WO2020002083A1 - Substituted heterocyclic pyrrolones and salts thereof and use thereof as herbicidal agents - Google Patents

Substituted heterocyclic pyrrolones and salts thereof and use thereof as herbicidal agents Download PDF

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WO2020002083A1
WO2020002083A1 PCT/EP2019/066188 EP2019066188W WO2020002083A1 WO 2020002083 A1 WO2020002083 A1 WO 2020002083A1 EP 2019066188 W EP2019066188 W EP 2019066188W WO 2020002083 A1 WO2020002083 A1 WO 2020002083A1
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phenyl
methyl
fluoro
alkyl
bromo
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PCT/EP2019/066188
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German (de)
French (fr)
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Jana FRANKE
Hendrik Helmke
Jens Frackenpohl
Uwe Döller
Thomas Müller
Dirk Schmutzler
Elisabeth ASMUS
Anu Bheemaiah MACHETTIRA
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Bayer Aktiengesellschaft
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Publication of WO2020002083A1 publication Critical patent/WO2020002083A1/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • 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
    • A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
    • 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
    • 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
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
  • this invention relates to substituted heterocyclylpyrrolones and their salts, processes for their preparation and their use as herbicides.
  • Crop crops or active ingredients to combat undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or an inadequate herbicidal activity against certain harmful plants, (b) the spectrum of the harmful plants is too small to combat with an active ingredient can be (c) insufficient selectivity in crops and / or (d) have a toxicologically unfavorable profile.
  • active ingredients which can be used as plant growth regulators in some crop plants lead to undesirably reduced crop yields in other crop plants or are incompatible or only compatible with the crop plant in a narrow range of application rates.
  • Some of the known active ingredients cannot be economically manufactured on an industrial scale because of precursors and reagents that are difficult to access, or they have insufficient chemical stabilities. For other active substances, the effect depends too much on environmental conditions such as weather and soil conditions.
  • One object of the present invention is therefore to provide compounds with herbicidal activity (herbicides) which are highly effective against economically important harmful plants even at relatively low application rates and preferably against good activity
  • Harmful plants can be used selectively in crop plants and preferably show good tolerance to crop plants.
  • these herbicidal compounds should, in particular, be effective and efficient against a wide range of grasses, and preferably also have good effectiveness against many weeds.
  • pyrrolones which carry heterocyclic substituents on the nitrogen, for example also optionally further substituted isoxazolines.
  • Substituted pyrrolones and their herbicidal or pesticidal properties are also described in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 and EP0286816 carry heterocyclic substituents, for example optionally further substituted isoxazolines.
  • Selected specially substituted 1,3,4-thiadiazolyl- and 1,2,4-thiadiazolyl-2,5-dioxoimidazolines and their herbicidal activity are described in DE2247266. Substituted pyrazolylpyrrolones and their use as herbicides
  • Active ingredients are described, for example, in WO2015 / 018434.
  • the present invention therefore relates to compounds of the general formula (1)
  • R U R 12 where R 10 , R 1 1 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for halogen, cyano, (Ci-Cg) alkyl, (Ci-C8) haloalkyl, (Ci-Cg) hydroxyalkyl, (C i - C s) -
  • R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-Cg) alkoxy, (C3-Cio) cycloalkyl- (Ci-C8) alkoxy, aryl- (Ci-Cg) -alkoxy, (Ci -C8) alkoxy- (Ci-C8) alkoxy, arylcarbonyloxy, (Ci-Cs) - alkylcarbonyloxy, aryl- (Ci-C8) alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 10 ) - cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci -C8) haloalkylcarbonyloxy, (C 2 -C 8 ) alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , OSO 2 R 16
  • R 3 represents hydrogen, (Ci-Cg) alkyl
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C8) -alkyl, (Ci-C 8 ) -hydroxyalkyl, (Ci-C 8 ) - Haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8 ) - alkyl, (Ci-Csj-alkoxy, aryl, heteroaryl, heterocyclyl, aryl- (Ci-Cg) - alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-C8) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C8) -alkoxycarbonyl- (Ci-Cs)
  • R 10 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (C 3 -Cio) -cycloalkyl, (C3-C10) - cycloalkyl- (Ci-Cg) -alkyl, aryl, heteroaryl, Heterocyclyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (C4-Cio) cycloalkenyl, aryl- (C 2 -Cg) alkenyl, heteroaryl- (C 2 -Cg)
  • R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-Cs) - alkyl, (Ci-Cs) - haloalkyl, (C3-Cio) -cycloalkyl, (C3-Cio) -cycloalkyl- (Ci-Cs ) alkyl, (Ci-Cs) alkoxy, aryl, heteroaryl, heterocyclyl, aryl (Ci-Cs) alkyl, heteroaryl (Ci-Cs) alkyl, heterocyclyl (Ci-Cs) alkyl, (C 2 -Cs) alkenyl, (C 2 -Cs) alkynyl, (Ci-C 8 ) alkoxycarbonyl- (Ci-Cs) alkyl, (Ci-Cs) - alkoxy- (Ci-Cs) alkyl, arylcarbonyloxy - (Ci-Cs) -
  • R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cs) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (Ci-C 8 ) - Cyanoalkyl, (Ci-C 8 ) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C8) -alkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloal
  • R 15 represents (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C2-C 8 ) -alkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -haloalkyl,
  • R 16 is for (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C2-C 8 ) alkyl, (Ci-C 8 ) cyanoalkyl, (Ci-Cio) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -Cio) cycloalkenyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -
  • the compounds of the general formula (1) can form salts. Salt formation can take place by the action of a base on those compounds of the general formula (1) which are acidic
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali or
  • These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
  • Alkaline earth metal salts especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR ' R '' R '' ] + +, where R to R '"are each independent an organic residue from each other,
  • Alkyl sulfonium and alkyl sulfoxonium salts such as (Ci-C 4 ) -trialkyl sulfonium and (Ci-C 4 ) -trialkyl sulfoxonium salts are also suitable.
  • the compounds of the general formula (I) can be added by adding a suitable organic compound.
  • inorganic or organic acid such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
  • mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3
  • organic acids e.g. B.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p
  • Suitable substituents which are in deprotonated form e.g. Sulphonic acids or carboxylic acids can exist, internal salts with protonatable groups such as amino groups.
  • substituted heteroarylpyrrolones of the general formula (I) according to the invention can, depending on external conditions, such as pH, solvent and temperature, be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (I).
  • a independently of one another represents O (oxygen), or the grouping NR 10 or CR U R 12 , where R 10 , R 11 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below to have,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for halogen, cyano, (Ci-Cv) -alkyl, (Ci-Cvj-haloalkyl, (Ci-Cv) -hydroxyalkyl, (C 1-C7) -
  • R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-C7) alkoxy, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkoxy, aryl- (Ci-C7) alkoxy , (Ci-C7) alkoxy- (Ci-C7) alkoxy, (Ci-C7) alkylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, 0-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, 0-fluorophenylcarbonyloxy , Benzylcarbonyloxy, (C3-C9) -cycloalkylcarbonyloxy,
  • R 3 represents hydrogen, (Ci-C7) -alkyl
  • R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (Ci-C 7 ) -hydroxyalkyl, (Ci-C 7 ) - Haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy- (Ci C7) alkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2 , 3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluoroph
  • R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (C1-C7) -
  • R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cv) alkyl, (Ci-Cv) cyanoalkyl, (Ci-Cv) haloalkyl, (Ci-C7) alkoxy- (Ci Cv) alkyl, phenyl, 2-fluoro-phenyl,
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 -
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-
  • R 3 represents hydrogen, methyl, ethyl
  • Q stands for one of the groupings Ql .1 to Ql .69 specifically mentioned in the following table
  • Very particularly preferred subject matter of the invention are compounds of general formula (I), wonn X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentyl
  • R 3 represents hydrogen
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
  • R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-
  • Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
  • X and Y independently of one another represent CH or the grouping CR 1 , where
  • X stands for CH if Y stands for the grouping CR 1 and
  • X stands for the grouping CR 1 , if Y stands for CH,
  • R 1 represents chlorine, bromine, methyl, ethyl, 1-methylethyl, l, l-dimethylethyl, trifluoromethyl, methoxy, ethoxy, methoxymethyl, methylthio, ethylthio, phenyl,
  • R 2 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
  • Methylethylcarbonyloxy 1, 1-dimethylethylcarbonyloxy, 2-methylpropylcarbonyloxy, cyclopropylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy,
  • R 3 represents hydrogen
  • Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
  • alkylsulfonyl alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms for example (but not limited to) (Ci-C 6 ) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, l, l-dimethylethylsulfonyl, pentyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l, l-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonylsulfonyl, 1-methyls
  • heteroarylsulfonyl represents optionally substituted pyridylsulfonyl
  • Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
  • alkylthio alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6 Carbon atoms, such as (Ci-Cio) -, (GG,) - or (Ci-C4) -alkylthio, for example (but not limited to) (Ci-C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, l, l-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio Ethylpropyl
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means one via a
  • (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfmyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfmyl, 2-methylpropylsulfinyl,
  • Alkoxy means an alkyl radical bonded via an oxygen atom, eg. B. (but not limited to) (Ci-C 6 ) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2- Methylpropoxy, l, l-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l, l-dimethylbutoxy, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1- ethylbutoxy, 2-ethylbutoxy, l,
  • Alkenyloxy means an alkenyl radical bonded via an oxygen atom
  • alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10), (C 2 -C 6 ) or (C 2 -C 4 ) alkenoxy or (C3-C10) -, (C3-C 6 ) - or (C3-C 4 ) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
  • the number of carbon atoms refers to the alkyl radical in the
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
  • the number of carbon atoms relates to the alkyl radical in the alkylcarbonyloxy group.
  • the number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes multi-cyclic systems such as
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkyl, haloalkyl, haloalkyl Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alky
  • Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
  • heterocyclic radical contains at least one heterocyclic ring
  • ( carbocyclic ring in which at least one C atom is replaced by a hetero atom, preferably by a hetero atom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or is heteroaromatic and can be unsubstituted or substituted, the binding site being located on a ring atom.
  • the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings.
  • heterocyclyl In the case of optionally substituted heterocyclyl, multi-cyclic systems are also included, such as, for example, 8-azabicyclo [3.2.l] octanyl, 8-azabicyclo [2.2.2] octanyl or l-azabicyclo [2.2.l] heptyl. In the case of optionally substituted heterocyclyl also
  • the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
  • Oxygen atoms are said to be directly adjacent, for example with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3- dihydro-lH-pyrrole
  • 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from group N,
  • O and S such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2- or
  • 6-yl l, 4,5,6-tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; l, 6-dihydropyriazin-l- or 3- or 4- or 5- or 6-yl;
  • 1,2-dithiolan-3- or 4-yl 1,2-dithiolan-3- or 4-yl; 3H-l, 2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2- or 4-yl; l, 3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-l, 2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-
  • 1,2-dithiin-3- or 4-yl 1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; l, 3-dithian-2- or 4- or 5-yl; 4H-l, 3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
  • 6- or 7-yl 2,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1, 4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3, 4, 7-tetrahydro-l, 4-oxazepin-2
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1, 4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-dioxa
  • heterocycles listed above are preferably, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and also oxo and thioxo.
  • the oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 (also briefly SO2) in the heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie. H.
  • heteroaryls are, for example, 1H-pyrrol-l-yl; lH-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms are part of a further aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • Isoquinolines e.g.
  • heteroaryl are also 5- or 6-membered benzo-fused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H- Indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, l-benzofuran 6-yl, l-benzofuran-7-yl, l-benzothiophene-2-yl, l-benzothiophene-3-yl, 1-benzothiophene-4-yl, l-benzothiophene-5-yl, l-benzothiophene-6- yl, l-benzothioph
  • halogen means fluorine, chlorine, bromine or iodine. If the term is used for a radical, "halogen" means a fluorine, chlorine, bromine or iodine atom.
  • alkyl means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally substituted one or more times and is referred to in the latter case as “substituted alkyl”.
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred.
  • the prefix "bis” also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means alkyl or alkenyl or alkynyl which is partially or completely substituted by identical or different halogen atoms, e.g. monohaloalkyl
  • ( Monohalogenalkyl) such as B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as
  • the term perhaloalkyl also includes the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, and the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as, for example, B. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
  • Partially fluorinated haloalkyl means a straight-chain or branched, saturated Hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, all other halogen atoms which may be present being selected from the group consisting of fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (Ci-C4) -alkyl mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the
  • Range specification for carbon atoms includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals with a larger specified range of carbon atoms e.g. B. "(Ci-C 6 ) alkyl”, also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie, according to the example, also the alkyl radicals with 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in composite radicals, are the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Residues with a double bond or
  • alkenyl also includes straight-chain or branched open-chain ones
  • Hydrocarbon radicals with more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as, for example, allenyl (1,2-propadienyl), 1,1 2-butadienyl and l, 2,3-pentatrienyl.
  • Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6) alkenyl such as ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-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, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, l, 2-d
  • alkynyl also includes straight-chain or branched open-chain ones
  • alkynyl means e.g. Ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl- 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, l-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-p
  • cycloalkyl means a carbocyclic, saturated ring system with preferably 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
  • Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, substituents also having a double bond on
  • Cycloalkyl radical e.g. B. an alkylidene group such as methylidene are included.
  • alkylidene group such as methylidene
  • multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.0] butan-1-yl, bicyclo [1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 - yl, bicyclo [l.
  • (C3-C7) cycloalkyl means a shorthand notation for cycloalkyl of three to seven
  • spirocyclic aliphatic systems are also included, such as, for example, spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, or 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l, 3-Cyclohexadienyl or 1, 4-Cyclohexadienyl, whereby also substituents with a Double bond on the cycloalkenyl radical, e.g. B.
  • the explanations for substituted cycloalkyl apply accordingly.
  • alkylidene e.g. B. also in the form (Ci-Cio) alkylidene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.
  • Cycloalkylidene means a
  • Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
  • Alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
  • Alkylthioalkyl stands for an alkylthio radical bonded via an alkyl group
  • Alkylthioalkylthio means an alkylthioalkyl radical bonded via an oxygen atom.
  • Arylalkoxyalkyl stands for an aryloxy radical bonded via an alkyl group
  • Heteroaryloxyalkyl means a heteroaryloxy radical bonded via an alkyl group.
  • Haloalkoxyalkyl stands for a bound haloalkoxy radical and “Haloalkylthioalkyl” means a haloalkylthio radical bound via an alkyl group.
  • Arylalkyl stands for an aryl radical bonded via an alkyl group
  • heteroarylalkyl means a heteroaryl radical bonded via an alkyl group
  • heterocyclylalkyl means a heterocyclyl radical bonded via an alkyl group.
  • Cycloalkylalkyl stands for a cycloalkyl radical bonded via an alkyl group, eg. B. (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1 - cyclopropyleth-l -yl, 2-cyclopropyleth-l-yl, l-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.
  • Arylalkenyl stands for an aryl radical bonded via an alkenyl group
  • heteroarylalkenyl means a heteroaryl radical bonded via an alkenyl group
  • heterocyclylalkenyl means a heterocyclyl radical bonded via an alkenyl group
  • Arylalkynyl stands for an aryl group bonded via an alkynyl group
  • heteroarylalkynyl means a heteroaryl group bonded via an alkynyl group
  • heterocyclylalkynyl means a heterocyclyl group bonded via an alkynyl group.
  • haloalkylthio alone or as part of a chemical group - stands for straight-chain or branched S -haloalkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2 , 2,2-difluoroeth-l-ylthio, 3,3,3-prop-l-ylthio.
  • Halocycloalkyl and “Halocycloalkenyl” mean by identical or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g.
  • l-fluorocycloprop-l-yl 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, l-fluorocyclobut-l-yl, l-trifluoromethylcycloprop-l-yl, 2-trifluoromethylcycloprop-1-yl, 1-chloro-cycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.
  • the compounds of the general formula (I) can be present as stereoisomers.
  • the possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I).
  • enantiomers, diastereomers, Z and E isomers are all encompassed by the general formula (I).
  • diastereomers Z and E isomers
  • enantiomers and diastereomers can occur.
  • Stereoisomers can be derived from the at
  • stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances.
  • the invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not specified with their specific stereoform, and to mixtures thereof. For the sake of simplicity, however, the following always refers to compounds of the general formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • the cleaning can also be carried out by
  • the substituted heterocyclylpyrrolones of the general formula (I) according to the invention can be prepared starting from known processes. The used and examined
  • Synthesis routes are based on commercially available or easily prepared partially saturated heterocyclic amines and on appropriately substituted furanones or furandions.
  • the groupings Q, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 R 13 , R 14 , R 15 and R 16 of the general formula (I) have the meanings defined above in the diagrams below.
  • An optionally further substituted heterocyclic amine Q-NFb (IV) is prepared as the first key intermediate for the synthesis of the compounds of the general formula (I) according to the invention.
  • This is shown by way of example, but not by way of limitation, in the synthesis of an optionally further substituted 2-amino-isoxazoline (IVa).
  • an aldehyde or ketone (II) is reacted with diethyl (cyanomethyl) phosphonate in the corresponding substituted nitrile (III) in an olefinization reaction and into the by reaction with V-hydroxycarbamide using a suitable base (e.g. NaOMe) desired substituted heterocyclic amine Q-NFb (IV) transferred (see. Bioorg. Med. Chem. 2003, 11, 4093; Bull. Chim. Soc. France 1973, 1138).
  • R 6 and R 7 are exemplary but not restrictive of hydrogen, and R 4 and R 5 have the meaning previously defined.
  • the monosubstituted furan-2,5-diones (VI), which are also referred to as maleic anhydrides, can be prepared via synthesis instructions known from the literature (cf. J. Chem. Soc., Perkin Trans. 1, 1982, 215; EP1426365; J. Org Chem. 1998, 63, 2646; WO2015 / 018431; Tetrahedron 2012, 68, 5863; Russian J. Org. Chem. 2007, 43, 801), for example compounds (VI-1) and (VI-2) in the following scheme 2 in several steps from a suitable acetylenedicarboxylic acid ester (V).
  • Substituted heterocyclylpyrrolone of the general formula (I) can in two steps
  • a suitable optionally substituted partially saturated heterocyclylamine Q-NFh (IV) with a suitable optionally further substituted maleic anhydride (VI) using a suitable base (e.g. pyridine) in a suitable polar aprotic solvent (e.g. acetonitrile) or under acidic conditions using a suitable acid (e.g.
  • Acetic acid or p-toluenesulfonic acid in toluene as solvent and subsequent reduction of a carbonyl group of the substituted maleimide (VII) formed.
  • the reduction can be carried out in a suitable solvent (e.g. tetrahydrofuran and methanol) with the aid of a suitable reducing agent and can lead to regioisomers (VIII).
  • a suitable solvent e.g. tetrahydrofuran and methanol
  • Reducing agents are, for example, sodium hydride, lithium aluminum hydride, sodium borohydride or other hydrogen-generating metal hydrides. Alternatively, it can be one
  • Transition metal-mediated hydrogenation can be carried out (cf. CH633678, DE2247266,
  • substituted heterocyclylpyrrolones of the general formula (Ia) can be prepared starting from the reaction of a hydroxy- or bromolactone (IX) with a suitable, optionally substituted, partially saturated heterocyclylamine Q-NH2 (IV) in a suitable solvent (for example toluene) at elevated temperature become.
  • a suitable solvent for example toluene
  • acetic anhydride using a suitable base (e.g. pyridine) at elevated
  • Acetic acid and water can be converted into the corresponding heterocyclylpyrrolone of the general formula (Ia) with a free OH group.
  • R 2 of the general formula (1) is exemplary but not restricting OH, OC (0) CH 3 and R 3 of the general formula (1) is an example, but not limiting, of hydrogen.
  • substituted heterocyclylpyrrolones of the general formula (I) have a free hydroxy function
  • this can be acylated with suitable reagents (for example using a suitable acid chloride and with the aid of a suitable base such as triethylamine in a suitable polar-aprotic solvent), sulfonylated (e.g. using a suitable sulfonyl chloride and using a suitable base such as triethylamine in a suitable polar aprotic solvent), alkylated (e.g.
  • R 2 of the general formula (1) is exemplary but not restrictive of OH, OCH3, OSO2CH3, OC (0) CH 3 and OC (0) OCH 3 and R 3 of the general formula (1) represents, by way of example, but not by way of limitation, hydrogen.
  • N-Hydroxyurea (17.185 g, 221.4 mmol, 1.05 equiv) was dissolved in methanol (442 mL) and solid NaOMe (11.96 g 221.4 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-ethylcrotonitrile (20.07 g, 210.9 mmol, 1.00 equiv) in MeOH (210 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 27 h.
  • N-Hydroxyurea (2,993 g, 38.6 mmol, 1.05 equiv) was dissolved in methanol (77 mL) and solid NaOMe (2.13 g 38.6 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-tert-butylacrylonitrile (4.01 g, 36.7 mmol, 1.00 equiv) in MeOH (36.7 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 22 h.
  • N-Hydroxyurea (3,143 g, 40.5 mmol, 1.05 equiv) was dissolved in methanol (81 mL) and solid NaOMe (2.23 g 40.5 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of tetrahydro-4H-pyran-4-ylidene) acetonitrile (5.00 g, 38.6 mmol, 1.00 equiv) in MeOH (38.5 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 6 h.
  • IV-hydroxyurea (0.398 g, 5.13 mmol, 1.10 equiv) was dissolved in methanol (10-2 mL) and solid NaOMe (0.277 g, 5.13 mmol, 1.10 equiv) was added. The solution was stirred for 15 min and then a solution consisting of cyclohexene-1-carbonitrile (0.5 g, 4.67 mmol, 1.00 equiv) in MeOH (4.6 mL) was added. The reaction mixture was transferred to a microwave vessel and irradiated in the microwave at 120-140 ° C. for 6.5 hours. After adding more
  • Citraconic anhydride (308 mg, 2.69 mmol, 1.05 equiv), and 5,5-dimcthyl-4/7-isoxazol-3-amine (380 mg, 2.56 mmol, 1.00 equiv) were dissolved in acetic acid (10 ml) and for 10 h heated under reflux. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Citraconic anhydride (1,074 g, 9.4 mmol, 1.05 equiv), and 4/7-isoxazol-3-amine (1,000 g, 8.9 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and heated under reflux for 3 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. By column chromatography purification (gradient
  • Citraconic anhydride 1,000 g, 9.4 mmol, 1.0 equiv
  • 5-ethyl-5-methyl-4 // - isoxazol-3-amine (1,177 g, 9.2 mmol, 1.05 equiv) were dissolved in acetic acid (40 ml) and 1.5 for hours at reflux heated. After about 5 minutes. the solution turns orange and then turns brownish. After this
  • Citraconic anhydride (167 mg, 1.46 mmol, 1.05 equiv), and 3a, 4,5,6,7,7a-hexahydro-1,2-benzoxazol-3-amine (212 mg, 1.39 mmol, 1.00 equiv) were dissolved in acetic acid ( 10 ml) dissolved and heated under reflux for a total of 17.5 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Citraconic anhydride (235 mg, 2.06 mmol, 1.05 equiv), and 5- (4-chlorophenyl) -4H-isoxazol-3-amine (500 mg, 1.96 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and combined for 3.5 h heated under reflux for a long time. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure.
  • Bromomaleic anhydride (854 mg, 4.7 mmol, 1.2 equiv), and 5-ethyl-5-methyl-4 // - isoxazol-3-amine (500 mg, 3.9 mmol, 1.0 equiv) were in dry toluene under protective gas (10 ml) mixed and stirred for 10.5 h at room temperature with the addition of Amberlyst 15 (50 mg). The reaction mixture was filtered and the solvent removed under reduced pressure.
  • the reaction mixture was stirred for 20 min at room temperature and propionic acid chloride (0.06 mL, 0.68 mmol, 1.10 equiv) was added dropwise.
  • Table 1.1 Particularly preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.1-1 to 1.1-69 of Table 1.1 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.2-1 to 1.2- 69 of table 1.2 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.3-1 to 1.3- 69 of table 1.3 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.4-1 to 1.4- 69 of table 1.4 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.5-1 to 1.5- 69 of Table 1.5 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.6-1 to 1.6- 69 of table 1.6 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-69, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.8-1 to 1.8- 69 of Table 1.8 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.9-1 to 1.9- 69 of Table 1.9 are thus by the meaning of the respective entries No. 1 to 69 for Q of the table
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.10-1 to 1.10-69 of table 1.10 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.11-1 to 1.11-69 of table 1.11 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.12-1 to 1.12-69 of table 1.12 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.13-1 to 1.13-69 of table 1.13 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.14-1 to 1.14-69 of table 1.14 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.15-1 to 1.15-69 of table 1.15 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.16-1 to 1.16-69 of table 1.16 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.17-1 to 1.17-69 of table 1.17 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.18-1 to 1.18-69 of table 1.18 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.19-1 to 1.19-69 of table 1.19 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.20-1 to 1.20-69 of table 1.20 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.21-1 to 1.21-69 of table 1.21 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.22 Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.22-1 to 1.22-69 of table 1.22 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.23-1 to 1.23-69 of table 1.23 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.24-1 to 1.24-69 of table 1.24 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.25-1 to 1.25-69 of table 1.25 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.26-1 to 1.26-69 of table 1.26 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.27-1 to 1.27-69 of table 1.27 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.28-1 to 1.28-69 of table 1.28 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.29-1 to 1.29-69 of table 1.29 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.30-1 to 1.30-69 of table 1.30 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.31-1 to 1.31-69 of table 1.31 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.32-1 to 1.32-69 of table 1.32 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.33-1 to 1.33-69 of table 1.33 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.34-1 to 1.34-69 of table 1.34 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.35-1 to 1.35-69 of table 1.35 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.36-1 to 1.36-69 of table 1.36 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.37-1 to 1.37-69 of table 1.37 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.38-1 to 1.38-69 of table 1.38 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.39-1 to 1.39-69 of table 1.39 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.40-1 to 1.40-69 of table 1.40 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.41-1 to 1.41-69 of table 1.41 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.42-1 to 1.42-69 of table 1.42 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.43-1 to 1.43-69 of table 1.43 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.44-1 to 1.44-69 in Table 1.44 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.45-1 to 1.45-69 of table 1.45 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.46-1 to 1.46-69 of table 1.46 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.47-1 to 1.47-69 of table 1.47 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.48-1 to 1.48-69 of table 1.48 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.49-1 to 1.49-69 in table 1.49 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.50-1 to 1.50-69 of table 1.50 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.51-1 to 1.51-69 of table 1.51 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.52-1 to 1.52-69 of table 1.52 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.53-1 to 1.53-69 of table 1.53 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.54-1 to 1.54-69 of table 1.54 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.55-1 to 1.55-69 of table 1.55 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.56-1 to 1.56-69 of table 1.56 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.57-1 to 1.57-69 of table 1.57 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.58-1 to 1.58-69 of table 1.58 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.59-1 to 1.59-69 of table 1.59 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.60-1 to 1.60-69 of table 1.60 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.61-1 to 1.61-69 in table 1.61 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.62-1 to 1.62-69 of table 1.62 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.63-1 to 1.63-69 of table 1.63 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.67-1 to 1.67-69 of table 1.67 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.68-1 to 1.68-69 of table 1.68 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.69-1 to 1.69-69 in table 1.69 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.70-1 to 1.70-69 of table 1.70 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.71-1 to 1.71-69 of table 1.71 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.72-1 to 1.72-69 in table 1.72 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.73-1 to 1.73-69 of table 1.73 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.74-1 to 1.74-69 of table 1.74 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.75-1 to 1.75-69 of table 1.75 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.76-1 to 1.76-69 of table 1.76 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.77-1 to 1.77-69 of table 1.77 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.78-1 to 1.78-69 of table 1.78 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.79-1 to 1.79-69 of table 1.79 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.80-1 to 1.80-69 of table 1.80 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.81-1 to 1.81-69 of table 1.81 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.82-1 to 1.82-69 of table 1.82 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.83 Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.83-1 to 1.83-69 in Table 1.83 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.84 Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.84-1 to 1.84-69 of table 1.84 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.85 Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.85-1 to 1.85-69 of table 1.85 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.86 Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.86-1 to 1.86-69 in table 1.86 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.87 Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.87-1 to 1.87-69 in Table 1.87 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.88 Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.88-1 to 1.88-69 in table 1.88 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.89 Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.89-1 to 1.89-69 of table 1.89 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.90 Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.90-1 to 1.90-69 of table 1.90 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.91 Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.91-1 to 1.91-69 of table 1.91 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.92 Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.92-1 to 1.92-69 in table 1.92 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.93 Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.93-1 to 1.93-69 in table 1.93 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.94 Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.94-1 to 1.94-69 in table 1.94 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.95 Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-69, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.96 Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.97 Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-69, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.98 Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.98-1 to 1.98-69 of table 1.98 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.99 Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.99-1 to 1.99-69 of table 1.99 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.100 Preferred compounds of the formula (I. 100) are the compounds I. 100-1 to I. 100- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 100-1 to I. 100-69 of Table I. 100 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.101 Preferred compounds of the formula (1.101) are the compounds 1. 101-1 to 1. 101- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 101-1 to I. 101-69 of Table I. 101 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1. (1,102)
  • Preferred compounds of the formula (I. 102) are the compounds I. 102-1 to I. 102- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 102-1 to I. 102-69 of table I. 102 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.103 Preferred compounds of the formula (1.103) are the compounds I. 103-1 to I. 103- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 103-1 to I. 103-69 of table I. 103 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
  • Table 1.104 Preferred compounds of the formula (1. 104) are the compounds 1. 104-1 to 1. 104- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 104-1 to 1. 104-69 of table 1. 104 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.105 Preferred compounds of the formula (I. 105) are the compounds I. 105-1 to I. 105- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 105-1 to I. 105-69 of Table I. 105 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 106) are the compounds I. 106-1 to I. 106- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 106-1 to I. 106-69 of Table I. 106 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 107) are the compounds I. 107-1 to I. 107- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 107-1 to I. 107-69 of Table I. 107 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.108)
  • Table 1.108 Preferred compounds of the formula (I. 108) are the compounds I. 108-1 to I. 108- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 108-1 to I. 108-69 of Table I. 108 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.109 Preferred compounds of the formula (1. 109) are the compounds 1. 109-1 to 1. 109- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 109-1 to 1. 109-69 of table 1. 109 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.110 Preferred compounds of the formula (I.110) are the compounds I.110-1 to I.110-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I.110-1 to I.110-69 of Table I.110 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.111 Preferred compounds of the formula (I. 111) are the compounds I. 111-1 to I. 111- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 111-1 to I. 111-69 of Table I. 111 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.112 Preferred compounds of the formula (I. 112) are the compounds I. 112-1 to I. 112- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 112-1 to I. 112-69 of Table I. 112 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.113 Preferred compounds of the formula (1. 113) are the compounds 1. 113-1 to 1. 113- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 113-1 to 1. 113-69 of Table 1. 113 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.114 Preferred compounds of the formula (1. 114) are the compounds 1. 114-1 to 1. 114- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 114-1 to 1. 114-69 of Table 1. 114 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.115 Preferred compounds of the formula (I. 115) are the compounds I. 115-1 to I. 115- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 115-1 to I. 115-69 of Table I. 115 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.116 Preferred compounds of the formula (I. 116) are the compounds I. 116-1 to I. 116- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 116-1 to I. 116-69 of Table I. 116 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 117) are the compounds I. 117-1 to I. 117- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 117-1 to I. 117-69 of Table I. 117 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.118 Preferred compounds of the formula (I. 118) are the compounds I. 118-1 to I. 118- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 118-1 to I. 118-69 of Table I. 118 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,119 Preferred compounds of the formula (1,119) are the compounds 1,119-1 to 1,119-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 119-1 to 1. 119-69 of Table 1. 119 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,120)
  • Table 1.120 Preferred compounds of the formula (I.120) are the compounds I.120-1 to I.120-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 120-1 to I. 120-69 of Table I. 120 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,121 Preferred compounds of the formula (I. 121) are the compounds I. 121-1 to I. 121- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 121-1 to I. 121-69 of Table I. 121 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 122) are the compounds I. 122-1 to I. 122- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 122-1 to I. 122-69 of Table I. 122 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.123 Preferred compounds of the formula (I. 123) are the compounds I. 123-1 to I. 123- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 123-1 to I. 123-69 of Table I. 123 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,124 Preferred compounds of the formula (I. 124) are the compounds I. 124-1 to I. 124- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the compounds I. 124-1 to I. 124-69 of Table I. 124 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,125 Preferred compounds of the formula (1,125) are the compounds 1,125-1 to 1,125-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 125-1 to 1. 125-69 of Table 1. 125 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.126)
  • Table 1,126 Preferred compounds of the formula (I. 126) are the compounds I. 126-1 to I. 126- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 126-1 to I. 126-69 of Table I. 126 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1,127 Preferred compounds of the formula (I 127) are the compounds I 127-1 to I 127- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 127-1 to I. 127-69 of Table I. 127 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.128 Preferred compounds of the formula (I. 128) are the compounds I. 128-1 to I. 128- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 128-1 to I. 128-69 of Table I. 128 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,129)
  • Table 1,129 Preferred compounds of the formula (I. 129) are the compounds I. 129-1 to I. 129- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 129-1 to I. 129-69 of Table I. 129 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.130 Preferred compounds of the formula (I.130) are the compounds I.130-1 to I.130-69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 130-1 to I. 130-69 of Table I. 130 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.131 Preferred compounds of the formula (1. 131) are the compounds 1. 131-1 to 1. 131- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 131-1 to 1. 131-69 of table 1. 131 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,132)
  • Preferred compounds of the formula (I. 132) are the compounds I. 132-1 to I. 132- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 132-1 to I. 132-69 of Table I. 132 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Preferred compounds of the formula (I. 133) are the compounds I. 133-1 to I. 133- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 133-1 to I. 133-69 of Table I. 133 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.134 Preferred compounds of the formula (I. 134) are the compounds I. 134-1 to I. 134- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 134-1 to I. 134-69 of Table I. 134 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.135)
  • Table 1.135 Preferred compounds of the formula (I. 135) are the compounds I. 135-1 to I. 135- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 135-1 to I. 135-69 of Table I. 135 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.136 Preferred compounds of the formula (I. 136) are the compounds I. 136-1 to I. 136- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections I. 136-1 to I. 136-69 of Table I. 136 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • Table 1.137 Preferred compounds of the formula (1. 137) are the compounds 1. 137-1 to 1. 137- 69, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1. 137-1 to 1. 137-69 of Table 1. 137 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; d2 (intensity2);; d; (intensity ⁇ ;; d (intensity ⁇ ).
  • the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the real relationships of the signal intensities. For wide signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
  • the peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%).
  • stereoisomers and / or impurities can be typical of each
  • An expert who calculates the peaks of the target compounds using known methods can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classic 1H NMR interpretation.
  • the present invention furthermore relates to the use of one or more
  • herbicide and / or plant growth regulator preferably in crops of useful and / or ornamental plants.
  • the present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the preferred or particularly preferred
  • the present invention also relates to a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably marked
  • the present invention also relates to methods for combating
  • Propagation organs such as tubers or shoots with buds
  • the soil in or on which the plants grow e.g. the soil of cultivated or non-cultivated land
  • the area under cultivation i.e. the area on which the plants will grow
  • the compounds according to the invention or the agents according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods.
  • Some representatives of the mono- and dicotyledons are examples
  • Weed flora which can be used to control the compounds according to the invention, without any restriction to certain species being mentioned.
  • the present invention therefore also relates to a method for combating
  • Plant crops in which one or more compound (s) according to the invention is applied to the plants for example harmful plants such as monocotyledonous or dicotyledon weeds or undesirable crop plants
  • the seeds for example grains, seeds or vegetative propagation organs such as tubers or shoots with buds
  • the area which the plants grow e.g. the area under cultivation.
  • the compounds according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence or post-emergence methods.
  • Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention, without any intention that the name should limit them to certain species.
  • the compounds according to the invention are applied to the earth's surface prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), then either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage, but then they grow and eventually die completely after three to four weeks.
  • the compounds according to the invention can have selectivities in crops and can also be used as non-selective herbicides.
  • crop plants of economically important crops are e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
  • the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants.
  • the transgenic plants are generally notable for particularly advantageous properties, for example resistance to certain active ingredients used in the agricultural industry, especially certain herbicides,
  • Resistance to plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to the crop, for example, in terms of quantity, quality, storability, composition and special ingredients.
  • transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known.
  • Further special properties are tolerance or resistance to abiotic stressors such as heat, cold, dryness, salt and ultraviolet radiation.
  • the compounds of the general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the compounds of the general formula (I) can preferably be used as herbicides in
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • new plants with modified properties can be created using genetic engineering methods (see e.g. EP 0221044, EP 0131624).
  • genetic engineering modifications of crop plants for the purpose of modifying the starch synthesized in the plants for example WO 92/011376 A, WO 92/014827 A, WO 91/019806 A
  • transgenic crop plants which are active against certain herbicides of the glufosinate see, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or against combinations or
  • transgenic crop plants for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A).
  • Bacillus thuringiensis toxins Bacillus thuringiensis toxins
  • transgenic crop plants with modified fatty acid composition (WO 91/013972 A).
  • transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of, for example, the new properties mentioned above (“gene stacking”)
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences.
  • standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added.
  • Adapters or linkers can be attached to the fragments for connecting the DNA fragments to one another, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 1996
  • the production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product.
  • DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
  • the synthesized protein can be located in any compartment of the plant cell.
  • the coding region can be linked, for example, to DNA sequences which ensure localization in a specific compartment.
  • sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be any plants
  • the compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. 2,4-D, dicamba or against herbicides, the essential plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), respectively against herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active substances, or against any combination of these active substances, or against any combination of these active substances.
  • the essential plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD)
  • ALS Inhibit acetolactate
  • the compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones.
  • the compounds according to the invention can very particularly preferably be used in transgenic crop plants such as, for. B. corn or soy with the trade name or the designation OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.
  • the invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • cereals preferably maize, wheat, barley, rye, oats, millet or rice, in the pre- or post-emergence.
  • Pre-or post-soya use is also preferred.
  • Plant growth regulation also includes the case in which the active ingredient of the general formula (I) or its salt is formed from a precursor substance (“prodrug”) only after application to the plant, in the plant or in the soil.
  • the invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts is applied to the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in or on which the plants grow, or the cultivated area.
  • the invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
  • (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
  • one or more further agrochemically active substances preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
  • component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual”, 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
  • a herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) selected in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
  • formulation auxiliaries selected in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances,
  • the compounds according to the invention can be used in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules.
  • the invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. As
  • Formulation options are possible, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powder
  • EC emulsifiable concentrates
  • EW emulsions
  • SC Suspension concentrates
  • SC dispersions based on oil or water, oil
  • the necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen,
  • combinations with other pesticidally active substances such as insecticides, acaricides, herbicides, fungicides, as well as with safeners and fertilizers, can also be carried out and / or produce growth regulators, for example in the form of a finished formulation or as a tank mix.
  • Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents,
  • Dispersants e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutylnaphthalene-sulfonic acid sodium or else sodium.
  • the herbicidal active ingredients are, for example, finely ground in customary equipment, such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents
  • surfactants of ionic and / or nonionic type emulsifiers
  • alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether
  • Sorbitan fatty acid esters or polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
  • Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
  • Talc natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants such as those e.g. already listed above for the other types of formulation.
  • Emulsions e.g. Oil-in-water emulsions (EW) can be mixed using stirrers,
  • Solvents and optionally surfactants e.g. already listed above for the other formulation types.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of Carriers such as sand, kaolinite or granulated inert material.
  • Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
  • Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
  • the active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Powdery
  • sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient.
  • Water-dispersible granules the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used.
  • the active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • a wettable powder which is readily dispersible in water is obtained by 25
  • alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight
  • Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of
  • a water-dispersible granulate is also obtained by
  • the compounds of general formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
  • Growth regulators can be used in combination, e.g. as a finished formulation or as
  • Tank mixes The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined.
  • acetolactate synthase As a combination partner for the compounds according to the invention in mixture formulations or in a tank mix, there are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenyl pyruvate dioxygenase, phytoendesaturase,
  • Photosystem I, Photosystem 11 or protoporphyrinogen oxidase are used, e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein.
  • known herbicides or plant growth regulators are mentioned by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (1SO) or with the chemical name or with the code number are designated. All forms of use such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers are always included, even if these are not explicitly mentioned.
  • herbicidal mixture partners examples include:
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mixing partners are:
  • Safeners which, in combination with the compounds of the general formula (I) according to the invention and, if appropriate, in combinations with other active compounds, Insecticides, acaricides, herbicides,
  • Fungicides as listed above can preferably be selected from the group consisting of:
  • n A is a natural number from 0 to 5, preferably 0 to 3;
  • R A 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C i) alkoxy, nitro or (Ci-C 4 ) haloalkyl;
  • W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, with at least one N atom and at most one O atom being contained in the ring, preferably a residue from the group (W A 1 ) to (W A 4 ),
  • n 0 or 1
  • R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered
  • Heterocycle with at least one N atom and up to 3 heteroatoms preferably from the groups O and S, which is connected via the N atom to the carbonyl group in (S1) and is unsubstituted or by residues from the group (Ci-C i) Alkyl, (Ci-C i) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR A 3 , NHR A 4 or N (CH3) 2, in particular of the formula ORA 3 ;
  • R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • R A 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • R A 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COOR A 9 , where R A 9 is hydrogen, ( Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 6 ) hydroxyalkyl, (C3-Ci2) cycloalkyl or tri- (Ci -C 4 ) alkyl silyl;
  • R A 6 , R A 7 , R A 8 are identical or different hydrogen, (Ci-Cs) alkyl, (Ci-Cs) haloalkyl, (C3-Ci2) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (Sl a ) type, preferably compounds such as 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
  • Ethyl 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Sl-9) and related compounds as described in WO-A- 91/08202 are described, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-L 1) ("Isoxadifen- ethyl ") or -n-propyl ester (S1-12) or the
  • Patent application WO-A-95/07897 are described.
  • RB 1 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, nitro or (Ci-C4) haloalkyl;
  • ne is a natural number from 0 to 5, preferably 0 to 3;
  • R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3 to 7-membered heterocycle with at least one N atom and up to 3
  • Heteroatoms preferably from the group O and S, which is connected via the N atom to the carbonyl group in (S2) and is unsubstituted or by radicals from the group (Ci-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR B 3 , NHR B 4 or N (CH3) 2, in particular of the formula OR B 3 ;
  • RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
  • RB 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
  • T B is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted with one or two (Ci-C4) alkyl radicals or with [(Ci-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolineoxyacetic acid (S2 a ) type, preferably
  • Rc 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) cycloalkyl, preferably dichloromethyl;
  • Rc 2 , Rc 3 are the same or different hydrogen, (Ci-C 4 ) alkyl, (C2-C 4 ) alkenyl, (C2-C 4 ) alkynyl, (Ci-C 4 ) haloalkyl, (C2-C 4 ) haloalkenyl , (Ci-C 4 ) alkylcarbamoyl- (Ci-C 4 ) alkyl, (C2-C 4 ) alkenylcarbamoyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, dioxolanyl - (Ci-C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring
  • R-29148 (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
  • R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
  • PPG-1292 N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide
  • TI-35 (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
  • a D is S0 2 -NR D 3 -C0 or C0-NR D 3 -S0 2
  • X D is CH or N
  • RD 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
  • R D 2 is halogen, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) alkylsulfonyl, (Ci -C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl;
  • R D 3 is hydrogen, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
  • R D 4 is halogen, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (Ci-C 4 ) alkoxy , Cyano, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl;
  • R D 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl, Phenyl or 3- to 6-membered heterocyclyl containing V D heteroatoms from the group consisting of nitrogen, oxygen and sulfur, the last seven radicals being represented by V D
  • R D 6 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C ' 6 ) alkynyl or (C 2 -C 6 ) alkynyl, the latter three radicals being substituted by V D radicals from the group halogen, hydroxy, ( Ci-C 4 ) alkyl, (Ci
  • R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical;
  • R D 7 is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen , (Ci-C4) alkoxy, (Ci- C 6) haloalkoxy and (Ci-C4) alkylthio and in case of cyclic radicals, also (Ci-C4) alkyl and
  • haloalkyl are substituted; n D is 0, 1 or 2; m D is 1 or 2;
  • V D is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example the following formula (S4 a ), which, for. B. are known from WO-A-97/45016
  • R D 7 (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen, (Ci-C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci C4) alkylthio and in the case of cyclic radicals also (Ci-C4) alkyl and (Ci-C4) haloalkyl are substituted; R d 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2;
  • VD is 0, 1, 2 or 3; such as
  • RD 8 and RD 9 independently of one another are hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-C6) alkenyl, (C 3 -C 6 ) alkynyl,
  • RD 4 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3 m D 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
  • R D 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; ni D 1 or 2;
  • R D 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl.
  • Carboxylic acid derivatives (S5) e.g.
  • R E 1 , R E 2 are independently halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkyl,
  • a E is COOR E 3 or COSR E 4 RE 3 , RE 4 are independently hydrogen, (Ci-C4) alkyl, (CF-GOalknyl,
  • RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, nitro, (Ci-C4) alkylthio, (Ci-C4) alkylsulfonyl, ( Ci-C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally
  • RF 2 hydrogen or (Ci-C4) alkyl RF 3 hydrogen, (Ci-CsjAlkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals unsubstituted or by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or their salts, preferably compounds in which XF CH, n F is an integer from 0 to 2,
  • RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy,
  • RF 2 hydrogen or (Ci-C4) alkyl
  • RF 3 hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals being unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted,
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • Y G , Z G independently of one another O or S, no an integer from 0 to 4,
  • RG 2 is (Ci-Ciejalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl, RG 3 is hydrogen or (C 1 -Cr,) alkyl.
  • Sl 1 Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
  • Cyometrinil or “CGA-43089” ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage to metolachlor.
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage by thiocarbamate herbicides
  • Fenclorim (4,6-dichloro-2-phenylpyrimidine) (S13-2) known as a safener for pretilachlor in sown rice
  • MG 191 (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • RH 1 denotes a (Ci-C 6 ) haloalkyl radical
  • RH 2 is hydrogen or halogen
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • RH 3 is (Ci-C4) alkoxy, (C2-C4) alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy and RH 4 is hydrogen or (Ci-C4) alkyl or
  • RH 3 and RH 4 together with the directly bound N atom have a four- to eight-membered structure
  • heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (Ci C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy and (Ci-C4) alkylthio is substituted.
  • Particularly preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1.1) to (1,137) and / or their salts are: mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichlormid and metcamifene.
  • herbicides or pesticides and safeners which contain the compounds of the general formula (1) or their combinations with other herbicides or pesticides and safeners.
  • the safeners which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
  • the weight ratio of herbicide (mixture) to safener generally depends on the
  • herbicide and the effectiveness of the respective safener can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of the general formula (1) or their mixtures with further herbicides / pesticides and as
  • the formulations present in the commercial form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, soil or
  • Scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the required application rate of the compounds of general formula (1) and their salts varies. It can fluctuate within wide limits, e.g. between 0.001 and 10.0 kg / ha or more
  • Active substance but preferably it is between 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha g / ha. This applies to both pre-emergence and post-emergence applications.
  • Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, especially for application to plants or Parts of plants or seeds, mixed or combined.
  • the carrier which can be solid or liquid, is generally inert and should be useful in agriculture.
  • Solid or liquid carriers are possible: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol , organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such
  • Carriers can also be used. Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
  • Liquids which can be used as liquefied gaseous extenders or carriers are those which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Aerosol propellants such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, can be used in the formulations.
  • Other additives can be mineral and vegetable oils.
  • organic solvents can also be used as auxiliary solvents.
  • auxiliary solvents e.g. organic solvents
  • aromatics such as xylene, toluene or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or dichloromethane
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils
  • Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water.
  • the agents according to the invention can additionally contain further constituents, e.g.
  • Suitable surface-active substances are emulsifiers and / or foam-generating agents, dispersants or wetting agents with ionic or nonionic
  • Naphthalenesulphonic acid polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurate derivatives), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignin sulfite waste liquors and methyl cellulose.
  • substituted phenols preferably alkylphenols or arylphenols
  • salts of sulphosuccinic acid esters preferably alkyl taurate derivatives
  • the presence of a surface-active substance is necessary if one of the active ingredients and / or one of the inert carriers is not soluble in water and if the application takes place in water.
  • the proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • protective colloids e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers,
  • the active ingredients can be combined with any solid or liquid additive that is commonly used for formulation purposes.
  • the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% Active ingredient, very particularly preferably between 10 and 70 percent by weight.
  • the active compounds or agents according to the invention as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the
  • the formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one conventional extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, if appropriate Drying agents and UV stabilizers and, if appropriate, dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids.
  • the compositions according to the invention include not only formulations which are already ready for use and can be applied to the plant or the seed using suitable apparatus, but also commercial concentrates which must be diluted with water before use.
  • the active compounds according to the invention can be used as such or in their (commercially available) formulations and in the use forms prepared from these formulations in a mixture with other (known) active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals are available.
  • active compounds such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals are available.
  • the treatment of the plants and parts of plants according to the invention with the active compounds or agents is carried out directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, (spraying) spraying, (spraying) spraying, sprinkling, evaporating, atomizing, atomizing, (scattering) scattering, foaming, brushing, spreading, watering (drenching), drip irrigation and with propagation material, in particular with seeds by dry pickling, wet pickling, slurry pickling, incrustation, single- or multi-layer coating, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself.
