WO2011138280A2 - Herbizid-safener-kombinationen enthaltend arylpyridazinone und safener - Google Patents

Herbizid-safener-kombinationen enthaltend arylpyridazinone und safener Download PDF

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WO2011138280A2
WO2011138280A2 PCT/EP2011/056965 EP2011056965W WO2011138280A2 WO 2011138280 A2 WO2011138280 A2 WO 2011138280A2 EP 2011056965 W EP2011056965 W EP 2011056965W WO 2011138280 A2 WO2011138280 A2 WO 2011138280A2
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alkyl
hydrogen
alkoxy
compounds
halogen
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PCT/EP2011/056965
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French (fr)
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WO2011138280A3 (de
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Christopher Hugh Rosinger
Stefan Lehr
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Bayer Cropscience Ag
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
    • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof

Definitions

  • Herbicide-safener combinations containing arylpyridazinones and safeners containing arylpyridazinones and safeners
  • the invention relates to the technical field of pesticides, in particular herbicide-antidote combinations (drug-safener combinations), which are suitable for use against competing harmful plants in crops.
  • WO2007 / 1 19434 and WO 2009/035150 disclose herbicidally active 4-phenylpyridazinones which carry an alkyl or alkoxy radical in the 2-position of the phenyl ring. Furthermore, these documents disclose that these 4-Phenylpyridazinone can be used with safeners and other herbicides.
  • WO2009 / 035145 discloses mixtures of 4-alkyl-substituted aryl-pyridazinones with a further herbicide and safeners.
  • pyridazinones and their mixtures with safener are sometimes not fully compatible with some important crop plants such as e.g. different cereals, corn, rice, cereals or sugarcane. Therefore, they can not be used in some cultures or only in such low application rates that the desired broad herbicidal activity against harmful plants is not guaranteed.
  • This object is achieved by the herbicide-safener combinations according to the invention comprising arylpyridazinones and safeners.
  • the present invention therefore provides herbicide-safener combinations containing 4-phenylpyridazinones of the formula (I) or salts thereof
  • a and B independently of one another are each hydrogen, (C 3 -C 6) -cycloalkyl or (n-C 6) -alkyl substituted by n radicals from the group consisting of halogen, (C 3 -C 6) -cycloalkyl, phenyl and halophenyl, n is 0 , 1, 2 or 3;
  • R 1 represents in each case (C 1 -C 6 ) -alkyl substituted by n halogen atoms, (C 2 -C 6 ) -alkenyl, (C 1 -C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl, di- (C 1 -C 4 ) -alkyl 4) alkoxy (Ci-C 6) alkyl or (dC 4) - alkylthio, (Ci-C 6) alkyl,
  • R 2 represents in each case by n halogen substituted (d-C6) alkyl, (C 2 -C 6) - alkenyl, (Ci-C 4) alkoxy (Ci-C 6) alkyl or di (Ci-C 4 ) -alkoxy- (C 1 -C 6 ) -alkyl,
  • R 3 R 4 and R 5 independently from each other by n halogen atoms substituted (dC 6) alkyl, (dC 4) -alkoxy, N- (Ci-C 6) alkylamino, N, N-di- (d- C 6 ) -alkylamino, (C 1 -C 4 ) -alkylthio, (C 2 -C 4 ) -alkenyl or (C 3 -C 6 ) -cycloalkylthio, or by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) alkoxy-substituted phenyl, benzyl, phenoxy or phenylthio;
  • R 6 and R 7 are each independently hydrogen
  • R 6 and R 7 together with the N-atom to which they are attached form a 3- to 6-membered ring containing 2 to 5 carbon atoms and 0 or 1 oxygen or sulfur atoms;
  • n-substituted (d-C6) alkyl R 8 is (C 2 -Ce) -alkenyl, (C 2 -C 6) alkynyl, (Ci-C 4) alkoxy (Ci-C 6) - alkyl, (C 1 -C 4) -alkyl kylth io- (Ci-C4) -alkyl or di- (Ci-C 4) alkoxy (Ci-C 6) alkyl,
  • n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) - AI koxy-substituted phenyl, phenyl (dC 4) alkyl, heteroaryl, phenoxy (dC 4) alkyl or heteroaryloxy (Ci-C4) -alkyl;
  • halogen is halogen, cyano, nitro, halogeno (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -alkoxy or phenyl substituted by n halogen atoms,
  • halogen is halogen, cyano, nitro or in each case by n halogen atoms substituted (Ci-C 6 ) alkyl, (C 3 -C 6 ) -cycloalkyl, (CrC 6 ) alkoxy or phenyl;
  • Z independently of one another in each case denote hydrogen, halogen, cyano, nitro, (C 3 -C 6) -cycloalkyl or (C 1 -C 6) -alkyl substituted by n halogen atoms, (C 1 -C 6) -alkoxy or phenyl, and
  • herbicide-safener combinations should be excluded, in which the index n is zero and the safener fenchlorazole-ethyl, cloquintocet-mexyl or mefenpyr-diethyl.
  • the herbicide-safener combinations according to the invention may contain additional further components, for example pesticidal active ingredients of a different kind and / or in crop protection customary additives and / or formulation auxiliaries, contain or be used together with them.
  • herbicide (A), 4-phenylpyridazinone (A) and compounds of the formula (I) are to be understood as synonymous.
  • the herbicides (A) and the safeners (B) can be applied in a known manner, for example jointly (for example as a co-formulation or as a tank mixture) or also as a splitting, e.g. on the plants, plant parts, plant seeds or the area on which the plants grow. It is possible, e.g. the use of the single active substances or the herbicide-safener combinations in several portions (sequence application), eg. After pre-emergence applications, followed by post-emergence applications or early post-emergence applications, followed by mid-late post-emergence applications. Preference is given to the joint or timely use of the active ingredients of the respective combination. It is also possible to use the individual active substances or the herbicide-safener combinations for seed treatment.
  • Alkyl is saturated, straight-chain or branched hydrocarbon radicals having 1 to 8 carbon atoms, for example C 1 -C 6 -alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methyl-propyl, 2-methylpropyl, 1, 1-dimethylethyl, Pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3 Methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethy
  • Haloalkyl means straight-chain or branched alkyl groups having 1 to 8 carbon atoms (as mentioned above), in which groups the hydrogen atoms may be partially or completely replaced by halogen atoms, for example C 1 -C 2 haloalkyl, such as chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl , Difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoro- methyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro, 2-difluoroethyl, 2, 2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pen
  • Alkenyl means unsaturated, straight-chain or branched hydrocarbon radicals having 2 to 8 carbon atoms and a double bond in any position, e.g. C2-C6 alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1 - Methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl 1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3 butenyl, 1, 1-dimethyl-2-propenyl, 1,
  • Alkoxy represents saturated, straight-chain or branched alkoxy radicals having 1 to 8 carbon atoms, for example C 1 -C 6 -alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1, 1-dimethylethoxy, pen toxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3 Methylpentoxy, 4-methylpentoxy, 1, 1-dimethylbutoxy, 1, 2 Dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-tri methylpropoxy, 1-ethyl
  • Haloalkoxy means straight-chain or branched alkoxy groups having 1 to 8 carbon atoms (as mentioned above), wherein in these groups some or all of the hydrogen atoms may be replaced by halogen atoms as mentioned above, e.g.
  • d-C2-haloalkoxy such as chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2, 2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro, 2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1, 1, 1 - trifluoroprop-2-oxy.
  • Alkylthio means saturated, straight-chain or branched alkylthio radicals having 1 to 8 carbon atoms, for example C 1 -C 6 -alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, pentylthio , 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3 Methylpentylthio, 4-methylpentylthio, 1, 1-dimethylbutylthio, 1, 2-dimethylbutylthi
  • Heteroaryl means 2-furyl, 3-furyl, 2-thienyl, 3-thienyl, 1-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 3-isothiazolyl, 4-isothiazolyl, 5-isothiazolyl, 1-pyrazolyl, 3-pyrazolyl, 4-pyrazolyl, 5-pyrazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, 1 -imidazolyl, 2- lnnidazolyl 4-imidazolyl, 5-imidazolyl, 1, 2,4-oxadiazol-3-yl, 1, 2,4-oxadiazol-5-yl, 1, 2,4-thiadiazol-3-yl, 1, 2,4 Thiadiazol-5-yl, 1, 3,4-oxadiazol-2-yl, 1, 3,
  • This heteroaryl is in each case unsubstituted or in each case mono- or polysubstituted by identical or different substituents selected from radicals, chlorine, bromine, iodine, cyano, hydroxy, mercapto, amino, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl , sec-butyl, tert-butyl, cyclopropyl, 1-chlorocyclopropyl, vinyl, ethynyl, methoxy, ethoxy, isopropoxy, methylthio, ethylthio, trifluoromethylthio, chlorodifluoromethyl, dichlorofluoromethyl, chlorofluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2.2 , 2-trifluoroethyl, trifluoromethoxy,
  • the compounds of the formula (I) can also be present as geometrical and / or optical isomers or isomer mixtures in different compositions, which can optionally be separated in a customary manner. Both the pure isomers and the isomer mixtures, their preparation and use as well as agents containing them are the subject of the present invention. However, in the following, for the sake of simplicity, reference is always made to compounds of the formula (I), although both the pure compounds and optionally also mixtures with different proportions of isomeric compounds are meant.
  • the formula (I) comprises all stereoisomers and mixtures thereof, in particular also racemic mixtures, and - as far as enantiomers are possible - both enantiomers and in particular the respective biologically active enantiomer.
  • A is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 3 -C 6 ) -alkyl, benzyl or halophenyl- (C 1 -C 6 ) -alkyl ;
  • B is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, benzyl or halophenyl- (C 1 -C 6 ) alkyl; n is 0, 1, 2 or 3;
  • E is Na + , K + , (Mg 2+ ) 1/2, (Ca 2+ ) i 2 , R 13 R 14 R 15 R 16 N + or NH 4 + ;
  • R 13 , R 14 , R 15 and R 16 are independently (C 1 -C 6 ) -alkyl or benzyl;
  • R 1 denotes (C 1 -C 6) -alkyl substituted by n halogen atoms or (C 3 -C 6) -cycloalkyl in each case substituted by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy, Phenyl or phenyl (C 1 -C 4 ) alkyl;
  • R 2 is (C 1 -C 6) -alkyl substituted by n halogen atoms or (C 3 -C 6) -cycloalkyl in each case substituted by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy, Phenyl or benzyl;
  • R 3 , R 4 and R 5 are each independently substituted by n halogen atoms (C 1 -C 6) -alkyl or by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy-substituted Phenyl or benzyl;
  • R 6 and R 7 independently of one another are each hydrogen, (C 1 -C 6) -alkyl substituted by n halogen atoms or phenyl or benzyl substituted by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and (C 1 -C 4 ) -alkoxy ;
  • R 8 is substituted by n halogen atoms (C 1 -C 6) alkyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkynyl or by n radicals from the group consisting of halogen, (Ci-C 4 ) - alkyl and (C 1 -C 4 ) -alkoxy-substituted phenyl or phenyl- (C 1 -C 4 ) -alkyl; and
  • X is hydrogen, methyl, ethyl or cyclopropyl
  • Y is halogen, cyano, nitro, halo (C 1 -C 6) -alkyl, halogeno (C 1 -C 6) -alkoxy, (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -alkoxy or by n
  • z represents hydrogen, halogen, halo (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, halo (C 1 -C 6) alkoxy, (C 3 -C 6) cycloalkyl or phenyl substituted by n halogen atoms;
  • X is halogen, cyano, nitro, halo (Ci-C6) alkyl, halo (d- C6) alkoxy, (Ci-C 6) alkoxy or (C 3 -C 6) cycloalkyl;
  • Y is hydrogen, halogen, cyano, nitro, (C 3 -C 6) -cycloalkyl, (C 1 -C 6) -alkyl substituted by n halogen atoms, (C 1 -C 6) -alkoxy or phenyl;
  • Z is hydrogen, halogen, cyano, nitro, (C 3 -C 6) -cycloalkyl or (C 1 -C 6) -alkyl substituted by n halogen atoms, (C 1 -C 6) -alkoxy or phenyl.
  • A is hydrogen, methyl, ethyl, isobutyl, cyclopropyl, cyclopropylmethyl, benzyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl or 4-chlorophenylmethyl;
  • B is hydrogen, methyl, ethyl, isobutyl, t-butyl, cyclopropyl, cyclopropylmethyl, benzyl, 2-chlorophenylmethyl, 3-chlorophenylmethyl or 4-chlorophenylmethyl, n is 0, 1, 2 or 3;
  • E is Na + , K + , (Mg 2+ ) i / 2 , (Ca 2+ ) i 2 , (CH 3 ) 4 N + or NH 4 + ;
  • M is oxygen
  • R 1 represents (Ci-C 6) -alkyl or (C 3 -C 6) cycloalkyl
  • R 2 is (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl or benzyl
  • R 3 , R 4 and R 5 are each independently (C 1 -C 6) alkyl, phenyl or benzyl;
  • R 6 and R 7 are each independently hydrogen, (C 1 -C 6) alkyl, phenyl or benzyl;
  • R ö is (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl or by n radicals from the group consisting of halogen, (C 1 -C 4 ) -alkyl and ( dC 4 ) alkoxy substituted benzyl; and is hydrogen, methyl or ethyl;
  • X is fluorine, bromine, chlorine, iodine, cyano, nitro, methoxy, ethoxy,
  • Y is hydrogen, fluorine, bromine, chlorine, iodine, methyl, ethyl, methoxy,
  • Z is hydrogen, fluorine, bromine, chlorine, iodine, methyl, ethyl, methoxy,
  • Y is fluorine, bromine, chlorine or iodine
  • Z is hydrogen, fluorine, bromine, chlorine, iodine, (C 3 -C 6 ) -cycloalkyl; or b) X is fluorine, bromine, chlorine or iodine;
  • Y is fluorine, bromine, chlorine iodine, methyl or ethyl
  • Z is methyl, ethyl, fluorine, bromine, chlorine, iodine or trifluoromethoxy.
  • herbicide-safener combinations comprising compounds of the general formula (I) in which
  • A is hydrogen or methyl;
  • B is methyl;
  • M is oxygen
  • R 1 is methyl
  • R 2 is ethyl
  • R 3 is methyl
  • R 8 is propynyl
  • X is ethyl
  • Y is chlorine
  • z is hydrogen, fluorine or cyclopropyl; or b) X is bromine or chlorine;
  • Y is ethyl
  • z is methyl, fluorine or trifluoromethoxy.
  • herbicide-safener combinations containing the compounds of the general formula (I) given in Tables 1 to 176: TABLE 1 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B cyclopropylmethyl.
  • Table 3 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 4 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 9 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is cyclo-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 10 Compounds of the general formula (I) in which G is hydrogen and iso-propyl, and B is cyclo-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 12 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2,2-difluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 13 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B B is 2,2-difluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 14 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 2,2-difluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 15 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2,2-difluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 16 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 2,2,2-trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 17 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2,2,2-trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 18 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 2,2,2-trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 19 Compounds of the general formula (I) in which G is hydrogen and A is isobutyl, and B is 2,2,2-trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 20 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2,2,2-trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 21 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is benzyl and X, Y and Z have the meanings given in Table 1.
  • Table 22 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is benzyl and X, Y and Z have the meanings given in Table 1.
  • Table 23 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is benzyl and X, Y and Z have the meanings given in Table 1.
  • Table 24 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is benzyl, and X, Y and Z have the meanings given in Table 1.
  • Table 25 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is benzyl and X, Y and Z have the meanings given in Table 1.
  • Table 26 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 2-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 27 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 28 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 2-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 29 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 2-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 30 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 31 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 3-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 32 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 3-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 33 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 3-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 34 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 3-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 35 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 3-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 36 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 4-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 37 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 4-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 38 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 4-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 39 Compounds of general formula (I) wherein G is hydrogen, A is iso-butyl, and B is 4-chlorophenylmethyl and X, Y and Z are as defined in Table 1.
  • Table 40 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 4-chlorophenylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 42 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2-phenylethyl and X, Y and Z have the meanings given in Table 1.
  • Table 43 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 2-phenylethyl and X, Y and Z have the meanings given in Table 1.
  • Table 44 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 2-phenylethyl and X, Y and Z have the meanings given in Table 1.
  • Table 45 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2-phenylethyl and X, Y and Z have the meanings given in Table 1.
  • Table 46 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 2- (2-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 47 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2- (2-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 48 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2- (2-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 49 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 2- (2-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 50 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2- (2-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 51 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is 2- (4-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 52 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is 2- (4-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 53 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is 2- (4-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 54 Compounds of the general formula (I) in which G is hydrogen, A is iso-butyl, and B is 2- (4-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 55 Compounds of the general formula (I) in which G is hydrogen, A is isopropyl, and B is 2- (4-chlorophenyl) -ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 56 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B 4 is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 57 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 58 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl and iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 59 Compounds of the general formula (I) in which G is hydrogen, A is c-pentyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 60 Compounds of the general formula (I) in which G is hydrogen, A is c-pentyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 62 Compounds of the general formula (I) in which G is hydrogen, A is benzyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 63 Compounds of the general formula (I) in which G is hydrogen, A is benzyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 64 Compounds of the general formula (I) in which G is hydrogen, A is benzyl and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 65 Compounds of the general formula (I) in which G is hydrogen, A is 4-fluorobenzyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 66 Compounds of the general formula (I) in which G is hydrogen, A is 4-fluorobenzyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 67 Compounds of the general formula (I) in which G is hydrogen, A is 4-fluorobenzyl, and B is isobutyl and X, Y and Z have the meanings given in Table 1.
  • Table 68 Compounds of the general formula (I) in which G is hydrogen, A is 2-fluorobenzyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 69 Compounds of the general formula (I) in which G is hydrogen, A is 2-fluorobenzyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 70 Compounds of the general formula (I) in which G is hydrogen, A is 2-fluorobenzyl, and B is isobutyl and X, Y and Z have the meanings given in Table 1.
  • Table 71 Compounds of the general formula (I) in which G is hydrogen, A is 3-fluorobenzyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 72 Compounds of the general formula (I) in which G is hydrogen, A is 3-fluorobenzyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 73 Compounds of the general formula (I) in which G is hydrogen, A is 3-fluorobenzyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 74 Compounds of the general formula (I) in which G is hydrogen, A is 2-phenylethyl, and B is 4-methyl and X, Y and Z have the meanings given in Table 1.
  • Table 75 Compounds of the general formula (I) in which G is hydrogen, A is 2-phenylethyl, and B is 4-ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 76 Compounds of the general formula (I) in which G is hydrogen, A is 2-phenylethyl, and B is 4-isobutyl and X, Y and Z have the meanings given in Table 1.
  • Table 77 Compounds of the general formula (I) in which G is hydrogen, A is 2- (4-chlorophenyl) -ethyl, and B is 4-methyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 78 Compounds of the general formula (I) in which G is hydrogen, A is 2- (4-chlorophenyl) -ethyl, and B is 4-ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 79 Compounds of general formula (I) wherein G is hydrogen, A is 2- (4-chlorophenyl) -ethyl, and B is 4-iso-butyl and X, Y and Z are those shown in Table 1 Have meanings.
  • Table 80 Compounds of the general formula (I) in which G is hydrogen, A is 2- (2-chlorophenyl) -ethyl, and B is 4-methyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 81 Compounds of the general formula (I) in which G is hydrogen, A is 2- (2-chlorophenyl) -ethyl, and B is 4-ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 82 Compounds of the general formula (I) in which G is hydrogen, A is 2- (4-chlorophenyl) -ethyl, and B is 4-isobutyl and X, Y and Z are the meanings given in Table 1 to have.
  • Table 83 Compounds of the general formula (I) in which G is hydrogen, A is 2- (3-chlorophenyl) -ethyl, and B is 4-methyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 84 Compounds of the general formula (I) in which G is hydrogen, A is 2- (3-chlorophenyl) -ethyl, and B is 4-ethyl and X, Y and Z have the meanings given in Table 1 ,
  • Table 85 Compounds of general formula (I) wherein G is hydrogen, A is 2- (3-chlorophenyl) -ethyl, and B is 4-iso-butyl and X, Y and Z are those shown in Table 1 Have meanings.
  • Table 86 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 87 Compounds of general formula (I) wherein G is hydrogen, A is c-propyl, and B is 2,2-difluoroethyl and X, Y and Z are as defined in Table 1.
  • Table 88 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B 4-2,2,2 is trifluoroethyl and X, Y and Z have the meanings given in Table 1.
  • Table 89 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 90 Compounds of the general formula (I) in which G is hydrogen, A is c-propyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 91 Compounds of the general formula (I) in which G is ethoxycarbonyl and A and B are each methyl.
  • Table 92 Compounds of the general formula (I) in which G is isopropylcarbonyl, and A and B are each methyl and X, Y and Z have the meanings given in Table 1.
  • Table 93 Compounds of the general formula (I) in which G is methylsulfonyl, and A and B are each methyl and X, Y and Z have the meanings given in Table 1.
  • Table 94 Compounds of the general formula (I) in which G is propynyl, and A and B are each methyl and X, Y and Z have the meanings given in Table 1.
  • Table 95 Compounds of the general formula (I) in which G is butinyl, and A and B are each methyl and X, Y and Z have the meanings given in Table 1.
  • Table 96 Compounds of the general formula (I) in which G is butinyl, and A and B are each methyl and X, Y and Z have the meanings given in Table 1.
  • Table 97 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 98 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 99 Compounds of the general formula (I) in which G is methylsulfonyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 100 Compounds of the general formula (I) in which G is propynyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 101 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 102 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 103 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is methyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 104 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is methyl, and B is isobutyl and X, Y and Z have the meanings given in Table 1.
  • Table 105 Compounds of the general formula (I) in which G is methylsulfonyl, A is methyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 106 Compounds of the general formula (I) in which G is propynyl, A is methyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 107 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 108 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 109 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 10 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 1 1 Compounds of the general formula (I) in which G is methylsulfonyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 12 Compounds of the general formula (I) in which G is propynyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 13 Compounds of the general formula (I) in which G is butinyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 14 Compounds of the general formula (I) in which G is butinyl, A is ethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 15 Compounds of the general formula (I) in which G is ethoxycarbonyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 16 Compounds of the general formula (I) in which G is isopropylcarbonyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 17 Compounds of the general formula (I) in which G is methylsulfonyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 18 Compounds of general formula (I) wherein G is propynyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 1 19 Compounds of the general formula (I) in which G is butinyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 120 Compounds of the general formula (I) in which G is butinyl, and A and B are each ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 121 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is ethyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 122 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is ethyl, and B is isobutyl and X, Y and Z have the meanings given in Table 1.
  • Table 123 Compounds of the general formula (I) in which G is methylsulfonyl, and A is ethyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 124 Compounds of the general formula (I) in which G is propynyl, A is ethyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 125 Compounds of the general formula (I) in which G is butinyl, A is ethyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 126 Compounds of the general formula (I) in which G is butinyl, A is ethyl, and B is iso-butyl and X, Y and Z have the meanings given in Table 1.
  • Table 127 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is iso-butyl, and B is in each case methyl and X, Y and Z have the meanings given in Table 1.
  • Table 128 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is isobutyl, and B is in each case methyl and X, Y and Z have the meanings given in Table 1.
  • Table 129 Compounds of the general formula (I) in which G is allyl and A is iso-butyl, and B is in each case methyl and X, Y and Z have the meanings given in Table 1.
  • Table 130 Compounds of the general formula (I) in which G is propynyl, A is iso-butyl, and B is in each case methyl and X, Y and Z have the meanings given in Table 1.
  • Table 132 Compounds of the general formula (I) in which G is butinyl, A is iso-butyl, and B is in each case methyl and X, Y and Z have the meanings given in Table 1.
  • Table 133 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is isobutyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 134 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is isobutyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 135 Compounds of the general formula (I) in which G is methylsulfonyl and A is iso-butyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 136 Compounds of the general formula (I) in which G is propynyl, A is isobutyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 137 Compounds of the general formula (I) in which G is butinyl, A is iso-butyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 138 Compounds of the general formula (I) in which G is butinyl, A is iso-butyl, and B is in each case ethyl and X, Y and Z have the meanings given in Table 1.
  • Table 139 Compounds of the general formula (I) in which G is ethoxycarbonyl, A and B are isobutyl, X, Y and Z have the meanings given in Table 1.
  • Table 140 Compounds of the general formula (I) in which G is isopropylcarbonyl, A and B are isobutyl, and X, Y and Z have the meanings given in Table 1.
  • Table 141 Compounds of the general formula (I) in which G is methylsulfonyl, A and B are isobutyl, and X, Y and Z have the meanings given in Table 1.
  • Table 142 Compounds of the general formula (I) in which G is propynyl, A and B are isobutyl, and X, Y and Z have the meanings given in Table 1.
  • Table 143 Compounds of the general formula (I) in which G is butinyl, A and B are isobutyl, and X, Y and Z have the meanings given in Table 1.
  • Table 144 Compounds of the general formula (I) in which G is butinyl, A and B are isobutyl, and X, Y and Z have the meanings given in Table 1.
  • Table 145 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is methyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 146 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is methyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 147 Compounds of the general formula (I) in which G is methylsulfonyl, A is methyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 148 Compounds of the general formula (I) in which G is propynyl, A is methyl, B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 149 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 150 Compounds of the general formula (I) in which G is butinyl, A is methyl, and B is cyclopropylmethyl and X, Y and Z have the meanings given in Table 1.
  • Table 151 Compounds of the general formula (I) in which G is ethoxycarbonyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 152 Compounds of the general formula (I) in which G is isopropylcarbonyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 153 Compounds of the general formula (I) in which G is methylsulfonyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 154 Compounds of the general formula (I) in which G is propynyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 155 Compounds of the general formula (I) in which G is butinyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 156 Compounds of the general formula (I) in which G is butinyl, A is cyclopropylmethyl, and B is methyl and X, Y and Z have the meanings given in Table 1.
  • Table 157 Compounds of the general formula (I) in which G is hydrogen, A is hydrogen, and B is ethyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 158 Compounds of the general formula (I) in which G is hydrogen, A is hydrogen, and B is n-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 159 Compounds of the general formula (I) in which G is hydrogen, A is hydrogen, and B is i-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 160 Compounds of the general formula (I) in which G is hydrogen and A is methyl and B is methyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 161 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is ethyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 162 Compounds of the general formula (I) in which G is hydrogen, A is methyl, and B is n-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 163 Compounds of general formula (I) wherein G is hydrogen, A is methyl, and B is i-propyl, and X, Y and Z are each as defined in Table 1.
  • Table 164 Compounds of the general formula (I) in which G is hydrogen and A is ethyl and B is methyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 165 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is ethyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 166 Compounds of the general formula (I) in which G is hydrogen, A is ethyl, and B is n-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 168 Compounds of the general formula (I) in which G is hydrogen and A is propyl and B is methyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 169 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is ethyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 170 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is n-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 171 Compounds of the general formula (I) in which G is hydrogen, A is propyl, and B is i-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 172 Compounds of the general formula (I) in which G is hydrogen and A is i-propyl and B is methyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 173 Compounds of the general formula (I) in which G is hydrogen, A is i-propyl, and B is ethyl, and X, Y and Z have the meanings given in Table 1.
  • Table 174 Compounds of the general formula (I) in which G is hydrogen, A is i-propyl, and B is n-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 175 Compounds of the general formula (I) in which G is hydrogen, A is hydrogen, and B is methyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • Table 176 Compounds of the general formula (I) in which G is hydrogen, A is i-propyl, and B is i-propyl, and X, Y and Z have the meanings given in Table 1, respectively.
  • the present invention also provides mixtures comprising stereoisomers which are encompassed by formula (I) or by the formulas of component B (safener).
  • Such compounds of the formula (I) or of the formulas of the component B (safener) contain, for example, one or more asymmetrically substituted carbon atoms or sulfoxides.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers and diastereomers, are all encompassed by the formula (I) or by the formulas of component B (safener) and can be obtained by conventional methods from mixtures of the stereoisomers or else by stereoselective reactions in combination be prepared with the use of stereochemically pure starting materials or auxiliaries.
  • Methyl Ph phenyl
  • Table 177 Compounds of the general formula (I) in which G is hydrogen.
  • Chlorophyll (bs, 1H), 7.70 (s, 1H), 7.47 (dd, 1H); nyl) -ethyl 7.32 (m, 2H), 7.26 (d, 1H), 7.18 (d,
  • Table 182 Compounds of the general formula (I) in which G is R 8 .
  • the application rates are generally lower, z. In the range of 0.1 g to 500 g a.i./ha, preferably 10 g to 400 g a.i./ha, more preferably 20 g to 300 g a.i./ha.
  • the herbicides of the general formula (I) are suitable for controlling harmful plants, for example in crops, for example in economically important arable crops, for example monocotyledonous crops such as cereals (for example wheat, Barley, rye, oats), rice, maize, millet, or dicotyledonous crops such as sugarbeet, oilseed rape, cotton, sunflower and legumes, for example of the genera Glycine (eg Glycine max. (Soy) as non-transgenic glycine max.
