KR20010043505A - Substituted 1,3-diaza-2-(thi) oxo-cycloalkanes - Google Patents

Abstract

The present invention relates to novel substituted 1,3-diaza-2- (thio) oxo-cycloalkanes of the formula (I), their preparation and their use as herbicides:

(I)

In this formula,

n represents 1, 2 or 3,

Q represents oxygen or sulfur,

R ¹ represents an optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

R ² represents an optionally substituted monocyclic or bicyclic aromatic group optionally fused to a heterocycle.

Description

Substituted 1,3-diaza-2- (thi) oxo-cycloalkanes < RTI ID = 0.0 >

Some of the substituted 1,3-diaza-2- (thio) oxo-cycloalkanes have already been cited in J. Chem. Eng. Data 13 (1968), 582-585 - Chem. Abstracts 69: 106613 ). ≪ / RTI > However, none of the biological properties of these compounds have been disclosed.

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

A novel substituted 1,3-diaza-2- (thio) oxo-cycloalkane with the following formula I was found:

(I)

In this formula,

n represents 1, 2 or 3,

Q represents oxygen or sulfur,

R ¹ represents hydrogen, formyl or an optionally substituted alkyl, alkoxy, alkylamino, dialkylamino, alkenyl, alkynyl, cycloalkyl or cycloalkylalkyl,

R ² represents an optionally substituted monocyclic or bicyclic aromatic group optionally fused to a heterocycle.

In the substituent definition, a hydrocarbon chain such as alkyl - and in connection with a heteroatom such as alkoxy - are each straight or branched.

n represents preferably 1, 2 or 3;

Q preferably represents oxygen or sulfur;

R ¹ preferably represents hydrogen, formyl, or has in each case 1 to 6 carbon atoms in the alkyl group and is optionally substituted by one or more substituents each independently selected from the group consisting of cyano, halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkyl- Alkyl, alkoxy, alkylamino, dialkylamino, or having 2 to 6 carbon atoms, which is unsubstituted or substituted by C ₁ -C ₄ -alkoxy-carbonyl or morpholinyl, , Alkenyl or alkynyl optionally substituted by halogen or C ₁ -C ₄ -alkoxy-carbonyl, or alternatively 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 6 carbon atoms in the alkyl moiety, Cycloalkyl or cycloalkylalkyl having 4 carbon atoms and each being optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl;

R ² preferably represents the following aromatic group;

here,

R ³ represents hydrogen, nitro, amino, cyano, formylamino or halogen, each of which has 1 to 6 carbon atoms in the alkyl group and is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy Or represents an alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, or phenyl group which has 3 to 6 carbon atoms in the cycloalkyl moiety and which optionally may be substituted by cyano, halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ - substituted by halogenoalkyl or represent a cycloalkyl-alkyl-carbonyl amino, or cyano, nitro, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -halogenoalkoxy;

R ⁴ represents hydrogen, nitro, cyano, fluorine, chlorine or bromine;

R ⁵ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, fluorine, chlorine, bromine or is optionally substituted by fluorine and / or chlorine, each having up to 4 carbon atoms Alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl;

R ⁶ represents the following group;

-A ¹ -A ² -A ³

here,

A ¹ is represented by a single bond, or oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the group -NA ⁴ - represents a, wherein A ⁴ is hydrogen, hydroxyl, 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 - alkyl-carbonyl, phenylcarbonyl, C ₁ -C ₄ ≪ / RTI > alkyl-sulfonyl or phenylsulfonyl,

A ¹ is also, C ₁ -C _6, which is optionally substituted by each fluorine, chlorine or bromine-alkanediyl, C ₂ -C ₆ al canned yl, C ₂ -C ₆ - aza al canned yl, ₂ C -C ₆ - alkyne diyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - cycloalkenyl denotes a canned one or phenylene,

A ² represents a single bond, or oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the group -NA ⁴ - represents a, wherein A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ -alkoxy, phenyl, C ₁ -C ₄ -alkylsulfonyl or phenylsulfonyl,

A ² is optionally fluorine-addition respectively, which is substituted by chlorine or bromine, C ₁ -C ₆ - alkanediyl, C ₂ -C ₆ - Al canned yl, C ₂ -C ₆ - aza al canned yl, ₂ C -C ₆ - alkyne diyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - cycloalkenyl denotes a canned one or phenylene,

A ³ represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyanato, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, , Or an alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, alkylthio, alkylthio, alkylthio, alkylthio, or alkylthio group, each of which has 1 to 6 carbon atoms in the alkyl group and is optionally substituted by fluorine, chlorine or C ₁ -C ₄ -alkoxy , Dialkylamino, alkoxycarbonyl or dialkoxy (thio) phospholyl, each of which has 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl group and which is optionally substituted by fluorine or chlorine, Alkenyl, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, or each represents a 3 If not 6 carbon atoms, and suitable, in the alkyl group has 1 to 4 carbon atoms and each optionally fluorine, chlorine, cyano, carboxyl, C ₁ -C ₄ - alkyl and / or C ₁ -C ₄ - alkoxy-carbonyl Cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each of which is optionally substituted by nitro, cyano, cyano, carboxyl, fluorine, chlorine, bromine, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkyloxy, C ₁ -C ₄ - halogenoalkyl alkyloxy and / or C ₁ -C ₄ - alkoxy-carbonyl which is substituted by phenyl, phenoxy, phenyl -C ₁ -C ₄ - alkyl, phenyl -C ₁ -C ₄ - alkoxy, phenoxy-carbonyl or phenyl -C ₁ -C ₄ -alkoxy-carbonyl,

A ³ is also a pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl , Thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C ₁ -C ₄ -alkyl, furyl-C ₁ -C ₄ -alkyl, thienyl-C ₁ -C ₄ -alkyl, oxazolyl- C ₁ -C ₄ - alkyl, isoxazol--C ₁ -C ₄ - alkyl, thiazol--C ₁ -C ₄ - alkyl, pyridinyl -C ₁ -C ₄ - alkyl, pyrimidinyl, -C ₁ -C ₄ -Alkyl, pyrazolylmethoxy, furylmethoxy, perhydropyranylmethoxy or pyridylmethoxy, each of which is optionally completely or partially hydrogenated,