  • transgenic seeds with the active substances or agents according to the invention are of particular importance.
  • This relates to the seeds of plants which contain at least one heterologous gene which enables the expression of a polypeptide or protein with insecticidal properties.
  • the heterologous gene in transgenic seeds can e.g. from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • This heterologous gene preferably comes from Bacillus sp., The gene product having an action against the European corn borer (European comborer) and / or Western Com rootworm.
  • the heterologous gene particularly preferably comes from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment.
  • the seed can be treated at any time between harvesting and sowing.
  • seeds are used that have been separated from the plant and freed of pistons, shells, stems, husk, wool or pulp.
  • seeds can be used that have been harvested, cleaned and dried to a moisture content of less than 15% by weight.
  • seeds can be used that have been treated with water after drying and then dried again.
  • care must be taken that the amount of the agent and / or other additives according to the invention applied to the seed is selected so that the germination of the seed is not impaired or the resulting plant is not damaged. This is particularly important for active substances that can show phytotoxic effects at certain application rates.
  • the agents according to the invention can be applied directly, that is, without further ones
  • Suitable formulations and methods for seed treatment are known to the person skilled in the art and are e.g. described in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
  • the active compounds according to the invention can be converted into the customary mordant formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
  • customary mordant formulations such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or
  • Diluents dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Suitable dyes which can be contained in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which can be contained in the mordant formulations which can be used according to the invention are all substances which promote wetting and are customary for the formulation of agrochemical active ingredients.
  • Alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
  • the dispersants and / or emulsifiers which can be contained in the mordant formulations which can be used according to the invention are all used to formulate agrochemicals
  • Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used.
  • Suitable nonionic dispersants are especially ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates.
  • the mordant formulations which can be used according to the invention can contain, as defoamers, all of the foam-inhibiting substances which are customary for the formulation of agrochemical active compounds. Silicone defoamers and magnesium stearate can preferably be used.
  • All substances which can be used for such purposes in agrochemical compositions can be present as preservatives in the mordant formulations which can be used according to the invention.
  • Examples include dichlorophene and benzyl alcohol hemiform.
  • Secondary thickeners which can be contained in the mordant formulations which can be used according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
  • Suitable adhesives which can be contained in the mordant formulations which can be used according to the invention are all binders customarily used in mordants.
  • Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
  • mordant formulations which can be used according to the invention can be used either directly or after prior dilution with water for treating a wide variety of seeds, including seeds of transgenic plants. In cooperation with the substances formed by expression, additional synergistic effects can also occur.
  • the dressing is carried out by placing the seeds in a mixer which Add the desired amount of seed dressing formulations either as such or after prior dilution with water and mix until the formulation is evenly distributed on the seed. If necessary, a drying process follows.
  • the active compounds according to the invention are more suitable if they are well tolerated by plants
  • plants which can be treated according to the invention maize, soybean, cotton, Brassica oilseeds such as Brassica napus (for example Canola), Brassica rapa, B. juncea (for example (field) mustard) and Brassica carinata, rice, Wheat sugar beet, sugar cane,
  • Rosaceae sp. for example pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries
  • Rosaceae sp. for example pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries
  • Ribesioidae sp. Juglandaceae sp.
  • Betulaceae sp. Anacardiaceae sp.
  • Fagaceae sp. Moraceae sp.
  • Oleaceae sp. Actinidaceae sp.
  • Lauraceae sp. Musaceae sp.
  • Rubiaceae sp. e.g. coffee
  • Theaceae sp. Sterculiceae sp.
  • Rutaceae sp. e.g. lemons, organs and grapefruit
  • Solanaceae sp. for example tomatoes, potatoes, pepper, eggplants
  • Liliaceae sp. Compositae sp.
  • lettuce, artichoke and chicory including root chicory, endive or common chicory
  • Umbelliferae sp. e.g. carrot, parsley, celery and tuber celery
  • Cucurbitaceae sp. for example cucumber - including pickled cucumber, pumpkin, watermelon, bottle gourd and melons
  • Alliaceae sp. for example leek and onion
  • Leguminosae sp. e.g. peanuts, peas, and beans - such as runner bean and field bean
  • Chenopodiaceae sp. for example Swiss chard, beet, spinach, beet
  • Malvaceae for example okra
  • Asparagaceae for example asparagus
  • all plants and their parts can be treated.
  • wild plant species and plant cultivars and their parts obtained by conventional organic breeding methods, such as hybridization or protoplast fusion are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated.
  • the term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new ones
  • the treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), e.g. B. plants or seeds can be used.
  • GMOs genetically modified organisms
  • Genetically modified plants are plants in which a heterologous gene has been stably integrated into the genome.
  • heterologous gene essentially means a gene which is provided or assembled outside the plant and which, when introduced into the cell nucleus genome, the
  • Chloropiastene genome or the mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down-regulating or genes in the plant or genes in the plant switches off (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA interference]).
  • a heterologous gene that is present in the genome is also called a transgene.
  • a transgene that is defined by its specific presence in the plant genome is called a transformation or transgenic event.
  • Treatment conditions according to the invention can also lead to superadditive ("synergistic") effects in growth conditions (soils, climate, growing season, nutrition).
  • superadditive additive
  • the following effects are possible that go beyond the effects that are actually to be expected: reduced application rates and / or expanded spectrum of activity and / or increased effectiveness of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to
  • Dryness or water or soil salt content increased flowering performance, easier harvesting,
  • Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful traits (regardless of whether this was achieved by breeding and / or biotechnology).
  • nematode-resistant plants are described, for example, in the following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 11 / 657,964, 12 / 192,904, 11 / 396.808, 12 / 166.253, 12 / 166.239, 12 / 166.124, 12 / 166.209, 11 / 762.886, 12 / 364.335, 11 / 763.947, 12 / 252.453, 12 / 209.354, 12 / 491.396 and 12 / 497.221. Plants that can be treated according to the invention are hybrid plants that already have the
  • Such plants are typically created by crossing one inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another inbred male-sterile parent line (the female crossing partner) with another
  • hybrid seeds are typically harvested from the male-sterile plants and sold to propagators.
  • Pollen-sterile plants can sometimes (e.g. in maize) be produced by detasseling (i.e. mechanically removing the male genital organs or the male flowers); however, it is more common for pollen sterility to be based on genetic determinants in the plant genome. In this case, especially when the desired product is seeds because one wants to harvest from the hybrid plants, it is usually beneficial to ensure that pollen fertility in hybrid plants contains the genetic determinants responsible for pollen sterility , is completely restored.
  • Genetic determinants for male sterility can be localized in the cytoplasm. Examples of cytoplasmic pollen sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants for male sterility can also be localized in the cell core genome. Pollen-sterile plants can also be obtained using methods of plant biotechnology, such as genetic engineering.
  • a ribonuclease such as a bamase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored in the tapetum cells by expression of a ribonuclease inhibitor such as Barstar.
  • Plants or plant cultivars which are obtained using methods of plant biotechnology, such as genetic engineering which can be treated according to the invention are herbicide-tolerant plants, i.e. H. Plants that have been made tolerant to one or more specified herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation that confers such herbicide tolerance.
  • Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants which have been made tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant of glyphosate using various methods. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp.
  • EPSPS 5-enolpyruvylshikimate-3-phosphate synthase
  • EPSPS EPSPS from the petunia (Shah et al., 1986, Science 233, 478-481) for an EPSPS code from the tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704). It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme.
  • Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants that contain naturally occurring mutations in the above-mentioned genes. Plants that express EPSPS genes that confer glyphosate tolerance are described. Plants which have other genes which confer glyphosate tolerance, for example decarboxylase genes, have been described.
  • herbicide-resistant plants are, for example, plants which have been made tolerant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition.
  • an effective detoxifying enzyme is, for example, an enzyme that is used for a
  • phosphinotricin acetyltransferase such as the bar or pat protein from Streptomyces species. Plants that express an exogenous phosphinotricin acetyltransferase have been described.
  • Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogenate.
  • Plants that are tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutated or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044.
  • Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes that code for certain enzymes that enable the formation of homogenate despite the inhibition of the native HPPD enzyme by the HPPD inhibitor.
  • plants are described in WO 99/34008 and WO 02/36787.
  • the tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described.
  • plants can be made more tolerant of HPPD inhibitors by using inserts a gene into their genome which codes for an enzyme which metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).
  • ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
  • Acetohydroxy acid synthase (AHAS, known) impart tolerance to different herbicides or groups of herbicides, such as in Tranel and Wright (Weed Science 2002, 50, 700 - 712).
  • AHAS Acetohydroxy acid synthase
  • imidazo linon-tolerant plants is described.
  • Other sulfonylurea and imidazo linone tolerant plants are also described.
  • Further plants which are tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf. for example for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such stress resistance. Particularly useful plants with stress tolerance include the following:
  • Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.
  • PARP poly (ADP-ribose) polymerase
  • Plants that contain a stress-tolerant transgene that encodes a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamidinamide transidiboribinotinosinodidase niborotinosinodinase diborobenzylase.
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a changed amount, quality and / or storability of the edged product and / or changed properties of certain constituents of the edged product, such as: 1) Transgenic plants that synthesize a modified starch, the chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the
  • Viscosity behavior, the gel strength, the starch size and / or starch comorphology is changed compared to the synthesized starch in wild type plant cells or plants, so that this modified starch is more suitable for certain applications.
  • Non-starch carbohydrate polymers the properties of which have changed in comparison to wild type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,4-branched alpha-1,4-glucans and plants which Produce Alteman.
  • Transgenic plants or hybrid plants such as onions with certain properties such as "high soluble solids content” (“high soluble solids content”), low sharpness (“low pungency”, LP) and / or long shelf life (“long storage", LS ).
  • Plants or plant varieties which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as
  • Cotton plants with changed fiber properties Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such modified fiber properties; these include:
  • Plants such as cotton plants which contain a modified form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants with an increased expression of sucrose phosphate synthase;
  • plants such as cotton plants with an increased expression of sucrose synthase
  • Plants such as cotton plants in which the timing of the passage control of the plasmodesms at the base of the fiber cell is changed, e.g. B. by down-regulating the fiber-selective ⁇ -1,3-glucanase; e) Plants such as cotton plants with fibers with changed reactivity, e.g. B. by expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes.
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with changed properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which imparts such altered oil properties; these include:
  • Plants such as oilseed rape plants that produce oil with a high oleic acid content
  • Plants such as rapeseed plants that produce oil with a low linolenic acid content.
  • Plants such as oilseed rape plants that produce oil with a low saturated fatty acid content.
  • Plants or plant varieties which can be obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, carry II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
  • viruses which are virus-resistant, e.g. against the potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced cold-induced sweetness (which
  • Plants or plant cultivars which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties in seed loss (seed shattering). Such plants can be genetically transformed or selected from plants containing a mutation that confer such altered properties and include plants such as oilseed rape with delayed or reduced seed loss.
  • transgenic plants which can be treated according to the invention are plants with transformation events or combinations of transformation events which have been issued or pending petitions by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the unregulated status. Information on this is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http://www.aphis.usda.gov/brs/not_reg.html. On the filing date of this
  • Transgenic phenotype the trait that is given to the plant by the transformation event.
  • transgenic plants which can be treated according to the invention are plants with one or more genes which code for one or more toxins, are the transgenic plants which are offered under the following trade names: YIELD GARD® (for example corn, cotton, Soybeans), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (e.g.
  • Herbicide-tolerant plants to be mentioned are, for example, maize varieties, cotton varieties and soybean varieties, which are offered under the following trade names: Roundup Ready® (glyphosate tolerance, for example maize, cotton, soybean), Liberty Link® (phosphinotricine tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (Sylfonylurstoffioleranz), for example maize.
  • the herbicide-resistant plants (plants bred traditionally to herbicide tolerance) that should be mentioned include the varieties offered under the name Clearfield® (for example maize).
  • transgenic plants which can be treated according to the invention are plants which contain transformation events or a combination of transformation events and which are listed, for example, in the files of various national or regional authorities (see, for example, http: / /gmoinfo.jrc.it/gmp_browse.aspx and

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Abstract

The invention relates to substituted heterocyclic pyrrolones of general formula (I) or salts thereof, wherein the groups in general formula (I) are as defined in the description, and to the use thereof as herbicides, in particular for controlling weeds and/or weed grasses in crops of cultivated plants and/or as plant-growth regulators for influencing the growth of crops of cultivated plants.

Description

Bayer AG  Bayer AG
Substituierte Heterocyclylpyrrolone sowie deren Salze und ihre Verwendung als herbizide Wirkstoffe Beschreibung Substituted heterocyclylpyrrolones and their salts and their use as herbicidal active ingredients Description
Die Erfindung betrifft das technische Gebiet der Pflanzenschutzmittel, insbesondere das der Herbizide zur selektiven Bekämpfung von Unkräutern und Ungräsem in Nutzpflanzenkulturen. The invention relates to the technical field of crop protection agents, in particular that of herbicides for the selective control of weeds and weeds in crops of useful plants.
Speziell betrifft diese Erfindung substituierte Heterocyclylpyrrolone sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. In particular, this invention relates to substituted heterocyclylpyrrolones and their salts, processes for their preparation and their use as herbicides.
Bisher bekannte Pflanzenschutzmittel zur selektiven Bekämpfung von Schadpflanzen in Known crop protection products for the selective control of harmful plants in
Nutzpflanzenkulturen oder Wirkstoffe zur Bekämpfung von unerwünschtem Pflanzenwuchs weisen bei ihrer Anwendung teilweise Nachteile auf, sei es, dass sie (a) keine oder aber eine unzureichende herbizide Wirkung gegen bestimmte Schadpflanzen, (b) ein zu geringes Spektrum der Schadpflanzen, das mit einem Wirkstoff bekämpft werden kann, (c) zu geringe Selektivität in Nutzpflanzenkulturen und/oder (d) ein toxikologisch ungünstiges Profil besitzen. Weiterhin führen manche Wirkstoffe, die als Pflanzenwachstumsregulatoren bei einigen Nutzpflanzen eingesetzt werden können, bei anderen Nutzpflanzen zu unerwünscht verminderten Emteerträgen oder sind mit der Kulturpflanze nicht oder nur in einem engen Aufwandmengenbereich verträglich. Einige der bekannten Wirkstoffe lassen sich wegen schwer zugänglicher Vorprodukte und Reagenzien im industriellen Maßstab nicht wirtschaftlich hersteilen oder besitzen nur unzureichende chemische Stabilitäten. Bei anderen Wirkstoffen hängt die Wirkung zu stark von Umweltbedingungen, wie Wetter- und Bodenverhältnissen ab. Crop crops or active ingredients to combat undesirable plant growth sometimes have disadvantages when used, either because they (a) have no or an inadequate herbicidal activity against certain harmful plants, (b) the spectrum of the harmful plants is too small to combat with an active ingredient can be (c) insufficient selectivity in crops and / or (d) have a toxicologically unfavorable profile. Furthermore, some active ingredients which can be used as plant growth regulators in some crop plants lead to undesirably reduced crop yields in other crop plants or are incompatible or only compatible with the crop plant in a narrow range of application rates. Some of the known active ingredients cannot be economically manufactured on an industrial scale because of precursors and reagents that are difficult to access, or they have insufficient chemical stabilities. For other active substances, the effect depends too much on environmental conditions such as weather and soil conditions.
Die herbizide Wirkung dieser bekannten Verbindungen, insbesondere bei niedrigen Aufwandmengen, bzw. deren Verträglichkeit gegenüber Kulturpflanzen bleiben verbesserungswürdig.  The herbicidal activity of these known compounds, especially at low application rates, or their compatibility with crop plants remains in need of improvement.
Aus den genannten Gründen besteht weiterhin ein Bedarf nach wirkungsstarken Herbiziden und/oder Pflanzenwachstumsregulatoren für die selektive Anwendung in Pflanzenkulturen oder die Anwendung auf Nichtkulturland, wobei diese Wirkstoffe vorzugsweise weitere vorteilhafte Eigenschaften in der Anwendung haben sollten, wie zum Beispiel eine verbesserte Verträglichkeit gegenüber Kulturpflanzen. Ein Gegenstand der vorliegenden Erfindung ist daher die Bereitstellung von Verbindungen mit herbizider Wirkung (Herbizide), die bereits bei relativ niedrigen Aufwandmengen gegen wirtschaftlich wichtige Schadpflanzen hochwirksam sind und vorzugsweise bei guter Wirksamkeit gegen For the reasons mentioned, there is still a need for potent herbicides and / or plant growth regulators for selective use in plant crops or for use in nonculture land, these active compounds preferably having other advantageous properties in use, such as, for example, improved tolerance to crop plants. One object of the present invention is therefore to provide compounds with herbicidal activity (herbicides) which are highly effective against economically important harmful plants even at relatively low application rates and preferably against good activity
Schadpflanzen selektiv in Kulturpflanzen eingesetzt werden können und dabei vorzugsweise eine gute Verträglichkeit gegenüber Kulturpflanzen zeigen. Bevorzugt sollten diese herbiziden Verbindungen insbesondere effektiv und effizient gegen ein breites Spektrum an Ungräsem sein, und vorzugsweise zusätzlich eine gute Wirksamkeit gegen viele Unkräuter aufweisen. Harmful plants can be used selectively in crop plants and preferably show good tolerance to crop plants. Preferably, these herbicidal compounds should, in particular, be effective and efficient against a wide range of grasses, and preferably also have good effectiveness against many weeds.
Verschiedene Schriften beschreiben substituierte Pyrrolone und Hydantoine mit herbiziden Various publications describe substituted pyrrolones and hydantoins with herbicides
Eigenschaften. Aus WO2016/071359 und W02016/071360 sind Pyrrolone bekannt, die am Stickstoff heterocyclische Substituenten tragen, beispielsweise auch gegebenenfalls weiter substituierte lsoxazoline. Weiterhin sind substituierte Pyrrolone und ihre herbiziden oder pestiziden Eigenschaften in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 und EP0286816 beschrieben ln WO2016/071361, WO2016/071362, WO2016/071363 und WO2016/071364 werden weiterhin substituierte Hydantoine beschrieben, die am Stickstoff ebenfalls heterocyclische Substituenten tragen, beispielsweise gegebenenfalls weiter substituierte lsoxazoline. Ausgewählte speziell substituierte 1,3,4- Thiadiazolyl- und l,2,4-Thiadiazolyl-2,5-Dioxoimidazoline und ihre herbizide Wirkung werden in DE2247266 beschrieben. Substituierte Pyrazolylpyrrolone und ihre Verwendung als herbizide Characteristics. From WO2016 / 071359 and W02016 / 071360 pyrrolones are known which carry heterocyclic substituents on the nitrogen, for example also optionally further substituted isoxazolines. Substituted pyrrolones and their herbicidal or pesticidal properties are also described in CH633678, DE 2735841, EP0297378, EP0334133, EP0339390 and EP0286816 carry heterocyclic substituents, for example optionally further substituted isoxazolines. Selected specially substituted 1,3,4-thiadiazolyl- and 1,2,4-thiadiazolyl-2,5-dioxoimidazolines and their herbicidal activity are described in DE2247266. Substituted pyrazolylpyrrolones and their use as herbicides
Wirkstoffe werden beispielsweise in WO2015/018434 beschrieben. Active ingredients are described, for example, in WO2015 / 018434.
Es ist weiterhin bekannt, daß bestimmte substituierte Carbamoyloxypyrrolone und Phenyloxypyrrolone als Wuchsregulatoren oder Keimungsstimulatoren eingesetzt werden können (vgl. WO2014/131843 und WO2015/128321). Das Strukturmotiv der Hydroxypyrrolone findet sich auch in Substanzen, die aus Lilium candidum isoliert wurden, z. B. l,5-Dihydro-5-hydroxy-3,4‘-dimethyl-[l,2‘-bi-2H-pyrrolo]- 2,5‘(l’H)-dion (vgl. Ceska a Slovenska Farmacie, 2007, 56, 27; Neoplasma, 2000, 47, 313). It is also known that certain substituted carbamoyloxypyrrolones and phenyloxypyrrolones can be used as growth regulators or germination stimulators (cf. WO2014 / 131843 and WO2015 / 128321). The structural motif of hydroxypyrrolone is also found in substances isolated from Lilium candidum, e.g. B. 1,5-Dihydro-5-hydroxy-3,4'-dimethyl- [1,2'-bi-2H-pyrrolo] - 2,5 '(l'H) -dione (cf. Ceska a Slovenska Farmacie , 2007, 56, 27; Neoplasma, 2000, 47, 313).
Die Verwendung von substituierten Heterocyclylpyrrolonen oder deren Salze als herbizide Wirkstoffe ist dagegen noch nicht beschrieben. Überraschenderweise wurde nun gefunden, dass die nachfolgenden Verbindungen der allgemeinen Formel (1) und deren Salze eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen aufweisen. However, the use of substituted heterocyclylpyrrolones or their salts as herbicidal active ingredients has not yet been described. Surprisingly, it has now been found that the following compounds of the general formula (1) and their salts have excellent herbicidal activity against a broad spectrum of economically important mono- and dicotyledonous harmful plants.
Gegenstand der vorliegenden Erfindung sind daher Verbindungen der allgemeinen Formel (1) The present invention therefore relates to compounds of the general formula (1)
Figure imgf000003_0001
Figure imgf000003_0001
worin wherein
Q für die Gruppe
Figure imgf000004_0001
steht, Q for the group
Figure imgf000004_0001
stands,
A unabhängig voneinander für O (Sauerstoff), S (Schwefel) oder die Gruppierung NR10 oder C-A independently of one another for O (oxygen), S (sulfur) or the grouping NR 10 or C-
RUR12 stehen, wobei R10, R1 1 und R12 in den Gruppierungen NR10 oder C-RUR12 jeweils gleiche oder verschiedene Bedeutungen gemäß der unten stehenden Definition haben, R U R 12 , where R 10 , R 1 1 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below,
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Halogen, Cyano, (Ci-Cg)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-Cg)-Hydroxyalkyl, ( C i - C s ) -R 1 for halogen, cyano, (Ci-Cg) alkyl, (Ci-C8) haloalkyl, (Ci-Cg) hydroxyalkyl, (C i - C s) -
Alkoxyalkyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, Aryl, Heteroaryl, Aryloxy, Heteroaryloxy, Heterocyclyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkenyloxy, (C2-C8)-Alkinyl steht, Alkoxyalkyl, (Ci-Cg) alkoxy, (Ci-Cg) haloalkoxy, (Ci-C8) alkylthio, (Ci-C8) haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C 3 -Cio) -Cycloalkyl, (C 3 -C 10 ) -cycloalkyl- (Ci-C8) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 8 ) -alkyl, (Ci-C8) alkylcarbonyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkenyloxy, (C 2 -C 8 ) alkynyl,
R2 für Hydroxy, Hydrothio, Halogen, NR13R14, (Ci-Cg)-Alkoxy, (C3-Cio)-Cycloalkyl-(Ci-C8)- alkoxy, Aryl-(Ci-Cg)-alkoxy, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy, Arylcarbonyloxy, (Ci-Cs)- Alkylcarbonyloxy, Aryl-(Ci-C8)-alkylcarbonyloxy, Heteroarylcarbonyloxy, (C3-C10)- Cycloalkylcarbonyloxy, Heterocyclylcarbonyloxy, (Ci-C8)-Haloalkyl-carbonyloxy, (C2-C8)- Alkenylcarbonyloxy, OC(0)OR15, OC(0)SR16, OC(S)OR15, OC(S)SR16, OSO2R16, OSO2OR15, OCHO, 0C(0)NR13R14 steht, R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-Cg) alkoxy, (C3-Cio) cycloalkyl- (Ci-C8) alkoxy, aryl- (Ci-Cg) -alkoxy, (Ci -C8) alkoxy- (Ci-C8) alkoxy, arylcarbonyloxy, (Ci-Cs) - alkylcarbonyloxy, aryl- (Ci-C8) alkylcarbonyloxy, heteroarylcarbonyloxy, (C 3 -C 10 ) - cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci -C8) haloalkylcarbonyloxy, (C 2 -C 8 ) alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , OSO 2 R 16 , OSO 2 OR 15 , OCHO, 0C (0) NR 13 R 14 ,
R3 für Wasserstoff, (Ci-Cg)-Alkyl steht, R 3 represents hydrogen, (Ci-Cg) alkyl,
R4, R5, R6, R7,R8 und R9 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C8)-Alkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)- alkyl, (Ci-Csj-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cg)-alkyl, Heteroaryl-(Ci-Cg)- alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C2-Cg)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Alkoxycarbonyl- (Ci-Cs)-alkyl, (Ci-C8)-Alkoxy-(Ci-Cs)-alkyl, Arylcarbonyloxy-(Ci-C8)-alkyl, Heteroarylcarbonyloxy-(Ci-Cg)-alkyl, Heterocyclylcarbonyloxy-(Ci-Cg)-alkyl, (Ci-Cs)- Alkylcarbonyloxy-(Ci-Cg)-alkyl, (C3-Cg)-Cycloalkylcarbonyloxy-(Ci-Cg)-alkyl, C(0)0R15, C(0)NR13R14, SR16, SOR16, S02R16, NR13R14, Cyano stehen, oder wobei R4, R5, R6, R7,R8 und R9 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen gesättigten oder teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7- gliedrigen Ring bilden, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C8) -alkyl, (Ci-C 8 ) -hydroxyalkyl, (Ci-C 8 ) - Haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8 ) - alkyl, (Ci-Csj-alkoxy, aryl, heteroaryl, heterocyclyl, aryl- (Ci-Cg) - alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-C8) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C8) -alkoxycarbonyl- (Ci-Cs) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-Cs) -alkyl, arylcarbonyloxy- (Ci-C 8 ) -alkyl, heteroarylcarbonyloxy- (Ci-Cg) -alkyl, heterocyclylcarbonyloxy- (Ci -Cg) alkyl, (Ci-Cs) alkylcarbonyloxy (Ci-Cg) alkyl, (C3-Cg) cycloalkylcarbonyloxy (Ci-Cg) alkyl, C (0) 0R 15 , C (0) NR 13 R 14 , SR 16 , SOR 16 , S0 2 R 16 , NR 13 R 14 , cyano, or where R 4 , R 5 , R 6 , R 7 , R 8 and R 9 together with the carbon atom that they are each bound, form a saturated or partially saturated ring, which is optionally interrupted by one to three heteroatoms from the group N, O and S and is optionally further substituted and has a total of 3-7-membered ring,
R10 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl- (Ci-Cg)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cg)-alkyl, Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-Cg)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (C2-Cg)-Haloalkenyl, (C2-Cg)- Haloalkinyl, (C4-Cio)-Cycloalkenyl, Aryl-(C2-Cg)-alkenyl, Heteroaryl-(C2-Cg)-alkenyl, R 10 is hydrogen, (Ci-Cg) -alkyl, (Ci-Cg) -haloalkyl, (C 3 -Cio) -cycloalkyl, (C3-C10) - cycloalkyl- (Ci-Cg) -alkyl, aryl, heteroaryl, Heterocyclyl, aryl- (Ci-Cg) -alkyl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C 2 -Cg) -alkenyl, (C 2 -Cg) -alkynyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (C4-Cio) cycloalkenyl, aryl- (C 2 -Cg) alkenyl, heteroaryl- (C 2 -Cg) alkenyl,
Heterocyclyl-(C2-Cg)-alkenyl, Arylcarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl-(Ci-Cg)-alkyl, Heteroarylcarbonyl-(Ci-Cg)-alkyl, (C3-Cio)-Cycloalkylcarbonyl-(Ci-Cg)-alkyl, Aryl-(Ci-Cs)- alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Csj-Alkoxy^Ci-Cs)- alkyl, (Ci-Cg)-Haloalkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl, S02R16, CHO, C(0)OR15, R13R14N-(Ci-Cg)-alkyl oder Cyano-(Ci-Cg)-alkyl steht, Heterocyclyl- (C 2 -Cg) alkenyl, arylcarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl- (Ci-Cg) -alkyl, heteroarylcarbonyl- (Ci-Cg) -alkyl, (C3- Cio) -cycloalkylcarbonyl- (Ci-Cg) -alkyl, aryl- (Ci-Cs) -alkoxycarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkoxycarbonyl- (Ci-Cg) -alkyl, (Ci Csj-alkoxy ^ Ci-Cs) -alkyl, (Ci-Cg) -haloalkoxy- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, S0 2 R 16 , CHO, C (0) OR 15 , R 13 R 14 is N- (Ci-Cg) -alkyl or cyano- (Ci-Cg) -alkyl,
R11 und R12 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci -Cs)- Alkyl, (Ci-Cs)- Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-Cs)-alkyl, (Ci-Cs)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cs)-alkyl, Heteroaryl-(Ci-Cs)-alkyl, Heterocyclyl-(Ci-Cs)- alkyl, (C2-Cs)-Alkenyl, (C2-Cs)-Alkinyl, (Ci-C8)-Alkoxycarbonyl-(Ci-Cs)-alkyl, (Ci-Cs)- Alkoxy-(Ci-Cs)-alkyl, Arylcarbonyloxy-(Ci-Cs)-alkyl, Heteroarylcarbonyloxy-(Ci-Cs)-alkyl, Heterocyclylcarbonyloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyloxy-(Ci-C8)-alkyl, (C3-Cs)- Cycloalkylcarbonyloxy-(Ci-C8)-alkyl, C(0)OR15, C(0)NR13R14, SR16, SOR16, S02R16, NR13R14, Cyano stehen, oder wobei R11 und R12 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7-gliedrigen Ring bilden, R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-Cs) - alkyl, (Ci-Cs) - haloalkyl, (C3-Cio) -cycloalkyl, (C3-Cio) -cycloalkyl- (Ci-Cs ) alkyl, (Ci-Cs) alkoxy, aryl, heteroaryl, heterocyclyl, aryl (Ci-Cs) alkyl, heteroaryl (Ci-Cs) alkyl, heterocyclyl (Ci-Cs) alkyl, (C 2 -Cs) alkenyl, (C 2 -Cs) alkynyl, (Ci-C 8 ) alkoxycarbonyl- (Ci-Cs) alkyl, (Ci-Cs) - alkoxy- (Ci-Cs) alkyl, arylcarbonyloxy - (Ci-Cs) -alkyl, heteroarylcarbonyloxy- (Ci-Cs) -alkyl, heterocyclylcarbonyloxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkylcarbonyloxy- (Ci-C 8 ) -alkyl, (C3 -Cs) - cycloalkylcarbonyloxy- (Ci-C 8 ) alkyl, C (0) OR 15 , C (0) NR 13 R 14 , SR 16 , SOR 16 , S0 2 R 16 , NR 13 R 14 , cyano, or wherein R 11 and R 12 together with the carbon atom to which they are each bound form a partially saturated, in total 3-7-membered, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted Forming a ring,
R13 und R14 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cs)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-C8)-Cycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci- Cg)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C8)-Cycloalkenyl-(Ci-C8)-alkyl, S02R16, Heterocyclyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl, Heteroaryl-(Ci-C8)- Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl oder Heterocyclyl- (Ci-C8)-alkyl stehen, R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cs) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (Ci-C 8 ) - Cyanoalkyl, (Ci-C 8 ) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -C 8 ) cycloalkenyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkoxy- (Ci-C 8 ) -alkyl, (Ci-C8) -alkylthio- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkylthio- (Ci- Cg) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, ( C 3 -Cio) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -C 8 ) -cycloalkenyl- (Ci-C 8 ) -alkyl, S0 2 R 16 , heterocyclyl, (Ci-C 8 ) - Alkoxycarbonyl- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxycarbonyl, aryl- (Ci-C 8 ) -alkoxycarbonyl- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkoxycarbonyl , Heteroaryl- (Ci-C 8 ) -alkoxycarbonyl, (C2-C8) -alkenyloxycarbonyl, (C2-C8) -alkynyloxycarbonyl or heterocyclyl- (Ci-C 8 ) -alkyl,
R15 für (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkmyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Haloalkyl,R 15 represents (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C2-C 8 ) -alkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -haloalkyl,
(C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-Cio)-Cycloalkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)- alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)-Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl- (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl oder Heterocyclyl-(Ci-C8)-alkyl steht, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -Cio) cycloalkenyl, (Ci-C 8 ) alkoxy- (Ci C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, (C 3 -Cio) cycloalkyl- (Ci-C 8 ) alkyl, (C 4 -Cio) cycloalkenyl- (Ci-C 8 ) alkyl, (Ci-C 8 ) alkoxycarbonyl- (Ci-C 8 ) alkyl, (C2-C8) alkenyloxycarbonyl- (Ci-C8) alkyl, aryl- (Ci-C 8 ) -alkoxycarbonyl- (Ci-C 8 ) -alkyl, hydroxycarbonyl- (Ci-C 8 ) -alkyl , Heterocyclyl or heterocyclyl- (Ci-C 8 ) -alkyl,
R16 für (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkmyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-Cio)-Cycloalkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C4- Cio)-Cycloalkenyl-(Ci-C8)-alkyl steht, und wobei die cyclischen Strukturelemente, insbesondere die Strukturelemente Aryl, Cycloalkyl, Cycloalkenyl, Heteroaryl und Heterocyclyl, der jeweils in R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 R13, R14, R15 und R16 genannten Reste unsubstituiert sind oder durch einen oder mehrere Reste, ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Hydroxy, Cyano, NR13R14, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)-Alkylthio, (Ci-C4)-Alkylsulfoxy, (Ci- C4)-Alkylsulfon, (Ci-C4)-Haloalkylthio, (Ci-C4)-Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)- Alkoxy-carbonyl, (Ci-C4)-Haloalkoxy-carbonyl, (Ci-C4)-Alkylcarboxy, (C3-C6)-Cycloalkyl, (C3-CÖ)- Cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)-Alkoxy-carbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl, Hydroxycarbonyl- (Ci-C4)-alkyl, R13R14N-carbonyl, und wobei die Strukturelemente Cycloalkyl bzw. Heterocyclyl n Oxogruppen aufweisen, wobei n = 0, 1 oder 2 ist, substituiert sind. R 16 is for (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C2-C 8 ) alkyl, (Ci-C 8 ) cyanoalkyl, (Ci-Cio) haloalkyl, (C 2 -C 8 ) haloalkenyl, (C 2 -C 8 ) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -Cio) cycloalkenyl, (Ci-C 8 ) alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -Cio) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -Cio) -cycloalkenyl- (Ci-C 8 ) -alkyl, and wherein the cyclic Structural elements, in particular the structural elements aryl, cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl, each of which is in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 R 13 , R 14 , R 15 and R 16 are unsubstituted or by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR 13 R 14 , (Ci-C 4 ) -Alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C 4 ) -alkylsulfoxy, (Ci- C4) alkylsulfone, (Ci-C4) haloalkylthio, (Ci-C 4) -Haloalkylsulfoxy, (Ci-C 4) -Haloalkylsulfon, (Ci-C 4) - alkoxy-carbonyl, (Ci- C 4 ) -Haloalkoxy-carbonyl, (Ci-C 4 ) -alkylcarboxy, (C 3 -C 6 ) -cycloalkyl, (C 3 -C Ö ) -cycloalkyl- (Ci-C 6 ) -alkyl, (Ci-C 4 ) -alkoxy-carbonyl- (Ci-C 4 ) -alkyl, hydroxycarbonyl, hydroxycarbonyl- (Ci-C 4 ) -alkyl, R 13 R 14 N-carbonyl, and wherein the structural elements have cycloalkyl or heterocyclyl n oxo groups, where n = 0, 1 or 2, are substituted.
Die Verbindungen der allgemeinen Formel (1) können Salze bilden. Salzbildung kann durch Einwirkung einer Base auf solche Verbindungen der allgemeinen Formel (1) erfolgen, die ein acides The compounds of the general formula (1) can form salts. Salt formation can take place by the action of a base on those compounds of the general formula (1) which are acidic
Wasserstoffatom tragen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Wear hydrogen atom. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali or
Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder Alkaline earth metal hydroxides, carbonates and bicarbonates, especially sodium and Potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR'R' 'R ' ' ']+, worin R bis R' " jeweils unabhängig voneinander einen organischen Rest, Alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR ' R '' R ''' ] + +, where R to R '"are each independent an organic residue from each other,
insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (Ci-C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. in particular represent alkyl, aryl, aralkyl or alkylaryl. Alkyl sulfonium and alkyl sulfoxonium salts, such as (Ci-C 4 ) -trialkyl sulfonium and (Ci-C 4 ) -trialkyl sulfoxonium salts are also suitable.
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten The compounds of the general formula (I) can be added by adding a suitable
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, H3PO4 oder HNO3, oder organische Säuren, z. B. Carbonsäuren, wie Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p- Toluolsulfonsäure, an eine basische Gruppe, wie z.B. Amino, Alkylamino, Dialkylamino, Piperidino, Morpholino oder Pyridino, Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion. inorganic or organic acid, such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4 or HNO 3 , or organic acids, e.g. B. carboxylic acids, such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids, such as p-toluenesulfonic acid, to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts. These salts then contain the conjugate base of the acid as an anion.
Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren oder Carbonsäuren, vorhegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Suitable substituents which are in deprotonated form, e.g. Sulphonic acids or carboxylic acids can exist, internal salts with protonatable groups such as amino groups.
Die erfindungsgemäßen substituierten Heteroarylpyrrolone der allgemeinen Formel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH-Wert, Lösungsmittel und Temperatur in verschiedenen tautomeren Strukturen vorhegen, die alle von der allgemeinen Formel (I) umfasst sein sollen. The substituted heteroarylpyrrolones of the general formula (I) according to the invention can, depending on external conditions, such as pH, solvent and temperature, be present in various tautomeric structures, all of which are intended to be encompassed by the general formula (I).
Ist eine Gruppe mehrfach durch Reste substituiert, so bedeutet dies, dass diese Gruppe durch einen oder mehrere gleiche oder verschiedene der genannten Reste substituiert ist. If a group is substituted several times by radicals, this means that this group is substituted by one or more identical or different of the radicals mentioned.
In allen nachfolgend genannten Formeln haben die Substituenten und Symbole, sofern nicht anders definiert, dieselbe Bedeutung wie unter der allgemeinen Formel (I) beschrieben. Pfeile in einer chemischen Formel bedeuten die Verknüpfungsorte zum restlichen Molekül. In all of the formulas mentioned below, unless otherwise defined, the substituents and symbols have the same meaning as described under the general formula (I). Arrows in a chemical formula indicate the points of connection to the rest of the molecule.
