DE10028687A1 - New benzoyl substituted thio-cyclohexenone derivatives useful as herbicides, especially for weed control in crops - Google Patents

Abstract

Benzoyl-substituted thio-cyclohexenone derivatives (I) are new. Benzoyl-substituted thio-cyclohexenone derivatives of formula (I) (including the tautomers and stereoisomers) and their salts and metal coordinated derivatives are new: n = 0-2; A = single bond or 1-6C alkylene; R<1> = H; phenyl; or 1-6C alkyl optionally substituted with CN, halo, 1-4C alkoxy or 1-4C alkylthio; R<2> = H or 1-6C alkyl optionally substituted with CN, halo, 1-4C alkoxy or 1-4C alkylthio; or R<1> + R<2> = 1-6C alkylene or R<1> and R<2> on the same C atom together form oxo; R<3>+ R<4> = H; NO2; CN; COOH; CONH2; CSNH2; halo; or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, NH(alkyl), N(alkyl)2 or (alkyl)2NSO2- (each with 1-6C in alkyl and each optionally substituted with CN, halo or 1-4C alkoxy; Y = H; 1-10C alkyl optionally substituted with CN, halo or 1-4C alkoxy; alkenyl or alkenyl (each with 2-10C and each optionally substituted with CN, halo, 1-4C alkyl-CO- or 1-4C alkoxy-CO-); or 6-10C ary l or 6-10C aryl-Alk (each optionally substituted with NO2, NH2, CN, COOH, CONH2, CSNH2, halo, 1-4C alkyl, 1-4C alkoxy, 1-4C alkylthio, 1-4C alkylsulfinyl or 1-4C alkylsulfonyl (each optionally substituted with halo), 1-4C alkoxy-1-4C alkyl, 1-4C alkyl-CO-, 1-4C alkoxy-CO-, 1-4C alkyl-CO-NH-, 1-4C alkoxy-CO-NH- or 1-4C alkyl-SO2-NH-); Alk = alkyl optionally with 1-4C; Z = optionally substituted 4-12 membered, saturated or unsaturated, mono- or bicyclic heterocycle with 1-4 hetero atoms (1-4N and/or 1 O or S, SO or SO2) and optionally substituted with 1-3 oxo or thioxo. An Independent claim is also included for the preparation of compounds (I).

Description

The invention relates to new substituted benzoylcyclohexenones, processes for their Production and their use as herbicides.

It is already known that certain substituted benzoylcyclohexanediones have herbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A- 186 118, EP-A-186 119, EP-A-186 120, EP-A-319 075, WO-A-96/26200, WO-A- 97/46530, WO-A-99/07688, WO-A-00/05221).

The effect of these compounds however, is not satisfactory in all respects.

The new substituted benzoylcyclohexenones of the formula (I)

in which
n represents the numbers 0, 1 or 2,
A stands for a single bond or for alkanediyl (alkylene) with 1 to 6 carbon atoms,
R ^{1 represents} hydrogen, phenyl or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio,
R ^{2 represents} hydrogen or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio, or together with R ^{1 represents} alkanediyl (alkylene) having 1 to 6 carbon stands for atoms, or together with R ¹ - in this case bound to the same carbon atom - and the carbon atom to which R ¹ and R ^{2 are} then bound represents a (C = O) grouping,
R ³ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 6 carbon atoms in the alkyl groups,
R ⁴ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 6 carbon atoms in the alkyl groups, and
Y for hydrogen, for alkyl with 1 to 10 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each given by cyano, halogen, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ -Alkoxy carbonyl-substituted alkenyl or alkynyl each having 2 to 10 carbon atoms, or for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ halo alkyl , C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ -halogen alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ - alkyl-carbonyl, C ₁ -C ₄ alkoxy carbonyl, C ₁ -C ₄ alkylcarbonylamino, C ₁ - C ₄ alkoxycarbonylamino, C ₁ -C ₄ alkylsulfonylamino substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the Alkyl part stands,
Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which has 1 to 4 heteroatoms (up to 4 nitrogen atoms and optionally - alternatively or additively - an oxygen atom or a sulfur atom, or one Contains SO group or an SO _{2 group} ), and which additionally contains one to three oxo groups (C = O) and / or thioxo groups (C = S) as constituents of the heterocycle,
- including all possible tautomeric and possibly possible stereo isomeric forms of the compounds of the general formula (I), and of the possible salts or metal-coordinated derivatives of the compounds of the general formula (I) - found.

In the definitions are the hydrocarbon chains, such as alkyl or alkanediyl - Also in conjunction with heteroatoms, such as in alkoxy - each straight-chain or branches.