R ⁷ represents hydrogen, fluorine or chlorine,

Or each 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;

here,

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 each represents hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl or together represent C ₂ -C ₅ -alkanediyl,

R ¹⁰ has a hydrogen, 1 to 6 carbon atoms represent a hydroxyl or in each alkyl group and are each cyano, fluorine, chlorine, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkyl-carbonyl, or Alkyl, alkylcarbonyl, alkoxy-carbonyl or alkylsulfonyl optionally substituted by C ₁ -C ₄ -alkoxy-carbonyl or each having 2 to 6 carbon atoms and optionally substituted with fluorine, chlorine Or alkenyl or alkynyl optionally substituted by bromine, or each of which has 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 3 atoms in the alkyl moiety and optionally fluorine, chlorine, bromine Cycloalkyl or cycloalkylalkyl, which is unsubstituted or substituted by C ₁ -C ₄ -alkyl, or each of which has 6 or fewer carbon atoms and which is optionally substituted by fluorine and / or chlorine, C ₁ -C ₄ -halogenoalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -halogenoalkyl, each of which is optionally substituted by one or more substituents independently selected from the group consisting of halogen, fluorine, chlorine, C ₁ -C ₄ -alkyl, Benzyl or benzyloxy which is substituted by C ₄ -halogenoalkoxy.

n represents particularly preferably 1, 2 or 3;

Q particularly preferably represents oxygen or sulfur;

R ¹ particularly preferably represents hydrogen, formyl or methyl, ethyl, n- or i-propyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, butenyl, propynyl or butynyl, each of which is optionally substituted by fluorine or chlorine, or is optionally substituted by one or more substituents each independently selected from the group consisting of cyano, fluorine, chlorine, methyl Or cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl substituted by ethyl;

R ³ preferably represents hydrogen, nitro, amino, cyano, formylamino, fluorine, chlorine, or represents methyl, trifluoromethyl, acetylamino, propionylamino, butyroylamino, (Benzoylamino) such as, for example, amino, trifluoroacetylamino, methoxycarbonylamino, ethoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, cyclopropylcarbonylamino or phenylcarbonylamino ;

R ⁴ preferably represents hydrogen, fluorine or chlorine;

R ⁵ preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy;

R ⁶ particularly preferably represents the following group:

-A ¹ -A ² -A ³

here,

A ¹ represents a single bond or represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or group -NA ⁴ -, wherein A ⁴ represents hydrogen, hydroxyl, methyl, Or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl,

A ¹ is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane- 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-

A ² represents a single bond or represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or group -NA ⁴ -, wherein A ⁴ is hydrogen, hydroxyl, methyl, Or represents i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl,

A ² is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane- 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne-

A ³ represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine, or methyl Propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i- n-, i-, s- or t-butyloxy, methylthio, ethylthio, n- or i-propylthio, n-, Or methylthio, ethylamino, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, -Propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, Diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphor Butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butyrylideneamino, propenyl, which is optionally substituted by fluorine or chlorine, Butynyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy or cyclohexyloxy which is substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Cyclopentyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or represents a cyclohexylmethoxycarbonyl group or a cyclohexylmethoxycarbonyl group, or a cyclohexylmethoxycarbonyl group, or a cyclohexylmethoxycarbonyl group, Are each independently selected from the group consisting of nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, which is substituted by trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl,

A ³ is also a pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl , Triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolylmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy Optionally hydrogenated in whole or in part;

R ⁷ 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;

here,

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 each represents hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene)

R ¹⁰ represents hydrogen, hydroxyl, or methyl, ethyl, or propyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl propenyl, butynyl, propynyl or butynyl, each of which is optionally substituted by fluorine, chlorine or bromine, in the presence of a suitable base such as n- or i-propyl, n-, i-, s- or t- Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine, bromine, methyl or ethyl, Ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each of which is optionally substituted by fluorine and / or chlorine, Respectively, Benzyl or benzyloxy, each of which is optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy;

n more particularly preferably represents 1 or 2;

Q particularly preferably represents oxygen or sulfur;

R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy;

R ³ particularly preferably represents hydrogen, fluorine or chlorine;

R ⁴ particularly preferably represents hydrogen;

R ⁵ particularly preferably represents cyano, thiocarbamoyl, chlorine, bromine, methyl or trifluoromethyl;

R < ⁶ > particularly preferably represents the following group:

-A ¹ -A ² -A ³

here,

A ¹ represents a single bond,

A ² represents a single bond,

A ³ is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, each of which represents hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine or is optionally substituted by fluorine, chlorine, methoxy or ethoxy n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i- , i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i- Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylsulfinyl, Amino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Lt; / RTI > unsubstituted or substituted by chlorine, such as propenyl, butenyl, Butenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy , Each of which may be optionally substituted with one or more substituents selected from fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbamoyl, Cyclobutyloxy, cyclopentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, Cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or is optionally substituted with one or more substituents each independently selected from 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 phenoxy, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl;

R ⁷ particularly preferably represents hydrogen.

Preferred are compounds of formula I which comprise a combination of the meanings mentioned above as being preferred according to the invention.

Particularly preferred are those compounds of formula I which comprise a combination of the meanings mentioned in the invention according to which it is particularly preferred.

Particularly preferred are those compounds of formula I which comprise a combination of the meanings mentioned in the invention according to which it is particularly preferred.

A more preferred group is a compound of formula I having the following substituent definitions:

n represents 1 or 2,

Q represents oxygen or sulfur,

R ¹ represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ² represents the following aromatic group:

here,

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 following group:

-A ¹ -A ² -A ³

here,

A ¹ represents the group -NA ⁴ -, wherein A ⁴ represents hydrogen, methylsulfonyl or ethylsulfonyl,

A ² represents a single bond or -CO-,

A ³ represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i- Or each of which may be optionally substituted with one or more substituents selected from the group consisting of fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxy, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopropylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylmethyl, , Cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy Or each of which may be optionally substituted with one or more substituents selected from nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Phenoxy, benzyl or benzyloxy, which is substituted by fluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl,

R ⁷ represents hydrogen.