  • monocotyledonous crops such as cereals (for example wheat, Barley, rye, oats), rice, maize, millet, or dicotyledonous crops such as sugarbeet, oilseed rape, cotton, sunflower and legumes, for example of the genera Glycine (eg Glycine max. (Soy) as non-transgenic glycine max.
  • these cultures are also preferred, particularly preferred is the use in cereals (eg wheat, barley, rye, oats), rice, corn, millet, sugar beet , Cane, sunflower, canola and cotton.
  • the herbicide-safener combinations (A) + (B) are also useful in tolerant and non-tolerant mutant cultures and tolerant and intolerant transgenic cultures, preferably of corn, rice, corn, oilseed rape and soy, for example those directed against imidazolinone herbicides. Atrazine, glufosinate or glyphosate are resistant.
  • the compounds of the general formula (I) are known from WO 2005/063721 A and WO 2007/082076 A and can be obtained by the processes described therein.
  • component (B) is compounds which are suitable for reducing the phytotoxic effects of crop protection active ingredients such as herbicides on crop plants.
  • Dichlorophenylpyrazolecarboxylic acid derivatives (S1 b), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylate (S1 -2), 1 - (2,4-dichlorophenyl) -5-isopropylpyrazol-3- carboxylic acid ethyl ester (S1 -3), 1- (2,4-dichlorophenyl) -5- (1, 1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S1 -4) and related compounds, as described in EP-A 333,131 and EP-A-269,806 are described;
  • 1, 5-diphenylpyrazole-3-carboxylic acid S1 c
  • compounds such as 1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1 -5), 1 - (2-chlorophenyl) - Methyl 5-phenylpyrazole-3-carboxylate (S1 -6) and related compounds as described, for example, in EP-A-268554;
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • Benoxacor (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-1,4-benzoxazine) (S3-4),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) -methyl] -dichloroacetamide
  • AD-67 or "MON 4660” (3-dichloroacetyl-1-oxa-3-aza-spiro [4,5] decane) from Nitrokemia or Monsanto (S3-7),
  • TI-35 (1-dichloroacetyl-azepane) from TRI-Chemical RT (S3-8),
  • R A 2 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3;
  • RB 1 , RB 2 independently of one another are hydrogen, (C 1 -C 6) -alkyl,
  • R B 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkyl or (C 1 -C 4 ) alkoxy and
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (RB 3 ) 2-OMe (S4-1, "Cyprosulfamide”)
  • R B 1 cyclopropyl
  • R B 2 hydrogen
  • (RB 3 ) 5-CI-2-OMe (S4-2)
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (RB 3 ) 5-CI-2-OMe is (S4-4) and
  • Rc 1 , Rc 2 are each independently hydrogen, (Ci-Cs) alkyl,
  • Rc 3 is halogen, (C 1 -C 4 ) alkyl, (C 1 -C 4 ) alkoxy, CF 3 nric 1 or 2; for example
  • S6 active compounds from the class of 1, 2-dihydroquinoxaline-2-ones (S6), e.g.
  • S7 Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g. Methyl diphenylmethoxyacetate (CAS No. 41858-19-9) (S7-1), ethyl diphenylmethoxyacetate or diphenylmethoxyacetic acid as described in WO-A-98/38856.
  • S7 diphenylmethoxyacetic acid derivatives
  • R D 1 is halogen, (Ci-C 4) alkyl, (dC 4) haloalkyl, (dC 4) alkoxy, (dC 4) haloalkoxy, R 2 is hydrogen or D (dC 4) alkyl
  • R D 3 is hydrogen, (C 1 -C 8 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, or aryl, where each of the abovementioned C-containing radicals is unsubstituted or substituted by one or more preferably up to three identical or different radicals from the
  • n D is an integer from 0 to 2.
  • R E 1 is halogen, (C 1 -C 4 ) alkyl, methoxy, nitro, cyano, CF 3 , OCF 3
  • n E is an integer from 0 to 4,
  • R E 2 is (C 1 -C 6 ) alkyl, (C 2 -C 6 ) alkenyl, (C 3 -C 6 ) cycloalkyl, aryl; Benzyl, halobenzyl, R E 3 is hydrogen or (Ci-C 6 ) alkyl.
  • S1 1 active ingredients of the type of oxyimino compounds (S1 1), which are known as seed dressing, such.
  • Oxabetrinil ((Z) -1, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (S1 1 -1), which is known as a seedling safener for millet against damage from metolachlor,
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (S1 1 -3), which is known as a seed dressing safener for millet against damage by metolachlor.
  • Naphthalene anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as
  • Seed pickling safener for maize known for damage from thiocarbamate herbicides
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as safener for corn,
  • active substances which, in addition to a herbicidal activity against harmful plants, also have safener action on crops such as rice, such as, for example, rice.
  • NK 049 3,3'-dimethyl-4-methoxybenzophenone known as safener for rice against damage of some herbicides "COD” (1-Bromo-4- (chloromethylsulfonyl) benzene) by Kumiai, (CAS No. 54091 -06-4), known as safener against damage of some herbicides in rice.
  • RH 1 represents a (d-C6) haloalkyl radical
  • RH 2 is hydrogen or halogen
  • RH 3, RH 4 are independently hydrogen, (d-Ci6) alkyl, (C2-Ci6) alkenyl or (C 2 -C 6) alkynyl, wherein each of the 3 last-mentioned radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (dC 4) alkoxy, (dC 4) haloalkoxy, (dC 4) alkylthio, (Ci-C 4) alkylamino, di [ (Ci-C 4) alkyl] -amino, [(dC 4) alkoxy] carbonyl, [(dC 4) haloalkoxy] - carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted is and heterocyclyl which is unsubstituted or substituted, is substituted,
  • each of the latter 4 radicals being unsubstituted or substituted by one or more radicals from the group halogen, hydroxy, cyano, (dC 4) alkyl, (dC 4) haloalkyl, (dC 4) alkoxy, (dC 4) haloalkoxy, (dC 4) alkylthio, (CrC 4) alkylamino, di [(CrC 4) alkyl] amino, [(Ci -C 4) AI koxyj-carbonyl, [(Ci-C4) Haloal koxyj-carbonyl, (C3-C6) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted,
  • RH 4 is hydrogen or (C 1 -C 4 ) -alkyl or
  • RH 3 and RH 4 together with the directly bonded N atom form a four- to eight-membered heterocyclic ring which, in addition to the N atom, also contains further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S. can and unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (dC 4 ) alkyl, (dC 4 ) haloalkyl, (dC 4 ) alkoxy, (dC 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted means.
  • S16) active substances which are used primarily as herbicides, but also have safener effect on crop plants, eg

Abstract

Es werden Herbizid-Safener-Kombinationen enthaltend 4-Phenylpyridazinone der Formel (I) und Safener beschrieben. In Formel (I) stehen A, B, G, X, Y und Z für Wasserstoff, Halogen, Nitro und organische Reste wie Alkyl, Alkoxy und Halogenalkyl.

Description

Herbizid-Safener-Kombinationen enthaltend Arylpyridazinone und Safener
Beschreibung
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere Herbizid-Antidot-Kombinationen (Wirkstoff-Safener-Kombinationen), die für den Ein- satz gegen konkurrierende Schadpflanzen in Nutzpflanzenkulturen geeignet sind.
Aus WO2007/1 19434 und WO 2009/035150 sind herbizid wirksame 4-Phenyl- pyridazinone bekannt, die in 2-Position des Phenylrings einen Alkyl- oder Alkoxrest tragen. Weiterhin offenbaren diese Schriften, dass diese 4-Phenylpyridazinone mit Safenern und weiteren Herbiziden verwendet können. Aus WO2009/035145 sind Mischungen von 4-alkyl-substiutierten Aryl-pyridazinonen mit einem weiteren Herbizid und Safenern bekannt.
Allerdings sind die vorstehend genannten Pyridazinone und deren Mischungen mit Safener zum Teil nicht voll verträglich mit einigen wichtigen Kulturpflanzen wie z.B. verschiedenen Getreidearten, Mais, Reis, Getreide oder Zuckerrohr. Sie können deshalb in manchen Kulturen nicht oder nur in so geringen Aufwandmengen eingesetzt werden, daß die erwünschte breite herbizide Wirksamkeit gegenüber Schadpflanzen nicht gewährleistet ist.
Aufgabe der vorliegenden Erfindung ist es daher, herbizide Mittel bereit zu stellen, in welchen die Selektivität der oben genannten Arylpyridazinone gegenüber wichtigen Kulturpflanzen erhöht ist. Diese Aufgabe wird durch die erfindungsgemäßen Herbizid-Safener-Kombinationen enthaltend Arylpyridazinone und Safener gelöst.
Gegenstand der vorliegenden Erfindung sind daher Herbizid-Safener- Kombinationen, enthaltend 4-Phenylpyridazinone der Formel (I) oder deren Salze
Figure imgf000003_0001
worin
A und B bedeuten unabhängig voneinander jeweils Wasserstoff, (C3-C6)- Cycloalkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (C3-C6)- Cycloalkyl, Phenyl und Halogenphenyl substituiertes (d-C6)-Alkyl, n bedeutet 0, 1 , 2 oder 3;
G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8; E bedeutet ein Metallionäquivalent oder ein Ammoniunnion; L bedeutet Sauerstoff oder Schwefel ; M bedeutet Sauerstoff oder Schwefel ;
R1 bedeutet jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-C-6)- Alkenyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl, Di-(Ci-C4)-alkoxy-(Ci-C6)-alkyl oder (d-C4)- Alkylthio-(Ci-C6)-alkyl,
einen durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d- C4)-Alkoxy substituierten, vollständig gesättigten, 3- bis 6-gliedrigen Ring bestehend aus 3 bis 5 Kohlenstoffatonnen und 1 bis 3 Heteroatomen aus der Gruppe Sauerstoff, Schwefel und Stickstoff,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl, Phenyl-(Ci-C4)-alkyl, Heteroaryl, Phenoxy-(Ci-C4)-alkyl oder Heteroaryloxy-(CrC4)-alkyl;
R2 bedeutet jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-C6)- Alkenyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl oder Di-(Ci-C4)-alkoxy-(Ci-C6)-alkyl,
oder durch jeweils n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Benzyl;
R3, R4 und R5 bedeuten unabhängig voneinander jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (d-C4)-Alkoxy, N-(Ci-C6)-Alkylamino, N,N-Di-(d- C6)-Alkylamino, (d-C4)-Alkylthio, (C2-C4)-Alkenyl oder (C3-C6)-Cycloalkylthio, oder durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d- C4)-Alkoxy substituiertes Phenyl, Benzyl, Phenoxy oder Phenylthio;
R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff,
durch n Halogenatome substituiertes (d-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-Ce)-Al- kenyl, (Ci-C6)-Alkoxy oder (Ci-C4)-Alkoxy-(Ci-C6)-alkyl,
durch jeweils n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes Phenyl oder Benzyl;
oder R6 und R7 bilden gemeinsam mit dem N-Atom, an das sie gebunden sind, einen 3- bis 6-gliedrigen Ring enthaltend 2 bis 5 Kohlenstoffatomen und 0 oder 1 Sauerstoff- oder Schwefelatome;
R8 bedeutet durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-Ce)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl, (C1 -C4)-Al kylth io-(Ci -C4)-al kyl oder Di- (Ci-C4)-alkoxy-(Ci-C6)-alkyl,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl,
einen durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d- C4)-Alkoxy substituierten, vollständig gesättigten, 3- bis 6-gliedrigen Ring bestehend aus 3 bis 5 Kohlenstoffatomen und 1 bis 3 Heteroatomen aus der Gruppe Sauerstoff, Schwefel und Stickstoff,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- AI koxy substituiertes Phenyl, Phenyl-(d-C4)-alkyl, Heteroaryl, Phenoxy-(d-C4)-alkyl oder Heteroaryloxy-(Ci -C4)-al kyl ;
und bedeutet Wasserstoff, (d-C6)-Alkyl oder (C3-C6)-Cycloalkyl,
bedeutet Halogen, Cyano, Nitro, Halogen-(d-C6)-alkyl, Halogen-(Ci C6)-alkoxy, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy oder durch n Halogenatome substituiertes Phenyl,
bedeutet Wasserstoff, Halogen, Cyano, Nitro, (d-C6)-Alkyl,
Halogen-(Ci -C6)-al kyl , Halogen-(Ci -C6)-al koxy, (C3-C6)-Cycloal kyl oder durch n Halogenatome substituiertes Phenyl;
bedeutet Halogen, Cyano, Nitro oder jeweils durch n Halogenatome substituiertes (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (CrC6)-Alkoxy oder Phenyl;
und Z bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl oder durch jeweils n Halogenatome substituiertes (Ci-C6)-Alkyl, (Ci-Ce)-Alkoxy oder Phenyl, und
(B) einen oder mehrere Safener,
wobei solche Herbizid-Safener-Kombinationen ausgenommen sein sollen, in denen der Index n für Null steht und der Safener Fenchlorazol-ethyl, Cloquintocet-mexyl oder Mefenpyr-diethyl ist. Die erfindungsgemäßen Herbizid-Safener-Kombinationen können zusätzliche weitere Komponenten, beispielsweise Pflanzenschutzmittelwirkstoffe anderer Art und/oder im Pflanzenschutz übliche Zusatzstoffe und/oder Formulierungshilfsmittel, enthalten oder zusammen mit diesen eingesetzt werden.
Nachfolgend sind die Begriffe Herbizid (A), 4-Phenylpyridazinone (A) und Verbin- düngen der Formel (I) gleichbedeutend zu verstehen.
Die Herbizide (A) und die Safener (B) können auf bekannte Weise angewendet werden, beispielsweise gemeinsam (beispielsweise als Co-Formulierung oder als Tank- Mischung) oder auch zeitlich versetzt (Splitting), z.B. auf die Pflanzen, Pflanzenteile, Pflanzensamen oder die Fläche, auf der die Pflanzen wachsen. Möglich ist z.B. die Anwendung der Einzelwirkstoffe oder der Herbizid-Safener-Kombi-nationen in mehreren Portionen (Sequenzanwendung), z. B. nach Anwendungen im Vorauflauf, gefolgt von Nachauflauf-Applikationen oder nach frühen Nachauflaufanwendungen, gefolgt von Applikationen im mittleren oder späten Nachauflauf. Bevorzugt ist dabei die gemeinsame oder die zeitnahe Anwendung der Wirkstoffe der jeweiligen Kombi- nation. Möglich ist auch die Anwendung der Einzel Wirkstoffe oder der Herbizid- Safener-Kombinationen zur Saatgutbehandlung.
Alkyl bedeutet gesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 1 bis 8 Kohlenstoffatomen, z.B. Ci-C6-Alkyl wie Methyl, Ethyl, Propyl, 1 -Methylethyl, Butyl, 1 -Methyl-propyl, 2-Methylpropyl, 1 ,1 -Dimethylethyl, Pentyl, 1 -Methylbutyl, 2- Methylbutyl, 3-Methylbutyl, 2,2-Di-methylpropyl, 1 -Ethylpropyl, Hexyl, 1 ,1 - Dimethylpropyl, 1 ,2-Dimethylpropyl,1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, 1 ,1 -Dimethylbutyl, 1 ,2-Dimethylbutyl, 1 ,3-Dimethylbutyl, 2,2- Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 ,1 ,2- Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl-1 -methylpropyl und 1 -Ethyl-2-methyl- propyl.
Halogenalkyl bedeutet geradkettige oder verzweigte Alkylgruppen mit 1 bis 8 Kohlenstoffatomen (wie oben genannt), wobei in diesen Gruppen teilweise oder voll- ständig die Wasserstoffatome durch Halogenatome ersetzt sein können, z.B. C1-C2- Halogenalkyl wie Chlormethyl, Brommethyl, Dichlormethyl, Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, Chlorfluormethyl, Dichlorfluormethyl, Chlordifluor- methyl, 1 -Chlorethyl, 1 -Bromethyl, 1 -Fluorethyl, 2-Fluorethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 2-Chlor-2-fluorethyl, 2-Chlor,2-difluorethyl, 2,2-Dichlor-2-fluorethyl, 2,2,2-Trichlorethyl, Pentafluorethyl und 1 ,1 ,1 -Trifluorprop-2-yl .
Alkenyl bedeutet ungesättigte, geradkettige oder verzweigte Kohlenwasserstoffreste mit 2 bis 8 Kohlenstoffatomen und einer Doppelbindung in einer beliebigen Position, z.B. C2-C6-Alkenyl wie Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methylethenyl, 1 -Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl-1 -propenyl, 2-Methyl-1 -propenyl, 1 -Methyl-2- propenyl, 2-Methyl-2-propenyl, 1 -Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 - Methyl-1 -butenyl, 2-Methyl-1 -butenyl, 3-Methyl-1 -butenyl, 1 -Methyl-2-butenyl, 2- Methyl-2-butenyl, 3-Methyl-2-butenyl, 1 -Methyl-3-butenyl, 2-Methyl-3-butenyl, 3- Methyl-3-butenyl, 1 ,1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl-1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl-1 -propenyl, 1 -Ethyl-2-propenyl, 1 -Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl-1 -pentenyl, 2-Methyl-1 -pentenyl, 3-Methyl-1 - pentenyl, 4-Methyl-1 -pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2 pentenyl, 4-Methyl-2-pentenyl, 1 -Methyl-3-pentenyl, 2-Methyl-3-pentenyl, 3-Methyl-3 pentenyl, 4-Methyl-3-pentenyl, 1 -Methyl-4-pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4 pentenyl, 4-Methyl-4-pentenyl, 1 ,1 -Dimethyl-2-butenyl, 1 ,1 ,-Dimethyl-3-butenyl, 1 ,2- Dimethyl-1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3-butenyl, 1 ,3-Dimethyl-1 - butenyl, 1 ,3-Dimethyl-2-butenyl, 1 ,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3- Dimethyl-1 -butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-1 - butenyl, 3,3-Dimethyl-2-butenyl, 1 -Ethyl-1 -butenyl, 1 -Ethyl-2-butenyl, 1 -Ethyl-3- butenyl, 2-Ethyl-1 -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1 ,1 ,2-Trimethyl-2- propenyl, 1 -Ethyl-1 -methyl-2-propenyl, 1 -Ethyl-2-methyl-1 -propenyl und 1 -Ethyl-2- methyl-2-propenyl.
Alkoxy bedeutet gesättigte, geradkettige oder verzweigte Alkoxyreste mit 1 bis 8 Kohlenstoffatomen, z.B. d-C6-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 - Methylethoxy, Butoxy, 1 -Methyl-propoxy, 2-Methylpropoxy, 1 ,1 -Dimethylethoxy, Pen toxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 2,2-Di-methylpropoxy, 1 - Ethylpropoxy, Hexoxy, 1 ,1 -Dimethylpropoxy, 1 ,2-Dimethylpropoxy,1 -Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, 1 ,1 -Dimethylbutoxy, 1 ,2- Dimethylbutoxy, 1 ,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3- Dimethylbutoxy, 1 -Ethylbutoxy, 2-Ethylbutoxy, 1 ,1 ,2-Trimethylpropoxy, 1 ,2,2-Tri- methylpropoxy, 1 -Ethyl-1 -methylpropoxy und 1 -Ethyl-2-methylpropoxy;
Halogenalkoxy bedeutet geradkettige oder verzweigte Alkoxygruppen mit 1 bis 8 Kohlenstoffatomen (wie vorstehend genannt), wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. d-C2-Halogenalkoxy wie Chlormethoxy, Brommethoxy, Dichlormethoxy, Trichlormethoxy, Fluormethoxy, Difluormethoxy, Trifluormethoxy, Chlorfluormethoxy, Dichlorfluormethoxy, Chlordifluormethoxy, 1 -Chlorethoxy, 1 - Bromethoxy, 1 -Fluorethoxy, 2-Fluorethoxy, 2,2-Difluorethoxy, 2,2,2-Trifluorethoxy, 2- Chlor-2-fluorethoxy, 2-Chlor,2-difluorethoxy, 2,2-Dichlor-2-fluorethoxy, 2,2,2- Trichlorethoxy, Pentafluor-ethoxy und 1 ,1 ,1 -Trifluorprop-2-oxy.
Alkylthio bedeutet gesättigte, geradkettige oder verzweigte Alkylthioreste mit 1 bis 8 Kohlenstoffatomen, z.B. Ci-C6-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1 - Methylethylthio, Butylthio, 1 -Methyl-propylthio, 2-Methylpropylthio, 1 ,1 - Dimethylethylthio, Pentylthio, 1 -Methylbutylthio, 2-Methylbutylthio, 3-Methylbutylthio, 2,2-Di-methylpropylthio, 1 -Ethylpropylthio, Hexylthio, 1 ,1 -Dimethylpropylthio, 1 ,2-Di- methylpropylthio,1 -Methylpentylthio, 2-Methylpentylthio, 3-Methyl-pentylthio, 4- Methyl pentylthio, 1 ,1 -Dimethylbutylthio, 1 ,2-Dimethylbutylthio, 1 ,3-Dimethyl-butylthio, 2,2-Dimethylbutylthio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, 1 ,1 ,2-Trimethylpropylthio, 1 ,2,2-Trimethylpropylthio, 1 -Ethyl-1 - methylpropyl-thio und 1 -Ethyl-2-methylpropylthio; Halogenalkylthio bedeutet geradkettige oder verzweigte Alkylthiogruppen mit 1 bis 8 Kohlenstoffatomen (wie vorstehend genannt), wobei in diesen Gruppen teilweise oder vollständig die Wasserstoffatome durch Halogenatome wie vorstehend genannt ersetzt sein können, z.B. Ci-C2-Halogenalkyl-thio wie Chlormethylthio, Brommethylthio, Dichlormethylthio, Trichlormethylthio, Fluormethylthio, Difluormethylthio, Trifluormethylthio, Chlorfluor- methylthio, Dichlorfluor-methylthio, Chlordifluormethylthio, 1 -Chlorethylthio, 1 - Bromethylthio, 1 -Fluorethylthio, 2-Fluorethylthio, 2,2-Difluorethylthio, 2,2,2- Trifluorethylthio, 2-Chlor-2-fluorethylthio, 2-Chlor,2-difluorethylthio, 2,2-Dichlor-2- fluorethylthio, 2,2,2-Trichlorethylthio, Pentafluorethylthio und 1 ,1 ,1 -Trifl uorprop-2- ylthio.
Heteroaryl bedeutet 2-Furyl, 3-Furyl, 2-Thienyl, 3-Thienyl, 1 -Pyrrolyl, 2-Pyrrolyl, 3- Pyrrolyl, 3-lsoxazolyl, 4-lsoxazolyl, 5-lsoxazolyl, 3-lsothiazolyl, 4-lsothiazolyl, 5- Isothiazolyl, 1 -Pyrazolyl, 3-Pyrazolyl, 4-Pyrazolyl, 5-Pyrazolyl, 2-Oxazolyl, 4- Oxazolyl, 5-Oxazolyl, 2-Thiazolyl, 4-Thiazolyl, 5-Thiazolyl, 1 -lnnidazolyl, 2-lnnidazolyl 4-lmidazolyl, 5-lmidazolyl, 1 ,2,4-Oxadiazol-3-yl, 1 ,2,4-Oxadiazol-5-yl, 1 ,2,4- Thiadiazol-3-yl, 1 ,2,4-Thiadiazol-5-yl, 1 ,3,4-Oxadiazol-2-yl, 1 ,3,4-Thiadiazol-2-yl, 1 ,2,4-Triazol-1 -yl, 1 ,2,4-Triazol-3-yl, 1 ,2,4-Triazol-4-yl, 1 ,2,4-Triazol-5-yl, 1 ,2,3- Triazol-1 -yl, 1 ,2,3-Triazol-2-yl, 1 ,2,3-Triazol-4-yl, Tetrazol-1 -yl, Tetrazol-2-yl, Tetra- zol-5-yl, lndol-1 -yl, lndol-2-yl, lndol-3-yl, lsoindol-1 -yl, lsoindol-2-yl, Benzofur-2-yl, Benzothiophen-2-yl, Benzofur-3-yl, Benzothiophen-3-yl, Benzoxazol-2-yl, Benzothia zol-2-yl, Benzimidazol-2-yl, lndazol-1 -yl, lndazol-2-yl, lndazol-3-yl, 2-Pyridinyl, 3- Pyridinyl, 4-Pyridinyl, 3-Pyridazinyl, 4-Pyridazinyl, 2-Pyrimidinyl, 4-Pyrimidinyl, 5- Pyrimidinyl, 2-Pyrazinyl, 1 ,3,5-Triazin-2-yl, 1 ,2,4-Triazin-3-yl, 1 ,2,4-Triazin-5-yl oder 1 ,2,4-Triazin-6-yl. Dieses Heteroaryl ist jeweils unsubstituiert oder jeweils einfach oder mehrfach gleich oder verschieden substituiert durch Reste ausgewählt aus Flu or, Chlor, Brom, lod, Cyano, Hydroxy, Mercapto, Amino, Methyl, Ethyl, n-Propyl, Isopropyl, n-Butyl, Isobutyl, sek-Butyl, tert-Butyl, Cyclopropyl, 1 -Chlorcyclopropyl, Vinyl, Ethinyl, Methoxy, Ethoxy, Isopropoxy, Methylthio, Ethylthio, Trifluormethylthio Chlordifluormethyl, Dichlorfluormethyl, Chlorfluormethyl, Chlormethyl, Dichlormethyl Trichlormethyl, Fluormethyl, Difluormethyl, Trifluormethyl, 2,2,2-Trifluorethyl, Triflu- ormethoxy, Trifluormethylthio, 2,2,2-Trifluor-thoxy, 2,2-Dichlor-2-fluorethyl, 2,2- Difluor-2-chlorethyl, 2-Chlor-2-fluorethyl, 2,2,2-Trichlorethyl, 2,2,2-Trifluorethyl, 2- Fluorethyl, 2,2-Difluorethyl, 2-Methoxyethoxy, Acetyl, Propionyl, Methoxycarbonyl, Ethoxycarbonyl, N-Methylamino, Ν,Ν-Dimethylamino, N-Ethylamino, N,N- Diethylamino, Aminocarbonyl, Methylaminocarbonyl, Dimethylaminocarbonyl, Di- methylcarbamoylamino, Methoxycarbonylamino, Methoxycarbonyloxy, Ethoxycarbo nylamino, Ethoxycarbonyloxy, Methylsulfamoyl, Dimethylsulfamoyl, Phenyl oder Phenoxy. Die Verbindungen der Formel (I) können, auch in Abhängigkeit von der Art der Sub- stituenten, als geometrische und/oder optische Isomere oder Isomeren-gemische, in unterschiedlicher Zusammensetzung vorliegen, die gegebenenfalls in üblicher Art und Weise getrennt werden können. Sowohl die reinen Isomeren als auch die Iso- merengemische, deren Herstellung und Verwendung sowie diese enthaltende Mittel sind Gegenstand der vorliegenden Erfindung. Im Folgenden wird der Einfachheit halber jedoch stets von Verbindungen der Formel (I) gesprochen, obwohl sowohl die reinen Verbindungen als gegebenenfalls auch Gemische mit unterschiedlichen Anteilen an isomeren Verbindungen gemeint sind.
Ist eine Gruppe mehrfach durch Reste substituiert, so ist darunter zu verstehen, daß diese Gruppe durch ein oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. Die Formel (I) umfasst alle Stereoisomeren und deren Gemische, insbesondere auch racemische Gemische, und - soweit Enantiomere möglich sind - beide Enanti- omere und insbesondere das jeweils biologisch wirksame Enantiomer.
Bevorzugt sind Verbindungen der allgemeinen Formeln (l-a), (l-b), (l-c), (l-d), (l-e), (I- f), (l-g) und (l-h):
Figure imgf000010_0001
Figure imgf000011_0001
Von besonderem Interesse sind Herbizid-Safener-Kombinationen enthaltend Verbindungen der allgemeinen Formel (I), worin
A bedeutet Wasserstoff, (d-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl- (C3-C6)-alkyl, Benzyl oder Halogenphenyl-(d-C6)-alkyl;
B bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl- (d-C6)-alkyl, Benzyl oder Halogenphenyl-(d-C6)-alkyl; n bedeutet 0, 1 , 2 oder 3;
G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8; E bedeutet Na+, K+, (Mg2+)1/2, (Ca2+)i 2 , R13R14R15R16N+ oder NH4+;
R13, R14, R15 und R16 bedeuten unabhängig voneinander (Ci-C6)-Alkyl oder Benzyl;
L bedeutet Sauerstoff;
M bedeutet Sauerstoff; R1 bedeutet durch n Halogenatome substituiertes (d-C6)-Alkyl oder jeweils durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Phenyl-(d-C4)-alkyl; R2 bedeutet durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder jeweils durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Benzyl;
R3, R4 und R5 bedeuten unabhängig voneinander jeweils durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Benzyl;
R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff, durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Benzyl;
R8 bedeutet durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-Ce)-Alkenyl, (C2- C6)-Alkinyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)- Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Phenyl-(Ci-C4)-alkyl; und
X bedeutet Wasserstoff, Methyl, Ethyl oder cyclo-Propyl;
Y bedeutet Halogen, Cyano, Nitro, Halogen-(d-C6)-alkyl, Halogen- (d-C6)-alkoxy, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy oder durch n
Halogenatome substituiertes Phenyl,
z bedeutet Wasserstoff, Halogen, Halogen-(d-C6)-alkyl, (d-C6)-Alkoxy, Halogen-(d-C6)-alkoxy, (C3-C6)-Cycloalkyl oder durch n Halogenatome substituiertes Phenyl;
oder b) X bedeutet Halogen, Cyano, Nitro, Halogen-(Ci-C6)-alkyl, Halogen-(d- C6)-alkoxy, (Ci-C6)-Alkoxy oder (C3-C6)-Cycloalkyl;
Y bedeutet Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl, durch jeweils n Halogenatome substituiertes (d-C6)-Alkyl, (Ci-Ce)-Alkoxy oder Phenyl;
Z bedeutet Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl oder durch jeweils n Halogenatome substituiertes (d-C6)-Alkyl, (C1-C6)- Alkoxy oder Phenyl.