Preferred meanings of the radicals or groupings present in the formulas listed above and below are defined below.
n is preferably the number 0 or 2.
A preferably represents a single bond or alkanediyl (alkylene) having 1 to 4 carbon atoms.
R ¹ preferably represents hydrogen, phenyl or alkyl having 1 to 5 carbon atoms which is optionally substituted by cyano, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkylthio.
R ² preferably represents hydrogen or optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio substituted alkyl with 1 to 5 carbon atoms, or together with R ¹ for alkanediyl (alkylene) with 1 to 5 carbon atoms.
R ³ preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy or dialkylaminosulfonyl each having 1 to 5 carbon atoms in the alkyl groups.
R ⁴ preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thio carbamoyl, halogen, or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy or dialkylaminosulfonyl each having 1 to 5 carbon atoms in the alkyl groups.
Y preferably represents hydrogen, alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each in each case optionally by cyano, halogen, C ₁ -C ₄ alkylcarbonyl or C ₁ - C _4- alkoxy-carbonyl substituted alkenyl or alkynyl each having 2 to 6 carbon atoms, or for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl , C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ - C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ -alkyl-carbonyl, C ₁ -C ₄ alkoxy carbonyl, C ₁ -C ₄ alkylcarbonylamino, C ₁ -C ₄ alkoxycarbonylamino, C ₁ -C ₄ alkylsulfonylamino substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbons atomic in the alkyl part.
Z preferably represents one of the heterocyclic groupings below

wherein in each case the bond shown in dashed lines is a single bond or a double bond, and wherein each heterocycle preferably carries only two substituents of the definition R ⁵ and / or R ⁶ in any combination.
Q represents oxygen or sulfur,
R ⁵ for hydrogen, hydroxy, mercapto, cyano, halogen, for each ge optionally by cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkyl thio, C ₁ -C ₄ alkylsulfinyl or C ₁ - C ₄ -alkylsulfonyl-substituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl each having up to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen-substituted alkylamino or dialkylamino each having up to 6 carbon atoms in the alkyl groups, for alkenyl, alkynyl, alkenyloxy, alkenylthio, alkynylthio or alkenylamino, each optionally substituted by halogen, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, optionally substituted by halogen Cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl groups and given Is up to 4 carbon atoms in the alkyl part, or represents phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, optionally substituted by halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, for pyrrolidino , Piperidino or morpholino, or - in the event that two adjacent radicals R ⁵ and R ⁵ are on a double bond - together with the adjacent radical R ^{5 also represents} a benzo group, and
R ^{6 represents} hydrogen, hydroxyl, amino, alkylidene amino with up to 4 carbon atoms, for alkyl, alkoxy, alkylamino, dialkyl amino or alkanoylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms in the alkyl groups, for alkenyl, alkynyl or alkenyloxy optionally substituted by halogen, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkyl alkyl or cycloalkylamino, each optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally to to 3 carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted by halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, or together with an adjacent radical R ⁵ or R ⁶ for GE if necessary by Halogen or C ₁ -C ₄ alkyl substituted alkane diyl having 3 to 5 carbon atoms,
where the individual radicals R ⁵ and R ⁶ - if several of them are bound to the same heterocyclic groupings, may have the same or different meanings within the scope of the above definition.
n particularly preferably stands for the number 0.
A particularly preferably represents a single bond or methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl).
R ¹ particularly preferably represents hydrogen, phenyl or, if appropriate, methyl, ethyl, n- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio or i-propyl, n-, i- or s-butyl.
R ² particularly preferably represents hydrogen or in each case methyl, ethyl, n- or i- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio Propyl, n-, i- or s-butyl, or together with R ¹ for methylene, ethylidene (ethane-1,1-diyl), dimethylene (ethane-1,2-diyl), propylidene (propane-1,1- diyl) or trimethylene (propane-1,3-diyl).
R ³ particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio , Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n - or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
R ⁴ particularly preferably represents hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or, if appropriate, in each case by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio , Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylamino, ethylamino, n - or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, dimethylaminosulfonyl or diethylaminosulfonyl.
Y particularly preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i-, s- substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. or t-butyl, for in each case optionally substituted by cyano, fluorine, chlorine, bromine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl , or for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxymethyl, ethoxy methyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, di-fluoromethoxy, trifluoromethoxy, methylthio, ethyl thio, n- or i Propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, Tr ifluormethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, acetylamino, propionylamino, methoxycarbonylamino, ethoxy carbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfyl, n- or i-propylsulfyl Benzyl or phenylethyl.
Z particularly preferably represents one of the heterocyclic groupings below