Im Folgenden werden, jeweils für die einzelnen Substituenten, bevorzugte, besonders bevorzugte, ganz besonders bevorzugte und im Speziellen bevorzugte Bedeutungen beschrieben. Die übrigen Preferred, particularly preferred, very particularly preferred and especially preferred meanings are described below, in each case for the individual substituents. The remaining
Substituenten der allgemeinen Formel (I), welche nachfolgend nicht genannt werden, weisen die oben genannte Bedeutung auf. Die erfindungsgemäß verwendeten Verbindungen der allgemeinen Formel (I) und ihre Salze werden nachfolgend als "Verbindungen der allgemeinen Formel (I)" bezeichnet. Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Substituents of the general formula (I) which are not mentioned below have the meaning given above. The compounds of the general formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)". Preferred subject matter of the invention are compounds of general formula (I), wherein
Q für die Gruppe Q for the group
Figure imgf000008_0001
Figure imgf000008_0001
Q-1 Q-2 steht, Q-1 Q-2 stands,
A unabhängig voneinander für O (Sauerstoff), oder die Gruppierung NR10 oder C-RUR12 stehen, wobei R10, R11 und R12 in den Gruppierungen NR10 oder C-RUR12 jeweils gleiche oder verschiedene Bedeutungen gemäß der unten stehenden Definition haben, A independently of one another represents O (oxygen), or the grouping NR 10 or CR U R 12 , where R 10 , R 11 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below to have,
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Halogen, Cyano, (Ci-Cv)-Alkyl, (Ci-Cvj-Haloalkyl, (Ci-Cv)-Hydroxyalkyl, (C 1-C7)-R 1 for halogen, cyano, (Ci-Cv) -alkyl, (Ci-Cvj-haloalkyl, (Ci-Cv) -hydroxyalkyl, (C 1-C7) -
Alkoxyalkyl, (Ci-Cv)-Alkoxy, (Ci-Cv)-Haloalkoxy, ( C 1 - C ^ ) - A 1 ky 1 th i 0 , (Ci-Cvj-Haloalkylthio, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor- Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5- Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4- Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor- Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor- Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-lod-Phenyl, 3-lod-Phenyl, 4-lod- Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4- Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2- Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor- Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5- Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2- Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl- Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl- Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy- Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2- Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2- Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2- Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl- Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor-Phenyl, 3- Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3- Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2- Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Alkoxyalkyl, (Ci-Cv) alkoxy, (Ci-Cv) haloalkoxy, (C 1 - C ^) - A 1 ky 1 th i 0, (Ci-Cvj-haloalkylthio, phenyl, 2-fluoro-phenyl, 3 -Fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl , 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4 - dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5 -Trichlor-phenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3 -lod-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chloro-phenyl , 3-bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl , 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chloro-phenyl , 2-fluorine -5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4 -Methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl - Phenyl, 2,4,5-trimethylphenyl, 3,4,5-trimethylphenyl, 2,4,6-trimethylphenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2, 4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy- Phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl , 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2 - methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy,
Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofüran-2-yl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)-alkyl, (C3-C7)- Halocycloalkyl, (C3-C7)-Halocycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl, (C2-C7)-Alkenyl, (C2-C7)-Alkenyloxy, (C2-C7)-Alkinyl steht,  Thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, (C3 -C9) -cycloalkyl, (C3-C9) -cycloalkyl- (Ci-C7) -alkyl, (C3-C7) -halocycloalkyl, (C3-C7) -halocycloalkyl- (Ci-C7) -alkyl, (Ci-C7 ) -Alkylcarbonyl, (C2-C7) -alkenyl, (C2-C7) -alkenyloxy, (C2-C7) -alkynyl,
R2 für Hydroxy, Hydrothio, Halogen, NR13R14, (Ci-C7)-Alkoxy, (C3-C9)-Cycloalkyl-(Ci-C7)- alkoxy, Aryl-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy, (Ci-C7)-Alkylcarbonyloxy, Phenylcarbonyloxy, p-Chlorphenylcarbonyloxy, m-Chlorphenylcarbonyloxy, 0- Chlorphenylcarbonyloxy, p-Fluorphenylcarbonyloxy, m-Fluorphenylcarbonyloxy, 0- Fluorphenylcarbonyloxy, Benzylcarbonyloxy, (C3-C9)-Cycloalkylcarbonyloxy, R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-C7) alkoxy, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkoxy, aryl- (Ci-C7) alkoxy , (Ci-C7) alkoxy- (Ci-C7) alkoxy, (Ci-C7) alkylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, 0-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, 0-fluorophenylcarbonyloxy , Benzylcarbonyloxy, (C3-C9) -cycloalkylcarbonyloxy,
Heterocyclylcarbonyloxy, (Ci-C7)-Haloalkyl-carbonyloxy, (C2-C7)-Alkenylcarbonyloxy, OC(0)OR15, OC(0)SR16, OC(S)OR15, OC(S)SR16, OSO2R16, OSO2OR15, OCHO steht, Heterocyclylcarbonyloxy, (Ci-C7) -haloalkyl-carbonyloxy, (C2-C7) -alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , OSO2R 16 , OSO2OR 15 , OCHO stands,
R3 für Wasserstoff, (Ci-C7)-Alkyl steht, R 3 represents hydrogen, (Ci-C7) -alkyl,
R4, R5, R6, R7,R8 und R9 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C7)-Alkyl, (Ci-C7)-Hydroxyalkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor- Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2- Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6- Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor- Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom- Phenyl, 2-lod-Phenyl, 3-lod-Phenyl, 4-lod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor- Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3 -Brom-5 -Fluor-Phenyl, 3-Brom-5- Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3- Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor- Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5- Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4- Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6- Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy- Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4- Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy- Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl- Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor- Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3- Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy- Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3 -Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin- 4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Benzyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, Cyano stehen, oder wobei R4, R5, R6, R7,R8 und R9 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen gesättigten oder teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7- gliedrigen Ring bilden, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (Ci-C 7 ) -hydroxyalkyl, (Ci-C 7 ) - Haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy- (Ci C7) alkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2 , 3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3rd -Chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl , 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl , 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro Phenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo- Phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro- Phenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chloro Phenyl, 2-fluoro-6-chlorophenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6- Dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2, 4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6- Trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluorometho xy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl- Phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chloro -Phenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl , 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl , Thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, benzyl, (C2-C 7 ) -Alkenyl, (C2-C7) -alkynyl, cyano, or where R 4 , R 5 , R 6 , R 7 , R 8 and R 9 together with the C atom to which they are each attached are saturated or partially saturated n, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted, in total 3-7-membered ring,
R10 für Wasserstoff, (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)- Cycloalkyl-(Ci- C7)-alkyl, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5- Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor- Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor- Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4- Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6- Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3- Brom-4-Chlor-Phenyl, 3 -Brom-5 -Fluor-Phenyl, 3-Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom- Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4- Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2- Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor- Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5- Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5- Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2- Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5- Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5- Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy- Phenyl, 2-Trifluormethoxy-Phenyl, 3 -Trifluormethoxy- Phenyl, 4-Trifluormethoxy-Phenyl, 2- Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2- Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl- Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor-Phenyl, 3- Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3- Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2- Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, R 10 for hydrogen, (Ci-C 7 ) alkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) - cycloalkyl- (Ci-C 7 ) - alkyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3- Difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chloro- Phenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3, 5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4- Bromophenyl, 2-iodophenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluoro- Phenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo- Phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro- Phenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chloro Phenyl, 2-fluoro-6-chlorophenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6- Dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2, 4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6- Trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl Phenyl, 4-T rifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chloro -Phenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorine -Phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl , 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy,
Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Benzyl, (C2-Cv)-Alkenyl, (C2-C7)-Alkinyl, CHO, C(0)OR15, Cyano-(Ci- Cv)-alkyl (Ci-C7)-Alkylcarbonyl steht, Thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, benzyl, (C2-Cv) alkenyl, (C2-C7) alkynyl, CHO, C (0) OR 15 , cyano- (Ci-Cv) alkyl (Ci-C7) alkylcarbonyl,
R11 und R12 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C7)-Alkyl, (C1-C7)-R 11 and R 12 independently of one another for hydrogen, hydroxy, halogen, (Ci-C7) -alkyl, (C1-C7) -
Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy, Phenyl, 2- Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6- Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor- Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor- Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5- Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom- Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4- Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3 -Brom-4 -Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3- Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom- Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4- Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3- Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3- Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl- Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl- Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy- Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy- Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5- Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy- Phenyl, 3-Trifluormethoxy-Phenyl, 4-Trifluormethoxy- Phenyl, 2-Difluormethoxy-Phenyl, 3- Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl- Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4- Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor-Phenyl, 3- Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3- Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2- Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4- Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-Haloalkyl, (C 3 -C 9 ) cycloalkyl, (C3-C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, (Ci-C 7 ) alkoxy, phenyl, 2-fluoro-phenyl, 3 -fluoro -Phenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3 , 5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichloro - Phenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlor -Phenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodine -Phenyl, 4-iodophenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluorophenyl, 3-bromo-4-chlorophenyl, 3 - Bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3 -Chlor-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2 -fluoro-5-chloro-Phe nyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2, 4,5-trimethyl Phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2, 5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3, 4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4- Difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl , 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl , 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl , 4-methylthio-phenyl, 2-trifluoromethylthio-P henyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridine-
2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Benzyl, (C2-Cv)-Alkenyl, (C2-C7)- Alkinyl, Cyano stehen, oder wobei R11 und R12 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7-gliedrigen Ring bilden, 2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, benzyl, (C2-Cv) alkenyl, (C2-C7) alkynyl, cyano, or wherein R 11 and R 12 together with the C atom to which they are each bound form a partially saturated, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted, a total of 3-7-membered ring form,
R13 und R14 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cv)-Alkyl, (Ci-Cv)-Cyanoalkyl, (Ci-Cv)-Haloalkyl, (Ci-C7)-Alkoxy-(Ci-Cv)-alkyl, Phenyl, 2-Fluor-Phenyl,R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cv) alkyl, (Ci-Cv) cyanoalkyl, (Ci-Cv) haloalkyl, (Ci-C7) alkoxy- (Ci Cv) alkyl, phenyl, 2-fluoro-phenyl,
3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl,3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl,
2.3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5- Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5- Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor- Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3- Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor- Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5- Fluor-Phenyl, 3-Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3- Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor- Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4- Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3-Methyl- Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl,2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3 - Chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4- Fluoro-phenyl, 3-bromo-4-chloro-phenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4- Bromophenyl, 3-fluoro-4-bromophenyl, 3-chloro-4-bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3 - Chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6- Chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl,
2.3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4- Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3- Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3- Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3- Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl- Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4- Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor-Phenyl, 3- Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3- Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2- Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4- Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin- 2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Benzyl, (C3-C9)-Cycloalkyl, (C3-C9)- Cycloalkyl-(Ci-C7)-alkyl, SO2R16, (Ci-Cv)-Alkoxycarbonyl, (C2-Cv)-Alkenyloxycarbonyl, (C2- C7)-Alkinyloxycarbonyl steht, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl- Phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3- Dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4- Trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chloro -Phenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorine -Phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl , 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl Furan 3-yl, benzyl, (C3-C9) -cycloalkyl, (C3-C9) -cycloalkyl- (Ci-C7) -alkyl, SO2R 16 , (Ci-Cv) -alkoxycarbonyl, (C2-Cv) -alkenyloxycarbonyl, ( C2-C7) -alkynyloxycarbonyl,
R15 für (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, Phenyl, 2-Fluor-Phenyl, 3-Fluor- Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3- Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor- Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor- Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5- Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4- Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3- Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3- Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl- Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl- Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl- Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl,R 15 for (Ci-C7) alkyl, (Ci-C7) haloalkyl, (C3-C9) cycloalkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4 -Difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5 -Trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3 -chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2 , 6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl , 2,4,6-trichlorophenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo -4-fluoro-phenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo -5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro -4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro -4-chlorophenyl, 3 fl uor-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl- Phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5- Trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl,
2.4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl,2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl,
3.4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy- Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl- Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor- Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3- Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy- Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluonnethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Benzyl, (C3-C9)-Cycloalkyl-(Ci-Cv)-alkyl steht, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2- Difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chloro Phenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chloro Phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, benzyl, (C3-C9) -cycloalkyl- (Ci-Cv) -alkyl,
R16 für (Ci-Cv)-Alkyl, (Ci-Cv)-Haloalkyl, (C3-C9)-Cycloalkyl, Phenyl, 2-Fluor-Phenyl, 3-Fluor- Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3- Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor- Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor- Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5- Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4- Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3- Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3- Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl- Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl- Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl- Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl,R 16 for (Ci-Cv) alkyl, (Ci-Cv) haloalkyl, (C3-C9) cycloalkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4 -Difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5 -Trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3 -chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2 , 6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl , 2,4,6-trichlorophenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo -4-fluoro-phenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo -5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro -4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro -4-chlorophenyl, 3 fl uor-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl- Phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5- Trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl,
2.4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl,2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl,
3.4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy- Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl- Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor- Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3- Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy- Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Benzyl, (C3-C9)-Cycloalkyl-(Ci-Cv)-alkyl steht. Besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2- Difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl -5-fluoro-phenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluoro-phenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxy -Phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl , Benzyl, (C3-C9) -cycloalkyl- (Ci-Cv) -alkyl. Particularly preferred subject matter of the invention are compounds of the general formula (I), in which
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 -R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 -
Methylpropyl, 2-Methylpropyl, l,l-Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 , 1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n- Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, l,l-Dimethylbutyl,Methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, l, l-dimethylbutyl,
1.2-Dimethylbutyl, l,3-Di-methylbutyl, 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, 1 -Ethyl-2-methylpropyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1 -Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, l,l'-Bi(cyclopropyl)-l-yl, l,l'-Bi(cyclopropyl)-2-yl, 2'-Methyl-l,l'- bi(cyclopropyl)-2-yl, 1 -Cyanocyclopropyl, 2-Cyanocyclopropyl, 1 -Methylcyclobutyl, 2- Methylcyclobutyl, 3 -Methylcyclobutyl, 3,3-Dimethylcyclobut-l-yl, 1 -Cyanocyclobutyl, 2- Cyanocyclobutyl, 3 -Cyanocyclobutyl, 3,3-Difluorcyclobut-l-yl, 3-Fluorcyclobut-l-yl, 2,2- Difluorcycloprop-l-yl, l-Fluorcycloprop-l-yl, 2-Fluorcycloprop-l-yl, 1 -Allylcyclopropyl, 1- Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2- Methylcyclohexyl, 3 -Methylcyclohexyl, 1 -Methoxycyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, Trifluormethyl, Pentafluorethyl, l,l,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, l-Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl,1,2-dimethylbutyl, l, 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, 1 -ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl, 2,3-dimethylcyclopropyl, l, l'-Bi (cyclopropyl) -l-yl, l, l'-Bi (cyclopropyl) -2-yl, 2'-methyl-l, l'-bi (cyclopropyl) -2-yl, 1-cyanocyclopropyl, 2 -Cyanocyclopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 3,3-difluorocyclobut-l-yl, 3-fluorocyclobut -l-yl, 2,2-difluorocycloprop-l-yl, l-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1 -vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl , 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromet hyl, pentafluoroethyl, l, l, 2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, l-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl
2.2.2-Trifluorethyl, Difluor-tert.-butyl, Chlormethyl, Brommethyl, Hydroxymethyl, 2.2.2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl,
Hydroxyethyl, Hydroxy-n-propyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert-Butyloxy, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, iso-Propyloxymethyl, Methoxyethyl, Ethoxyethyl, n-Propyloxyethyl, iso-Propyloxyethyl, Trifluormethoxy,  Hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, iso- Propyloxyethyl, trifluoromethoxy,
Difluormethoxy, Pentafluorethoxy, 2,2,l,l-Tetrafluorethoxy, 2,2,2-Trifluorethoxy, 2,2- Difluorethoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Trifluormethylthio, Pentafluorethylthio, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor- Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5- Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor- Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-lod-Phenyl, 3-lod- Phenyl, 4-lod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor- Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor-Phenyl, 2-Fluor-4- Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2- Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor- Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6- Chlor-Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5- Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5- Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2- Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5- Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy- Phenyl, 2-Trifluormethoxy-Phenyl, 3 -Trifluormethoxy- Phenyl, 4-Trifluormethoxy-Phenyl, 2- Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2- Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl- Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor-Phenyl, 3- Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3- Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2- Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Difluoromethoxy, pentafluoroethoxy, 2,2, l, l-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, 2-fluoro Phenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4- Difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2, 4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodo- Phenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluoro- Phenyl, 3-bromo-4-chloro-phenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo- Phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro Phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6-chloro Phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl Phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2- Methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3, 4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluorom ethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5- Bis (trifluoromethyl) phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy -5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthio-phenyl , 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy,
Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, cyclopropylmethyl, Cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Ethenyl, l-Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, l-Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl- l-propenyl, 2-Methyl- l-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2- propenyl, l-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- l-butenyl, 2-Methyl- 1- butenyl, 3 -Methyl- l-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- l-propenyl, 1 ,2-Dimethyl-2-propenyl, l-Ethyl- l-propenyl, 1 -Ethyl-2-propenyl, 1- Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl- l-pentenyl, 2-Methyl-l- pentenyl, 3 -Methyl- l-pentenyl, 4-Methyl- l-pentenyl, 1 -Methyl-2-pentenyl, 2-Methyl-2- pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3-pentenyl, 2-Methyl-3- pentenyl, 3-Methyl-3-pentenyl, 4-Methyl-3-pentenyl, l-Methyl-4-pentenyl, 2-Methyl-4- pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl, l,l-Dimethyl-3- butenyl, 1 ,2-Dimethyl- l-butenyl, 1 ,2-Dimethyl-2-butenyl, l,2-Dimethyl-3-butenyl, 1,3- Dimethyl- l-butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3-butenyl, 2,3-Dimethyl-l-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l- butenyl, 3,3-Dimethyl-2-butenyl, l-Ethyl- l-butenyl, 1 -Ethyl-2-butenyl, l-Ethyl-3-butenyl, 2- Ethyl- l-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, l,l,2-Trimethyl-2-propenyl, l-Ethyl-l- methyl-2-propenyl, l-Ethyl-2-methyl-l-propenyl und 1 -Ethyl-2-methyl-2-propenyl, Prop-2-en- l-yloxy, But-3-en-l-yloxy, Pent-4-en-l-yloxy, Ethinyl, l-Propinyl, 2-Propinyl, l-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, l-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1- Methyl-2-butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 -Methyl- l-butinyl, 1 , 1 -Dimethyl-2- propinyl, 1 -Ethyl-2-propinyl, l-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1- Methyl-2-pentinyl, l-Methyl-3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4- pentinyl, 3 -Methyl- l-pentinyl, 3-Methyl-4-pentinyl, 4-Methyl- l-pentinyl, 4-Methyl-2-pentinyl,Cyclohexylmethyl, ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, 1-methyl- 2-propenyl, 2-methyl-2-propenyl, l-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-l-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, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl- 3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl- 2-butenyl, l, l-dimethyl-3-bu tenyl, 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, l, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-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- l-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, l, l, 2-trimethyl-2-propenyl, l-ethyl-l- methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and 1-ethyl-2-methyl-2-propenyl, prop-2-en-l-yloxy, but-3-en-l-yloxy, Pent-4-en-l-yloxy, ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3- Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1 - Ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l-pentynyl, 4-methyl-2-pentynyl,
1.1 -Dimethyl-2-butinyl, l,l-Dimethyl-3-butinyl, l,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3- butinyl, 3, 3 -Dimethyl- l-butinyl, 1 -Ethyl-2-butinyl, l-Ethyl-3-butinyl, 2-Ethyl-3-butinyl, 1- Ethyl-l-methyl-2-propinyl steht, 1.1 -dimethyl-2-butynyl, l, l-dimethyl-3-butynyl, l, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3 -dimethyl-l-butynyl, 1 - Ethyl-2-butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-l-methyl-2-propynyl,
R2 für Hydroxy, Fluor, Chlor, Brom, Iod, Hydrothio, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 - Methylethylcarbonyloxy, n-Butylcarbonyloxy, 1 -Methylpropylcarbonyloxy, 2- Methylpropylcarbonyloxy, l,l-Dimethylethylcarbonyloxy, n-Pentylcarbonyloxy, 1- Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1,1- Dimethylpropylcarbonyloxy, 1 ,2-Dimethylpropylcarbonyloxy, 2,2-Dimethylpropylcarbonyloxy, 1 -Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1 -Methylpentylcarbonyloxy, 2- Methylpentylcarbonyloxy, 3 -Methylpentylcarbonyloxy, 4-Methylpentylcarbonyloxy, 1,1- Dimethylbutylcarbonyloxy, 1 ,2-Dimethylbutylcarbonyloxy, 1 ,3-Di-methylbutylcarbonyloxy,R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3 -methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1, 2-dimethylbutylcarbonyloxy, 1, 3-dimethylbutylcarbonyloxy,
2.2-Dimethylbutylcarbonyloxy, 2,3 -Dimethylbutylcarbonyloxy, 3 ,3 -Dimethylbutylcarbonyloxy, 1 -Ethylbutylcarbonyloxy, 2-Ethylbutylcarbonyloxy, l,l,2-Trimethylpropylcarbonyloxy, 1,2,2- Trimethylpropylcarbonyloxy, 1 -Ethyl- 1 -methylpropylcarbonyloxy, 1 -Ethyl-2- methylpropylcarbonyloxy, Phenylcarbonyloxy, p-Chlorphenylcarbonyloxy, m- Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p-Fluorphenylcarbonyloxy, m- Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3, 3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, l, l, 2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methyl-1-methyl-1-methyl-1-methyl Ethyl-2-methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy,
Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Cyclopentylcarbonyloxy,  Cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy,
Cyclohexylcarbonyloxy, Trifluormethylcarbonyloxy, Difluormethylcarbonyloxy,  Cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy,
Methoxycarbonyloxy, Ethoxycarbonyloxy, n-Propyloxycarbonyloxy, iso- Propyloxycarbonyloxy, n-Butyloxycarbonyloxy, l,l-Dimethylethyloxycarbonyloxy, 2,2- Dimethyl-propyloxycarbonyloxy, 2-Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy, Allylcarbonyloxy, Amino, Methylamino, Dimethylamino, Ethylamino, Diethylamino, n- Propylamino, iso-Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Benzylamino steht,  Methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, l, l-dimethylethyloxycarbonyloxy, 2,2-dimethyl-propyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy, allylcarbonyloxy, amino, methylaminoethyl, dimaminoamethylamino, dimethylamino Propylamino, iso-propylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino,
R3 für Wasserstoff, Methyl, Ethyl steht, und R 3 represents hydrogen, methyl, ethyl, and
Q für eine der in der folgenden Tabelle spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht
Figure imgf000018_0001
Figure imgf000019_0001
Q stands for one of the groupings Ql .1 to Ql .69 specifically mentioned in the following table
Figure imgf000018_0001
Figure imgf000019_0001
Ganz besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), wonn X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei Very particularly preferred subject matter of the invention are compounds of general formula (I), wonn X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1-R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
Methylpropyl, 2-Methylpropyl, l,l-Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 , 1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n- Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, l,l-Dimethylbutyl,Methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, l, l-dimethylbutyl,
1.2-Dimethylbutyl, l,3-Di-methylbutyl, 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, 1 -Ethyl-2-methylpropyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Pentafluorethyl, l,l,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Bromfluormethyl, l-Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl,1,2-dimethylbutyl, l, 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, 1 -ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, trifluoromethyl, pentafluoroethyl, l, l, 2,2-tetrafluorethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl Dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, l-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl,
2.2.2-Trifluorethyl, Difluor-tert.-butyl, Chlormethyl, Brommethyl, Hydroxymethyl, 2.2.2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl,
Hydroxyethyl, Hydroxy-n-propyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert-Butyloxy, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, iso-Propyloxymethyl, Methoxyethyl, Ethoxyethyl, n-Propyloxyethyl, iso-Propyloxyethyl, Trifluormethoxy,  Hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, iso- Propyloxyethyl, trifluoromethoxy,
Difluormethoxy, Pentafluorethoxy, 2,2,l,l-Tetrafluorethoxy, 2,2,2-Trifluorethoxy, 2,2- Difluorethoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Trifluormethylthio, Pentafluorethylthio, Phenyl, Phenyloxy, Cyclopropylmethyl, Cyclobutylmethyl,  Difluoromethoxy, pentafluoroethoxy, 2,2, l, l-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, cyclopropylmethyl cyclobutylmethyl,
Cyclopentylmethyl, Cyclohexylmethyl, Ethenyl, l-Propenyl, 2-Propenyl, l-Methyl-ethenyl, 1- Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- l-propenyl, 2-Methyl- l-propenyl, l-Methyl-2- propenyl, 2-Methyl-2-propenyl, l-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- 1- butenyl, 2-Methyl- l-butenyl, 3 -Methyl- l-butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3- Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3-Methyl-3-butenyl, 1 , 1 -Dimethyl- 2-propenyl, 1 ,2-Dimethyl- l-propenyl, 1 ,2-Dimethyl-2-propenyl, 1 -Ethyl- l-propenyl, l-Ethyl-2- propenyl, Prop-2-en-l-yloxy, But-3-en-l-yloxy, Pent-4-en-l-yloxy, Ethinyl, l-Propinyl, 2- Propinyl steht,  Cyclopentylmethyl, cyclohexylmethyl, ethenyl, l-propenyl, 2-propenyl, l-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-l-propenyl, 2-methyl-l-propenyl, l- Methyl-2-propenyl, 2-methyl-2-propenyl, l-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl- l-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3- butenyl, 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-l-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-l-propenyl, l-ethyl-2-propenyl, prop- 2-en-l-yloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, ethynyl, l-propynyl, 2-propynyl,
R2 für Hydroxy, Fluor, Chlor, Brom, Iod, Hydrothio, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 - Methylethylcarbonyloxy, n-Butylcarbonyloxy, 1 -Methylpropylcarbonyloxy, 2- Methylpropylcarbonyloxy, l,l-Dimethylethylcarbonyloxy, n-Pentylcarbonyloxy, 1- Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1,1- Dimethylpropylcarbonyloxy, 1 ,2-Dimethylpropylcarbonyloxy, 2,2-Dimethylpropylcarbonyloxy, 1 -Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1 -Methylpentylcarbonyloxy, 2- Methylpentylcarbonyloxy, 3 -Methylpentylcarbonyloxy, 4-Methylpentylcarbonyloxy, 1,1- Dimethylbutylcarbonyloxy, 1 ,2-Dimethylbutylcarbonyloxy, 1 ,3-Di-methylbutylcarbonyloxy, 2,2-Dimethylbutylcarbonyloxy, 2,3 -Dimethylbutylcarbonyloxy, 3 ,3 -Dimethylbutylcarbonyloxy, 1 -Ethylbutylcarbonyloxy, 2-Ethylbutylcarbonyloxy, 1 , 1 ,2-Trimethylpropylcarbonyloxy, 1 ,2,2- Trimethylpropylcarbonyloxy, 1 -Ethyl- 1 -methylpropylcarbonyloxy, 1 -Ethyl-2- methylpropylcarbonyloxy, Phenylcarbonyloxy, p-Chlorphenylcarbonyloxy, m- Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p-Fluorphenylcarbonyloxy, m- Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1, 2-dimethylbutylcarbonyloxy, 1, 3-dimethylbutylcarbonyloxy, 2,2-dimethyl 2,3-dimethylbutylcarbonyloxy, 3, 3 -dimethylbutylcarbonyloxy, 1 -ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1, 1, 2-trimethylpropylcarbonyloxy, 1, 2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylthanolyloxy, 1-ethyl methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy,
Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Cyclopentylcarbonyloxy,  Cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy,
Cyclohexylcarbonyloxy, Trifluormethylcarbonyloxy, Difluormethylcarbonyloxy,  Cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy,
Methoxycarbonyloxy, Ethoxycarbonyloxy, n-Propyloxycarbonyloxy, iso- Propyloxycarbonyloxy, n-Butyloxycarbonyloxy, l,l-Dimethylethyloxycarbonyloxy, 2,2- Dimethyl-propyloxycarbonyloxy, 2-Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy, Allylcarbonyloxy, Amino, Methylamino, Dimethylamino, Ethylamino, Diethylamino, n- Propylamino, iso-Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Benzylamino steht,  Methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, l, l-dimethylethyloxycarbonyloxy, 2,2-dimethyl-propyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy, allylcarbonyloxy, amino, methylaminoethyl, dimaminoamethylamino, dimethylamino Propylamino, iso-propylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino,
R3 für Wasserstoff steht, R 3 represents hydrogen,
Q für eine der in der oben stehenden Tabelle spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht. lm Speziellen bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (1), worin Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above. In a particularly preferred subject matter of the invention are compounds of the general formula (1), in which
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1-R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-
Methylpropyl, 2-Methylpropyl, l,l-Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1 , 1 -Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2-Dimethylpropyl, 1 -Ethylpropyl, n- Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3-Methylpentyl, 4-Methylpentyl, l,l-Dimethylbutyl,Methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, l, l-dimethylbutyl,
1 ,2-Dimethylbutyl, l,3-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3- Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 , 1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 - Ethyl-l-methylpropyl, 1 -Ethyl-2-methylpropyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Trifluormethyl, Pentafluorethyl, l,l,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, Chlordifluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, Chlormethy, Brommethyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n- Butyloxy, tert-Butyloxy, Methoxymethyl, Ethoxymethyl, Methoxyethyl, Ethoxyethyl, 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-l-methylpropyl, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, Trifluoromethyl, pentafluoroethyl, l, l, 2,2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl, chlorodifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, methoxy, ethoxy , n-propyloxy, iso-propyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl,
Trifluormethoxy, Difluormethoxy, 2,2,2-Trifluorethoxy, 2,2-Difluorethoxy, Methylthio, Ethylthio, Trifluormethylthio, Pentafluorethylthio, Phenyl, Phenyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 - Methyl- ethenyl, l-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1 -propenyl, 2-Methyl-l -propenyl, Trifluoromethoxy, difluoromethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-propenyl, 1-propenyl, 1-propenyl, 1-propenyl, 1-propenyl, 1-propenyl, 1-propenyl, 1-phenyl Methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,
1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, l-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, Prop-2-en-l-yloxy, But-3-en-l-yloxy, Pent-4-en-l-yloxy, Ethinyl, l-Propinyl, 2-Propinyl steht, 1-methyl-2-propenyl, 2-methyl-2-propenyl, l-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, prop-2-en-l-yloxy, but-3-en-l- yloxy, pent-4-en-l-yloxy, ethynyl, l-propynyl, 2-propynyl,
R2 für Hydroxy, Fluor, Chlor, Brom, Iod, Hydrothio, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 - Methylethylcarbonyloxy, n-Butylcarbonyloxy, 1 -Methylpropylcarbonyloxy, 2- Methylpropylcarbonyloxy, l,l-Dimethylethylcarbonyloxy, n-Pentylcarbonyloxy, 1- Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1,1- Dimethylpropylcarbonyloxy, 1 ,2-Dimethylpropylcarbonyloxy, 2,2-Dimethylpropylcarbonyloxy, 1 -Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1 -Methylpentylcarbonyloxy, 2- Methylpentylcarbonyloxy, 3 -Methylpentylcarbonyloxy, 4-Methylpentylcarbonyloxy, 1,1- Dimethylbutylcarbonyloxy, 1 ,2-Dimethylbutylcarbonyloxy, 1 ,3-Di-methylbutylcarbonyloxy, 2,2-Dimethylbutylcarbonyloxy, 2,3 -Dimethylbutylcarbonyloxy, 3 ,3 -Dimethylbutylcarbonyloxy, 1 -Ethylbutylcarbonyloxy, 2-Ethylbutylcarbonyloxy, 1 , 1 ,2-Trimethylpropylcarbonyloxy, 1 ,2,2- Trimethylpropylcarbonyloxy, 1 -Ethyl- 1 -methylpropylcarbonyloxy, 1 -Ethyl-2- methylpropylcarbonyloxy, Phenylcarbonyloxy, p-Chlorphenylcarbonyloxy, m- Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p-Fluorphenylcarbonyloxy, m- Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n -Methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3 -methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1, 2-dimethylbutylcarbonyloxy, 1, 3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3, -Dimethylbutylcarbonyloxy, 1 -ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1, 1, 2-trimethylpropylcarbonyloxy, 1, 2,2-trimethylpropylcarbonyloxy, 1 -ethyl-1-methylpropylcarbonyloxy, 1-eth yl-2-methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy,
Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, Cyclopentylcarbonyloxy,  Cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy,
Cyclohexylcarbonyloxy, Trifluormethylcarbonyloxy, Difluormethylcarbonyloxy,  Cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy,
Methoxycarbonyloxy, Ethoxycarbonyloxy, n-Propyloxycarbonyloxy, iso- Propyloxycarbonyloxy, n-Butyloxycarbonyloxy, l,l-Dimethylethyloxycarbonyloxy, 2,2- Dimethyl-propyloxycarbonyloxy, 2-Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy, Allylcarbonyloxy, Amino, Methylamino, Dimethylamino, Ethylamino, Diethylamino, n- Propylamino, iso-Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Benzylamino steht, R3 für Wasserstoff steht, Methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, l, l-dimethylethyloxycarbonyloxy, 2,2-dimethyl-propyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy, allylcarbonyloxy, amino, methylaminoethyl, dimaminoamethylamino, dimethylamino Propylamino, iso-propylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino, R 3 represents hydrogen,
und and
Q für eine der in der oben stehenden Tabelle spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht. Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
lm ganz Speziellen bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (1), worin Very particularly preferred subject matter of the invention are compounds of the general formula (1), in which
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Chlor, Brom, Methyl, Ethyl, 1 -Methylethyl, l,l-Dimethylethyl, Trifluormethyl, Methoxy, Ethoxy, Methoxymethyl, Methylthio, Ethylthio, Phenyl steht, R 1 represents chlorine, bromine, methyl, ethyl, 1-methylethyl, l, l-dimethylethyl, trifluoromethyl, methoxy, ethoxy, methoxymethyl, methylthio, ethylthio, phenyl,
R2 für Hydroxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 -R 2 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
Methylethylcarbonyloxy, 1 , 1 -Dimethylethylcarbonyloxy, 2-Methylpropylcarbonyloxy, Cyclopropylcarbonyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, 1,1- Dimethylethyloxycarbonyloxy, 2-Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy steht, Methylethylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, 2-methylpropylcarbonyloxy, cyclopropylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy,
R3 für Wasserstoff steht, R 3 represents hydrogen,
Q für eine der in der oben stehenden Tabelle spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht. Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in the table above.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (1) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können The general or preferred radical definitions listed above apply both to the end products of the general formula (1) and correspondingly to the starting or intermediate products required in each case for the preparation. These residual definitions can
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herste llbarkeit sind erfindungsgemäße Verbindungen der allgemeinen Formel (I) oder deren agrochemischen Salze oder quartären N-Derivate von besonderem Interesse, worin einzelne Reste eine der bereits genannten oder im Folgenden genannten bevorzugten Bedeutungen haben, oder insbesondere solche, worin eine oder mehrere der bereits genannten oder im folgenden genannten bevorzugten Bedeutungen kombiniert auftreten. can be combined with one another, i.e. also between the specified preferred ranges. Compounds according to the invention of the general formula (I) or their agrochemical salts or quaternary N-derivatives are of particular interest, above all for the reasons of the higher herbicidal activity, better selectivity and / or better preparability, in which individual residues are one of those already mentioned or below have preferred meanings mentioned, or in particular those in which one or more of the preferred meanings already mentioned or mentioned below occur in combination.
Im Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen: With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt, d.h. beispielsweise im Falle von (C2-Cg)-Alkenyloxy über das Sauerstoffatom, und im Falle von Heterocyclyl-(Ci-Cg)-alkyl oder R120(0)C-(Ci-Cg)-Alkyl jeweils über das C-Atom der Alkylgruppe. Unless otherwise defined, it generally applies to the designation of chemical groups that the connection to the framework or the rest of the molecule takes place via the last-mentioned structural element of the chemical group in question, ie for example in the case of (C2-Cg) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl- (Ci-Cg) -alkyl or R 12 0 (0) C- (Ci-Cg) -alkyl each via the C-atom of the alkyl group.
Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradketiges oder verzweigtes Alkylsulfonyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "alkylsulfonyl" - alone or as part of a chemical group - stands for straight-chain or branched alkylsulfonyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, z.B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfonyl wie Methylsulfonyl, Ethyl- sulfonyl, Propylsulfonyl, 1 -Methylethylsulfonyl, Butylsulfonyl, 1 -Methylpropylsulfonyl, 2-Methyl- propylsulfonyl, l,l-Dimethylethylsulfonyl, Pentylsulfonyl, 1 -Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3 -Methylbutylsulfonyl, l,l-Dimethylpropylsulfonyl, 1 ,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1 -Ethylpropylsulfonyl, Hexylsulfonyl, 1 -Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3 -Methylpentylsulfonyl, 4-Methylpentylsulfonyl, l,l-Dimethylbutylsulfonyl, l,2-Di- methylbutylsulfonyl, 1 ,3-Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3 ,3 -Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1 , 1 ,2-Trimethylpropylsulfonyl,Carbon atoms, for example (but not limited to) (Ci-C 6 ) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, l, l-dimethylethylsulfonyl, pentyl 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l, l-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonylsulfonyl, 1-methylsulfonyl, 1-methyl 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, l, l-dimethylbutylsulfonyl, l, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsylonyl, 2-ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl,
1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl. 1, 2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.
Erfindungsgemäß steht "Heteroarylsulfonyl" für gegebenenfalls substituiertes Pyridylsulfonyl, According to the invention, "heteroarylsulfonyl" represents optionally substituted pyridylsulfonyl,
Pyrimidinylsulfonyl, Pyrazinylsulfonyl oder gegebenenfalls substituiertes polycyclisches Pyrimidinylsulfonyl, pyrazinylsulfonyl or optionally substituted polycyclic
Heteroarylsulfonyl, hier insbesondere gegebenenfalls substituiertes Chinolinylsulfonyl, beispielsweise substituiert durch Fluor, Chlor, Brom, lod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 Kohlenstoffatomen, wie (Ci-Cio)-, (G-G,)- oder (Ci-C4)-Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- C6)-Alkylthio wie Methylthio, Ethylthio, Propylthio, 1 -Methylethylthio, Butylthio, 1 -Methylpropylthio, 2-Methylpropylthio, l,l-Dimethylethylthio, Pentylthio, 1 -Methylbutylthio, 2-Methylbutylthio, 3- Methylbutylthio, l,l-Dimethylpropylthio, 1 ,2-Dimethylpropylthio, 2,2-Dimethylpropylthio, 1- Ethylpropylthio, Hexylthio, 1 -Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, l,l-Dimethylbutylthio, 1 ,2-Dimethylbutylthio, l,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, l,l,2-Tri- methylpropylthio, 1 ,2,2-Trimethylpropylthio, l-Ethyl-l -methylpropylthio und 1 -Ethyl-2-methyl- propylthio. According to the invention, "alkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6 Carbon atoms, such as (Ci-Cio) -, (GG,) - or (Ci-C4) -alkylthio, for example (but not limited to) (Ci-C 6 ) -alkylthio such as methylthio, ethylthio, propylthio, 1-methylethylthio, Butylthio, 1-methylpropylthio, 2-methylpropylthio, l, l-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, l, l-dimethylpropylthio, 1, 2-dimethylpropylthio, 2,2-dimethylpropylthio Ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, l, l-dimethylbutylthio, 1, 2-dimethylbutylthio, l, 3-dimethylbutylthio, 2,2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, l, l, 2-trimethylpropylthio, 1, 2,2-trimethylpropylthio, l-ethyl-l-methylpropylthio and 1-ethyl-2- methyl propylthio.
„Alkenylthio“ bedeutet erfindungsgemäßt ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein According to the invention, “alkenylthio” means an alkenyl radical bonded via a sulfur atom, alkynylthio means an alkynyl radical bonded via a sulfur atom, cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom and cycloalkenylthio means one via a
Schwefelatom gebundenen Cycloalkenylrest. Sulfur atom-bonded cycloalkenyl radical.
„Alkylsulfmyl (Alkyl-S(=0)-)“, soweit nicht an anderer Stelle anders definiert steht erfindungsgemäß für Alkylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (G-G)- oder (C1-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfmyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfmyl, 2-Methylpropylsulfinyl,"Alkylsulfmyl (alkyl-S (= 0) -)", unless otherwise defined elsewhere, stands according to the invention for alkyl radicals which are bonded to the structure via -S (= 0) -, such as (Ci-Cio) -, ( GG) - or (C1-C4) - alkylsulfinyl, e.g. B. (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfmyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfmyl, 2-methylpropylsulfinyl,
1 , 1 -Dimethylethylsulfmyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, l,l-Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfmyl, 1 -Ethylpropylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfmyl, 2-Methylpentyl- sulfinyl, 3-Methylpentylsulfinyl, 4-Methylpentylsulfinyl, l,l-Dimethylbutylsulfmyl, 1 ,2-Dimethyl- butylsulfinyl, l,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfmyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1 -Ethylbutylsulfmyl, 2-Ethylbutylsulfinyl, l,l,2-Trimethylpropylsulfinyl, 1,2,2- Trimethylpropylsulfinyl, l-Ethyl-l -methylpropylsulfmyl und 1 -Ethyl-2-methylpropylsulfmyl. 1, 1 -dimethylethylsulfmyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, l, l-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfmyl, 1-ethylsulfylmethylsulfylsulfyl, methyl 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, l, l-dimethylbutylsulfmyl, 1, 2-dimethylbutylsulfinyl, l, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfmyl, 2,3-dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1-ethylbutylsulfmyl, 2-ethylbutylsulfinyl, l, l, 2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, l-ethyl-l-methylpropylsulfmyl and 1-ethyl-2-methylpropylsulfmyl.
Analog sind„Alkenylsulfinyl“ und„Alkinylsulfinyl“, erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfinyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfinyl. Analogous are “alkenylsulfinyl” and “alkynylsulfinyl”, defined according to the invention as alkenyl or alkynyl radicals which are bonded to the structure via -S (= 0) -, such as (C2-C10) -, (C2-C6) - or ( C2-C4) - alkenylsulfinyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfinyl.
Analog sind„Alkenylsulfonyl“ und„Alkinylsulfonyl“ erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)2- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfonyl. Analogously, “alkenylsulfonyl” and “alkynylsulfonyl” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the structure via -S (= 0) 2 -, such as (C2-C10) -, (C2-C6) - or ( C2-C4) - alkenylsulfonyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfonyl.
„Alkoxy“ bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2- Methylpropoxy, l,l-Dimethylethoxy, Pentoxy, 1 -Methylbutoxy, 2-Methylbutoxy, 3-Methylbutoxy, 1,1- Dimethylpropoxy, 1 ,2-Dimethylpropoxy, 2,2-Dimethylpropoxy, 1 -Ethylpropoxy, Hexoxy, 1 - Methylpentoxy, 2-Methylpentoxy, 3-Methylpentoxy, 4-Methylpentoxy, l,l-Dimethylbutoxy, l,2-Di- methylbutoxy, l,3-Dimethylbutoxy, 2,2-Dimethylbutoxy, 2,3-Dimethylbutoxy, 3,3-Dimethylbutoxy, 1- Ethylbutoxy, 2-Ethylbutoxy, l,l,2-Trimethylpropoxy, 1 ,2,2-Trimethylpropoxy, l-Ethyl-l -methyl propoxy und 1 -Ethyl-2-methylpropoxy. Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenoxy bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinoxy. “Alkoxy” means an alkyl radical bonded via an oxygen atom, eg. B. (but not limited to) (Ci-C 6 ) alkoxy such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2- Methylpropoxy, l, l-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1 - methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l, l-dimethylbutoxy, l, 2-dimethylbutoxy, l, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1- ethylbutoxy, 2-ethylbutoxy, l, l, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, l-ethyl-l-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy means an alkenyl radical bonded via an oxygen atom, alkynyloxy means an alkynyl radical bonded via an oxygen atom, such as (C2-C10), (C 2 -C 6 ) or (C 2 -C 4 ) alkenoxy or (C3-C10) -, (C3-C 6 ) - or (C3-C 4 ) alkynoxy.
„Cycloalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. “Cycloalkyloxy” means a cycloalkyl radical bonded via an oxygen atom and cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
„Alkylcarbonyl“ (Alkyl-C(=0)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (Ci-Cio)-, (Ci-Cr,)- oder (C 1-C4)- Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der "Alkylcarbonyl" (alkyl-C (= 0) -), unless otherwise defined elsewhere, stands according to the invention for alkyl radicals which are bonded to the structure via -C (= 0) -, such as (Ci-Cio) -, (Ci-Cr,) - or (C 1-C4) alkylcarbonyl. The number of carbon atoms refers to the alkyl radical in the
Alkylcarbonylgruppe. Alkylcarbonyl.
Analog stehen„Alkenylcarbonyl“ und„Alkinylcarbonyl“, soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C2-C 10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyl bzw. (C2-C 10)-, (C2-C6)- oder (C2-C4)- Alkinylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonylgruppe. Analogously, “alkenylcarbonyl” and “alkynylcarbonyl”, unless otherwise defined elsewhere, stand according to the invention for alkenyl or alkynyl radicals which are bonded to the structure via -C (= 0) -, such as (C2-C 10) -, (C2-C6) - or (C2-C4) -alkenylcarbonyl or (C2-C10) -, (C2-C6) - or (C2-C4) - alkynylcarbonyl. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
„Alkoxycarbonyl (Alkyl-0-C(=0)-)“, soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (CI-CÖ)- oder (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Analog stehen „Alkenyloxycarbonyl“ und„Alkinyloxycarbonyl“, soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C2-C 10)-, (C2-C6)- oder (C2-C4)-Alkenyloxycarbonyl bzw. (C3-C 10)-, (C3-C6)- oder (C3-C4)- Alkinyloxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alken- bzw. Alkinyloxycarbonylgruppe. "Alkoxycarbonyl (alkyl-0-C (= 0) -)", unless otherwise defined elsewhere: alkyl residues which are bonded to the structure via -0-C (= 0) -, such as (C1-C10) - , (C I -C Ö ) - or (Ci-C 4 ) alkoxycarbonyl. The number of carbon atoms relates to the alkyl radical in the alkoxycarbonyl group. Analogously, "alkenyloxycarbonyl" and "alkynyloxycarbonyl", unless otherwise defined elsewhere, according to the invention stand for alkenyl or alkynyl radicals which are bonded to the structure via -0-C (= 0) -, such as (C2-C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) alkenyloxycarbonyl or (C3-C 10) -, (C 3 -C 6 ) - or (C3-C4) - alkynyloxycarbonyl. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkene or alkynyloxycarbonyl group.
Der Begriff„Alkylcarbonyloxy“ (Alkyl-C(=0)-0-) steht erfindungsgemäß, soweit nicht an anderer Stelle anders definiert, für Alkylreste, die über eine Carbonyloxygruppe (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C1-C10)-, (CI-CÖ)- oder (Ci-C4)-Alkylcarbonyloxy. Die Anzahl der C- Atome bezieht sich dabei auf den Alkylrest in der Alkylcarbonyloxygruppe. Analog sind„Alkenylcarbonyloxy“ und„Alkinylcarbonyloxy“ erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyloxy bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkinylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonyloxygruppe. The term “alkylcarbonyloxy” (alkyl-C (= 0) -0-) according to the invention, unless otherwise defined elsewhere, stands for alkyl radicals which are present with the oxygen via a carbonyloxy group (-C (= 0) -0-) the backbone are bound, such as (C1-C10) -, (C I -C Ö ) - or (Ci-C 4 ) -alkylcarbonyloxy. The number of carbon atoms relates to the alkyl radical in the alkylcarbonyloxy group. Analogously, “alkenylcarbonyloxy” and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the structure via (-C (= 0) -0-) with the oxygen, such as (C2-C10) -, (C2 -C6) - or (C2-C4) -alkenylcarbonyloxy or (C2-C10) -, (C2-C6) - or (C2-C4) -alkynylcarbonyloxy. The number of carbon atoms relates to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
In Kurzformen wie z.B. C(0)OR15, 0C(0)NR13R14, oder C(0)NR13R14 steht die in Klammem aufgeführte Kurzform O für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes Sauerstoffatom. ln Kurzformen wie z.B. OC(S)OR15, OC(S)SR16, OC(S)NR13R14, steht die in Klammem aufgeführte Kurzform S für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes In short forms such as C (0) OR 15 , 0C (0) NR 13 R 14 , or C (0) NR 13 R 14 , the short form O in brackets stands for an oxygen atom bonded to the adjacent carbon atom via a double bond. In short forms such as OC (S) OR 15 , OC (S) SR 16 , OC (S) NR 13 R 14 , the short form S shown in brackets stands for one bound to the adjacent carbon atom via a double bond
Schwefelatom. Sulfur atom.
Der Begriff„Aryl“ bedeutet ein gegebenenfalls substituiertes mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C- Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl. The term “aryl” means an optionally substituted mono-, bi- or polycyclic aromatic system with preferably 6 to 14, in particular 6 to 10 ring carbon atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Vom Begriff„gegebenenfalls substituiertes Aryl“ sind auch mehrcyclische Systeme, wie The term “optionally substituted aryl” also includes multi-cyclic systems such as
Tetrahydronaphtyl, lndenyl, lndanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl“ in der Regel auch von dem Begriff „gegebenenfalls substituiertes Phenyl“ umfasst. Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris- [alkyl] silyl, Bis-[alkyl]arylsilyl, Bis-[alkyl]alkylsilyl, Tris-[alkyl]silylalkinyl, Arylalkinyl, Tetrahydronaphthyl, indyl, indanyl, fluorenyl, biphenylyl, wherein the binding site is on the aromatic system. Systematically, “aryl” is usually also included in the term “optionally substituted phenyl”. Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkyl, haloalkyl, haloalkyl Haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl] silylalkynyl, arylalkynyl,
Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino, Heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino,
Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino,
Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl,  Arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Alkylaminocarbonyl, cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
Arylalkoxy. Arylalkoxy.
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
(=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza-bicyclo[3.2.l]octanyl, 8-Aza-bicyclo[2.2.2]octanyl oder l-Aza- bicyclo[2.2.l]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch (= carbocyclic ring in which at least one C atom is replaced by a hetero atom, preferably by a hetero atom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or is heteroaromatic and can be unsubstituted or substituted, the binding site being located on a ring atom. If the heterocyclyl radical or the heterocyclic ring is optionally substituted, it can be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, multi-cyclic systems are also included, such as, for example, 8-azabicyclo [3.2.l] octanyl, 8-azabicyclo [2.2.2] octanyl or l-azabicyclo [2.2.l] heptyl. In the case of optionally substituted heterocyclyl also
spirocyclische Systeme umfasst, wie beispielsweise l-Oxa-5-aza-spiro[2.3]hexyl. Wenn nicht anders definiert, enthält der heterocyclische Ring vorzugsweise 3 bis 9 Ringatome, insbesondere 3 bis 6 Ringatome, und ein oder mehrere, vorzugsweise 1 bis 4, insbesondere 1 , 2 oder 3 Heteroatome im heterocyclischen Ring, vorzugsweise aus der Gruppe N, O, und S, wobei jedoch nicht zwei includes spirocyclic systems such as l-oxa-5-aza-spiro [2.3] hexyl. Unless otherwise defined, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3, heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
Sauerstoffatome direkt benachbart sein sollen, wie beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1- oder 2- oder 3-Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-lH-pyrrol-Oxygen atoms are said to be directly adjacent, for example with a heteroatom from the group N, O and S 1- or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrol-2- or 3-yl, 2,3- dihydro-lH-pyrrole
1- oder 2- oder 3- oder 4- oder 5-yl; 2,5-Dihydro-lH-pyrrol-l- oder 2- oder 3-yl, 1- oder 2- oder 3- oder 4-Piperidinyl; 2,3,4,5-Tetrahydropyridin-2- oder 3- oder 4- oder 5-yl oder 6-yl; 1 ,2,3,6- Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2,3,4-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,4-Dihydropyridin-l- oder 2- oder 3- oder 4-yl; 2,3-Dihydropyridin-1- or 2- or 3- or 4- or 5-yl; 2,5-dihydro-1H-pyrrole-1- or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridin-2- or 3- or 4- or 5-yl or 6-yl; 1, 2,3,6-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 2,3,4-tetrahydropyridin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 4-dihydropyridin-l- or 2- or 3- or 4-yl; 2,3-dihydropyridine
2- oder 3- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyridin-2- oder 3- oder 4- oder 5- oder 6-yl, 1- oder 2- oder 3- oder 4-Azepanyl; 2,3,4,5-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3, 6, 7- Tetrahydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 3,4,5,6-Tetrahydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-lH-azepin-l- oder 2- oder 3- oder 4-yl; 2,5-Dihydro-lH-azepin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridin-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-lH-azepine-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-lH-azepine-1- or 2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3, 6, 7-tetrahydro-lH-azepine-l- or 2- or 3- or 4-yl; 3,4,5,6-tetrahydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-lH-azepine-l- or 2- or 3- or 4-yl; 2,5-dihydro-lH-azepin-
1- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- yl; 2,3-Dihydro-lH-azepin-l- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,4-Dihydro-2H-azepin-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-lH-azepine-l- or -2- or 3- or 4-yl; 2,3-dihydro-lH-azepine-l- or -2- or 3- or 4- or 5- or 6- or 7-yl; 3,4-dihydro-2H-azepine
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 5,6-dihydro-2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-3H-azepine
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; lH-Azepin-l- oder -2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4H-Azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl, 2- oder 3-Oxolanyl (= 2- oder 3- Tetrahydrofuranyl); 2,3-Dihydrofuran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofuran-2- oder 3-yl, 2- oder 3- oder 4-Oxanyl (= 2- oder 3- oder 4-Tetrahydropyranyl); 3,4-Dihydro-2H-pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-pyran-2- oder 3-oder 4- oder 5- oder 6-yl; 2H-Pyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Pyran-2- oder 3- oder 4-yl, 2- oder 3- oder 4-Oxepanyl; 2, 3,4,5- Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepine-1- or -2- or 3- or 4- or 5- or 6- or 7-yl; 2H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4H-azepin-2- or 3- or 4- or 5- or 6- or 7-yl, 2- or 3-oxolanyl (= 2- or 3-tetrahydrofuranyl); 2,3-dihydrofuran-2- or 3- or 4- or 5-yl; 2,5-dihydrofuran-2- or 3-yl, 2- or 3- or 4-oxanyl (= 2- or 3- or 4-tetrahydropyranyl); 3,4-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-pyran-2- or 3- or 4- or 5- or 6-yl; 2H-pyran-2- or 3- or 4- or 5- or 6-yl; 4H-pyran-2- or 3- or 4-yl, 2- or 3- or 4-oxepanyl; 2, 3,4,5-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2 or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3- Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2- or 3- or 4-yl; 2,5-dihydrooxepin-2- or 3- or 4- or 5- or 6- or 7-yl; Oxepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2- or 3- or 4- or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2- or 3- or 4- or
5- oder 6-yl; 3,6-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring- Heterocyclen sind beispielsweise 1- oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1- oder 2- oder 3-Azetidinyl,5- or 6-yl; 3,6-dihydro-2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 2H-thiopyran-2- or 3- or 4- or 5- or 6-yl; 4H-thiopyran-2- or 3- or 4-yl. Preferred 3-ring and 4-ring heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl,
2- oder 3-Oxetanyl, 2- oder 3-Thietanyl, l,3-Dioxetan-2-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit zwei Heteroatomen aus der Gruppe N,2- or 3-oxetanyl, 2- or 3-thietanyl, l, 3-dioxetan-2-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with two heteroatoms from group N,
O und S, wie beispielsweise 1- oder 2- oder 3- oder 4-Pyrazolidinyl; 4,5-Dihydro-3H-pyrazol- 3- oder 4- oder 5-yl; 4,5-Dihydro-lH-pyrazol-l- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-lH-pyrazol-l- oder 2- oderO and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazol-3- or 4- or 5-yl; 4,5-dihydro-1H-pyrazole-l- or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 or 2- or
3- oder 4- oder 5-yl; 1- oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-lH-imidazol-l- oder 2- oder3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-lH-imidazole-l- or 2- or
3- oder 4-yl; 2,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; 4,5-Dihydro-lH-imidazol-l- oder 2- oder 4- oder 5-yl; Hexahydropyridazin-l- oder 2- oder 3- oder 4-yl; l,2,3,4-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2,3,6-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder3- or 4-yl; 2,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; 4,5-dihydro-1H-imidazole-1- or 2- or 4- or 5-yl; Hexahydropyridazin-l- or 2- or 3- or 4-yl; l, 2,3,4-tetrahydropyridazin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 2,3,6-tetrahydropyridazine-l- or 2- or 3- or 4- or 5- or
6-yl; l,4,5,6-Tetrahydropyridazin-l- oder 3- oder 4- oder 5- oder 6-yl; 3,4,5,6-Tetrahydropyridazin-3- oder 4- oder 5-yl; 4,5-Dihydropyridazin-3- oder 4-yl; 3,4-Dihydropyridazin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydropyridazin-3- oder 4-yl; l,6-Dihydropyriazin-l- oder 3- oder 4- oder 5- oder 6-yl; 6-yl; l, 4,5,6-tetrahydropyridazin-l- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazin-3- or 4- or 5-yl; 4,5-dihydropyridazin-3- or 4-yl; 3,4-dihydropyridazin-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazin-3- or 4-yl; l, 6-dihydropyriazin-l- or 3- or 4- or 5- or 6-yl;
Hexahydropyrimidin-l- oder 2- oder 3- oder 4-yl; l,4,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; l,2,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1 ,2,3,4- Tetrahydropyrimidin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,6-Dihydropyrimidin-l- oder 2- oderHexahydropyrimidin-l- or 2- or 3- or 4-yl; l, 4,5,6-tetrahydropyrimidin-l- or 2- or 4- or 5- or 6-yl; l, 2,5,6-tetrahydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1, 2,3,4-tetrahydropyrimidin-l- or 2- or 3- or 4- or 5- or 6-yl; l, 6-dihydropyrimidine-l- or 2- or
4- oder 5- oder 6-yl; l,2-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-4- or 5- or 6-yl; l, 2-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 2,5-dihydropyrimidine
2- oder 4- oder 5-yl; 4,5-Dihydropyrimidin- 4- oder 5- oder 6-yl; l,4-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; l,2,3,6-Tetrahydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; l,2,3,4-Tetrahydropyrazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; l,2-Dihydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; l,4-Dihydropyrazin-l- oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder2- or 4- or 5-yl; 4,5-dihydropyrimidin-4- or 5- or 6-yl; l, 4-dihydropyrimidin-l- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; l, 2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl; l, 2,3,4-tetrahydropyrazine-1- or 2- or 3- or 4- or 5- or 6-yl; l, 2-dihydropyrazine-1- or 2- or 3- or 5- or 6-yl; l, 4-dihydropyrazine-1- or 2- or 3-yl; 2,3-dihydropyrazine-2- or
3- oder 5- oder 6-yl; 2,5-Dihydropyrazin-2- oder 3-yl; l,3-Dioxolan-2- oder 4- oder 5-yl; l,3-Dioxol-2- oder 4-yl; l,3-Dioxan-2- oder 4- oder 5-yl; 4H-l,3-Dioxin-2- oder 4- oder 5- oder 6-yl; l,4-Dioxan-2- oder 3- oder 5- oder 6-yl; 2,3-Dihydro-l,4-dioxin-2- oder 3- oder 5- oder 6-yl; l,4-Dioxin-2- oder 3-yl;3- or 5- or 6-yl; 2,5-dihydropyrazin-2- or 3-yl; l, 3-dioxolan-2- or 4- or 5-yl; l, 3-dioxol-2- or 4-yl; l, 3-dioxan-2- or 4- or 5-yl; 4H-l, 3-dioxin-2- or 4- or 5- or 6-yl; l, 4-dioxan-2- or 3- or 5- or 6-yl; 2,3-dihydro-l, 4-dioxin-2- or 3- or 5- or 6-yl; 1,4-dioxin-2- or 3-yl;
1.2-Dithiolan-3- oder 4-yl; 3H-l,2-Dithiol-3- oder 4- oder 5-yl; l,3-Dithiolan-2- oder 4-yl; l,3-Dithiol- 2- oder 4-yl; l,2-Dithian-3- oder 4-yl; 3,4-Dihydro-l,2-dithiin-3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-1,2-dithiolan-3- or 4-yl; 3H-l, 2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2- or 4-yl; l, 3-dithiol-2- or 4-yl; 1,2-dithian-3- or 4-yl; 3,4-dihydro-l, 2-dithiin-3- or 4- or 5- or 6-yl; 3,6-dihydro-
1.2-dithiin-3- oder 4-yl; l,2-Dithiin-3- oder 4-yl; l,3-Dithian-2- oder 4- oder 5-yl; 4H-l,3-Dithiin-2- oder 4- oder 5- oder 6-yl; Isoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder1,2-dithiin-3- or 4-yl; 1,2-dithiin-3- or 4-yl; l, 3-dithian-2- or 4- or 5-yl; 4H-l, 3-dithiin-2- or 4- or 5- or 6-yl; Isoxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-yl;4- or 5-yl; 2,5-dihydroisoxazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisoxazol-3- or 4- or 5-yl;
1.3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-oxazol-2- oder 4- oder 5-yl; l,2-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,2-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,2-oxazin-3- oder 4- oder 5- oder 6-yl; 2H-l,2-Oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 6H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; 4H-l,2-Oxazin-3- oder 4- oder 5- oder 6-yl; l,3-Oxazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,3-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-1,3-oxazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l, 3-oxazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l, 3-oxazol-2- or 4- or 5-yl; 4,5-dihydro-l, 3-oxazol-2- or 4- or 5-yl; l, 2-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l, 2-oxazin-3- or 4- or 5- or 6-yl; 2H-l, 2-oxazin-2- or 3- or 4- or 5- or 6-yl; 6H-l, 2-oxazin-3- or 4- or 5- or 6-yl; 4H-l, 2-oxazin-3- or 4- or 5- or 6-yl; l, 3-oxazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 3-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 3-oxazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H
1.3-oxazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-oxazin-2- oder 4- oder 5- oder 6-yl; 2H-1,3-oxazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l, 3-oxazin-2- or 4- or 5- or 6-yl; 2H
1.3-Oxazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Oxazin-2- oder 4- oder 5- oder 6-yl; Morpholin-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-l,4-oxazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6-Dihydro-2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 2H-l,4-oxazin-2- oder 3- oder 5- oder 6-yl; 4H-l,4-oxazin-2- oder 3-yl; 1 ,2-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,3,4,5-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,2- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,2-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,2- oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,2-oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,2-Oxazepin-3- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepan-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,3- oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 2,5,6,7-Tetrahydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,5,6,7-Tetrahydro-l,3- oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,3-oxazepin-2- oder 3- oder 4- oder 5- oder1,3-oxazin-2- or 4- or 5- or 6-yl; 6H-l, 3-oxazin-2- or 4- or 5- or 6-yl; 4H-l, 3-oxazin-2- or 4- or 5- or 6-yl; Morpholin-2- or 3- or 4-yl; 3,4-dihydro-2H-l, 4-oxazin-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-l, 4-oxazin-2- or 3- or 5- or 6-yl; 2H-l, 4-oxazin-2- or 3- or 5- or 6-yl; 4H-l, 4-oxazin-2- or 3-yl; 1, 2-oxazepan-2- or 3- or 4- or 5- or 6- or 7- yl; 2,3,4,5-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l, 2-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 4,5,6,7-tetrahydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 2-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l, 2-oxazepin-3- or 4- or 5- or 6- or 7-yl; l, 3-oxazepan-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 3-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 3-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 2,5,6,7-tetrahydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 3-oxazepine-2- or 3- or 4- or 5- or
6- oder 7-yl; 2,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 2,7-Dihydro-l,3-oxazepin- 2- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 4,7- Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-l,3-oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; l,3-Oxazepin-2- oder 4- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3,4,5-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2, 3, 4, 7- Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydro-l,4-oxazepin-6- or 7-yl; 2,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-l, 3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepin-2- or 4- or 5- or 6- or 7-yl; 1, 4-oxazepan-2- or 3- or 5- or 6- or 7-yl; 2,3,4,5-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2, 3, 4, 7-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-l, 4-oxazepin
2- oder 3- oder 5- oder 6- oder 7-yl; 2,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7- yl; 4,5,6,7-Tetrahydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-l,4- oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,5-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder2- or 3- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-l, 4-oxazepine-2- or 3- or 5- or 6- or 7- yl; 4,5,6,7-tetrahydro-l, 4-oxazepin-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 2,5-dihydro-l, 4-oxazepine-2- or 3- or 5- or 6- or
7-yl; 2,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-l,4-oxazepin-2- oder7-yl; 2,7-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-l, 4-oxazepine-2- or
3- oder 4- oder 5- oder 6- oder 7-yl; 4,7-Dihydro-l,4-oxazepin-2- oder 3- oder 4- oder 5- oder 6- oder 7- yl; 6,7-Dihydro-l,4-oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 1 ,4-Oxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; Isothiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisothiazol-2- oder 3- oder 4- oder 5- yl; 2,5-Dihydroisothiazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisothiazol-3- oder 4- oder 5-yl; 1,3- Thiazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-thiazol-2- oder 3- oder 4- oder 5-yl; 2,5- Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; 4,5-Dihydro-l,3-thiazol-2- oder 4- oder 5-yl; l,3-Thiazinan-2- oder 3- oder 4- oder 5- oder 6-yl; 3,4-Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 3,6- Dihydro-2H-l,3-thiazin-2- oder 3- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-2H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 5,6-Dihydro-4H-l,3-thiazin-2- oder 4- oder 5- oder 6-yl; 2H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 6H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl; 4H-l,3-Thiazin-2- oder 4- oder 5- oder 6-yl. Weitere Beispiele für“Heterocyclyl“ sind ein partiell oder vollständig hydrierter heterocyclischer Rest mit 3 Heteroatomen aus der Gruppe N, O und S, wie beispielsweise l,4,2-Dioxazolidin-2- oder 3- oder 5-yl; l,4,2-Dioxazol-3- oder 5-yl; 1 ,4,2-Dioxazinan-2- oder -3- oder 5- oder 6-yl; 5,6-Dihydro-l,4,2- dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazin-3- oder 5- oder 6-yl; l,4,2-Dioxazepan-2- oder 3- oder 5- oder 6- oder 7-yl; 6,7-Dihydro-5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-7H-l,4,2- Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 2,3-Dihydro-5H-l,4,2-Dioxazepin-2- oder 3- oder 5- oder 6- oder 7-yl; 5H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl; 7H-l,4,2-Dioxazepin-3- oder 5- oder 6- oder 7-yl. Strukturbeispiele für gegebenenfalls weiter substituierte Heterocyclen sind auch im Folgenden aufgeführt: 3- or 4- or 5- or 6- or 7-yl; 4,7-dihydro-l, 4-oxazepine-2- or 3- or 4- or 5- or 6- or 7- yl; 6,7-dihydro-l, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; 1, 4-oxazepin-2- or 3- or 5- or 6- or 7-yl; Isothiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazol-2- or 3- or 4- or 5-yl; 2,5-dihydroisothiazol-2- or 3- or 4- or 5-yl; 4,5-dihydroisothiazol-3- or 4- or 5-yl; 1,3-thiazolidin-2- or 3- or 4- or 5-yl; 2,3-dihydro-l, 3-thiazol-2- or 3- or 4- or 5-yl; 2,5-dihydro-l, 3-thiazol-2- or 4- or 5-yl; 4,5-dihydro-l, 3-thiazol-2- or 4- or 5-yl; l, 3-thiazinan-2- or 3- or 4- or 5- or 6-yl; 3,4-dihydro-2H-l, 3-thiazin-2- or 3- or 4- or 5- or 6-yl; 3,6- Dihydro-2H-l, 3-thiazin-2- or 3- or 4- or 5- or 6-yl; 5,6-dihydro-2H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 2H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 6H-l, 3-thiazin-2- or 4- or 5- or 6-yl; 4H-l, 3-thiazin-2- or 4- or 5- or 6-yl. Further examples of “heterocyclyl” are a partially or fully hydrogenated heterocyclic radical with 3 heteroatoms from the group N, O and S, such as l, 4,2-dioxazolidin-2- or 3- or 5-yl; l, 4,2-dioxazol-3- or 5-yl; 1, 4,2-dioxazinan-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazin-3- or 5- or 6-yl; l, 4,2-dioxazepan-2- or 3- or 5- or 6- or 7-yl; 6,7-dihydro-5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 2,3-dihydro-7H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 2,3-dihydro-5H-l, 4,2-dioxazepin-2- or 3- or 5- or 6- or 7-yl; 5H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl; 7H-l, 4,2-dioxazepin-3- or 5- or 6- or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
Figure imgf000031_0001
31
Figure imgf000031_0001
31
Figure imgf000032_0001
Figure imgf000033_0001
Figure imgf000032_0001
Figure imgf000033_0001
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl, The heterocycles listed above are preferably, for example, by hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, tris-alkylsilylalkynyl, nitro, amino, cyano, haloalkoxy,
Haloalkylthio, Alkylthio, Hydrothio, Hydroxyalkyl, Oxo, Heteroarylalkoxy, Arylalkoxy, Haloalkylthio, alkylthio, hydrothio, hydroxyalkyl, oxo, heteroarylalkoxy, arylalkoxy,
Heterocyclylalkoxy, Heterocyclylalkylthio, Heterocyclyloxy, Heterocyclylthio, Heteroaryloxy, Bis- alkylamino, Alkylamino, Cycloalkylamino, Hydroxycarbonylalkylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Alkoxycarbonylalkyl(alkyl)amino, Aminocarbonyl, Heterocyclylalkoxy, heterocyclylalkylthio, heterocyclyloxy, heterocyclylthio, heteroaryloxy, bis-alkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminoc
Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl,
Arylalkoxycarbonylalkylaminocarbonyl substituiert. Arylalkoxycarbonylalkylaminocarbonyl substituted.
