WO2011138280A2 - Combinaison herbicides-phytoprotecteurs contenant des arylpyridazinones et des phytoprotecteurs - Google Patents

Combinaison herbicides-phytoprotecteurs contenant des arylpyridazinones et des phytoprotecteurs 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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WO2011138280A3 (fr
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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

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne des combinaisons herbicides-phytoprotecteurs contenant des 4-phénlpyridazinones de formule (I) et des phytoprotecteurs. Dans la formule (I), A, B, G, X, Y et Z représentent hydrogène, halogène, nitro et des radicaux organiques tels que : alkyl, alcoxy et halogénoalkyl.
PCT/EP2011/056965 2010-05-04 2011-05-02 Combinaison herbicides-phytoprotecteurs contenant des arylpyridazinones et des phytoprotecteurs WO2011138280A2 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2023189602A1 (fr) * 2022-03-30 2023-10-05 石原産業株式会社 Composé de pyridazinone ou sel de celui-ci et agent de lutte contre les organismes nuisibles le contenant

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Publication number Priority date Publication date Assignee Title
WO2023189602A1 (fr) * 2022-03-30 2023-10-05 石原産業株式会社 Composé de pyridazinone ou sel de celui-ci et agent de lutte contre les organismes nuisibles le contenant

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