A still more preferred group is a compound of formula I having the following substituent definitions:

n represents 1 or 2,

Q represents oxygen or sulfur,

R ¹ represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ² represents the following aromatic group:

here,

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 following group:

-A ¹ -A ² -A ³

here,

A ¹ represents the group -NA ⁴ -, wherein A ⁴ represents hydrogen, methylsulfonyl or ethylsulfonyl,

A ² represents -SO ₂ -,

A ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Cyclobutyl, cyclopentyl or cyclohexyl which is unsubstituted or substituted by fluorine, chlorine, cyano or methyl, or represents a phenyl group which may be substituted by nitro, cyano, fluorine, chlorine, bromine, , Phenyl or benzyl, which is substituted by methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl,

R ⁷ represents hydrogen.

The definitions of the radicals referred to above in general terms or as preferred ranges apply not only to the final products of formula I but also to the starting materials or intermediates necessary for each production case. These radical definitions can be combined with one another if desired, i.e. a combination between the preferred compounds in the stated ranges is possible.

The novel substituted 1,3-diaza-2- (thio) oxo-cycloalkanes of formula I are distinguished by a strong and selective herbicidal activity.

The novel substituted 1,3-diaza-2- (thio) oxo-cycloalkanes of formula (I)

Diaza-2- (thio) oxo-cycloalkane of the formula (II) is reacted, if appropriate, with a halogen compound of the formula (III) in the presence of a reaction aid and, if appropriate, in the presence of a diluent, Lt; RTI ID = 0.0 > nucleophilic < / RTI > substitution reaction in a conventional manner within the definition:

≪ RTI ID = 0.0 &

(III)

X ¹ -R ²

In this formula,

n, Q, R ¹ and R ² are as indicated above,

X ¹ represents halogen.

In principle, the compounds of formula I can also be synthesized as shown in the following scheme:

If appropriate in the presence of a reaction aid such as, for example, pyridine and, if appropriate, in the presence of a diluent such as, for example, toluene, the reaction of a diamine of formula IV with a (thio)

In this formula,

n, Q, R ¹ and R ² are as indicated above,

Y ¹ and Y ² are the same or different and each represent halogen (especially chlorine), alkoxy (especially methoxy or ethoxy), alkoxyalkoxy (especially methoxyethoxy or ethoxyethoxy), phenoxy or imidazolyl .

Diazabicyclohexylcarbodiimide, if appropriate in the presence of a reaction aid such as, for example, ethyl-diisopropylamine, and if appropriate in the presence of a diluent such as, for example, acetonitrile, Reaction of a cycloalkane with a halogen compound of the following formula VII:

In this formula,

n, Q, R ¹ and R ² are as indicated above,

X ² represents halogen (especially chlorine, bromine or iodine).

If appropriate in the presence of a reaction aid such as, for example, potassium carbonate and, if appropriate, in the presence of a diluent such as, for example, acetone, a reaction of (thio) urea of formula VIII with an α, ω- :

In this formula,

n, Q, R ¹ and R ² are as indicated above,

E ¹ and E ² represent a leaving group which may be substituted by a nucleophile such as halogen (especially chlorine or bromine) or alkylsulfonyloxy (especially methylsulfonyloxy).

For example, when 1-methyl-imidazolidin-2-one and 2,4,5-trifluorobenzonitrile are used as starting materials, the reaction path of the process according to the invention can be summarized by the following structural reaction scheme Can:

(II) provides a general definition of the 1,3-diaza-2- (thio) oxo-cycloalkane to be used as starting material in the process according to the invention for the preparation of compounds of formula (I). In formula II, n, Q and R ¹ are preferably, or in particular, for n, Q and R ¹ in the above in connection with the description of the compounds of formula I according to the invention, or already preferably, is especially preferred It has the meaning mentioned.

The starting materials of formula II can be prepared by known and / or known methods (see J. Am. Chem. Soc. 80 (1958), 6409-6412; J. Chem. Soc. Perkin Trans. 1 , J. Org. Chem. 22 (1957), 1581, J. Org. Chem. 28 (1992), 7339-7342, Synth. Commun. 27 (1997), 3565-3571).

Formula III provides a general definition of a halogen compound to be used also as starting material in the process according to the invention. In formula (III), R < ² > is preferably, or in particular, the meaning already mentioned above for R < ² > in relation to the description of compounds of formula (I) according to the invention, Have; X ² preferably represents fluorine or chlorine, particularly fluorine.

Starting materials of formula III can be prepared by known methods and / or by methods known per se (see EP-A-191181, EP-A-370332, EP-A-431373, EP- -597360).

The process according to the invention for the preparation of compounds of formula I is preferably carried out using a diluent. Suitable diluents are, in particular, inert organic solvents. They may be chosen in particular from the group consisting of aliphatic, alicyclic or aromatic, such as benzene, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride, hydrocarbon; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; Ketones such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric triimide; Esters such as methyl acetate or ethyl acetate, and sulfoxide such as dimethyl sulfoxide.

The process according to the invention for the preparation of the compounds of formula (I) is preferably carried out using a reaction aid. Suitable reaction aids are generally conventional inorganic or organic bases or acid acceptors. These are preferably selected from the group consisting of acetates, amides, carbonates, hydrogencarbonates, hydrides, hydroxides or alkoxides of alkali or alkaline earth metals such as sodium acetate, potassium acetate or calcium acetate, lithium amide, sodium amide, Amide or calcium amide, sodium carbonate, potassium carbonate or calcium carbonate, sodium hydrogencarbonate, potassium hydrogencarbonate or calcium hydrogencarbonate, lithium hydride, sodium hydride, potassium hydride or calcium hydride, lithium hydroxide, Sodium hydroxide, potassium hydroxide or calcium hydroxide, sodium methoxide or potassium methoxide, sodium ethoxide or potassium ethoxide, sodium n- or i-propoxide or potassium n- or i-propoxide , Sodium n-, i-, s- or t- Seed, or potassium n-, i-, s- or t- butoxide; Also included are basic organic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl- cyclohexylamine, dicyclohexylamine, ethyl- Dimethyl- aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4- Dimethyl-pyridine, 4-dimethyl-amino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [ (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0 ] Undec-7-ene (DBU).

