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 with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

9/59977

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Using examples of turns:

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, 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.

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

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 Examples 2, 5, 8, 9, 10, 11 and 12, with good tolerance to crop plants such as, for example, maize, show a 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

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.

It means:

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

In this test, for example, the compounds according to Preparation Examples 2, 8, 9, 10 and 12 show, in some cases, good tolerance to crop plants, such as e.g. Barley, strong action against weeds.

Claims

claims

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,

Rl represents hydrogen, formyl or optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl, and

R ^{2 represents} an optionally substituted, optionally heterocyclically fused, monocyclic or bicyclic aromatic group.

Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that

n for 1,

2 or 3 stands,

Q represents oxygen or sulfur, R ¹ for hydrogen, formyl or for alkyl, alkoxy, alkylamino, dialkylamino each substituted by cyano, halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonyl, C 1 -C 4 -alkoxycarbonyl or Moφholinyl, each with 1 to 6 carbon atoms in the alkyl groups, each for alkenyl or alkynyl which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxycarbonyl, or each having 2 to 6 carbon atoms, or for cycloalkyl or which is each optionally substituted by cyano, halogen or C 1 -C 4 -alkyl 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 the alkyl groups, each optionally substituted by cyano, halogen or C 4 -C 4 -alkoxy , or for cycloalkylcarbonylamino with 3 to 6 carbon atoms in the cycloalkyl part optionally substituted by cyano, halogen, Cj-C4-alkyl or Cι-C4-haloalkyl, or for optionally by cyano, nitro, Cj-C4-alkyl, C1-C4- Haloalkyl, C 1 -C 4 -alkoxy or C 4 -C 4 -haloalkoxy substituted phenylcarbonylamino,

R ^{4 represents} hydrogen, nitro, cyano, fluorine, chlorine or bromine,

R5 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,

R6 represents the grouping below,

-Ai-A ^ ³

in which

A for a single bond, for oxygen, sulfur, -SO-,

-SO2-, -CO- or the grouping -NA ⁴ -, where A ^{4 is}

Hydrogen, hydroxy, C 1 -C 4 alkyl, C 4 -C 4 alkenyl, C 3 -C 4 alkynyl, C 1 -C 4 alkoxy, phenyl, C 1 -C 4 alkyl carbonyl,

Phenylcarbonyl, -C4-alkyl-sulfonyl or phenylsulfonyl,

A furthermore for Cj-Cg-alkanediyl, C2-C6-alkenediyl, C2-, in each case optionally substituted by fluorine, chlorine or bromine,

C6-azaalkenediyl, C2-Cg-alkindiyl, C3-Cg-cycloalkanediyl, C3-C6-cycloalkenediyl or phenylene,

A ^{2 stands} for a single bond, for oxygen, sulfur, -SO-, -SO2-, -CO- or the grouping -NA ⁴ -, wherein A ^{4 stands} for Is 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 \ -Cg-alkanediyl, C2-Cö-alkenediyl, C2-

Cö-azaalkenediyl, C2-Cö-alkindiyl, C3-C6-cycloalkanediyl, C3-Cg-cycloalkendiyl or phenylene,

A ³ for hydrogen, hydroxy, mercapto, amino, cyano, isocyano, thiocyanato, nitro, carboxy, carbamoyl, thiocarbamoyl,

Sulfo, chlorosulfonyl, fluorine, chlorine, bromine, for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkoxycarbonyl or dialkoxy (thio) - phosphoryl, each with 1 to in each case substituted by fluorine, chlorine or C 1 -C 4 -alkoxy 6 carbon atoms in the

Alkyl groups, each for alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, each optionally substituted by fluorine or chlorine, each having 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl groups, each optionally substituted by fluorine , Chlorine, cyano, carboxy, C 1 -C 4 -alkyl and / or C 1 -C 4 alkoxycarbonyl-substituted cycloalkyl, cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 up 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 -haloalkyl, Cj-C4-alkyloxy, Cj-C4-haloalkyloxy and / or C 1 -C 4 alkoxy-carbonyl substituted phenyl, phenoxy, phenyl C 1 -C 4 alkyl, phenyl C 1 -C 4 -alkoxy, phenoxycarbonyl or phenyl-C 4 -C 4 -alkoxy-carbonyl,

A ³ furthermore for (in each case optionally fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl,

Oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C \ -C4-alkyl, furyl-Cj-C4-alkyl, th4-alkyl-Cj , Oxazolyl-C ₄ -C ₄ -alkyl, isoxazole-C 1 -C ₄ -alkyl, thiazole-C 1 -C ₄ -alkyl, pyridinyl-Cι-C4-alkyl,