Wenn ein Grundkörper "durch einen oder mehrere Reste" aus einer Aufzählung von Resten (= Gruppe) oder einer generisch definierten Gruppe von Resten substituiert ist, so schließt dies jeweils die gleichzeitige Substitution durch mehrere gleiche und/oder strukturell unterschiedliche Reste ein. Handelt es sich es sich um einen teilweise oder vollständig gesättigten Stickstoff-Heterocyclus, so kann dieser sowohl über Kohlenstoff als auch über den Stickstoff mit dem Rest des Moleküls verknüpft sein. If a basic body is substituted “by one or more residues” from an enumeration of residues (= group) or a generically defined group of residues, this includes the simultaneous substitution by several identical and / or structurally different residues. If the nitrogen heterocycle is partially or fully saturated, it can this is linked to the rest of the molecule via both carbon and nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Oxogruppe als Substituent an einem Ring- C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(0)-Gruppen sind jeweils beide Enantiomere umfasst. Possible substituents for a substituted heterocyclic radical are the substituents mentioned below, and also oxo and thioxo. The oxo group as a substituent on a ring carbon atom then means, for example, a carbonyl group in the heterocyclic ring. This preferably also includes lactones and lactams. The oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example in the case of N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 ( also briefly SO2) in the heterocyclic ring. In the case of -N (O) - and -S (0) groups, both enantiomers are included.
Erfindungsgemäß steht der Ausdruck„Heteroaryl“ für heteroaromatische Verbindungen, d. h. According to the invention, the term “heteroaryl” stands for heteroaromatic compounds, ie. H.
vollständig ungesättigte aromatische heterocyclische Verbindungen, vorzugsweise für 5- bis 7-gliedrige Ringe mit 1 bis 4, vorzugsweise 1 oder 2 gleichen oder verschiedenen Heteroatomen, vorzugsweise O, S oder N. Erfindungsgemäße Heteroaryle sind beispielsweise lH-Pyrrol-l-yl; lH-Pyrrol-2-yl; lH-Pyrrol-completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings with 1 to 4, preferably 1 or 2 identical or different heteroatoms, preferably O, S or N. Heteroaryls according to the invention are, for example, 1H-pyrrol-l-yl; lH-pyrrol-2-yl; lH-pyrrole
3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l-yl; lH-Imidazol-2-yl; lH-Imidazol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-imidazol-l-yl; lH-imidazol-2-yl; lH-imidazole
4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, lH-l,2,3- Triazol-l-yl, lH-l,2,3-Triazol-4-yl, lH-l,2,3-Triazol-5-yl, 2H-l,2,3-Triazol-2-yl, 2H-l,2,3-Triazol-4-yl, lH-l,2,4-Triazol-l-yl, lH-l,2,4-Triazol-3-yl, 4H-l,2,4-Triazol-4-yl, l,2,4-Oxadiazol-3-yl, 1,2,4- Oxadiazol-5-yl, l,3,4-Oxadiazol-2-yl, l,2,3-Oxadiazol-4-yl, l,2,3-Oxadiazol-5-yl, l,2,5-Oxadiazol-3-yl, Azepinyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyrazin-3-yl, Pyrimidin-2-yl, 4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, lH-l, 2,3-triazol-l-yl, lH-l, 2,3-triazol-4-yl, lH-l, 2,3-triazol-5-yl, 2H-l, 2,3-triazol-2-yl, 2H-l, 2,3-triazol-4-yl, lH-l, 2,4-triazol-l-yl, lH-l, 2,4- Triazol-3-yl, 4H-l, 2,4-triazol-4-yl, l, 2,4-oxadiazol-3-yl, 1,2,4-oxadiazol-5-yl, l, 3,4- Oxadiazol-2-yl, l, 2,3-oxadiazol-4-yl, l, 2,3-oxadiazol-5-yl, l, 2,5-oxadiazol-3-yl, azepinyl, pyridin-2-yl, Pyridin-3-yl, pyridin-4-yl, pyrazin-2-yl, pyrazin-3-yl, pyrimidin-2-yl,
Pyrimidin-4-yl, Pyrimidin-5-yl, Pyridazin-3-yl, Pyridazin-4-yl, l,3,5-Triazin-2-yl, l,2,4-Triazin-3-yl, l,2,4-Triazin-5-yl, 1 ,2,4-Triazin-6-yl, l,2,3-Triazin-4-yl, l,2,3-Triazin-5-yl, 1,2,4-, 1,3,2-, 1,3,6- und l,2,6-Oxazinyl, Isoxazol-3-yl, Isoxazol-4-yl, Isoxazol-5-yl, l,3-Oxazol-2-yl, l,3-Oxazol-4-yl, 1,3- Oxazol-5-yl, Isothiazol-3-yl, Isothiazol-4-yl, Isothiazol-5-yl, l,3-Thiazol-2-yl, l,3-Thiazol-4-yl, 1,3- Thiazol-5-yl, Oxepinyl, Thiepinyl, 1 ,2,4-Triazolonyl und 1 ,2,4-Diazepinyl, 2H-l,2,3,4-Tetrazol-5-yl, lH-l,2,3,4-Tetrazol-5-yl, l,2,3,4-Oxatriazol-5-yl, l,2,3,4-Thiatriazol-5-yl, l,2,3,5-Oxatriazol-4-yl, l,2,3,5-Thiatriazol-4-yl. Die erfindungsgemäßen Heteroarylgruppen können ferner mit einem oder mehreren, gleichen oder verschiedenen Resten substituiert sein. Sind zwei benachbarte Pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-3-yl, pyridazin-4-yl, l, 3,5-triazin-2-yl, l, 2,4-triazin-3-yl, l, 2,4-triazin-5-yl, 1, 2,4-triazin-6-yl, l, 2,3-triazin-4-yl, l, 2,3-triazin-5-yl, 1,2, 4-, 1,3,2-, 1,3,6- and l, 2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, l, 3-oxazol-2 -yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, 1,3-thiazol-2-yl , l, 3-thiazol-4-yl, 1,3-thiazol-5-yl, oxepinyl, thiepinyl, 1, 2,4-triazolonyl and 1, 2,4-diazepinyl, 2H-l, 2,3,4 -Tetrazol-5-yl, lH-l, 2,3,4-tetrazol-5-yl, l, 2,3,4-oxatriazol-5-yl, l, 2,3,4-thiatriazol-5-yl , l, 2,3,5-oxatriazol-4-yl, l, 2,3,5-thiatriazol-4-yl. The heteroaryl groups according to the invention can furthermore be substituted by one or more, identical or different radicals. Are two neighboring
Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Carbon atoms are part of a further aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
Bevorzugt sind beispielsweise Chinoline (z. B. Chinolin-2-yl, Chinolin-3-yl, Chinolin-4-yl, Chinolin-5- yl, Chinolin-6-yl, Chinolin-7-yl, Chinolin-8-yl); Isochinoline (z. B. Isochinolin- l-yl, Isochinolin-3-yl, Isochinolin-4-yl, Isochinolin-5-yl, Isochinolin-6-yl, Isochinolin-7-yl, Isochinolin-8-yl); Chinoxalin; Chinazolin; Cinnolin; l,5-Naphthyridin; l,6-Naphthyridin; l,7-Naphthyridin; l,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe lH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofuran-2-yl, l-Benzofuran-3-yl, l-Benzofuran-4-yl, l-Benzofuran-5- yl, l-Benzofuran-6-yl, l-Benzofuran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, lH-Indazol-For example, quinolines (e.g. quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl ); Isoquinolines (e.g. isoquinolin-l-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; quinazoline; cinnoline; l, 5-naphthyridine; l, 6-naphthyridine; l, 7-naphthyridine; l, 8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine; pyridopyrimidines; Pyridopyridazine; pteridines; Pyrimidopyrimidine. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group lH-indol-l-yl, lH-indol-2-yl, lH-indol-3-yl, lH-indol-4-yl, lH- Indol-5-yl, 1H- Indol-6-yl, lH-indol-7-yl, l-benzofuran-2-yl, l-benzofuran-3-yl, l-benzofuran-4-yl, l-benzofuran-5-yl, l-benzofuran 6-yl, l-benzofuran-7-yl, l-benzothiophene-2-yl, l-benzothiophene-3-yl, 1-benzothiophene-4-yl, l-benzothiophene-5-yl, l-benzothiophene-6- yl, l-benzothiophene-7-yl, lH-indazole
1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazole
2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H- Isoindol-2-yl, 2H-Isoindol-l-yl, 2H-Isoindol-3-yl, 2H-Isoindol-4-yl, 2H-Isoindol-5-yl, 2H-Isoindol-6-yl; 2H-Isoindol-7-yl, lH-Benzimidazol-l-yl, lH-Benzimidazol-2-yl, lH-Benzimidazol-4-yl, 1H- Benzimidazol-5-yl, lH-Benzimidazol-6-yl, lH-Benzimidazol-7-yl, l,3-Benzoxazol-2-yl, 1,3- Benzoxazol-4-yl, l,3-Benzoxazol-5-yl, l,3-Benzoxazol-6-yl, l,3-Benzoxazol-7-yl, l,3-Benzthiazol-2-yl, l,3-Benzthiazol-4-yl, l,3-Benzthiazol-5-yl, l,3-Benzthiazol-6-yl, l,3-Benzthiazol-7-yl, 1,2- Benzisoxazol-3-yl, l,2-Benzisoxazol-4-yl, l,2-Benzisoxazol-5-yl, l,2-Benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l,2-Benzisothiazol-3-yl, l,2-Benzisothiazol-4-yl, l,2-Benzisothiazol-5-yl, 1,2- Benzisothiazol-6-yl, l,2-Benzisothiazol-7-yl. 2-yl, 2H-indazol-3-yl, 2H-indazol-4-yl, 2H-indazol-5-yl, 2H-indazol-6-yl, 2H-indazol-7-yl, 2H-isoindol-2- yl, 2H-isoindol-1-yl, 2H-isoindol-3-yl, 2H-isoindol-4-yl, 2H-isoindol-5-yl, 2H-isoindol-6-yl; 2H-isoindol-7-yl, 1H-benzimidazol-1-yl, 1H-benzimidazol-2-yl, 1H-benzimidazol-4-yl, 1H-benzimidazol-5-yl, 1H-benzimidazol-6-yl, 1H- Benzimidazol-7-yl, l, 3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, l, 3-benzoxazol-5-yl, l, 3-benzoxazol-6-yl, l, 3- Benzoxazol-7-yl, l, 3-benzothiazol-2-yl, l, 3-benzothiazol-4-yl, l, 3-benzothiazol-5-yl, l, 3-benzothiazol-6-yl, l, 3- Benzothiazol-7-yl, 1,2-benzisoxazol-3-yl, 1,2-benzisoxazol-4-yl, 1,2-benzisoxazol-5-yl, 1,2-benzisoxazol-6-yl, 1,2- Benzisoxazol-7-yl, l, 2-benzisothiazol-3-yl, l, 2-benzisothiazol-4-yl, l, 2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, l, 2- benzisothiazol-7-yl.
Die Bezeichnung "Halogen" bedeutet Fluor, Chlor, Brom oder Iod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" ein Fluor-, Chlor-, Brom- oder Iodatom. The term "halogen" means fluorine, chlorine, bromine or iodine. If the term is used for a radical, "halogen" means a fluorine, chlorine, bromine or iodine atom.
Erfindungsgemäß bedeutet„Alkyl“ einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als „substituiertes Alkyl“ bezeichnet wird. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder Iod. Die Vorsilbe„Bis“ schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl(Methyl). According to the invention, “alkyl” means a straight-chain or branched open-chain, saturated hydrocarbon radical which is optionally substituted one or more times and is referred to in the latter case as “substituted alkyl”. Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups; methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine are particularly preferred. The prefix "bis" also includes the combination of different alkyl residues, e.g. B. methyl (ethyl) or ethyl (methyl).
„Haloalkyl“, ,,-alkenyl“ und ,,-alkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl "Haloalkyl", "- alkenyl" and "- alkynyl" mean alkyl or alkenyl or alkynyl which is partially or completely substituted by identical or different halogen atoms, e.g. monohaloalkyl
(= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z.(= Monohalogenalkyl) such as B. CH 2 CH 2 CI, CH 2 CH 2 Br, CHCICH 3 , CH 2 CI, CH 2 F; Perhaloalkyl such as
B. CCI3, CCIF2, CFC12,CF2CC1F2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. B. CCI3, CCIF 2, CFC1 2 , CF 2 CC1F 2, CF 2 CCIFCF3; Polyhaloalkyl such as B. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3 ; The term perhaloalkyl also includes the term perfluoroalkyl.
„Teilfluoriertes Alkyl“ bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der einfach oder mehrfach durch Fluor substituiert ist, wobei sich die entsprechenden Fluoratome als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden können, wie z. B. CHFCH3, CH2CH2F, CH2CH2CF3, CHF2, CH2F, CHFCF2CF3 “Partially fluorinated alkyl” means a straight-chain or branched, saturated hydrocarbon which is mono- or polysubstituted by fluorine, and the corresponding fluorine atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, such as, for example, B. CHFCH 3 , CH 2 CH 2 F, CH 2 CH 2 CF 3 , CHF 2 , CH 2 F, CHFCF 2 CF 3
„Teilfluoriertes Haloalkyl“ bedeutet einen geradkettigen oder verzweigten, gesättigten Kohlenwasserstoff, der durch verschiedenene Halogenatomen mit mindestens einem Fluoratom substituiert ist, wobei alle anderen gegebenenfalls vorhandenen Halogenatome ausgewählt sind aus der Gruppe Fluor, Chlor oder Brom, Iod. Die entsprechenden Halogenatome können sich dabei als Substituenten an einem oder mehreren verschiedenen Kohlenstoffatomen der geradkettigen oder verzweigten Kohlenwasserstoffkette befinden. Teilfluoriertes Haloalkyl schließt auch die vollständige Substitution der geradkettigen oder verzweigten Kette durch Halogen unter Beteiligung von mindestens einem Fluoratom ein. “Partially fluorinated haloalkyl” means a straight-chain or branched, saturated Hydrocarbon which is substituted by different halogen atoms with at least one fluorine atom, all other halogen atoms which may be present being selected from the group consisting of fluorine, chlorine or bromine, iodine. The corresponding halogen atoms can be located as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain. Partially fluorinated haloalkyl also includes the complete substitution of the straight-chain or branched chain by halogen with the participation of at least one fluorine atom.
„Haloalkoxy“ ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. “Haloalkoxy” is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 CI; The same applies to haloalkenyl and other halogen-substituted radicals.
Der hier beispielhaft genannte Ausdruck "(Ci-C4)-Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The expression "(Ci-C4) -alkyl" mentioned here by way of example means a shorthand notation for straight-chain or branched alkyl having one to 4 carbon atoms corresponding to the
Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1 -Propyl, 2-Propyl, 1 -Butyl, 2-Butyl, 2-Methylpropyl oder tert-Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C-Atomen, z. B. "(Ci-C6)-Alkyl", umfassen entsprechend auch geradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen. Range specification for carbon atoms, ie includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals with a larger specified range of carbon atoms, e.g. B. "(Ci-C 6 ) alkyl", also include straight-chain or branched alkyl radicals with a larger number of carbon atoms, ie, according to the example, also the alkyl radicals with 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und l,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in composite radicals, are the lower carbon skeletons, e.g. with 1 to 6 carbon atoms or in the case of unsaturated groups with 2 to 6 carbon atoms, preferred. Alkyl radicals, also in the composite radicals such as alkoxy, haloalkyl etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, at least one double bond or triple bond being present. Residues with a double bond or
Dreifachbindung. Triple bond.
Der Begriff„Alkenyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkenyl” also includes straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie l,3-Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (l,2-Propadienyl), 1 ,2-Butadienyl und l,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-C6)- Alkenyl wie Ethenyl, l-Propenyl, 2-Propenyl, 1 -Methylethenyl, l-Butenyl, 2-Butenyl, 3- Butenyl, 1 -Methyl- l-propenyl, 2-Methyl- l-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1- Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- l-butenyl, 2-Methyl- l-butenyl, 3 -Methyl- 1- butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3- butenyl, 3 -Methyl-3 -butenyl, 1 , 1 -Dimethyl-2-propenyl, l,2-Dimethyl-l-propenyl, 1 ,2-Dimethyl-2- propenyl, l-Ethyl-l-propenyl, 1 -Ethyl-2-propenyl, l-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- l-pentenyl, 2-Methyl-l-pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-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, l,2-Dimethyl-l -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3 -butenyl, l,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2, 2-Dimethyl-3 -butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l-butenyl, 3,3-Dimethyl-2- butenyl, l-Ethyl-l -butenyl, l-Ethy 1-2 -butenyl, l-Ethyl- 3 -butenyl, 2-Ethyl-l -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. Hydrocarbon radicals with more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals with one or more cumulative double bonds, such as, for example, allenyl (1,2-propadienyl), 1,1 2-butadienyl and l, 2,3-pentatrienyl. Alkenyl means, for example, vinyl, which can optionally be substituted by further alkyl radicals, for example (but not limited to) (C2-C6) alkenyl such as ethenyl, l-propenyl, 2-propenyl, 1-methylethenyl, l-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, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, l, 2-dimethyl-l-propenyl, 1, 2-dimethyl-2-propenyl, l-ethyl-l-propenyl, 1-ethyl-2-propenyl, l-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, l-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 l-butenyl, l, 3-dimethyl-2-butenyl, l, 3-dimethyl-3-butenyl, 2, 2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3-dimethyl 2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-bu tenyl, l-ethyl-1-butenyl, l-ethyl 1-2 -butenyl, l-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 and 1-ethyl-2-methyl-2-propenyl.
Der Begriff„Alkinyl“ schließt insbesondere auch geradkettige oder verzweigte offenkettige The term “alkynyl” also includes straight-chain or branched open-chain ones
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Hydrocarbon residues with more than one triple bond or with one or more
Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise l,3-Butatrienyl bzw. 3-Penten-l-in-l-yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, l-Propinyl, 2-Propinyl, l-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, l-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2- butinyl, 1 -Methyl-3 -butinyl, 2-Methyl-3-butinyl, 3 -Methyl- l-butinyl, 1 , 1 -Dimethyl-2-propinyl, l-Ethyl- 2-propinyl, l-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, l-Methyl-3- pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3 -Methyl- l-pentinyl, 3- Methyl-4-pentinyl, 4-Methyl- l-pentinyl, 4-Methyl-2-pentinyl, 1 , 1 -Di-methyl-2-butinyl, l,l-Dimethyl-3- butinyl, 1 ,2-Dimethyl-3 -butinyl, 2, 2-Dimethyl-3 -butinyl, 3, 3 -Dimethyl- l-butinyl, 1 -Ethyl-2-butinyl, 1- Ethyl-3 -butinyl, 2-Ethyl-3 -butinyl und 1 -Ethyl- 1 -methyl-2-propinyl. Triple bonds and one or more double bonds, such as 1, 3-butatrienyl or 3-penten-l-in-l-yl. (C2-C6) alkynyl means e.g. Ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, l-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, l-methyl- 2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, l-ethyl-2-propynyl, l-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2- Methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-di-methyl-2-butynyl, l, l-dimethyl-3-butynyl, 1, 2-dimethyl-3-butynyl, 2, 2-dimethyl-3-butynyl, 3, 3-dimethyl-l-butynyl, 1-ethyl-2-butynyl, 1- Ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl.
Der Begriff„Cycloalkyl“ bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl, das gegebenenfalls weiter substituiert ist, bevorzugt durch Wasserstoff, Alkyl, Alkoxy, Cyano, Nitro, Alkylthio, Haloalkylthio, Halogen, Alkenyl, Alkinyl, Haloalkyl, Amino, Alkylamino, Bisalkylamino, Alkocycarbonyl, The term "cycloalkyl" means a carbocyclic, saturated ring system with preferably 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, which is optionally further substituted, preferably by hydrogen, alkyl, alkoxy, cyano, nitro, alkylthio, haloalkylthio, halogen, alkenyl, alkynyl, haloalkyl, amino, alkylamino, bisalkylamino, alkocycarbonyl,
Hydroxycarbonyl, Arylalkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl,
Cycloalkylaminocarbonyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am  Cycloalkylaminocarbonyl. In the case of optionally substituted cycloalkyl, cyclic systems with substituents are included, substituents also having a double bond on
Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfasst, wie beispielsweise Bicyclo[l .1.0]butan-l -yl, Bicyclo[l .1 0]butan-2-yl, Bicyclo[2.1.0]pentan-l -yl, Bicyclo[l .1.1 ]pentan-l - yl, Bicyclo[2.l.0]pentan-2-yl, Bicyclo[2.l.0]pentan-5-yl, Bicyclo[2.l.l]hexyl, Bicyclo[2.2.l]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.l]octan-2-yl, Bicyclo[3.2.2]nonan-2-yl, Adamantan-l-yl und Adamantan-2-yl, aber auch Systeme wie z. B. l,l'-Bi(cyclopropyl)-l-yl, l,l'-Bi(cyclopropyl)-2-yl. Der Ausdruck "(C3-C7)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Cycloalkyl radical, e.g. B. an alkylidene group such as methylidene are included. In the case of optionally substituted cycloalkyl, multi-cyclic aliphatic systems are also included, such as, for example, bicyclo [1.0] butan-1-yl, bicyclo [1.0] butan-2-yl, bicyclo [2.1.0] pentan-1 - yl, bicyclo [l. 1.1] pentan-1-yl, bicyclo [2.l.0] pentan-2-yl, bicyclo [2.l.0] pentan-5-yl, bicyclo [2.ll] hexyl, bicyclo [2.2.l] hept-2-yl, Bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.l] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-l-yl and adamantan-2-yl, but also Systems such as B. l, l'-Bi (cyclopropyl) -l-yl, l, l'-Bi (cyclopropyl) -2-yl. The term "(C3-C7) cycloalkyl" means a shorthand notation for cycloalkyl of three to seven
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. lm Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfasst, wie beispielsweise Spiro[2.2]pent-l-yl, Spiro[2.3]hex-l-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl,Carbon atoms according to the range for carbon atoms. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as, for example, spiro [2.2] pent-l-yl, spiro [2.3] hex-l-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl,
Spiro [3.3 ]hept- 1 -yl, Spiro[3.3 ]hept-2-yl. Spiro [3.3] hept-1-yl, Spiro [3.3] hept-2-yl.
„Cycloalkenyl“ bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1 -Cyclobutenyl, 2-Cyclobutenyl, 1 -Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1 -Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind lm Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. "Cycloalkenyl" means a carbocyclic, non-aromatic, partially unsaturated ring system with preferably 4-8 C atoms, e.g. 1-Cyclobutenyl, 2-Cyclobutenyl, 1-Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, or 1-Cyclohexenyl, 2-Cyclohexenyl, 3-Cyclohexenyl, l, 3-Cyclohexadienyl or 1, 4-Cyclohexadienyl, whereby also substituents with a Double bond on the cycloalkenyl radical, e.g. B. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply accordingly.
Der Begriff„Alkyliden“, z. B. auch in der Form (Ci-Cio)-Alkyliden, bedeutet den Rest eines geradkettigen oder verzweigten offenkettigen Kohlenwasserstoffrests, der über eine Zweifachbindung gebunden ist. Als Bindungsstelle für Alkyliden kommen naturgemäß nur Positionen am Grundkörper in Frage, an denen zwei H- Atome durch die Doppelbindung ersetzt werden können; Reste sind z. B. =CFb, =CH-CH3, =C(CFb)-CF[3, =C(CH3)-C2H5 oder =C(C'2FF)-C2FF. Cycloalkyliden bedeutet ein The term "alkylidene", e.g. B. also in the form (Ci-Cio) alkylidene, means the remainder of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond. As a binding site for alkylidene there are naturally only positions on the base in which two H atoms can be replaced by the double bond; Leftovers are e.g. B. = CFb, = CH-CH 3 , = C (CFb) -CF [ 3 , = C (CH 3 ) -C 2 H 5 or = C (C ' 2FF) -C2FF . Cycloalkylidene means a
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. carbocyclic radical which is bonded via a double bond.
„Cycloalkylalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylalkylrest und „Arylalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Arylalkylrest. “Cycloalkylalkyloxy” means a cycloalkylalkyl radical bonded via an oxygen atom and “arylalkyloxy” means an arylalkyl radical bonded via an oxygen atom.
„Alkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkoxyrest und„Alkoxyalkoxy“ bedeutet einen über ein Sauerstoffatom gebundenen Alkoxyalkylrest, z.B. (aber nicht beschränkt auf) Methoxymethoxy, Methoxyethoxy, Ethoxyethoxy, Methoxy-n-propyloxy. "Alkoxyalkyl" stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy" means an alkoxyalkyl radical bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy.
„Alkylthioalkyl“ steht für einen über eine Alkylgruppe gebundenen Alkylthiorest und “Alkylthioalkyl” stands for an alkylthio radical bonded via an alkyl group and
„Alkylthioalkylthio“ bedeutet einen über ein Sauerstoffatom gebundenen Alkylthioalkylrest. “Alkylthioalkylthio” means an alkylthioalkyl radical bonded via an oxygen atom.
„Arylalkoxyalkyl“ steht für einen über eine Alkylgruppe gebundenen Aryloxyrest und "Arylalkoxyalkyl" stands for an aryloxy radical bonded via an alkyl group and
„Heteroaryloxyalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heteroaryloxyrest. „Haloalkoxyalkyl“ steht für einen gebundenen Haloalkoxyrest und„Haloalkylthioalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. “Heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group. “Haloalkoxyalkyl” stands for a bound haloalkoxy radical and “Haloalkylthioalkyl” means a haloalkylthio radical bound via an alkyl group.
„Arylalkyl“ steht für einen über eine Alkylgruppe gebundenen Arylrest,„Heteroarylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Heterocyclylrest. “Arylalkyl” stands for an aryl radical bonded via an alkyl group, “heteroarylalkyl” means a heteroaryl radical bonded via an alkyl group, and “heterocyclylalkyl” means a heterocyclyl radical bonded via an alkyl group.
„Cycloalkylalkyl“ steht für einen über eine Alkylgruppe gebundenen Cycloalkylrest, z. B. (aber nicht beschränkt auf) Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, 1 - Cyclopropyleth-l -yl, 2-Cyclopropyleth-l-yl, l-Cyclopropylprop-l-yl, 3-Cyclopropylprop-l-yl. “Cycloalkylalkyl” stands for a cycloalkyl radical bonded via an alkyl group, eg. B. (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1 - cyclopropyleth-l -yl, 2-cyclopropyleth-l-yl, l-cyclopropylprop-l-yl, 3-cyclopropylprop-l-yl.
„Arylalkenyl“ steht für einen über eine Alkenylgruppe gebundenen Arylrest,„Heteroarylalkenyl“ bedeutet einen über eine Alkenylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkenyl“ bedeutet einen über eine Alkenylgruppe gebundenen Heterocyclylrest. “Arylalkenyl” stands for an aryl radical bonded via an alkenyl group, “heteroarylalkenyl” means a heteroaryl radical bonded via an alkenyl group, and “heterocyclylalkenyl” means a heterocyclyl radical bonded via an alkenyl group.
„Arylalkinyl“ steht für einen über eine Alkinylgruppe gebundenen Arylrest,„Heteroarylalkinyl“ bedeutet einen über eine Alkinylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkinyl“ bedeutet einen über eine Alkinylgruppe gebundenen Heterocyclylrest. “Arylalkynyl” stands for an aryl group bonded via an alkynyl group, “heteroarylalkynyl” means a heteroaryl group bonded via an alkynyl group, and “heterocyclylalkynyl” means a heterocyclyl group bonded via an alkynyl group.
Erfindungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradketiges oder verzweigtes S -Halogenalkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "haloalkylthio" - alone or as part of a chemical group - stands for straight-chain or branched S -haloalkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cs)-, (C' i-G,)- oder (Ci-C4)-Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l-ylthio, 2,2,2-Difluoreth-l- ylthio, 3,3,3-prop-l-ylthio. Carbon atoms, such as (Ci-Cs) -, (C ' iG,) - or (Ci-C4) -haloalkylthio, for example (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2 , 2,2-difluoroeth-l-ylthio, 3,3,3-prop-l-ylthio.
„Halocycloalkyl“ und„Halocycloalkenyl“ bedeuten durch gleiche oder verschiedene Halogenatome, wie z. B. F, CI und Br, oder durch Haloalkyl, wie z. B. Trifluormethyl oder Difluormethyl teilweise oder vollständig substituiertes Cycloalkyl oder Cycloalkenyl , z.B. l-Fluorcycloprop-l-yl, 2-Fluorcycloprop- l-yl, 2,2-Difluorcycloprop-l-yl, l-Fluorcyclobut-l-yl, l-Trifluormethylcycloprop-l-yl, 2- Trifluormethylcycloprop- 1 -yl, 1 -Chlor-cycloprop- 1 -yl, 2-Chlorcycloprop- 1 -yl, 2,2-Dichlorcycloprop- 1 - yl, 3,3-Difluorcyclobutyl. "Halocycloalkyl" and "Halocycloalkenyl" mean by identical or different halogen atoms, such as. B. F, CI and Br, or by haloalkyl, such as. B. trifluoromethyl or difluoromethyl partially or fully substituted cycloalkyl or cycloalkenyl, e.g. l-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 2,2-difluorocycloprop-l-yl, l-fluorocyclobut-l-yl, l-trifluoromethylcycloprop-l-yl, 2-trifluoromethylcycloprop-1-yl, 1-chloro-cycloprop-1-yl, 2-chlorocycloprop-1-yl, 2,2-dichlorocycloprop-1-yl, 3,3-difluorocyclobutyl.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (1) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der allgemeinen Formel (1) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der Verbindung der allgemeinen Formel (I) umfasst werden. If the compounds can form tautomers by hydrogen shift which would not be structurally formally covered by the general formula (1), these tautomers are nevertheless included in the definition of the compounds of the general formula (1) according to the invention, unless a specific tautomer is the subject of consideration is. For example, many Carbonyl compounds are present both in the keto form and in the enol form, both forms being encompassed by the definition of the compound of the general formula (I).
Die Verbindungen der allgemeinen Formel (I) können je nach Art und Verknüpfung der Substituenten als Stereoisomere vorliegen. Die durch ihre spezifische Raumform definierten möglichen Stereoisomere, wie Enantiomere, Diastereomere, Z- und E-Isomere sind alle von der allgemeinen Formel (I) umfasst. Sind beispielsweise eine oder mehrere Alkenylgruppen vorhanden, so können Diastereomere (Z- und E- Isomere) auftreten. Sind beispielsweise ein oder mehrere asymmetrische Kohlenstoffatome vorhanden, so können Enantiomere und Diastereomere auftreten. Stereoisomere lassen sich aus den bei der Depending on the nature and linkage of the substituents, the compounds of the general formula (I) can be present as stereoisomers. The possible stereoisomers defined by their specific spatial shape, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the general formula (I). For example, if one or more alkenyl groups are present, diastereomers (Z and E isomers) can occur. For example, if one or more asymmetric carbon atoms are present, enantiomers and diastereomers can occur. Stereoisomers can be derived from the at
Herstellung anfallenden Gemischen nach üblichen Trennmethoden erhalten. Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. des Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Ebenso können Stereoisomere durch Einsatz stereoselektiver Reaktionen unter Verwendung optisch aktiver Ausgangs- und/oder Hilfsstoffe selektiv hergestellt werden. Die Erfindung betrifft somit auch alle Stereoisomere, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. Im Folgenden wird der Einfachheit halber jedoch stets von Verbindungen der allgemeinen Formel (I) gesprochen, obwohl sowohl die reinen Verbindungen als gegebenenfalls auch Gemische mit unterschiedlichen Anteilen an isomeren Verbindungen gemeint sind. Obtaining mixtures obtained by conventional separation methods. The chromatographic separation can be carried out on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the production of test samples for biological testing. Likewise, stereoisomers can be produced selectively by using stereoselective reactions using optically active starting materials and / or auxiliary substances. The invention thus also relates to all stereoisomers which are encompassed by the general formula (I) but are not specified with their specific stereoform, and to mixtures thereof. For the sake of simplicity, however, the following always refers to compounds of the general formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the cleaning can also be carried out by
Umkristallisieren oder Digerieren erfolgen. Sofern einzelne Verbindungen der allgemeinen Formel (I) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen der allgemeinen Formel (I) hergestellt werden. Recrystallize or digest. If individual compounds of the general formula (I) are not satisfactorily accessible in the ways described below, they can be prepared by derivatizing other compounds of the general formula (I).
Als Isolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der allgemeinen Formel (I) kommen Methoden in Frage, die dem Fachmann aus analogen Fällen allgemein bekannt sind, z.B. durch physikalische Verfahren wie Kristallisation, Chromatographieverfahren, vor allem Säulenchromatographie und HPLC (Hochdruckflüssigchromatographie), Destillation, gegebenenfalls unter reduziertem Druck, Extraktion und andere Verfahren, können gegebenfalls verbleibende Gemische in der Regel durch chromatographische Trennung, z.B. an chiralen Festphasen, getrennt werden. Für präparative Mengen oder im industriellen Maßstab kommen Verfahren in Frage wie Kristallisation, z.B. diastereomerer Salze, die aus den Diastereomerengemischen mit optisch aktiven Säuren und gegebenenfalls bei vorhandenen sauren Gruppen mit optisch aktiven Basen erhalten werden können. Synthese von substituierten Heterocyclylpyrrolonen der allgemeinen Formel (I). Methods which are generally known to the person skilled in the art from analogous cases, for example by physical processes such as crystallization, chromatography processes, especially column chromatography and HPLC (high pressure liquid chromatography), and distillation are suitable as isolation, purification and stereoisomer separation processes for compounds of the general formula (I) If necessary, under reduced pressure, extraction and other methods, any remaining mixtures can generally be separated by chromatographic separation, for example on chiral solid phases. For preparative amounts or on an industrial scale, processes such as crystallization, for example diastereomeric salts, can be used, which can be obtained from the diastereomer mixtures with optically active acids and, if appropriate, with acidic groups present with optically active bases. Synthesis of substituted heterocyclylpyrrolones of the general formula (I).
Figure imgf000041_0001
Die erfindungsgemäßen substituierten Heterocyclylpyrrolone der allgemeinen Formel (I) können ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten
Figure imgf000041_0001
The substituted heterocyclylpyrrolones of the general formula (I) according to the invention can be prepared starting from known processes. The used and examined
Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren teilgesättigten heterocyclischen Aminen und von entsprechend substituierten Furanonen oder Furandionen aus. Die Gruppierungen Q, X, Y, R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 R13, R14, R15 und R16 der allgemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten Bedeutungen, . Synthesis routes are based on commercially available or easily prepared partially saturated heterocyclic amines and on appropriately substituted furanones or furandions. The groupings Q, X, Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 R 13 , R 14 , R 15 and R 16 of the general formula (I) have the meanings defined above in the diagrams below.
Als erstes Schlüsselintermediat für die Synthese der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) wird ein gegebenenfalls weiter substituiertes heterocyclisches Amin Q-NFb (IV) hergestellt. Beispielhaft, aber nicht einschränkend wird dies an der Synthese eines gegebenenfalls weiter substituierten 2-Amino-isoxazolins (IVa) gezeigt. Dazu wird in einer Olefinierungsreaktion ein Aldehyd bzw. Keton (II) mit Diethyl-(cyanomethyl)phosphonat in das entsprechende substituierte Nitril (III) umgesetzt und durch Reaktion mit V-Hydroxycarbamid unter Verwendung einer geeigneten Base (z. B. NaOMe) in das gewünschte substituierte heterocyclische Amin Q-NFb (IV) überführt (vgl. Bioorg. Med. Chem. 2003, 11, 4093; Bull. Chim. Soc. France 1973, 1138). Im nachfolgenden Schema 1 steht R6 und R7 beispielhaft, aber nicht einschränkend für Wasserstoff, und R4 und R5 haben die zuvor definierte Bedeutung. An optionally further substituted heterocyclic amine Q-NFb (IV) is prepared as the first key intermediate for the synthesis of the compounds of the general formula (I) according to the invention. This is shown by way of example, but not by way of limitation, in the synthesis of an optionally further substituted 2-amino-isoxazoline (IVa). For this purpose, an aldehyde or ketone (II) is reacted with diethyl (cyanomethyl) phosphonate in the corresponding substituted nitrile (III) in an olefinization reaction and into the by reaction with V-hydroxycarbamide using a suitable base (e.g. NaOMe) desired substituted heterocyclic amine Q-NFb (IV) transferred (see. Bioorg. Med. Chem. 2003, 11, 4093; Bull. Chim. Soc. France 1973, 1138). In scheme 1 below, R 6 and R 7 are exemplary but not restrictive of hydrogen, and R 4 and R 5 have the meaning previously defined.
Figure imgf000041_0002
Figure imgf000041_0002
(II) (III) (IVa)  (II) (III) (IVa)
Schema 1  Scheme 1
Die monosubstituierte Furan-2,5-dione (VI), die auch als Maleinsäureanhydride bezeichnet werden, können über literaturbekannte Syntheseorschriften hergestellt werden (vgl. J. Chem. Soc., Perkin Trans. 1, 1982, 215; EP1426365; J. Org. Chem. 1998, 63, 2646; WO2015/018431; Tetrahedron 2012, 68, 5863; Russian J. Org. Chem. 2007, 43, 801), beispielsweise Verbindungen (VI- 1) und (VI-2) im nachfolgenden Schema 2 in mehreren Schritten aus einem geeigneten Acetylendicarbonsäureester (V). The monosubstituted furan-2,5-diones (VI), which are also referred to as maleic anhydrides, can be prepared via synthesis instructions known from the literature (cf. J. Chem. Soc., Perkin Trans. 1, 1982, 215; EP1426365; J. Org Chem. 1998, 63, 2646; WO2015 / 018431; Tetrahedron 2012, 68, 5863; Russian J. Org. Chem. 2007, 43, 801), for example compounds (VI-1) and (VI-2) in the following scheme 2 in several steps from a suitable acetylenedicarboxylic acid ester (V).
Figure imgf000042_0001
Figure imgf000042_0001
Schema 2 Scheme 2
Substituierte Heterocyclylpyrrolone der allgemeinen Formel (I) können in zwei Schritten durch Substituted heterocyclylpyrrolone of the general formula (I) can in two steps
Umsetzung eines geeigneten gegebenenfalls substituierten teilgesättigten Heterocyclylamins Q-NFh (IV) mit einem geeigneten gegebenenfalls weiter substituierten Maleinsäureanhydrid (VI) unter Verwendung einer geeigneten Base (z. B. Pyridin) in einem geeigneten polar-aprotischen Lösemittel (z. B. Acetonitril) oder unter sauren Bedingungen unter Verwendung einer geeigneten Säure (z. B. Reaction of a suitable optionally substituted partially saturated heterocyclylamine Q-NFh (IV) with a suitable optionally further substituted maleic anhydride (VI) using a suitable base (e.g. pyridine) in a suitable polar aprotic solvent (e.g. acetonitrile) or under acidic conditions using a suitable acid (e.g.
Essigsäure oder p-Toluolsulfonsäure in Toluol als Lösemittel) und nachfolgende Reduktion einer Carbonylgruppe des gebildeten substituierten Maleinsäureimids (VII) hergestellt werden. Die Reduktion läßt sich in einem geeigneten Lösemittel (z. B. Tetrahydrofuran und Methanol) mit Hilfe eines geeigneten Reduktionsmittels vornehmen und kann zu Regioisomeren (VIII) führen. Als Acetic acid or p-toluenesulfonic acid in toluene as solvent) and subsequent reduction of a carbonyl group of the substituted maleimide (VII) formed. The reduction can be carried out in a suitable solvent (e.g. tetrahydrofuran and methanol) with the aid of a suitable reducing agent and can lead to regioisomers (VIII). As
Reduktionsmittel kommen beispielsweise Natriumhydrid, Lithiumaluminiumhydrid, Natriumborhydrid oder andere Wasserstoff entwickelnde Metallhydride in Frage. Es kann alternativ auch eine  Reducing agents are, for example, sodium hydride, lithium aluminum hydride, sodium borohydride or other hydrogen-generating metal hydrides. Alternatively, it can be one
Übergangsmetall- vermittelte Hydrierung durchgeführt werden (vgl. CH633678, DE2247266, Transition metal-mediated hydrogenation can be carried out (cf. CH633678, DE2247266,
WO2015/018434). Die Reduktion der Carbonylgruppe kann Gemische von Regioisomeren liefern, daher sind im nachfolgenden Schema 3 beide möglichen Regioisomere abgebildet, um dies zu verdeutlichen. Im nachfolgenden Schema 3 haben X, Y und Q die zuvor definierten Bedeutungen, R2 steht beispielhaft, aber nicht einschränkend für OH und R3 steht beispielhaft, aber nicht einschränkend, für Wasserstoff.