Q preferably represents oxygen,
R ⁵ preferably represents hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t -Butoxy, methyl thio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio , Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl, for methylamino, ethylamino , n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, for each ethenyl optionally substituted by fluorine and / or chlorine, Propenyl, butenenyl, ethynyl, propynyl, butynyl, prope nyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthyl, cyclobutylthio, cyclobutylthio, cyclobutylthio, cyclobutylthio, cyclobutylthio, cyclobutylthio , cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclo butylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl, methoxy, methoxy cyclobutylmethoxy, cyclopentylmethoxy, cyclohexyl, cyclopropylmethylthio, Cyclobutylmethylthio, cyclo pentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, Cyclobutylmethylamino, cyclopentylmethylamino or cyclohexyl-methylamino, or represents in each case optionally fluorine- , Chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy , Benzylthio or benzylamino, or - in the event that two adjacent radicals R ⁵ and R ⁵ are located on a double bond - together with the adjacent radical R ⁵ also for a benzo group,
R ⁶ preferably represents hydrogen, hydroxyl, amino, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, which is optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, Ethoxy, n- or i-propoxy, methylamino, ethylamino or dimethyl amino, for ethenyl, propenyl, ethynyl, propynyl or propenyloxy, each optionally substituted by fluorine and / or chlorine, for cyclopropyl, cyclobutyl, each optionally substituted by fluorine and / or chlorine , Cyclopentyl, cyclohexyl, cyclopropyl methyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexyl methyl, or for each optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, Ethoxy, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R ⁵ or R ⁶ for propane-1,3-diyl (trimethylene), butane-1,4 which is optionally substituted by methyl and / or ethyl -diyl (tetramethylene) or pentane-1,5-diyl (P entamethylene).
A very particularly preferably represents a single bond or methylene.
R ¹ very particularly preferably represents hydrogen, phenyl or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine.
R ² very particularly preferably represents hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine, or together with R ^{1 represents} methylene or dimethylene.
R ³ very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio which is optionally substituted by fluorine, chlorine, methoxy or ethoxy , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethyl sulfonyl, methylamino, ethylamino, dimethylamino or dimethylamino sulfonyl.
R ⁴ very particularly preferably represents hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methylthio which is optionally substituted by fluorine, chlorine, methoxy or ethoxy , Ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethyl sulfonyl, methylamino, ethylamino, dimethylamino or dimethylamino sulfonyl.
Y very particularly preferably represents hydrogen, in each case optionally methyl, ethyl, n- or i-propyl, n-, i-, s substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy - or t-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine, chlorine or bromine, or for each optionally substituted by nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i- Propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, di-fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, acetylamino, propionylylamino, methoxycarbonylylamino, methoxycarbonylylamino, methoxycarbonylamino, methoxycarbonylylamino, methoxycarbonyl yl or benzyl.
Z very particularly preferably represents the heterocyclic groupings below

R ⁵ particularly preferably represents hydrogen, fluorine, chlorine, bromine, in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyl, ethyl, n - or i- propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i-propylthio, n- , i- or s-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, for methyl amino, ethylamino, n- or i-propylamino, n-, i- or s -Butylamino, dimethylamino or diethylamino, for ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, each optionally substituted by fluorine and / or chlorine, for cyclopropyl, cyclopropyloxy, cyclopropylthio, each optionally substituted by fluorine and / or chlorine , Cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, C yclopropylmethylthio or cyclopropylmethylamino.
R ⁶ particularly preferably stands for hydrogen, for amino, for each methyl, ethyl, methoxy, ethoxy, methylamino or ethyl amino, optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, for dimethylamino, or for each optionally by fluorine and / or chlorine-substituted cyclopropyl, cyclopropylmethyl, phenyl or benzyl, or together with an adjacent radical R ⁵ or R ⁶ for propane-1,3-diyl (trimethylene), butane-1,4 which is optionally substituted by methyl and / or ethyl -diyl (tetra methylene) or pentane-1,5-diyl (pentamethylene).
R ¹ most preferably represents hydrogen.
R ² most preferably represents hydrogen.
R ³ most preferably represents chlorine, trifluoromethyl or methoxy.
R ⁴ most preferably represents chlorine, trifluoromethyl or methyl sulfonyl.
R ⁵ very particularly preferably represents hydrogen, methyl or ethyl.
R ⁶ very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl.
R ⁵ most preferably represents hydrogen.
R ⁶ most preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl.

The invention preferably also relates to sodium, potassium, magnesium, calcium, ammonium, C ₁ -C ₄ alkyl ammonium, di (C ₁ -C ₄ alkyl) ammonium, tri ( C ₁ -C ₄ alkyl) ammonium, tetra (C ₁ -C ₄ alkyl) ammonium, tri (C ₁ -C ₄ alkyl) sulfonium, C ₅ or C ₆ cycloalkyl ammonium and di (C ₁ -C ₂ alkyl) benzyl ammonium salts of compounds of the formula (I) in which A ¹ , A ² , R ¹ , R ² , R ³ , R ⁴ and R ^{5 are} the have the meanings given above, or also complex compounds (coordination compounds) of these compounds with metals such as copper, iron, cobalt, nickel.

Those compounds of the formula (I) are preferred according to the invention which is a combination of the meanings listed above as preferred is present.

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

According to the invention, those compounds of the Formula (I), in which a combination of the above is particularly preferred added listed meanings is present.

Most preferred according to the invention are those compounds of the formula (I), in which a combination of the above is most preferred listed meanings is present.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.  