Von ganz besonderem Interesse sind sind Herbizid-Safener-Kombinationen enthaltend Verbindungen der allgemeinen Formel (I), worin
A bedeutet Wasserstoff, Methyl, Ethyl, i-Butyl, cyclo-Propyl, cyclo-Propylmethyl, Benzyl, 2-Chlorphenylmethyl, 3-Chlorphenylmethyl oder 4-Chlorphenylmethyl;
B bedeutet Wasserstoff, Methyl, Ethyl, i-Butyl, t-Butyl, cyclo-Propyl, cyclo- Propylmethyl, Benzyl, 2-Chlorphenylmethyl, 3-Chlorphenylmethyl oder 4- Chlorphenylmethyl, n bedeutet 0, 1 , 2 oder 3;
G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8; E bedeutet Na+, K+, (Mg2+)i/2, (Ca2+)i 2, (CH3)4N+ oder NH4 +;
L bedeutet Sauerstoff;
M bedeutet Sauerstoff;
R1 bedeutet (Ci-C6)-Alkyl oder (C3-C6)-Cycloalkyl; R2 bedeutet (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl oder Benzyl;
R3, R4 und R5 bedeuten unabhängig voneinander jeweils (d-C6)-Alkyl, Phenyl oder Benzyl;
R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff, (d-C6)-Alkyl, Phenyl oder Benzyl;
Rö bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d-C4)-Alkoxy substituiertes Benzyl; und bedeutet Wasserstoff, Methyl oder Ethyl;
bedeutet Fluor, Brom, Chlor, lod, Cyano, Nitro, cyclo-Propyl, Methoxy Ethoxy, Trifluormethyl oder Trifluormethoxy, Phenyl oder Halogenphenyl;
bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methoxy, Ethoxy, Triflu ormethyl oder cyclo-Propyl;
b) X bedeutet Fluor, Brom, Chlor, lod, Cyano, Nitro, Methoxy, Ethoxy,
Trifluormethyl, Trifluormethoxy oder cyclo-Propyl
Y bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methyl, Ethyl, Methoxy,
Ethoxy, Trifluormethyl, Trifluormethoxy oder cyclo-Propyl;
Z bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methyl, Ethyl, Methoxy,
Ethoxy, Trifluormethyl, Trifluormethoxy, cyclo-Propyl, Chlorphenyl oder
Fluorphenyl.
Von ganz besonderem Interesse sind insbesondere sind Herbizid-Safener- Kombinationen enthaltend Verbindungen der allgemeinen Formel (I), worin A bedeutet Wasserstoff oder (Ci-C2)-Alkyl; B bedeutet (Ci-C2)-Alkyl; G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3 oder R8; L bedeutet Sauerstoff; M bedeutet Sauerstoff; R1 bedeutet (Ci-C2)-Alkyl, R2 bedeutet (CrC2)-Alkyl, R3 bedeutet (d-C2)-Alkyl, R8 bedeutet (C2-C6)-Alkinyl, und a) X bedeutet Methyl oder Ethyl;
Y bedeutet Fluor, Brom, Chlor oder lod;
Z bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, (C3-C6)-Cycloalkyl; oder b) X bedeutet Fluor, Brom, Chlor oder lod;
Y bedeutet Fluor, Brom, Chlorjod, Methyl oder Ethyl;
Z bedeutet Methyl, Ethyl, Fluor, Brom, Chlor, lod oder Trifluormethoxy. Ganz besonders bevorzugt sind sind Herbizid-Safener-Kombinationen enthaltend Verbindungen der allgemeinen Formel (I), worin
A bedeutet Wasserstoff oder Methyl ; B bedeutet Methyl;
G bedeutet Wasserstoff, C(=O)R1 , C(=L)MR2, SO2R3 oder R8;
L bedeutet Sauerstoff;
M bedeutet Sauerstoff;
R1 bedeutet Methyl, R2 bedeutet Ethyl,
R3 bedeutet Methyl,
R8 bedeutet Propinyl, und
X bedeutet Ethyl;
Y bedeutet Chlor;
z bedeutet Wasserstoff, Fluor oder Cyclopropyl; oder b) X bedeutet Brom oder Chlor;
Y bedeutet Ethyl;
z bedeutet Methyl, Fluor oder Trifluormethoxy. Von besonderem Interesse sind auch Herbizid-Safener-Kombinationen enthaltend die in Tabellen 1 bis 176 angegebenen Verbindungen der allgemeinen Formel (I): Tabelle 1 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet.
Figure imgf000017_0001
Figure imgf000017_0002
Figure imgf000018_0001
Nr. X Y Z
62 Et 6-Et 4-CI
63 Et 6-Me 4-Br
64 Et 6-Et 4-Br
65 Et 6-Me 4-CI
66 Et 6-Me 4-Br
67 OMe 4-Me 6-CI
68 EtO 4-Me 6-CI
69 I H 4-Me
70 I 6-Me H
71 I 6-Et H
72 I 4-Me 6-Me
73 I 6-Et 4-Me
74 I 6-Me 4-CI
75 I 6-Et 6-CI
76 I 6-CI 4-Me
77 Me 4-I H
78 Et 4-I H
79 Et 4-I 6-Me
80 Et 4-I 6-Et
81 Cl 6-Me 4-I
82 Cl 6-Et 4-I
83 c-Pr H H
84 c-Pr 4-Me H
85 c-Pr H 6-Me
86 c-Pr 6-Et H
87 c-Pr 4-Me 6-Me
88 c-Pr 6-Et 4-Me
89 c-Pr 4-Me 6-CI
90 c-Pr 6-Et 4-CI
91 c-Pr 4-CI 6-Me
92 Me 4-c-Pr H
93 Et 4-c-Pr H
94 Me 4-c-Pr 6-Me
95 Et 4-c-Pr 6-Me
96 Et 4-c-Pr 6-Et
97 Cl 6-Me 4-c-Pr
98 Cl 6-Et 4-c-Pr
Figure imgf000020_0001
Figure imgf000021_0001
Tabelle 2: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000022_0001
Tabelle 3: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000022_0002
Tabelle 4: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000022_0003
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Isopropyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000023_0001
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B cyclo-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000023_0002
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B cyclo-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000023_0003
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B cyclo-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000024_0001
Tabelle 9: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für iso-Butyl, und B cyclo-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000024_0002
Tabelle 10: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und für iso-Propyl, und B cyclo-Butyl und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000024_0003
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2,2-Difluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000025_0001
Tabelle 12: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2,2-Difluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000025_0002
Tabelle 13: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B B 2,2-Difluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000025_0003
Tabelle 14: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 2,2-Difluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000026_0001
Tabelle 15: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2,2-Difluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000026_0002
Tabelle 16: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2,2,2-Trifluoroethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000026_0003
Tabelle 17: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2,2,2-Trifluoroethyl bedeuten und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000027_0001
Tabelle 18: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 2,2,2-Trifluoroethyl und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000027_0002
Tabelle 19: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für iso-Butyl steht, und B 2,2,2-Trifluoroethyl und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000027_0003
Tabelle 20: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2,2,2-Trifluoroethyl und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000028_0001
Tabelle 21 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B Benzyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000028_0002
Tabelle 22: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B Benzyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000028_0003
Tabelle 23: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B Benzyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000029_0001
Tabelle 24: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B Benzyl bedeutet, und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000029_0002
Tabelle 25: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl, und B Benzyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000029_0003
Tabelle 26: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000030_0001
Tabelle 27: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2-Chlorphenylmethyl und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000030_0002
Tabelle 28: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 2-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000030_0003
Tabelle 29: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 2-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000031_0001
Tabelle 30: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000031_0002
Tabelle 31 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 3-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000031_0003
Tabelle 32: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 3-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000032_0001
Tabelle 33: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 3-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000032_0002
Tabelle 34: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 3-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000032_0003
Tabelle 35: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 3-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000033_0001
Tabelle 36: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 4-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000033_0002
Tabelle 37: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 4-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000033_0003
Tabelle 38: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 4-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000034_0001
Tabelle 39: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 4-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000034_0002
Tabelle 40: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 4-Chlorphenylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000034_0003
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2-Phenylethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000035_0001
Tabelle 42: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2-Phenylethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000035_0002
Tabelle 43: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 2-Phenylethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000035_0003
Tabelle 44: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 2-Phenylethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000036_0001
Tabelle 45: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2-Phenylethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000036_0002
Tabelle 46: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2-(2-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000036_0003
Tabelle 47: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2-(2-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000037_0001
Tabelle 48: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2-(2-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000037_0002
Tabelle 49: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 2-(2-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000037_0003
Tabelle 50: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2-(2-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000038_0001
Tabelle 51 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B 2-(4-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000038_0002
Tabelle 52: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B 2-(4-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000038_0003
Tabelle 53: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B 2-(4-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000039_0001
Tabelle 54: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Butyl steht, und B 2-(4-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000039_0002
Tabelle 55: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für iso-Propyl steht, und B 2-(4-Chlorphenyl)-ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000039_0003
Tabelle 56: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B 4Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000040_0001
Tabelle 57: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000040_0002
Tabelle 58: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000040_0003
Tabelle 59: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Pentyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000041_0001
Tabelle 60: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Pentyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000041_0002
Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Pentyl steht, und B iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000041_0003
Tabelle 62: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Benzyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000042_0001
Tabelle 63: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Benzyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000042_0002
Tabelle 64: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A Benzyl steht, und B iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000042_0003
Tabelle 65: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 4-Fluorbenzyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000043_0001
Tabelle 66: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 4-Fluorbenzyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000043_0002
Tabelle 67: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 4-Fluorbenzyl steht, und B iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000043_0003
Tabelle 68: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Fluorbenzyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000044_0001
Tabelle 69: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Fluorbenzyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000044_0002
Tabelle 70: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Fluorbenzyl steht, und B iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000044_0003
Tabelle 71 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 3-Fluorbenzyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000045_0001
Tabelle 72: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 3-Fluorbenzyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000045_0002
Tabelle 73: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 3-Fluorbenzyl steht, und B iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000045_0003
Tabelle 74: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Phenylethyl steht, und B 4-Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000046_0001
Tabelle 75: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Phenylethyl steht, und B 4-Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000046_0002
Tabelle 76: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-Phenylethyl steht, und B 4-iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000046_0003
Tabelle 77: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(4-Chlorphenyl)-ethyl steht, und B 4-Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000047_0001
Tabelle 78: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(4-Chlorphenyl)-ethyl steht, und B 4-Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000047_0002
Tabelle 79: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(4-Chlorphenyl)-ethyl steht, und B 4-iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000047_0003
Tabelle 80: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(2-Chlorphenyl)-ethyl steht, und B 4-Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000048_0001
Tabelle 81 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(2-Chlorphenyl)-ethyl steht, und B 4-Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000048_0002
Tabelle 82: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A 2-(4-Chlorphenyl)-ethyl steht, und B 4-iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000048_0003
Tabelle 83: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(3-Chlorphenyl)-ethyl steht, und B 4-Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000049_0001
Tabelle 84: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(3-Chlorphenyl)-ethyl steht, und B 4-Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000049_0002
Tabelle 85: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für 2-(3-Chlorphenyl)-ethyl steht, und B 4-iso-Butyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000049_0003
Tabelle 86: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000050_0001
Tabelle 87: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B 2,2 Difluorethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000050_0002
Tabelle 88: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B 4-2,2,2 Trifluorethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000050_0003
Tabelle 89: Verbindungen der allgenneinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B Methyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000051_0001
Tabelle 90: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für c-Propyl steht, und B Ethyl bedeutet und X, Y und Z, die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000051_0002
Tabelle 91 : Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, und A und B jeweils Methyl bedeuten.
Figure imgf000051_0003
Tabelle 92: Verbindungen der allgenneinen Formel (I), worin G für Isopropylcarbo- nyl steht, und A und B jeweils Methyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000052_0001
Tabelle 93: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, und A und B jeweils Methyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000052_0002
Tabelle 94: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, und A und B jeweils Methyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000052_0003
Tabelle 95: Verbindungen der allgenneinen Formel (I), worin G für Butinyl steht, und A und B jeweils Methyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000053_0001
Tabelle 96: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, und A und B jeweils Methyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000053_0002
Tabelle 97: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000053_0003
Tabelle 98: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000054_0001
Tabelle 99: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000054_0002
Tabelle 100: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000054_0003
Tabelle 101 : Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000055_0001
Tabelle 102: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000055_0002
Tabelle 103: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000055_0003
Tabelle 104: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000056_0001
Tabelle 105: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000056_0002
Tabelle 106: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000056_0003
Tabelle 107: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000057_0001
Tabelle 108: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000057_0002
Tabelle 109: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000057_0003
Tabelle 1 10: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000058_0001
Tabelle 1 1 1 : Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000058_0002
Tabelle 1 12: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000058_0003
Tabelle 1 13: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000059_0001
Tabelle 1 14: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Ethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000059_0002
Tabelle 1 15: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000059_0003
Tabelle 1 16: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000060_0001
Tabelle 1 17: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000060_0002
Tabelle 1 18: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000060_0003
Tabelle 1 19: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000061_0001
Tabelle 120: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, und A und B jeweils Ethyl bedeuten und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000061_0002
Tabelle 121 : Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000061_0003
Tabelle 122: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000062_0001
Tabelle 123: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, und A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000062_0002
Tabelle 124: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000062_0003
Tabelle 125: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000063_0001
Tabelle 126: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Ethyl steht, und B iso-Butyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000063_0002
Tabelle 127: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für iso-Butyl steht, und B jeweils Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000063_0003
Tabelle 128: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für iso-Butyl steht, und B jeweils Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000064_0001
Tabelle 129: Verbindungen der allgemeinen Formel (I), worin G für Allyl steht, und A für iso-Butyl steht, und B jeweils Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000064_0002
Tabelle 130: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für iso-Butyl steht, und B jeweils Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000064_0003
131 : Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für iso-Butyl steht, und B jeweils Methyl und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000065_0001
Tabelle 132: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für iso-Butyl steht, und B jeweils Methyl und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000065_0002
Tabelle 133: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für iso-Butyl steht, und B jeweils Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000065_0003
Tabelle 134: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für iso-Butyl steht, und B jeweils Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000066_0001
Tabelle 135: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, und A für iso-Butyl steht, und B jeweils Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000066_0002
Tabelle 136: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für iso-Butyl steht, und B jeweils Ethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000066_0003