Figure imgf000043_0003
o Y WO2015 / 018434). The reduction of the carbonyl group can provide mixtures of regioisomers, so both possible regioisomers are shown in Scheme 3 below to illustrate this. In Scheme 3 below, X, Y and Q have the meanings defined above, R 2 is exemplary but not restrictive of OH and R 3 is exemplary but not restrictive of hydrogen.
Figure imgf000043_0003
o Y
II N— Q
Figure imgf000043_0001
II N - Q
Figure imgf000043_0001
Schema 3  Scheme 3
Alternativ können substituierte Heterocyclylpyrrolone der allgemeinen Formel (la) ausgehend von der Umsetzung eines Hydroxy- oder Bromolactons (IX) mit einem geeigneten gegebenenfalls substituierten teilgesättigten Heterocyclylamins Q-NH2 (IV) in einem geeigneten Lösemittel (z. B. Toluol) bei erhöhter Temperatur hergestellt werden. Durch weitere Reaktion des resultierenden lntermediates (X) mit Essigsäureanhydrid unter Verwendung einer geeigneten Base (z. B. Pyridin) bei erhöhter Alternatively, substituted heterocyclylpyrrolones of the general formula (Ia) can be prepared starting from the reaction of a hydroxy- or bromolactone (IX) with a suitable, optionally substituted, partially saturated heterocyclylamine Q-NH2 (IV) in a suitable solvent (for example toluene) at elevated temperature become. By further reaction of the resulting intermediate (X) with acetic anhydride using a suitable base (e.g. pyridine) at elevated
Temperatur wird das substituierte Heterocyclylpyrrolon der allgemeinen Formel (XI) mit O- Acetylgruppe gebildet, das durch Erhitzen unter sauren Bedingungen (z. B. in einem Gemisch ausTemperature, the substituted heterocyclylpyrrolone of the general formula (XI) with O-acetyl group is formed, which by heating under acidic conditions (z. B. in a mixture
Essigsäure und Wasser) in das korrespondierende Heterocyclylpyrrolon der allgemeinen Formel (la) mit freier OH-Gruppe überführt werden kann lm nachfolgenden Schema 4 haben X, Y und Q die zuvor definierten Bedeutungen, R2 der allgemeinen Formel (1) steht beispielhaft, aber nicht einschränkend für OH, OC(0)CH3 und R3 der allgemeinen Formel (1) steht beispielhaft, aber nicht einschränkend, für Wasserstoff. Acetic acid and water) can be converted into the corresponding heterocyclylpyrrolone of the general formula (Ia) with a free OH group. In scheme 4 below, X, Y and Q have the meanings defined above, R 2 of the general formula (1) is exemplary but not restricting OH, OC (0) CH 3 and R 3 of the general formula (1) is an example, but not limiting, of hydrogen.
AC20 AcOH AC 2 0 AcOH
A Base L Pyridin L H,,O  A base L pyridine L H ,, O
N— Q A N— Q
Figure imgf000043_0002
N - QAN - Q
Figure imgf000043_0002
Br/OH ' N°H o O H Br / OH 'N ° H o OH
Q (XI)  Q (XI)
(IX) (IV) (la)  (IX) (IV) (la)
(X)  (X)
Schema 4  Scheme 4
Falls substituierte Heterocyclylpyrrolone der allgemeinen Formel (I) über eine freie Hydroxyfunktion verfügen, so kann diese mit geeigneten Reagenzien acyliert (z. B. unter Verwendung eines geeigneten Säurechlorids und mit Hilfe einer geeigneten Base wie Triethylamin in einem geeigneten polar- aprotischen Lösemittel), sulfonyliert (z. B. unter Verwendung eines geeigneten Sulfonylchlorids und mit Hilfe einer geeigneten Base wie Triethylamin in einem geeigneten polar-aprotischen Lösemittel), alkyliert (z. B. unter Verwendung eines geeigneten Alkylhalogenids und mit Hilfe einer geeigneten Base wie Kaliumcarbonat, Caesiumcarbonat oder Natriumhydrid in einem geeigneten polar-aprotischen Lösemittel) oder auch in ein Carbonat überführt werden (vgl. WO2015/018434). lm nachfolgenden Schema 5 haben X, Y und Q die zuvor definierten Bedeutungen, R2 der allgemeinen Formel (1) steht beispielhaft, aber nicht einschränkend für OH, OCH3, OSO2CH3, OC(0)CH3 und OC(0)OCH3 und R3 der allgemeinen Formel (1) steht beispielhaft, aber nicht einschränkend, für Wasserstoff. If substituted heterocyclylpyrrolones of the general formula (I) have a free hydroxy function, this can be acylated with suitable reagents (for example using a suitable acid chloride and with the aid of a suitable base such as triethylamine in a suitable polar-aprotic solvent), sulfonylated (e.g. using a suitable sulfonyl chloride and using a suitable base such as triethylamine in a suitable polar aprotic solvent), alkylated (e.g. using a suitable alkyl halide and using a suitable base such as potassium carbonate, cesium carbonate or sodium hydride in a suitable polar-aprotic solvent) or also be converted into a carbonate (cf. WO2015 / 018434). In scheme 5 below, X, Y and Q have the meanings defined above, R 2 of the general formula (1) is exemplary but not restrictive of OH, OCH3, OSO2CH3, OC (0) CH 3 and OC (0) OCH 3 and R 3 of the general formula (1) represents, by way of example, but not by way of limitation, hydrogen.
Figure imgf000044_0001
Figure imgf000044_0001
Schema 5 Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) sind im Folgenden aufgeführt. Die angegebenen Beispielnummem entsprechen den in den nachstehenden Tabellen 1.1 bis 1.122 genannten Nummerierungen. Die H-NMR-, 13C-NMR- und 19F- NMR-spektroskopischen Daten, die für die in den nachfolgenden Abschnitten beschriebenen chemischen Beispiele angegeben sind, (400 MHz bei *H-NMR und 150 MHz bei 13C-NMR und 375 MHz bei 19F-NMR, Lösungsmittel CDCL, CD3OD oder ck-DMSO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Bruker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplet, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septet, dq = Doppelquartett, dt = Doppeltriplett. Bei Diastereomerengemischen werden entweder die jeweils signifikanten Signale beider Diastereomere oder das charakteristische Signal des Hauptdiastereomers angegeben. Die verwendeten Abkürzungen für chemische Gruppen haben beispielsweise die nachfolgenden Bedeutungen: Me = CH3, Et = CH2CH3, t-Hex = C(CH3)2CH(CH3)2, t- Bu = C(CH3)3, n-Bu = unverzweigtes Butyl, n-Pr = unverzweigtes Propyl, i-Pr = verzweigtes Propyl, c- Pr = Cyclopropyl, c-Hex = Cyclohexyl. Synthesebeispiele: Scheme 5 Selected detailed synthesis examples for the compounds of the general formula (1) according to the invention are listed below. The example numbers given correspond to the numbering given in Tables 1.1 to 1.122 below. The H-NMR, 13 C-NMR and 19 F-NMR spectroscopic data given for the chemical examples described in the following sections (400 MHz for * H-NMR and 150 MHz for 13 C-NMR and 375 MHz at 19 F-NMR, solvent CDCL, CD3OD or ck-DMSO, internal standard: tetramethylsilane d = 0.00 ppm) were obtained with a device from Bruker, and the signals indicated have the meanings given below: br = broad ( it); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of a double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. In the case of mixtures of diastereomers, either the respectively significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations for chemical groups used have, for example, the following meanings: Me = CH3, Et = CH2CH3, t-Hex = C (CH3) 2CH (CH3) 2, t-Bu = C (CH3) 3, n-Bu = unbranched butyl , n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-Hex = cyclohexyl. Synthesis Examples:
5-Methyl-4H-isoxazol-3-amin
Figure imgf000045_0001
iV-Hydroxyhamstoff (6.012 g, 77.5 mmol, 1.05 equiv) wurde in Methanol (80 mL) gelöst und 5.4M NaOMe in MeOH (14.35 ml, 77.5 mmol, 1.05 equiv) zugegeben. Die Lösung wurde 15 min gerührt und eine Lösung bestehend aus 3-Crotonsäurenitril (5.00 g, 73.8 mmol, 1.00 equiv) in MeOH (20 mL) wurde zugetropft. Das Reaktionsgemisch wurde für 24 h bei Raumtemperatur gerührt, das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03-Lösung (12 g in 30 mL H2O) versetzt. Die wässrige Phase wurde fünf mal mit je 25 ml Ethylacetat extrahiert, und die vereinigten organischen Phasen wurden anschließend über Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt und das Produkt 5-Mcthyl-4//-isoxazol-3-amin (4.45 g, 57%) wurde als leicht bräunlicher Feststoff erhalten. *H-NMR (400 MHz, CDCL d, ppm) 4.99 (m, 1H), 3.99 (br. s, 2H), 3.00 (m, 1H), 2.61 (m, 1H), 1.37 (d, 3H). 5-methyl-4H-isoxazol-3-amine
Figure imgf000045_0001
IV-hydroxyurea (6,012 g, 77.5 mmol, 1.05 equiv) was dissolved in methanol (80 mL) and 5.4M NaOMe in MeOH (14.35 ml, 77.5 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-crotononitrile (5.00 g, 73.8 mmol, 1.00 equiv) in MeOH (20 mL) was added dropwise. The reaction mixture was stirred for 24 h at room temperature, the methanol was removed under reduced pressure and the residue was treated with aqueous K2C03 solution (12 g in 30 mL H2O). The aqueous phase was extracted five times with 25 ml of ethyl acetate each time, and the combined organic phases were then dried over sodium sulfate. The solvent was removed under reduced pressure and the product 5-methyl-4 // - isoxazol-3-amine (4.45 g, 57%) was obtained as a slightly brownish solid. * H-NMR (400 MHz, CDCL d, ppm) 4.99 (m, 1H), 3.99 (br. S, 2H), 3.00 (m, 1H), 2.61 (m, 1H), 1.37 (d, 3H).
5-Ethyl-5-methyl-4H-isoxazol-3-amin
Figure imgf000045_0002
5-ethyl-5-methyl-4H-isoxazol-3-amine
Figure imgf000045_0002
N-Hydroxyhamstoff (17.185 g, 221.4 mmol, 1.05 equiv) wurde in Methanol (442 mL) gelöst und festes NaOMe (11.96 g 221.4 mmol, 1.05 equiv) zugegeben. Die Lösung wurde 15 min gerührt und eine Lösung bestehend aus 3-Ethylcrotonsäurenitril (20.07 g, 210.9 mmol, 1.00 equiv) in MeOH (210 mL) wurde zugetropft. Das Reaktionsgemisch wurde insgesammt für 27 h unter Rückfluß erhitzt. Das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03 -Lösung (108 g in 270 mL H20) unter Rühren versetzt und anschließend zweimal mal mit je 500 ml Ethylacetat extrahiert, die vereinigten, organischen Phasen mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt und der erhaltene Feststoff 10 min. mit 45 ml eines Gemisches aus eiskaltem Heptan/Ethylacetat 4:1 verrührt, abgesaugt und mit 10 ml des gleichen, eiskalten Gemisches gewaschen. Das Lösungsmittel der  N-Hydroxyurea (17.185 g, 221.4 mmol, 1.05 equiv) was dissolved in methanol (442 mL) and solid NaOMe (11.96 g 221.4 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-ethylcrotonitrile (20.07 g, 210.9 mmol, 1.00 equiv) in MeOH (210 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 27 h. The methanol was removed under reduced pressure and the residue was mixed with aqueous K2C03 solution (108 g in 270 mL H20) with stirring and then extracted twice with 500 ml of ethyl acetate each time, the combined organic phases were washed with saturated NaCl solution and over Dried sodium sulfate. The solvent was removed under reduced pressure and the solid obtained for 10 min. stirred with 45 ml of a mixture of ice-cold heptane / ethyl acetate 4: 1, suction filtered and washed with 10 ml of the same, ice-cold mixture. The solvent of the
Mutterlauge wurde unter vermindertem Druck entfernt und der erhaltene Feststoff wurde ebenfalls 10 min. mit 15 ml eines Gemisches aus eiskaltem Heptan/Ethylacetat 4:1 verrührt, abgesaugt und mit 10 ml des gleichen, eiskalten Gemisches gewaschen. Dieser Vorgang wurde mehrfach wiederholt und ergab in mehreren Fraktionen das Produkt 5-Ethyl-5-Methyl-4H-isoxazol-3-amin (22.49 g, 80%) als farblosen Feststoff. 1H-NMR (400 MHz, CDCL d, ppm) 3.99 (br. s, 2H), 2.79 (m, 1H), 2.62 (m, 1H), 1.68 (m, 2H), 1.35 (s, 3H), 0.96 (dt, 3H). 5-tert-butyl-4H-isoxazol-3-amin
Figure imgf000046_0001
Mother liquor was removed under reduced pressure and the solid obtained was also 10 min. stirred with 15 ml of a mixture of ice-cold heptane / ethyl acetate 4: 1, suction filtered and washed with 10 ml of the same, ice-cold mixture. This process was repeated several times and in several fractions gave the product 5-ethyl-5-methyl-4H-isoxazol-3-amine (22.49 g, 80%) as a colorless solid. 1H-NMR (400 MHz, CDCL d, ppm) 3.99 (br. S, 2H), 2.79 (m, 1H), 2.62 (m, 1H), 1.68 (m, 2H), 1.35 (s, 3H), 0.96 (German, 3H). 5-tert-butyl-4H-isoxazol-3-amine
Figure imgf000046_0001
N-Hydroxyhamstoff (2.993 g, 38.6 mmol, 1.05 equiv) wurde in Methanol (77 mL) gelöst und festes NaOMe (2.13 g 38.6 mmol, 1.05 equiv) zugegeben. Die Lösung wurde 15 min gerührt und eine Lösung bestehend aus 3-tert.-Butylacrylnitril (4.01 g, 36.7 mmol, 1.00 equiv) in MeOH (36.7 mL) wurde zugetropft. Das Reaktionsgemisch wurde insgesammt für 22 h unter Rückfluß erhitzt. Das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03 -Lösung (18.8 g in 47 mL H20) versetzt und anschließend zweimal mal mit je 90 ml Ethylacetat extrahiert, die vereinigten, organischen Phasen mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt und der erhaltene Feststoff 10 min. mit 50 ml eines Gemisches aus eiskaltem Heptan/Ethylacetat 4:1 verrührt, abgesaugt und mit 5 ml des gleichen, eiskalten Gemisches gewaschen. Das Produkt 5-tert.-butyl-4H-isoxazol-3-amin (2.68 g, 43%) wurde als gelblichen Feststoff erhalten. 1H-NMR (400 MHz, CDCF d, ppm) 4.24 (t, 1H) 3.93 (br. s, 2H), 2.78 (d, 2H), 0.94 (s, 9H). l,8-dioxa-2-azaspiro[4.5]dec-2-en-3-amin
Figure imgf000046_0002
N-Hydroxyurea (2,993 g, 38.6 mmol, 1.05 equiv) was dissolved in methanol (77 mL) and solid NaOMe (2.13 g 38.6 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of 3-tert-butylacrylonitrile (4.01 g, 36.7 mmol, 1.00 equiv) in MeOH (36.7 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 22 h. The methanol was removed under reduced pressure and the residue was treated with aqueous K2C03 solution (18.8 g in 47 mL H20) and then extracted twice with 90 ml of ethyl acetate each time, the combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate , The solvent was removed under reduced pressure and the solid obtained for 10 min. stirred with 50 ml of a mixture of ice-cold heptane / ethyl acetate 4: 1, suction filtered and washed with 5 ml of the same, ice-cold mixture. The product 5-tert-butyl-4H-isoxazol-3-amine (2.68 g, 43%) was obtained as a yellowish solid. 1H NMR (400 MHz, CDCF d, ppm) 4.24 (t, 1H) 3.93 (br. S, 2H), 2.78 (d, 2H), 0.94 (s, 9H). l, 8-dioxa-2-azaspiro [4.5] dec-2-ene-3-amine
Figure imgf000046_0002
N-Hydroxyhamstoff (3.143 g, 40.5 mmol, 1.05 equiv) wurde in Methanol (81 mL) gelöst und festes NaOMe (2.23 g 40.5 mmol, 1.05 equiv) zugegeben. Die Lösung wurde 15 min gerührt und eine Lösung bestehend aus Tetrahydro-4H-pyran-4-yliden)acetonitril (5.00 g, 38.6 mmol, 1.00 equiv) in MeOH (38.5 mL) wurde zugetropft. Das Reaktionsgemisch wurde insgesammt für 6 h unter Rückfluß erhitzt. Das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03 -Lösung (19.7 g in 49 mL H20) versetzt und anschließend zweimal mal mit je 94 ml Ethylacetat extrahiert, die vereinigten, organischen Phasen mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt und der erhaltene Feststoff zweimal je 5 min. mit 22 ml eines Gemisches aus Heptan/Ethylacetat 4:1 bei 45 C verrührt und abdekantiert. Der Kolbenrückstand ergab das Produkt l,8-dioxa-2-azaspiro[4.5]dec-2-en-3-amin (4.22 g, 70%) als farblosen Feststoff. 1H-NMR (400 MHz, CDCL d, ppm) 3.91 (br. s, 2H), 3.86 (m, 2H), 3.68 (m, 2H), 2.75 (s, 2H), 1.90 (m, 2H), 1.76 (m, 2H). 5,5- Di mcthy 1-4/7- isoxazo 1-3 -amin
Figure imgf000047_0001
N-Hydroxyurea (3,143 g, 40.5 mmol, 1.05 equiv) was dissolved in methanol (81 mL) and solid NaOMe (2.23 g 40.5 mmol, 1.05 equiv) was added. The solution was stirred for 15 min and a solution consisting of tetrahydro-4H-pyran-4-ylidene) acetonitrile (5.00 g, 38.6 mmol, 1.00 equiv) in MeOH (38.5 mL) was added dropwise. The reaction mixture was heated under reflux for a total of 6 h. The methanol was removed under reduced pressure and the residue was mixed with aqueous K2C03 solution (19.7 g in 49 mL H20) and then extracted twice with 94 ml of ethyl acetate each time, the combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate , The solvent was removed under reduced pressure and the solid obtained twice twice for 5 min. stirred with 22 ml of a mixture of heptane / ethyl acetate 4: 1 at 45 C and decanted. The flask residue gave the product 1,8-dioxa-2-azaspiro [4.5] dec-2-en-3-amine (4.22 g, 70%) as a colorless solid. 1H-NMR (400 MHz, CDCL d, ppm) 3.91 (br. S, 2H), 3.86 (m, 2H), 3.68 (m, 2H), 2.75 (s, 2H), 1.90 (m, 2H), 1.76 (m, 2H). 5,5- Di mcthy 1-4 / 7- isoxazo 1-3 -amin
Figure imgf000047_0001
iV-Hydroxyhamstoff (1.91 g, 24.5 mmol, 1.05 equiv) wurde in Methanol (40 mL) gelöst und IV-hydroxyurea (1.91 g, 24.5 mmol, 1.05 equiv) was dissolved in methanol (40 mL) and
5.4M NaOMe in MeOH (4.57 mL, 24.5 mmol, 1.05 equiv) zugegeben. Die Lösung wurde 15 min gerührt und eine Lösung bestehend aus 3-Methylcrotonsäurenitril (1.90 g, 23.4 mmol, 1.00 equiv) in MeOH (20 mL) wurde zugetropft. Das Reaktionsgemisch wurde für 24 h unter Rückfluß erhitzt. Das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03-Lösung (12 g in 30 mL H2O) versetzt. Die wässrige Phase wurde mehrfach mit Ethylacetat extrahiert, und die vereinigten organischen Phasen wurden danach über Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt und das Produkt 5,5-Dimethyl-477-isoxazol-3-amin (2.12 g, 71%) wurde als farbloser Feststoff erhalten. 'H-NMR (400 MHz, CDCI3 d, ppm) 3.82 (br. s, 2H), 2.73 (s, 2H), 1.41 (s, 6H). 5.4M NaOMe in MeOH (4.57 mL, 24.5 mmol, 1.05 equiv) added. The solution was stirred for 15 min and a solution consisting of 3-methylcrotonitrile (1.90 g, 23.4 mmol, 1.00 equiv) in MeOH (20 mL) was added dropwise. The reaction mixture was heated under reflux for 24 h. The methanol was removed under reduced pressure and the residue was treated with aqueous K2C03 solution (12 g in 30 mL H2O). The aqueous phase was extracted several times with ethyl acetate and the combined organic phases were then dried over sodium sulfate. The solvent was removed under reduced pressure and the product 5,5-dimethyl-477-isoxazol-3-amine (2.12 g, 71%) was obtained as a colorless solid. 'H NMR (400 MHz, CDCI3 d, ppm) 3.82 (br. S, 2H), 2.73 (s, 2H), 1.41 (s, 6H).
3a,4,5,6,7,7a-Hexahydro-l,2-benzoxazol-3-amin
Figure imgf000047_0002
3a, 4,5,6,7,7a-hexahydro-l, 2-benzoxazol-3-amine
Figure imgf000047_0002
iV-Hydroxyhamstoff (0.398 g, 5.13 mmol, 1.10 equiv) wurde in Methanol (10-2 mL) gelöst und festes NaOMe (0.277 g, 5.13 mmol, 1.10 equiv) zugegeben. Die Lösung wurde 15 min gerührt und anschließend mit einer Lösung bestehend aus Cyclohexene-1 -carbonitrile (0.5 g, 4.67 mmol, 1.00 equiv) in MeOH (4.6 mL) versetzt. Das Reaktionsgemisch wurde in ein Mikrowellengefäß überführt und 6.5 Stunden bei 120 - 140 °C in der Mikrowelle bestrahlt. Nach Zugabe von weiterem IV-hydroxyurea (0.398 g, 5.13 mmol, 1.10 equiv) was dissolved in methanol (10-2 mL) and solid NaOMe (0.277 g, 5.13 mmol, 1.10 equiv) was added. The solution was stirred for 15 min and then a solution consisting of cyclohexene-1-carbonitrile (0.5 g, 4.67 mmol, 1.00 equiv) in MeOH (4.6 mL) was added. The reaction mixture was transferred to a microwave vessel and irradiated in the microwave at 120-140 ° C. for 6.5 hours. After adding more
/V-Hydroxyharnstoff (0.181 g, 2.33 mmol, 0.5 equiv) und NaOMe (0.126 g, 2.33 mmol, 0.5 equiv) erfolgte eine weitere Bestrahlung in der Mikrowelle für 2.5 Stunden bei 130 °C. Das Methanol wurde unter vermindertem Druck entfernt und der Rückstand mit wässriger K2C03-Lösung (4.0 g in 10 mL H2O) versetzt. Die wässrige Phase wurde mehrfach mit Ethylacetat extrahiert, die vereinigten organischen Phasen einmal mit 10 mL gesät. NaCl-Lösung gewaschen und anschließend über / V-hydroxyurea (0.181 g, 2.33 mmol, 0.5 equiv) and NaOMe (0.126 g, 2.33 mmol, 0.5 equiv), further irradiation was carried out in the microwave for 2.5 hours at 130 ° C. The methanol was removed under reduced pressure and aqueous K2C03 solution (4.0 g in 10 mL H2O) was added to the residue. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were sown once with 10 ml. Washed NaCl solution and then over
Natriumsulfat getrocknet. Das Lösungsmittel wurde unter vermindertem Druck entfernt. Der Rückstand wurde in einer Mischnung aus Heptan/Ethylacetat (4:1, 10 mL) suspendiert, ab filtriert und mit einer Mischung aus Heptan/Ethylacetat (4: 1, 5 ml) gewaschen. Das Produkt 3a,4,5,6,7,7a-Hexahydro-l,2- benzoxazo 1-3 -amin (0.292 g, 41%) wurde als farbloser Feststoff erhalten. *H-NMR (600 MHz,Dried sodium sulfate. The solvent was removed under reduced pressure. The residue was suspended in a mixture of heptane / ethyl acetate (4: 1, 10 ml), filtered off and washed with a mixture of heptane / ethyl acetate (4: 1, 5 ml). The product 3a, 4,5,6,7,7a-hexahydro-1,2-benzoxazo 1-3-amine (0.292 g, 41%) was obtained as a colorless solid. * H-NMR (600 MHz,
DMSO-DÖ d ppm) 9.38 (s, 1H), 6.15 (m, 1H), 5.23 (s, 2H), 2.14 (m, 2H), 2.08 (m, 2H), 1.55 (m, 4H). 1 -(5,5-Dimcthyl-4//-isoxazol-3-yl)-3-mcthyl-pynOlc-2,5-dion DMSO-D Ö d ppm) 9.38 (s, 1H), 6.15 (m, 1H), 5.23 (s, 2H), 2.14 (m, 2H), 2.08 (m, 2H), 1.55 (m, 4H). 1 - (5,5-Dimcthyl-4 // - isoxazol-3-yl) -3-methyl-pynOlc-2,5-dione
Figure imgf000048_0001
Figure imgf000048_0001
Citraconsäureanhydrid (308 mg, 2.69 mmol, 1.05 equiv), und 5,5-Dimcthyl-4/7-isoxazol-3-amin (380 mg, 2.56 mmol, 1.00 equiv) wurden in Essigsäure (10 ml) gelöst und 10 h lang unter Rückfluß erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit Wasser versetzt und die wässrige Phase wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt l-(5,5-Dimethyl-4T/-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion (320 mg, 57%) als farbloser Feststoff erhalten.‘H-NMR (400 MHz, CDC13 d, ppm) 6.48 (s, 1H), 3.15 (s, 2H), 2.14 (s, 3H), 1.48 (s, 6H). l-(4H-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion Citraconic anhydride (308 mg, 2.69 mmol, 1.05 equiv), and 5,5-dimcthyl-4/7-isoxazol-3-amine (380 mg, 2.56 mmol, 1.00 equiv) were dissolved in acetic acid (10 ml) and for 10 h heated under reflux. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and the solvent removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave the product 1- (5,5-dimethyl-4T / -isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (320 mg, 57%) as Colorless solid obtained.'H-NMR (400 MHz, CDC1 3 d, ppm) 6.48 (s, 1H), 3.15 (s, 2H), 2.14 (s, 3H), 1.48 (s, 6H). l- (4H-isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione
Figure imgf000048_0002
Figure imgf000048_0002
Citraconsäureanhydrid (1.074 g, 9.4 mmol, 1.05 equiv), und 4/7-isoxazol-3-amin (1.000 g, 8.9 mmol, 1.00 equiv) wurden in Essigsäure (6.6 ml) gelöst und 3 h lang unter Rückfluß erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit Wasser versetzt und die wässrige Phase wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Citraconic anhydride (1,074 g, 9.4 mmol, 1.05 equiv), and 4/7-isoxazol-3-amine (1,000 g, 8.9 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and heated under reflux for 3 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. By column chromatography purification (gradient
Ethylacetat/Heptan) wurde das Produkt l-(4T/-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion (965 mg, 51%) als farbloser Feststoff erhalten. 'H-NMR (400 MHz, CDCI3 d, ppm) 6.51 (m, 1H), 4.50 (t, 2H), 3.42 (t, 2H), 2.16 (d, 3H). l-(5-Ethyl-5-Methyl-4T/-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion  Ethyl acetate / heptane) gave the product 1- (4T / -isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (965 mg, 51%) as a colorless solid. 'H NMR (400 MHz, CDCI3 d, ppm) 6.51 (m, 1H), 4.50 (t, 2H), 3.42 (t, 2H), 2.16 (d, 3H). l- (5-ethyl-5-methyl-4T / -isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione
Figure imgf000048_0003
Figure imgf000048_0003
Citraconsäureanhydrid (1.000 g, 9.4 mmol, 1.0 equiv), und 5-Ethyl-5-Mcthyl-4//-isoxazol-3-amin (1.177 g, 9.2 mmol, 1.05 equiv) wurden in Essigsäure (40 ml) gelöst und 1.5 h lang unter Rückfluß erhitzt. Nach ca. 5 min. verfärbt sich die Lösung orange und anschließend bräunlich. Nach dem Citraconic anhydride (1,000 g, 9.4 mmol, 1.0 equiv), and 5-ethyl-5-methyl-4 // - isoxazol-3-amine (1,177 g, 9.2 mmol, 1.05 equiv) were dissolved in acetic acid (40 ml) and 1.5 for hours at reflux heated. After about 5 minutes. the solution turns orange and then turns brownish. After this
Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit Wasser versetzt und die wässrige Phase wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. By column chromatography purification (gradient
Ethylacetat/Heptan) wurde das Produkt l-(5-Ethyl-5-Methyl-4T/-isoxazol-3-yl)-3-methyl-pyrrole-2,5- dion (728 mg, 37%) als farbloser Feststoff erhalten. 'H-NMR (400 MHz, CDCF d, ppm) 6.48 (m, 1H), 3.19 (dd, 1H), 3.05 (dd, 1H), 2.15 (d, 3H), 1.75 (q, 2H), 1.43 (s, 3H), 0.98 (t, 3H). 3a,4,5,6,7,7a-Hexahydro-l,2-benzoxazol-3-yl)-3-methyl-pyrrole-2,5-dion  Ethyl acetate / heptane) gave the product 1- (5-ethyl-5-methyl-4T / -isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (728 mg, 37%) as a colorless solid , 'H NMR (400 MHz, CDCF d, ppm) 6.48 (m, 1H), 3.19 (dd, 1H), 3.05 (dd, 1H), 2.15 (d, 3H), 1.75 (q, 2H), 1.43 ( s, 3H), 0.98 (t, 3H). 3a, 4,5,6,7,7a-hexahydro-l, 2-benzoxazol-3-yl) -3-methyl-pyrrole-2,5-dione
Figure imgf000049_0001
Figure imgf000049_0001
Citraconsäureanhydrid (167 mg, 1.46 mmol, 1.05 equiv), und 3a,4,5,6,7,7a-Hexahydro-l,2-benzoxazol- 3-amin (212 mg, 1.39 mmol, 1.00 equiv) wurden in Essigsäure (10 ml) gelöst und insgesammt 17.5 h lang unter Rückfluß erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit Wasser versetzt und die wässrige Phase wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt 3a,4,5,6,7,7a-Hexahydro-l,2-benzoxazol- 3-yl)-3-methyl-pyrrole-2,5-dion (31.8 mg, 9 %) als farbloser Feststoff erhalten. H-NMR (400 MHz, CDCL d, ppm) 6.92 (br, 2H), 6.49 (m, 1H), 2.48 (m, 2H), 2.39 (d, 3H), 2.29 (m, 2H), 2.04 (m, 1H), 1.75 (m, 2H), 1.28 (m, 1H). l-(5-(4-Chlorpheny)-4H-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion  Citraconic anhydride (167 mg, 1.46 mmol, 1.05 equiv), and 3a, 4,5,6,7,7a-hexahydro-1,2-benzoxazol-3-amine (212 mg, 1.39 mmol, 1.00 equiv) were dissolved in acetic acid ( 10 ml) dissolved and heated under reflux for a total of 17.5 h. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave the product 3a, 4,5,6,7,7a-hexahydro-1,2-benzoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (31.8 mg, 9%) as a colorless solid. H-NMR (400 MHz, CDCL d, ppm) 6.92 (br, 2H), 6.49 (m, 1H), 2.48 (m, 2H), 2.39 (d, 3H), 2.29 (m, 2H), 2.04 (m , 1H), 1.75 (m, 2H), 1.28 (m, 1H). l- (5- (4-Chlorpheny) -4H-isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione
Figure imgf000049_0002
Figure imgf000049_0002
Citraconsäureanhydrid (235 mg, 2.06 mmol, 1.05 equiv), und 5-(4-Chlorphenyl)-4H-isoxazol-3-amin (500 mg, 1.96 mmol, 1.00 equiv) wurden in Essigsäure (6.6 ml) gelöst und insgesammt 3.5 h lang unter Rückfluß erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Reaktionsgemisch mit Wasser versetzt und die wässrige Phase wurde mehrmals mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden mit gesättigter NaCl-Lösung gewaschen und über Natriumsulfat getrocknet, filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt l-(5-(4-Chlorpheny)-4H-isoxazol-3-yl)-3-methyl- pyrrole-2,5-dion (290.7 mg, 51 %) als farbloser Feststoff erhalten. 1H-NMR (400 MHz, CDC13 d, ppm) 7.35 (m, 4H), 6.51 (m, 1H), 5.70 (dq, 1H), 3.87 (dd, 1H), 3.36 (dd, 1H), 2.15 (d, 3H). l-(5-Ethyl-5-Methyl-4H-isoxazol-3-yl)-3-brom-pyrrole-2,5-dion Citraconic anhydride (235 mg, 2.06 mmol, 1.05 equiv), and 5- (4-chlorophenyl) -4H-isoxazol-3-amine (500 mg, 1.96 mmol, 1.00 equiv) were dissolved in acetic acid (6.6 ml) and combined for 3.5 h heated under reflux for a long time. After cooling to room temperature, water was added to the reaction mixture and the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were washed with saturated NaCl solution and dried over sodium sulfate, filtered and the solvent removed under reduced pressure. The product l- (5- (4-chloropheny) -4H-isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (290.7 mg, 51%) was purified by column chromatography (ethyl acetate / heptane gradient). obtained as a colorless solid. 1H-NMR (400 MHz, CDC13 d, ppm) 7.35 (m, 4H), 6.51 (m, 1H), 5.70 (dq, 1H), 3.87 (dd, 1H), 3.36 (dd, 1H), 2.15 (d , 3H). l- (5-ethyl-5-methyl-4H-isoxazol-3-yl) -3-bromo-pyrrole-2,5-dione
Figure imgf000050_0001
Figure imgf000050_0001
Brommaleinsäureanhydrid (854 mg, 4.7 mmol, 1.2 equiv), und 5-Ethyl-5-Mcthyl-4//-isoxazol-3-amin (500 mg, 3.9 mmol, 1.0 equiv) wurden in trockenem Toluol unter Schutzgas (10 ml) vermischt und 10.5 h lang bei Raumtemperatur unter Zusatz von Amberlyst 15 (50 mg) gerührt. Das Reaktionsgemisch wurde filtriert und das Lösungsmittel unter vermindertem Druck entfernt. Durch  Bromomaleic anhydride (854 mg, 4.7 mmol, 1.2 equiv), and 5-ethyl-5-methyl-4 // - isoxazol-3-amine (500 mg, 3.9 mmol, 1.0 equiv) were in dry toluene under protective gas (10 ml) mixed and stirred for 10.5 h at room temperature with the addition of Amberlyst 15 (50 mg). The reaction mixture was filtered and the solvent removed under reduced pressure. By
säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt l-(5-Ethyl-5- M cthy 1-4/7- isoxazo 1-3 -yl)-3-brom-pynOlc-2,5-dion (9.5 mg, 1 %) als gelblicher Feststoff erhalten. H- NMR (400 MHz, CDCL d, ppm) 7.02 (s, 1H), 3.18 (d, 1H), 3.03 (dd, 1H), 1.76 (dq, 2H), 1.45 (s, 3H), 1.27 (dt, 3H). purification by column chromatography (gradient ethyl acetate / heptane), the product 1- (5-ethyl-5- M cthy 1-4 / 7-isoxazo 1-3 -yl) -3-bromo-pynOlc-2,5-dione (9.5 mg , 1%) as a yellowish solid. H-NMR (400 MHz, CDCL d, ppm) 7.02 (s, 1H), 3.18 (d, 1H), 3.03 (dd, 1H), 1.76 (dq, 2H), 1.45 (s, 3H), 1.27 (German , 3H).
No. 1.1-15: l-(5,5-Dimethyl-477-isoxazol-3-yl)-2-hydroxy-3-methyl-277-pyrrol-5-on No. 1.1-15: 1- (5,5-Dimethyl-477-isoxazol-3-yl) -2-hydroxy-3-methyl-277-pyrrol-5-one
Figure imgf000050_0002
Figure imgf000050_0002
l-(5,5-Dimethyl-477-isoxazol-3-yl)-3-methyl-pyrrole-2,5-dion (320 mg, 1.46 mmol, 1.00 equiv) wurde in MethanoPTHF (1 : 1, 10 ml) gelöst und auf eine Temperatur von -15 °C gekühlt. Natriumborhydrid (110 mg, 2.92 mmol, 2.00 equiv) wurde portionsweise zugegeben und das Reaktionsgemisch anschließend 2 h bei -15 °C gerührt. Die Lösung wurde auf Raumtemperatur erwärmt, mit wässriger NH4C1-Lösung versetzt und die wässrige Phase wurde mit Ethylacetat extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und das Lösunsgmittel wurde unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (250x50 mm, VDSpher Opti Aqua, 1 Omih, 2l0nm, isokratische Elution: 4% MeCN, 95.95% H2O, 0.05% 1- (5,5-Dimethyl-477-isoxazol-3-yl) -3-methyl-pyrrole-2,5-dione (320 mg, 1.46 mmol, 1.00 equiv) was dissolved in methanoPTHF (1: 1, 10 ml) dissolved and cooled to a temperature of -15 ° C. Sodium borohydride (110 mg, 2.92 mmol, 2.00 equiv) was added in portions and the reaction mixture was then stirred at -15 ° C. for 2 h. The solution was warmed to room temperature, aqueous NH 4 C1 solution was added and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure. By column chromatographic purification (250x50 mm, VDSpher Opti Aqua, 1 Omih, 2l0nm, isocratic elution: 4% MeCN, 95.95% H2O, 0.05%
Trifluoressigsäure TFA. Die Trennung läuft bei einem Fluss von 90ml/ min.) wurde das Produkt 1 -(5,5- Dimethyl-477-isoxazol-3-yl)-2-hydroxy-3-methyl-277-pyrrol-5-on (170 mg, 54%) als farbloser Feststoff erhalten.‘H-NMR (400 MHz, CDCL d, ppm) 5.87 (s, 1H), 5.78 (s, 1H), 4.39 (br. s, 1H), 3.36 (s, 2H), 2.13 (s, 3H), 1.44 (s, 6H). No. 1.1-16: l-(5-Ethyl-5-methyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on Trifluoroacetic acid TFA. The separation runs at a flow of 90 ml / min.) The product 1 - (5,5-dimethyl-477-isoxazol-3-yl) -2-hydroxy-3-methyl-277-pyrrol-5-one (170 mg, 54%) was obtained as a colorless solid.'H-NMR (400 MHz, CDCL d, ppm) 5.87 (s, 1H), 5.78 (s, 1H), 4.39 (br. s, 1H), 3.36 (s, 2H), 2.13 (s, 3H), 1.44 (s, 6H). No. 1.1-16: 1- (5-Ethyl-5-methyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one
Figure imgf000051_0001
Figure imgf000051_0001
1 -(5-Ethyl-5-mcthyl-4/7-isoxazol-3-yl)-3-mcthyl-pynOlc-2,5-dion (223 mg, 1.00 mmol, 1.00 equiv) wurde in Methanol/THF (1 :1, 10 ml) gelöst und auf eine Temperatur von -30 °C gekühlt.  1 - (5-Ethyl-5-methyl-4/7-isoxazol-3-yl) -3-methyl-pynOlc-2,5-dione (223 mg, 1.00 mmol, 1.00 equiv) was dissolved in methanol / THF (1 : 1, 10 ml) dissolved and cooled to a temperature of -30 ° C.
Natriumborhydrid (76 mg, 2.00 mmol, 2.00 equiv) wurde portionsweise zugegeben und das Sodium borohydride (76 mg, 2.00 mmol, 2.00 equiv) was added in portions and the
Reaktionsgemisch anschließend 2 h bei -30 °C gerührt. Die Lösung wurde auf Raumtemperatur erwärmt, auf Wasser gegeben und die organischen Lösunsgmittel weitestgehend unter vermindertem Druck entfernt. Der Rückstand wurde dreimal mit je 20 ml Dichlormethan verrührt, die vereinten organischen Phasen über einen Phasenseperator getrocknet und das Lösunsgmittel anschließend unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient The reaction mixture was then stirred at -30 ° C. for 2 h. The solution was warmed to room temperature, added to water and the organic solvents largely removed under reduced pressure. The residue was stirred three times with 20 ml of dichloromethane each time, the combined organic phases were dried over a phase separator and the solvent was then removed under reduced pressure. By column chromatography purification (gradient
Ethylacetat/Heptan) wurde das Produkt l-(5-Ethyl-5-methyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H- pyrrol-5-on (190 mg, 78%) als farbloser Feststoff erhalten. H-NMR (400 MHz, CDCF d, ppm) 5.82 (m, 1H), 5.54 (br, OH), 3.39 (m, 1H), 3.30 (m, 1H), 2.13 (d, 3H), 1.71 (m, 2H), 1.37 (s, 3H), 0.97 (m, 3H). Ethyl acetate / heptane) the product was 1- (5-ethyl-5-methyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (190 mg, 78%) colorless solid obtained. H-NMR (400 MHz, CDCF d, ppm) 5.82 (m, 1H), 5.54 (br, OH), 3.39 (m, 1H), 3.30 (m, 1H), 2.13 (d, 3H), 1.71 (m , 2H), 1.37 (s, 3H), 0.97 (m, 3H).
No. 1.11-15: [l-(5,5-Dimethyl-477-isoxazol-3-yl)-3-methyl-5-oxo-277-pyrrol-2-yl]-ethylcarbonat No. 1.11-15: [1- (5,5-Dimethyl-477-isoxazol-3-yl) -3-methyl-5-oxo-277-pyrrol-2-yl] ethyl carbonate
Figure imgf000051_0002
Figure imgf000051_0002
Natriumhydrid (16 mg, 0.40 mmol, 1.10 equiv) wurde in THF (7.5 mL) vorgelegt und eine Lösung aus l-(5,5-Dimethyl-477-isoxazol-3-yl)-2-hydroxy-3-methyl-277-pyrrol-5-on (85 mg, 0.36 mmol, 1.00 equiv) in THF (3 mL) zugegeben. Das Reaktionsgemisch wurde 16 h bei Raumtemperatur gerührt, auf Eiswasser gegeben und die wässrige Phase anschließend mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und das Lösunsgmittel wurde unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient  Sodium hydride (16 mg, 0.40 mmol, 1.10 equiv) was placed in THF (7.5 mL) and a solution of l- (5,5-dimethyl-477-isoxazol-3-yl) -2-hydroxy-3-methyl-277 -pyrrol-5-one (85 mg, 0.36 mmol, 1.00 equiv) in THF (3 mL) added. The reaction mixture was stirred for 16 h at room temperature, poured onto ice water and the aqueous phase was then extracted with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and the solvent was removed under reduced pressure. By column chromatography purification (gradient
Ethylacetat/Heptan) wurde das Produkt [1 -(5,5- Di mcthy 1-4/7- isoxazo 1-3 -yl)-3-mct hyl-5-oxo-2/7-py rrol- 2-yl]-ethylcarbonat (19.5 mg, 18%) als farbloser Feststoff erhalten. H-NMR (400 MHz, CDCI3 d, ppm) 6.83 (s, 1H), 5.93 (s, 1H), 4.26-4.33 (m, 2H), 3.39 (d, 1H), 3.27 (d, 1H), 2.09 (s, 3H), 1.43 (s, 3H), 1.40 (s, 3H), 1.35 (t, 3H). No. 1.5-15: [ 1 -(5,5- Di mcthyl-4//-isoxazo 1-3 -yl)-3-mcthy l-5-oxo-2//-pyrml-2-yl] -propionat Ethyl acetate / heptane) the product was [1- (5,5-dimethyl 1-4 / 7-isoxazo 1-3 -yl) -3-methoxy-5-oxo-2/7-pyrol-2-yl ] -ethyl carbonate (19.5 mg, 18%) obtained as a colorless solid. H-NMR (400 MHz, CDCI 3 d, ppm) 6.83 (s, 1H), 5.93 (s, 1H), 4.26-4.33 (m, 2H), 3.39 (d, 1H), 3.27 (d, 1H), 2.09 (s, 3H), 1.43 (s, 3H), 1.40 (s, 3H), 1.35 (t, 3H). No. 1.5-15: [1 - (5,5-dimethyl-4 // - isoxazo 1-3 -yl) -3-methyl-5-oxo-2 // - pyrml-2-yl] propionate
Figure imgf000052_0001
Figure imgf000052_0001
1 -(5,5-Dimcthyl-4//-isoxazol-3-yl)-2-hydmxy-3-mcthyl-2//-pynOl-5-on (130 mg, 0.61 mmol,  1 - (5,5-Dimcthyl-4 // - isoxazol-3-yl) -2-hydmxy-3-methyl-2 // - pynOl-5-one (130 mg, 0.61 mmol,
1.00 equiv) wurde in THF (5 mL) gelöst und Natriumhydrid (27 mg, 0.68 mmol, 1.10 equiv) zugegeben.1.00 equiv) was dissolved in THF (5 mL) and sodium hydride (27 mg, 0.68 mmol, 1.10 equiv) was added.
Das Reaktionsgemisch wurde 20 min bei Raumtemperatur gerührt und Propionsäurechlorid (0.06 mL, 0.68 mmol, 1.10 equiv) zugetropft. Die Reaktionslösung wurde 20 h bei Raumtemperatur gerührt, mit einer Pufferlösung (Natriumacetat/Essigsäure, 1 mL, pH = 4.65) versetzt und das Lösunsgmittel wurde unter vermindertem Druck entfernt. Der Rückstand wurde mit Wasser (5 mL) und Dichlormethan (50 mL) versetzt und die Phasen wurden anschließend getrennt. Die organische Phase wurde überThe reaction mixture was stirred for 20 min at room temperature and propionic acid chloride (0.06 mL, 0.68 mmol, 1.10 equiv) was added dropwise. The reaction solution was stirred at room temperature for 20 h, a buffer solution (sodium acetate / acetic acid, 1 mL, pH = 4.65) was added and the solvent was removed under reduced pressure. Water (5 mL) and dichloromethane (50 mL) were added to the residue and the phases were then separated. The organic phase was over
Magnesiumsulfat getrocknet, filtriert und das Lösunsgmittel wurde unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt [1 -(5,5- Dimethyl-4T/-isoxazol-3-yl)-3-methyl-5-oxo-2T/-pyrrol-2-yl]-propionat (60 mg, 36%) als farbloser Feststoff erhalten.‘H-NMR (400 MHz, CDC13 d, ppm) 7.01 (s, 1H), 5.92 (s, 1H), 3.39 (d, 1H), 3.27 (d, 1H), 2.36-2.50 (m, 2H), 2.03 (s, 3H), 1.42 (s, 3H), 1.40 (s, 3H), 1.17 (t, 3H). Magnesium sulfate dried, filtered and the solvent was removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave the product [1 - (5,5-dimethyl-4T / -isoxazol-3-yl) -3-methyl-5-oxo-2T / -pyrrol-2-yl] - Propionate (60 mg, 36%) obtained as a colorless solid .'H-NMR (400 MHz, CDC1 3 d, ppm) 7.01 (s, 1H), 5.92 (s, 1H), 3.39 (d, 1H), 3.27 ( d, 1H), 2.36-2.50 (m, 2H), 2.03 (s, 3H), 1.42 (s, 3H), 1.40 (s, 3H), 1.17 (t, 3H).