Pyrimidinyl -CC-C4-alkyl, pyrazolylmethoxy, furylmethoxy, stands for perhydropyranylmethoxy or pyridylmethoxy, and

R ^{7 "represents} hydrogen, fluorine or chlorine,

or two adjacent radicals - R ³ and R ⁴ , R ⁴ and R *, R ^ and R ^Ö or R ^ and R7 - together represent one of the following groups

-Q3-CQ ⁴ -, -Q3-CQ ⁴ -Q5-, -C (R ⁸ , R9) -CQ ⁴ -, -C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -, -Q ³ -C (R ⁸ , R9) -C (R ⁸ , R9) - , -Q -C (R ⁸ , R ⁹ ) -C (R ⁸ , R9) -Q5-, -C (R, R9) -C (R ⁸ , R9) -CQ ⁴ -, -Q ³ -C ( R) = C (R ⁸ ) -, -C (R ⁸ ) = C (R) -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 , R9) -, -Q ³ -CQ ⁴ -N (R ¹⁰ ) -, -Q ³ -C (R ⁸ , R9) -CQ ⁴ -N (Rl0).,

-C (R ⁸ , R9) -Q ³ -CQ ⁴ -N (R1 °) -, -C (R ⁸ , R9) -C (R ⁸ , R9) -N (R ¹⁰ ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R9) -CQ ⁴ -N (RI0) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -, -C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹ °) -, -C (R, R9) -CQ -N (R ¹ °) -, -N (R ¹⁰ ) -C (R ⁸ ; R9) - CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ ) = NN (R ¹⁰ ) -, -Q ³ -CQ ⁴ -C (R ⁸ , R9) -N (R10) -, Q -C (R ⁸ , R9) -C (R, R9) -CQ ⁴ -N (R ¹⁰ ) - 9/59977

- 45 -

in which

Q ³ , Q ⁴ and Q-> are the same or different and each represents oxygen or sulfur,

R ⁸ and R are the same or different and individually represent hydrogen, fluorine, chlorine, bromine or -CC-alkyl or together represent C2-C5-alkanediyl, and

R O for hydrogen, hydroxy, for optionally by cyano,

Fluorine, chlorine, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylcarbonyl or C] - C4-alkoxy-carbonyl-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulfonyl each having 1 to 6 carbon atoms in the alkyl groups, for each if necessary by Fluorine, chlorine or bromine substituted alkenyl or

Alkynyl each having 2 to 6 carbon atoms, for each cycloalkyl or cycloalkylalkyl optionally substituted by fluorine, chlorine, bromine or C 1 -C 4 -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 3 atoms in the alkyl part, for each alkoxy or alkenyloxy optionally substituted by fluorine and / or chlorine each having up to 6 carbon atoms, or for each optionally by cyano, fluorine, chlorine, C 1 -C 4 -alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C4-Haloalkoxy substituted benzyl or benzyloxy.

3. Substituted l, 3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that

n represents 1, 2 or 3, represents oxygen or sulfur,

R for hydrogen, formyl or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally by fluorine or Chlorine-substituted propenyl, 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, methoxycarbonylamino, ethoxycarbonylamino, methylaminocarbonocamylamino, ethylaminoaminoaminoaminoaminoamino

Cyclopropylcarbonylamino or phenylcarbonylamino (benzoylamino),

R ^{4 represents} hydrogen, fluorine or chlorine, R5 represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy,

R ^{Ö represents} the grouping below,

-Ai-A ² ^ ³

in which

A stands for a single bond, for oxygen, sulfur, -SO-, -SO2-, -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 or ethylsulfonyl,

A * also 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-, -SO2-, -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 each methyl, ethyl, n- or i-propyl, 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, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl , Methylsulfonyl,

10 ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethyl - amino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl , Dimethoxyphosphoryl, diethoxyphosphoryl or dipropoxyphosphoryl, diisoprop

15 oxyphosphoryl, for each optionally by fluorine or

Chlorine-substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylidenemino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino,

20 butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, each optionally substituted by fluorine, chlorine, cyano, carboxy, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl,

25 cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopentylidenamino, cyclohexylideneamino, cyclopentyloxycarbonyl, cyclohexyloxy

30 cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, 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 phenyl, phenyloxy, benzyl, Phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl,

A ³ also for (in each case fully or partially hydrogenated) pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazoylmethyl Thienylmethyl, oxazolylmethyl, isoxazolmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy, and

R? represents hydrogen, fluorine or chlorine,

or two adjacent residues - R ³ and R ⁴ , R ⁴ and R ~>, R5 and R ^ or R ^Ö and R? - together represent one of the groups below