The position of the radicals R ¹ , R ² , R ³ , R ⁴ and AZ can vary according to formula (I).

The radical R ³ is preferably located in position (4) on the phenyl ring, particularly preferably in position (2).

The radical R ⁴ is preferably found in position (4) on the phenyl ring when the radical R ³ is in position (2).

The rest AZ is preferably found in position (2) on the phenyl ring, particularly preferably in position (3), the substitution pattern (2) -R ³ , (4) -R ⁴ and (3) -AZ being particularly preferred.

The compounds of the general formulas (IA), (IB) and (IC) below are very particularly the subject of the present invention.

n, A, R ¹ , R ² , R ³ , R ⁴ , Y and Z in the general formulas (IA), (IB) and (IC) each have the meanings given in the preceding definitions.

The compounds of the general formulas (IA), (IB) and (IC), in which A for Methylene is particularly noteworthy.

Examples of the compounds of the general formula (I) according to the invention are listed in the groups below.

Group 1

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given in the table below:

Group 2

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 1.

Group 3

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 1.

Group 4

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 1.

Group 5

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 1.

Group 6

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given in the table below:

Group 7

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 6.

Group 8

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 6.

Group 9

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 6.

Group 10

R ³ , R ⁴ , R ⁵ and R ⁶ have, for example, the meanings given above in Group 6.

The new substituted benzoylcyclohexenones of the formula (I) are notable for strong and selective herbicidal activity.

The new substituted benzoylcyclohexenones of the formula (I) are obtained if substituted cyclohexanediones of the formula (II)

in which
A, R ¹ , R ² , R ³ , R ⁴ and Z have the meaning given above,
with a halogenating agent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and reacting the halocyclohexenones of the formula (III) obtained in this (in the first reaction stage)

in which
A, R ¹ , R ² , R ³ , R ⁴ and Z have the meaning given above,
- after intermediate insulation or without intermediate insulation ("in situ") -
in a second reaction step with mercapto compounds of the formula (IV)

HS-Y (IV)

in which
Y has the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carrying out the compounds of the formula (I) thus obtained as part of the definition of the substituent in a customary manner, electrophilic or nucleophilic substitution reactions or oxidation or reduction reactions or converting the compounds of the formula (I) into salts in the customary manner.

If, for example, 2- [4-chloro-2 - [(3,4-dimethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl) methyl] benzoyl] is used -cyclohexane-1,3-dione and phosgene and then thiophenol as starting materials, the course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the substituted benzoyl cyclohexanediones to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), A, R ¹ , R ² , R ³ , R ⁴ and Z preferably have those meanings which are particularly preferred above, in connection with the description of the compounds of the general formula (I) according to the invention, particularly preferred , very particularly preferred or most preferred for A, R ¹ , R ² , R ³ , R ⁴ and Z have been given.

The starting materials of the general formula (II) are known and / or can be according to known processes can be produced (cf. WO-A-00/05221).

The process according to the invention for the preparation of the compounds of the general Formula (I) is used in the first stage of implementation using a halo Genetic agent carried out. It can be the usual halogenation  agents are used to convert enols into corresponding ones Halogenalkenes are suitable. Halogen is preferably fluorine or chlorine or bromine, especially for chlorine. It is therefore preferably chlorinating agents or brominating agent used. These preferably include phosgene, oxal acid dichloride, oxalic acid dibromide, phosphorus (III) chloride, phosphorus (III) bromide, Phosphoryl chloride, thionyl chloride and thionyl bromide.

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably used in the first reaction stage using a Reaction auxiliary carried out. Here come those for halogenation reactions usual reaction aids into consideration. These preferably include Acetonitrile, N, N-dimethyl-formamide, N, N-diethyl-formamide, N, N-dipropyl-form amide and N, N-dibutyl-formamide and N-methyl-pyrrolidone.

The process according to the invention for the preparation of compounds of all general formula (I) mercaptover to be used as starting materials Bonds are generally defined by the formula (IV). In the general formula (IV), Y has in particular the meaning which has already been mentioned above in Zu connection with the description of the compounds of the invention my formula (I) as preferred, particularly preferred or very particularly before given for Y has been specified.

The starting materials of the general formula (IV) are known organic synthesis chemicals.

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably used in the second reaction step carried out a reaction aid. Here come as reaction aids generally the usual inorganic or organic bases or acid acceptors into consideration. These preferably include alkali metal or alkaline earth metal, acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or  alkanolates, such as sodium, potassium or calcium acetate, lithium, Sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, Sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropyl amine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4- Methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5- Ethyl 2-methyl pyridine, 4-dimethylamino pyridine, N-methyl piperidine, 1,4-diaza bicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1.8 Diazabicyclo [5,4,0] -undec-7-ene (DBU).