Tabelle 137: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für iso-Butyl steht, und B jeweils Ethyl und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000067_0001
Tabelle 138: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für iso-Butyl steht, und B jeweils Ethyl und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000067_0002
Tabelle 139: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A und B für iso-Butyl stehen, X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000067_0003
Tabelle 140: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A und B für iso-Butyl stehen, und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000068_0001
Tabelle 141 : Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A und B für iso-Butyl stehen, und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000068_0002
Tabelle 142: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A und B für iso-Butyl stehen, und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000068_0003
Tabelle 143: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A und B für iso-Butyl stehen, und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000069_0001
Tabelle 144: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A und B für iso-Butyl stehen, und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000069_0002
Tabelle 145: Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000069_0003
Tabelle 146: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000070_0001
Tabelle 147: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000070_0002
Tabelle 148: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für Methyl steht, B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000070_0003
Tabelle 149: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000071_0001
Tabelle 150: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für Methyl steht, und B cyclo-Propylmethyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000071_0002
Tabelle 151 : Verbindungen der allgemeinen Formel (I), worin G für Ethoxycarbonyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000071_0003
Tabelle 152: Verbindungen der allgemeinen Formel (I), worin G für Isopropylcarbo- nyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000072_0001
Tabelle 153: Verbindungen der allgemeinen Formel (I), worin G für Methylsulfonyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000072_0002
Tabelle 154: Verbindungen der allgemeinen Formel (I), worin G für Propinyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000072_0003
Tabelle 155: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000073_0001
Tabelle 156: Verbindungen der allgemeinen Formel (I), worin G für Butinyl steht, A für cyclo-Propylmethyl steht, und B Methyl bedeutet und X, Y und Z die in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000073_0002
Tabelle 157: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Wasserstoff steht, und B Ethyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000073_0003
Tabelle 158: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Wasserstoff steht, und B n-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000074_0001
Tabelle 159: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Wasserstoff steht, und B i-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000074_0002
Tabelle 160: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für Methyl steht und B Methyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000074_0003
Tabelle 161 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B Ethyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000075_0001
Tabelle 162: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B n-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben..
Figure imgf000075_0002
Tabelle 163: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Methyl steht, und B i-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000075_0003
Tabelle 164: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für Ethyl steht und B Methyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000076_0001
Tabelle 165: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B Ethyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000076_0002
Tabelle 166: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B n-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
H3
Figure imgf000076_0003
Tabelle 167: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Ethyl steht, und B i-Propyl bedeutet, und X, Y und Z die weils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000077_0001
Tabelle 168: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für Propyl steht und B Methyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000077_0002
Tabelle 169: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B Ethyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000077_0003
Tabelle 170: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B n-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000078_0001
Tabelle 171 : Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Propyl steht, und B i-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000078_0002
Tabelle 172: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, und A für i-Propyl steht und B Methyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000078_0003
Tabelle 173: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für i-Propyl steht, und B Ethyl bedeutet, und X, Y und Z die weils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000079_0001
Tabelle 174: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für i-Propyl steht, und B n-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000079_0002
Tabelle 175: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für Wasserstoff steht, und B Methyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000079_0003
Tabelle 176: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht, A für i-Propyl steht, und B i-Propyl bedeutet, und X, Y und Z die jeweils in Tabelle 1 angegebenen Bedeutungen haben.
Figure imgf000080_0001
Gegenstand der vorliegenden Erfindung sind auch Mischungen, umfassend Stereoisomere, die von Formel (I) oder von den Formeln der Komponente B (Safener) um- fasst sind. Solche Verbindungen der Formel (I) oder der Formeln der Komponente B (Safener) enthalten beispielsweise ein oder mehrere asymmetrisch substituierte Kohlenstoff-Atome oder Sulfoxide. Die durch ihre spezifische Raumform definierten möglichen Stereoisomeren, wie Enantiomere und Diastereomere, sind alle von der Formel (I) oder von den Formeln der Komponente B (Safener) umfasst und können nach üblichen Methoden aus Gemischen der Stereoisomeren erhalten oder auch durch stereoselektive Reaktionen in Kombination mit dem Einsatz von stereoche- misch reinen Ausgangs- oder Hilfsstoffen hergestellt werden.
Beispiele für als Herbizid (A) verwendete Verbindungen sind in den nachfolgenden Tabellen genannt, worin folgende Abkürzungen verwendet werden:
Benzyl c-Pr = cyclo- Propyl Ethyl iso-Butyl t-Bu = tertiär-Butyl iso-Propyl
Methyl Ph = Phenyl Tabelle 177: Verbindungen der allgemeinen Formel (I), worin G für Wasserstoff steht.
Nr. X Y Z A B Analytische Daten
l-a-1 Cl 4-CI H Me c-Butyl H-NMR, 400MHz, d6-DMSO, 7.68
(d, 1H); 7.45 (dd, 1H), 7.29 (d, 1H); 5.29 (qunitett, 1H); 2.40 (m, 2H), 2,28 (s, 3H), 2.19 (m ,2H), 1.75 (m, 2H)
l-a-2 Cl 4-CI 6-Et c-Pentyl Me H-NMR, 400MHz, d6-DMSO, 7.51
(d, 1H); 7.37 (d, 1H); 3.57 (s, 3H); 3.28 (m, 1H), 2.30 (m, 2H), 1.92 (m, 2H), 1.55 - 1.80 (m ,6H), 1.00 (t, 3H) l-a-3 Cl 4-CI 6-Et Me Benzyl H-NMR, 400MHz, d6-DMSO,
10.50 (s, breit), 7.52 (s, 1H), 7.18- 7.37 (m, 5H), 5.2 (s, 2H), 2.33 (q, 2H), 2.22 (s, 3H), 1.00 (t, 3H) l-a-4 Cl 4-Me 6-Me Me c-Pr-CH2 H-NMR, 400MHz, d6-DMSO, 7.08
(d, 1H); 6.93 (d, 1H); 3.72 (d, 2H); 2.25 (s, 3H), 2.15 (s, 3H), 2.02 (d, 3H), 1.00 (m ,1H), 0.40 (m, 2H), 0.22 (m, 2H)
l-a-5 Cl 6-CI H c-Pentyl Me H-NMR, 400MHz, d6-DMSO, 10.7
(bs, 1H), 7.52 (d, 2H); 7.44 (d, 1H); 3.56 (s, 3H); 3.30 (m, 1H), 2.30 (m, 2H), 1.94 (m, 2H), 1.55-1.80 (m ,6H)
l-a-6 Cl 4-CI 6-Et Me 0P1--CH2 H-NMR, 400MHz, d6-DMSO, 10.5
(bs, 1H), 7.51 (d, 1H); 7.35 (d, 1H); 3.88 (d, 2H); 2.33 (m, 2H), 2.25 (s, 3H), 1.22 (m, 1 H), 1.03 (t ,3H), 0.45 (m, 2H), 0.32 (m, 2H)
l-a-7 Cl 6-CI H Me 2-Phenyl- H-NMR, 400MHz, d6-DMSO, 10.8 ethyl (bs, 1H), 7.52 (d, 2H); 7.42 (t, 1H);
7.28-7.12 (m, 5H), 4.22 (t, 2H); 2.98 (t, 2H), 2.22 (s, 3H),
l-a-8 Cl 6-CI H Me 2-(2-Chlor- H-NMR, 400MHz, d6-DMSO, 10.8 phenyl)- (bs, 1H), 7.52 (d, 2H); 7.42 (m, 3H); ethyl 7.20 (m, 2H), 4.25 (t, 2H); 3.11 (t,
2H), 2.15 (s, 3H),
l-a-9 I H H Me 2-Phenyl- H-NMR, 400MHz, d6-DMSO, 10.4 ethyl (bs, 1H), 7.91 (d, 1H), 7.43 (t, 1H);
7.27 (m, 2H); 7.23 - 7.10-(m, 5H), 4.18 (m, 2H); 2.98 (t, 2H), 2.21 (s, 3H), Nr. X Y Z A B Analytische Daten l-a-10 I H H Me 2-(2-Chlor- H-NMR, 400MHz, d6-DMSO, 10.4 phenyl)- (bs, 1H), 7.90 (d, 1H), 7.41 (m, 2H); ethyl 7.27 (m, 3H); 7.12 (m, 2H), 4.22 (m,
2H); 3.11 (m, 2H), 2.16 (s, 3H), l-a-11 Cl 4-CI 6-Et c-Hexyl-CH.2 Me H-NMR, 400MHz, d6-DMSO, 7.53
(d, 1H); 7.37 (d, 1H); 3.58 (s, 3H); 2.50 (m, 2H, lösungsmittel überlagert), 2.30 (m, 2H), 1.70 (m, 6H), 1.30 - 0.90 (Signalhaufen, 9H) l-a-12 Cl 4-CI H c-Pentyl-CH.2 Me H-NMR, 400MHz, d6-DMSO, 10.4
(bs, 1H), 7.70 (s, 1H), 7.41 (dd, 1H); 7.31 (d, 1H); 3.58 (s, 3H), 2.63 (d, 2H);2.24 (m, 1H), 1.8-1.2 (Signalhaufen, 8H),
l-a-13 Cl 6-CI 4-CI Me Bz H-NMR, 400MHz, d6-DMSO, 7.65
(s, 2H); 7.22-7.34 (m, 5H); 5,18 (s, 2H); 2,21 (s, 3H)
l-a-14 Cl 6-F 3-Me Me Bz H-NMR, 400MHz, d6-DMSO, 7.23- 7.34 (m, 7H); 5,18 (s, 2H); 2,24 (s, 6H)
l-a-15 F 6-F 3-F Me Bz H-NMR, 400MHz, d6-DMSO, 7.49
(ddd, 1H); 7.24-7.34 (m, 5H); 7.10- 7.16 (m, 1H); 5,18 (s, 2H); 2,25 (s, 3H)
l-a-16 EtO 6-F 3-F Me Bz H-NMR, 600MHz, d6-DMSO, 7.24- 7.38 (m, 6H), 7.02 (ddd, 1H), 5.28 (d, 1H), 5.11 (d, 1H), 4.02 (qd, 1H), 3.94 (qd, 1H), 2,24 (s, 3H), 1.03 (t, 3H) l-a-17 F 6-F 3-EtO Me Bz H-NMR, 400MHz, d6-DMSO, 7.15- 7.34 (m, 6H), 6.97-7.02 (m, 1H), 5.17 (s, 2H), 4.11 (q, 2H), 2,24 (s, 3H), 1.34 (t, 3H)
l-a-18 F H 5-CI Me Bz H-NMR, 400MHz, d6-DMSO, 7.4I- 7.45 (m, 1H), 7.24-7.37 (m, 7H), 5.16 (s, 2H), 2.23 (s, 3H)
l-a-19 Cl 6-CI H c-Hexyl-CH.2 Me H-NMR, 400MHz, d6-DMSO, 7.52
(d, 2H); 7.42 (dd, 1H); 3.58 (s, 3H); 2.50 (m, 2H,
lösungsmittelüberlagert), 2.30 (m, 2H), 1.70 (m, 6H), 1.20 (m, 3H), 0.97 (m, 3H)
l-a-20 Cl 6-CI H Me 2-(4-Chlor- H-NMR, 400MHz, d6-DMSO, 10.8 phenyl)- (bs, 1H), 7.52 (d, 2H), 7.44 (dd, 1H); ethyl 7.30 (m, 2H), 7.18 (d, 2H); 4.22 (t,
2H); 2.98 (t, 2H), 2.21 (s, 3H), l-a-21 Cl 4-CI H Me 2-(4- H-NMR, 400MHz, d6-DMSO, 10.6
Chlorphe- (bs, 1H), 7.70 (s, 1H), 7.47 (dd, 1H); nyl)-ethyl 7.32 (m, 2H), 7.26 (d, 1H), 7.18 (d,
2H); 4.18 (m, 2H); 2.98 (t, 2H), 2.21 (s, 3H), Nr. X Y Z A B Analytische Daten
l-a-22 Cl 4-CI H Me 2-(2-Chlor- H-NMR, 400MHz, d6-DMS0, 10.6 phenyl)- (bs, 1H), 7.70 (s, 1H), 7.47 (dd, 1H); ethyl 7.40 (m, 1H), 7.22 (m, 4H); 4.22 (m,
2H); 3.11 (t, 2H), 2.17 (s, 3H), l-a-23 F 6-F H Me Bz H-NMR, 400MHz, d6-DMS0, 7.43- 7.51 (m, 1H); 7.23-7.33 (m, 6H); 7.06-7.12 (m, 1H); 5.18 (s, 2H); 2.25 (s, 3H)
l-a-24 Cl 6-F 4-F Me Bz Öl
l-a-25 Cl 6-F H Me Bz H-NMR, 400MHz, d6-DMS0, 7.15- 7.48 (m, 8H) ; 5.24 (d, 1H) ; 5.18 (d, 1H) ; 2.25 (s, 3H)
l-a-26 Cl 6-CF3 H Me 2-Phenyl- H-NMR, 400MHz, CDCI3, 7.68 (d, ethyl 2H), 7.47 (t, 1H); 7.21 (m, 5H); 6.20
(bs, 1H),4.28 (m, 2H); 3.06 (t, 2H), 2.28 (s, 3H),
l-a-27 I H H Me 2-(4-Chlor- H-NMR, 400MHz, CDCI3, 7.99 (d, phenyl)- 2H), 7.47 (t, 1H); 7.20 (m, 6H); 5.60 ethyl (bs, 1H),4.32 (m, 2H); 3.08 (t, 2H),
2.32 (s, 3H),
l-a-28 Cl 4-CI 6-Et c-Pentyl-CH.2 Me H-NMR, 400MHz, d6-DMS0, 10.4
(bs, 1H), 7.52 (d, 1H), 7.37 (d, 1H); 3.58 (s, 3H), 2.58 (d, 2H); 2.31 (m, 2H), 2.22 (m, 1H), 1.8-1.2 (Signalhaufen, 8H), 1.03 (t, 3H) l-a-29 Cl 6-CI H c-Pentyl-CH.2 Me H-NMR, 400MHz, d6-DMS0, 10.7
(bs, 1H), 7.52 (d, 2H), 7.41 (dd, 1H); 3.58 (s, 3H), 2.63 (d, 2H); 2.23 (m, 1 H), 1.8 - 1.2 (Signalhaufen, 8H), l-a-30 Cl 6-CI H c-Pr Me H-NMR, 400MHz, CDCI3, 7.45 (d,
2H), 7.33 (t, 1H); 5.80 (bs, 1H),3.72 (s, 3H); 2.05 (m, 1H), 0.95 (m, 4H), l-a-31 H 3-CF3 H 0P1--CH2 Me
l-a-32 Cl 6-CI H 0P1--CH2 Me
l-a-33 Cl 4-CI H 0P1--CH2 Me
l-a-34 H 3-CF3 H c-Pr-CH2 i-Pr
l-a-35 H 2-CI H c-Pr-CH2 i-Pr
l-a-36 Cl 6-CI H C-P1--CH2 i-Pr
l-a-37 Cl 6-F H Me Me 1H-NMR, 400MHz, d6-DMS0, 10.88
(bs, 1H), 7.48 (m, 1H), 7.40 (dd, 1H), 7.27 (t, 1H) 3,58 (s, 3H), 2,23 (s, 3H) l-a-38 N02 H H Me Me 1H-NMR, 400MHz, d6-DMS0, 10.7
(bs, 1H), 8.10 (d, 1H), 7.78 (t, 1H), 7.62 (t, 1H), 7.45 (d, 1H) 3,53 (s, 3H), 2,28 (s, 3H)
l-a-39 Cl 3-CI H Me Me 1H-NMR, 400MHz, d6-DMS0, 10.58
(bs, 1H), 7.58 (d, 1H), 7.42 (t, 1H), 7.25 (d, 1H) 3,58 (s, 3H), 2,21 (s, 3H) Nr. X Y Z A B Analytische Daten
l-a-40 H 4-CI 3-CI H Me Fp.: 315 °C
l-a-41 Cl H 4-CI H t-Bu Fp.: 250 °C
l-a-42 Cl 6-CI H Me Me 1 H-NMR, 400MHz, d6-DMSO, 10.8
(bs, 1 H), 7.52 (pseudo d, 2H), 7.43 (t, 1 H), 3,58 (s, 3H), 2,23 (s, 3H) l-a-43 H 3-Ph H H t-Bu Fp.: 244 °C
l-a-44 H 5-CF3 3-CF3 H t-Bu Fp.: 239 °C
l-a-45 Cl 4-Me 6-Br Me Me 1 H-NMR, 400MHz, d6-DMSO, 10.65
(bs, 1 H), 7.52 (s, 1 H), 7.38 (s, 1 H), 3,57 (s, 3H), 2,33 (s, 3H), 2,23 (s, 3H)
l-a-46 Cl 5-(4- H H t-Bu
Cl-
Ph) Fp.: 250 °C
l-a-47 Br 4-Me Br Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.56
(s, 2H), 3,58 (s, 3H), 2.32 (s, 3H), 2,23 (s, 3H)
l-a-48 Cl H 3-CI H t-Bu amorphes Pulver
l-a-49 Cl 6-CI H i-Bu Me 1 H-NMR, 400MHz, d6-DMSO, 10.8
(bs, 1 H), 7.52 (d, 2H), 7.43 (t, 1 H), 3,56 (s, 3H), 2.51 (m, 2H, überlegert durch LM), 2,03 (m, 1 H), 0.90 (d, 6H)
l-a-50 Cl 4- 6-CI Me Me 1 H-NMR, 400MHz, d6-DMSO, 1 1.0
OCF3 (bs, 1 H), 7.72 (s, 2H), 3,58 (s, 3H),
2,23 (s, 3H)
l-a-51 Cl 4-Me 6-c-Pr Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.07
(s, 1 H), 6.82(s, 1 H), 3,53 (s, 3H), 2,40 (s, 3H), 2,28 (s, 3H), 1.81 (m, 1 H), 0.89 (m, 2H), 0.63 (m, 2H) l-a-52 Cl 4-Me 6-OCF3 Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.42
(s, 1 H), 7.23 (s, 1 H), 3,56 (s, 3H), 2,41 (s, 3H), 2,22 (s, 3H) l-a-53 F 3-Me 6-F Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.37
(q, 1 H), 7.03 (t, 1 H), 3,56 (s, 3H), 2,23 (pseudo d, 6H)
l-a-54 Cl 3-Me 6-F Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.37
(t, 1 H), 7.12 (t, 1 H), 3,52 (s, 3H), 2,32 (s, 3H), 2,23 (s, 3H) l-a-55 F 3- 6-F Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.17
OMe (m, 1 H), 7.02 (t, 1 H), 3.82 (s, 3H),
3,54 (s, 3H), 2,18 (s, 3H) l-a-56 Cl 4-Br 6-CI Me Me 1 H-NMR, 400MHz, d6-DMSO, 7.82
(s, 2H), 3,54 (s, 3H), 2,21 (s, 3H) l-a-57 F 6-F H Me H 1 H-NMR, 400MHz, d6-DMSO, 7.50
(m, 1 H), 7.12 (m, 1 H), 2,23 (pseudo d, 6H) Nr. X Y Z A B Analytische Daten
l-a-58 Cl 6- H Me Me 1H-NMR, 400MHz, d6-DMSO, 10.75
CF3 (bs, 1H), 7.88 (d, 1H), 7.81 (d, 1H),
7.67 (t, 1H), 3,56 (s, 3H), 2,23 (s, 3H)
l-a-59 Cl 4-CI 6-Br Me Me 1H-NMR, 400MHz, d6-DMSO, 10.75
(bs, 1H), 7.88 (s, 1H), 7.68 (t, 1H), 3,58 (s, 3H), 2,23 (s, 3H) l-a-60 F 3-F H Me Me 1H-NMR, 400MHz, d6-DMSO, 10.8
(bs, 1H), 7.43 (m, 1H), 7.23 (m, 1H), 7.11 (m, 1H), 3,58 (s, 3H), 2,22 (s, 3H)
l-a-61 OCF3 4-Br 6-Br Me Me 1H-NMR, 400MHz, d6-DMSO, 7.92
(s, 1H), 7.59 (s, 1H), 3,48 (s, 3H), 2,11 (s, 3H)
l-a-62 I H H Me Me 1H-NMR, 400MHz, d6-DMSO, 7.92
(d, 1H), 7.42 (t, 1H), 7.15 (m, 2H), 3,56 (s, 3H), 2,24 (s, 3H) l-a-63 Cl 4-CI H Me Me 1H-NMR, 400MHz, d6-DMSO, 10.54
(bs, 1H), 7.72 (d, 1H), 7.48 (dd, 1H), 7.16 (d, 1H) 3,58 (s, 3H), 2,23 (s, 3H)
l-a-64 H 4-CI H Me Me 1H-NMR, 400MHz, d6-DMSO, 10.4
(bs, 1 H), 7.50 (pseudo s, 4 H), 3,59 (s, 3H), 2,24 (s, 3H)
l-a-65 H 3-CI H Me Me 1H-NMR, 600MHz, d6-DMSO, 10.4
(bs, 1H), 7.47 (m, 3H) 7.39 (d, 2 H), 3,61 (s, 3H), 2,27 (s, 3H) l-a-66 H 3-CF3 H Me Me 1H-NMR, 400MHz, CDCI3, 10.54 (bs,
1H), 7.72 (d, 1H), 7.75-7.55 (m, 4H), 3,71 (s, 3H), 2,31 (s, 3H) l-a-67 Cl H H Me Me 1H-NMR, 600MHz, d6-DMSO, 10.4
(bs, 1H), 7.49 (m, 2H) 7.44 (d, 2 H), 7.41 (d, 2 H), 3,59 (s, 3H), 2,24 (s, 3H)
l-a-68 Cl 6-F H Me H 1H-NMR400 MHz, d6-DMSO : 12.27 ppm (s breit, 1H), 7.4I-7.47 (m, 1H); 7.36 (d, 1H); 7.19-7.23 (m, 1H); 2.22 (s, 3H)
l-a-69 Cl 6-F 4-F Me H Öl
l-a-70 Cl 6-CI 4-CI Me H 1H-NMR400 MHz, d6-DMSO : 12.27 ppm ((s breit, 1H), 7.66 (s, 2H); 2.20 (s, 3H)
l-a-71 Cl 6-F 3-Me Me H 1H-NMR400 MHz, d6-DMSO : 12.27 ppm (s breit, 1H), 7.23-7.33 (m, 2H); 2.49 (s, 3H); 2.48 (s, 3H) l-a-72 F 6-F 3-F Me H 1H-NMR400 MHz, d6-DMSO : 12.38 ppm (s breit, 1H), 7.50 (ddd, 1H); 7.10-7.16 (m, 1H); 2.22 (s, 3H), Nr. X Y Z A B Analytische Daten
l-a-73 Me 6-Me 3-Br H Me H-NMR (400 MHz, d6-DMSO, Shift in ppm): 1 1.1 (bs, 1 H), 7.81 (s, 1 H), 7.49 (d, 1 H), 7,02 (d, 1 H), 3,63 (s, 3H), 2,23 (s, 3H), 2.07 (s, 3H), 1.96 (s, 3H)
l-a-74 Me 5-Me 4-OMe H t-Bu Fp.: 274 °C
l-a-75 H 4-CI 3-CI H t-Bu Fp.: 315 °C
l-a-76 Cl H 4-CI H t-Bu Fp.: 250 °C
l-a-77 Cl 6-CI H Me Me
l-a-78 H 3-Ph H H t-Bu Fp.: 244 °C
H 5- 3-CF3 H t-Bu
l-a-79 CF3 Fp.: 239 °C
Me H 5-(4-CI- H t-Bu
l-a-80 Ph) Fp.: 255 °C
Cl 5-(4- H H t-Bu
Cl- l-a-81 Ph) Fp.: 250 °C
l-a-82 Me Cl H H t-Bu Fp.: 235 °C
l-a-83 Cl 6-Et 4-CI Me Me H-NMR, 400MHz, d6-DMSO, 10.5
(bs, 1 H), 7.52 (d, 1 H), 7.37 (d, 1 H), 3,56 (s, 3H), 2.33 (q, 2H), 2,23 (s, 3H), 2.07 (s, 3H), 1.00 (t, 3H) l-a-84 Me 6-Me 3-(4-F- H Me H-NMR, 400MHz, d6-DMSO, 1 1.0
Ph) (bs, 1 H), 7.83 (s, 1 H) 7.52 (d, 1 H),
7.37 - 7.23 (m, 4 H), 7.14 (d, 1 H), 7.08 (d, 1 H), 3,64 (s, 3H), 2.02 (s, 3H), 1.88 (s, 3H)
l-a-85 OMe 6-Et 4-CI Me Me H-NMR, 400MHz, CDCI3, 6.99 (d,
1 H) 6.84 (d, 1 H), 5.40 (bs, 1 H), 3,74 (pseudo-s, 6H), 2.40 (m, 2H), 2.33 (s, 3H), 1.08 (t, 3H) l-a-86 Br 6-Et 4-Me Me Me H-NMR, 400MHz, d6-DMSO, 10.3
(bs, 1 H), 7.36 (d, 1 H), 7.10 (d, 1 H), 3,57 (s, 3H), 2.33 (s, 3H), 2.27 (q, 2H), 2,23 (s, 3H), 0.98 (t, 3H) l-a-87 Me 6-Me 3-(4-CI- H Me H-NMR, 400MHz, d6-DMSO, 1 1.0
Ph) (bs, 1 H), 7.81 (s, 1 H), 7.48 (d, 2H),
7.32 (d, 2H), 7.15 (d, 1 H), 7.08 (d, 1 H), 7.08 (d, 1 H), 3,63 (s, 3H), 1.99 (s, 3H), 1.89 (s, 3H) l-a-88 Me 6-Br 4-CI Me Me H-NMR (400 MHz, DMSO-d6): 7.67
(d, 1 H), 7.44 (d, 1 H), 3.59 (s, 3H), 2.23 (s, 3H), 2.04 (s, 3H) l-a-89 Et 6-CI 4-Br Me Me H-NMR (400 MHz, DMSO-d6): 7.62
(d, 1 H), 7.50 (d, 1 H), 3.58 (s, 3H), 2.33 (m, 2H), 2.21 (s, 3H), 1.03 (dt, 3H) Nr. X Y Z A B Analytische Daten
l-a-90 Et 6-Br 4-CI Me Me H-NMR (400 MHz, DMSO-d6): 7.65
(d, 1 H), 7.40 (d, 1 H), 3.56 (s, 3H), 2.33 (m, 2H), 2.23 (s, 3H), 1.02 (dt, 3H)
l-a-91 Me 6-CI 4-Br Me Me H-NMR (400 MHz, DMSO-d6): 7.49
(d, 1 H), 7.38 (d, 1 H), 3.72 (s, 3H), 2.21 (s, 3H), 2.18 (t, 3H) l-a-92 Et 6-CI 4-I Me Me H-NMR (400 MHz, DMSO-d6): 7.74
(d, 1 H), 7.62 (d, 1 H), 3.56 (s, 3H), 2.30 (m, 2H), 2.23 (s, 3H), 1.00 (dt, 3H)
l-a-93 Et 6-I 4-CI Me Me H-NMR (400 MHz, DMSO-d6): 7.82
(d, 1 H), 7.40 (d, 1 H), 3.58 (s, 3H), 2.33 (m, 2H), 2.23 (s, 3H), 0.99 (dt, 3H)
l-a-94 Me 6-Me 4-CI Me Me H-NMR (400 MHz, d6-DMSO, Shift in ppm): 10.8 (bs, 1 H), 7,19 (s, 2H), 3,59 (s, 3H), 2,23 (s, 3H), 1.97 (s, 6H)
l-a-95 Et 4-Ph 6-Et Me Me
l-a-96 Et 4-CI 6-Et Me Me l-a-97 Et 4- 6-Et Me Me
OMe
l-a-98 Et 4-Br 6-Et Me Me
l-a-99 Et 4-CN 6-Et Me Me
l-a-100 Et 4-CF3 6-Et Me Me
l-a-101 Et 4- 6-Et Me Me
OCF3
l-a-102 Et 4-cPr 6-Et Me Me
l-a-103 Et 4-(4- 6-Et Me Me
Me-
Ph)
l-a-104 Me 5-(4- H Me Me
Cl-
Ph)
l-a-105 Me 4-Me 6-Br Me Me
l-a-106 Cl 4-CI 6-Et c-Pr Me H-NMR (400 MHz, d6-DMSO, Shift in ppm): 10.65 (bs, 1 H), 7,52 (d, 1 H), 7.38 (d, 1 H), 3,53 (s, 3H), 2,33 (m, 2H), 2.18 (m, 1 H), 1.04 (t, 3H), 0.89 (m, 4H)
l-a-107 Cl 3-CI 6-CF3 Me Me H-NMR (400 MHz, d6-DMSO, Shift in ppm): 10.9 (bs, 1 H), 7,93 (m, 1 H), 7.81 (m, 1 H), 3,54 (s, 3H), 2,21 (s, 3H) Tabelle 178: Verbindungen der allgemeinen Formel (I), worin G für C(=O)R1 steht.
Figure imgf000088_0001
Nr. X Y Z R1 A B Analytische Daten
l-b-1 Cl 6-F H i-Pr Me Me 1H-NMR, 400MHz, d6-DMSO, 7.53 (m,
1H), 7.47 (d, 1H), 7.35 (t, 1H) 3,71 (s, 3H), 2.65 (m, 1H), 2,20 (s, 3H), 0.88 (m, 6H)
l-b-2 H 3-CI 4-CI i-Pr Me H 89 °C
l-b-3 Cl 6-CI H i-Pr Me Me 1H-NMR, 400MHz, d6-DMSO, 7.60
(pseudo d, 2H), 7.50 (t, 1H), 3,72 (s, 3H), 2.62 (m, 1H), 2,20 (s, 3H), 0.86 (d, 6H) l-b-4 NO H H i-Pr Me Me 1H-NMR, 400MHz, d6-DMSO, 8.20 (d,
2 1H), 7.88 (t, 1H), 7.72 (t, 1H), 7.38 (d,
1H) 3,67 (s, 3H), 2.65 (m, 1H), 2,19 (s, 3H), 0.92 (m, 6H)
l-b-5 F 3-F H i-Pr Me Me 1H-NMR, 400MHz, d6-DMSO, 7.55 (m,
1H), 7.30 (m, 1H), 7.07 (m, 1H), 3,70 (s, 3H), 2.68 (m, 1H), 2,19 (s, 3H), 0.93 (m, 6H)
l-b-6 Cl 4-Me 6-Br i-Pr Me Me 1H-NMR, 400MHz, d6-DMSO, 7.58 (s,
1H), 7.44 (s, 1H), 3,71 (s, 3H), 2,31 (s, 3H), 2,19 (s, 3H)
l-b-7 Cl 4-OCF3 6-CI i-Pr Me Me 1H-NMR, 400MHz, CDCI3, 7.32 (s, 2H),
3,85 (s, 3H), 2.62 (m, 1H), 2,28 (s, 3H), 1.01 (d, 6H)
l-b-8 Br 4-Me 6-Br i-Pr Me Me 1H-NMR, 400MHz, CDCI3, 7.41 (s, 2H),
3,82 (s, 3H), 2.58 (m, 1H), 2.32 (s, 3H), 2,25 (s, 3H), 0.99 (d, 6H)
l-b-9 Cl 3-CI H i-Pr Me Me 1H-NMR, 400MHz, CDCI3, 7.50 (d, 1H),
7.25 (t, 1H), 7.09 (d, 1H) 3,82 (s, 3H), 2.57 (m, 1H), 2,25 (s, 3H), 1.00 (dd, 6H) l-b-10 Cl 4-Me 6- i-Pr Me Me 1H-NMR, 400MHz, CDCI3, 7.21 (s, 1H),
OCF3 7.02 (s, 1H), 3,75 (s, 3H), 2.57 (m, 1H),
2,38 (s, 6H), 0.99 (m, 6H)
l-b-11 F 3-Me 6-F Et Me Me 1H-NMR, 400MHz, d6-DMSO, 7.43 (m,
1H), 7.12 (t, 1H), 3,68 (s, 3H), 2.40 (t, 1H), 2,21 (s, 6H), 0.89 (m, 6H) l-b-12 Cl 3-Me 6-F Me Me Me 1H-NMR, 400MHz, d6-DMSO, 7.52 (m,
1H), 7.22 (t, 1H), 3,70 (s, 3H), 2.32 (s, 3H), 2,22 (s, 3H), 2.09 (s, 3H) Nr. X Y Z R1 A B Analytische Daten l-b-13 Cl 4-Br 6-CI i-Pr Me Me 1 H-NMR, 400MHz, d6-DMS0, 7.96 (s,
2H), 3,72 (s, 3H), 2.70 (m, 1 H), 2,23 (s, 3H), 0.92 (m, 6H)
l-b-14 Cl 4-CI 6-Br Me Me Me 1 H-NMR, 400MHz, d6-DMS0, 7.96 (d,
1 H), 7.88 (d, 1 H), 3,71 (s, 3H), 2,23 (s, 3H), 2.12 (s, 3H)
l-b-15 Cl 4-Me 6-c-Pr Me Me Me 1 H-NMR, 400MHz, d6-DMS0, 7.58 (d,
1 H), 7.22 (d, 1 H), 3,68 (s, 3H), 2.29 8s, 3H), 2,21 (s, 3H), 2.05 (s, 3H) l-b-16 Me 6-Br 4-CI i-Pr Me Me H-NMR (400 MHz, DMSO-d6): 7.71 (d,
1 H), 7.47 (d, 1 H), 3.71 (s, 3H), 2.63 (m, 1 H), 2.20 (s, 3H), 2.07 (s, 3H), 0.88 (dd, 6H)
l-b-17 Et 6-Br 4-CI i-Pr Me Me H-NMR (400 MHz, DMSO-d6): 7.72 (d,
1 H), 7.48 (d, 1 H), 3.71 (s, 3H), 2.61 (m, 1 H), 2.32, (q, 2H), 2.20 (s, 3H), 1.04 (t, 3H), 0.87 (dd, 6H)
l-b-18 Et 6-CI 4-I Me Me Me H-NMR (400 MHz, DMSO-d6): 7.81 (d,
1 H), 7.68 (d, 1 H), 3.71 (s, 3H), 2.61 (m, 1 H), 2.32, (q, 2H), 2.22 (s, 3H), 2.07 (s, 3H)