No. 1.9-15: [l-(5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-methylcarbonat No. 1.9-15: [1- (5,5-Dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] methyl carbonate
Figure imgf000052_0002
Figure imgf000052_0002
l-(5,5-Dimethyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on (109 mg, 0.5 mmol, 1.00 equiv), Chlorameisensäure-methylester (52 mg, 0.55 mmol, 1.10 eqiv) und Triethylamin (60 mg, 0.6 mmol, 1.20 equiv) wurden bei Raumtemperatur in trockenem Dichlormethan (40 ml) vermischt und 5 h bei Raumtemperatur gerührt, auf gesättigte Natruim-Hydrogencarbonat-Lösung gegeben, über einen Phasenseperator getrocknet und das organsiceh Lösunsgmittel anschließend unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das Produkt [l-(5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-methylcarbonat (56 mg, 38%) als farbloser Feststoff erhalten. 'H-NMR (400 MHz, CDCI3 d, ppm) 6.84 (s, 1H), 5.93 (s, 1H), 3.86 (s, 3H), 3.39 (d, 1H), 3.27 (d, 1H), 2.08 (s, 3H), 1.44 (s, 3H), 1.40 (s, 3H). No. 1.135-15: [l-(5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-isobutylcarbonat 1- (5,5-Dimethyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (109 mg, 0.5 mmol, 1.00 equiv), methyl chloroformate (52 mg , 0.55 mmol, 1.10 eqiv) and triethylamine (60 mg, 0.6 mmol, 1.20 equiv) were mixed at room temperature in dry dichloromethane (40 ml) and stirred for 5 h at room temperature, poured into saturated sodium hydrogen carbonate solution and dried over a phase separator and the organic solvent is then removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave the product [1- (5,5-dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] methyl carbonate ( 56 mg, 38%) obtained as a colorless solid. 'H NMR (400 MHz, CDCI3 d, ppm) 6.84 (s, 1H), 5.93 (s, 1H), 3.86 (s, 3H), 3.39 (d, 1H), 3.27 (d, 1H), 2.08 ( s, 3H), 1.44 (s, 3H), 1.40 (s, 3H). No. 1.135-15: [1- (5,5-Dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] isobutyl carbonate
Figure imgf000053_0001
Figure imgf000053_0001
l-(5,5-Dimethyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on (109 mg, 0.5 mmol, 1.00 equiv), Chlorameisensäure-isobutylester (75 mg, 0.55 mmol, 1.10 eqiv) und Triethylamin (60 mg, 0.6 mmol, 1.20 equiv) wurden bei Raumtemperatur in trockenem Dichlormethan (40 ml) vermischt und 8 h bei Raumtemperatur gerührt. Hierbei wurden mehrfach jeweils 0.5 equiv Chlorameisen-isobutylester und Triethylamin nachdosiert. Anschließend wurde auf gesättigte Natruim-Hydrogencarbonat-Lösung gegeben, über einen Phasenseperator getrocknet und das organische Lösunsgmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde das [l-(5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-isobutylcarbonat (136 mg, 75%) als farbloser Feststoff erhalten. 'H-NMR (400 MHz, CDCh d, ppm) 6.84 (s, 1H), 5.92 (s, 1H), 4.05 (m, 2H), 3.39 (d, 1H), 3.26 (d, 1H), 2.09 (s, 3H), 2.02 (m, 1H), 1.44 (s, 3H), 1.40 (s, 3H), 0.96 (d; 6H). No. 1.137-15: [l-(5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-isobutyrat 1- (5,5-Dimethyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (109 mg, 0.5 mmol, 1.00 equiv), isobutyl chloroformate (75 mg , 0.55 mmol, 1.10 eqiv) and triethylamine (60 mg, 0.6 mmol, 1.20 equiv) were mixed at room temperature in dry dichloromethane (40 ml) and stirred at room temperature for 8 h. Here, 0.5 equiv of isobutyl chloroform and triethylamine were replenished several times. It was then added to saturated sodium bicarbonate solution, dried over a phase separator and the organic solvent was removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave the [1- (5,5-dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] isobutyl carbonate (136 mg, 75%) obtained as a colorless solid. 'H NMR (400 MHz, CDCh d, ppm) 6.84 (s, 1H), 5.92 (s, 1H), 4.05 (m, 2H), 3.39 (d, 1H), 3.26 (d, 1H), 2.09 ( s, 3H), 2.02 (m, 1H), 1.44 (s, 3H), 1.40 (s, 3H), 0.96 (d; 6H). No. 1,137-15: [1- (5,5-Dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] isobutyrate
Figure imgf000053_0002
Figure imgf000053_0002
l-(5,5-Dimethyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on (39 mg, 0.18 mmol, 1.00 equiv), Isovaleriansäure-chlorid (25 mg, 0.20 mmol, 1.10 eqiv) und Triethylamin (22 mg, 0.22 mmol,1- (5,5-Dimethyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (39 mg, 0.18 mmol, 1.00 equiv), isovaleric acid chloride (25 mg , 0.20 mmol, 1.10 eqiv) and triethylamine (22 mg, 0.22 mmol,
1.20 equiv) wurden bei Raumtemperatur in trockenem Dichlormethan (5 ml) vermischt und 6 h bei Raumtemperatur gerührt. Hierbei wurden mehrfach jeweils 0.5 equiv Isovaleriansäure-chlorid und Triethylamin nachdosiert. Anschließend wurde auf gesättigte Natruim-Hydrogencarbonat-Lösung gegeben, über einen Phasenseperator getrocknet und das organische Lösunsgmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde [1- (5,5-Dimethyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-isobutyrat (35 mg, 58%) als farbloser Feststoff erhalten.‘H-NMR (400 MHz, CDCI3 d, ppm) 7.02 (s, 1H), 5.92 (s, 1H), 3.40 (d, 1H), 3.25 (d, 1H), 2.22 (m, 2H), 2.03 (s, 3H), 1.42 (s, 3H), 1.40 (s, 3H), 0.98 (d; 6H). No. 1.3-15: [1 -(5,5-Dimcthyl-4//-isoxazol-3-yl)-3-mcthyl-5-oxo-2//-pyriOl-2-yl]-acctat 1.20 equiv) were mixed at room temperature in dry dichloromethane (5 ml) and stirred for 6 h at room temperature. Here, 0.5 equiv of isovaleric acid chloride and triethylamine were replenished several times. It was then added to saturated sodium bicarbonate solution, dried over a phase separator and the organic solvent was removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave [1- (5,5-dimethyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] isobutyrate (35 mg , 58%) as a colorless solid.'H-NMR (400 MHz, CDCI 3 d, ppm) 7.02 (s, 1H), 5.92 (s, 1H), 3.40 (d, 1H), 3.25 (d, 1H) , 2.22 (m, 2H), 2.03 (s, 3H), 1.42 (s, 3H), 1.40 (s, 3H), 0.98 (d; 6H). No. 1.3-15: [1 - (5,5-Dimcthyl-4 // - isoxazol-3-yl) -3-methyl-5-oxo-2 // - pyriOl-2-yl] acctate
Figure imgf000054_0001
Figure imgf000054_0001
l-(5,5-Dimethyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on (109 mg, 0.50 mmol, 1.00 equiv), Acetlychlorid (43 mg, 0.55 mmol, 1.10 eqiv) und Triethylamin (60 mg, 0.60 mmol, 1.20 equiv) wurden bei Raumtemperatur in trockenem Dichlormethan (5 ml) vermischt, 8 h bei Raumtemperatur gerührt und nach dieser zeit einmal jeweils 0.5 equiv Acetlychlorid und Triethylamin nachdosiert. 1- (5,5-Dimethyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (109 mg, 0.50 mmol, 1.00 equiv), acetyl chloride (43 mg, 0.55 mmol, 1.10 eqiv) and triethylamine (60 mg, 0.60 mmol, 1.20 equiv) were mixed at room temperature in dry dichloromethane (5 ml), stirred for 8 h at room temperature and after this time 0.5 equiv of acetyl chloride and triethylamine were metered in once.
Anschließend wurde auf gesättigte Natruim-Hydrogencarbonat-Lösung gegeben, über einen It was then added to saturated sodium bicarbonate solution, via a
Phasenseperator getrocknet und das organische Lösunsgmittel unter vermindertem Druck entfernt. Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde [l-(5,5-Dimethyl-Phase separator dried and the organic solvent removed under reduced pressure. Purification by column chromatography (gradient ethyl acetate / heptane) gave [1- (5,5-dimethyl-
4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-acetat (101 mg, 72%) als farbloser Feststoff erhalten. ‘H-NMR (400 MHz, CDC13 d, ppm) 6.99 (s, 1H), 5.92 (s, 1H), 3.39 (d, 1H), 3.28 (d, 1H), 2.16 (s, 3H), 2.04 (s, 3H), 1.44 (s, 3H), 1.40 (s, 3H). No. 1.3-16: [l-(5-Ethyl-5-methyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-acetat 4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] acetate (101 mg, 72%) was obtained as a colorless solid. 'H NMR (400 MHz, CDC1 3 d, ppm) 6.99 (s, 1H), 5.92 (s, 1H), 3.39 (d, 1H), 3.28 (d, 1H), 2.16 (s, 3H), 2.04 (s, 3H), 1.44 (s, 3H), 1.40 (s, 3H). No. 1.3-16: [1- (5-Ethyl-5-methyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] acetate
Figure imgf000054_0002
Figure imgf000054_0002
l-(5-Ethyl-5-methyl-4H-isoxazol-3-yl)-2-hydroxy-3-methyl-2H-pyrrol-5-on (65 mg, 0.28 mmol, 1.00 equiv), Acetlychlorid (24 mg, 0.31 mmol, 1.10 eqiv) und Triethylamin (34 mg, 0.33 mmol, 1.20 equiv) wurden bei Raumtemperatur in trockenem Dichlormethan (5 ml) vermischt, 48 h bei Raumtemperatur gerührt. Anschließend wurde auf gesättigte Natruim-Hydrogencarbonat-Lösung gegeben, über einen Phasenseperator getrocknet und das organische Lösunsgmittel unter vermindertem Druck entfernt.1- (5-Ethyl-5-methyl-4H-isoxazol-3-yl) -2-hydroxy-3-methyl-2H-pyrrol-5-one (65 mg, 0.28 mmol, 1.00 equiv), acetyl chloride (24 mg , 0.31 mmol, 1.10 eqiv) and triethylamine (34 mg, 0.33 mmol, 1.20 equiv) were mixed at room temperature in dry dichloromethane (5 ml), stirred for 48 h at room temperature. It was then added to saturated sodium bicarbonate solution, dried over a phase separator and the organic solvent was removed under reduced pressure.
Durch säulenchromatographische Reinigung (Gradient Ethylacetat/Heptan) wurde [l-(5-Ethyl-5- methyl-4H-isoxazol-3-yl)-3-methyl-5-oxo-2H-pyrrol-2-yl]-acetat (75 mg, 91%) als farbloser Feststoff erhalten.‘H-NMR (400 MHz, CDCI3 d, ppm) 6.98 (s, 1H), 5.92 (s, 1H), 3.41 (d, 1H), 3.27 (d, 1H), 2.16 (s, 3H), 1.94 (s, 3H), 1.68 (m, 2H) 1.37 (s, 3H), 0.96 (m, 3H). Purification by column chromatography (gradient ethyl acetate / heptane) gave [1- (5-ethyl-5-methyl-4H-isoxazol-3-yl) -3-methyl-5-oxo-2H-pyrrol-2-yl] acetate ( 75 mg, 91%) was obtained as a colorless solid.'H-NMR (400 MHz, CDCI 3 d, ppm) 6.98 (s, 1H), 5.92 (s, 1H), 3.41 (d, 1H), 3.27 (d, 1H), 2.16 (s, 3H), 1.94 (s, 3H), 1.68 (m, 2H) 1.37 (s, 3H), 0.96 (m, 3H).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten Heterocyclylpyrrolonen erhält man die nachfolgend genannten Verbindungen. Wenn in Tabelle 1 ein Strukturelement durch eine Strukurformel definiert ist, welches eine gestrichelte Linie enthält, so bedeutet diese gestrichelte Linie, dass an dieser Position die betreffende Gruppe mit dem Rest des Moleküls verbunden ist. In analogy to the production examples given above and recited at the appropriate place and taking into account the general information on the production of substituted ones Heterocyclylpyrrolonen the following compounds are obtained. If in Table 1 a structural element is defined by a structural formula which contains a dashed line, this dashed line means that the group in question is connected to the rest of the molecule at this position.
Figure imgf000055_0001
Figure imgf000055_0001
Tabelle 1.1: Im Speziellen bevorzugte Verbindungen der Formel (1.1) sind die Verbindungen 1.1-1 bis 1.1-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.1-1 bis 1.1-69 der Tabelle 1.1 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.1: Particularly preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.1-1 to 1.1-69 of Table 1.1 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Tabelle 1 : Table 1 :
Figure imgf000055_0002
Figure imgf000056_0001
Figure imgf000057_0003
Figure imgf000055_0002
Figure imgf000056_0001
Figure imgf000057_0003
Figure imgf000057_0001
Tabelle 1.2: Bevorzugte Verbindungen der Formel (1.2) sind die Verbindungen 1.2-1 bis 1.2-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.2-1 bis 1.2- 69 der Tabelle 1.2 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000057_0001
Table 1.2: Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.2-1 to 1.2- 69 of table 1.2 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
Figure imgf000057_0002
Tabelle 1.3: Bevorzugte Verbindungen der Formel (1.3) sind die Verbindungen 1.3-1 bis 1.3-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.3-1 bis 1.3- 69 der Tabelle 1.3 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000057_0002
Table 1.3: Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.3-1 to 1.3- 69 of table 1.3 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1.
Figure imgf000058_0001
Figure imgf000058_0001
Tabelle 1.4: Bevorzugte Verbindungen der Formel (1.4) sind die Verbindungen 1.4-1 bis 1.4-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.4-1 bis 1.4- 69 der Tabelle 1.4 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.4: Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.4-1 to 1.4- 69 of table 1.4 are thus by the meaning of the respective entries no. 1 to 69 defined for Q of Table 1 above.
Figure imgf000058_0002
Tabelle 1.5: Bevorzugte Verbindungen der Formel (1.5) sind die Verbindungen 1.5-1 bis 1.5-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.5-1 bis 1.5- 69 der Tabelle 1.5 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000058_0002
Table 1.5: Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.5-1 to 1.5- 69 of Table 1.5 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000058_0003
Figure imgf000058_0003
Tabelle 1.6: Bevorzugte Verbindungen der Formel (1.6) sind die Verbindungen 1.6-1 bis 1.6-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.6-1 bis 1.6- 69 der Tabelle 1.6 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000059_0001
Table 1.6: Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.6-1 to 1.6- 69 of table 1.6 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000059_0001
Tabelle 1.7: Bevorzugte Verbindungen der Formel (1.7) sind die Verbindungen 1.7-1 bis 1.7-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.7-1 bis 1.7-Table 1.7: Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.7-1 to 1.7-
69 der Tabelle 1.7 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. 69 of Table 1.7 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000059_0002
Figure imgf000059_0002
Tabelle 1.8: Bevorzugte Verbindungen der Formel (1.8) sind die Verbindungen 1.8-1 bis 1.8-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.8-1 bis 1.8- 69 der Tabelle 1.8 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.8: Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.8-1 to 1.8- 69 of Table 1.8 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000059_0003
Figure imgf000059_0003
Tabelle 1.9: Bevorzugte Verbindungen der Formel (1.9) sind die Verbindungen 1.9-1 bis 1.9-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.9-1 bis 1.9- 69 der Tabelle 1.9 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der TabelleTable 1.9: Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.9-1 to 1.9- 69 of Table 1.9 are thus by the meaning of the respective entries No. 1 to 69 for Q of the table
1 definiert.
Figure imgf000060_0001
1 defined.
Figure imgf000060_0001
Tabelle 1.10: Bevorzugte Verbindungen der Formel (1.10) sind die Verbindungen 1.10-1 bis 1.10-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.10-1 bis 1.10-69 der Tabelle 1.10 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.10: Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.10-1 to 1.10-69 of table 1.10 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000060_0002
Tabelle 1.11 : Bevorzugte Verbindungen der Formel (1.11) sind die Verbindungen 1.11-1 bis 1.11-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.11-1 bis 1.11-69 der Tabelle 1.11 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000060_0002
Table 1.11: Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.11-1 to 1.11-69 of table 1.11 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000060_0003
Figure imgf000060_0003
Tabelle 1.12: Bevorzugte Verbindungen der Formel (1.12) sind die Verbindungen 1.12-1 bis 1.12-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.12-1 bis 1.12-69 der Tabelle 1.12 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000061_0001
Table 1.12: Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.12-1 to 1.12-69 of table 1.12 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000061_0001
Tabelle 1.13: Bevorzugte Verbindungen der Formel (1.13) sind die Verbindungen 1.13-1 bis 1.13-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.13-1 bis 1.13-69 der Tabelle 1.13 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.13: Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.13-1 to 1.13-69 of table 1.13 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000061_0002
Tabelle 1.14: Bevorzugte Verbindungen der Formel (1.14) sind die Verbindungen 1.14-1 bis 1.14-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.14-1 bis 1.14-69 der Tabelle 1.14 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000061_0002
Table 1.14: Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.14-1 to 1.14-69 of table 1.14 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000061_0003
Figure imgf000061_0003
Tabelle 1.15: Bevorzugte Verbindungen der Formel (1.15) sind die Verbindungen 1.15-1 bis 1.15-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.15-1 bis 1.15-69 der Tabelle 1.15 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000062_0001
Table 1.15: Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.15-1 to 1.15-69 of table 1.15 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000062_0001
Tabelle 1.16: Bevorzugte Verbindungen der Formel (1.16) sind die Verbindungen 1.16-1 bis 1.16-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.16-1 bis 1.16-69 der Tabelle 1.16 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.16: Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.16-1 to 1.16-69 of table 1.16 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000062_0002
Tabelle 1.17: Bevorzugte Verbindungen der Formel (1.17) sind die Verbindungen 1.17-1 bis 1.17-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.17-1 bis 1.17-69 der Tabelle 1.17 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000062_0002
Table 1.17: Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.17-1 to 1.17-69 of table 1.17 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000062_0003
Figure imgf000062_0003
Tabelle 1.18: Bevorzugte Verbindungen der Formel (1.18) sind die Verbindungen 1.18-1 bis 1.18-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.18-1 bis 1.18-69 der Tabelle 1.18 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000063_0001
Table 1.18: Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.18-1 to 1.18-69 of table 1.18 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000063_0001
Tabelle 1.19: Bevorzugte Verbindungen der Formel (1.19) sind die Verbindungen 1.19-1 bis 1.19-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.19-1 bis 1.19-69 der Tabelle 1.19 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.19: Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.19-1 to 1.19-69 of table 1.19 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000063_0002
Tabelle 1.20: Bevorzugte Verbindungen der Formel (1.20) sind die Verbindungen 1.20-1 bis 1.20-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.20-1 bis 1.20-69 der Tabelle 1.20 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000063_0002
Table 1.20: Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.20-1 to 1.20-69 of table 1.20 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000063_0003
Figure imgf000063_0003
Tabelle 1.21 : Bevorzugte Verbindungen der Formel (1.21) sind die Verbindungen 1.21-1 bis 1.21-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.21-1 bis 1.21-69 der Tabelle 1.21 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000064_0001
Table 1.21: Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.21-1 to 1.21-69 of table 1.21 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000064_0001
Tabelle 1.22: Bevorzugte Verbindungen der Formel (1.22) sind die Verbindungen 1.22-1 bis 1.22-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.22-1 bis 1.22-69 der Tabelle 1.22 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.22: Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.22-1 to 1.22-69 of table 1.22 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000064_0002
Tabelle 1.23: Bevorzugte Verbindungen der Formel (1.23) sind die Verbindungen 1.23-1 bis 1.23-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.23-1 bis 1.23-69 der Tabelle 1.23 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000064_0002
Table 1.23: Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.23-1 to 1.23-69 of table 1.23 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000064_0003
Figure imgf000064_0003
Tabelle 1.24: Bevorzugte Verbindungen der Formel (1.24) sind die Verbindungen 1.24-1 bis 1.24-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.24-1 bis 1.24-69 der Tabelle 1.24 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000065_0001
Table 1.24: Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.24-1 to 1.24-69 of table 1.24 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000065_0001
Tabelle 1.25: Bevorzugte Verbindungen der Formel (1.25) sind die Verbindungen 1.25-1 bis 1.25-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.25-1 bis 1.25-69 der Tabelle 1.25 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.25: Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.25-1 to 1.25-69 of table 1.25 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000065_0002
Tabelle 1.26: Bevorzugte Verbindungen der Formel (1.26) sind die Verbindungen 1.26-1 bis 1.26-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.26-1 bis 1.26-69 der Tabelle 1.26 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000065_0002
Table 1.26: Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.26-1 to 1.26-69 of table 1.26 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000065_0003
Figure imgf000065_0003
Tabelle 1.27: Bevorzugte Verbindungen der Formel (1.27) sind die Verbindungen 1.27-1 bis 1.27-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.27-1 bis 1.27-69 der Tabelle 1.27 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000066_0001
Table 1.27: Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.27-1 to 1.27-69 of table 1.27 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000066_0001
Tabelle 1.28: Bevorzugte Verbindungen der Formel (1.28) sind die Verbindungen 1.28-1 bis 1.28-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.28-1 bis 1.28-69 der Tabelle 1.28 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.28: Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.28-1 to 1.28-69 of table 1.28 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000066_0002
Tabelle 1.29: Bevorzugte Verbindungen der Formel (1.29) sind die Verbindungen 1.29-1 bis 1.29-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.29-1 bis 1.29-69 der Tabelle 1.29 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000066_0002
Table 1.29: Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.29-1 to 1.29-69 of table 1.29 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000066_0003
Figure imgf000066_0003
Tabelle 1.30: Bevorzugte Verbindungen der Formel (1.30) sind die Verbindungen 1.30-1 bis 1.30-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.30-1 bis 1.30-69 der Tabelle 1.30 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000067_0001
Table 1.30: Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.30-1 to 1.30-69 of table 1.30 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000067_0001
Tabelle 1.31 : Bevorzugte Verbindungen der Formel (1.31) sind die Verbindungen 1.31-1 bis 1.31-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.31-1 bis 1.31-69 der Tabelle 1.31 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.31: Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.31-1 to 1.31-69 of table 1.31 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000067_0002
Tabelle 1.32: Bevorzugte Verbindungen der Formel (1.32) sind die Verbindungen 1.32-1 bis 1.32-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.32-1 bis 1.32-69 der Tabelle 1.32 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000067_0002
Table 1.32: Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.32-1 to 1.32-69 of table 1.32 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000067_0003
Figure imgf000067_0003
Tabelle 1.33: Bevorzugte Verbindungen der Formel (1.33) sind die Verbindungen 1.33-1 bis 1.33-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.33-1 bis 1.33-69 der Tabelle 1.33 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000068_0001
Table 1.33: Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.33-1 to 1.33-69 of table 1.33 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000068_0001
Tabelle 1.34: Bevorzugte Verbindungen der Formel (1.34) sind die Verbindungen 1.34-1 bis 1.34-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.34-1 bis 1.34-69 der Tabelle 1.34 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.34: Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.34-1 to 1.34-69 of table 1.34 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000068_0002
Tabelle 1.35: Bevorzugte Verbindungen der Formel (1.35) sind die Verbindungen 1.35-1 bis 1.35-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.35-1 bis 1.35-69 der Tabelle 1.35 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000068_0002
Table 1.35: Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.35-1 to 1.35-69 of table 1.35 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000068_0003
Figure imgf000068_0003
Tabelle 1.36: Bevorzugte Verbindungen der Formel (1.36) sind die Verbindungen 1.36-1 bis 1.36-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.36-1 bis 1.36-69 der Tabelle 1.36 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000069_0001
Table 1.36: Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.36-1 to 1.36-69 of table 1.36 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000069_0001
Tabelle 1.37: Bevorzugte Verbindungen der Formel (1.37) sind die Verbindungen 1.37-1 bis 1.37-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.37-1 bis 1.37-69 der Tabelle 1.37 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.37: Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.37-1 to 1.37-69 of table 1.37 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000069_0002
Tabelle 1.38: Bevorzugte Verbindungen der Formel (1.38) sind die Verbindungen 1.38-1 bis 1.38-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.38-1 bis 1.38-69 der Tabelle 1.38 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000069_0002
Table 1.38: Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.38-1 to 1.38-69 of table 1.38 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000069_0003
Figure imgf000069_0003
Tabelle 1.39: Bevorzugte Verbindungen der Formel (1.39) sind die Verbindungen 1.39-1 bis 1.39-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.39-1 bis 1.39-69 der Tabelle 1.39 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000070_0001
Table 1.39: Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.39-1 to 1.39-69 of table 1.39 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000070_0001
Tabelle 1.40: Bevorzugte Verbindungen der Formel (1.40) sind die Verbindungen 1.40-1 bis 1.40-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.40-1 bis 1.40-69 der Tabelle 1.40 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.40: Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.40-1 to 1.40-69 of table 1.40 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000070_0002
Tabelle 1.41 : Bevorzugte Verbindungen der Formel (1.41) sind die Verbindungen 1.41-1 bis 1.41-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.41-1 bis 1.41-69 der Tabelle 1.41 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000070_0002
Table 1.41: Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.41-1 to 1.41-69 of table 1.41 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000070_0003
Figure imgf000070_0003
Tabelle 1.42: Bevorzugte Verbindungen der Formel (1.42) sind die Verbindungen 1.42-1 bis 1.42-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.42-1 bis 1.42-69 der Tabelle 1.42 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000071_0001
Table 1.42: Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.42-1 to 1.42-69 of table 1.42 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000071_0001
Tabelle 1.43: Bevorzugte Verbindungen der Formel (1.43) sind die Verbindungen 1.43-1 bis 1.43-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.43-1 bis 1.43-69 der Tabelle 1.43 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.43: Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.43-1 to 1.43-69 of table 1.43 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000071_0002
Tabelle 1.44: Bevorzugte Verbindungen der Formel (1.44) sind die Verbindungen 1.44-1 bis 1.44-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.44-1 bis 1.44-69 der Tabelle 1.44 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000071_0002
Table 1.44: Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.44-1 to 1.44-69 in Table 1.44 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000071_0003
Figure imgf000071_0003
Tabelle 1.45: Bevorzugte Verbindungen der Formel (1.45) sind die Verbindungen 1.45-1 bis 1.45-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.45-1 bis 1.45-69 der Tabelle 1.45 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000072_0001
Table 1.45: Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.45-1 to 1.45-69 of table 1.45 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000072_0001
Tabelle 1.46: Bevorzugte Verbindungen der Formel (1.46) sind die Verbindungen 1.46-1 bis 1.46-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.46-1 bis 1.46-69 der Tabelle 1.46 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.46: Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.46-1 to 1.46-69 of table 1.46 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000072_0002
Tabelle 1.47: Bevorzugte Verbindungen der Formel (1.47) sind die Verbindungen 1.47-1 bis 1.47-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.47-1 bis 1.47-69 der Tabelle 1.47 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000072_0002
Table 1.47: Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.47-1 to 1.47-69 of table 1.47 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000072_0003
Figure imgf000072_0003
Tabelle 1.48: Bevorzugte Verbindungen der Formel (1.48) sind die Verbindungen 1.48-1 bis 1.48-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.48-1 bis 1.48-69 der Tabelle 1.48 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000073_0001
Table 1.48: Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.48-1 to 1.48-69 of table 1.48 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000073_0001
Tabelle 1.49: Bevorzugte Verbindungen der Formel (1.49) sind die Verbindungen 1.49-1 bis 1.49-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.49-1 bis 1.49-69 der Tabelle 1.49 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.49: Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.49-1 to 1.49-69 in table 1.49 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
(1-50)(1-50)
Figure imgf000073_0002
Tabelle 1.50: Bevorzugte Verbindungen der Formel (1.50) sind die Verbindungen 1.50-1 bis 1.50-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.50-1 bis 1.50-69 der Tabelle 1.50 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000073_0002
Table 1.50: Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.50-1 to 1.50-69 of table 1.50 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000073_0003
Figure imgf000073_0003
Tabelle 1.51 : Bevorzugte Verbindungen der Formel (1.51) sind die Verbindungen 1.51-1 bis 1.51-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.51-1 bis 1.51-69 der Tabelle 1.51 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000074_0001
Table 1.51: Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.51-1 to 1.51-69 of table 1.51 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000074_0001
Tabelle 1.52: Bevorzugte Verbindungen der Formel (1.52) sind die Verbindungen 1.52-1 bis 1.52-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.52-1 bis 1.52-69 der Tabelle 1.52 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.52: Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.52-1 to 1.52-69 of table 1.52 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000074_0002
Tabelle 1.53: Bevorzugte Verbindungen der Formel (1.53) sind die Verbindungen 1.53-1 bis 1.53-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.53-1 bis 1.53-69 der Tabelle 1.53 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000074_0002
Table 1.53: Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.53-1 to 1.53-69 of table 1.53 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000074_0003
Figure imgf000074_0003
Tabelle 1.54: Bevorzugte Verbindungen der Formel (1.54) sind die Verbindungen 1.54-1 bis 1.54-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.54-1 bis 1.54-69 der Tabelle 1.54 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000075_0001
Table 1.54: Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.54-1 to 1.54-69 of table 1.54 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000075_0001
Tabelle 1.55: Bevorzugte Verbindungen der Formel (1.55) sind die Verbindungen 1.55-1 bis 1.55-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.55-1 bis 1.55-69 der Tabelle 1.55 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.55: Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.55-1 to 1.55-69 of table 1.55 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000075_0002
Tabelle 1.56: Bevorzugte Verbindungen der Formel (1.56) sind die Verbindungen 1.56-1 bis 1.56-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.56-1 bis 1.56-69 der Tabelle 1.56 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000075_0002
Table 1.56: Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.56-1 to 1.56-69 of table 1.56 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000075_0003
Figure imgf000075_0003
Tabelle 1.57: Bevorzugte Verbindungen der Formel (1.57) sind die Verbindungen 1.57-1 bis 1.57-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.57-1 bis 1.57-69 der Tabelle 1.57 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000076_0001
Table 1.57: Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.57-1 to 1.57-69 of table 1.57 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000076_0001
Tabelle 1.58: Bevorzugte Verbindungen der Formel (1.58) sind die Verbindungen 1.58-1 bis 1.58-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.58-1 bis 1.58-69 der Tabelle 1.58 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.58: Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.58-1 to 1.58-69 of table 1.58 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000076_0002
Tabelle 1.59: Bevorzugte Verbindungen der Formel (1.59) sind die Verbindungen 1.59-1 bis 1.59-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.59-1 bis 1.59-69 der Tabelle 1.59 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000076_0002
Table 1.59: Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.59-1 to 1.59-69 of table 1.59 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000076_0003
Figure imgf000076_0003
Tabelle 1.60: Bevorzugte Verbindungen der Formel (1.60) sind die Verbindungen 1.60-1 bis 1.60-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.60-1 bis 1.60-69 der Tabelle 1.60 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000077_0001
Table 1.60: Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.60-1 to 1.60-69 of table 1.60 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000077_0001
Tabelle 1.61 : Bevorzugte Verbindungen der Formel (1.61) sind die Verbindungen 1.61-1 bis 1.61-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.61-1 bis 1.61-69 der Tabelle 1.61 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.61: Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.61-1 to 1.61-69 in table 1.61 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000077_0002
Tabelle 1.62: Bevorzugte Verbindungen der Formel (1.62) sind die Verbindungen 1.62-1 bis 1.62-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.62-1 bis 1.62-69 der Tabelle 1.62 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000077_0002
Table 1.62: Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.62-1 to 1.62-69 of table 1.62 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000077_0003
Figure imgf000077_0003
Tabelle 1.63: Bevorzugte Verbindungen der Formel (1.63) sind die Verbindungen 1.63-1 bis 1.63-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.63-1 bis 1.63-69 der Tabelle 1.63 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.63: Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.63-1 to 1.63-69 of table 1.63 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
(1-64)(1-64)
Figure imgf000077_0004
Tabelle 1.64: Bevorzugte Verbindungen der Formel (1.64) sind die Verbindungen 1.64-1 bis 1.64-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen
Figure imgf000077_0004
Table 1.64: Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.64-1 bis 1.64-69 der Tabelle 1.64 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. 1.64-1 to 1.64-69 of table 1.64 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000078_0001
Figure imgf000078_0001
Tabelle 1.65: Bevorzugte Verbindungen der Formel (1.65) sind die Verbindungen 1.65-1 bis 1.65-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.65: Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.65-1 bis 1.65-69 der Tabelle 1.65 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. 1.65-1 to 1.65-69 of table 1.65 are therefore by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000078_0002
Figure imgf000078_0002
Tabelle 1.66: Bevorzugte Verbindungen der Formel (1.66) sind die Verbindungen 1.66-1 bis 1.66-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.66: Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.66-1 bis 1.66-69 der Tabelle 1.66 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. 1.66-1 to 1.66-69 of Table 1.66 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000078_0003
Figure imgf000078_0003
Tabelle 1.67: Bevorzugte Verbindungen der Formel (1.67) sind die Verbindungen 1.67-1 bis 1.67-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.67-1 bis 1.67-69 der Tabelle 1.67 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.67: Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.67-1 to 1.67-69 of table 1.67 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000079_0001
Figure imgf000079_0001
Tabelle 1.68: Bevorzugte Verbindungen der Formel (1.68) sind die Verbindungen 1.68-1 bis 1.68-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.68-1 bis 1.68-69 der Tabelle 1.68 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.68: Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.68-1 to 1.68-69 of table 1.68 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000079_0002
Figure imgf000079_0002
Tabelle 1.69: Bevorzugte Verbindungen der Formel (1.69) sind die Verbindungen 1.69-1 bis 1.69-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.69-1 bis 1.69-69 der Tabelle 1.69 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.69: Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.69-1 to 1.69-69 in table 1.69 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000079_0003
Tabelle 1.70: Bevorzugte Verbindungen der Formel (1.70) sind die Verbindungen 1.70-1 bis 1.70-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.70-1 bis 1.70-69 der Tabelle 1.70 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000080_0001
Figure imgf000079_0003
Table 1.70: Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.70-1 to 1.70-69 of table 1.70 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000080_0001
Tabelle 1.71 : Bevorzugte Verbindungen der Formel (1.71) sind die Verbindungen 1.71-1 bis 1.71-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.71-1 bis 1.71-69 der Tabelle 1.71 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.71: Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.71-1 to 1.71-69 of table 1.71 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000080_0002
Tabelle 1.72: Bevorzugte Verbindungen der Formel (1.72) sind die Verbindungen 1.72-1 bis 1.72-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.72-1 bis 1.72-69 der Tabelle 1.72 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000080_0002
Table 1.72: Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.72-1 to 1.72-69 in table 1.72 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000080_0003
Figure imgf000080_0003
Tabelle 1.73: Bevorzugte Verbindungen der Formel (1.73) sind die Verbindungen 1.73-1 bis 1.73-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.73-1 bis 1.73-69 der Tabelle 1.73 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000081_0001
Table 1.73: Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.73-1 to 1.73-69 of table 1.73 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000081_0001
Tabelle 1.74: Bevorzugte Verbindungen der Formel (1.74) sind die Verbindungen 1.74-1 bis 1.74-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.74-1 bis 1.74-69 der Tabelle 1.74 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.74: Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.74-1 to 1.74-69 of table 1.74 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000081_0002
Tabelle 1.75: Bevorzugte Verbindungen der Formel (1.75) sind die Verbindungen 1.75-1 bis 1.75-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.75-1 bis 1.75-69 der Tabelle 1.75 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000081_0002
Table 1.75: Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.75-1 to 1.75-69 of table 1.75 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000081_0003
Figure imgf000081_0003
Tabelle 1.76: Bevorzugte Verbindungen der Formel (1.76) sind die Verbindungen 1.76-1 bis 1.76-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.76-1 bis 1.76-69 der Tabelle 1.76 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000082_0001
Table 1.76: Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.76-1 to 1.76-69 of table 1.76 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000082_0001
Tabelle 1.77: Bevorzugte Verbindungen der Formel (1.77) sind die Verbindungen 1.77-1 bis 1.77-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.77-1 bis 1.77-69 der Tabelle 1.77 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.77: Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.77-1 to 1.77-69 of table 1.77 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000082_0002
Tabelle 1.78: Bevorzugte Verbindungen der Formel (1.78) sind die Verbindungen 1.78-1 bis 1.78-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.78-1 bis 1.78-69 der Tabelle 1.78 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000082_0002
Table 1.78: Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.78-1 to 1.78-69 of table 1.78 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000082_0003
Figure imgf000082_0003
Tabelle 1.79: Bevorzugte Verbindungen der Formel (1.79) sind die Verbindungen 1.79-1 bis 1.79-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.79-1 bis 1.79-69 der Tabelle 1.79 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000083_0001
Table 1.79: Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.79-1 to 1.79-69 of table 1.79 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000083_0001
Tabelle 1.80: Bevorzugte Verbindungen der Formel (1.80) sind die Verbindungen 1.80-1 bis 1.80-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.80-1 bis 1.80-69 der Tabelle 1.80 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.80: Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.80-1 to 1.80-69 of table 1.80 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000083_0002
Figure imgf000083_0002
Tabelle 1.81 : Bevorzugte Verbindungen der Formel (1.81) sind die Verbindungen 1.81-1 bis 1.81-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.81-1 bis 1.81-69 der Tabelle 1.81 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.81: Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.81-1 to 1.81-69 of table 1.81 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000083_0003
Figure imgf000083_0003
Tabelle 1.82: Bevorzugte Verbindungen der Formel (1.82) sind die Verbindungen 1.82-1 bis 1.82-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.82-1 bis 1.82-69 der Tabelle 1.82 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000084_0001
Table 1.82: Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.82-1 to 1.82-69 of table 1.82 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000084_0001
Tabelle 1.83: Bevorzugte Verbindungen der Formel (1.83) sind die Verbindungen 1.83-1 bis 1.83-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.83-1 bis 1.83-69 der Tabelle 1.83 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.83: Preferred compounds of the formula (1.83) are the compounds 1.83-1 to 1.83-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.83-1 to 1.83-69 in Table 1.83 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000084_0002
Tabelle 1.84: Bevorzugte Verbindungen der Formel (1.84) sind die Verbindungen 1.84-1 bis 1.84-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.84-1 bis 1.84-69 der Tabelle 1.84 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000084_0002
Table 1.84: Preferred compounds of the formula (1.84) are the compounds 1.84-1 to 1.84-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.84-1 to 1.84-69 of table 1.84 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000084_0003
Figure imgf000084_0003
Tabelle 1.85: Bevorzugte Verbindungen der Formel (1.85) sind die Verbindungen 1.85-1 bis 1.85-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.85-1 bis 1.85-69 der Tabelle 1.85 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000085_0001
Table 1.85: Preferred compounds of the formula (1.85) are the compounds 1.85-1 to 1.85-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.85-1 to 1.85-69 of table 1.85 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000085_0001
Tabelle 1.86: Bevorzugte Verbindungen der Formel (1.86) sind die Verbindungen 1.86-1 bis 1.86-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.86-1 bis 1.86-69 der Tabelle 1.86 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.86: Preferred compounds of the formula (1.86) are the compounds 1.86-1 to 1.86-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.86-1 to 1.86-69 in table 1.86 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000085_0002
Tabelle 1.87: Bevorzugte Verbindungen der Formel (1.87) sind die Verbindungen 1.87-1 bis 1.87-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.87-1 bis 1.87-69 der Tabelle 1.87 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000085_0002
Table 1.87: Preferred compounds of the formula (1.87) are the compounds 1.87-1 to 1.87-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.87-1 to 1.87-69 in Table 1.87 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000085_0003
Figure imgf000085_0003
Tabelle 1.88: Bevorzugte Verbindungen der Formel (1.88) sind die Verbindungen 1.88-1 bis 1.88-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.88-1 bis 1.88-69 der Tabelle 1.88 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000086_0001
Table 1.88: Preferred compounds of the formula (1.88) are the compounds 1.88-1 to 1.88-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.88-1 to 1.88-69 in table 1.88 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000086_0001
Tabelle 1.89: Bevorzugte Verbindungen der Formel (1.89) sind die Verbindungen 1.89-1 bis 1.89-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.89-1 bis 1.89-69 der Tabelle 1.89 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.89: Preferred compounds of the formula (1.89) are the compounds 1.89-1 to 1.89-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.89-1 to 1.89-69 of table 1.89 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000086_0002
Tabelle 1.90: Bevorzugte Verbindungen der Formel (1.90) sind die Verbindungen 1.90-1 bis 1.90-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.90-1 bis 1.90-69 der Tabelle 1.90 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000086_0002
Table 1.90: Preferred compounds of the formula (1.90) are the compounds 1.90-1 to 1.90-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.90-1 to 1.90-69 of table 1.90 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000086_0003
Figure imgf000086_0003
Tabelle 1.91 : Bevorzugte Verbindungen der Formel (1.91) sind die Verbindungen 1.91-1 bis 1.91-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.91-1 bis 1.91-69 der Tabelle 1.91 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000087_0001
Table 1.91: Preferred compounds of the formula (1.91) are the compounds 1.91-1 to 1.91-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.91-1 to 1.91-69 of table 1.91 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000087_0001
Tabelle 1.92: Bevorzugte Verbindungen der Formel (1.92) sind die Verbindungen 1.92-1 bis 1.92-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.92-1 bis 1.92-69 der Tabelle 1.92 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.92: Preferred compounds of the formula (1.92) are the compounds 1.92-1 to 1.92-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.92-1 to 1.92-69 in table 1.92 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000087_0002
Tabelle 1.93: Bevorzugte Verbindungen der Formel (1.93) sind die Verbindungen 1.93-1 bis 1.93-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.93-1 bis 1.93-69 der Tabelle 1.93 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000087_0002
Table 1.93: Preferred compounds of the formula (1.93) are the compounds 1.93-1 to 1.93-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.93-1 to 1.93-69 in table 1.93 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000087_0003
Figure imgf000087_0003
Tabelle 1.94: Bevorzugte Verbindungen der Formel (1.94) sind die Verbindungen 1.94-1 bis 1.94-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.94-1 bis 1.94-69 der Tabelle 1.94 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.94: Preferred compounds of the formula (1.94) are the compounds 1.94-1 to 1.94-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.94-1 to 1.94-69 in table 1.94 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000087_0004
Tabelle 1.95: Bevorzugte Verbindungen der Formel (1.95) sind die Verbindungen 1.95-1 bis 1.95-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen
Figure imgf000087_0004
Table 1.95: Preferred compounds of the formula (1.95) are the compounds 1.95-1 to 1.95-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.95-1 bis 1.95-69 der Tabelle 1.95 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. 1.95-1 to 1.95-69 of table 1.95 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000088_0001
Figure imgf000088_0001
Tabelle 1.96: Bevorzugte Verbindungen der Formel (1.96) sind die Verbindungen 1.96-1 bis 1.96-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.96: Preferred compounds of the formula (1.96) are the compounds 1.96-1 to 1.96-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.96-1 bis 1.96-69 der Tabelle 1.96 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. 1.96-1 to 1.96-69 of Table 1.96 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000088_0002
Figure imgf000088_0002
Tabelle 1.97: Bevorzugte Verbindungen der Formel (1.97) sind die Verbindungen 1.97-1 bis 1.97-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.97: Preferred compounds of the formula (1.97) are the compounds 1.97-1 to 1.97-69, in which Q has the meanings of Table 1 given in the respective row. The connections
1.97-1 bis 1.97-69 der Tabelle 1.97 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. 1.97-1 to 1.97-69 of Table 1.97 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
Figure imgf000088_0003
Figure imgf000088_0003
Tabelle 1.98: Bevorzugte Verbindungen der Formel (1.98) sind die Verbindungen 1.98-1 bis 1.98-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.98-1 bis 1.98-69 der Tabelle 1.98 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.98: Preferred compounds of the formula (1.98) are the compounds 1.98-1 to 1.98-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.98-1 to 1.98-69 of table 1.98 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000089_0001
Figure imgf000089_0001
Tabelle 1.99: Bevorzugte Verbindungen der Formel (1.99) sind die Verbindungen 1.99-1 bis 1.99-69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.99-1 bis 1.99-69 der Tabelle 1.99 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. Table 1.99: Preferred compounds of the formula (1.99) are the compounds 1.99-1 to 1.99-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1.99-1 to 1.99-69 of table 1.99 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
(1.100)(1.100)
Figure imgf000089_0002
Figure imgf000089_0002
Tabelle 1.100: Bevorzugte Verbindungen der Formel (I. 100) sind die Verbindungen I. 100-1 bis I. 100- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 100-1 bis I. 100-69 der Tabelle I. 100 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.100: Preferred compounds of the formula (I. 100) are the compounds I. 100-1 to I. 100- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 100-1 to I. 100-69 of Table I. 100 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.101)(1.101)
Figure imgf000089_0003
Tabelle 1.101 : Bevorzugte Verbindungen der Formel (1.101) sind die Verbindungen 1. 101-1 bis 1. 101- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 101-1 bis I. 101-69 der Tabelle I. 101 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert. (1.102)
Figure imgf000089_0003
Table 1.101: Preferred compounds of the formula (1.101) are the compounds 1. 101-1 to 1. 101- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 101-1 to I. 101-69 of Table I. 101 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1. (1,102)
Figure imgf000090_0001
Figure imgf000090_0001
Tabelle 1.102: Bevorzugte Verbindungen der Formel (I. 102) sind die Verbindungen I. 102-1 bis I. 102- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 102-1 bis I. 102-69 der Tabelle I. 102 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.102: Preferred compounds of the formula (I. 102) are the compounds I. 102-1 to I. 102- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 102-1 to I. 102-69 of table I. 102 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000090_0002
Tabelle 1.103: Bevorzugte Verbindungen der Formel (1.103) sind die Verbindungen I. 103-1 bis I. 103- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 103-1 bis I. 103-69 der Tabelle I. 103 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der Tabelle 1 definiert.
Figure imgf000090_0002
Table 1.103: Preferred compounds of the formula (1.103) are the compounds I. 103-1 to I. 103- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 103-1 to I. 103-69 of table I. 103 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1.