The first and the second stage of the production process according to the invention of the compounds of the general formula (I) are preferably obtained using Ver using diluents. Come as a diluent inert organic solvents in particular. This includes ins special aliphatic, alicyclic or aromatic, optionally halogenated Hydrocarbons, such as gasoline, benzene, toluene, xylene, chlorobenzene, Dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, tetra chlorinated carbon; 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-methyl-pyrrolidone or hexamethylphosphoric triamide; Esters such as acetic acid methyl ester or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether or Ethylene glycol monoethyl ether.  

The reaction temperatures can be carried out when carrying out the first and the second Stage of the method according to the invention can be varied over a wide range. In general, one works at temperatures between -20 ° C and + 150 ° C preferably between 0 ° C and 120 ° C.

The process according to the invention is generally carried out in both stages Normal pressure carried out. However, it is also possible to use the Ver drive under increased or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the process according to the invention, the starting materials in generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The Reaction is generally carried out in a suitable diluent were suitable reaction auxiliaries carried out and the reaction mixture is generally stirred for several hours at the required temperature. The on work is carried out according to customary methods (cf. games).

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

The active compounds according to the invention can, for. B. be used in the following plants:
Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senania, Sesola , Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, Cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture  areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You let yourself optionally also as intermediates or precursors for the synthesis of further Use active ingredients.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by biotechnological and; genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including those that can or cannot be protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as shoot, leaf, flower and root understood with leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops as well as vegetative and generative Propagation material, for example cuttings, tubers, rhizomes, offshoots and Seeds.  

The treatment of plants and parts of plants according to the invention with the Active substances take place directly or by influencing their environment, living space or storage room according to the usual treatment methods, e.g. B. by diving, Spraying, vaporizing, atomizing, scattering, spreading and when propagating material, especially in the case of seeds, continues with one or more layers Envelop.

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient im impregnated natural and synthetic materials as well as very fine encapsulation in polymers Fabrics.

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

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont  morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam Generating funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates as well as protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite leach and methyl cellulose.

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

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

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control ver can be used, whereby ready formulations or tank mixes are possible. It  So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin (-ethyl), Benfuresate, Bensulf uron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifemox, bispyribac (-sodium), bromobutide, bromofenoxime, Bromoxynil, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cini don (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (- propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Cloran sulam (-methyl), cumyluron, cyanazines, cybutryne, cycloates, cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichloroprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimetha metryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P- ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumetsulam, Fluo meturon, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyr sulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxy propyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fome safen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropyl- ammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones, imaza methabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, Imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin,  Isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotrione, Metamitron, Metaza chlorine, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Para quat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, pico linafen, Piperophos, Pretilachlor, Primisulfuron (-methyl), Profluazol, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Procarbazone (-sodium), Propyz amides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolates, pyrazo sulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyri ftalid, pyriminobac (methyl), pyrithiobac (sodium), quinchlorac, quinmerac, quin oclamine, quizalofop (-P-ethyl, -P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulf uron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, Thiafluamides, Thiazopyr, Thidiazimin, Thifensulhron (-methyl), Thiobencarb, Tio carbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin, trifloxysulfuron, triflusulfisron (-methyl), tritosulfuron.

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

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

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

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples

example 1

A mixture of 1.3 g (3 mmol) of 2- [2,4-dichloro-3 - [(3-methyl-2-oxo-tetrahydro- 1 (2H) pyrimidinyl) methyl] benzoyl] cyclohexane-1,3-dione, 1.0 g (7.5 mmol) oxal acid dichloride, 2 drops of N, N-dimethylformamide and 30 ml of methylene chloride Heated under reflux for 30 minutes and then immersed in a water jet vacuum tight. The residue is taken up in 50 ml of tetrahydrofuran and treated with 0.33 g (3 mmol) of thiophenol. 0.50 g (4.5 mmol) are then added while cooling with ice. Triethylamine added dropwise. After removing the ice cooling, the Mixture stirred for 2 hours at room temperature and then in a water jet vacuum concentrated. The residue is taken up in methylene chloride, once each with 1N hydrochloric acid, water and saturated aqueous sodium chloride solution wash, dry with sodium sulfate and filter. The filtrate is in a water jet concentrated in vacuo, the residue digested with diethyl ether and the crystalline falling product isolated by suction.

0.91 g (61% of theory) of 1- [2,6-dichloro-3 - [(6-oxo-2-phenylthio-1-cyclo hexen-1-yl) -carbonyl] -benzyl] -3-methyl-tetrahydro-2 (1H) -pyrimidinone from Melting point 140 ° C.

Analogous to Example 1 and in accordance with the general description of the manufacturing process according to the invention. for example, the compounds of the general formula (I) - or of the general formula (ID) - listed in Table 1 below can also be prepared.

Table 1

Examples of the compounds of the formula (ID)

The logP values given in Table 1 were determined in accordance with EEC Directive 79/831 Annex V. A8 by HPLC (High Performance Liquid Chromato graphy) 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 - ent Talking 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 using the Retention times through linear interpolation between two consecutive Alkanones).