When carrying out the process according to the invention, the reaction temperature may vary within a practical range. In general, the process is carried out at a temperature of from 0 ° C to 150 ° C, preferably from 20 ° C to 120 ° C.

The process according to the invention is generally carried out under atmospheric pressure. However, the process according to the invention can be carried out at elevated or reduced pressure, generally 0.1 bar to 10 bar.

In order to carry out the process according to the invention, the starting materials are generally used in about the same molar amount. However, one component can also be used in excess. The reaction is generally carried out in the presence of a quench formulation in a suitable diluent and the reaction mixture is generally stirred at the desired temperature for several hours. The work-up is carried out by a conventional method (Reference Production Example).

The active compounds according to the invention can be used as a defoliant, a drying agent, a stem-killer and, in particular, a weed killer. In the broadest sense, weeds should be understood as all plants that grow in undesirable locations. The extent to which the substances according to the invention act as a comprehensive or selective herbicide depends essentially on the amount used.

The active compounds according to the invention can be used, for example, in connection with the following plants:

Two-leaf weeds in the genus: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Such as Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, ), Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledons of the following genus: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum ), Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, ) And Cucurbita.

Monocotyledonous weeds of the following genus: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusin, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, They are: Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, ), Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.

The foliage crops in the following are: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

However, the use of an active compound according to the present invention is not limited to the above genus, but also extends to other plants in the same manner.

The compounds of the present invention are suitable for the total relief of weeds on sidewalks and squares, for example on industrial sites and railroads, and on planted or unplanted trees, depending on the concentration. Likewise, the compounds of the present invention may be used in combination with plant growth regulators such as, for example, plantations, orchards, orchards, vineyards, citrus orchards, nuts orchards, banana farms, coffee farms, tea farms, rubber farms, coconut farms, cocoa farms, And to relieve weeds in perennial crops growing on racetrack grass and pastures, and to selectively relieve weeds in annual crops.

The active compounds of formula (I) according to the invention are particularly suitable for the selective remediation of monocotyledonous weeds and dicotyledonous weeds in both monocot crops and dicot crops by both germination and post-germination methods.

The active compounds may be in the form of solutions, emulsions, wettable powders, suspensions, powders, powders, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compounds, ≪ / RTI >

These formulations are prepared in a known manner, for example by mixing the active compounds with extenders, i. E. Liquid solvents and / or solid carriers, optionally using surfactants, i.e. emulsifiers and / or dispersants and / or foam- .

When water is used as an extender, for example, an organic solvent can also be used as an auxiliary solvent. As liquid solvents there may be mentioned aromatic compounds such as xylene, toluene or alkylnaphthalene, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, cyclohexane or paraffins such as mineral oil fractions, mineral oils and vegetable oils Alcohols such as aliphatic hydrocarbons, butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl formamide and dimethyl sulfoxide, Do.

Solid carriers are, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals such as highly disperse silicas, aluminas and silicates . Solid carriers for granules include, for example, granulated and classified natural rocks such as calcite, marble, pumice, hemastone and dolomite, and synthetic granules of inorganic and organic powders, and organics such as sawdust, coconut shells, cornstalks and tobacco stalks. Granules of the material are suitable. Emulsifiers and / or foam-formers include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl Sulfonates and protein hydrolysis products are suitable. As the dispersing agent, for example, lignin-sulfite waste liquid and methyl cellulose are suitable.

Tackifiers such as natural and synthetic polymers in the form of powders, granules or emulsions such as carboxymethylcellulose, gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids such as cephalin and lecithin, Lt; / RTI > As other additives, mineral oil and vegetable oil may be used.

Inorganic pigments such as iron oxide, titanium oxide and prussian blue and dyes such as organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes and micronutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc Can be used.

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

In the case of weeding, the active compounds according to the invention, either by themselves or in the form of preparations, can be used as mixtures with known herbicides, as final preparations or as possible tank mixtures.