l-b-19 Cl 6-CI H Me c- Me H-NMR, 400MHz, CDCI3, 7.39 (d, 2H);
Pentyl 7.30 (d, 1 H); 3.82 (s, 3H); 3.03 (m, 1 H),
2.02 (s, 3H), 1.60 - 1.94 (Signalhaufen, 8H)
l-b-20 Cl 4-CI 6-Et i-Pr c- Me H-NMR, 400MHz, CDCI3, 7.32 (d, 1 H);
Pentyl 7.22 (d, 1 H); 3.82 (s, 3H); 2.99 (m, 1 H),
2.47 (m, 2H), 1.60 - 2.05 (Signalhaufen, 8H), 1.16 (t, 3H), 0.95 (dd, 6H) l-b-21 Cl 6-CI H i-Pr i-Bu Me 1 H-NMR, 400MHz, CDCI3, 7.39 (d, 2H),
7.28 (t, 1 H), 3,87 (s, 3H), 2.53 (m, 1 H), 2.42 (d, 2H), 2,06 (m, 1 H), 0.96 (m, 12H) l-b-22 Et 6-OMe 4-CI Me Me Me H-NMR (400MHz, CDCI3, Shift in ppm):
6.93 (d, 1 H) 6.78 (d, 1 H), 5.40 (bs, 1 H), 3.81 (s, 3H), 3,70 (s, 6H), 2.37 (m, 2H), 2.25 (s, 3H), 2.00 (s, 3H), 1.1 1 (t, 3H) l-b-23 Et 4-Ph Et Me Me Me
l-b-24 Et 4-(4-Me- Et Me Me Me
Ph)
l-b-25 Me 5-(4-CI- H Me Me Me
Ph) Tabelle 179: Verbindungen der allgemeinen Formel (I), worin G für C(=L)MR2 steht
Figure imgf000090_0001
Nr. X Y Z A B L M R2 Analytische Daten l-c-1 Cl 6-CI H Me 2- 0 0 Et H-NMR, 400MHz, CDCI3, 7.39
Phenyl- (d, 2H); 7.18 - 7.32 ethyl (Signalhaufen, 6H); 4.42 (m,
2H); 4.17 (q, 2H), 3.15 (m, 2H), 2.31 (s, 3H), 1.22 (q, 3H) l-c-2 Cl 4-CI H Me 2- 0 0 Et H-NMR, 400MHz, CDCI3, 7.52
Phenyl- (d, 1 H); 7.15 - 7.35 ethyl (Signalhaufen, 7H); 4.40 (m,
2H); 4.15 (q, 2H), 3.13 (m, 2H), 2.31 (s, 3H), 1.22 (q, 3H) l-c-3 Cl 6-CI H Me 2-(2'- 0 0 Et H-NMR, 400MHz, CDCI3, 7.10
Cl- - 7.40 (Signalhaufen, 7H); 4.48
Pheny- (m, 2H); 4.18 (m, 2H), 3.28 (m, lethyl 2H), 2.29 (s, 3H), 1.21 (q, 3H) l-c-4 Cl 6-Et 4-CI Me c-Pr- 0 0 Et H-NMR, 400MHz, d6-DMSO,
CH2 7.60 (d, 1 H); 7.43 (d, 1 H);
4.13 (q, 2H), 3.99 (d, 2H); 2.35 (m, 2H), 2.28 (s, 3H), 1.22 (m, 1 H), 1 ,08 (t, 3H), 1.03 (t ,3H), 0.48 (m, 2H), 0.36 (m, 2H)
l-c-5 Cl 6-CI H c- Me 0 0 Et H-NMR, 400MHz, CDCI3),
Pentyl 7.39 (d, 2H); 7.29 (d, 1 H); 4.1 1
8q, 2H), 3.83 (s, 3H); 3.12 (m, 1 H), 1.96 (m, 2H), 1.82 (m, 4H), 1.65 (m ,2H), 1.13 (t, 3H) l-c-6 Cl 6-Et 4-CI c- Me 0 0 Et H-NMR, 400MHz, CDCI3 7.32
Pentyl (d, 1 H); 7.22 (d, 1 H); 4.08 (q,
2H), 3.83 (s, 3H); 3.08 (m, 1 H), 2.47 (m, 2H), 1.98 (m, 2H), 1.80 (m, 4H), 1.65 (m ,2H), 1.15 (m, 6H)
l-c-7 Cl 6-CI H Me c-Pr- 0 0 Et H-NMR, 400MHz, d6-DMSO,
CH2 7.62 (m, 2H); 7.52 (t, 1 H); 4.36
(m, 1 H), 4.13 (m, 2H), 3.99 (m, 1 H); 2.28 (s, 3H), 1.30 - 1.00 (Signalhaufen, 4H), 0.52 (m, 2H), 0.40 (m, 2H) l-c-8 I H H Me 2- 0 0 Et H-NMR, 400MHz, CDCI3 7.92
Phenyl- (d, 1 H); 7.39 (t, 1 H); 7.30 - ethyl 7.05 (Signalhaufen, 7H), 4.40
(m, 2H), 4.13 (q, 2H), 3.13 (t, 2H), 2.30 (s, 3H), 1.18 (m, 6H)
Figure imgf000091_0001
Nr. X Y Z A B L M R2 Analytische Daten l-c-18 Cl 6-Et 4-CI c- Me 0 0 Et H-NMR, 400MHz, CDCI37.32
Pen- (d, 1H); 7.21 (d, 1H); 4.12 (m, tyl- 2H), 3.82 (s, 3H); 2.62 (d, 2H),
CH2 2.45 (m, 2H), 2.28 (m, 1H),
1.70 (m,4H), 1.40-1.10 (Signalhaufen, 10H), l-c-19 Cl 6-CI H c- Me 0 0 Et H-NMR, 400MHz, CDCI3),
Pen- 7.39 (d, 2H); 7.29 (d, 1H); 4.11 tyl- (q, 2H), 3.83 (s, 3H); 2.62 (d,
CH2 2H), 2.45 (m, 2H), 2.28 (m,
1H), 1.70 (m,4H), 1.55 (m, 1H), 1.40- 1.10 (Signalhaufen, 5H),
l-c-20 Cl 4-CI H c- Me 0 0 Et H-NMR, 400MHz, CDCI3),
Pen- 7.49 (d, 1H); 7.32 (dd, 1H), tyl- 7.18 (d, 1H); 4.12 (q, 2H), 3.83
CH2 (s, 3H); 2.62 (d, 2H), 2.45 (m,
2H), 2.28 (m, 1H), 1.70 (m, 4H), 1.55 (m, 1H), 1.40-1.10 (Signalhaufen, 5H), l-c-21 I H H Me 2-(4-CI- 0 0 Me H-NMR, 400MHz, CDCI37.93 phe- (d, 1H); 7.41 (t, 1H); 7.35-7.20 nyl)- (Signalhaufen, 5 H), 7.16 (d, ethyl 2H), 7.10 (m,2H), 4.42 (m,
2H), 3.75 (s, 3H), 3.14 (t, 2H), 2.31 (s, 3H)
l-c-22 Cl 6-CI H i-Bu Me 0 0 Et 1H-NMR, 400MHz, CDCI3,
7.40 (d, 2H), 7.29 (t, 1H), 4.13 (q, 2H), 3,84 (s, 3H), 2.51 (d, 2H), 2,10 (m, 1H), 1.15 (t, 3H), 0.96 (d, 6H) l-c-23 F 3-Me 6-F Me Me 0 0 Et 1H-NMR, 400MHz, CDCI3,
7.46 (q 1H), 7.13 (t, 1H), 4.32 (q, 2H), 3,82 (s, 3H), 2,22 (s, 3H), 1.32 (t, 3H)
l-c-24 F 3-OMe 6-F Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.32 (m, 1H), 7.17 (t, 1H), 4.13 (q,2H), 3.85 (s, 3H), 3,71 (s, 3H), 2,25 (s, 3H), 1.09 (t, 3H)
l-c-25 Cl 6-Br 4-Me Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.59 (s, 1H), 7.47 (s, 1H), 4.16 (q,2H), 3,71 (s, 3H), 2,35 (s, 3H), 2,25 (s, 3H), 1.12 (t, 3H)
l-c-26 N02 H H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 8.23 (d, 1H), 7.88 (t, 1H), 7.75 (t, 1H), 7.43 (d, 1H), 4.15 (m, 2H), 3,68 (s, 3H), 2,28 (s, 3H), 0.92 (m, 6H) Nr. X Y Z A B L M R2 Analytische Daten l-c-27 Cl 3-CI H Me Me 0 0 Et 1H-NMR, 400MHz, DMSO,
7.72 (d, 1H), 7.47 (t, 1H), 7.22 (d, 1H),4.13.(q, 2H), 3,72 (s, 3H), 2,25 (s, 3H), 1.07 (t, 3H) l-c-28 Cl 6-F H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.58 (m, 1H), 7.49 (d, 1H), 7.38 (t, 1H) 3,71 (s, 3H), 2,28 (s, 3H), 1.08 (t, 3H) l-c-29 Cl 6-CI H Me Me 0 0 Et 1H-NMR, 400MHz, CDCI3,
7.60 (d, 2H), 7.52 (t, 1H), 4.13 (q, 2H), 3,72 (s, 3H), 2.28 (s, 3H), 1.15 (t, 3H) l-c-30 Cl 4-CI H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.79 (d, 1H), 7.53 (dd, 1H), 7.28 (d, 1H), 4.16 (q, 2H), 3,70 (s, 3H), 2,23 (s, 3H), 1.12 (t, 3H) l-c-31 F 3-F H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.57 (m, 1H), 7.32 (m, 1H), 7.13 (m, 1H), 4.13 (q, 2H), 3,71 (s, 3H), 2,25 (s, 3H), 1.08 (t, 3H) l-c-32 Br 6-Br 4-Me Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.61 (s, 2H), 4.18 (q, 2H), 3,72 (s, 3H), 2.33 (s, 3H), 2,26 (s, 3H), 1.11 (t, 3H) l-c-33 Cl 6-CI 4-OCF3 Me Me 0 0 Et 1H-NMR, 400MHz, CDCI3,
7.82 (s, 2H), 4.17 (q, 2H,) 3,72 (s, 3H)2,28 (s, 3H), 1.07 (t, 3H)
l-c-34 Cl 6-OCF3 4-Me Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.48 (s, 1H), 7.32 (s, 1H), 4.18 (q,2H), 3,71 (s, 3H), 2,42 (s, 3H), 2.21 (s, 3H), 1.12 (t, 3H) l-c-35 OCF3 4-Br 6-Br Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 8.18 (s, 1H), 7.82 (s, 1H), 4.18 (q,2H), 3,72 (s, 3H), 2,26 (s, 3H), 1.13 (t, 3H) l-c-36 H 3-CF3 H Me Me 0 0 Et 1H-NMR, 400MHz, CDCI3,
7.72 (d, 1H), 7.70-7.55 (m, 4H), 4.13 (q, 2H), 3,81 (s, 3H), 2,31 (s, 3H), 1.17 (t, 3H) l-c-37 Cl 3-Me 6-F Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.52 (t, 1H), 7.28 (t, 1H), 4.12 (q,2H), 3,72 (s, 3H), 2,35 (s, 3H), 2,28 (s, 3H), 1.08 (t, 3H) l-c-38 Cl 4-Br 6-CI Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.95 (s, 2H), 4.18 (q, 2H), 3,71 (s, 3H), 2,27 (s, 3H), 1.13 (t, 3H) Nr. X Y Z A B L M R2 Analytische Daten l-c-39 CF3 6-CI H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.97 (d, 1H), 7.89 (d, 1H), 7.73 (t, 1H), 4.16 (q, 2H), 3,73 (s, 3H), 2,28 (s, 3H), 1.12 (t, 3H)
l-c-40 I H H Me Me 0 0 Et 1H-NMR, 400MHz, d6- DMSO, 7.95 (d, 1H), 7.48 (t, 1H), 7.20 (t, 1H), 7.12 (d, 1H), 4.13 (q, 2H), 3,71 (s, 3H), 2,24 (s, 3H), 1.10 (t, 3H) l-c-41 Cl 4-Me 6-Br Me Me 0 0 Me 1H-NMR, 400MHz, d6- DMSO, 7.60 (d, 1H), 7.46 (d, 1H), 3,75 (s, 3H), 3,72 (s, 3H), 2,37 (s, 3H), 2,26 (s, 3H) l-c-42 Cl 3-Me 6-F Me Me 0 0 Me 1H-NMR, 400MHz, d6- DMSO, 7.52 (t, 1H), 7.28 (t, 1H), 3,72 (s, 6H), 2,35 (s, 3H), 2,28 (s, 3H) l-c-43 F 3-F H Me Me 0 0 Bzl 1H-NMR, 400MHz, d6- DMSO, 7.53 (m, 1H), 7.38 (m, 3H), 7.25 (m, 1H), 7.19 (m, 2H), 7.13 (m, 1H), 5.18 (s, 2H), 3,71 (s, 3H), 2,23 (s, 3H) l-c-44 Cl 3-CI H Me Me 0 0 iBu 1H-NMR, 400MHz, DMSO,
7.72 (d, 1H), 7.46 (t, 1H), 7.22 (d, 1H), 3.93.(m, 2H), 3,71 (s, 3H), 2,25 (s, 3H), 1.72 (m, 1H), 0.72 (d, 6H) l-c-45 Cl 4-Me 6-OCF3 Me Me 0 0 All 1H-NMR, 400MHz, d6- DMSO, 7.49 (s, 1H), 7.32 (s, 1H), 5.78 (m, 1H), 5.18 (m, 2H), 4.62 (d,2H), 3,71 (s, 3H), 2,40 (s, 3H), 2.26 (s, 3H) l-c-46 Cl 6-CI H i-Bu Me 0 0 All 1H-NMR, 400MHz, CDCI3,
7.39 (d, 2H), 7.32 (t, 1H), 5.72 (m, 1H), 5.20 (m, 2H), 4.53 (d, 2H), 3,84 (s, 3H), 2,50 (d, 2H), 2.09 (m, 1H), 0.97 (d, 6H)
l-c-47 Me 4-CI 6-Br Me Me 0 0 Et 1H-NMR (400 MHz, DMSO- d6): 7.71 (d, 1H), 7.47 (d, 1H), 4.13 (q,2H), 3.71 (s, 3H), 2.25 (s, 3H), 2.08 (s, 3H), 1.08 (t, 3H) l-c-48 Et 4-Br 6-CI Me Me 0 0 Et 1H-NMR (400 MHz, DMSO- d6): 7.71 (d, 1H), 7.57 (d, 1H), 4.12 (q, 2H), 3.71 (s, 3H), 2.33 (q, 2H), 2.23 (s, 3H), 1.08 (t, 3H), 1.04 (t, 3H) Nr. X Y Z A B L M R2 Analytische Daten l-c-49 Et 4-CI 6-Br Me Me 0 0 Et 1H-NMR (400 MHz, DMSO- d6): 7.72 (d, 1H), 7.48 (d, 1H), 4.12 (q,2H), 3.71 (s, 3H), 2.37 (m, 2H), 2.28 (s, 3H), 1.09 (t, 3H), 1.02 (t, 3H) l-c-50 Et 4-CI 6-I Me Me 0 0 Et 1H-NMR (400 MHz, DMSO- d6): 7.78 (d, 1H), 7.47 (d, 1H), 4.13 (q,2H), 3.73 (s, 3H), 2.35 (m, 2H), 2.25 (s, 3H), 1.12 (t, 3H), 1.04 (t, 3H) l-c-51 Cl 6-CI H c-Pr Me 0 0 Et H-NMR, 400MHz, CDCI3, 7.39
(d, 2H), 7.28 (t, 1H); 4.17 (q, 2H),3.78 (s, 3H); 1.89 (m, 1H), 1.228t, 3H), 1.05 (m, 2H), 0.97 (m, 2H)
l-c-52 Me 3-Br 6-Me H Me 0 0 Et H-NMR (400MHz, CDCI3,
Shiftin ppm): 7.89 (s, 1H), 7.49 (d, 1H), 6.97 (d, 1H), 4.19 (q, 2H), 3,86 (s, 3H), 2,23 (s, 3H), 2.16 (s, 3H), 2.04 (s, 3H), 1.21 (t, 3H) l-c-53 Me 6-Me 3-(4- Me Me 0 0 Et H-NMR (400MHz, CDCI3,
Cl-Ph) Shift in ppm):, 7.86 (s, 1H),
7.37-7.27 (m,6H), 6.97 (d, 1H), 4.16 (q, 2H), 3,86 (s, 3H), 2,23 (s, 3H), 2.12 (s, 3H), 1.96 (s, 3H), 1.20 (t, 3H) l-c-54 Cl 6-Et 4-CI Me Me 0 0 Et H-NMR (400MHz, CDCI3,
Shift in ppm): 7.36 (d, 1H), 7.23 (d, 1H), 4.16 (q, 2H), 3.84 (s, 3H), 2.44 (m, 2H), 2.31 (s, 3 H), 1,21 (t, 3H), 1.15 (t, 3H)
l-c-55 Et 4-Br 6-Et Me Me 0 0 Me
l-c-56 Et 4-cPr 6-Et Me Me 0 0 Me
l-c-57 Me 4-Me 6-Br Me Me 0 0 Me
l-c-58 Cl 3-CI 6-CF3 Me Me 0 0 Et H-NMR (400MHz, CDCI3,
Shift in ppm): 7.67 (d, 1H), 7.63 (d, 1H), 4.21 (q, 2H), 3.83 (s, 3H), 2.33 (s, 3 H), 1,25 (t, 3H)
l-c-59 Et 4-Br 6-Et Me Me 0 0 Et H-NMR (400MHz, CDCI3,
Shift in ppm): 7.28 (d, 1H), 7.25 (d, 1H), 4.12 (q, 2H), 3.82 (s, 3H), 2.36 (q, 2H), 2.30 (s, 3 H), 2.07 (s, 3H), 1,17 (t, 3H), 1.13 (t, 3H) Tabelle 180: Verbindungen der allgemeinen Formel (I), worin G für SO2R3 steht.
Figure imgf000096_0001
Nr. X Y Z R3 A B Analytische Daten
l-d-1 Cl H H Me Me Me 1H-NMR, 400MHz, CDCI3, 7.55 (s, 1H),
7.42 (pseudo t, 3H), 3,81 (s, 3H), 2,51 (s, 3H), 2,48 (s, 3H)
l-d-2 Cl 6-F H Me Me Me 1H-NMR, 400MHz, d6-DMSO, 7.58 (m,
1H), 7.49 (d, 1H), 7.37 (t, 1H) 3,73 (s, 3H), 3.15 (s, 3H), 2.39 (t, 3H) l-d-3 Cl 4-Me 6-Br Me Me Me 1H-NMR, 400MHz, d6-DMSO, 7.61 (s,
1H), 7.48 (s, 1H), 3,71 (s, 3H), 3.11 (s, 3H), 2,38 (s, 3H), 2,33 (s, 3H) l-d-4 N02 H H Me Me Me 1H-NMR, 400MHz, d6-DMSO, 8.23 (d,
1H), 7.88 (t, 1H), 7.77 (t, 1H), 7.60 (d, 1H) 3,67 (s, 3H), 3.05 (s, 3H), 2,39 (s, 3H)
l-d-5 Cl 4-Br 6-CI Me Me Me 1H-NMR, 400MHz, d6-DMSO, 7.96 (s,
2H), 3,71 (s, 3H), 3.35 (s, 3H), 2,40 (s, 3H)
l-d-6 F 3-F H Tolyl Me Me 1H-NMR, 400MHz, d6-DMSO: 7.43 (d,
2H); 7.33 (m, 1H), 7.25 (d, 2H), 7.09 (m, 1H), 7.02 (m, 1H), 3.68 (s, 3H), 2.38 (s, 3H), 2.35 (s, 3H)
l-d-7 Cl 4- 6-CI Et Me Me 1H-NMR, 400MHz, d6-DMSO, 7.82 (s,
OCF3 2H), 3,72 (s, 3H), 3.33 (q, 2H), 2,40 (s,
3H), 1.08 (t, 3H)
l-d-8 F 3- 6-F Me Me Me 1H-NMR, 400MHz, d6-DMSO: 7.33 (m,
OCH3 1H); 7.18 (m, 1H), 3.86 (s, 3H), 3.72 (s,
3H), 3.21 (s, 3H), 2.41 (s, 3H) l-d-9 I H H Me Me 2-(4-CI- H-NMR, 400MHz, CDCI37.92 (d, 1H);
phenyl)- 7.46 (m, 1H); 7.33 (m, 1H), 7.28 (m, ethyl 1H), 7.20 (m, 1H)7.15 (m, 3H), , 4.48
(m, 2H), 3.28 (m, 2H), 2.46 (s, 3H), 2.44 (s, 3H)
l-d-10 Cl 6-CI H Me i- Me 1H-NMR, 400MHz, CDCI3, 7.45 (d, 2H),
Bu 7.32 (t, 3H), 3,85 (s, 3H), 2.71 (d, 2H),
2,61 (s, 3H), 0.99 (d, 6H)
l-d-11 Et 4-CI 6-Br Me Me Me H-NMR (400 MHz, DMSO-d6): 7.73 (d,
1H), 7.50 (d, 1H), 4.13 (q, 2H), 3.71 (s, 3H), 3.07 (s, 3H), 2.40 (m, 2H), 2.38 (s, 3H), 1.09 (t, 3H)
l-d-12 Cl 4-CI 6-Et Me Me Me Tabelle 181: Verbindungen der allgemeinen Formel (I), worin G für E steht.
Figure imgf000097_0001
Nr. X Y Z E A B Analytische Daten
i-g-1 Br 4-Me 6-CI Na+ Me Me H-NMR, 400MHz, d6-DMSO, 7.32 (s,
1H), 7.18 (s, 1H), 3,38 (s, 3H), 2,28 (s, 3H), 1.92 (s, 3H)
i-g-2 N02 H H Na+ Me Me H-NMR, 400MHz, d6-DMSO, 7.78
(d, 1H), 7.65 (t, 1H), 7.43 (t, 1H), 7.20 (d, 1H) 3,18 (s, 3H), 1.93 (s, 3H) i-g-3 N02 H H (Me)4 Me Me H-NMR, 400MHz, d6-DMSO, 7.78
N+ (d, 1H), 7.65 (t, 1H), 7.43 (t, 1H), 7.22
(d, 1H) 3.38 (s, 3H), 3,12 (s, 12H), 1.95 (s, 3H)
i-g-4 Br 6-Me 4-CI Na+ Me Me H-NMR (400 MHz, DMSO-d6): 7.38
(d, 1H), 7.18 (d, 1H), 3.38 (s, 3H), 2.05 (s, 3H), 1.94 (s, 3H) l-g-5 F 3-F H (Me)4 Me Me H-NMR, 400MHz, d6-DMSO, 7.13
N+ (m, 1H), 7.08 (m, 1H), 6.98 (m, 1H),
3,38 (s, 3H), 3.13 (s, 12H), 1.96 (s, 3H)
i-g-6 Me 4-CI 6-CI (Me)4 Me Me H-NMR, 400MHz, d6-DMSO, 7.07
N+ (d, 1H), 6.97 (d, 1H), 3,41 (s, 3H),
2.96 (s, 12H), 1.99 (s, 3H), 1.92 (s, 3H)
Tabelle 182: Verbindungen der allgemeinen Formel (I), worin G für R8 steht.
Figure imgf000098_0001
Nr. X Y Z A B R8 Analytische Daten l-h-1 H 3-CI 4-CI H Me Me Fp.: 176°C
l-h-2 H 3-CF3 5-CF3 H Me Me Fp.: 126-128 °C l-h-3 Me 4-CI H H Me Me Fp.: 142 °C
l-h-4 Cl 4-CI 6-Et Me Me Me H-NMR, 400MHz, CDCI3,
7.52 (s, 1H), 7.35 (d, 1H), 3.73 (s, 3H), 3.47 (s, 3H), 2.45 (m, 2H), 2.30 (s, 3H), 1.15 (m, 3H) l-h-5 Me 6-Me 3-Br H Me Me H-NMR, 400MHz, d6- DMSO, 8.26 (s, 1H), 7.49 (d, 1H), 7.05 (d, 1H), 3.90 (s, 3H), 3.70 (s, 3H), 2.04 (s, 3H), 1.93 (s, 3H) l-h-6 Me 6-Me 3-(4-CI- H Me Me H-NMR, 400MHz, CDCI3,
Ph) 7.89 (s, 1H), 7.49 (d, 1H),
7.05 (d, 1H), 3.85 (pseudo d, 6H), 3.70 (s, 3H), 2.00 (s, 3H), 1.95 (s, 3H) l-h-7 Me 6-CI 4-CI Me Me Propinyl H-NMR, 400MHz, d6- DMSO, 7.59 (s, 1H), 7.42 (d, 1H), 4.32 (pseudo q, 2H), 3.62 (s, 3H), 2.52 (s, 1H), 2.28 (s, 3H), 2.13 (s, 3H)
l-h-8 Et 6-CI 4-CI Me Me Propinyl H-NMR, 400MHz, CDCI3,
7.38 (s, 1H), 7.25 (d, 1H), 4.22 (pseudo q, 2H), 3.75 (s, 3H), 2.50 (s, 1H), 2.45 (m, 2H), 2.35 (s, 3H), 1.14 (m, 3H)
l-h-9 N02 H H Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 8.18 (d, 1H), 7.84 (t, 1H), 7.72 (t, 1H), 7.54 (d, 1H)4.38 (m, 2H), 3,60 (s, 3H), 3.56 (m, 1H), 2,32 (s, 3H)
l-h-10 Me 4-CI 6-Br Me Me Propinyl H-NMR(400 MHz,
DMSO-de): 7.71 (d, 1H), 7.49 (d, 1H), 4.32 (m, 2H), 3.65 (s, 3H), 3.63 (m, 1H), 2.29 (s, 3H), 2.14 (s, 3H) Nr. X Y Z A B R8 Analytische Daten l-h-11 F 3-F H Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.53 (m, 1H), 7.30 (m, 1H), 7.19 (m, 1H), 4.40 (m, 2H), 3,64 (s, 3H), 3.57 (m, 1H), 2,29 (s, 3H) l-h-12 Cl 4-Me 6-Br Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.60 (d, 1H), 7.47 (d, 1H), 4.37 (m, 2H), 3,63 (s, 3H), 3.62 (m, 1H), 2.36 (s, 3H), 2,29 (s, 3H) l-h-13 Cl 4-Me 6-OCF3 Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.49 (d, 1H), 7.32 (d, 1H), 4.38 (m, 2H), 3,63 (s, 3H), 3.59 (m, 1H), 2.42 (s, 3H), 2,28 (s, 3H) l-h-14 Et 4-Br Et Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.38 (s, 2H), 4.22 (m, 2H), 3,63 (m, 4H), 2.34 (m, 4H), 2,28 (s, 6H) l-h-15 Cl 6-F H Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.56 (m, 1H), 7.47 (d, 1H), 7.34 (m, 1H), 4.42 (m, 2H), 3,64 (s, 3H), 3.60 (m, 1H), 2,29 (s, 3H) l-h-16 Cl 4-CI 6-Et Et Me Propinyl H-NMR, 400MHz, DMSO,
7.61 (d, 1H), 7.43 (d, 1H), 4.29 (pseudo q, 2H), 3.64 (s, 3H), 3.62 (s, 1H), 2.70 (q, 2H), 2.68 (q, 2H), 2.40 (m, 2H), 1.19 (t, 3H), 1.06 (t, 3H)
l-h-17 F 3-Me 6-F Me Me Propinyl 1H-NMR, 400MHz, d6- DMSO, 7.43 (q, 1H), 7.12 (t, 1H), 7.34 (m, 1H), 4.46 (s, 2H), 3,63 (s, 3H), 3.58 (m, 1H), 2,30 (s, 3H), 2.26 (s, 3H)
l-h-18 Cl Cl Et Me Et Propinyl H-NMR, 400MHz, DMSO,
7.60 (d, 1H), 7.43 (d, 1H), 4.37 (m, 2H), 4.06 (m, 2H), 3.62 (s, 1H), 2.40 (m, 2H), 2.30 (s, 3H), 1.22 (t, 3H), 1.08 (t, 3H) l-h-19 Cl Cl 6-Et i-Bu Me Propinyl H-NMR, 400MHz, CDCI3,
7.38 (s, 1H), 7.25 (d, 1H), 4.18 (pseudo q, 2H), 3.75 (s, 3H), 2.60 (m, 2H), 2.48 (m, 1H), 2.45 (m, 2H), 2.10 (m, 1H), 1.17 (m, 3H), 0.99 (d, 6H) l-h-20 Cl Cl 6-Et i-Bu Me Allyl H-NMR, 400MHz, CDCI3,
7.38 (s, 1H), 7.24 (d, 1H), 5.72 (m, 1H), 5.18 (m, 1H), 4.02 (m, 1H), 3.75 (s, 3H), 2.53 (m, 1H), 1.12 (m, 3H), 0.95 (d, 6H) Nr. X Y z A B R8 Analytische Daten l-h-21 Cl Cl 6-Et c- Me Propinyl H-NMR, 400MHz, CDCI3,
Pentyl 7.38 (s, 1 H), 7.25 (d, 1 H),
4.18 (m, 2H), 3.72 (s, 3H), 3.33 (m, 1 H), 2.48 (m, 1 H), 2.45 (m, 2H), 2.00(m, 2H), 1.75 (Signalhaufen, 6H), 1.14 (m, 3H) l-h-22 I H H Me 2-(2-CI-Phenyl) Propinyl H-NMR, 400MHz, CDCI3, ethyl 7.92 (d, 2H), 7.43 (t, 1 H),
7.33 (m, 1 H), 7.27 (m, 4 H), 7.12 (m, 3H), 4.40 (m, 2H), 4.18 (m, 2H), 3.26 (m, 2H), 2.31 (s, 3H), l-h-23 Cl 4-CI 6-Et i-Bu Me Butinyl H-NMR, 400MHz, CDCI3,
7.36 (s, 1 H), 7.22 (d, 1 H), 4.18 (pseudo q, 2H), 3.78 (s, 3H), 2.58 (d, 2H), 2.45 (m, 2H), 2.12 (m, 1 H), 1.79 (s, 3H), 1.16 (m, 3H), 0.97 (d, 6H)
l-h-24 Cl 6-CI H -Bu Me Me H-NMR, 400MHz, CDCI3,
7.42 (d, 2H), 7.29 (t, 1 H), 3.75 (s, 3H), 3.48 (s, 3H), 2.53 (d, 2H), 2.06 (m, 1 H), 0.97 (d, 6H)
Die Aufwandmenge der Herbizide der allgemeinen Formel (I) kann mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids in einem weiten Bereich variieren, beispielsweise zwischen 0,001 g und 1000 g a.i./ha (ai/ha bedeutet dabei im folgenden„Aktivsubstanz pro Hektar" = bezogen auf
100%igen Wirkstoff).
Bei Anwendungen mit Aufwandmengen von 0,01 g bis 800 g a.i./ha der Herbizide der allgemeinen Formel (I) (A) wird im Vor- und Nachauflaufverfahren ein relativ brei- tes Spektrum an Schadpflanzen bekämpft, z.B. annuellen und perennierenden mono- oder dikotylen Unkräutern sowie an unerwünschten Kulturpflanzen. Bei den erfindungsgemäßen Kombinationen liegen die Aufwandmengen in der Regel niedriger, z. B. im Bereich von 0,1 g bis 500 g a.i./ha, vorzugsweise 10 g bis 400 g a.i./ha, besonders bevorzugt 20 g bis 300 g a.i./ha.
Die Herbizide der allgemeinen Formel (I) sind zur Bekämpfung von Schadpflanzen, z.B. in Pflanzenkulturen geeignet, beispielsweise in wirtschaftlich bedeutenden Ackerbaukulturen z.B. monokotylen Ackerbaukulturen wie Getreide (z.B. Weizen, Gerste, Roggen, Hafer), Reis, Mais, Hirse, oder dikotylen Ackerbaukulturen wie Zuckerrübe, Raps, Baumwolle, Sonnenblume und Leguminosen z.B. der Gattungen Glycine (z.B. Glycine max. (Soja) wie nicht-transgene Glycine max. (z.B. konventionelle Sorten wie STS-Sorten) oder transgene Glycine max. (z.B. RR-Soja oder LL- Soja) und deren Kreuzungen), Phaseolus, Pisum, Vicia und Arachis, oder Gemüsekulturen aus verschiedenen botanischen Gruppen wie Kartoffel, Lauch, Kohl, Karotte, Tomate, Zwiebel, sowie Dauer- und Plantagenkulturen wie Kern- und Steinobst, Beerenobst, Wein, Hevea, Bananen, Zuckerrohr, Kaffee, Tee, Citrus, Nussplanta- gen, Rasen, Palmenkulturen und Forstkulturen. Für die Anwendung der erfindungs- gemäßen Herbizid-Safener-Kombinationen (A)+(B) sind diese Kulturen ebenfalls bevorzugt, besonders bevorzugt ist der Einsatz in Getreide (z.B. Weizen, Gerste, Roggen, Hafer), Reis, Mais, Hirse, Zuckerrübe, Zuckerrohr, Sonnenblume, Raps und Baumwolle. Die Herbizid-Safener-Kombinationen (A)+(B) sind auch einsetzbar in toleranten und nicht toleranten Mutantenkulturen und toleranten und nicht toleranten transgenen Kulturen, vorzugsweise von Mais, Reis, Getreide, Raps und Soja, z.B. solche die gegen Imidazolinon-Herbizide, Atrazin, Glufosinate oder Glyphosate resistent sind.
Die Verbindungen der allgemeinen Formel (I) sind aus WO 2005/063721 A und WO 2007/082076 A bekannt und können nach den dort beschriebenen Verfahren erhalten werden.
Safener (B):
Unter den als Komponente (B) enthaltenen Safenern werden Verbindungen verstan- den, die geeignet sind, phytotoxische Wirkungen von Pflanzenschutzmittelwirkstoffen wie Herbiziden an Kulturpflanzen zu reduzieren.
Im Rahmen der vorliegenden Erfindung werden die Verbindungen der allgemeinen Formel (I) mit folgenden Safener-Verbindungen kombiniert:
S1 ) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate: Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (S1 a), vorzugsweise Verbindungen wie
1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure, 1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure- ethylester (S1 -1 ) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind;
Derivate der Dichlorphenylpyrazolcarbonsäure (S1 b), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methylpyrazol-3-carbonsäureethylester (S1 -2), 1 -(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (S1 -3), 1 -(2,4-Dichlorphenyl)-5-(1 ,1 -dimethyl-ethyl)pyrazol-3-carbonsäure- ethylester (S1 -4) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind;
Derivate der 1 ,5-Diphenylpyrazol-3-carbonsäure (S1 c), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S1 -5), 1 -(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (S1 -6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind;
Verbindungen vom Typ der Triazolcarbonsäuren (S1 d), vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d.h. 1 -(2,4-Dichlor- phenyl)-5-trichlormethyl-(1 H)-1 ,2,4-triazol-3-carbonsäureethylester (S1 -7), und verwandte Verbindungen, wie sie in EP-A-174 562 und EP-A-346 620 beschrieben sind;
Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure(S1 e), vorzugsweise Verbindungen wie 5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (S1 -8) oder 5-Phenyl-2-isoxazolin-3-carbonsäureethylester (S1 -9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-carbonsäure (S1 -10) oder 5,5-Diphenyl-2- isoxazolin-3-carbonsäureethylester (S1 -1 1 ) ("Isoxadifen-ethyl") oder
-n-propylester (S1 -12) oder der 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3- carbonsäureethylester (S1 -13), wie sie in der Patentanmeldung
WO-A-95/07897 beschrieben sind.
Verbindungen aus der Gruppe der 8-Chinolinyloxyderivate (S2):
Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise (5-Chlor-8-chinolinoxy)essigsäure-(1 -methylhexyl)-ester ("Cloquintocet- mexyl") (S2-1 ), (5-Chlor-8-chinolinoxy)essigsäure-(1 ,3-dimethyl-but-1 -yl)-ester (S2-2), (5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (S2-3), (5-Chlor-8-chinolinoxy)essigsäure-1 -allyloxy-prop-2-ylester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6),
(5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-1 -ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-1 -ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86 750, EP-A-94 349 und
EP-A-191 736 oder EP-A-0 492 366 beschrieben sind, sowie (5-Chlor-8- chinolinoxy)essigsäure (S2-10), deren Hydrate und Salze, beispielsweise deren Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze wie sie in der WO-A-2002/34048 beschrieben sind;
Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor-8-chinolinoxy)malonsäurediallylester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.
Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflauf- safener (bodenwirksame Safener) angewendet werden, wie z. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1 ), "R-29148" (3-Dichloracetyl-2,2,5-trimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-2),
"R-28725" (3-Dichloracetyl-2,2,-dimethyl-1 ,3-oxazolidin) der Firma Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-1 ,4-benzoxazin) (S3-4),
"PPG-1292" (N-Allyl-N-[(1 ,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-1 -oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7),
"TI-35" (1 -Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9)
((RS)-1 -Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[1 ,2-a]pyrimidin-6-on) der Firma BASF,
"Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyl- oxazolidin) (S3-10), sowie dessen (R)-Isomer (S3-1 1 ). S4) Verbindungen aus der Klasse der Acylsulfonamide (S4):
S4a) N-Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der
-A-97/45016 beschrieben sind,
Figure imgf000104_0001
RA1 (CrC6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vA Substituenten aus der Gruppe Halogen, (d-C4)Alkoxy, (Ci-Ce)Halo- alkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch durch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert sind;
RA 2 Halogen, (d-C4)Alkyl, (d-C4)Alkoxy, CF3;
mA 1 oder 2; vA ist 0, 1 , 2 oder 3 bedeuten;
Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, wie sie in der WO-A-99/16744 beschrieben sind,
Figure imgf000105_0001
worin
RB1 , RB2 unabhängig voneinander Wasserstoff, (d-C6)Alkyl,
(C3-C6)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl,
RB 3 Halogen, (d-C4)Alkyl, (d-C4)Haloalkyl oder (d-C4)Alkoxy und
ITIES 1 oder 2 bedeuten, z.B. solche worin
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist (S4-1 , "Cyprosul- famide",),
RB 1 = Cyclopropyl, RB 2 = Wasserstoff und (RB3) = 5-CI-2-OMe ist (S4-2),
RB 1 = Ethyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist (S4-3),
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB3) = 5-CI-2-OMe ist (S4-4) und
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB3) = 2-OMe ist (S4-5). S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylharnstoffe der ForC), wie sie in der EP-A-365484 beschrieben sind
Figure imgf000105_0002
worin
Rc1, Rc2 unabhängig voneinander Wasserstoff, (Ci-Cs)Alkyl,
(C3-C8)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl,
Rc3 Halogen, (d-C4)Alkyl, (d-C4)Alkoxy, CF3 nric 1 oder 2 bedeuten; beispielsweise
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylharnstoff,
1 -[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylharnstoff,
1 -[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylharnstoff.
S5) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch- aliphatischen Carbonsäurederivate (S5), z.B.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoe- säure, 3,5-Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicycl- säure, 2-Hydroxyzimtsäure, 2,4-Dichlorzimtsäure, wie sie in der WO-A- 2004/084631 , WO-A-2005/015994, WO-A-2005/016001 beschrieben sind.
S6) Wirkstoffe aus der Klasse der 1 ,2-Dihydrochinoxalin-2-one (S6), z.B.
1 -Methyl-3-(2-thienyl)-1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3-(2-thienyl)-1 ,2- dihydrochinoxalin-2-thion, 1 -(2-Aminoethyl)-3-(2-thienyl)-1 ,2-dihydro- chinoxalin-2-on-hydrochlorid, 1 -(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-1 ,2- dihydro-chinoxalin-2-οη, wie sie in der WO-A-2005/1 12630 beschrieben sind.
S7) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurede vate (S7), z.B. Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1 ), Diphenylmethoxyessigsäureethylester oder Diphenylmethoxy- essigsäure wie sie in der WO-A-98/38856 beschrieben sind.
S8) Verbindungen der Formel (S8),wie sie in der WO-A-98/27049 beschrieben sind
worin die Symbole und Indizes folgende Bedeutungen haben: RD 1 ist Halogen, (Ci-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, RD 2 ist Wasserstoff oder (d-C4)Alkyl
RD 3 ist Wasserstoff, (Ci-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der
Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze nD ist eine ganze Zahl von 0 bis 2.
Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), 1 ,2-Dihydro-4-hydroxy-1 -ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS- Reg.Nr.: 219479-18-2), 1 ,2-Dihydro-4-hydroxy-1 -methyl-3-(5-tetrazolyl- carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der
WO-A- 1999/000020 beschrieben sind. S10) Verbindungen der Formeln (S10a) oder (S10b)
wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind
Figure imgf000107_0001
(S10a) (S10b)
worin
RE 1 Halogen, (d-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3
YE, Ze unabhängig voneinander O oder S,
nE eine ganze Zahl von 0 bis 4,
RE 2 (Ci-Ci6)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RE 3 Wasserstoff oder (Ci-C6)Alkyl bedeuten.
S1 1 ) Wirkstoffe vom Typ der Oxyimino-Verbindungen (S1 1 ), die als Saatbeizmittel bekannt sind, wie z. B.
Oxabetrinil" ((Z)-1 ,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (S1 1 -1 ), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist,
"Fluxofenim" (1 -(4-Chlorphenyl)-2,2,2-thfluor-1 -ethanon-O-(1 ,3-dioxolan-2- ylmethyl)-oxinn) (S1 1 -2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und
"Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (S1 1 -3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. S12) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl-[(3- oxo-1 H-2-benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121 - 04-6) (S12-1 ) und verwandte Verbindungen aus WO-A-1998/13361 .
S13) Eine oder mehrere Verbindungen aus Gruppe (S13):
"Naphthalic anhydrid" (1 ,8-Naphthalindicarbonsäureanhydrid) (S13-1 ), das als
Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist,
"Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als Safener für Preti- lachlor in gesätem Reis bekannt ist,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-1 ,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist,
"CL 304415" (CAS-Reg.Nr. 31541 -57-8)
(4-Carboxy-3,4-dihydro-2H-1 -benzopyran-4-essigsäure) (S13-4) der Firma American Cyanamid, das als Safener für Mais gegen Schäden von Imidazoli- nonen bekannt ist,
"MG 191 " (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-1 ,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist,
"MG-838" (CAS-Reg.Nr. 133993-74-5)
(2-propenyl 1 -oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma
Nitrokemia
"Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8),
"Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9).
514) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B.
"Dimepiperate" oder "MY-93" (S-1 -Methyl-1 -phenylethyl-piperidin-1 - carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist,
"Daimuron" oder "SK 23" (1 -(1 -Methyl-1 -phenylethyl)-3-p-tolyl-harnstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist (S14-1 ),
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-1 -(1 -methyl-1 -phenyl- ethyl)harnstoff, siehe JP-A-60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist,
"Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "CSB" (1 -Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091 -06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist.
515) Verbindungen der Formel (S15) oder deren Tautomere
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind
Figure imgf000109_0001
worin
RH1 einen (d-C6)Haloalkylrest bedeutet und
RH2 Wasserstoff oder Halogen bedeutet und
RH3, RH4 unabhängig voneinander Wasserstoff, (d-Ci6)Alkyl, (C2-Ci6)Alkenyl oder (C2-Ci6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, [(d-C4)Alkoxy]-carbonyl, [(d-C4)Haloalkoxy]- carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist,
oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist,
wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (CrC4)Alkylamino, Di[(CrC4)alkyl]-amino, [(Ci -C4)AI koxyj-carbonyl , [(Ci -C4)Haloal koxyj-carbonyl , (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist,
bedeutet oder
RH3 (d-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und
RH4 Wasserstoff oder (d-C4)-Alkyl bedeutet oder
RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis acht- gliedrigen heterocydischen Ring, der neben dem N-Atom auch weitere Hete- roringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet. S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z.B.
(2,4-Dichlorphenoxy)essigsäure (2,4-D),
(4-Chlorphenoxy)essigsäure,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure,
4-(4-Chlorphenoxy)buttersäure,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),
1-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl).
Die zitierten Schriften enthalten ausführliche Angaben zu Herstellungsverfahren und Ausgangsmaterialien und nennen bevorzugte Verbindungen. Auf diese Schriften wird ausdrücklich Bezug genommen, sie gelten durch Zitat als Bestandteil dieser Beschreibung. Einige der zuvor genannten Safener sind bereits als Herbizide bekannt und entfalten somit neben der Herbizidwirkung bei Schadpflanzen zugleich auch eine Schutzwirkung bei Kulturpflanzen. Diese Verbindungen können daher sowohl als Safener als auch als herbizider Mischungspartner verwendet werden. Beispiele für bevorzugte Kombinationen von herbiziden Wirkstoffen (A) und Safenern (B) sind in der folgenden Tabelle dargestellt:
(l-a-1) + (S1-1); (l-a-1) + (S1-2); (l-a-1) + (S1-3); (l-a-1) + (S1-4); (l-a-1) + (S1-5); (l-a-1) + (S1-6); (l-a-1) + (S1-7); (l-a-1) + (S1-8); (l-a-1) + (S1-9); (l-a-1) + (S1-10); (l-a-1) + (S1-11); (l-a-1) + (S1- 12); (l-a-1) + (S1-13); (l-a-1) + (S2-1); (l-a-1) + (S2-2); (l-a-1) + (S2-3); (l-a-1) + (S2-4); (l-a-1) + (S2-5); (l-a-1) + (S2-6); (l-a-1) + (S2-7); (l-a-1) + (S2-8); (l-a-1) + (S2-9); (l-a-1) + (S2-10); (l-a-1) + (S3-1); (l-a-1) + (S3-2); (l-a-1) + (S3-3); (l-a-1) + (S3-4); (l-a-1) + (S3-5); (l-a-1) + (S3-6); (l-a-1) + (S3-7); (l-a-1 ) + (S3-8); (l-a-1 ) + (S3-9); (l-a-1 ) + (S3-10); (l-a-1 ) + (S3-11 ); (l-a-1 ) + (S4-1 ); (l-a-1 ) + (S4-2); (l-a-1) + (S4-3); (l-a-1) + (S4-4); (l-a-1) + (S4-5); (l-a-1) + (S7-1); (l-a-1) + (S11-1); (l-a-1) + (S1 1-2); (l-a-1 ) + (S1 1-3); (l-a-1 ) + (S12-1 ); (l-a-1 ) + (S13-1 ); (l-a-1 ) + (S13-2); (l-a-1 ) + (S13-3); (l-a-1 ) + (S13-4): (l-a-1 ) + (S13-5); (l-a-1 ) + (S13-6); (l-a-1 ) + (S13-7); (l-a-1 ) + (S13-8); (l-a-1 ) + (S13-9); (l-a-1 ) + (S14-1 )
(l-a-2) + (S1-1 ); (l-a-2) + (S1-2); (l-a-2) + (S1-3); (l-a-2) + (S1-4); (l-a-2) + (S1-5); (l-a-2) + (S1-6); (l-a-2) + (S1-7); (l-a-2) + (S1-8); (l-a-2) + (S1-9); (l-a-2) + (S1-10); (l-a-2) + (S1-1 1 ); (l-a-2) + (S1- 12); (l-a-2) + (S1-13); (l-a-2) + (S2-1 ); (l-a-2) + (S2-2); (l-a-2) + (S2-3); (l-a-2) + (S2-4); (l-a-2) + (S2-5); (l-a-2) + (S2-6); (l-a-2) + (S2-7); (l-a-2) + (S2-8); (l-a-2) + (S2-9); (l-a-2) + (S2-10); (l-a-2) + (S3-1 ); (l-a-2) + (S3-2); (l-a-2) + (S3-3); (l-a-2) + (S3-4); (l-a-2) + (S3-5); (l-a-2) + (S3-6); (l-a-2) + (S3-7); (l-a-2) + (S3-8); (l-a-2) + (S3-9); (l-a-2) + (S3-10); (l-a-2) + (S3-1 1 ); (l-a-2) + (S4-1 ); (l-a-2) + (S4-2); (l-a-2) + (S4-3); (l-a-2) + (S4-4); (l-a-2) + (S4-5); (l-a-2) + (S7-1 ); (l-a-2) + (S1 1-1 ); (l-a-2) + (S1 1-2); (l-a-2) + (S1 1-3); (l-a-2) + (S12-1 ); (l-a-2) + (S13-1 ); (l-a-2) + (S 13-2); (l-a-2) + (S 13-3); (l-a-2) + (S13-4): (l-a-2) + (S13-5); (l-a-2) + (S13-6); (l-a-2) + (S13-7); (l-a-2) + (S13-8); (l-a-2) + (S13-9); (l-a-2) + (S 14-1 )
(l-a-3) + (S1-1 ); (l-a-3) + (S1-2); (l-a-3) + (S1-3); (l-a-3) + (S1-4); (l-a-3) + (S1-5); (l-a-3) + (S1-6); (l-a-3) + (S1-7); (l-a-3) + (S1-8); (l-a-3) + (S1-9); (l-a-3) + (S1-10); (l-a-3) + (S1-1 1 ); (l-a-3) + (S1- 12); (l-a-3) + (S1-13); (l-a-3) + (S2-1 ); (l-a-3) + (S2-2); (l-a-3) + (S2-3); (l-a-3) + (S2-4); (l-a-3) + (S2-5); (l-a-3) + (S2-6); (l-a-3) + (S2-7); (l-a-3) + (S2-8); (l-a-3) + (S2-9); (l-a-3) + (S2-10); (l-a-3) + (S3-1 ); (l-a-3) + (S3-2); (l-a-3) + (S3-3); (l-a-3) + (S3-4); (l-a-3) + (S3-5); (l-a-3) + (S3-6); (l-a-3) + (S3-7); (l-a-3) + (S3-8); (l-a-3) + (S3-9); (l-a-3) + (S3-10); (l-a-3) + (S3-1 1 ); (l-a-3) + (S4-1 ); (l-a-3) + (S4-2); (l-a-3) + (S4-3); (l-a-3) + (S4-4); (l-a-3) + (S4-5); (l-a-3) + (S7-1 ); (l-a-3) + (S1 1-1 ); (l-a-3) + (S1 1-2); (l-a-3) + (S1 1-3); (l-a-3) + (S12-1 ); (l-a-3) + (S13-1 ); (l-a-3) + (S13-2); (l-a-3) + (S 13-3); (l-a-3) + (S13-4): (l-a-3) + (S13-5); (l-a-3) + (S13-6); (l-a-3) + (S13-7); (l-a-3) + (S13-8); (l-a-3) + (S13-9); (l-a-3) + (S 14-1 )
(l-a-4) + (S1-1 ); (l-a-4) + (S1-2); (l-a-4) + (S1-3); (l-a-4) + (S1-4); (l-a-4) + (S1-5); (l-a-4) + (S1-6); (l-a-4) + (S1-7); (l-a-4) + (S1-8); (l-a-4) + (S1-9); (l-a-4) + (S1-10); (l-a-4) + (S1-1 1 ); (l-a-4) + (S1- 12); (l-a-4) + (S1-13); (l-a-4) + (S2-1 ); (l-a-4) + (S2-2); (l-a-4) + (S2-3); (l-a-4) + (S2-4); (l-a-4) + (S2-5); (l-a-4) + (S2-6); (l-a-4) + (S2-7); (l-a-4) + (S2-8); (l-a-4) + (S2-9); (l-a-4) + (S2-10); (l-a-4) + (S3-1 ); (l-a-4) + (S3-2); (l-a-4) + (S3-3); (l-a-4) + (S3-4); (l-a-4) + (S3-5); (l-a-4) + (S3-6); (l-a-4) + (S3-7); (l-a-4) + (S3-8); (l-a-4) + (S3-9); (l-a-4) + (S3-10); (l-a-4) + (S3-1 1 ); (l-a-4) + (S4-1 ); (l-a-4) + (S4-2); (l-a-4) + (S4-3); (l-a-4) + (S4-4); (l-a-4) + (S4-5); (l-a-4) + (S7-1 ); (l-a-4) + (S1 1-1 ); (l-a-4) + (S1 1-2); (l-a-4) + (S1 1-3); (l-a-4) + (S12-1 ); (l-a-4) + (S13-1 ); (l-a-4) + (S 13-2); (l-a-4) + (S 13-3); (l-a-4) + (S13-4): (l-a-4) + (S13-5); (l-a-4) + (S13-6); (l-a-4) + (S13-7); (l-a-4) + (S13-8); (l-a-4) + (S13-9); (l-a-4) + (S 14-1 )
(l-a-5) + (S1-1 ); (l-a-5) + (S1-2); (l-a-5) + (S1-3); (l-a-5) + (S1-4); (l-a-5) + (S1-5); (l-a-5) + (S1-6); (l-a-5) + (S1-7); (l-a-5) + (S1-8); (l-a-5) + (S1-9); (l-a-5) + (S1-10); (l-a-5) + (S1-1 1 ); (l-a-5) + (S1- 12); (l-a-5) + (S1-13); (l-a-5) + (S2-1 ); (l-a-5) + (S2-2); (l-a-5) + (S2-3); (l-a-5) + (S2-4); (l-a-5) + (S2-5); (l-a-5) + (S2-6); (l-a-5) + (S2-7); (l-a-5) + (S2-8); (l-a-5) + (S2-9); (l-a-5) + (S2-10); (l-a-5) + (S3-1 ); (l-a-5) + (S3-2); (l-a-5) + (S3-3); (l-a-5) + (S3-4); (l-a-5) + (S3-5); (l-a-5) + (S3-6); (l-a-5) + (S3-7); (l-a-5) + (S3-8); (l-a-5) + (S3-9); (l-a-5) + (S3-10); (l-a-5) + (S3-1 1 ); (l-a-5) + (S4-1 ); (l-a-5) + (S4-2); (l-a-5) + (S4-3); (l-a-5) + (S4-4); (l-a-5) + (S4-5); (l-a-5) + (S7-1 ); (l-a-5) + (S1 1-1 ); (l-a-5) + (S1 1-2); (l-a-5) + (S1 1-3); (l-a-5) + (S12-1 ); (l-a-5) + (S13-1 ); (l-a-5) + (S 13-2); (l-a-5) + (S 13-3); (l-a-5) + (S13-4): (l-a-5) + (S13-5); (l-a-5) + (S13-6); (l-a-5) + (S13-7); (l-a-5) + (S13-8); (l-a-5) + (S13-9); (l-a-5) + (S 14-1 )
(l-a-6) + (S1-1 ); (l-a-6) + (S1-2); (l-a-6) + (S1-3); (l-a-6) + (S1-4); (l-a-6) + (S1-5); (l-a-6) + (S1-6); (l-a-6) + (S1-7); (l-a-6) + (S1-8); (l-a-6) + (S1-9); (l-a-6) + (S1-10); (l-a-6) + (S1-1 1 ); (l-a-6) + (S1- 12); (l-a-6) + (S1-13); (l-a-6) + (S2-1 ); (l-a-6) + (S2-2); (l-a-6) + (S2-3); (l-a-6) + (S2-4); (l-a-6) + (S2-5); (l-a-6) + (S2-6); (l-a-6) + (S2-7); (l-a-6) + (S2-8); (l-a-6) + (S2-9); (l-a-6) + (S2-10); (l-a-6) + (S3-1 ); (l-a-6) + (S3-2); (l-a-6) + (S3-3); (l-a-6) + (S3-4); (l-a-6) + (S3-5); (l-a-6) + (S3-6); (l-a-6) + (S3-7); (l-a-6) + (S3-8); (l-a-6) + (S3-9); (l-a-6) + (S3-10); (l-a-6) + (S3-1 1 ); (l-a-6) + (S4-1 ); (l-a-6) + (S4-2); (l-a-6) + (S4-3); (l-a-6) + (S4-4); (l-a-6) + (S4-5); (l-a-6) + (S7-1 ); (l-a-6) + (S1 1-1 ); (l-a-6) + (S1 1-2); (l-a-6) + (S1 1-3); (l-a-6) + (S12-1 ); (l-a-6) + (S13-1 ); (l-a-6) + (S 13-2); (l-a-6) + (S 13-3); (l-a-6) + (S13-4): (l-a-6) + (S13-5); (l-a-6) + (S13-6); (l-a-6) + (S13-7); (l-a-6) + (S13-8); (l-a-6) + (S13-9); (l-a-6) + (S 14-1 )
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(l-h-19) + (S1-1 ); (l-h-19) + (S1-2); (l-h-19) + (S1-3); (l-h-19) + (S1-4); (l-h-19) + (S1-5); (l-h-19) + (S1-6); (l-h-19) + (S1-7); (l-h-19) + (S1-8); (l-h-19) + (S1-9); (l-h-19) + (S1-10); (l-h-19) + (S1-1 1 ); (l-h-19) + (S1-12); (l-h-19) + (S1-13); (l-h-19) + (S2-1 ); (l-h-19) + (S2-2); (l-h-19) + (S2-3); (l-h-19) + (S2-4); (l-h-19) + (S2-5); (l-h-19) + (S2-6); (l-h-19) + (S2-7); (l-h-19) + (S2-8); (l-h-19) + (S2-9); (I- h-19) + (S2-10); (l-h-19) + (S3-1 ); (l-h-19) + (S3-2); (l-h-19) + (S3-3); (l-h-19) + (S3-4); (l-h-19) + (S3-5); (l-h-19) + (S3-6); (l-h-19) + (S3-7); (l-h-19) + (S3-8); (l-h-19) + (S3-9); (l-h-19) + (S3-10); (I- h-19) + (S3-1 1 ); (l-h-19) + (S4-1 ); (l-h-19) + (S4-2); (l-h-19) + (S4-3); (l-h-19) + (S4-4); (l-h-19) + (S4-5); (l-h-19) + (S7-1 ); (l-h-19) + (S1 1-1 ); (l-h-19) + (S1 1-2); (l-h-19) + (S1 1-3); (l-h-19) + (S12- 1 ); (l-h-19) + (S13-1 ); (l-h-19) + (S13-2); (l-h-19) + (S13-3); (l-h-19) + (S13-4): (l-h-19) + (S13-5); (I- h-19) + (S13-6); (l-h-19) + (S13-7); (l-h-19) + (S13-8); (l-h-19) + (S13-9); (l-h-19) + (S14-1 )
(l-h-20) + (S1-1 ); (l-h-20) + (S1-2); (l-h-20) + (S1-3); (l-h-20) + (S1-4); (l-h-20) + (S1-5); (l-h-20) + (S1-6); (l-h-20) + (S1-7); (l-h-20) + (S1-8); (l-h-20) + (S1-9); (l-h-20) + (S1-10); (l-h-20) + (S1-1 1 ); (l-h-20) + (S1-12); (l-h-20) + (S1-13); (l-h-20) + (S2-1 ); (l-h-20) + (S2-2); (l-h-20) + (S2-3); (l-h-20) + (S2-4); (l-h-20) + (S2-5); (l-h-20) + (S2-6); (l-h-20) + (S2-7); (l-h-20) + (S2-8); (l-h-20) + (S2-9); (I- h-20) + (S2-10); (l-h-20) + (S3-1 ); (l-h-20) + (S3-2); (l-h-20) + (S3-3); (l-h-20) + (S3-4); (l-h-20) + (S3-5); (l-h-20) + (S3-6); (l-h-20) + (S3-7); (l-h-20) + (S3-8); (l-h-20) + (S3-9); (l-h-20) + (S3-10); (I- h-20) + (S3-11); (l-h-20) + (S4-1); (l-h-20) + (S4-2); (l-h-20) + (S4-3); (l-h-20) + (S4-4); (l-h-20) + (S4-5); (l-h-20) + (S7-1); (l-h-20) + (S11-1); (l-h-20) + (S11-2); (l-h-20) + (S11-3); (l-h-20) + (S12- 1); (l-h-20) + (S13-1); (l-h-20) + (S13-2); (l-h-20) + (S13-3); (l-h-20) + (S13-4): (l-h-20) + (S13-5); (I- h-20) + (S13-6); (l-h-20) + (S13-7); (l-h-20) + (S13-8); (l-h-20) + (S13-9); (l-h-20) + (S14-1)
(l-h-21) + (S1-1); (l-h-21) + (S1-2); (l-h-21) + (S1-3); (l-h-21) + (S1-4); (l-h-21) + (S1-5); (l-h-21) + (S1-6); (l-h-21) + (S1-7); (l-h-21) + (S1-8); (l-h-21) + (S1-9); (l-h-21) + (S1-10); (l-h-21) + (S1-11); (l-h-21) + (S1-12); (l-h-21) + (S1-13); (l-h-21) + (S2-1); (l-h-21) + (S2-2); (l-h-21) + (S2-3); (l-h-21) + (S2-4); (l-h-21) + (S2-5); (l-h-21) + (S2-6); (l-h-21) + (S2-7); (l-h-21) + (S2-8); (l-h-21) + (S2-9); (I- h-21) + (S2-10); (l-h-21) + (S3-1); (l-h-21) + (S3-2); (l-h-21) + (S3-3); (l-h-21) + (S3-4); (l-h-21) + (S3-5); (l-h-21) + (S3-6); (l-h-21) + (S3-7); (l-h-21) + (S3-8); (l-h-21) + (S3-9); (l-h-21) + (S3-10); (I- h-21 ) + (S3-11 ); (l-h-21 ) + (S4-1 ); (l-h-21 ) + (S4-2); (l-h-21 ) + (S4-3); (l-h-21 ) + (S4-4); (l-h-21 ) + (S4-5); (l-h-21) + (S7-1); (l-h-21) + (S11-1); (l-h-21) + (S11-2); (l-h-21) + (S11-3); (l-h-21) + (S12- 1); (l-h-21) + (S13-1); (l-h-21) + (S13-2); (l-h-21) + (S13-3); (l-h-21) + (S13-4): (l-h-21) + (S13-5); (I- h-21) + (S13-6); (l-h-21) + (S13-7); (l-h-21) + (S13-8); (l-h-21) + (S13-9); (l-h-21) + (S14-1)
(l-h-22) + (S1-1); (l-h-22) + (S1-2); (l-h-22) + (S1-3); (l-h-22) + (S1-4); (l-h-22) + (S1-5); (l-h-22) + (S1-6); (l-h-22) + (S1-7); (l-h-22) + (S1-8); (l-h-22) + (S1-9); (l-h-22) + (S1-10); (l-h-22) + (S1-11); (l-h-22) + (S1-12); (l-h-22) + (S1-13); (l-h-22) + (S2-1); (l-h-22) + (S2-2); (l-h-22) + (S2-3); (l-h-22) + (S2-4); (l-h-22) + (S2-5); (l-h-22) + (S2-6); (l-h-22) + (S2-7); (l-h-22) + (S2-8); (l-h-22) + (S2-9); (I- h-22) + (S2-10); (l-h-22) + (S3-1); (l-h-22) + (S3-2); (l-h-22) + (S3-3); (l-h-22) + (S3-4); (l-h-22) + (S3-5); (l-h-22) + (S3-6); (l-h-22) + (S3-7); (l-h-22) + (S3-8); (l-h-22) + (S3-9); (l-h-22) + (S3-10); (I- h-22) + (S3-11); (l-h-22) + (S4-1); (l-h-22) + (S4-2); (l-h-22) + (S4-3); (l-h-22) + (S4-4); (l-h-22) + (S4-5); (l-h-22) + (S7-1); (l-h-22) + (S11-1); (l-h-22) + (S11-2); (l-h-22) + (S11-3); (l-h-22) + (S12- 1); (l-h-22) + (S13-1); (l-h-22) + (S13-2); (l-h-22) + (S13-3); (l-h-22) + (S13-4): (l-h-22) + (S13-5); (I- h-22) + (S13-6); (l-h-22) + (S13-7); (l-h-22) + (S13-8); (l-h-22) + (S13-9); (l-h-22) + (S14-1)
(l-h-23) + (S1-1); (l-h-23) + (S1-2); (l-h-23) + (S1-3); (l-h-23) + (S1-4); (l-h-23) + (S1-5); (l-h-23) + (S1-6); (l-h-23) + (S1-7); (l-h-23) + (S1-8); (l-h-23) + (S1-9); (l-h-23) + (S1-10); (l-h-23) + (S1-11); (l-h-23) + (S1-12); (l-h-23) + (S1-13); (l-h-23) + (S2-1); (l-h-23) + (S2-2); (l-h-23) + (S2-3); (l-h-23) + (S2-4); (l-h-23) + (S2-5); (l-h-23) + (S2-6); (l-h-23) + (S2-7); (l-h-23) + (S2-8); (l-h-23) + (S2-9); (I- h-23) + (S2-10); (l-h-23) + (S3-1); (l-h-23) + (S3-2); (l-h-23) + (S3-3); (l-h-23) + (S3-4); (l-h-23) + (S3-5); (l-h-23) + (S3-6); (l-h-23) + (S3-7); (l-h-23) + (S3-8); (l-h-23) + (S3-9); (l-h-23) + (S3-10); (I- h-23) + (S3-11); (l-h-23) + (S4-1); (l-h-23) + (S4-2); (l-h-23) + (S4-3); (l-h-23) + (S4-4); (l-h-23) + (S4-5); (l-h-23) + (S7-1); (l-h-23) + (S11-1); (l-h-23) + (S11-2); (l-h-23) + (S11-3); (l-h-23) + (S12- 1); (l-h-23) + (S13-1); (l-h-23) + (S13-2); (l-h-23) + (S13-3); (l-h-23) + (S13-4): (l-h-23) + (S13-5); (I- h-23) + (S13-6); (l-h-23) + (S13-7); (l-h-23) + (S13-8); (l-h-23) + (S13-9); (l-h-23) + (S14-1)
(l-h-24) + (S1-1); (l-h-24) + (S1-2); (l-h-24) + (S1-3); (l-h-24) + (S1-4); (l-h-24) + (S1-5); (l-h-24) + (S1-6); (l-h-24) + (S1-7); (l-h-24) + (S1-8); (l-h-24) + (S1-9); (l-h-24) + (S1-10); (l-h-24) + (S1-11); (l-h-24) + (S1-12); (l-h-24) + (S1-13); (l-h-24) + (S2-1); (l-h-24) + (S2-2); (l-h-24) + (S2-3); (l-h-24) + (S2-4); (l-h-24) + (S2-5); (l-h-24) + (S2-6); (l-h-24) + (S2-7); (l-h-24) + (S2-8); (l-h-24) + (S2-9); (I- h-24) + (S2-10); (l-h-24) + (S3-1); (l-h-24) + (S3-2); (l-h-24) + (S3-3); (l-h-24) + (S3-4); (l-h-24) + (S3-5); (l-h-24) + (S3-6); (l-h-24) + (S3-7); (l-h-24) + (S3-8); (l-h-24) + (S3-9); (l-h-24) + (S3-10); (I- h-24) + (S3-11); (l-h-24) + (S4-1); (l-h-24) + (S4-2); (l-h-24) + (S4-3); (l-h-24) + (S4-4); (l-h-24) + (S4-5); (l-h-24) + (S7-1); (l-h-24) + (S11-1); (l-h-24) + (S11-2); (l-h-24) + (S11-3); (l-h-24) + (S12- 1); (l-h-24) + (S13-1); (l-h-24) + (S13-2); (l-h-24) + (S13-3); (l-h-24) + (S13-4): (l-h-24) + (S13-5); (I- h-24) + (S13-6); (l-h-24) + (S13-7); (l-h-24) + (S13-8); (l-h-24) + (S13-9); (l-h-24) + (S14-1)
Im Rahmen der vorliegenden Erfindung sind insbesondere Kombinationen der Verbindungen der allgemeinen Formel (I) mit den folgenden Safenern bevorzugt: Dai- muron (S14-1), Benoxacor (S3-4), Furilazol [(S3-10) bzw. (S3-11)], Fluxofenim (S11- 2), Fenchlorazol(-ethylester) (S1-7), Mefenpyr-diethyl (S1-1), Cloquintocet-mexyl (S2-1), Isoxadifen-ethyl (S1-11), Cyprosulfamide (S4-1), Flurazole (S13-3), Oxa- betrinil (S11-1), Dichlormid (S3-1) und Dietholate (S13-8).