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

Table 2

Further examples of the compounds of the formula (I)

Examples of use Example A Pre-emergence test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

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

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

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

In this test, for example, the compound according to preparation example 16 shows with good tolerance to crops, such as B. corn, strong Effect against weeds.  

Example B Post emergence test

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

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5- 15 cm have so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied.

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

It means:

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

In this test, for example, the compounds according to the preparation example show 1, 2, 5, 16, 17, 18, 19 and 20, some with good tolerance to culture plants, such as B. corn and wheat, strong action against weeds.

Claims (15)

1. Substituted benzoylcyclohexenones of the formula (I),
in which
n represents the numbers 0, 1 or 2,
A represents a single bond or alkanediyl (alkylene) having 1 to 6 carbon atoms,
R ^{1 represents} hydrogen, phenyl or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ^{2 represents} hydrogen or optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio substituted alkyl having 1 to 6 carbon atoms, or together with R ^{1 represents} alkanediyl (alkylene) having 1 to 6 Stands for carbon atoms, or together with R ¹ - in this case bound to the same carbon atom - and the carbon atom to which R ¹ and R ^{2 are} then bound stands for a (C = O) - grouping,
R ³ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 6 carbon atoms in the alkyl groups,
R ⁴ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 6 carbon atoms in the alkyl groups, and
Y for hydrogen, for alkyl with 1 to 10 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each optionally substituted by cyano, halogen, C ₁ -C ₄ alkylcarbonyl or C ₁ -C ₄ - Alkoxy-carbonyl substituted alkenyl or alkynyl each having 2 to 10 carbon atoms, or for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkylthio, C ₁ - C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkyl carbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkyl-carbonyl-amino, C ₁ - C ₄ alkoxy-carbonyl-amino, C ₁ -C ₄ -alkyl-sulfonyl-amino substitu iertes aryl or arylalkyl having in each case 6 or 10 carbon atoms in the aryl groups and optionally 1 up to 4 carbon atoms in A lkylteil stands, and
Z represents an optionally substituted 4- to 12-membered, saturated or unsaturated, monocyclic or bicyclic, heterocyclic grouping which has 1 to 4 heteroatoms (up to 4 nitrogen atoms and optionally - alternatively or additively - an oxygen atom or a sulfur atom, or contains an SO group or an SO _{2 group} ), and which additionally contains one to three oxo groups (C = O) and / or thioxo groups (C = S) as constituents of the heterocycle,
- Including all possible tautomeric and possibly possible stereoisomeric forms of the compounds of the general formula (I), and of the possible salts or metal-coordinated derivatives of the compounds of the formula (I). 2. Compounds according to claim 1, characterized in that
n represents the numbers 0 or 2,
A represents a single bond or alkanediyl (alkylene) having 1 to 4 carbon atoms,
R ^{1 represents} hydrogen, phenyl or alkyl which has 1 to 5 carbon atoms and is optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio,
R ₂ for hydrogen or optionally substituted by cyano, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkylthio substituted alkyl having 1 to 5 carbon atoms, or together with R ¹ for alkanediyl (alkylene) having 1 to 5 carbon atoms stands,
R ³ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 5 carbon atoms in the alkyl groups,
R ⁴ for hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino or dialkylaminosulfonyl optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy each has 1 to 5 carbon atoms in the alkyl groups,
Y for hydrogen, for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each optionally substituted by cyano, halogen, C ₁ -C ₄ alkylcarbonyl or C ₁ - C ₄ - alkoxy-carbonyl-substituted alkenyl or alkinyl each having 2 to 6 carbon atoms, or represents in each case optionally substituted by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkyl thio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkyl sulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl , C ₁ -C ₄ alkylcarbonylamino, C ₁ -C ₄ alkoxy carbonylamino, C ₁ -C ₄ alkylsulfonylamino substituted aryl or arylalkyl, each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the Alkyl part stands,
Z represents one of the heterocyclic groupings below,
in which the bond shown in dashed lines is a single bond or a double bond, and in which each heterocycle preferably carries only two substituents of the definition R ⁵ and / or R ⁶ in any combination,
Q represents oxygen or sulfur,
R ⁵ for hydrogen, hydroxy, mercapto, cyano, halogen, each optionally with cyano, halogen, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or C ₁ -C ₄ -Alkyl sulfonyl substituted alkyl, alkylcarbonyl, alkoxy, alkoxy carbonyl, alkylthio, alkylsulfinyl or alkylsulfonyl, each with up to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen, alkyl amino or dialkylamino, each with up to 6 carbon atoms in the alkyl groups, for in each case optionally substituted by halogen, alkenyl, alkynyl, alkenyloxy, alkenyl thio, alkynylthio or alkenylamino, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for cycloalkyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, optionally substituted by halogen Cycloalkylalkylthio or cycloalkylalkylamino each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally s up to 4 carbon atoms in the alkyl part, or represents phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, each optionally substituted by halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, represents pyrrolidino, piperidino or morpholino, or - in the event that two adjacent radicals R ⁵ and R ⁵ are on a double bond - also together with the neighboring radical R ^{5 represents} a benzo group, and