Suitable herbicides for the mixtures are known herbicides such as acetochlorine, acifluorfen (-sodium), aclomiphene, alachlor, alloxydim (-sodium), amethrin, amidoclor, amidosulfuron, But are not limited to, anilofos, asulam, atrazine, azaphenidine, azimesulfuron, benzazoline, benzpresate, benzofurone (-methyl), benzazone, benzophenone, benzoylpropyl But are not limited to, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, antioxidants, ), Chloromethoxyphene, chloramben, chloridazone, chlorimuron (-ethyl), chlorinitrophen, chlorsulfuron, chlortholuron, neomethylin, cynosulfuron, clethodim, Propargyl), clomazone, clomeprof, clofyralide, clopyral sulfuron (-methyl) 2,4-D, 2,4-DB, 2,4-di (2,4-dihydroxyphenyl), 2,4,6-tetramethyluronium hexafluorophosphate (-Butyl), diclosyl, diethatyl (-ethyl), dipentoxat, diflupenicane, dipropenepoire, dimepuron, dimethanol, diethanolamine, But are not limited to, dipentaerythritol, dipentaerythritol, dipentaerythritol, dipentaerythritol, dipentaerythritol, dipentaerythritol, dymoron, epoprostan, EPTC, esprocar, (-Ethyl), flampprop (-isopropyl), flampropro (-ethyl), etopramine, etophenone, etophene, (-Isopropyl-L), flampprop (-methyl), plazasulfuron, fluazipop (-butyl), flumethsulam, pullrumicol (pentyl) Flumethsulam, (- methyl), fluorenyl (- butyl), fluridol, fluroxy (- ethyl), fluoxetine, (-Methyl), glyphosate (-isopropylammonium), halo (-methyl), pyruvate (-methyl), pyruvate (Methyl), imazamethapyr, imazamox, imazapyr, imazacquin, imazapeth (p-methyl), hexazinone, imazametabenz Isoxanthrone, isoproperone, isoproterone, isophorone, isoxaben, isoxaflutole, isoxapyripop, lactophen, renasil, renuron, MCPA, MCPP, mefenac Meta-cholor, meta-benzthiazuron, metobenzuron, metobromorone, (alpha-) metolachlor, methosulfuram, methoxuron, , Oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, oxadiazole, (Methyl), prometamol, prometamol, prometamol, prometamol, prometamol, promefuran, promefuran, promefuran, (-Ethyl), pyrazolate, pyrazosulfuron (-ethyl), pyrazosulfuron (-ethyl), pyrazole, pyrazosulfuron (-Methyl), pyrithiobate (-sodium), quinclorac, quenemac, quinoclamine, quizalofop (-), pyriproxyfen, P-ethyl), quizalofop (-P-terfuryl), limsulfuron, cetoxydim, simajin, cimetriin, sulcotrione, sulphentrazone, (Methyl), sulfosuate, sulfosulfuron, tebutam, tebuturon, tebutyllazine, terbutaline, tenylchlor, thiafluamide, thiazopyr, thiadiazin, Thiocarbonyl, thiobenzyl, thiocarbazyl, thallocoxid, trialkoxydim, triarylate, triasulfuron, tribenulone (-methyl), trichloropyr, tridiphenyl, tripluralin and triplusulfuron.

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

The active compounds may be used as such, in the form of preparations, or in the form of preparations prepared therefrom, for example in the form of ready-to-use solutions, suspensions, emulsions, powders, pastes and granules, in the form of preparations or further dilutions. The active compounds are used in conventional manner, for example in spraying, spraying, atomizing or scattering.

The active compound according to the present invention may be applied before or after germination of the plant. They can be incorporated into the soil before sowing.

The amount of active compound used may vary within a substantial range. This is essentially dependent on the nature of the desired effect. A commonly used amount is from 1 g to 10 kg of active compound per hectare of soil surface, preferably from 5 g to 5 kg.

The formulations and uses of the active compounds according to the invention can be seen from the following examples.

<Production Example>

&Lt; Example 1 &gt;

5.8 g (50 mmol) of 1-methyl-imidazolidin-2-thione, 8.6 g (55 mmol) of 2,4,5-trifluoro-benzonitrile, 7.6 g (55 mmol) A mixture of 50 ml of dimethyl sulfoxide is stirred at 80 占 폚 for 16 hours. Upon cooling, the mixture is poured into an approximately equal volume of a stirred mixture of methylene chloride and water and acidified with 2N hydrochloric acid. The organic phase is separated, washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is digested with diethyl ether and the product obtained as crystals is separated by suction filtration.

This gives 9.5 g (75% of theory) of 1-methyl-3- (4-cyano-2,5-difluoro-phenyl) -imidazolidin-2-thione with a melting point of 143 ° C.

&Lt; Example 2 &gt;

(Subsequent reaction)

A solution of 2.0 g (8 mmol) 1-methyl-3- (4-cyano-2,5-difluoro-phenyl) -imidazolidin-2-thione, 1.8 g (16 mmol) 2.2 g (16 mmol) of potassium carbonate and 50 ml of dimethyl sulfoxide is stirred at 100 &lt; 0 &gt; C for 16 hours. Upon cooling, the mixture is poured into an approximately equal volume of a stirred mixture of methylene chloride and water and acidified with 2N hydrochloric acid. The organic phase is separated, washed with water, dried over sodium sulfate and filtered. The filtrate is concentrated under a water pump vacuum, the residue is dipped in isopropanol and the product obtained as crystals is separated by suction filtration.

1.9 g (68% of theory) of 1-methyl-3- (4-cyano-2- fluoro-5-ethylsulfonyl- amino- phenyl) -imidazolidin- to provide.

Other examples of compounds of formula (I) which may be prepared according to the general description of the preparation process according to the invention analogously to preparative examples 1 to 2 are given in the following table 1.

Table 1: Examples of compounds of formula (I)

The logP values mentioned in Table 1 were determined by HPLC (high performance liquid chromatography) on a reversed phase column (C 18) according to EEC Directive 79/831 Annex V. A8. (Temperature: 43 ° C).

(a) Solvent for measurement in acidic range: 0.1% aqueous phosphoric acid solution, acetonitrile; Linear slope 90% acetonitrile-related trials in 10% acetonitrile are indicated in Table 1 as ^a) .

(b) Solvent for measurement in the neutral range: 0.01 molar phosphate buffer aqueous solution, acetonitrile; Linear slope 90% acetonitrile-related attempts at 10% acetonitrile are indicated in Table 1 ^b) .

Standardization was carried out with non-branched alkane-2-ones (with 3 to 16 carbon atoms) with known logP values (logP values were measured with the help of residence time by linear extrapolation between the two subsequent alkanones ).

The? Max values were measured with the help of a UV spectrum of 200 nm to 400 nm at the maximum of the chromatographic signal.

<Usage example>

<Example A>

Pre-germination test

Solvent: acetone 5 parts by weight

Emulsifier: alkylaryl polyglycol ether 1 part by weight

One part by weight of the active compound is mixed with the specified amount of solvent, a specified amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration to produce the appropriate preparation of active compound.

Sprinkle the seeds of the test plant on the normal soil. After about 24 hours, the formulation of active compound is sprayed onto the soil so that in each case the amount of active compound desired per unit area is applied. The concentration of the spray mixture is chosen so that the amount of active compound desired in each case is 1000 l (water) / ha.

After 3 weeks, the degree of damage to the plant is graded as percent damage by comparison with the occurrence of the untreated control.