Im Rahmen der vorliegenden Erfindung sind Kombinationen der Verbindungen der allgemeinen Formel (I) mit den folgenden Safenern besonders bevorzugt: Mefenpyr- diethyl (S1-1), Isoxadifen-ethyl (S1-11), Cyprosulfamide (S4-1), Fenchlorazol- ethylester (S1-7), Benoxacor (S3-4), Cloquintocet-mexyl (S2-1), Fluxofenim (S11-2) und Furilazol [(S3-10) bzw. (S3-11)]. Aus der Reihe der Verbindungen der Formel (I) sind l-a-51, l-a-52, l-a-86, l-b-18, l-c-50, l-d-12 und l-h-8 bevorzugt sowie jeweils die Kombinationen einer dieser 7 vorstehend genannten Verbindungen mit einem der Safenern aus der Gruppe Mefenpyr-diethyl (S1-1), Isoxadifen-ethyl (S1-11), Cyprosulfamide (S4-1), Fenchlorazol- ethylester (S1-7), Benoxacor (S3-4), Cloquintocet-mexyl (S2-1), Fluxofenim (S11-2) und Furilazol [(S3-10) bzw. (S3-11 )].
Herbizid wirksame Menge bedeutet im Sinne der Erfindung eine Menge an einem oder mehreren Herbiziden, die geeignet ist, den Pflanzenwuchs negativ zu beeinflussen. Antidotisch wirksame Menge bedeutet im Sinne der Erfindung eine Menge an einem oder mehreren Safenern, die geeignet ist, die phytotoxische Wirkung von Pflanzenschutzmittelwirkstoffen (z.B. von Herbiziden) an Kulturpflanzen zu reduzieren.
Die Safener (B) eignen sich zur Reduktion phytotoxischer Effekte, die beim Einsatz von Herbiziden der allgemeinen Formel (I) in Nutzpflanzenkulturen auftreten können, ohne die Wirksamkeit dieser herbiziden Wirkstoffe gegen Schadpflanzen wesentlich zu beeinträchtigen. Hierdurch kann das Einsatzgebiet herkömmlicher Pflanzenschutzmittel ganz erheblich erweitert z.B. auf Kulturen, in denen bisher ein Einsatz der Herbizide nicht möglich oder nur beschränkt möglich war.
Die benötigten Aufwandmengen der Safener können je nach Indikation und verwendetem herbiziden Wirkstoff innerhalb weiter Grenzen schwanken und sind in der Regel im Bereich von 0,001 bis 5 kg, vorzugsweise 0,005 bis 2,5 kg Wirkstoff je Hektar. Die herbiziden Wirkstoffe der allgemeinen Formel (I) (A) und die Safener (B) können zusammen (z.B. als fertige Formulierung oder im Tank-mix-Verfahren) oder in beliebiger Reihenfolge nacheinander ausgebracht werden, z.B. durch Sprüh-, Gieß- und Spritzanwendung oder durch Granulatstreuung. Das Gewichtsverhältnis Herbizid der allgemeinen Formel (I) (A) : Safener (B) kann innerhalb weiter Grenzen variieren und liegt vorzugsweise im Bereich von 1 :10000 bis 10000:1 , insbesondere von 1 :1000 bis 1000:1 . Die jeweils optimalen Mengen an der allgemeinen Formel (I) (A) und Safener (B) sind vom Typ des verwendeten Herbizids und des verwendeten Safeners sowie von der Art und dem Entwicklungsstadium des zu behandelnden Pflanzenbestandes abhängig und lassen sich von Fall zu Fall durch einfache, routinemäßige Vorversuche ermitteln.
Die in den erfindungsgemäßen Herbizid-Safener-Kombinationen enthaltenen Safener (B) können je nach ihren Eigenschaften zur Vorbehandlung des Saatgutes der Kulturpflanze (z.B. zur Beizung des Saatguts) verwendet werden oder vor der Saat in die Saatfurchen eingebracht oder zusammen mit dem Herbizid vor oder nach dem Auflaufen der Pflanzen angewendet werden. Vorauflaufbehandlung schließt sowohl die Behandlung der Anbaufläche (einschließlich eventuell auf der Anbaufläche be- findlichen Wassers, z.B. bei Reisapplikationen) vor der Aussaat als auch die Behandlung der angesäten, aber noch nicht bewachsenen Anbauflächen ein. Bevorzugt ist die gemeinsame Anwendung mit dem Herbizid. Hierzu können Tankmischungen oder Fertigformulierungen eingesetzt werden.
In einer bevorzugten Ausführungsform werden das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder Setzlinge mit den Safenern (B), gegebenenfalls in Kombination mit anderen agrochemischen Wirkstoffen, vorbehandelt. Zur Vorbehandlung des Saatguts können die Wirkstoffe z.B. durch Beizung an das Saatgut gebracht oder die Wirkstoffe und das Saatgut können in Wasser oder andere Lösungsmittel gegeben, und die Wirkstoffe z.B. durch Anlagerung oder Diffusion im Tauchverfahren oder durch Quellen oder Vorkeimen aufgenommen werden. Zur Vorbehandlung von Setzlingen können die jungen Pflanzen z.B. durch Spritzen, Tauchen oder Gießen mit den Safenern, gege- benenfalls in Kombination mit anderen agrochemischen Wirkstoffen, in Kontakt gebracht und anschließend verpflanzt und gegebenenfalls mit den Herbiziden (A) nachbehandelt werden.
Die Saatgut- oder Setzlingsbehandlung kann mit den Safenern (B) alleine oder ge- meinsam mit anderen agrochemischen Wirkstoffen - wie Fungiziden, Insektiziden oder Mitteln zur Pflanzenstärkung, Düngung oder zur Beschleunigung der Quell- und Keimungsvorgänge - erfolgen. Dabei können die Safener nach der Vorbehandlungsanwendung anschließend nochmals vor, nach oder gemeinsam mit einem oder mehreren Herbiziden der Formel (I) eventuell auch in Kombination mit anderen bekann- ten Herbiziden angewandt werden. Durch die Vorbehandlung des Saatguts oder der Setzlinge kann eine verbesserte Langzeitwirkung der Safener erzielt werden.
Gegenstand der vorliegenden Erfindung ist somit weiterhin ein Verfahren zur Bekämpfung von unerwünschten Pflanzen in Pflanzenkulturen, das dadurch gekenn- zeichnet ist, dass die Komponenten (A) und (B) der erfindungsgemäßen Herbizid- Safener-Kombinationen auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikoty- le Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vernnehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden, z.B. gemeinsam oder getrennt. Dabei können einer oder mehrere Safener (B), vorzugsweise eine oder mehrere, insbesondere eine, Verbindung der Gruppen (S1 ) bis (S14) vor, nach oder gleichzeitig mit dem oder den Herbizid(en) der allgemeinen Formel (I) (A) auf die Pflanzen, das Saatgut oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), appliziert werden. In einer bevorzugten Ausführungsform werden die Safener (B) zur Saatgutbehandlung eingesetzt. Unter unerwünschten Pflanzen sind alle Pflanzen zu verstehen, die an Orten wachsen, wo sie unerwünscht sind. Dies können z.B. Schadpflanzen (z.B. mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen) sein, z.B. auch solche, die gegen bestimmte herbizide Wirkstoffe wie Glyphosate, Atrazin, Glufosinate oder Imi- dazolinon-Herbizide resistent sind.
Monokotyle Unkräuter entstammen z.B. den Gattungen Echinochloa, Setaria, Pani- cum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleo- charis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alo- pecurus, Apera. Dikotyle Unkräuter entstammen z.B. den Gattungen Sinapis, Lepidi- um, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Sene- cio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesba- nia, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum, Euphorbia.
Bevorzugt wird in dem erfindungsgemäßen Verfahren eine wirksame Menge der Komponenten (A) und (B) zur Bekämpfung von Schadpflanzen angewendet in Pflanzenkulturen, beispielsweise in wirtschaftlich bedeutenden Ackerbaukulturen z.B. monokotylen Ackerbaukulturen wie Getreide (z.B. Weizen, Gerste, Roggen, Hafer), Reis, Mais, Hirse, oder dikotylen Ackerbaukulturen wie Zuckerrübe, Raps, Baumwolle, Sonnenblumen und Leguminosen z.B. der Gattungen Glycine (z.B. Glycine max. wie nicht-transgene Glycine max. (z.B. konventionelle Sorten wie STS-Sorten) oder transgene Glycine max. (z.B. RR-Soja oder LL-Soja) und deren Kreuzungen), Pha- seolus, Pisum, Vicia und Arachis, oder Gemüsekulturen aus verschiedenen botanischen Gruppen wie Kartoffel, Lauch, Kohl, Karotte, Tomate, Zwiebel, sowie Dauer- und Plantagenkulturen wie Kern- und Steinobst, Beerenobst, Wein, Hevea, Bananen, Zuckerrohr, Kaffee, Tee, Citrus, Nussplantagen, Rasen, Palmenkulturen und Forstkulturen.
Gegenstand der Erfindung ist auch die Verwendung der erfindungsgemäßen Herbi- zid-Safener-Kombinationen zur Bekämpfung von unerwünschtem Pflanzenwuchs, vorzugsweise in Pflanzenkulturen.
Die erfindungsgemäßen Herbizid-Safener-Kombinationen können nach bekannten Verfahren z.B. als Mischformulierungen der Einzelkomponenten, gegebenenfalls mit weiteren Wirkstoffen, Zusatzstoffen und/oder üblichen Formulierungshilfsmitteln hergestellt werden, die dann in üblicher Weise mit Wasser verdünnt zur Anwendung gebracht werden, oder als sogenannte Tankmischungen durch gemeinsame Verdünnung der getrennt formulierten oder partiell getrennt formulierten Einzelkomponenten mit Wasser hergestellt werden. Ebenfalls möglich ist die zeitlich versetzte Anwendung (Splitapplikation) der getrennt formulierten oder partiell getrennt formulierten Einzelkomponenten. Möglich ist auch die Anwendung der Einzelkomponenten oder der Herbizid-Safener-Kombinationen in mehreren Portionen (Sequenzanwendung), z. B. nach Anwendungen im Vorauflauf, gefolgt von Nachauflauf- Applikationen oder nach frühen Nachauflaufanwendungen, gefolgt von Applikationen im mittleren oder späten Nachauflauf. Bevorzugt ist dabei die gemeinsame oder die zeitnahe Anwendung der Wirkstoffe der jeweiligen Kombination.
Die erfindungsgemäßen Herbizid-Safener-Kombinationen kann auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gen- technisch veränderten Pflanzen eingesetzt werden.
Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betref- fen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z. B. Hitze, Kälte, Tro- ckenheit, Salz und ultraviolette Strahlung liegen.
Bevorzugt ist die Anwendung der erfindungsgemäßen Herbizid-Safener- Kombinationen oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten.
Vorzugsweise können die Verbindungen der Formel (I) als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Ver- fahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A-0131624). Beschrieben wurden beispielsweise in mehreren Fällen gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/1 1376, WO 92/14827, WO 91/19806),
transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufo- sinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosate (WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind,
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die
Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924, EP- A-0193259).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972).
gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen (EPA 309862, EPA0464461 )
gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398).
Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming")
transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen
transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking")
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind im Prinzip bekannt; siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431 ).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle in Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laborato- ry Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität eines Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressi- onseffektes oder die Expression mindestens eines entsprechend konstruierten Ribo- zyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA- Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 1 1 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflan- zen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen. So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen auf- weisen.
Vorzugsweise können die erfindungsgemäßen Herbizid-Safener-Kombinationen in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Di- camba oder gegen Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactat- synthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydroxyphenyl- pyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Bei der Anwendung der erfindungsgemäßen Herbizid-Safener-Kombinationen in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, veränderte Auf- wandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemä- ßen Herbizid-Safener-Kombinationen zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen.
Bevorzugt ist die Anwendung der erfindungsgemäßen Kombinationen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z. B. von Getrei- de (z.B. Weizen, Gerste, Roggen, Hafer), Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsekulturen. Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemä- ßen Herbizid-Safener-Kombinationen zur Bekämpfung von Schadpflanzen in trans- genen Kulturpflanzen oder Kulturpflanzen, die Toleranz durch Selektionszüchtung aufweisen.
Die Herbizide (A) und die Safener (B) können gemeinsam oder getrennt in übliche Formulierungen z.B. zur Sprüh-, Gieß-, Spritz- und Saatgutbeizanwendung übergeführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Pasten, Granulate, Aerosole, Wirkstoff-imprägnierte Natur- und synthetische Stoffe,
Feinstverkapselungen in polymeren Stoffen. Die Formulierungen können die üblichen Hilfs- und Zusatzstoffe enthalten.
Diese Formulierungen werden in bekannter Weise hergestellt, z.B. durch Vermi- sehen der Wirkstoffe mit Streckmitteln, also flüssigen Lösungsmitteln, unter Druck stehenden verflüssigten Gasen und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Im Falle der Benutzung von Wasser als Streckmittel könne z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im wesentlichen infrage: Aromaten, wie Xylol, Toluol, Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene, oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone, wie Aceton, Methylethylketon, Methyl isobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylformamid oder Dimethylsulfoxid, sowie Wasser. Als feste Trägerstoffe kommen in Frage: z.B. Ammoniumsalze und natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillo- nit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kiesel- säure, Aluminiumoxid und Silikate; als feste Trägerstoffe für Granulate kommen in- frage: z.B. gebrochene und fraktionierte natürliche Gesteine wie Calcit, Marmor, Bims, Sepiolith, Dolomit sowie synthetische Granulate aus anorganischen und organischen Mehlen sowie Granulate aus organischem Material wie Sägemehl, Kokos- nußschalen, Maiskolben und Tabakstengel; als Emulgier-und/oder schaumerzeugende Mittel kommen infrage: z.B. nicht ionogene und anionische Emulgatoren, wie Polyoxyethylen-Fettsäureester, Polyoxyethylen-Fettalkohol-Ether, z.B. Alkylarylpo- lyglykolether, Alkylsulfonate, Alkylsulfate, Arylsulfonate sowie Eiweißhydrolysate; als Dispergiermittel kommen infrage: z.B. Ligninsulfitablaugen und Methylcellulose.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische, pulverige, körnige oder latexformige Polymere verwendet werden, wie Gummiarabicum, Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholi- pide, wie Kephaline und Lecithine und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferro- cyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyanin- farbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden.
Die Formulierungen enthalten im allgemeinen zwischen 0,1 und 95 Gewichtsprozent Wirkstoff, vorzugsweise zwischen 0,5 und 90 Gew.-%. Die Herbizide (A) und die Safener (B) können als solche oder in ihren Formulierungen auch in Mischung mit anderen agrochemischen Wirkstoffen, wie bekannten Herbiziden, zur Bekämpfung von unerwünschtem Pflanzenwuchs, z.B. zur Unkrautbekämpfung oder zur Bekämpfung von unerwünschten Kulturpflanzen Verwendung finden, wobei z.B. Fertigformulierungen oder Tankmischungen möglich sind.
Auch Mischungen mit anderen bekannten Wirkstoffen wie Fungiziden, Insektiziden, Akariziden, Nematiziden; weiteren, nicht genannten Safenern; Schutzstoffen gegen Vogelfraß, Pflanzennährstoffen und Bodenstrukturverbesserungsmitteln sind möglich, ebenso mit im Pflanzenschutz üblichen Zusatzstoffen und Formulierungshilfsmitteln. Die Herbizide (A) und die Safener (B) können als solche, in Form ihrer Formulierungen oder den daraus durch weiteres Verdünnen bereiteten Anwendungsformen, wie gebrauchsfertige Lösungen, Suspensionen, Emulsionen, Pulver, Pasten und Granulate angewandt werden. Die Anwendung geschieht üblicherweise, z.B. durch Gießen, Spritzen, Sprühen, Streuen.
Die Wirkstoffe können auf die Pflanzen, Pflanzenteile, das Saatgut oder die Anbaufläche (Ackerboden) ausgebracht werden, vorzugsweise auf das Saatgut oder die grünen Pflanzen und Pflanzenteile und gegebenenfalls zusätzlich auf den Ackerboden. Eine Möglichkeit der Anwendung ist die gemeinsame Ausbringung der Wirkstof- fe in Form von Tankmischungen, wobei die optimal formulierten konzentrierten Formulierungen der Einzelwirkstoffe gemeinsam im Tank mit Wasser gemischt und die erhaltene Spritzbrühe ausgebracht wird.
Eine gemeinsame Formulierung der erfindungsgemäßen Kombination an Wirkstoffen (A) und (B) hat den Vorteil der leichteren Anwendbarkeit, weil die Mengen der Kom- ponenten bereits im optimalen Verhältnis zueinander eingestellt werden können. Außerdem können die Hilfsmittel in der Formulierung aufeinander optimal abgestimmt werden.
Als Kombinationspartner für die erfindungsgemäßen Herbizid-Safener- Kombinationen in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte, vorzugsweise herbizide Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-Coenzym-A-Carboxylase, PS I, PS II, HPPD, Phytoene-Desaturase, Protoporphyrinogen-Oxidase, Glutamine-Synthetase, Cellulo- sebiosynthese, 5-Enolpyruvylshikimat-3-phosphat-Synthetase beruhen, einsetzbar. Solche Verbindungen und auch andere einsetzbare Verbindungen mit teilweise unbekanntem oder anderem Wirkungsmechanismus sind z.B. in Weed Research 26, 441 -445 (1986), oder in dem Handbuch "The Pesticide Manual", 12. Auflage 2000, oder 13. Auflage 2003 oder 14. Auflage 2006/2007, oder in dem entsprechenden„e- Pesticide Manual", Version 4.1 (2007-08), jeweils herausgegeben vom British Crop Protection Council, (im Folgenden auch kurz "PM"), und dort zitierter Literatur beschrieben. Listen von„Common names" sind auch in„The Compendium of Pesticide Common Names" im Internet verfügbar. Als literaturbekannte Herbizide, die mit den erfindungsgemäßen Mischungen kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (Anmerkung: Die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit dem chemischen Namen, ggf. zusammen mit einer üblichen Codenummer bezeich- net und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind eine und zum Teil auch mehrere Anwendungsformen genannt):
2,4-D, Acetochlor, Acifluorfen, Acifluorfen-sodium, Aclonifen, Alachlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidosulfuron, Aminocyclopyrachlor, Aminopyralid, Amitrole, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflu- butamid, Benazolin, Benazolin-ethyl, Benfuresate, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Bifenox, Bilanafos, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil, Bute- nachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone- ethyl, Chlomethoxyfen, Chloridazon, Chlorimuron-ethyl, Chlornitrofen, Chlorotoluron, Chlorsulfuron, Cinidon-ethyl, Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clo- dinafop-propargyl, Clomazone, Clomeprop, Clopyralid, Cloransulam-methyl, Cumylu- ron, Cyanazine, Cyclosulfamuron, Cycloxydim, Cyhalofop-butyl, Desmedipham, Di- camba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop-methyl, Diclosulam, Difen- zoquat, Diflufenican, Diflufenzopyr, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Triaziflam, Diquat-dibromide, Dithio- pyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron-methyl, Etho- fumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop-ethyl, Fenoxaprop- P-ethyl, Fentrazamide, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-butyl, Fluazifop-P-butyl, Fluazolate, Flucarbazone- sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flumetsulam, Flumiclo- rac-pentyl, Flumioxazin, Fluometuron, Fluorochloridone, Fluoroglycofen-ethyl, Flupo- xam, Flupyrsulfuron-methyl-sodiunn, Fluridone, Fluroxypyr, Fluroxypyr-butoxypropyl, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet-methyl, Fomesafen, Foram- sulfuron, Glufosinate, Glufosinate-P, Glufosinate-ammonium, Glufosinate-P- ammonium, Glufosinate-P-sodium, Glyphosate, Halosulfuron-methyl, Haloxyfop, Ha- loxyfop-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, Imaza- methabenz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Ima- zosulfuron, Indanofan, Indaziflam, lodosulfuron-methyl-natrium, loxynil, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Ketospiradox, Lactofen, Lenacil, Linu- ron, MCPA, Mecoprop, Mecoprop-P, Mefenacet, Mesosulfuron-methyl, Mesotrione, Metamifop, Metamitron, Metazachlor, Methabenzthiazuron, Methiozolin, Methyldym- ron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron- methyl, Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclome- fone, Oxyfluorfen, Paraquat, Pelargonie acid, Pendimethalin, Pendralin, Penoxsu- lam, Pentoxazone, Pethoxamid, Phenmedipham, Picloram, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron-methyl, Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone-sodium, Pro- pyrisulfuron, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen-ethyl, Pyrazolate, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac-methyl, Pyrithiobac-sodium, Quinclorac, Quinmerac, Quinoclamine, Quizalofop-ethyl, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Rimsulfu- ron, Sethoxydim, Simazine, Simetryn, S-Metolachlor, Sulcotrione, Sulfentrazone, Sulfometuron-methyl, Sulfosate, Sulfosulfuron, Tebuthiuron, Tepraloxydim, Ter- buthylazine, Terbutryn, Thenylchlor, Thiazopyr, Thifensulfuron-methyl, Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron-methyl, Triclopyr, Tri- diphane, Trifloxysulfuron, Trifluralin, Triflusulfuron-methyl und Tritosulfuron.
Weitere mögliche Mischungspartner sind Pyroxasulfone, Pyroxsulam, Orthosulfamu- ron, Pyrimisulfan, Prohexadione-Calcium, Bencarbazone, SYN-523, IDH-100, SYP- 249, Monosulfuron, Ipfencarbazone (HOK-e-1 ), Pyribambenz-Isopropyl, Tefuryltrio- ne, Bencarbazone, Tembotrione, Pyrasulfotole, Thiencarbazone-Methyl, Topramezone, Methiozilin, Metazosulfuron, Fenoxasulfone, Saflufenacil, Bicydopyrone (SYN- 449), Methyl 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)pyridine-2- carboxylat [CAS RN 943831 -98-9] und 4-Amino-3-chloro-6-(4-chloro-2-fluoro-3- methoxyphenyl)pyhdine-2-carbonsäure [CAS RN 943832-60-8]. Ganz besonders vorteilhaft als Kombinationspartner für die erfindungsgemäßen Herbizid-Safener-Kombinationen in Mischungsfornnulierungen oder im Tank-Mix sind Atrazine, Fenoxaprop-ethyl, Glufosinate, Glufosinate-ammonium, Glyphosate, Iso- xaflutole, Mesosulfuron-methyl, Mesotrione, S-Metolachlor. Ganz besonders bevorzugt als Kombinationspartner für die erfindungsgemäßen Herbizid-Safener-Kombinationen in Mischungsformulierungen oder im Tank-Mix ist Isoxaflutole.
Zur Anwendung können in handelsüblicher Form vorliegende Formulierungen gege- benenfalls in üblicherweise verdünnt werden, z.B. mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt.
Herbizidwirkung und Safenerwirkung im Vorauflauf
Samen bzw. Rhizomstücke von mono- und dikotylen Unkrautpflanzen und Kulturpflanzen wurden in Torftöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die als wasserlösliche Pulver oder Suspensionen formulierten erfindungsgemäßen Herbizid-Safener-Wirkstoffkombinationen sowie in parallelen Versuchen die entsprechend formulierten Einzelwirkstoffe wurden dann in verschiedenen Dosierun- gen mit einer Wasseraufwandmenge von umgerechnet 300 l/ha auf die Oberfläche der Abdeckerde appliziert. Nach der Behandlung wurden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstums-bedingungen für die Unkräuter und die Kulturpflanzen gehalten. Die optische Bonitur der Pflanzen- bzw. Auflaufschäden erfolgte nach dem Auflaufen der Versuchspflanzen nach einer Versuchszeit von 2 bis 4 Wochen im Vergleich zu unbehandelten Kontrollen.