-Q3-CQ ⁴ -, -Q3-CQ ⁴ -Q5-, -Q3-C (R8, R9) -Q5-, -C (R ⁸ , R ⁹ ) -CQ ⁴ -, -C (R ⁸ , R9 ) -Q ³ -CQ -, -Q ³ -C (R, R9) -C (R ⁸ , R9) -, -Q ³ -C (R ⁸ , R ⁹ ) -C (R ⁸ , R9) -Q5 -, -C (R ⁸ , R9) -C (R ⁸ , R ⁹ ) -CQ ⁴ -,

-Q ³ -C (R ⁸ ) = C (R ⁸ ) -, -C (R) = C (R ⁸ ) -CQ ⁴ -, -Q -C (R ⁸ , R ⁹ ) -CQ ⁴ -, - N (R ¹⁰ ) -C (R ⁸ ; R9) -CQ ⁴ -, -C (R ⁸ ) = N-, -Q ³ -CQ ⁴ -C (R ⁸ , R ⁹ ) -, -Q -CQ ⁴ -N (R ¹⁰ ) -, -Q ³ -C (R ⁸ , R9) -CQ ⁴ -N (Rl ⁰ ) -, -C (R ⁸ , R ⁹ ) -Q ³ -CQ ⁴ -N (R ¹ 0) -, -C (R ⁸ , R9) -C (R ⁸ , R ⁹ ) -N (R ^{1 0} ) -, -C (R ⁸ , R ⁹ ) -C (R ⁸ , R9) -CQ ⁴ -N (R ¹ 0) -, -C (R ⁸ ) = C (R ⁸ ) -N (R ¹⁰ ) -,

-C (R ⁸ ) = C (R ⁸ ) -CQ ⁴ -N (R ¹⁰ ) -, -C (R ⁸ , R9) -CQ ⁴ -N (R ¹⁰ ) -, -N (R ¹⁰ ) -C (R ⁸ ; R9) -CQ ⁴ -N (RlO) -, -C (R ⁸ ) = NN (RlO) -, -Q -CQ -C (R, R9) -N (R ¹ 0) -, Q ³ -C (R ⁸ , R9) -C (R, R9) -CQ ⁴ -N (Rl 0).

in which

Q ³ , Q ⁴ and Q5 are the same or different and each represents oxygen or sulfur,

RIO 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 butinyl, each optionally substituted by fluorine, chlorine or bromine, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl,

Cyclobutylmethyl, cyclopentylmethyl or 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, by cyano, Fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted benzyl or benzyloxy.

4. Substituted l, 3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that n represents 1 or 2,

Q represents oxygen or sulfur,

R ^{2 represents} the aromatic group defined below,

woπn

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen,

R6 represents the grouping below,

-A * -A ² -A ³

in which

A * stands for a single bond, A ^{2 represents} a single bond,

A ³ for hydroxy, amino, cyano, nitro, carboxy, carbamoyl, sulfo, fluorine, chlorine, bromine, each for if appropriate

Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n - or i-propoxy, n-, i-, s- or t-butoxy, 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-propoxycarbonyl, for each optionally by

Fluorine or chlorine substituted propenyl, butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylidene amino, butylideneamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butinyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyl 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, cyclopentylhexoxycarbonyl carbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, 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 benzyloxycarbonyl, and

R ^{7 represents} hydrogen.

5. Substituted l, 3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that

n represents 1 or 2,

Q represents oxygen or sulfur,

R ^{2 represents} the aromatic group defined below,

wherein

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen,

R5 represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl, R6 represents the grouping below,

-A * -A ² -A ³

in which

A * 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-, each optionally 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, cyclopropyl pyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, or represents in each case optionally substituted by nitro, cyano, carboxyl, 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 99/59977

- 55 -

R ^{7 represents} hydrogen.

6. Substituted l, 3-diaza-2- (thi) oxo-cycloalkanes according to claim 1, characterized in that

n represents 1 or 2,

Q represents oxygen or sulfur,

R ^{2 represents} the aromatic group defined below,

woπn

R ^{3 represents} hydrogen, fluorine or chlorine,

R ^{4 represents} hydrogen,

R6 represents the grouping below, 99/59977

56 -

-Ai-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 optionally by fluorine, chlorine, methoxy or

Ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally with fluorine, chlorine,

Cyano or methyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or for phenyl or benzyl, each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl stands, and

R ^{7 represents} hydrogen.

7. A process for the preparation of substituted l, 3-diaza-2- (thi) oxo-cycloalkanes 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 ^l -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 to 6.

9. Use of at least one substituted 1,3-diaza-2- (thi) oxocycloalkane according to one of claims 1 to 6 for combating undesirable plants.