The definition of a number is as follows:

0% = no effect (same as untreated control)

100% = complete killing

In this test, for example, the compounds of Preparation Examples 2, 5, 8, 9, 10, 11 and 12 are combined in some cases with good tolerance by, for example, crop plants such as maize, .

<Example B>

Germination test

Solvent: acetone 5 parts by weight

Emulsifier: alkylaryl polyglycol ether 1 part by weight

One part by weight of the active compound is mixed with the specified amount of solvent, a specified amount of emulsifier is added, and the concentrate is diluted with water to the desired concentration to produce the appropriate preparation of active compound.

Spray the formulation of the active compound to a test plant of 5-15 cm in height, so that in each case the amount of active compound desired per unit area is applied. The concentration of the spray mixture is chosen so that the amount of active compound desired in each case is 1000 l (water) / ha.

After 3 weeks, the degree of damage to the plant is graded as percent damage by comparison with the occurrence of the untreated control.

The definition of a number is as follows:

0% = no effect (same as untreated control)

100% = complete killing

In this test, for example, the compounds of Preparation Examples 2, 8, 9, 10 and 12 show, in some cases, a strong action against weeds, combined with good tolerance of, for example, crop plants such as barley.

Claims (9)

Substituted 1,3-diaza-2- (thio) oxo-cycloalkane of formula (I) (I) In this formula, 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, R ² represents an optionally substituted monocyclic or bicyclic aromatic group optionally fused to a heterocycle. The method according to claim 1, n represents 1, 2 or 3; Q represents oxygen or sulfur; R ¹ represents hydrogen, formyl, or each of which has 1 to 6 carbon atoms in the alkyl group, and which is optionally substituted with one or more substituents selected from the group consisting of cyano, halogen, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkyl- Alkoxy, alkylamino, dialkylamino, each of which is substituted by C ₁ -C ₄ -alkoxy-carbonyl or morpholinyl, or having 2 to 6 carbon atoms, Alkenyl or alkynyl which is substituted by halogen or C ₁ -C ₄ -alkoxy-carbonyl, or which is substituted by 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 Cycloalkyl or cycloalkylalkyl having from one to four carbon atoms and each of which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkyl; R ² represents an aromatic group shown below; here, R ³ represents hydrogen, nitro, amino, cyano, formylamino or halogen, or each of which has 1 to 6 carbon atoms in the alkyl group and which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy Alkyl, alkoxy, alkylcarbonylamino, alkoxycarbonylamino, alkylaminocarbonylamino, or having 3 to 6 carbon atoms in the cycloalkyl moiety and optionally being substituted with cyano, halogen, C ₁ -C ₄ C ₁ -C ₄ -halogenoalkyl or C ₁ -C ₄ -halogenoalkyl, or is optionally substituted by one or more substituents selected from the group consisting of cyano, nitro, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -halogenoalkyl , C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -halogenoalkoxy; R ⁴ represents hydrogen, nitro, cyano, fluorine, chlorine or bromine; R ⁵ represents nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, hydroxyl, fluorine, chlorine, bromine, or each of which has 4 or fewer carbon atoms and is optionally substituted by fluorine and / or chlorine Alkyl, alkoxy, alkylcarbonyl or alkoxycarbonyl; R ⁶ represents the following group; -A ¹ -A ² -A ³ here, A ¹ is represented by a single bond, or oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the group -NA ⁴ - represents a, wherein A ⁴ is hydrogen, hydroxyl, 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 - alkyl-carbonyl, phenylcarbonyl, C ₁ -C ₄ &Lt; / RTI &gt; alkyl-sulfonyl or phenylsulfonyl, A ¹ is also respectively optionally fluorine, which is substituted by chlorine or bromine, C ₁ -C ₆ - alkanediyl, C ₂ -C ₆ - Al canned yl, C ₂ -C ₆ - aza al canned yl, ₂ C -C ₆ - alkyne diyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - cycloalkenyl denotes a canned one or phenylene, A ² represents a single bond, or oxygen, sulfur, -SO-, -SO ₂ -, -CO- or the group -NA ⁴ - represents a, wherein A ⁴ is hydrogen, hydroxyl, C ₁ -C ₄ - Alkyl, C ₁ -C ₄ -alkoxy, phenyl, C ₁ -C ₄ -alkylsulfonyl or phenylsulfonyl, A ² is optionally fluorine-addition respectively, which is substituted by chlorine or bromine, C ₁ -C ₆ - alkanediyl, C ₂ -C ₆ - Al canned yl, C ₂ -C ₆ - aza al canned yl, ₂ C -C ₆ - alkyne diyl, C ₃ -C ₆ - cycloalkyl alkanediyl, C ₃ -C ₆ - cycloalkenyl denotes a canned one or phenylene, A ³ represents hydrogen, hydroxyl, mercapto, amino, cyano, isocyanato, thiocyanato, nitro, carboxyl, carbamoyl, thiocarbamoyl, sulfo, chlorosulfonyl, fluorine, , Or an alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, alkylthio, alkylsulfonyl, alkylsulfonyl, alkylsulfonyl or alkylsulfonyl group, each of which has 1 to 6 carbon atoms in the alkyl group and is each optionally substituted by fluorine, chlorine or C ₁ -C ₄ -alkoxy , Dialkylamino, alkoxycarbonyl or dialkoxy (thio) phospholyl, or they each have 2 to 6 carbon atoms in the alkenyl, alkylidene or alkynyl group and are each optionally substituted by fluorine or chlorine Alkenyloxy, alkenyloxy, alkenylamino, alkylideneamino, alkenyloxycarbonyl, alkynyl, alkynyloxy, alkynylamino or alkynyloxycarbonyl, or represents a cycloalkyl group C ₁ -C ₄ -alkyl and / or C ₁ -C ₄ -alkoxy, each of which has from 3 to 6 carbon atoms and, if appropriate, from 1 to 4 carbon atoms in the alkyl group and which is optionally substituted with one or more substituents selected from fluorine, chlorine, cyano, carboxyl, Cycloalkyloxy, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylideneamino, cycloalkyloxycarbonyl or cycloalkylalkoxycarbonyl, each optionally substituted with one or more substituents selected from the group consisting of nitro, no, carboxyl, fluorine, chlorine, bromine, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkyloxy, C ₁ -C ₄ - halogenoalkyl oxy and / or C ₁ -C ₄ - alkoxy-carbonyl which is substituted by phenyl, phenoxy, phenyl -C ₁ -C ₄ - alkyl, phenyl -C ₁ -C ₄ - alkoxy, phenoxy-carbonyl or phenyl -C ₁ -C ₄ - alkoxy - represents a carbonyl group, A ³ is also a pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, oxiranyl, oxetanyl, dioxolanyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl , Thiadiazolyl, pyridinyl, pyrimidinyl, triazinyl, pyrazolyl-C ₁ -C ₄ -alkyl, furyl-C ₁ -C ₄ -alkyl, thienyl-C ₁ -C ₄ -alkyl, oxazolyl- C ₁ -C ₄ - alkyl, isoxazol--C ₁ -C ₄ - alkyl, thiazol--C ₁ -C ₄ - alkyl, pyridinyl -C ₁ -C ₄ - alkyl, pyrimidinyl, -C ₁ -C ₄ -Alkyl, pyrazolylmethoxy, furylmethoxy, perhydropyranylmethoxy or pyridylmethoxy, each of which is optionally completely or partially hydrogenated, R ⁷ represents hydrogen, fluorine or chlorine, Or each 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; here, 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 each represents hydrogen, fluorine, chlorine, bromine or C ₁ -C ₄ -alkyl or together represent C ₂ -C ₅ -alkanediyl, R ¹⁰ has a hydrogen, represent a hydroxyl or one to six carbon atoms in each alkyl group and each optionally cyano, fluorine, chlorine, C ₁ -C ₄ - alkoxy, C ₁ -C ₄ - alkyl-carbonyl Alkylcarbonyl, alkoxy-carbonyl or alkylsulfonyl, each of which is substituted by C ₁ -C ₄ -alkoxy-carbonyl or each of which has 2 to 6 carbon atoms and which is optionally substituted with fluorine, chlorine Or alkenyl or alkynyl which is substituted by bromine, or each of which has 3 to 6 carbon atoms in the cycloalkyl group and, if appropriate, 1 to 3 atoms in the alkyl moiety, each optionally substituted by fluorine, chlorine, bromine or C ₁ -C ₄ - which is substituted by alkyl, represent cycloalkyl or cycloalkylalkyl, or who have 6 or fewer carbon atoms and each optionally substituted by each optionally fluorine and / or chlorine, Air in, or represents alkoxy or alkenyloxy, each optionally or cyano, fluorine, chlorine, C ₁ -C ₄ - alkyl, C ₁ -C ₄ - halogenoalkyl, C ₁ -C ₄ - alkoxy or C ₁ Substituted 1,3-diaza-2- (thio) oxo-cycloalkane, characterized in that it represents benzyl or benzyloxy which is substituted by-C ₄ -halogenoalkoxy. The method according to claim 1, n represents 1, 2 or 3; Q represents oxygen or sulfur; R ¹ represents hydrogen, formyl, or methyl, ethyl, n- or i-propyl, n-, i-, or s-, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Butenyl, propynyl or butynyl, each of which is optionally substituted by fluorine or chlorine, or which is optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by halogen; R ² is an aromatic group as shown below: here, R ³ represents hydrogen, nitro, amino, cyano, formylamino, fluorine, chlorine, or represents methyl, trifluoromethyl, acetylamino, propionylamino, butyroylamino, Trifluoromethyl, trifluoromethyl, trifluoroacetylamino, methoxycarbonylamino, ethoxycarbonylamino, methylaminocarbonylamino, ethylaminocarbonylamino, cyclopropylcarbonylamino or phenylcarbonylamino (benzoylamino); R ⁴ represents hydrogen, fluorine or chlorine; R ⁵ represents cyano, thiocarbamoyl, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy or trifluoromethoxy; R ⁶ represents the following group: -A ¹ -A ² -A ³ here, A ¹ represents a single bond or represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or group -NA ⁴ -, wherein A ⁴ represents hydrogen, hydroxyl, methyl, Or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl or ethylsulfonyl, A ¹ is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane- 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne- A ² represents a single bond or represents oxygen, sulfur, -SO-, -SO ₂ -, -CO- or group -NA ⁴ -, wherein A ⁴ is hydrogen, hydroxyl, methyl, Or represents i-propyl, methoxy, ethoxy, n- or i-propoxy, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl or phenylsulfonyl, A ² is also methylene, ethane-1,1-diyl, ethane-1,2-diyl, propane-1,1-diyl, propane-1,2-diyl, propane- 2-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl, propyne-1,2-diyl or propyne- A ³ represents hydrogen, hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine, or methyl Propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i- n-, i-, s- or t-butyloxy, methylthio, ethylthio, n- or i-propylthio, n-, Or methylthio, ethylamino, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, -Propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethoxyphosphoryl, Diethoxyphosphoryl or dipropoxyphosphoryl, diisopropoxyphosphor Butenyl, propenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butyrylideneamino, propenyl, which is optionally substituted by fluorine or chlorine, Butynyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy, propynylamino, butynylamino, propynyloxycarbonyl or butynyloxycarbonyl, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy, cyclopentyloxy or cyclohexyloxy which is substituted by fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl , Cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclo Cyclopentyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or represents a cyclohexylmethoxycarbonyl group or a cyclohexylmethoxycarbonyl group, or a cyclohexylmethoxycarbonyl group, or a cyclohexylmethoxycarbonyl group, Are each independently selected from the group consisting of nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Phenyloxy, benzyl, phenylethyl, benzyloxy, phenyloxycarbonyl, benzyloxycarbonyl, which is substituted by trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl, A ³ is also a pyrrolyl, pyrazolyl, imidazolyl, triazolyl, furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl , Triazinyl, pyrazolylmethyl, furylmethyl, thienylmethyl, oxazolylmethyl, isoxazolylmethyl, thiazolmethyl, pyridinylmethyl, pyrimidinylmethyl, pyrazolylmethoxy, furylmethoxy or pyridylmethoxy Optionally hydrogenated in whole or in part; R ⁷ represents hydrogen, fluorine or chlorine, Or each 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; here, 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 each represents hydrogen, fluorine, chlorine, methyl or ethyl or together represent