R ⁶ for hydrogen, hydroxyl, amino, alkylidene amino with up to 4 carbon atoms, for alkyl, alkoxy, alkylamino, dialkylamino or alkanoylamino, each optionally substituted by halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms in the alkyl groups, for each optionally substituted by halogen-substituted alkenyl, alkynyl or alkenyloxy, each having up to 6 carbon atoms in the alkenyl or alkynyl groups, for each optionally substituted by halogen, cycloalkyl, cycloalkylalkyl or cycloalkylamino, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally up to 3 Carbon atoms in the alkyl part, or for phenyl or benzyl optionally substituted by halogen, C ₁ -C ₄ alkyl or C ₁ -C ₄ alkoxy, or together with a neighboring radical R ⁵ or R ⁶ for optionally by halogen or C ₁ -C ₄ alkyl-substituted alkanediyl having 3 to 5 carbon atoms,
where the individual radicals R ⁵ and R ⁶ - insofar as several of them are bound to the same heterocyclic groupings - can have the same or different meanings in the context of the above definition. 3. Compounds according to claim 1 or 2, characterized in that
A represents a single bond or methylene, ethylidene (ethane-1,1-diyl) or dimethylene (ethane-1,2-diyl),
R ^{1 represents} hydrogen, phenyl or in each case methyl, ethyl, n- or i-propyl substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio , n-, i- or s-butyl,
R ^{2 represents} hydrogen or methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i- or s-butyl, or together with R ¹ for methylene, ethylidene (ethane-1,1-diyl), dimethylene (ethane-1,2-diyl), propylidene (propane-1,1-diyl) or trimethylene (propane-1,3-diyl),
R ^{3 represents} hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or for each methyl optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methyl thio, ethylthio , n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, 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, dimethylaminosulfonyl or diethylaminosulfonyl,
R ^{4 represents} hydrogen, nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, or methyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methyl thio, ethylthio , n- or i-propylthio, n-, i-, s- or t-butylthio, methyl sulfinyl, 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, dimethylaminosulfonyl or diethylaminosulfonyl,
Y for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy , for any given ethenyl, propenyl, butenyl, ethynyl, propynyl or butynyl, optionally substituted by cyano, fluorine, chlorine, bromine, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, or for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, di-fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propyl thio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, Ac ethyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, acetylamino, propionylamino, methoxycarbonylamino, ethoxycarbonylamino, methylsulfonylamino, ethylsulfonylamino, n- or i-propylsulfonylamino-substituted phenyl, phenyl, phenyl, substitutedyl, phenyl ,
Z for one of the heterocyclic groupings below
stands,
Q represents oxygen,
R ⁵ for hydrogen, hydroxy, mercapto, cyano, fluorine, chlorine, bromine, iodine, for each optionally by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy , Methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl substituted methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio; Ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, for methylamino, ethylamino, n - or i- propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, di-n-propylamino or di-i-propylamino, for ethenyl or propenyl which are optionally substituted by fluorine and / or chlorine , Butenenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio, butenylthio, propenylamino or butenylamino, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyl oxy, cyclopentyloxy, cyclo butyloxy, cyclopentyloxy, cyclo butyl oxy, cyclo butyl oxy, cyclo butyl oxy, cyclo butyl oxy, , Cyclo butylthio, Cyclopentylthio, Cyclohexylthio, Cyclopropyl amino, Cyclobutylamino, Cyclopentylamino, Cyclohexyl amino, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentyl methyl, Cyclohexylmethyl, Cyclopropylmethoxy, Cyclobutyl methoxy, Cyclopentylmetho xy, cyclohexylmethoxy, cyclo propylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclo butylmethylamino, cyclopentylmethylamino or cyclohexyl methylamino, or for each optionally by fluorine, chlorine, methyl, i-ethyl, n-, n-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy substituted phenyl, phenyloxy, phenylthio, phenylamino, benzyl, benzyloxy, benzylthio or benzylamino, or - in the event that two adjacent radicals R ⁵ and R ⁵ are on a double bond - together with the adjacent radical R ⁵ also represents a benzo group, and