(1.104)(1,104)
Figure imgf000090_0003
Figure imgf000090_0003
Tabelle 1.104: Bevorzugte Verbindungen der Formel (1. 104) sind die Verbindungen 1. 104-1 bis 1. 104- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 104-1 bis 1. 104-69 der Tabelle 1. 104 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000091_0001
Table 1.104: Preferred compounds of the formula (1. 104) are the compounds 1. 104-1 to 1. 104- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 104-1 to 1. 104-69 of table 1. 104 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000091_0001
Tabelle 1.105: Bevorzugte Verbindungen der Formel (I. 105) sind die Verbindungen I. 105-1 bis I. 105- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 105-1 bis I. 105-69 der Tabelle I. 105 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.105: Preferred compounds of the formula (I. 105) are the compounds I. 105-1 to I. 105- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 105-1 to I. 105-69 of Table I. 105 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000091_0002
Tabelle 1.106: Bevorzugte Verbindungen der Formel (I. 106) sind die Verbindungen I. 106-1 bis I. 106- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 106-1 bis I. 106-69 der Tabelle I. 106 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000091_0002
Table 1.106: Preferred compounds of the formula (I. 106) are the compounds I. 106-1 to I. 106- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 106-1 to I. 106-69 of Table I. 106 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.107)(1,107)
Figure imgf000091_0003
Figure imgf000091_0003
Tabelle 1.107: Bevorzugte Verbindungen der Formel (I. 107) sind die Verbindungen I. 107-1 bis I. 107- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 107-1 bis I. 107-69 der Tabelle I. 107 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.108)Table 1.107: Preferred compounds of the formula (I. 107) are the compounds I. 107-1 to I. 107- 69, in which Q has the meanings of Table 1 given in the respective row. The compounds I. 107-1 to I. 107-69 of Table I. 107 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.108)
Figure imgf000092_0001
Figure imgf000092_0001
Tabelle 1.108: Bevorzugte Verbindungen der Formel (I. 108) sind die Verbindungen I. 108-1 bis I. 108- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 108-1 bis I. 108-69 der Tabelle I. 108 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.108: Preferred compounds of the formula (I. 108) are the compounds I. 108-1 to I. 108- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 108-1 to I. 108-69 of Table I. 108 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000092_0002
Tabelle 1.109: Bevorzugte Verbindungen der Formel (1. 109) sind die Verbindungen 1. 109-1 bis 1. 109- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 109-1 bis 1. 109-69 der Tabelle 1. 109 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000092_0002
Table 1.109: Preferred compounds of the formula (1. 109) are the compounds 1. 109-1 to 1. 109- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 109-1 to 1. 109-69 of table 1. 109 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.110)(1.110)
Figure imgf000092_0003
Figure imgf000092_0003
Tabelle 1.110: Bevorzugte Verbindungen der Formel (I. 110) sind die Verbindungen I. 110-1 bis I. 110- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 110-1 bis I. 110-69 der Tabelle I. 110 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000093_0001
Table 1.110: Preferred compounds of the formula (I.110) are the compounds I.110-1 to I.110-69, in which Q has the meanings of Table 1 given in the respective row. The connections I.110-1 to I.110-69 of Table I.110 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000093_0001
Tabelle 1.111 : Bevorzugte Verbindungen der Formel (I. 111) sind die Verbindungen I. 111-1 bis I. 111- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 111-1 bis I. 111-69 der Tabelle I. 111 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.111: Preferred compounds of the formula (I. 111) are the compounds I. 111-1 to I. 111- 69, in which Q has the meanings of Table 1 given in the respective row. The compounds I. 111-1 to I. 111-69 of Table I. 111 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000093_0002
Tabelle 1.112: Bevorzugte Verbindungen der Formel (I. 112) sind die Verbindungen I. 112-1 bis I. 112- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 112-1 bis I. 112-69 der Tabelle I. 112 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000093_0002
Table 1.112: Preferred compounds of the formula (I. 112) are the compounds I. 112-1 to I. 112- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 112-1 to I. 112-69 of Table I. 112 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000093_0003
Figure imgf000093_0003
Tabelle 1.113: Bevorzugte Verbindungen der Formel (1. 113) sind die Verbindungen 1. 113-1 bis 1. 113- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 113-1 bis 1. 113-69 der Tabelle 1. 113 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.114)Table 1.113: Preferred compounds of the formula (1. 113) are the compounds 1. 113-1 to 1. 113- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 113-1 to 1. 113-69 of Table 1. 113 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,114)
Figure imgf000094_0001
Figure imgf000094_0001
Tabelle 1.114: Bevorzugte Verbindungen der Formel (1. 114) sind die Verbindungen 1. 114-1 bis 1. 114- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 114-1 bis 1. 114-69 der Tabelle 1. 114 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.114: Preferred compounds of the formula (1. 114) are the compounds 1. 114-1 to 1. 114- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 114-1 to 1. 114-69 of Table 1. 114 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000094_0002
Tabelle 1.115: Bevorzugte Verbindungen der Formel (I. 115) sind die Verbindungen I. 115-1 bis I. 115- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 115-1 bis I. 115-69 der Tabelle I. 115 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000094_0002
Table 1.115: Preferred compounds of the formula (I. 115) are the compounds I. 115-1 to I. 115- 69, in which Q has the meanings of Table 1 given in the respective row. The compounds I. 115-1 to I. 115-69 of Table I. 115 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.116)(1.116)
Figure imgf000094_0003
Figure imgf000094_0003
Tabelle 1.116: Bevorzugte Verbindungen der Formel (I. 116) sind die Verbindungen I. 116-1 bis I. 116- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 116-1 bis I. 116-69 der Tabelle I. 116 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000095_0001
Table 1.116: Preferred compounds of the formula (I. 116) are the compounds I. 116-1 to I. 116- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 116-1 to I. 116-69 of Table I. 116 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000095_0001
Tabelle 1.117: Bevorzugte Verbindungen der Formel (I. 117) sind die Verbindungen I. 117-1 bis I. 117- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 117-1 bis I. 117-69 der Tabelle I. 117 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.117: Preferred compounds of the formula (I. 117) are the compounds I. 117-1 to I. 117- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 117-1 to I. 117-69 of Table I. 117 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000095_0002
Tabelle 1.118: Bevorzugte Verbindungen der Formel (I. 118) sind die Verbindungen I. 118-1 bis I. 118- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 118-1 bis I. 118-69 der Tabelle I. 118 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000095_0002
Table 1.118: Preferred compounds of the formula (I. 118) are the compounds I. 118-1 to I. 118- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 118-1 to I. 118-69 of Table I. 118 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000095_0003
Figure imgf000095_0003
Tabelle 1.119: Bevorzugte Verbindungen der Formel (1. 119) sind die Verbindungen 1. 119-1 bis 1. 119- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 119-1 bis 1. 119-69 der Tabelle 1. 119 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.120)Table 1,119: Preferred compounds of the formula (1,119) are the compounds 1,119-1 to 1,119-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 119-1 to 1. 119-69 of Table 1. 119 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,120)
Figure imgf000096_0001
Figure imgf000096_0001
Tabelle 1.120: Bevorzugte Verbindungen der Formel (I. 120) sind die Verbindungen I. 120-1 bis I. 120- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 120-1 bis I. 120-69 der Tabelle I. 120 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.120: Preferred compounds of the formula (I.120) are the compounds I.120-1 to I.120-69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 120-1 to I. 120-69 of Table I. 120 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000096_0002
Tabelle 1.121 : Bevorzugte Verbindungen der Formel (I. 121) sind die Verbindungen I. 121-1 bis I. 121- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 121-1 bis I. 121-69 der Tabelle I. 121 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000096_0002
Table 1,121: Preferred compounds of the formula (I. 121) are the compounds I. 121-1 to I. 121- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 121-1 to I. 121-69 of Table I. 121 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.122)(1,122)
Figure imgf000096_0003
Figure imgf000096_0003
Tabelle 1.122: Bevorzugte Verbindungen der Formel (I. 122) sind die Verbindungen I. 122-1 bis I. 122- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 122-1 bis I. 122-69 der Tabelle I. 122 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000097_0001
Table 1.122: Preferred compounds of the formula (I. 122) are the compounds I. 122-1 to I. 122- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 122-1 to I. 122-69 of Table I. 122 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000097_0001
Tabelle 1.123: Bevorzugte Verbindungen der Formel (I. 123) sind die Verbindungen I. 123-1 bis I. 123- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 123-1 bis I. 123-69 der Tabelle I. 123 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.123: Preferred compounds of the formula (I. 123) are the compounds I. 123-1 to I. 123- 69, in which Q has the meanings of Table 1 given in the respective row. The compounds I. 123-1 to I. 123-69 of Table I. 123 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000097_0002
Tabelle 1.124: Bevorzugte Verbindungen der Formel (I. 124) sind die Verbindungen I. 124-1 bis I. 124- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 124-1 bis I. 124-69 der Tabelle I. 124 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000097_0002
Table 1,124: Preferred compounds of the formula (I. 124) are the compounds I. 124-1 to I. 124- 69, in which Q has the meanings of Table 1 given in the respective row. The compounds I. 124-1 to I. 124-69 of Table I. 124 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000097_0003
Figure imgf000097_0003
Tabelle 1.125: Bevorzugte Verbindungen der Formel (1. 125) sind die Verbindungen 1. 125-1 bis 1. 125- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 125-1 bis 1. 125-69 der Tabelle 1. 125 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.126)Table 1,125: Preferred compounds of the formula (1,125) are the compounds 1,125-1 to 1,125-69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 125-1 to 1. 125-69 of Table 1. 125 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.126)
Figure imgf000098_0001
Figure imgf000098_0001
Tabelle 1.126: Bevorzugte Verbindungen der Formel (I. 126) sind die Verbindungen I. 126-1 bis I. 126- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 126-1 bis I. 126-69 der Tabelle I. 126 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1,126: Preferred compounds of the formula (I. 126) are the compounds I. 126-1 to I. 126- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 126-1 to I. 126-69 of Table I. 126 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000098_0002
Tabelle 1.127: Bevorzugte Verbindungen der Formel (I. 127) sind die Verbindungen I. 127-1 bis I. 127- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 127-1 bis I. 127-69 der Tabelle I. 127 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000098_0002
Table 1,127: Preferred compounds of the formula (I 127) are the compounds I 127-1 to I 127- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 127-1 to I. 127-69 of Table I. 127 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
Figure imgf000098_0003
Figure imgf000098_0003
Tabelle 1.128: Bevorzugte Verbindungen der Formel (I. 128) sind die Verbindungen I. 128-1 bis I. 128- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 128-1 bis I. 128-69 der Tabelle I. 128 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.129)Table 1.128: Preferred compounds of the formula (I. 128) are the compounds I. 128-1 to I. 128- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 128-1 to I. 128-69 of Table I. 128 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,129)
Figure imgf000099_0001
Figure imgf000099_0001
Tabelle 1.129: Bevorzugte Verbindungen der Formel (I. 129) sind die Verbindungen I. 129-1 bis I. 129- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 129-1 bis I. 129-69 der Tabelle I. 129 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1,129: Preferred compounds of the formula (I. 129) are the compounds I. 129-1 to I. 129- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 129-1 to I. 129-69 of Table I. 129 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.130)(1.130)
Figure imgf000099_0002
Tabelle 1.130: Bevorzugte Verbindungen der Formel (I. 130) sind die Verbindungen I. 130-1 bis I. 130- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 130-1 bis I. 130-69 der Tabelle I. 130 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000099_0002
Table 1.130: Preferred compounds of the formula (I.130) are the compounds I.130-1 to I.130-69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 130-1 to I. 130-69 of Table I. 130 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.131)(1,131)
Figure imgf000099_0003
Figure imgf000099_0003
Tabelle 1.131 : Bevorzugte Verbindungen der Formel (1. 131) sind die Verbindungen 1. 131-1 bis 1. 131- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 131-1 bis 1. 131-69 der Tabelle 1. 131 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.132)Table 1.131: Preferred compounds of the formula (1. 131) are the compounds 1. 131-1 to 1. 131- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 131-1 to 1. 131-69 of table 1. 131 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1,132)
Figure imgf000100_0001
Figure imgf000100_0001
Tabelle 1.132: Bevorzugte Verbindungen der Formel (I. 132) sind die Verbindungen I. 132-1 bis I. 132- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 132-1 bis I. 132-69 der Tabelle I. 132 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.132: Preferred compounds of the formula (I. 132) are the compounds I. 132-1 to I. 132- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 132-1 to I. 132-69 of Table I. 132 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.133)(1,133)
Figure imgf000100_0002
Tabelle 1.133: Bevorzugte Verbindungen der Formel (I. 133) sind die Verbindungen I. 133-1 bis I. 133- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 133-1 bis I. 133-69 der Tabelle I. 133 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000100_0002
Table 1.133: Preferred compounds of the formula (I. 133) are the compounds I. 133-1 to I. 133- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 133-1 to I. 133-69 of Table I. 133 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.134)(1,134)
Figure imgf000100_0003
Figure imgf000100_0003
Tabelle 1.134: Bevorzugte Verbindungen der Formel (I. 134) sind die Verbindungen I. 134-1 bis I. 134- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 134-1 bis I. 134-69 der Tabelle I. 134 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. (1.135)Table 1.134: Preferred compounds of the formula (I. 134) are the compounds I. 134-1 to I. 134- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 134-1 to I. 134-69 of Table I. 134 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. (1.135)
Figure imgf000101_0001
Figure imgf000101_0001
Tabelle 1.135: Bevorzugte Verbindungen der Formel (I. 135) sind die Verbindungen I. 135-1 bis I. 135- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 135-1 bis I. 135-69 der Tabelle I. 135 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Table 1.135: Preferred compounds of the formula (I. 135) are the compounds I. 135-1 to I. 135- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 135-1 to I. 135-69 of Table I. 135 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.136)(1,136)
Figure imgf000101_0002
Tabelle 1.136: Bevorzugte Verbindungen der Formel (I. 136) sind die Verbindungen I. 136-1 bis I. 136- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen I. 136-1 bis I. 136-69 der Tabelle I. 136 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000101_0002
Table 1.136: Preferred compounds of the formula (I. 136) are the compounds I. 136-1 to I. 136- 69, in which Q has the meanings of Table 1 given in the respective row. The connections I. 136-1 to I. 136-69 of Table I. 136 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above.
(1.137)(1,137)
Figure imgf000101_0003
Figure imgf000101_0003
Tabelle 1.137: Bevorzugte Verbindungen der Formel (1. 137) sind die Verbindungen 1. 137-1 bis 1. 137- 69, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1. 137-1 bis 1. 137-69 der Tabelle 1. 137 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 69 für Q der oben stehenden Tabelle 1 definiert. Spektroskopische Daten ausgewählter Tabellenbeispiele: Table 1.137: Preferred compounds of the formula (1. 137) are the compounds 1. 137-1 to 1. 137- 69, in which Q has the meanings of Table 1 given in the respective row. The connections 1. 137-1 to 1. 137-69 of Table 1. 137 are thus by the meaning of the respective entries No. 1 to 69 defined for Q of Table 1 above. Spectroscopic data from selected table examples:
Die nachfolgend aufgeführten spektroskopischen Daten ausgewählter Tabellenbeispiele wurden über klassische H-NMR-Intcrprctation ausgewertet. a) Klassische H-NM R-Intcrprctation The spectroscopic data of selected table examples listed below were evaluated using classic H-NMR interpretation. a) Classic H-NM R interpretation
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
Figure imgf000102_0001
Figure imgf000103_0001
Figure imgf000104_0001
Figure imgf000105_0001
b) NMR-Peak-Listenverfahren Die lH-NMR-Daten ausgewählter Beispiele werden in Form von lH-NMR-Peaklisten notiert. Zu jedem Signalpeak wird erst der d-Wert in ppm und dann die Signalintensität in runden Klammem aufgeführt. Die d-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. b) NMR Peak List Method The 1 H-NMR data of selected examples are noted in the form of 1 H-NMR peak lists. For each signal peak, the d-value is listed in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated by semicolons.
Die Peakliste eines Beispieles hat daher die Form: di (Intensität^; d2 (Intensität2); ; d; (Intensität^; ; d (Intensität^ Die Intensität scharfer Signale korreliert mit der Höhe der Signale in einem gedruckten Beispiel eines NMR-Spektrums in cm und zeigt die wirklichen Verhältnisse der Signalintensitäten. Bei breiten Signalen können mehrere Peaks oder die Mitte des Signals und ihre relative Intensität im Vergleich zum intensivsten Signal im Spektrum gezeigt werden. The peak list of an example therefore has the form: di (intensity ^; d2 (intensity2);; d; (intensity ^;; d (intensity ^ The intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the real relationships of the signal intensities. For wide signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
Zur Kalibrierung der chemischen Verschiebung von lH-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des Lösungsmittels, besondem im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak Vorkommen, muss es aber nicht. To calibrate the chemical shift of 1H NMR spectra, we use tetramethylsilane and / or the chemical shift of the solvent, especially in the case of spectra measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peak lists, but it does not have to.
Die Listen der lH-NMR-Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden. The lists of the 1H-NMR peaks are similar to the classic 1H-NMR printouts and thus usually contain all the peaks which are listed in a classic NMR interpretation.
Darüber hinaus können sie wie klassische 1H-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. In addition, like classic 1H NMR printouts, they can show solvent signals, signals from stereoisomers of the target compounds, which are also a subject of the invention, and / or peaks of impurities.
Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von lH-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-DÖ und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe lntensität aufweisen. When indicating connection signals in the delta range of solvents and / or water, our lists of 1 H-NMR peaks show the usual solvent peaks, for example peaks of DMSO in DMSO-D Ö and the peak of water, which are usually in the Have a high intensity on average.
Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere lntensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90%). The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have a lower intensity on average than the peaks of the target compounds (for example with a purity of> 90%).
Solche Stereoisomere und/oder Verunreinigungen können typisch für das jeweilige Such stereoisomers and / or impurities can be typical of each
Herstellungsverfahren sein lhre Peaks können somit dabei helfen, die Reproduktion unseres Manufacturing process so your peaks can help reproduce our
Herstellungsverfahrens anhand von“Nebenprodukt-Fingerabdrücken” zu erkennen. Recognize manufacturing process based on "by-product fingerprints".
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche lntensitätsfilter eingesetzt werden. Diese lsolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- lnterpretation. An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also using empirically evaluated expected values) can isolate the peaks of the target compounds as required, using additional intensity filters if necessary. This isolation would be similar to the relevant peak picking in the classic 1H NMR interpretation.
Weitere Details zu lH-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden.
Figure imgf000107_0001
Figure imgf000108_0001
Figure imgf000109_0001
Figure imgf000110_0001
Figure imgf000111_0001
Further details on 1H NMR peak lists can be found in Research Disclosure Database Number 564025.
Figure imgf000107_0001
Figure imgf000108_0001
Figure imgf000109_0001
Figure imgf000110_0001
Figure imgf000111_0001
Gegenstand der vorliegenden Erfindung ist weiterhin die Verwendung einer oder mehrerer The present invention furthermore relates to the use of one or more
Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze, jeweils wie oben definiert,  Compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1,137) and / or their salts, each as defined above,
als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen.  as a herbicide and / or plant growth regulator, preferably in crops of useful and / or ornamental plants.
Gegenstand der vorliegenden Erfindung ist ferner ein Verfahren zur Bekämpfung von Schadpflanzen und/oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten The present invention also relates to a method for controlling harmful plants and / or for regulating the growth of plants, characterized in that an effective amount one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the preferred or particularly preferred
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, auf die (Schad)Pflanzen, (Schad)Pflanzensamen, den Boden, in dem oder auf dem die (Schad)Pflanzen wachsen, oder die Anbaufläche appliziert wird. Design, in particular one or more compounds of the formulas (1.1) to (1.137) and / or their salts, each as defined above, or an agent according to the invention, as defined below, onto the (harmful) plants, (harmful) plant seeds, the soil , in or on which the (harmful) plants grow, or the cultivated area is applied.
Gegenstand der vorliegenden Erfindung ist auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen, vorzugsweise in Nutzpflanzenkulturen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (I) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten The present invention also relates to a method for controlling unwanted plants, preferably in crops of useful plants, characterized in that an effective amount of one or more compounds of the general formula (I) and / or their salts, as defined above, preferably in one of the as preferably or particularly preferably marked
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, auf unerwünschte Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut der unerwünschten Pflanzen (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die unerwünschte Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die unerwünschte Pflanzen wachsen werden) appliziert wird. Design, in particular one or more compounds of the formulas (1.1) to (1.137) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, on undesired plants (for example harmful plants such as mono- or dicotyledon weeds or undesirable plants Crops), the seeds of the unwanted plants (ie plant seeds, e.g. grains, seeds or vegetative propagation organs such as tubers or shoots with buds), the soil in or on which the unwanted plants grow (e.g. the soil of cultivated or non-cultivated land ) or the cultivated area (ie area on which the unwanted plants will grow) is applied.
Gegenstand der vorliegenden Erfindung ist ferner auch Verfahren zur Bekämpfung zur The present invention also relates to methods for combating
Wachstumsregulierung von Pflanzen, vorzugsweise von Nutzpflanzen, dadurch gekennzeichnet, dass eine wirksame Menge einer oder mehrerer Verbindungen der allgemeinen Formel (1) und/oder deren Salzen, wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten Regulation of the growth of plants, preferably of useful plants, characterized in that an effective amount of one or more compounds of the general formula (1) and / or their salts, as defined above, is preferably in one of those designated as preferred or particularly preferred
Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze, jeweils wie oben definiert, oder eines erfindungsgemäßen Mittels, wie nachstehend definiert, die Pflanze, das Saatgut der Pflanze (d.h. Pflanzensamen, z.B. Körner, Samen oder vegetative Design, in particular one or more compounds of the formulas (1.1) to (1.137) and / or their salts, in each case as defined above, or an agent according to the invention, as defined below, the plant, the seed of the plant (ie plant seeds, eg grains, seeds or vegetative
Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen), den Boden, in dem oder auf dem die Pflanzen wachsen, (z.B. den Boden von Kulturland oder Nicht-Kulturland) oder die Anbaufläche (d.h. Fläche, auf der die Pflanzen wachsen werden) appliziert wird. Propagation organs such as tubers or shoots with buds), the soil in or on which the plants grow (e.g. the soil of cultivated or non-cultivated land) or the area under cultivation (i.e. the area on which the plants will grow) is applied.
Dabei können die erfindungsgemäßen Verbindungen bzw. die erfindungsgemäßen Mittel z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- und/oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen The compounds according to the invention or the agents according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or post-emergence methods. Some representatives of the mono- and dicotyledons are examples
Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Weed flora, which can be used to control the compounds according to the invention, without any restriction to certain species being mentioned.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von The present invention therefore also relates to a method for combating
unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in undesirable plants or for regulating the growth of plants, preferably in
Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Plant crops in which one or more compound (s) according to the invention is applied to the plants (for example harmful plants such as monocotyledonous or dicotyledon weeds or undesirable crop plants), the seeds (for example grains, seeds or vegetative propagation organs such as tubers or shoots with buds) or the area which the plants grow (e.g. the area under cultivation). The compounds according to the invention can e.g. are applied in the pre-sowing (possibly also by incorporation into the soil), pre-emergence or post-emergence methods. Some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned in detail, which can be controlled by the compounds according to the invention, without any intention that the name should limit them to certain species.
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echino- chloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum. Monocotyledonous harmful plants of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echino- chloa, Eleocharis, Eleusine, Eragrostis, Festuchera, Eriochaerochimbras, Eriocharimeter, Eriochaistlo, Eriochaistro, Eriochaistlo, Eriochaistlo, Eriocha, f , Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Unkräuter der Gattungen: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. Werden die erfindungsgemäßen Verbindungen vor dem Keimen der Schadpflanzen (Ungräser und/oder Unkräuter) auf die Erdoberfläche appliziert (Vorauflaufverfahren), so wird entweder das Auflaufen der Ungras- bzw. Unkrautkeimlinge vollständig verhindert oder diese wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab. Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Gexhoris, Erysimum, Erysimum , Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindemia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senec , Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium. If the compounds according to the invention are applied to the earth's surface prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), then either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage, but then they grow and eventually die completely after three to four weeks.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. When the active ingredients are applied to the green parts of the plants in the post-emergence process, growth stops after the treatment and the harmful plants remain at the growth stage at the time of application or die completely after a certain time, so that weed competition which is harmful to the crop plants is very early and is permanently eliminated.
Die erfindungsgemäßen Verbindungen können in Nutzkulturen Selektivitäten aufweisen und können auch als nichtselektive Herbizide eingesetzt werden. The compounds according to the invention can have selectivities in crops and can also be used as non-selective herbicides.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,Although the compounds according to the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crop plants of economically important crops are e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie Pisum, Solanum, Vicia, or monocotyledon cultures of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea, depending on the structure of the respective compound according to the invention and its application rate only insignificantly or not harmed at all. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in crops such as
landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. agricultural crops or ornamental crops.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten in der Agrarindustrie verwendeten Wirkstoff , vor allem bestimmten Herbiziden, Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of known or still to be developed genetically modified plants. The transgenic plants are generally notable for particularly advantageous properties, for example resistance to certain active ingredients used in the agricultural industry, especially certain herbicides,
Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten lnsekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller lnhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Weitere besondere Eigenschaften liegen in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung. Resistance to plant diseases or pathogens such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to the crop, for example, in terms of quantity, quality, storability, composition and special ingredients. Thus, transgenic plants with an increased starch content or altered starch quality or with a different fatty acid composition of the crop are known. Further special properties are tolerance or resistance to abiotic stressors such as heat, cold, dryness, salt and ultraviolet radiation.
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z.B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. Die Verbindungen der allgemeinen Formel (I) können als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht wurden. Preference is given to using the compounds of the general formula (I) according to the invention or their salts in economically important transgenic crops of useful and ornamental plants, e.g. of cereals such as wheat, barley, rye, oats, millet, rice and corn or also crops of sugar beet, cotton, soybeans, rapeseed, potatoes, tomatoes, peas and other vegetables. The compounds of the general formula (I) can be used as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Vorzugsweise können die Verbindungen der allgemeinen Formel (I) als Herbizide in  The compounds of the general formula (I) can preferably be used as herbicides in
Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind. Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Conventional ways of producing new plants which have modified properties in comparison to previously occurring plants are, for example, classic ones
Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z.B. EP 0221044, EP 0131624). Beschrieben wurden beispielsweise in mehreren Fällen gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z.B. WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z.B. EP 0242236 A, EP 0242246 A) oder Glyphosate (WO 92/000377 A) oder der Sulfonylharnstoffe (EP 0257993 A, US 5,013,659) oder gegen Kombinationen oder Breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be created using genetic engineering methods (see e.g. EP 0221044, EP 0131624). For example, in several cases, genetic engineering modifications of crop plants for the purpose of modifying the starch synthesized in the plants (for example WO 92/011376 A, WO 92/014827 A, WO 91/019806 A), transgenic crop plants which are active against certain herbicides of the glufosinate see, for example, EP 0242236 A, EP 0242246 A) or glyphosate (WO 92/000377 A) or the sulfonylureas (EP 0257993 A, US 5,013,659) or against combinations or
Mischungen dieser Herbizide durch„gene stacking“ resistent sind, wie transgenen Kulturpflanzen z. B. Mais oder Soja mit dem Handelsnamen oder der Bezeichnung Optimum™ GAT™ (Glyphosate ALS Tolerant). Mixtures of these herbicides are resistant by “gene stacking”, such as transgenic crops. B. corn or soy with the trade name or the designation Optimum ™ GAT ™ (Glyphosate ALS Tolerant).
transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis- Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen (EP 0142924 A, EP 0193259 A).  transgenic crop plants, for example cotton, with the ability to produce Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP 0142924 A, EP 0193259 A).
transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/013972 A).  transgenic crop plants with modified fatty acid composition (WO 91/013972 A).
gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z.B. neuen Phytoalexinen, die eine erhöhte Krankheitsresistenz verursachen (EP 0309862 A, EP 0464461 A) gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EP 0305398 A)  genetically modified crops with new ingredients or secondary substances e.g. new phytoalexins that cause increased resistance to disease (EP 0309862 A, EP 0464461 A) genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EP 0305398 A)
transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming“)  transgenic crop plants that produce pharmaceutically or diagnostically important proteins (“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“) transgenic crops that are characterized by higher yields or better quality transgenic crop plants which are characterized by a combination of, for example, the new properties mentioned above (“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. In principle, numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known; see e.g. I. Potrykus and 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). Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg or 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 Laboratory Manual, 2. Aufl. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996 For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombining DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. Adapters or linkers can be attached to the fragments for connecting the DNA fragments to one another, see e.g. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene and Clones", VCH Weinheim 2nd edition 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 Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, 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. The production of plant cells with a reduced activity of a gene product can be achieved, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to achieve a cosuppression effect or the expression of at least one appropriately constructed ribozyme which specifically cleaves transcripts of the above-mentioned gene product. For this purpose, DNA molecules can be used that comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules that only comprise parts of the coding sequence, these parts having to be long enough to be in the cells to cause an antisense effect. It is also possible to use DNA sequences which have a high degree of homology to the coding sequences of a gene product, but which are not completely identical.
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. 11 (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 Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen When nucleic acid molecules are expressed in plants, the synthesized protein can be located in any compartment of the plant cell. However, in order to achieve localization in a specific compartment, the coding region can be linked, for example, to DNA sequences which ensure localization in a specific compartment. Such sequences are known to the person skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1: 95-106 (1991). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells. The transgenic plant cells can be regenerated into whole plants using known techniques. In principle, the transgenic plants can be any plants
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 aufweisen. Act plant species, i.e. both monocot and dicot plants. Thus, transgenic plants are available which have changed properties due to overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. 2,4-D, Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z.B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, oder gegen beliebige Kombinationen dieser Wirkstoffe, resistent sind. The compounds of the general formula (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. 2,4-D, dicamba or against herbicides, the essential plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenyl pyruvate dioxygenases (HPPD), respectively against herbicides from the group of the sulfonylureas, the glyphosates, glufosinates or benzoylisoxazoles and analogous active substances, or against any combination of these active substances, or against any combination of these active substances.
Besonders bevorzugt können die erfindungsgemäßen Verbindungen in transgenen Kulturpflanzen eingesetzt werden, die gegen eine Kombination von Glyphosaten und Glufosinaten, Glyphosaten und Sulfonylharnstoffen oder Imidazolinonen resistent sind. Ganz besonders bevorzugt können die erfindungsgemäßen Verbindungen in transgenen Kulturpflanzen wie z. B. Mais oder Soja mit dem Handelsnamen oder der Bezeichnung OptimumTM GATTM (Glyphosate ALS Tolerant) eingesetzt werden. The compounds according to the invention can particularly preferably be used in transgenic crop plants which are resistant to a combination of glyphosates and glufosinates, glyphosates and sulfonylureas or imidazolinones. The compounds according to the invention can very particularly preferably be used in transgenic crop plants such as, for. B. corn or soy with the trade name or the designation OptimumTM GATTM (Glyphosate ALS Tolerant) can be used.
Bei der Anwendung der erfindungsgemäßen Wirkstoffe 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 Aufwandmengen, 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. When the active compounds according to the invention are used in transgenic crops, in addition to the effects on harmful plants which can be observed in other crops, effects often occur which are specific to the application in the respective transgenic culture, for example a changed or specially expanded weed spectrum which can be controlled changed Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing the growth and yield of the transgenic crop plants.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen. The invention therefore also relates to the use of the compounds of the general formula (I) according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
Bevorzugt ist die Verwendung in Getreide, dabei vorzugsweise Mais, Weizen, Gerste, Roggen, Hafer, Hirse, oder Reis, im Vor- oder Nachauflauf. Preference is given to use in cereals, preferably maize, wheat, barley, rye, oats, millet or rice, in the pre- or post-emergence.
Bevorzugt ist auch die Verwendung in Soja im Vor- oder Nachauflauf. Die erfindungsgemäße Verwendung zur Bekämpfung von Schadpflanzen oder zur Pre-or post-soya use is also preferred. The use according to the invention for controlling harmful plants or
Wachstumsregulierung von Pflanzen schließt auch den Fall ein, bei dem der Wirkstoff der allgemeinen Formel (I) oder dessen Salz erst nach der Ausbringung auf der Pflanze, in der Pflanze oder im Boden aus einer Vorläufersubstanz ("Prodrug") gebildet wird. Plant growth regulation also includes the case in which the active ingredient of the general formula (I) or its salt is formed from a precursor substance (“prodrug”) only after application to the plant, in the plant or in the soil.
Gegenstand der Erfindung ist auch die Verwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) oder deren Salzen bzw. eines erfindungsgemäßen Mittels (wie nachstehend definiert) (in einem Verfahren) zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehreren Verbindungen der allgemeinen Formel (I) oder deren Salzen auf die Pflanzen (Schadpflanzen, ggf. zusammen mit den Nutzpflanzen) Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert.  The invention also relates to the use of one or more compounds of the general formula (I) or their salts or an agent according to the invention (as defined below) (in a process) for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount of one or more compounds of the general formula (I) or their salts is applied to the plants (harmful plants, if appropriate together with the useful plants), plant seeds, the soil in or on which the plants grow, or the cultivated area.
Gegenstand der Erfindung ist auch ein herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel The invention also relates to a herbicidal and / or plant growth-regulating agent, characterized in that the agent
(a) eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthält wie oben definiert, vorzugsweise in einer der als bevorzugt bzw. besonders bevorzugt gekennzeichneten (a) contains one or more compounds of the general formula (I) and / or their salts as defined above, preferably in one of those identified as preferred or particularly preferred
Ausgestaltung, insbesondere eine oder mehrere Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze, jeweils wie oben definiert, Design, in particular one or more compounds of the formulas (1.1) to (1.137) and / or their salts, in each case as defined above,
und and
(b) ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii): (b) one or more further substances selected from groups (i) and / or (ii):
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden (d.h. solche, die nicht der oben definierten allgemeinen Formel (I) entsprechen), Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides (ie those which do not correspond to the general formula (I) defined above), fungicides, safeners, fertilizers and / or other growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. (ii) one or more formulation auxiliaries customary in crop protection.
Die weiteren agrochemischen wirksamen Stoffe des Bestandteils (i) eines erfindungsgemäßen Mittels sind dabei vorzugsweise ausgewählt aus der Gruppe der Stoffe, die in "The Pesticide Manual", l6th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2012 genannt sind. The further agrochemically active substances of component (i) of an agent according to the invention are preferably selected from the group of substances described in "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012.
Ein erfindungsgemäßes herbizides oder pflanzenwachstumsregulierendes Mittel, umfasst vorzugsweise ein, zwei, drei oder mehr im Pflanzenschutz übliche Formulierungshilfsmittel (ii) ausgewählt aus der Gruppe bestehend aus Tensiden, Emulgatoren, Dispergiermitteln, Filmbildnem, Verdickungsmitteln, anorganischen Salzen, Stäubemitteln, bei 25 °C und 1013 mbar festen Trägerstoffen, vorzugsweise adsorptionsfähigen, granulierten Inertmaterialien, Netzmitteln, Antioxidationsmitteln, Stabilisatoren, Puffersubstanzen, Antischaummitteln, Wasser, organischen Lösungsmitteln, vorzugsweise bei 25 °C und 1013 mbar mit Wasser in jedem beliebigen Verhältnis mischbare organische Lösungsmittel. A herbicidal or plant growth-regulating agent according to the invention preferably comprises one, two, three or more formulation auxiliaries (ii) selected in plant protection selected from the group consisting of surfactants, emulsifiers, dispersants, film formers, thickeners, inorganic salts, dusts, at 25 ° C and 1013 mbar solid carriers, preferably adsorbable, granulated inert materials, wetting agents, antioxidants, stabilizers, buffer substances, anti-foaming agents, water, organic solvents, preferably at 25 ° C and 1013 mbar with water in any ratio miscible organic solvents.
Die erfindungsgemäßen Verbindungen können in Form von Spritzpulvem, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oder Granulaten in den üblichen Zubereitungen angewendet werden. Gegenstand der Erfindung sind deshalb auch herbizide und pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten. The compounds according to the invention can be used in the customary formulations in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or granules. The invention therefore also relates to herbicidal and plant growth-regulating compositions which comprise the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. As
Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-Öl-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse. Formulation options are possible, for example: wettable powder (WP), water-soluble powder (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water and water-in-oil emulsions, sprayable solutions, Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions, capsule suspensions (CS), dusts (DP), pickling agents, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie",  These individual formulation types are known in principle and are described, for example, in: Winnacker-Küchler, "Chemical Technology",
Band 7, C. Hanser Verlag München, 4. Aufl. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.  Volume 7, C. Hanser Verlag Munich, 4th ed. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen,
"Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of
Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive  Surface Active Agents ", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt," interfacial active
Äthylenoxidaddukte", Wiss. Verlagsgesell., Stutgart 1976; Winnacker-Küchler, "Chemische Ethylene oxide adducts ", Wiss. Verlagsgesellschaft., Stutgart 1976; Winnacker-Küchler," Chemical
Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemiteln und/oder Wachstumsregulatoren hersteilen, z.B. in Form einer Fertigformulierung oder als Tankmix. On the basis of these formulations, combinations with other pesticidally active substances, such as insecticides, acaricides, herbicides, fungicides, as well as with safeners and fertilizers, can also be carried out and / or produce growth regulators, for example in the form of a finished formulation or as a tank mix.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Spray powders are preparations which are uniformly dispersible in water and which, in addition to the active substance, contain not only a diluent or an inert substance, but also ionic and / or nonionic surfactants (wetting agents,
Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt. Dispersants), e.g. polyoxyethylated alkylphenols, polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, ligninsulfonic acid sodium, 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium, sodium dibutylnaphthalene-sulfonic acid sodium or else sodium. To produce the wettable powders, the herbicidal active ingredients are, for example, finely ground in customary equipment, such as hammer mills, fan mills and air jet mills, and mixed at the same time or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, Xylol oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Emulsifiable concentrates are made by dissolving the active ingredient in an organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants of ionic and / or nonionic type (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as
Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters,
Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Alkylaryl polyglycol ether, fatty alcohol polyglycol ether,
Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, S orbitanester wie z.B.  Propylene oxide-ethylene oxide condensation products, alkyl polyethers, orbital esters such as e.g.
Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Sorbitan fatty acid esters or polyoxethylene sorbitan esters such as e.g. Polyoxyethylene.
Stäubemittel erhält man durch Vermahlen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Dusts are obtained by grinding the active ingredient with finely divided solid substances, e.g.
Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß- Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden. Suspension concentrates can be water or oil based. You can, for example, by wet grinding using commercially available bead mills and optionally adding surfactants such as those e.g. already listed above for the other types of formulation.
Emulsionen, z.B. Öl-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Emulsions, e.g. Oil-in-water emulsions (EW) can be mixed using stirrers,
Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Colloid mills and / or static mixers using aqueous organic
Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hersteilen. Solvents and optionally surfactants, e.g. already listed above for the other formulation types.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen von Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates using adhesives, for example polyvinyl alcohol, polyacrylic acid sodium or mineral oils, to the surface of Carriers such as sand, kaolinite or granulated inert material. Suitable active ingredients can also be granulated in the manner customary for the production of fertilizer granules, if desired in a mixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischem und Extrusion ohne festes Inertmaterial hergestellt. Water-dispersible granules are generally produced using the customary processes, such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in For the production of plate, fluidized bed, extruder and spray granules, see e.g. Procedure in
"Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57. "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; "Perry's Chemical Engineer's Handbook," 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103. For more details on the formulation of crop protection products see e.g. G.C. Klingman, "Weed Control as a Science," John Wiley and Sons, Inc., New York, 1961, pp. 81-96, and J.D. Freyer, S.A. Evans, "Weed Control Handbook," 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen. The agrochemical preparations generally contain 0.1 to 99% by weight, in particular 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvem beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige  The active substance concentration in wettable powders is e.g. about 10 to 90 wt .-%, the rest of 100 wt .-% consists of conventional formulation components. In the case of emulsifiable concentrates, the active substance concentration can be about 1 to 90, preferably 5 to 80,% by weight. Powdery
Formulierungen enthalten Formulations included
1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei  1 to 30% by weight of active ingredient, preferably mostly 5 to 20% by weight of active ingredient, sprayable solutions contain about 0.05 to 80, preferably 2 to 50% by weight of active ingredient. at
wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%. Water-dispersible granules, the active ingredient content depends in part on whether the active compound is liquid or solid and which granulation aids, fillers, etc. are used. The active ingredient content of the water-dispersible granules is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel. Formulierangsbeispiele a) Ein Stäubemitel wird erhalten, indem man 10 Gew. -Teile einer Verbindung der allgemeinen Formel (I) und/oder deren Salze und 90 Gew. -Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert. b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 In addition, the active ingredient formulations mentioned may contain the customary adhesives, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity. Formulation examples a) A dust is obtained by mixing 10 parts by weight of a compound of the general formula (I) and / or its salts and 90 parts by weight of talc as an inert substance and comminuting in a hammer mill. b) A wettable powder which is readily dispersible in water is obtained by 25
Gewichtsteile einer Verbindung der allgemeinen Formel (I) und/oder deren Salze, 64  Parts by weight of a compound of general formula (I) and / or its salts, 64
Gew. -Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und Parts by weight of quartz containing kaolin as an inert substance, 10 parts by weight of potassium lignosulfonate and
1 Gew. -Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt. c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Mix 1 part by weight of oleoylmethyl tauric acid sodium as wetting and dispersing agent and grind in a pin mill. c) A dispersion concentrate which is easily dispersible in water is obtained by 20
Gew. -Teile einer Verbindung der allgemeinen Formel (I) und/oder deren Salze mit 6  Parts by weight of a compound of general formula (I) and / or its salts with 6
Gew. -Teilen Alkylphenolpolyglykolether (®Triton X 207), 3 Gew. -Teilen  Parts by weight of alkylphenol polyglycol ether (®Triton X 207), 3 parts by weight
Isotridecanolpolyglykolether (8 EO) und 71 Gew. -Teilen paraffinischem Mineralöl  Isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil
(Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt. d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew. -Teilen einer Verbindung der  (Boiling range e.g. approx. 255 to over 277 C) mixed and ground in a friction ball mill to a fineness of less than 5 microns. d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of
allgemeinen Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmitel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator. e) Ein in Wasser dispergierbares Granulat wird erhalten indem man  general formula (I) and / or their salts, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of oxyethylated nonylphenol as emulsifier. e) A water-dispersible granulate is obtained by
75 Gew. -Teile einer Verbindung der allgemeinen Formel (I) und/oder deren Salze,  75 parts by weight of a compound of the general formula (I) and / or salts thereof,
10 Gew. -Teile ligninsulfonsaures Calcium,  10 parts by weight of calcium lignosulfonic acid,
5 Gew. -Teile Natriumlaurylsulfat,  5 parts by weight of sodium lauryl sulfate,
3 Gew. -Teile Polyvinylalkohol und  3 parts by weight of polyvinyl alcohol and
7 Gew. -Teile Kaolin  7 parts by weight of kaolin
mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. f) Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man  mixes, grinds on a pin mill and granulates the powder in a fluidized bed by spraying water as granulating liquid. f) A water-dispersible granulate is also obtained by
25 Gew. -Teile einer Verbindung der allgemeinen Formel (I) und/oder deren Salze,  25 parts by weight of a compound of the general formula (I) and / or salts thereof,
5 Gew. -Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium  5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid sodium
2 Gew. -Teile oleoylmethyltaurinsaures Natrium,  2 parts by weight of sodium oleoylmethyl taurine,
1 Gew. -Teil Polyvinylalkohol, 17 Gew. -Teile Calciumcarbonat und 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and
50 Gew. -Teile Wasser  50 parts by weight of water
auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet.  homogenized on a colloid mill and pre-comminuted, then ground on a bead mill and the suspension thus obtained is atomized and dried in a spray tower using a single-component nozzle.
Die Verbindungen der allgemeinen Formel (I) oder deren Salze können als solche oder in Form ihrer Zubereitungen (Formulierungen) mit anderen pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Nematiziden, Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder The compounds of general formula (I) or their salts can be used as such or in the form of their preparations (formulations) with other pesticidally active substances, e.g. Insecticides, acaricides, nematicides, herbicides, fungicides, safeners, fertilizers and / or
Wachstumsregulatoren kombiniert eingesetzt werden, z.B. als Fertigformulierung oder als Growth regulators can be used in combination, e.g. as a finished formulation or as
Tankmischungen. Die Kombinationsformulierungen können dabei auf Basis der obengenannten Formulierungen hergestellt werden, wobei die physikalischen Eigenschaften und Stabilitäten der zu kombinierenden Wirkstoffe zu berücksichtigen sind. Tank mixes. The combination formulations can be prepared on the basis of the formulations mentioned above, taking into account the physical properties and stabilities of the active compounds to be combined.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer lnhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat- Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase,  As a combination partner for the compounds according to the invention in mixture formulations or in a tank mix, there are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenyl pyruvate dioxygenase, phytoendesaturase,
Photosystem I, Photosystem 11 oder Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", l6th edition, The British Crop Protection Council und the Royal Soc. of Chemistry, 2006 und dort zitierter Literatur beschrieben sind. Nachfolgend werden beispielhaft bekannte Herbizide oder Pflanzenwachstumsregulatoren genannt, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, wobei diese Wirkstoffe entweder mit ihrem "common name" in der englischsprachigen Variante gemäß lntemational Organization for Standardization (1SO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische lsomere umfaßt, auch wenn diese nicht explizit erwähnt sind. Photosystem I, Photosystem 11 or protoporphyrinogen oxidase are used, e.g. from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2006 and the literature cited therein. In the following, known herbicides or plant growth regulators are mentioned by way of example, which can be combined with the compounds according to the invention, these active compounds either with their "common name" in the English-language variant according to the International Organization for Standardization (1SO) or with the chemical name or with the code number are designated. All forms of use such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers are always included, even if these are not explicitly mentioned.
Beispiele für solche herbiziden Mischungspartner sind: Examples of such herbicidal mixture partners are:
Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclo- pyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate und - octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, 3-[5-Chlor-4- (trifluormethyl)pyridin-2-yl] -4-hydroxy- 1 -methylimidazolidin-2-on, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D- butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, - isopropylammonium, -potassium, -triisopropanolammonium und -trolamine, 2,4-DB, 2,4-DB-butyl, - dimethylammonium, isooctyl, -potassium und -sodium, daimuron (dymron), dalapon, dazomet, n- decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4- dimethyl- 1 ,2-oxazolidin-3 -one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl- 1 ,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat- dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethamet- sulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen- ethyl, ethoxysulfuron, etobenzanid, F- 9600, F-5231, i.e. N-[2-Chlor-4-fluor-5-[4-(3-fluorpropyl)-4,5-dihydro-5-oxo-lH-tetrazol-l-yl]-phenyl]- ethansulfonamid, F-7967, i.e. 3-[7-Chlor-5-fluor-2-(trifluormethyl)-lH-benzimidazol-4-yl]-l -methyl-6- (trifluormethyl)pyrimidin-2,4(lH,3H)-dion, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P- ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M- methyl, flazasulfuron, florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-P, fluazifop -butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr- ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium und -methyl, fluoroglycofen, fluoroglycofen- ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P- ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropyl Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim- sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-ammonium, aminopolachyramethyl, aminopolachyridium amyl amine aminate amine amine amine amine amine aminate amine amine amine amine amine amine amine aminophenachloromethyl amine aminate amine amine amine amine amine amine amine aminocyclopyrachloromethyl amine amine amine amine amine aminocyclopyrachloromethyl amine amine amine aminocyclopyrachloromethane atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafosac-sodium, bispyribac-sodium, bispyrimac-bis, sodium, bispyribac-bis, sodium, bispyryrac-bis, sodium, bispyribac-bis, sodium, bispyryrac-bisp, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and - octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurene, chlorofuronol, chlorofuronol, chlorofuronol, chlorofuronol, chlorofuronol, chlorofuronol chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorothal-dimethyl, chlorosulfuron, 3- [5-chloro-4- (trifluoromethyl) pyridin-2-yl] -4-hydroxy-1-methylimidazolidin-2-one, cinidon, cinidon-ethyl , cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyranil, cyclopydimamuron, cyclopyrimimyl, cyclopyrimimyl, cyclopyrimimyl, cyclopyrimimyl, cyclopyrimimyl, halopyl , 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamine, -ethyl, 2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium and -trolamine, 2 , 4-DB, 2,4-DB-butyl, - dimethylammoni um, isooctyl, potassium and sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4- dimethyl-1, 2-oxazolidin-3-one, 2- (2,5-dichlorobenzyl) -4,4-dimethyl-1, 2-oxazolidin-3-one, dichloroprop, dichloroprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, dipomido, dididate, diquatidate, diquatidate, diquatidate, diquate DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, ethamet-sulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F- 9600, F-5231, ie N- [2-chloro-4- fluoro-5- [4- (3-fluoropropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] phenyl] ethanesulfonamide, F-7967, ie 3- [7-chloro-5 -fluoro-2- (trifluoromethyl) -lH-benzimidazol-4-yl] -l -methyl-6- (trifluoromethyl) pyri midin-2,4 (lH, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron , florasulam, florpyrauxifen, florpyrauxifen-benzyl, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenploracyl-pentamyl-pentamyl-pentamyl-pentamyl-pentamethyl-pentamethyl-pentamethyl-pentamyl , flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fleptyluthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxuthyret, fluroxypyr , fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropyl
ammonium, -diammonium, -dimethylammonium, -potassium, -sodium und -trimesium, H-9201, i.e. O- (2,4-Dimethyl-6-nitrophenyl)-0-ethyl-isopropylphosphoramidothioat, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1- (Dimethoxyphosphoryl)-ethyl-(2,4-dichlorphenoxy)acetat, 4-Hydroxy-l-methoxy-5-methyl-3-[4- (trifluormethyl)pyridin-2-yl]imidazolidin-2-on, 4-Hydroxy-l-methyl-3-[4-(trifluormethyl)pyridin-2- yl]imidazolidin-2-on, imazamethabenz, Imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin- ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium und sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(Difluormethyl)-l- methyl-3-(trifluormethyl)- 1 H-pyrazol-4-yl]methyl} sulfonyl)-5,5-dimethyl-4,5-dihydro- 1 ,2-oxazol, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium und -sodium, MCPB, MCPB-methyl, -ethyl und -sodium, mecoprop, mecoprop-sodium, und -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl und -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, ammonium, -diammonium, -dimethylammonium, -potassium, -sodium and -trimesium, H-9201, ie O- (2,4-dimethyl-6-nitrophenyl) -0-ethyl-isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, ie 1- (dimethoxyphosphoryl) -ethyl- (2, 4-dichlorophenoxy) acetate, 4-hydroxy-l-methoxy-5-methyl-3- [4- (trifluoromethyl) pyridin-2-yl] imidazolidin-2-one, 4-hydroxy-l-methyl-3- [4 - (trifluoromethyl) pyridin-2-yl] imidazolidin-2-one, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynilil , isoproturon, isouron, isoxaben, isoxaflutole, carbutilate, KUH-043, ie 3 - ({[5- (difluoromethyl) -l-methyl-3- (trifluoromethyl) - 1 H-pyrazol-4-yl] methyl} sulfonyl) -5,5-dimethyl-4,5-dihydro-1, 2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, - isopropylammonium, -potassium and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron -methyl, mesotrione,
methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron,
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-[3-chlor-4-(l-methylethyl)- phenyl]-2-methylpentanamid, NGGC-011, napropamide, NC-310, i.e. 4-(2,4-Dichlorbenzoyl)-l-methyl- 5-benzyloxypyrazol, neburon, nicosulfuron, nonanoic acid (Pelargonsäure), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, prop- isochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazo- sulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz- propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrion, sulfentrazone, sulfo- meturon, sulfometuron-methyl, sulfosulfuron, , SYN-523, SYP-249, i.e. l-Ethoxy-3-methyl-l-oxobut- 3-en-2-yl-5-[2-chlor-4-(trifluormethyl)phenoxy]-2-nitrobenzoat, SYP-300, i.e. l-[7-Fluor-3-oxo-4- (prop-2-in-l-yl)-3,4-dihydro-2H-l,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidin-4,5-dion, 2,3,6- TBA, TCA (Trifluoressigsäure), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vemolate, ZJ-0862, i.e. 3,4-Dichlor-N-{2-[(4,6- dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen:
Figure imgf000126_0001
methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinate, monolinuron, monosulfuron, MT-59-chloro-3-ester -4- (l-methylethyl) phenyl] -2-methylpentanamide, NGGC-011, napropamide, NC-310, ie 4- (2,4-dichlorobenzoyl) -l-methyl-5-benzyloxypyrazole, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxotrione (lancotrione), oxyfluorfen, paraquat, paraquat dichloride, pebulate, pentoxachulone phenol pethoxamide, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, prop-isochone, propoxy arbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazo-sulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribyl-pyribylbenzam, pyribyl-pyribylbenzam, pyribyl-pyribylbenzam, pyribyl-pyribylbenzam, pyribyl-pyribamobenzyl-pyribyl-pyribamobenzyl-pyribyl-pyribyl-benzib-pyribyl-pyribamobenzyl-pyribyl-pyribyl-benzib-pyribyl-pyribyl-pyribyl-pyribamobenzyl-pyribyl-pyribyl-pyribamobenzyl-pyribyl-pyribyl-pyribyl-pyribenzyl-Pyribyl-Pyribyl-Pyribyl-Pyribenzyl-Pyribyl-Pyribenzyl , pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofofop-P, Piz -tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron,, SYN-523, SYP-249, ie l-ethoxy-3-methyl-l-oxobut - 3-en-2-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzoate, SYP-300, ie l- [7-fluoro-3-oxo-4- (prop-2 -in-l-yl) -3,4-dihydro-2H-l, 4-benzoxazin-6-yl] -3-propyl-2-thioxoimidazolidin-4,5-dione, 2,3,6-TBA, TCA (Trifluoroacetic acid), TCA-sodium, te buthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, thioxalatealk, tolamacalalk, tafimimatecarb, tafimimatecarb, tiafenolamate, tiafenolamate, tolamate carbolate, tolamacal, carbohydrate triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron-08, urolate N, dichloro Z, dichloro, dichloro, dichloro, dichloro {2 - [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following compounds:
Figure imgf000126_0001
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Examples of plant growth regulators as possible mixing partners are:
Acibenzolar, acibenzolar-S-methyl, 5-Aminolävulinsäure, ancymidol, 6-benzylaminopurine, Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine,
Brassinolid, Catechin, chlormequat chloride, cloprop, cyclanilide, 3-(Cycloprop-l-enyl)propionsäure, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal- dipotassium, -disodium, und mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4- indol-3-ylbutyric acid, isoprothiolane, probenazole, Jasmonsäure, Jasmonsäuremethylester, maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2-(l-naphthyl)acetamide, 1 -naphthylacetic acid, 2- naphthyloxyacetic acid, nitrophenolate-mixture, 4-Oxo-4[(2-phenylethyl)amino]buttersäure, paclobutrazol, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, Salicylsäure, Strigolacton, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.  Brassinolide, catechin, chlormequat chloride, cloprop, cyclanilide, 3- (cycloprop-l-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and mono (N, N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, jasmonic acid , maleic hydrazide, mepiquat chloride, 1 -methylcyclopropene, 2- (l-naphthyl) acetamide, 1 -naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, 4-oxo-4 [(2-phenylethyl) amino] butyric acid, paclobutrazole , N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.