ethane-1,2-diyl (dimethylene) R ¹⁰ represents hydrogen, hydroxyl, or methyl, ethyl, or propyl, each optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, acetyl, propionyl, methoxycarbonyl or ethoxycarbonyl propenyl, butynyl, propynyl or butynyl, each of which is optionally substituted by fluorine, chlorine or bromine, in the presence of a suitable base such as n- or i-propyl, n-, i-, s- or t- Or represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each of which is optionally substituted by fluorine, chlorine, bromine, methyl or ethyl Or represents methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, propenyloxy or butenyloxy, each of which is optionally substituted by fluorine and / or chlorine Or, respectively, Which is characterized in that it represents benzyl or benzyloxy which is unsubstituted or substituted by halogen, cyano, fluorine, chlorine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy. &Lt; / RTI &gt; 1,3-diaza-2- (thi) oxo-cycloalkane. The method according to claim 1, n represents 1 or 2; Q represents oxygen or sulfur; R ¹ represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy; R ² represents the following aromatic group: here, 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 following group: -A ¹ -A ² -A ³ here, A ¹ represents a single bond, A ² represents a single bond, A ³ is methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl or tert-butyl, each of which represents hydroxyl, amino, cyano, nitro, carboxyl, carbamoyl, sulfo, fluorine, chlorine, bromine or is optionally substituted by fluorine, chlorine, methoxy or ethoxy n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy, ethoxy, n- or i- , i-, s- or t-butoxy, n-, i-, s- or t-pentyloxy, methylthio, ethylthio, n- or i- Propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n- or i-propylsulfinyl, Amino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, Lt; / RTI &gt; unsubstituted or substituted by chlorine, such as propenyl, butenyl, Butenyloxy, butenyloxy, propenylamino, butenylamino, propylideneamino, butylidenamino, propenyloxycarbonyl, butenyloxycarbonyl, propynyl, butynyl, propynyloxy, butynyloxy , Each of which may be optionally substituted with one or more substituents selected from fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxycarbamoyl, Cyclobutyloxy, cyclopentyloxy, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, cyclohexylmethoxy, Cyclohexyloxycarbonyl, cyclopentylmethoxycarbonyl or cyclohexylmethoxycarbonyl, or is optionally substituted with one or more substituents each independently selected from 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 phenoxy, benzyloxy, phenyloxycarbonyl or benzyloxycarbonyl; Substituted 3, 4-diaza-2- (thio) oxo-cycloalkane, characterized in that R &lt; ⁷ &gt; represents hydrogen. The method according to claim 1, n represents 1 or 2; Q represents oxygen or sulfur; R ¹ represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy; R ² represents the following aromatic group: here, 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 following group: -A ¹ -A ² -A ³ here, A ¹ represents the group -NA ⁴ -, wherein A ⁴ represents hydrogen, methylsulfonyl or ethylsulfonyl, A ² represents a single bond or -CO-, A ³ represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i- Or each of which may be optionally substituted with one or more substituents selected from the group consisting of fluorine, chlorine, cyano, carboxyl, methyl, ethyl, n- or i-propyl, methoxy, Cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopropylmethyl, cyclopentylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclohexylmethyl, , Cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy Or each of which may be optionally substituted with one or more substituents selected from nitro, cyano, carboxyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i- Phenoxy, benzyl or benzyloxy, which is substituted by fluoromethoxy, trifluoromethoxy, methoxycarbonyl and / or ethoxycarbonyl; Substituted 3, 4-diaza-2- (thio) oxo-cycloalkane, characterized in that R &lt; ⁷ &gt; represents hydrogen. The method according to claim 1, n represents 1 or 2; Q represents oxygen or sulfur; R ¹ represents methyl, ethyl, n- or i-propyl, each of which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy; R ² represents the following aromatic group: here, 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 following group: -A ¹ -A ² -A ³ here, A ¹ represents the group -NA ⁴ -, wherein A ⁴ represents hydrogen, methylsulfonyl or ethylsulfonyl, A ² represents -SO ₂ -, A ³ represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each of which is optionally substituted by fluorine, chlorine, methoxy or ethoxy, Cyclobutyl, cyclopentyl, or cyclohexyl, each of which is optionally substituted with fluorine, chlorine, cyano or methyl, or is optionally substituted with one or more substituents each independently selected from nitro, cyano, fluorine, chlorine, bromine, Benzyl, which is unsubstituted or substituted by methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, methoxycarbonyl or ethoxycarbonyl; Substituted 3, 4-diaza-2- (thio) oxo-cycloalkane, characterized in that R &lt; ⁷ &gt; represents hydrogen. Diaza-2- (thio) oxo-cycloalkane of formula (II) is reacted, if appropriate, with a halogen compound of formula (III) in the presence of a reaction aid and, if appropriate, in the presence of a diluent, A process for the preparation of a substituted 1,3-diaza-2- (thio) oxo-thiazole derivative according to any one of claims 1 to 6, characterized by carrying out an electrophilic or nucleophilic substitution reaction in the customary manner within the definition. Method for producing cycloalkane: &Lt; RTI ID = 0.0 & (III) X ¹ -R ² In this formula, n, Q, R ¹ and R ² are as defined in any one of claims 1 to 6, X ¹ represents halogen. A herbicidal composition, characterized in that it comprises at least one substituted 1,3-diaza-2- (thio) oxo-cycloalkane according to any one of claims 1 to 6. Use of at least one substituted 1,3-diaza-2- (thio) oxo-cycloalkane according to any one of claims 1 to 6 for the removal of unwanted plants.