Herbizidwirkung und Safenerwirkung im Nachauflauf Sannen bzw. Rhizomstücke von mono- und dikotylen Schadpflanzen und von Kulturpflanzen werden in Torftöpfen in sandiger Lehmerde ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. Alternativ hierzu werden im Paddy-Reisanbau vorkommende Schadpflanzen in Töpfen kulti- viert, in denen Wasser bis zu 2 cm über der Bodenoberfläche steht. Zehn bis zwanzig Tage nach der Aussaat werden die Versuchspflanzen im ein bis Dreiblattstadium behandelt. Die als wasserlösliche Pulver oder Suspensionen formulierten erfindungsgemäßen Herbizid-Safener-Wirkstoffkombinationen sowie in parallelen Versuchen die entsprechend formulierten Einzel Wirkstoffe werden in verschiedenen Dosie- rungen mit einer Wasseraufwandmenge von umgerechnet 300 l/ha auf die grünen Pflanzenteile gesprüht und nach 2-3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen die Wirkung der Präparate optisch im Vergleich zu unbehandelten Kontrollen bonitiert. Die Ergebnisse sind in Tabellen A bis E dargestellt und zeigen, dass die Verwendung der erfindungsgemäßen Herbizid-Safener-Kombinationen gegenüber der alleinigen Verwendung des jeweiligen Herbizids zu einer deutlich geringeren Schädigung der Kulturpflanzen führt. Tabelle A: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Mais l-a-86 60 40%
l-a-86 + mefenpyr-diethyl 60 + 100 15% -63% l-a-86 + isoxadifen-ethyl 60 + 100 0% -100% l-a-86 + cyprosulfamide 60 + 100 0% -100% l-a-86 + cloquintocet-mexyl 60 + 100 0% -100% l-a-86 + benoxacor 60 + 100 0% -100% l-a-86 + furilazole 60 + 100 0% -100% l-a-86 + fluxofenim 60 + 100 5% -88% l-a-86 + fenchlorazole-ethyl 60 + 100 20% -50% Tabelle B: Wirkung im Nachauflauf
Figure imgf000190_0001
Tabelle C: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Reis gung in Reis l-a-52 180 5%
l-a-52 + mefenpyr-diethyl 180 + 100 0% -100% l-a-52 + isoxadifen-ethyl 180 + 100 0% -100% l-a-52 + cyprosulfamide 180 + 100 0% -100% l-a-52 + cloquintocet-mexyl 180 + 100 0% -100% l-a-52 + benoxacor 180 + 100 0% -100% l-a-52 + furilazole 180 + 100 0% -100% l-a-52 + fluxofenim 180 + 100 0% -100% l-a-52 + fenchlorazole-ethyl 180 + 100 0% -100% Tabelle D: Wirkung im Nachauflauf
Figure imgf000191_0001
Tabelle E: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Reis gung in Reis l-a-51 180 5%
l-a-51 + mefenpyr-diethyl 180 + 100 0% -50% l-a-51 + isoxadifen-ethyl 180 + 100 0% -100% l-a-51 + cyprosulfamide 180 + 100 0% -100% l-a-51 + cloquintocet-mexyl 180 + 100 0% -100% l-a-51 + benoxacor 180 + 100 0% -100% l-a-51 + furilazole 180 + 100 0% -100% Tabelle F: Wirkung im Nachauflauf
Figure imgf000192_0001
Tabelle G: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Weizen gung in Reis l-b-16 150 13%
l-b-16 + mefenpyr-diethyl 150 + 100 10% -100% l-b-16 + isoxadifen-ethyl 150 + 100 0% -23% l-b-16 + cyprosulfamide 150 + 100 0% -100% l-b-16 + cloquintocet-mexyl 150 + 100 0% -100% l-b-16 + benoxacor 150 + 100 0% -100% l-b-16 + furilazole 150 + 100 0% -100% l-b-16 + fluxofenim 150 + 100 10% -23% l-b-16 + fenchlorazole-ethyl 150 + 100 0% -100% Tabelle H: Wirkung im Nachauflauf
Figure imgf000193_0001
Tabelle I: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Reis gung in Reis l-b-16 75 20%
l-b-16 + mefenpyr-diethyl 75 + 100 0% -100% l-b-16 + isoxadifen-ethyl 75 + 100 0% -100% l-b-16 + cyprosulfamide 75 + 100 0% -100% l-b-16 + cloquintocet-mexyl 75 + 100 5% -75% l-b-16 + benoxacor 75 + 100 0% -100% l-b-16 + furilazole 75 + 100 10% -50% l-b-16 + fluxofenim 75 + 100 5% -75% l-b-16 + fenchlorazole-ethyl 75 + 100 0% -100% Tabelle J: Wirkung im Nachauflauf
Figure imgf000194_0001
Tabelle K: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Gerste gung in Reis l-g-6 300 15%
l-g-6 + mefenpyr-diethyl 300 + 100 0% -100% l-g-6 + isoxadifen-ethyl 300 + 100 0% -100% l-g-6 + cloquintocet-mexyl 300 + 100 0% -100% l-g-6 + benoxacor 300 + 100 0% -100% l-g-6 + furilazole 300 + 100 0% -100% l-g-6 + fluxofenim 300 + 100 10% -33% l-g-6 + fenchlorazole-ethyl 300 + 100 0% -100% Tabelle L: Wirkung im Vorauflauf
Figure imgf000195_0001
Tabelle M: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Reis l-a-92 300 20%
l-a-92 + isoxadifen-ethyl 300 + 100 0% -100% l-a-92 + cyprosulfamide 300 + 100 0% -100% l-a-92 + cloquintocet-mexyl 300 + 100 0% -100% l-a-92 + benoxacor 300 + 100 10% -50% l-a-92 + furilazole 300 + 100 10% -50% l-a-92 + fluxofenim 300 + 100 10% -50% l-a-92 + fenchlorazole-ethyl 300 + 100 5% -75% Tabelle N: Wirkung im Nachauflauf
Figure imgf000196_0001
Tabelle O: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Reis l-a-106 150 30%
l-a-106 + mefenpyr-diethyl 150 + 100 0% -100% l-a-106 + isoxadifen-ethyl 150 + 100 0% -100% l-a-106 + cyprosulfamide 150 + 100 0% -100% l-a-106 + cloquintocet-mexyl 150 + 100 0% -100% l-a-106 + benoxacor 150 + 100 0% -100% l-a-106 + furilazole 150 + 100 0% -100% l-a-106 + fluxofenim 150 + 100 0% -100% l-a-106 + fenchlorazole-ethyl 150 + 100 0% -100% Tabelle P: Wirkung im Nachauflauf
Figure imgf000197_0001
Tabelle Q: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Reis l-c-58 300 5%
l-c-58 + mefenpyr-diethyl 300 + 100 0% -100% l-c-58 + isoxadifen-ethyl 300 + 100 0% -100% l-c-58 + cyprosulfamide 300 + 100 0% -100% l-c-58 + cloquintocet-mexyl 300 + 100 0% -100% l-c-58 + benoxacor 300 + 100 0% -100% l-c-58 + furilazole 300 + 100 0% -100% l-c-58 + fluxofenim 300 + 100 0% -100% l-c-58 + fenchlorazole-ethyl 300 + 100 0% -100% Tabelle R: Wirkung im Nachauflauf
Figure imgf000198_0001
Tabelle S: Wirkung im Nachauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Reis l-c-59 300 70%
l-c-59 + isoxadifen-ethyl 300 + 100 35% -50% l-c-59 + cyprosulfamide 300 + 100 15% -79% l-c-59 + cloquintocet-mexyl 300 + 100 50% -29% l-c-59 + benoxacor 300 + 100 35% -50% l-c-59 + fluxofenim 300 + 100 65% -7% Tabelle T: Wirkung im Vorauflauf
Verbindung Dosierung Schädigung von Minderung der Schädi[g/ha] Mais gung in Reis l-c-59 300 20%
l-c-59 + mefenpyr-diethyl 300 + 100 5% -75% l-c-59 + isoxadifen-ethyl 300 + 100 0% -100% l-c-59 + cyprosulfamide 300 + 100 0% -100% l-c-59 + cloquintocet-mexyl 300 + 100 15% -25% l-c-59 + benoxacor 300 + 100 0% -100% l-c-59 + furilazole 300 + 100 10% -50% l-c-59 + fluxofenim 300 + 100 10% -50%

Claims

Patentansprüche
1 . Herbizid-Safener-Kombinationen, enthaltend
(A) 4-Phenylpyridazinone der Formel (I) oder deren Salze
Figure imgf000200_0001
worin A und B bedeuten unabhängig voneinander jeweils Wasserstoff, (C3-C6)- Cycloalkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (C3-C6)- Cycloalkyl, Phenyl und Halogenphenyl substituiertes (d-C6)-Alkyl, n bedeutet 0, 1 , 2 oder 3;
G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8;
E bedeutet ein Metallionäquivalent oder ein Ammoniunnion;
L bedeutet Sauerstoff oder Schwefel;
M bedeutet Sauerstoff oder Schwefel; R1 bedeutet jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-C-6)- Alkenyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl, Di-(Ci-C4)-alkoxy-(Ci-C6)-alkyl oder (d-C4)- Alkylthio-(Ci-C6)-alkyl,
einen durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d- C4)-Alkoxy substituierten, vollständig gesättigten, 3- bis 6-gliedrigen Ring bestehend aus 3 bis 5 Kohlenstoffatonnen und 1 bis 3 Heteroatomen aus der Gruppe Sauerstoff, Schwefel und Stickstoff,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl, Phenyl-(d-C4)-alkyl, Heteroaryl, Phenoxy-(Ci-C4)-alkyl oder Heteroaryloxy-(d-C4)-alkyl;
R2 bedeutet jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-C3)- Alkenyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl oder Di-(Ci-C4)-alkoxy-(Ci-C6)-alkyl,
oder durch jeweils n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Benzyl;
R3, R4 und R5 bedeuten unabhängig voneinander jeweils durch n Halogenatome substituiertes (d-C6)-Alkyl, (d-C4)-Alkoxy, N-(Ci-C6)-Alkylamino, N,N-Di-(d- C6)-Alkylamino, (d-C4)-Alkylthio, (C2-C4)-Alkenyl oder (C3-C6)-Cycloalkylthio, oder durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Cr C4)-Alkoxy substituiertes Phenyl, Benzyl, Phenoxy oder Phenylthio;
R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff,
durch n Halogenatome substituiertes (d-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C2-Ce)-Al- kenyl, (Ci-C6)-Alkoxy oder (Ci-C4)-Alkoxy-(Ci-C6)-alkyl,
durch jeweils n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)-Alkoxy substituiertes Phenyl oder Benzyl;
oder R6 und R7 bilden gemeinsam mit dem N-Atom, an das sie gebunden sind, einen 3- bis 6-gliedrigen Ring enthaltend 2 bis 5 Kohlenstoffatomen und 0 oder 1 Sauer- stoff- oder Schwefelatome;
R8 bedeutet durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2- 3)-Al kenyl, (C2-C6)-Alkinyl, (Ci-C4)-Alkoxy-(Ci-C6)-alkyl, (C1 -C4)-Al kylth io-(Ci -C4)-al kyl oder Di- (C1 -C4)-al koxy-(Ci -C6)-al kyl ,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl,
einen durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d- C4)-Alkoxy substituierten, vollständig gesättigten, 3- bis 6-gliedrigen Ring bestehend aus 3 bis 5 Kohlenstoffatonnen und 1 bis 3 Heteroatomen aus der Gruppe Sauerstoff, Schwefel und Stickstoff,
durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes Phenyl, Phenyl-(d-C4)-alkyl, Heteroaryl, Phenoxy-(d-C4)-alkyl oder Heteroaryloxy-(Ci -C4)-al kyl ; und bedeutet Wasserstoff, (d-C6)-Alkyl oder (C3-C6)-Cycloalkyl, bedeutet Halogen, Cyano, Nitro, Halogen-(d-C6)-alkyl, Halogen-(Ci C6)-alkoxy, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy oder durch n Halogenatome substituiertes Phenyl,
bedeutet Wasserstoff, Halogen, Cyano, Nitro, (d-C6)-Alkyl,
Halogen-(Ci-C6)-alkyl, Halogen-(Ci-C6)-alkoxy, (C3-C6)-Cycloalkyl oder durch n Halogenatome substituiertes Phenyl; oder b) X bedeutet Halogen, Cyano, Nitro oder jeweils durch n Halogenatome substituiertes (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C C6)-Alkoxy oder Phenyl;
Y und Z bedeuten unabhängig voneinander jeweils Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl oder durch jeweils n Halogenatome substituiertes (Ci-C6)-Alkyl, (CrC6)-Alkoxy oder Phenyl, und
(B) einen oder mehrere Safener,
wobei solche Herbizid-Safener-Kombinationen ausgenommen sein sollen, in denen der Index n für Null steht und der Safener Fenchlorazol-ethyl, Cloquintocet-mexyl oder Mefenpyr-diethyl ist.
2. Herbizid-Safener-Kombinationen nach Anspruch 1 , worin
A bedeutet Wasserstoff, (d-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-
(C3-C6)-alkyl, Benzyl oder Halogenphenyl-(d-C6)-alkyl; B bedeutet Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl- (d-C6)-alkyl, Benzyl oder Halogenphenyl-(d-C6)-alkyl; n bedeutet 0, 1 , 2 oder 3; G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8;
E bedeutet Na+, K+, (Mg2+)1/2, (Ca2+)i 2 ,R13R14R15R16N+ oder NH4+; R13, R14, R15 und R16 bedeuten unabhängig voneinander (Ci-C6)-Alkyl oder Benzyl; L bedeutet Sauerstoff; M bedeutet Sauerstoff;
R1 bedeutet durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder jeweils durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Phenyl-(d-C4)-alkyl; R2 bedeutet durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder jeweils durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (Ci-C4)- Alkoxy substituiertes (C3-C6)-Cycloalkyl, Phenyl oder Benzyl;
R3, R4 und R5 bedeuten unabhängig voneinander jeweils durch n Halogenatome substituiertes (Ci-Ce)-Alkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Benzyl; R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff, durch n Halogenatome substituiertes (d-C6)-Alkyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (d-C4)-Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Benzyl;
R8 bedeutet durch n Halogenatome substituiertes (d-C6)-Alkyl, (C2-Ce)-Alkenyl, (C2- C6)-Alkinyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)- Alkyl und (d-C4)-Alkoxy substituiertes Phenyl oder Phenyl-(d-C4)-alkyl; und a) X bedeutet Wasserstoff, Methyl, Ethyl oder cyclo-Propyl;
Y bedeutet Halogen, Cyano, Nitro, Halogen-(d-C6)-alkyl, Halogen- (d-C6)-alkoxy, (C3-C6)-Cycloalkyl, (Ci-Ce)-Alkoxy oder durch n
Halogenatome substituiertes Phenyl,
Z bedeutet Wasserstoff, Halogen, Halogen-(d-C6)-alkyl, (d-C6)-Alkoxy, Halogen-(d-C6)-alkoxy, (C3-C6)-Cycloalkyl oder durch n Halogenatome substituiertes Phenyl; oder b) X bedeutet Halogen, Cyano, Nitro, Halogen-(d-C6)-alkyl, Halogen-(d-
C6)-alkoxy, (C C6)-Alkoxy oder (C3-C6)-Cycloalkyl;
Y bedeutet Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl, durch jeweils n Halogenatome substituiertes (d-C6)-Alkyl, (Ci-Ce)-Alkoxy oder Phenyl;
Z bedeutet Wasserstoff, Halogen, Cyano, Nitro, (C3-C6)-Cycloalkyl oder durch jeweils n Halogenatome substituiertes (d-C6)-Alkyl, (C1-C6)- Alkoxy oder Phenyl.
3. Herbizid-Safener-Kombinationen nach Anspruch 1 , worin
A bedeutet Wasserstoff, Methyl, Ethyl, i-Butyl, cyclo-Propyl, cyclo-Propylmethyl,
Benzyl, 2-Chlorphenylmethyl, 3-Chlorphenylmethyl oder 4-Chlorphenylmethyl; B bedeutet Wasserstoff, Methyl, Ethyl, i-Butyl, t-Butyl, cyclo-Propyl, cyclo- Propylmethyl, Benzyl, 2-Chlorphenylmethyl, 3-Chlorphenylmethyl oder 4- Chlorphenylmethyl, n bedeutet 0, 1 , 2 oder 3;
G bedeutet Wasserstoff, C(=O)R1, C(=L)MR2, SO2R3, P(=L)R4R5, C(=L)NR6R7, E oder R8; E bedeutet Na+, K+, (Mg2+)i/2, (Ca2+)i 2, (CH3)4N+ oder NH4 +;
L bedeutet Sauerstoff;
M bedeutet Sauerstoff;
R1 bedeutet (Ci-C6)-Alkyl oder (C3-C6)-Cycloalkyl;
R2 bedeutet (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl oder Benzyl; R3, R4 und R5 bedeuten unabhängig voneinander jeweils (d-C6)-Alkyl, Phenyl oder Benzyl;
R6 und R7 bedeuten unabhängig voneinander jeweils Wasserstoff, (d-C6)-Alkyl, Phenyl oder Benzyl;
R8 bedeutet (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl oder durch n Reste aus der Gruppe bestehend aus Halogen, (Ci-C4)-Alkyl und (C C4)-Alkoxy substituiertes Benzyl; und a) X bedeutet Wasserstoff, Methyl oder Ethyl; bedeutet Fluor, Brom, Chlor, lod, Cyano, Nitro, cyclo-Propyl, Methoxy, Ethoxy, Trifluormethyl oder Trifluormethoxy, Phenyl oder Halogenphenyl;
bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methoxy, Ethoxy, Triflu ormethyl oder cyclo-Propyl;
b) X bedeutet Fluor, Brom, Chlor, lod, Cyano, Nitro, Methoxy, Ethoxy,
Trifluormethyl, Trifluormethoxy oder cyclo-Propyl
Y bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methyl, Ethyl, Methoxy,
Ethoxy, Trifluormethyl, Trifluormethoxy oder cyclo-Propyl; Z bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, Methyl, Ethyl, Methoxy, Ethoxy, Trifluormethyl, Trifluormethoxy, cyclo-Propyl, Chlorphenyl oder Fluorphenyl.
4. Herbizid-Safener-Kombinationen nach einem der Ansprüche 1 bis 3, worin A bedeutet Wasserstoff oder (Ci-C2)-Alkyl;
B bedeutet (Ci-C2)-Alkyl;
G bedeutet Wasserstoff, C(=O)R1 , C(=L)MR2, SO2R3 oder R8; L bedeutet Sauerstoff; M bedeutet Sauerstoff; R1 bedeutet (Ci-C2)-Alkyl,
R2 bedeutet (d-C2)-Alkyl, bedeutet (Ci-C2)-Alkyl, bedeutet (C2-C6)-Alkinyl, und bedeutet Methyl oder Ethyl;
bedeutet Fluor, Brom, Chlor oder lod;
bedeutet Wasserstoff, Fluor, Brom, Chlor, lod, (C3-C6)-Cycloalkyl
bedeutet Fluor, Brom, Chlor oder lod;
bedeutet Fluor, Brom, Chlorjod, Methyl oder Ethyl;
bedeutet Methyl, Ethyl, Fluor, Brom, Chlor, lod oder Trifluormethoxy.
5. Herbizid-Safener-Kombinationen nach einem der Ansprüche 1 bis 4, worin A bedeutet Wasserstoff oder Methyl;
B bedeutet Methyl;
G bedeutet Wasserstoff, C(=O)R1 , C(=L)MR2, SO2R3 oder R8;
L bedeutet Sauerstoff;
M bedeutet Sauerstoff; R1 bedeutet Methyl, bedeutet Ethyl, bedeutet Methyl, bedeutet Propinyl und bedeutet Ethyl;
bedeutet Chlor;
bedeutet Wasserstoff, Fluor oder Cyclopropyl oder bedeutet Brom oder Chlor;
bedeutet Ethyl;
bedeutet Methyl, Fluor oder Trifluormethoxy.
6. Herbizid-Safener-Kombinationen nach einem der Ansprüche 1 bis 5, worin die Safener ausgewählt sind aus den Gruppen,
S1 ) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate:
S1 a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure, wie
1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure, 1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure- ethylester (S1 -1 ) ("Mefenpyr-diethyl");
Derivate der Dichlorphenylpyrazolcarbonsäure, wie 1 -(2,4-Dichlorph
5-methylpyrazol-3-carbonsäureethylester, 1 -(2,4-Dichlorphenyl)-5- isopropylpyrazol-3-carbonsäureethylester, 1 -(2,4-Dichlorphenyl)-5- (1 ,1 -dimethyl-ethyl)pyrazol-3-carbonsäureethylester; Derivate der 1 ,5-Diphenylpyrazol-3-carbonsäure (S1 c), wie
1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester,
1 -(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester; S1 d) Verbindungen vom Typ der Triazolcarbonsäuren (S1 d), wie Fenchlorazol(- ethylester);
S1 e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure, oder der 5,5-Diphenyl-2-isoxazolin-3-carbonsäure(S1 e), wie
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester,
5-Phenyl-2-isoxazolin-3-carbonsäureethylester, 5,5-Diphenyl-2-isoxazolin- carbonsäure, 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester,
5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbonsäureethylester; S2) Verbindungen aus der Gruppe der 8-Chinolinyloxyderivate (S2):
S2a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), wie
(5-Chlor-8-chinolinoxy)essigsäure-(1 -methylhexyl)-ester,
(5-Chlor-8-chinolinoxy)essigsäure-(1 ,3-dimethyl-but-1 -yl)-ester,
(5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester,
(5-Chlor-8-chinolinoxy)essigsäure-1 -allyloxy-prop-2-ylester,
(5-Chlor-8-chinolinoxy)essigsäureethylester,
(5-Chlor-8-chinolinoxy)essigsäuremethylester,
(5-Chlor-8-chinolinoxy)essigsäureallylester,
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-1 -ethylester (S2-8), (5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-1 -ylester und deren
Hydrate und Salze, wie Lithium-, Natrium- Kalium-, Kalzium-, Magnesium-, Aluminium-, Eisen-, Ammonium-, quartäre Ammonium-, Sulfonium-, oder Phosphoniumsalze; S2b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, (5-Chlor-8-chinolinoxy)malonsäurediallylester,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester;
Wirkstoffe vom Typ der Dichloracetamide (S3), wie
Dichlormid,
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-1 ,3-oxazolidin),
"R-28725" (3-Dichloracetyl-2,2,-dimethyl-1 ,3-oxazolidin),
Benoxacor,
"PPG-1292" (N-Allyl-N-[(1 ,3-dioxolan-2-yl)-methyl]-dichloracetamid),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid),
"AD-67" oder "MON 4660" (3-Dichloracetyl-1 -oxa-3-aza-spiro[4,5]decan), "TI-35" (1 -Dichloracetyl-azepan), Dicyclonon;
((RS)-1 -Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[1 ,2-a]pyrimidin-6-on), "Furilazol" sowie dessen (R)-Isomer;
Verbindungen aus der Klasse der Acylsulfonamide:
-Acylsulfonamide der Formel (S4a) und deren Salze,
Figure imgf000210_0001
worin
RA1 (CrC6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch vA Substituenten aus der Gruppe Halogen, (d-C4)Alkoxy, (Ci-Ce)Halo- alkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch durch (d-C4)Alkyl und (d-C4)Haloalkyl substituiert sind;
RA 2 Halogen, (d-C4)Alkyl, (d-C4)Alkoxy, CF3;
mA 1 oder 2;
vA ist 0, 1 , 2 oder 3 bedeuten;
Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze,
Figure imgf000211_0001
worin
RB1 , RB2 unabhängig voneinander Wasserstoff, (Ci-C-6)Alkyl,
(C3-C6)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl,
RB 3 Halogen, (d-C4)Alkyl, (d-C4)Haloalkyl oder (d-C4)Alkoxy und ΠΓΙΒ 1 oder 2 bedeuten,
S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylharnstoffe der ForC),
Figure imgf000211_0002
worin
Rc1, Rc2 unabhängig voneinander Wasserstoff, (Ci-CsJAlkyl,
(C3-C8)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl,
Rc3 Halogen, (d-C4)Alkyl, (d-C4)Alkoxy, CF3
nric 1 oder 2 bedeuten;
Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch- aliphatischen Carbonsäurederivate (S5), wie
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoe säure, 3,5-Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicycl säure, 2-Hydroxyzimtsäure, 2,4-Dichlorzimtsäure,
S6) Wirkstoffe aus der Klasse der 1 ,2-Dihydrochinoxalin-2-one (S6), z.B.
1 -Methyl-3-(2-thienyl)-1 ,2-dihydrochinoxalin-2-on, 1 -Methyl-3-(2-thienyl)-1 ,2- dihydrochinoxalin-2-thion, 1 -(2-Aminoethyl)-3-(2-thienyl)-1 ,2-dihydro- chinoxalin-2-on-hydrochlorid, 1 -(2-Methylsulfonylaminoethyl)-3-(2-thienyl)-1 ,2- dihydro-chinoxalin-2-οη,
57) Verbindungen aus der Klasse der Diphenylmethoxyessigsäuredehvate (S7), z.B. Diphenylmethoxyessigsäuremethylester,
Diphenylmethoxyessigsäureethylester und Diphenylmethoxyessigsäure;
58) Verbindungen der Formel (S8),
Figure imgf000212_0001
worin die Symbole und Indizes folgende Bedeutungen haben:
RD 1 ist Halogen, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy,
RD2 ist Wasserstoff oder (d-C4)Alkyl
RD3 ist Wasserstoff, (Ci-C8)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, oder Aryl, wobei jeder der vorgenannten C-haltigen Reste unsubstituiert oder durch einen oder mehrere, vorzugsweise bis zu drei gleiche oder verschiedene Reste aus der Gruppe, bestehend aus Halogen und Alkoxy substituiert ist; oder deren Salze nD ist eine ganze Zahl von 0 bis 2.
Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone S10) Verbindungen der Formeln (S10a) oder (S10b)
Figure imgf000212_0002
(S10a) (S10b)
worin
RE 1 Halogen, (d-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 YE, ZE unabhängig voneinander O oder S
nE eine ganze Zahl von 0 bis 4,
RE2 (Ci-Ci6)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl,
RE3 Wasserstoff oder (Ci-Ce)Alkyl bedeuten.
51 1 ) Wirkstoffe vom Typ der Oxyimino-Verbindungen, wie
Oxabetrinil, Fluxofenim und Cyomet nil;
512) Wirkstoffe aus der Klasse der Isothiochromanone, wie Methyl-[(3-oxo-1 H-2- benzothiopyran-4(3H)-yliden)methoxy]acetat;
513) Eine oder mehrere Verbindungen aus Gruppe (S13) wie
1 ,8-Naphthalindicarbonsäureanhydrid,
Fenclorim, Flurazole, "CL 304415" (CAS-Reg.Nr. 31541 -57-8);
(4-Carboxy-3,4-dihydro-2H-1 -benzopyran-4-essigsäure);
2-Dichlormethyl-2-methyl-1 ,3-dioxolan;
"MG-838" (CAS-Reg.Nr. 133993-74-5);
(2-propenyl 1 -oxa-4-azaspiro[4.5]decan-4-carbodithioat);
Disulfoton, Dietholate, Mephenate;
514) Dimepiperate, Daimuron, Cumyluron, Methoxyphenon, 1 -Brom-4- (chlormethylsulfonyl)benzol. (CAS-Reg.Nr. 54091 -06-4);
S15) Verbindungen der Formel (S15) oder deren Tautomere
Figure imgf000213_0001
worin
einen (d-C6)Haloalkylrest bedeutet und
Wasserstoff oder Halogen bedeutet und RH4 unabhängig voneinander Wasserstoff, (d-Ci6)Alkyl, (C2-Ci6)Alkenyl oder (C2-Ci6)Alkinyl,
wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, [(d-C4)Alkoxy]-carbonyl, [(d-C4)Haloalkoxy]- carbonyl, (C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist,
oder (C3-C6)Cycloalkyl, (C4-C6)Cycloalkenyl, (C3-C6)Cycloalkyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesättigten oder ungesättigten carbocyclischen Ring kondensiert ist,
wobei jeder der letztgenannten 4 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (d-C4)Alkyl, (d-C4)Haloalkyl, (d-C4)Alkoxy, (d-C4)Haloalkoxy, (d-C4)Alkylthio, (CrC4)Alkylamino, Di[(CrC4)alkyl]-amino, [(Ci -C4)AI koxyj-carbonyl , [(Ci -C4)Haloal koxyj-carbonyl ,
(C3-C6)Cycloalkyl, das unsubstituiert oder substituiert ist, Phenyl, das unsubstituiert oder substituiert ist, und Heterocyclyl, das unsubstituiert oder substituiert ist, substituiert ist,
bedeutet oder
(d-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und
Wasserstoff oder (d-C4)-Alkyl bedeutet oder
und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis acht- gliedrigen heterocydischen Ring, der neben dem N-Atom auch weitere Hete- roringatome, vorzugsweise bis zu zwei weitere Heteroringatome aus der Gruppe N, O und S enthalten kann und der unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Cyano, Nitro, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (d-C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet.
S16) Safener aus der Gruppe umfassend die Verbindungen
(2,4-Dichlorphenoxy)essigsäure (2,4-D),
(4-Chlorphenoxy)essigsäure,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure,
4-(4-Chlorphenoxy)buttersäure,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),
1 -(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl). 7. Herbizid-Safener-Kombinationen nach einem der Ansprüche 1 bis 6, worin die Safener ausgewählt sind aus der Gruppe umfassend die Verbindungen Daimuron, Benoxacor, Furilazol, Fluxofenim, Fenchlorazol-ethyl, Mefenpyr-diethyl, Cloquinto- cet-mexyl, Isoxadifen-ethyl, Cyprosulfamide, Flurazole, Oxabetrinil, Dichlormid und Dietholate.
8. Herbizid-Safener-Kombinationen nach Ansprüche 7, worin die Safener ausgewählt sind aus der Gruppe umfassend die Verbindungen Benoxacor, Furilazol, Fluxofenim, Fenchlorazol-ethyl, Mefenpyr-diethyl, Cloquintocet-mexyl, Isoxadifen- ethyl und Cyprosulfamide.
9. Herbizid-Safener-Kombinationen nach einem der Ansprüche 1 bis 8 enthaltend ein weiteres von Verbindungen der Formel (I) unterschiedliches Herbizid.
10. Herbizid-Safener-Kombinationen nach Ansprüche 9, worin das weitere Herbi- zid ausgewählt ist aus der Gruppe umfassend die Verbindungen Atrazine, Feno- xaprop-ethyl, Glufosinate, Glufosinate-ammonium, Glyphosate, Isoxaflutole, Meso- sulfuron-methyl, Mesotrione und S-Metolachlor.
1 1 . Herbizide Mittel, gekennzeichnet durch einen herbizid wirksamen Gehalt an einer Herbizid-Safener-Kombinationen gemäß einem der Ansprüche 1 bis 10.
12. Herbizide Mittel nach Anspruch 1 1 in Mischung mit Formulierungshilfsmitteln.
13. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, daß man eine wirksame Menge einer Herbizid-Safener-Kombinationen gemäß einem der Ansprüche 1 bis 10 oder eines herbiziden Mittels gemäß Anspruch 1 1 oder 12 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert.
14. Verwendung von Herbizid-Safener-Kombinationen gemäß einem der Ansprüche 1 bis 10 oder eines herbiziden Mittels gemäß Anspruch 1 1 oder 12 zur Bekämp- fung unerwünschter Pflanzen.
15. Verwendung nach Anspruch 14, dadurch gekennzeichnet, daß die Herbizid- Safener-Kombinationen zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden.
16. Verwendung nach Anspruch 15, dadurch gekennzeichnet, daß die Nutzpflanzen transgene Nutzpflanzen sind.
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