R ⁶ for hydrogen, hydroxy, amino, for each methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n which is optionally substituted by fluorine and / or chlorine, methoxy or ethoxy - or i-propoxy, methylamino, ethyl amino or dimethylamino, for each optionally substituted by fluorine and / or chlorine, ethenyl, propenyl, ethynyl, propynyl or propenyloxy, for each optionally substituted by fluorine and / or chlorine, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl , Cyclopropylmethyl, Cyclobutyl methyl, Cyclopentylmethyl or Cyclohexylmethyl, or for each optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy-substituted phenyl or benzyl, or together with an adjacent radical R ⁵ or R ^6, each propane-1,3-diyl (trimethylene), butane-1,4-diyl (optionally substituted by methyl and / or ethyl) ( Tetramethylene) or pentane-1-5-diyl (pentamethylene ) stands. 4. Compounds according to any one of claims 1 to 3, characterized in that
A represents a single bond or methylene,
R ^{1 represents} hydrogen, phenyl or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine,
R ^{2 represents} hydrogen or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine, or together with R ^{1 represents} methylene or dimethylene,
R ³ for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methyl thio, ethylthio, which is in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulfonyl,
R ⁴ for hydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, or for methyl, ethyl, n- or i-propyl, methoxy, ethoxy, methyl thio, ethyl thio, which is in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy , Methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methylamino, ethylamino, dimethylamino or dimethylaminosulfonyl,
Y for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy , for propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine, chlorine or bromine, or for in each case optionally by nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, trifluoromethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxy, ethoxy, n- or i-propoxy, di-fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio , Trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, acetylamino, propionylamino, methoxycarbonylamino, ethsulfonylylylamino, methylsulfonylylamino, methyloxylylylamino, or
R ⁵ for hydrogen, fluorine, chlorine, bromine, for each optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- or s-butylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, for methylamino, ethylamino, n- or i-propylamino, n-, i- or s-butylamino , Dimethylamino or Diethyl amino, for each optionally substituted by fluorine and / or chlorine substituted ethenyl, propenyl, butenyl, ethynyl, propynyl, butynyl, propenyloxy, butenyloxy, propenylthio or for cyclopropyl, cyclopropyloxy optionally substituted by fluorine and / or chlorine , Cyclopropylthio, cyclopropylamino, cyclopropylmethyl, cyclopropylmethoxy, cyclopropylmethylt hio or cyclopropyl methylamino, and
R ⁶ for hydrogen, for amino, for methyl, ethyl, methoxy, ethoxy, methylamino or ethylamino, each optionally substituted by fluorine and / or chlorine, methoxy or ethoxy, for dimethylamino, or for cyclopropyl optionally substituted by fluorine and / or chlorine , Cyclopropylmethyl, phenyl or benzyl, or together with an adjacent radical R ⁵ or R ⁶ for propane-1,3-diyl (trimethylene), butane-1,4-diyl (tetramethylene) which is optionally substituted by methyl and / or ethyl or pentane-1-5-diyl (pentamethylene). 5. Compounds according to any one of claims 1 to 4, characterized in that
R ^{1 represents} hydrogen,
R ^{2 represents} hydrogen,
R ^{3 represents} chlorine, trifluoromethyl or methoxy,
R ^{4 represents} chlorine, trifluoromethyl or methylsulfonyl,
R ^{5 represents} hydrogen, methyl or ethyl, and
R ^{6 represents} hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl, cyclopentyl, cyclopentylmethyl, cyclohexyl, cyclohexylmethyl, phenyl or benzyl. 6. Compounds according to any one of claims 1 to 5, characterized in that
R ^{5 represents} hydrogen, and
R ^{6 represents} methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, cyclopropyl, cyclopropylmethyl or phenyl. 7. Compounds according to any one of claims 1 to 6, characterized in that
n stands for the number 0. 8. Compounds according to any one of claims 1 to 7, characterized in that
Z represents one of the groupings below
9. Compounds according to any one of claims 1 to 8, characterized in that
Q stands for oxygen. 10. Compounds of the formula (IA)
wherein n, A, R ¹ , R ² , R ³ , R ⁴ , Y and Z are defined according to any one of claims 1 to 9. 11. Compounds of the formula (IB)
wherein n, A, R ¹ , R ² , R ³ , R ⁴ , Y and Z are defined according to any one of claims 1 to 9. 12. Compounds of the formula (IC)
wherein n, A, R ¹ , R ² , R ³ , R ⁴ , Y and Z are defined according to any one of claims 1 to 9. 13. A process for the preparation of compounds according to any one of claims 1 to 12, characterized in that compounds of the formula (II)
in which
A, R ¹ , R ² , R ³ , R ⁴ and Z are defined according to one of claims 1 to 9,
with a halogenating agent, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and reacting the halogen cyclohexenones of the formula (III) obtained in this way (in the first reaction stage)
in which
A, R ¹ , R ² , R ³ , R ⁴ and Z are defined according to one of claims 1 to 9,
- after intermediate insulation or without intermediate insulation ("in situ") -
in a second reaction step with mercapto compounds of the formula (IV)
HS-Y (IV)
in which
Y has the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently, in the customary manner, on the compounds of the formula (I) thus obtained as part of the definition of the substituent, carry out electrophilic or nucleophilic substitution reactions or oxidation or reduction reactions or convert the compounds of the formula (I) into salts in the customary manner. 14. Herbicidal agents, characterized by the content of at least one Connection according to one of claims 1 to 12 and the usual stretch average. 15. Use of at least one compound according to one of the claims 1 to 12 to control unwanted plants.