Safener, die in Kombination mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und ggf. in Kombinationen mit weiteren Wirkstoffen wie z.B. Insektiziden, Akariziden, Herbiziden,Safeners which, in combination with the compounds of the general formula (I) according to the invention and, if appropriate, in combinations with other active compounds, Insecticides, acaricides, herbicides,
Fungiziden wie oben aufgelistet, eingesetzt werden können, sind vorzugsweise ausgewählt aus der Gruppe bestehend aus: Fungicides as listed above can preferably be selected from the group consisting of:
S 1 ) V erbindungen der F ormel (S 1 ), S 1) compounds of the formula (S 1),
Figure imgf000126_0002
wobei die Symbole und lndizes folgende Bedeutungen haben: nA ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3;
Figure imgf000126_0002
where the symbols and indices have the following meanings: n A is a natural number from 0 to 5, preferably 0 to 3;
RA 1 ist Halogen, (Ci-C4)Alkyl, (Ci-C i)Alkoxy, Nitro oder (Ci-C4)Haloalkyl; R A 1 is halogen, (Ci-C 4 ) alkyl, (Ci-C i) alkoxy, nitro or (Ci-C 4 ) haloalkyl;
WA ist ein unsubstituierter oder substituierter divalenter heterocyclischer Rest aus der Gruppe der teilungesättigten oder aromatischen Fünfring-Heterocyclen mit 1 bis 3 Heteroringatomen aus der Gruppe N und O, wobei mindestens ein N-Atom und höchstens ein O-Atom im Ring enthalten ist, vorzugsweise ein Rest aus der Gruppe (WA 1) bis (WA 4), W A is an unsubstituted or substituted divalent heterocyclic radical from the group of the unsaturated or aromatic five-membered heterocycles having 1 to 3 hetero ring atoms from the group N and O, with at least one N atom and at most one O atom being contained in the ring, preferably a residue from the group (W A 1 ) to (W A 4 ),
Figure imgf000127_0001
n ist 0 oder 1 ;
Figure imgf000127_0001
n is 0 or 1;
RA 2 ist ORA 3, SRA 3 oder NRA 3RA 4 oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger R A 2 is OR A 3 , SR A 3 or NR A 3 R A 4 or a saturated or unsaturated 3- to 7-membered
Heterocyclus mit mindestens einem N-Atom und bis zu 3 Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (Sl) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C i)Alkyl, (Ci-C i)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORA 3, NHRA 4 oder N(CH3)2, insbesondere der Formel ORA3; Heterocycle with at least one N atom and up to 3 heteroatoms, preferably from the groups O and S, which is connected via the N atom to the carbonyl group in (S1) and is unsubstituted or by residues from the group (Ci-C i) Alkyl, (Ci-C i) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR A 3 , NHR A 4 or N (CH3) 2, in particular of the formula ORA 3 ;
RA 3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; R A 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
RA 4 ist Wasserstoff, (Ci-C6)Alkyl, (Ci-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; R A 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
RA 5 ist H, (Ci-C8)Alkyl, (Ci-C8)Haloalkyl, (Ci-C4)Alkoxy(Ci-C8)Alkyl, Cyano oder COORA 9, worin RA 9 Wasserstoff, (Ci-C8)Alkyl, (Ci-C8)Haloalkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, (Ci-C6)Hydroxyalkyl, (C3-Ci2)Cycloalkyl oder Tri-(Ci-C4)-alkyl-silyl ist; R A 5 is H, (Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy (Ci-C 8 ) alkyl, cyano or COOR A 9 , where R A 9 is hydrogen, ( Ci-C 8 ) alkyl, (Ci-C 8 ) haloalkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (Ci-C 6 ) hydroxyalkyl, (C3-Ci2) cycloalkyl or tri- (Ci -C 4 ) alkyl silyl;
RA 6, RA 7, RA 8 sind gleich oder verschieden Wasserstoff, (Ci-Cs)Alkyl, (Ci-Cs)Haloalkyl, (C3- Ci2)Cycloalkyl oder substituiertes oder unsubstituiertes Phenyl; vorzugsweise: a) Verbindungen vom Typ der Dichlorphenylpyrazolin-3-carbonsäure (Sla), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure,R A 6 , R A 7 , R A 8 are identical or different hydrogen, (Ci-Cs) alkyl, (Ci-Cs) haloalkyl, (C3-Ci2) cycloalkyl or substituted or unsubstituted phenyl; preferably: a) compounds of the dichlorophenylpyrazoline-3-carboxylic acid (Sl a ) type, preferably compounds such as 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid,
1 -(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäureethylester (S 1 - 1 ) ("Mefenpyr-diethyl"), und verwandte Verbindungen, wie sie in der WO-A-91/07874 beschrieben sind; b) Derivate der Dichlorphenylpyrazolcarbonsäure (Slb), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-methyl-pyrazol-3-carbonsäureethylester (S 1 -2), 1 - (2,4-dichlorophenyl) -5- (ethoxycarbonyl) -5-methyl-2-pyrazoline-3-carboxylic acid ethyl ester (S 1 - 1) ("Mefenpyr-diethyl"), and related compounds, as described in WO -A-91/07874; b) derivatives of dichlorophenylpyrazole carboxylic acid (S1 b ), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-methyl-pyrazole-3-carboxylic acid ethyl ester (S 1 -2),
1 -(2,4-Dichlorphenyl)-5-isopropyl-pyrazol-3 -carbonsäureethylester (S 1 -3),  1 - (2,4-dichlorophenyl) -5-isopropyl-pyrazol-3-carboxylic acid ethyl ester (S 1 -3),
1 -(2,4-Dichlorphenyl)-5-(l , 1 -dimethyl-ethyl)pyrazol-3-carbonsäureethyl-ester (S 1 -4) und verwandte Verbindungen, wie sie in EP-A-333 131 und EP-A-269 806 beschrieben sind; c) Derivate der l,5-Diphenylpyrazol-3-carbonsäure (Slc), vorzugsweise Verbindungen wie 1 -(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (S 1 -5), 1 - (2,4-dichlorophenyl) -5- (1,1-dimethyl-ethyl) pyrazole-3-carboxylic acid ethyl ester (S 1 -4) and related compounds as described in EP-A-333 131 and EP- A-269 806; c) derivatives of 1,5-diphenylpyrazole-3-carboxylic acid (S1 c ), preferably compounds such as 1 - (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylic acid ethyl ester (S 1 -5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (Sl-6) und verwandte Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind; d) Verbindungen vom Typ der Triazolcarbonsäuren (Sld), vorzugsweise Verbindungen wie Fenchlorazol(-ethylester), d.h. 1 -(2, 4-Dichlorphenyl)-5-trichlormethyl-(lH)- 1,2, 4-triazol-3 -carbonsäure ethylester (Sl-7), und verwandte Verbindungen wie sie in EP-A-174 562 und EP-A-346 620 beschrieben sind; e) Verbindungen vom Typ der 5-Benzyl- oder 5-Phenyl-2-isoxazolin-3- carbonsäure oder der 5,5- Diphenyl-2-isoxazolin-3-carbonsäure (Sle), vorzugsweise Verbindungen wie methyl l- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-6) and related compounds as described, for example, in EP-A-268554; d) Compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as fenchlorazole (ethyl ester), ie 1 - (2, 4-dichlorophenyl) -5-trichloromethyl- (1H) - 1,2, 4-triazole-3 - carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174 562 and EP-A-346 620; e) Compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ) type, preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3-carbonsäureethylester (Sl-8) oder 5-Phenyl-2-isoxazolin-3- carbonsäureethylester (Sl-9) und verwandte Verbindungen, wie sie in WO-A-91/08202 beschrieben sind, bzw. 5,5-Diphenyl-2-isoxazolin-3-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-3- carbonsäureethylester (Sl-l 1) ("Isoxadifen-ethyl") oder -n-propylester (S1-12) oder der Ethyl 5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylate (Sl-8) or ethyl 5-phenyl-2-isoxazoline-3-carboxylate (Sl-9) and related compounds as described in WO-A- 91/08202 are described, or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (S1-10) or 5,5-diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-L 1) ("Isoxadifen- ethyl ") or -n-propyl ester (S1-12) or the
5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbonsäureethylester (S1-13), wie sie in der 5- (4-Fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-13), as described in the
Patentanmeldung WO-A-95/07897 beschrieben sind. Patent application WO-A-95/07897 are described.
S2) Chinolinderivate der Formel (S2), S2) quinoline derivatives of the formula (S2),
Figure imgf000128_0001
Figure imgf000128_0001
wobei die Symbole und Indizes folgende Bedeutungen haben: RB1 ist Halogen, (Ci-C i)Alkyl, (Ci-C4)Alkoxy, Nitro oder (Ci-C4)Haloalkyl; ne ist eine natürliche Zahl von 0 bis 5, vorzugsweise 0 bis 3; where the symbols and indices have the following meanings: RB 1 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, nitro or (Ci-C4) haloalkyl; ne is a natural number from 0 to 5, preferably 0 to 3;
RB 2 ist ORB 3, SRB 3 oder NRB 3RB 4 oder ein gesättigter oder ungesättigter 3- bis 7-gliedriger Heterocyclus mit mindestens einem N-Atom und bis zu 3 R B 2 is OR B 3 , SR B 3 or NR B 3 R B 4 or a saturated or unsaturated 3 to 7-membered heterocycle with at least one N atom and up to 3
Heteroatomen, vorzugsweise aus der Gruppe O und S, der über das N-Atom mit der Carbonylgruppe in (S2) verbunden ist und unsubstituiert oder durch Reste aus der Gruppe (Ci-C4)Alkyl, (Ci-C4)Alkoxy oder gegebenenfalls substituiertes Phenyl substituiert ist, vorzugsweise ein Rest der Formel ORB 3, NHRB 4 oder N(CH3)2, insbesondere der Formel ORB 3; Heteroatoms, preferably from the group O and S, which is connected via the N atom to the carbonyl group in (S2) and is unsubstituted or by radicals from the group (Ci-C4) alkyl, (Ci-C4) alkoxy or optionally substituted phenyl is substituted, preferably a radical of the formula OR B 3 , NHR B 4 or N (CH3) 2, in particular of the formula OR B 3 ;
RB3 ist Wasserstoff oder ein unsubstituierter oder substituierter aliphatischer Kohlenwasserstoffrest, vorzugsweise mit insgesamt 1 bis 18 C-Atomen; RB 3 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably with a total of 1 to 18 carbon atoms;
RB4 ist Wasserstoff, (Ci-C6)Alkyl, (Ci-C6)Alkoxy oder substituiertes oder unsubstituiertes Phenyl; RB 4 is hydrogen, (Ci-C 6 ) alkyl, (Ci-C 6 ) alkoxy or substituted or unsubstituted phenyl;
TB ist eine (Ci oder C2)-Alkandiylkette, die unsubstituiert oder mit einem oder zwei (Ci- C4)Alkylresten oder mit [(Ci-C3)-Alkoxy]-carbonyl substituiert ist; vorzugsweise: a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise T B is a (Ci or C2) alkanediyl chain which is unsubstituted or substituted with one or two (Ci-C4) alkyl radicals or with [(Ci-C3) alkoxy] carbonyl; preferably: a) compounds of the 8-quinolineoxyacetic acid (S2 a ) type, preferably
(5-Chlor-8-chinolinoxy)essigsäure-(l-methylhexyl)ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1),
(5-Chlor-8-chinolinoxy)essigsäure-(l,3-dimethyl-but-l-yl)ester (S2-2), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-l-yl) ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyloxy-butylester (S2-3), (5-chloro-8-quinolinoxy) 4-allyloxy-butyl acetate (S2-3),
(5-Chlor-8-chinolinoxy)essigsäure-l-allyloxy-prop-2-ylester (S2-4), (5-chloro-8-quinolinoxy) acetic acid l-allyloxy prop-2-yl ester (S2-4),
(5-Chlor-8-chinolinoxy)essigsäureethylester (S2-5), (5-chloro-8-quinolinoxy) ethyl acetate (S2-5),
(5-Chlor-8-chinolinoxy)essigsäuremethylester (S2-6),  (5-chloro-8-quinolinoxy) methyl acetate (S2-6),
(5-Chlor-8-chinolinoxy)essigsäureallylester (S2-7),  (5-chloro-8-quinolinoxy) allyl acetate (S2-7),
(5-Chlor-8-chinohnoxy)essigsäure-2-(2-propyhden-iminoxy)-l-ethylester (S2-8), (5-Chlor-8- chinolinoxy)essigsäure-2-oxo-prop-l-ylester (S2-9) und verwandte Verbindungen, wie sie in  (5-Chloro-8-quinohnoxy) acetic acid 2- (2-propyhden iminoxy) -l-ethyl ester (S2-8), (5-chloro-8-quinolinoxy) acetic acid-2-oxo-prop-l-yl ester (S2-9) and related compounds as described 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; b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise EP-A-86 750, EP-A-94 349 and EP-A-191 736 or EP-A-0 492 366 and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example the lithium, sodium, potassium, calcium, magnesium, aluminum, iron, ammonium, quaternary ammonium, sulfonium or phosphonium salts as described in WO-A-2002/34048 ; b) Compounds of the type of (5-chloro-8-quinolinoxy) malonic acid (S2 b ), preferably
Verbindungen wie (5-Chlor-8-chinolinoxy)malonsäurediethylester, Compounds such as (5-chloro-8-quinolinoxy) diethyl malonate,
(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. S3) Verbindungen der Formel (S3) (5-chloro-8-quinolinoxy) malonic acid diallyl ester, (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0 582 198. S3) compounds of the formula (S3)
Figure imgf000130_0001
wobei die Symbole und Indizes folgende Bedeutungen haben:
Figure imgf000130_0001
where the symbols and indices have the following meanings:
Rc1 ist (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (C2-C4)Alkenyl, (C2-C4)Haloalkenyl, (C3-C7)Cycloalkyl, vorzugsweise Dichlormethyl; Rc 1 is (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 3 -C 7 ) cycloalkyl, preferably dichloromethyl;
Rc2, Rc3 sind gleich oder verschieden Wasserstoff, (Ci-C4)Alkyl, (C2-C4)Alkenyl, (C2-C4)Alkinyl, (Ci- C4)Haloalkyl, (C2-C4)Haloalkenyl, (Ci-C4)Alkylcarbamoyl-(Ci-C4)alkyl, (C2-C4)Alkenylcarbamoyl- (Ci-C4)alkyl, (Ci-C4)Alkoxy-(Ci-C4)alkyl, Dioxolanyl-(Ci-C4)alkyl, Thiazolyl, Furyl, Furylalkyl, Thienyl, Piperidyl, substituiertes oder unsubstituiertes Phenyl, oder Rc2 und Rc3 bilden zusammen einen substituierten oder unsubstituierten heterocyclischen Ring, vorzugsweise einen Oxazolidin-, Rc 2 , Rc 3 are the same or different hydrogen, (Ci-C 4 ) alkyl, (C2-C 4 ) alkenyl, (C2-C 4 ) alkynyl, (Ci-C 4 ) haloalkyl, (C2-C 4 ) haloalkenyl , (Ci-C 4 ) alkylcarbamoyl- (Ci-C 4 ) alkyl, (C2-C 4 ) alkenylcarbamoyl- (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, dioxolanyl - (Ci-C 4 ) alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl, or Rc 2 and Rc 3 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine,
Thiazolidin-, Piperidin-, Morpholin-, Hexahydropyrimidin- oder Benzoxazinring; vorzugsweise: Thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; preferably:
Wirkstoffe vom Typ der Dichloracetamide, die häufig als Vorauflaufsafener (bodenwirksame Safener) angewendet werden, wie z. B. Active substances of the dichloroacetamide type, which are often used as pre-emergence safeners (soil-acting safeners), such as. B.
"Dichlormid" (N,N-Diallyl-2,2-dichloracetamid) (S3-1),  "Dichlormid" (N, N-diallyl-2,2-dichloroacetamide) (S3-1),
"R-29148" (3-Dichloracetyl-2,2,5-trimethyl-l,3-oxazolidin) der Firma Stauffer (S3-2),  "R-29148" (3-dichloroacetyl-2,2,5-trimethyl-1,3-oxazolidine) from Stauffer (S3-2),
"R-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazolidin) der Firma Stauffer (S3-3),  "R-28725" (3-dichloroacetyl-2,2, -dimethyl-1,3-oxazolidine) from Stauffer (S3-3),
"Benoxacor" (4-Dichloracetyl-3,4-dihydro-3-methyl-2H-l,4-benzoxazin) (S3-4),  "Benoxacor" (4-dichloroacetyl-3,4-dihydro-3-methyl-2H-l, 4-benzoxazine) (S3-4),
"PPG-1292" (N-Allyl-N-[(l,3-dioxolan-2-yl)-methyl]-dichloracetamid) der Firma PPG Industries (S3-5),  "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from 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-l-oxa-3-aza-spiro[4,5]decan) der Firma Nitrokemia bzw. Monsanto (S3-7),  "DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide) from Sagro-Chem (S3-6), "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa -3-aza-spiro [4,5] decan) from Nitrokemia or Monsanto (S3-7),
"TI-35" (l-Dichloracetyl-azepan) der Firma TRI-Chemical RT (S3-8),  "TI-35" (l-dichloroacetyl-azepan) from TRI-Chemical RT (S3-8),
"Diclonon" (Dicyclonon) oder "BAS145138" oder "LAB145138" (S3-9)  "Diclonon" (dicyclonone) or "BAS145138" or "LAB145138" (S3-9)
((RS)-l-Dichloracetyl-3,3,8a-trimethylperhydropyrrolo[l,2-a]pyrimidin-6-on) der Firma BASF, "Furilazol" oder "MON 13900" ((RS)-3-Dichloracetyl-5-(2-furyl)-2,2-dimethyloxazolidin) (S3-10); sowie dessen (R)-Isomer (S3-11). S4) N-Acylsulfonamide der Formel (S4) und ihre Salze, ((RS) -l-dichloroacetyl-3,3,8a-trimethylperhydropyrrolo [1,2-a] pyrimidin-6-one) from BASF, "Furilazole" or "MON 13900" ((RS) -3-dichloroacetyl- 5- (2-furyl) -2,2-dimethyloxazolidine) (S3-10); and its (R) -isomer (S3-11). S4) N-acylsulfonamides of the formula (S4) and their salts,
Figure imgf000131_0001
worin die Symbole und Indizes folgende Bedeutungen haben: AD ist S02-NRD 3-C0 oder C0-NRD 3-S02
Figure imgf000131_0001
where the symbols and indices have the following meanings: A D is S0 2 -NR D 3 -C0 or C0-NR D 3 -S0 2
XD ist CH oder N; X D is CH or N;
RD1 ist CO-NRD 5RD 6 oderNHCO-RD 7; RD 1 is CO-NR D 5 R D 6 or NHCO-R D 7 ;
RD 2 ist Halogen, (Ci-C4)Haloalkyl, (Ci-C4)Haloalkoxy, Nitro, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, (Ci- C4)Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl; RD 3 ist Wasserstoff, (Ci-C4)Alkyl, (C2-C4)Alkenyl oder (C2-C4)Alkinyl; R D 2 is halogen, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) alkylsulfonyl, (Ci -C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl; R D 3 is hydrogen, (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl or (C 2 -C 4 ) alkynyl;
RD 4 ist Halogen, Nitro, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Haloalkoxy, (C3-C6)Cycloalkyl, Phenyl, (Ci-C4)Alkoxy, Cyano, (Ci-C4)Alkylthio, (Ci-C4)Alkylsulfinyl, (Ci-C4)Alkylsulfonyl, (Ci- C4)Alkoxycarbonyl oder (Ci-C4)Alkylcarbonyl; R D 4 is halogen, nitro, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) haloalkoxy, (C 3 -C 6 ) cycloalkyl, phenyl, (Ci-C 4 ) alkoxy , Cyano, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylsulfinyl, (Ci-C 4 ) alkylsulfonyl, (Ci-C 4 ) alkoxycarbonyl or (Ci-C 4 ) alkylcarbonyl;
RD 5 ist Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5- C6)Cycloalkenyl, Phenyl oder 3- bis 6-gliedriges Heterocyclyl enthaltend VD Heteroatome aus der Gruppe Stickstoff, Sauerstoff und Schwefel, wobei die sieben letztgenannten Reste durch VD R D 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl, Phenyl or 3- to 6-membered heterocyclyl containing V D heteroatoms from the group consisting of nitrogen, oxygen and sulfur, the last seven radicals being represented by V D
Substituenten aus der Gruppe Halogen, (Ci-C6)Alkoxy, (Ci-C6)Haloalkoxy, (Ci-C2)Alkylsulfmyl, (Ci- C2)Alkylsulfonyl, (C3-C6)Cycloalkyl, (Ci-C4)Alkoxycarbonyl, (Ci-C4)Alkylcarbonyl und Phenyl und im Falle cyclischer Reste auch (C1-C4) Alkyl und (Ci-C4)Haloalkyl substituiert sind; RD 6 ist Wasserstoff, (Ci-C6)Alkyl, (C2-C' 6)Alkcnyl oder (C2-C6)Alkinyl, wobei die drei letztgenannten Reste durch VD Reste aus der Gruppe Halogen, Hydroxy, (Ci-C4)Alkyl, (Ci-C4)Alkoxy und (Ci-C4)Alkylthio substituiert sind, oder Substituents from the group halogen, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkoxy, (Ci-C 2 ) alkylsulfmyl, (Ci-C 2 ) alkylsulfonyl, (C 3 -C 6 ) cycloalkyl, (Ci C 4 ) alkoxycarbonyl, (Ci-C 4 ) alkylcarbonyl and phenyl and in the case of cyclic radicals also (C 1 -C 4 ) alkyl and (Ci-C 4 ) haloalkyl are substituted; R D 6 is hydrogen, (Ci-C 6 ) alkyl, (C 2 -C ' 6 ) alkynyl or (C 2 -C 6 ) alkynyl, the latter three radicals being substituted by V D radicals from the group halogen, hydroxy, ( Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy and (Ci-C 4 ) alkylthio are substituted, or
RD 5 und RD 6 gemeinsam mit dem dem sie tragenden Stickstoffatom einen Pyrrolidinyl- oder Piperidinyl-Rest bilden; RD 7 ist Wasserstoff, (Ci-C4)Alkylamino, Di-(Ci-C4)alkylamino, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci- C6)Haloalkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch (Ci-C4)Alkyl und R D 5 and R D 6 together with the nitrogen atom carrying them form a pyrrolidinyl or piperidinyl radical; R D 7 is hydrogen, (Ci-C4) alkylamino, di- (Ci-C4) alkylamino, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen , (Ci-C4) alkoxy, (Ci- C 6) haloalkoxy and (Ci-C4) alkylthio and in case of cyclic radicals, also (Ci-C4) alkyl and
(Ci-C4)Haloalkyl substituiert sind; nD ist 0, 1 oder 2; mD ist 1 oder 2; (Ci-C4) haloalkyl are substituted; n D is 0, 1 or 2; m D is 1 or 2;
VD ist 0, 1, 2 oder 3; davon bevorzugt sind Verbindungen vom Typ der N-Acylsulfonamide, z.B. der nachfolgenden Formel (S4a), die z. B. bekannt sind aus WO-A-97/45016 V D is 0, 1, 2 or 3; Of these, preference is given to compounds of the N-acylsulfonamide type, for example the following formula (S4 a ), which, for. B. are known from WO-A-97/45016
Figure imgf000132_0001
worin
Figure imgf000132_0001
wherein
RD 7 (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VD Substituenten aus der Gruppe Halogen, (Ci-C4)Alkoxy, (Ci-C6)Haloalkoxy und (Ci-C4)Alkylthio und im Falle cyclischer Reste auch (Ci-C4)Alkyl und (Ci-C4)Haloalkyl substituiert sind; Rd 4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; mD 1 oder 2; R D 7 (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the latter 2 radicals being substituted by V D substituents from the group halogen, (Ci-C4) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci C4) alkylthio and in the case of cyclic radicals also (Ci-C4) alkyl and (Ci-C4) haloalkyl are substituted; R d 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2;
VD ist 0, 1, 2 oder 3 bedeutet; sowie VD is 0, 1, 2 or 3; such as
Acylsulfamoylbenzoesäureamide, z.B. der nachfolgenden Formel (S4b), die z.B. bekannt sind aus WO- A-99/16744, Acylsulfamoylbenzoic acid amides, for example the following formula (S4 b ), which are known, for example, from WO-A-99/16744,
Figure imgf000132_0002
z.B. solche worin RD5 = Cyclopropyl und (RD4) = 2-OMe ist("Cyprosulfamide", S4-1),
Figure imgf000132_0002
eg those in which RD 5 = cyclopropyl and (RD 4 ) = 2-OMe is ("Cyprosulfamide", S4-1),
RD5 = Cyclopropyl und (RD4) = 5-Cl-2-OMe ist (S4-2), RD 5 = cyclopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-2),
RD5 = Ethyl und (RD4) = 2-OMe ist(S4-3), RD 5 = ethyl and (RD 4 ) = 2-OMe is (S4-3),
RD5 = Isopropyl und (RD4) = 5-Cl-2-OMe ist (S4-4) und RD5 = Isopropyl und (RD4) = 2-OMe ist (S4-5). sowie RD 5 = isopropyl and (RD 4 ) = 5-Cl-2-OMe is (S4-4) and RD 5 = isopropyl and (RD 4 ) = 2-OMe is (S4-5). such as
Verbindungen vom Typ der N-Acylsulfamoylphenylhamstoffe der Formel (S4C), die z.B. bekannt sind aus der EP-A-365484, Compounds of the N-acylsulfamoylphenyl urea type of the formula (S4 C ), which are known, for example, from EP-A-365484,
Figure imgf000133_0001
worin
Figure imgf000133_0001
wherein
RD8 und RD9 unabhängig voneinander Wasserstoff, (Ci-Cg)Alkyl, (C3-Cg)Cycloalkyl, (C3-C6)Alkenyl, (C3-C6)Alkinyl, RD 8 and RD 9 independently of one another are hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-C6) alkenyl, (C 3 -C 6 ) alkynyl,
RD4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3 mD 1 oder 2 bedeutet; beispielsweise l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff, RD 4 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3 m D 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylhamstoff, l- [4- (N-2-Methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylhamstoff, sowie N-Phenylsulfonylterephthalamide der Formel (S4d), die z.B. bekannt sind aus CN 101838227, l- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methylhamstoff, and N-Phenylsulfonylterephthalamide of the formula (S4 d), which are for example known from CN 101838227,
Figure imgf000133_0002
z.B. solche worin
Figure imgf000133_0002
eg those in which
RD 4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; niD 1 oder 2; R D 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; ni D 1 or 2;
RD 5 Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5- C6)Cycloalkenyl bedeutet. R D 5 is hydrogen, (Ci-C 6 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 2 -C 6 ) alkenyl, (C 2 -C 6 ) alkynyl, (C 5 - C 6 ) cycloalkenyl.
55) Wirkstoffe aus der Klasse der Hydroxyaromaten und der aromatisch-aliphatischen 55) Active ingredients from the class of the hydroxyaromatics and the aromatic-aliphatic
Carbonsäurederivate (S5), z.B. Carboxylic acid derivatives (S5), e.g.
3,4,5-Triacetoxybenzoesäureethylester, 3,5-Dimethoxy-4-hydroxybenzoesäure, 3,5- Dihydroxybenzoesäure, 4-Hydroxysalicylsäure, 4-Fluorsalicyclsäure, 2-Hydroxyzimtsäure, 2,4- Dichlorzimtsäure, wie sie in der WO-A-2004/084631, WO-A-2005/015994, WO-A-2005/016001 beschrieben sind.  3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 3,5-dihydroxybenzoic acid, 4-hydroxysalicylic acid, 4-fluorosalicyclic acid, 2-hydroxycinnamic acid, 2,4-dichlorocinnamic acid, as described in WO-A- 2004/084631, WO-A-2005/015994, WO-A-2005/016001.
56) Wirkstoffe aus der Klasse der l,2-Dihydrochinoxalin-2-one (S6), z.B. 56) Active substances from the class of 1,2-dihydroquinoxalin-2-one (S6), e.g.
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)-l,2-dihydro-chinoxalin-2-on, wie sie in der WO-A- 2005/112630 beschrieben sind.  1-Methyl-3 - (2-thienyl) - 1, 2-dihydroquinoxalin-2-one, 1-methyl-3 - (2-thienyl) - 1, 2-dihydroquinoxalin-2-thione, 1 - (2-aminoethyl ) -3- (2-thienyl) -1, 2-dihydro-quinoxalin-2-one hydrochloride, 1 - (2- methylsulfonylaminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin-2- on, as described in WO-A-2005/112630.
57) Verbindungen der Formel (S7),wie sie in der WO-A-1998/38856 beschrieben sind 57) Compounds of the formula (S7), as described in WO-A-1998/38856
Figure imgf000134_0001
Figure imgf000134_0001
worin die Symbole und Indizes folgende Bedeutungen haben: RE 1, RE 2 sind unabhängig voneinander Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkyl,where the symbols and indices have the following meanings: R E 1 , R E 2 are independently halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkyl,
(Ci-C4)Alkylamino, Di-(Ci-C4)Alkylamino, Nitro; (Ci-C 4 ) alkylamino, di- (Ci-C 4 ) alkylamino, nitro;
AE ist COORE 3 oder COSRE 4 RE3, RE4 sind unabhängig voneinander Wasserstoff, (Ci-C4)Alkyl, (CF-GOAlkcnyl,A E is COOR E 3 or COSR E 4 RE 3 , RE 4 are independently hydrogen, (Ci-C4) alkyl, (CF-GOalknyl,
(C2-C4)Alkinyl, Cyanoalkyl, (Ci-C4)Haloalkyl, Phenyl, Nitrophenyl, Benzyl, Halobenzyl, Pyridinylalkyl und Alkylammonium, he1 ist 0 oder 1 he2, he3 sind unabhängig voneinander 0, 1 oder 2, vorzugsweise: (C2-C4) alkynyl, cyanoalkyl, (Ci-C4) haloalkyl, phenyl, nitrophenyl, benzyl, halobenzyl, pyridinylalkyl and alkylammonium, he 1 is 0 or 1 he 2 , he 3 are independently 0, 1 or 2, preferably:
Diphenylmethoxyessigsäure,  diphenylmethoxy,
Diphenylmethoxyessigsäureethylester,  Diphenylmethoxyessigsäureethylester,
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1). S8) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind  Diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1). S8) Compounds of the formula (S8), as described in WO-A-98/27049
Figure imgf000135_0001
wonn
Figure imgf000135_0001
Wonn
XF CH oder N, nF für den Fall, dass XF=N ist, eine ganze Zahl von 0 bis 4 und für den Fall, dass XF=CH ist, eine ganze Zahl von 0 bis 5 , XF CH or N, n F is an integer from 0 to 4 if X F = N and an integer from 0 to 5 if X F = CH,
RF1 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, Nitro, (Ci- C4)Alkylthio, (Ci-C4)-Alkylsulfonyl, (Ci-C4)Alkoxycarbonyl, ggf. substituiertes. Phenyl, ggf. RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, nitro, (Ci-C4) alkylthio, (Ci-C4) alkylsulfonyl, ( Ci-C4) alkoxycarbonyl, optionally substituted. Phenyl, optionally
substituiertes Phenoxy, substituted phenoxy,
RF2 Wasserstoff oder (Ci-C4)Alkyl RF3 Wasserstoff, (Ci-CsjAlkyl, (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; bedeuten, oder deren Salze, vorzugsweise Verbindungen worin XF CH, nF eine ganze Zahl von 0 bis 2 , RF 2 hydrogen or (Ci-C4) alkyl RF 3 hydrogen, (Ci-CsjAlkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals unsubstituted or by one or more , preferably up to three identical or different radicals from the group consisting of halogen and alkoxy, or their salts, preferably compounds in which XF CH, n F is an integer from 0 to 2,
RF1 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, RF 1 halogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy,
RF2 Wasserstoff oder (Ci-C4)Alkyl, RF3 Wasserstoff, (Ci-Cg)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, bedeuten, RF 2 hydrogen or (Ci-C4) alkyl, RF 3 hydrogen, (Ci-Cg) alkyl, (C2-C4) alkenyl, (C2-C4) alkynyl, or aryl, each of the aforementioned C-containing radicals being unsubstituted or by one or more, preferably up to three identical or different radicals from the group consisting of halogen and alkoxy substituted,
oder deren Salze. S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. or their salts. S9) active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
l,2-Dihydro-4-hydroxy-l-ethyl-3-(5-tetrazolylcarbonyl)-2-chinolon (CAS-Reg.Nr. 219479-18-2), 1,2- Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr. 95855-00-8), wie sie in der WO-A- 1999/000020 beschrieben sind. 1,2-Dihydro-4-hydroxy-l-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg. No. 219479-18-2), 1,2-dihydro-4-hydroxy-l -methyl-3- (5-tetrazolyl-carbonyl) -2-quinolone (CAS Reg. No. 95855-00-8), as described in WO-A-1999/000020.
S 10) Verbindungen der Formeln (S 10a) oder (S 10b) wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind S 10) compounds of the formulas (S 10 a ) or (S 10 b ) as described in WO-A-2007/023719 and WO-A-2007/023764
Figure imgf000136_0001
wonn
Figure imgf000136_0001
Wonn
RG1 Halogen, (Ci-C4)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 RG 1 halogen, (Ci-C4) alkyl, methoxy, nitro, cyano, CF3, OCF3
YG, ZG unabhängig voneinander O oder S, no eine ganze Zahl von 0 bis 4, Y G , Z G independently of one another O or S, no an integer from 0 to 4,
RG2 (Ci-CiejAlkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RG3 Wasserstoff oder (C 1 -Cr,)Alkyl bedeutet. Sl 1) Wirkstoffe vom Typ der Oxyimino- Verbindungen (Sl 1), die als Saatbeizmittel bekannt sind, wie z. B. RG 2 is (Ci-Ciejalkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; benzyl, halobenzyl, RG 3 is hydrogen or (C 1 -Cr,) alkyl. Sl 1) Active substances of the oxyimino compound type (Sl 1), which are known as seed dressings, such as. B.
"Oxabetrinil" ((Z)-l,3-Dioxolan-2-ylmethoxyimino(phenyl)acetonitril) (Sl l-l), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, "Fluxofenim" (l-(4-Chlorphenyl)-2,2,2-trifluor-l-ethanon-0-(l,3-dioxolan-2-ylmethyl)-oxim) (Sl 1-2), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist, und  "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl ll), which is known as a seed dressing safener for millet against damage to metolachlor, "fluxofenim" (l- (4- Chlorphenyl) -2,2,2-trifluoro-l-ethanone-0- (l, 3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), known as a seed dressing safener for millet against damage from metolachlor is and
"Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (Sl l-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. "Cyometrinil" or "CGA-43089" ((Z) -cyanomethoxyimino (phenyl) acetonitrile) (Sl l-3), which is known as a seed dressing safener for millet against damage to metolachlor.
512) Wirkstoffe aus der Klasse der lsothiochromanone (S12), wie z.B. Methyl- [(3 -oxo-lH-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte512) active substances from the class of the isothiochromanones (S12), such as Methyl- [(3-oxo-1H-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS Reg. No. 205121-04-6) (S12-1) and related
Verbindungen aus WO-A-1998/13361. Compounds from WO-A-1998/13361.
513) Eine oder mehrere Verbindungen aus Gruppe (S13): 513) One or more compounds from group (S13):
"Naphthalic anhydrid" (l,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 Pretilachlor in gesätem Reis bekannt ist, "Naphthalic anhydride" (1,8-naphthalenedicarboxylic acid anhydride) (S13-1), which is known as a seed dressing safener for maize against damage by thiocarbamate herbicides, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2) known as a safener for pretilachlor in sown rice,
"Flurazole" (Benzyl-2-chlor-4-trifluormethyl-l,3-thiazol-5-carboxylat) (S13-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Alachlor und Metolachlor bekannt ist, "Flurazole" (benzyl-2-chloro-4-trifluoromethyl-l, 3-thiazole-5-carboxylate) (S13-3), which is known as a seed dressing safener for millet against damage to alachlor and metolachlor,
"CL 304415" (CAS-Reg.Nr. 31541-57-8) "CL 304415" (CAS reg.no.31541-57-8)
(4-Carboxy-3,4-dihydro-2H-l-benzopyran-4-essigsäure) (S13-4) der Firma American Cyanamid, das als Safener für Mais gegen Schäden von lmidazolinonen bekannt ist, (4-carboxy-3,4-dihydro-2H-l-benzopyran-4-acetic acid) (S13-4) from American Cyanamid, which is known as a safener for maize against damage to imidazolinones,
"MG 191" (CAS-Reg.Nr. 96420-72-3) (2-Dichlormethyl-2-methyl-l,3-dioxolan) (S13-5) der Firma Nitrokemia, das als Safener für Mais bekannt ist, "MG 191" (CAS Reg. No. 96420-72-3) (2-dichloromethyl-2-methyl-1,3-dioxolane) (S13-5) from Nitrokemia, which is known as a safener for corn,
"MG 838" (CAS-Reg.Nr. 133993-74-5) "MG 838" (CAS Reg. No. 133993-74-5)
(2-propenyl l-oxa-4-azaspiro[4.5]decan-4-carbodithioat) (S13-6) der Firma Nitrokemia, (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia,
"Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7), "Disulfoton" (O, O-Diethyl S-2-ethylthioethyl phosphorodithioate) (S13-7),
Dietholate" (O,O-Diethyl-O-phenylphosphorothioat) (S13-8), Dietholate "(O, O-Diethyl-O-phenylphosphorothioat) (S13-8),
'Mephenate" (4-Chlorphenyl-methylcarbamat) (S13-9). S14) Wirkstoffe, die neben einer herbiziden Wirkung gegen Schadpflanzen auch Safenerwirkung an Kulturpflanzen wie Reis aufweisen, wie z. B. 'Mephenate' (4-chlorophenyl methyl carbamate) (S13-9). S14) Active ingredients which, in addition to a herbicidal action against harmful plants, also have a safener action on crop plants such as rice, such as, for. B.
"Dimepiperate" oder "MY 93" (S- 1 -Methyl- 1 -phcnylcthyl-pipcridin- 1 -carbothioat), das als Safener für Reis gegen Schäden des Herbizids Molinate bekannt ist, "Daimuron" oder "SK 23" (l-(l-Methyl-l-phenylethyl)-3-p-tolyl-hamstoff), das als Safener für Reis gegen Schäden des Herbizids lmazosulfüron bekannt ist,  "Dimepiperate" or "MY 93" (S-1-methyl-1-phcnylcthyl-pipcridin-1-carbothioate), which is known as a safener for rice against damage from the herbicide Molinate, "Daimuron" or "SK 23" (1- (l-methyl-l-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage to the herbicide lmazosulfüron,
"Cumyluron" = "JC 940" (3-(2-Chlorphenylmethyl)-l-(l-methyl-l-phenyl-ethyl)hamstoff, siehe JP-A- 60087254), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Cumyluron" = "JC 940" (3- (2-chlorophenylmethyl) -l- (l-methyl-l-phenyl-ethyl) urea, see JP-A-60087254), which is known as a safener for rice against damage to some herbicides is
"Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenone" or "NK 049" (3,3'-dimethyl-4-methoxy-benzophenone), which is known as a safener for rice against damage by some herbicides,
"CSB" (l-Brom-4-(chlormethylsulfonyl)benzol) von Kumiai, (CAS-Reg.Nr. 54091-06-4), das als Safener gegen Schäden einiger Herbizide in Reis bekannt ist. "COD" (l-bromo-4- (chloromethylsulfonyl) benzene) from Kumiai, (CAS Reg. No. 54091-06-4), which is known as a safener against damage to some herbicides in rice.
S15) Verbindungen der Formel (S15) oder deren Tautomere S15) compounds of the formula (S15) or their tautomers
Figure imgf000138_0001
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, worin RH1 einen (Ci-C6)Haloalkylrest bedeutet und
Figure imgf000138_0001
as described in WO-A-2008/131861 and WO-A-2008/131860, in which RH 1 denotes a (Ci-C 6 ) haloalkyl radical and
RH2 Wasserstoff oder Halogen bedeutet und RH 2 is hydrogen or halogen and
RH 3, RH 4 unabhängig voneinander Wasserstoff, (Ci-Ci6)Alkyl, (C2-Ci6)Alkenyl oder R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
(C2-Ci6)Alkinyl, wobei jeder der letztgenannten 3 Reste unsubstituiert oder durch einen oder mehrere Reste aus der Gruppe Halogen, Hydroxy, Cyano, (Ci-C i)Alkoxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (C 2 -Ci 6 ) alkynyl, each of the latter 3 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C i) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4 ) alkylthio,
(Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, [(Ci-C4)Alkoxy]-carbonyl, [(Ci-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, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl, (Ci-C4)Alkoxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci-C4)alkyl]-amino, [(Ci-c4)Alkoxy]-carbonyl, (Ci-C4) alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C4) alkoxy] carbonyl, [(Ci-C4) haloalkoxy] carbonyl, (C3-C6) cycloalkyl, which is unsubstituted or is substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted is substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl fused to one side of the ring with a 4-6 membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl which is condensed on one side of the ring with a 4 to 6-membered saturated or unsaturated carbocyclic ring, each of the latter 4 residues being unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C4) alkyl , (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy, (Ci-C4) alkylthio, (Ci-C4) alkylamino, di [(Ci-C4) alkyl] amino, [( Ci-C4) alkoxy] -carbonyl,
[(Ci-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, bedeutet oder [(Ci-C4) Haloalkoxy] carbonyl, (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted, and heterocyclyl which is unsubstituted or substituted, substituted or
RH3 (Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und RH4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder RH 3 is (Ci-C4) alkoxy, (C2-C4) alkenyloxy, (C2-C6) alkynyloxy or (C2-C4) haloalkoxy and RH 4 is hydrogen or (Ci-C4) alkyl or
RH3 und RH4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen RH 3 and RH 4 together with the directly bound N atom have a four- to eight-membered structure
heterocyclischen Ring, der neben dem N-Atom auch weitere Heteroringatome, 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, (Ci-C4)Haloalkoxy und (Ci-C4)Alkylthio substituiert ist, bedeutet. heterocyclic ring which, in addition to the N atom, can also contain further hetero ring atoms, preferably up to two further hetero ring atoms from the group N, O and S, and which is unsubstituted or by one or more radicals from the group halogen, cyano, nitro, (Ci C4) alkyl, (Ci-C4) haloalkyl, (Ci-C4) alkoxy, (Ci-C4) haloalkoxy and (Ci-C4) alkylthio is substituted.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z.B. S16) Active substances which are primarily used as herbicides, but also have safener action on crop plants, e.g.
(2,4-Dichlorphenoxy)essigsäure (2,4-D), (2,4-dichlorophenoxy) acetic acid (2,4-D),
(4-Chlorphenoxy)essigsäure,  (4-chlorophenoxy) acetic acid,
(R,S)-2-(4-Chlor-o-tolyloxy)propionsäure (Mecoprop),  (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop),
4-(2,4-Dichlorphenoxy)buttersäure (2,4-DB),  4- (2,4-dichlorophenoxy) butyric acid (2,4-DB),
(4-Chlor-o-tolyloxy)essigsäure (MCPA),  (4-chloro-o-tolyloxy) acetic acid (MCPA),
4-(4-Chlor-o-tolyloxy)buttersäure,  4- (4-chloro-o-tolyloxy) butyric acid,
4-(4-Chlorphenoxy)buttersäure,  4- (4-chlorophenoxy) butyric acid,
3,6-Dichlor-2-methoxybenzoesäure (Dicamba),  3,6-dichloro-2-methoxybenzoic acid (dicamba),
l-(Ethoxycarbonyl)ethyl-3,6-dichlor-2-methoxybenzoat (Lactidichlor-ethyl). 1- (Ethoxycarbonyl) ethyl 3,6-dichloro-2-methoxybenzoate (lactidichloro-ethyl).
Besonders bevorzugte Safener in Kombination mit den erfindungsgemäßen Verbindungend der allgemeinen Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (1.1) bis (1.137) und/oder deren Salze sind: Mefenpyr-diethyl, Cyprosulfamid, Isoxadifen-ethyl, Cloquintocet- mexyl, Dichlormid und Metcamifen. Particularly preferred safeners in combination with the compounds according to the invention of the general formula (I) and / or their salts, in particular with the compounds of the formulas (1.1) to (1,137) and / or their salts are: mefenpyr-diethyl, cyprosulfamide, isoxadifen-ethyl, cloquintocet-mexyl, dichlormid and metcamifene.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obgleich die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten. Diesbezüglich sind Kombinationen The selective control of harmful plants in crops of useful and ornamental plants is of particular interest. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many crops, phytotoxicity can occur on the crop plants in principle in some crops and especially in the case of mixtures with other herbicides which are less selective. In this regard, combinations are
erfindungsgemäßer Verbindungen der allgemeinen Formel (1) von besonderem lnteresse, welche die Verbindungen der allgemeinen Formel (1) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten. Die Safener, welche in einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide/Pestizide, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide (Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide. Compounds of the general formula (1) according to the invention of particular interest which contain the compounds of the general formula (1) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidotically effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, rapeseed, cotton and soybeans, preferably cereals.
Die Gewichtsverhältnisse von Herbizid(mischung) zu Safener hängt im Allgemeinen von der The weight ratio of herbicide (mixture) to safener generally depends on the
Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren, beispielsweise im Bereich von 200:1 bis 1 :200, vorzugsweise 100:1 bis 1 :100, insbesondere 20:1 bis 1 :20. Die Safener können analog den Verbindungen der allgemeinen Formel (1) oder deren Mischungen mit weiteren Herbiziden/Pestiziden formuliert werden und als Application rate of herbicide and the effectiveness of the respective safener and can vary within wide limits, for example in the range from 200: 1 to 1: 200, preferably 100: 1 to 1: 100, in particular 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of the general formula (1) or their mixtures with further herbicides / pesticides and as
Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden. Ready formulation or tank mix with the herbicides are provided and applied.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvem, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. For use, the formulations present in the commercial form are optionally diluted in the customary manner, for example for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Dust-like preparations, soil or
Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. Scatter granules and sprayable solutions are usually no longer diluted with other inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feuchtigkeit, der Art des verwendeten Herbizids, u.a. variiert die erforderliche Aufwandmenge der Verbindungen der allgemeinen Formel (1) und deren Salze. Sie kann innerhalb weiter Grenzen schwanken, z.B. zwischen 0,001 und 10,0 kg/ha oder mehr With the external conditions such as temperature, humidity, the type of herbicide used, etc. the required application rate of the compounds of general formula (1) and their salts varies. It can fluctuate within wide limits, e.g. between 0.001 and 10.0 kg / ha or more
Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 bis 5 kg/ha, weiter bevorzugt im Bereich von 0,01 bis 1,5 kg/ha, insbesondere bevorzugt im Bereich von 0,05 bis 1 kg/ha g/ha. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. Active substance, but preferably it is between 0.005 to 5 kg / ha, more preferably in the range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha g / ha. This applies to both pre-emergence and post-emergence applications.
Trägerstoff bedeutet eine natürliche oder synthetische, organische oder anorganische Substanz, mit welchen die Wirkstoffe zur besseren Anwendbarkeit, v.a. zum Aufbringen auf Pflanzen oder Pflanzenteile oder Saatgut, gemischt oder verbunden sind. Der Trägerstoff, welcher fest oder flüssig sein kann, ist im Allgemeinen inert und sollte in der Landwirtschaft verwendbar sein. Carrier means a natural or synthetic, organic or inorganic substance, with which the active ingredients for better applicability, especially for application to plants or Parts of plants or seeds, mixed or combined. The carrier, which can be solid or liquid, is generally inert and should be useful in agriculture.
Als feste oder flüssige Trägerstoffe kommen infrage: z.B. Ammoniumsalze und natürliche Gesteins mehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Attapulgit, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und natürliche oder synthetische Silikate, Harze, Wachse, feste Düngemittel, Wasser, Alkohole, besonders Butanol, organische Solventien, Mineral- und Pflanzenöle sowie Derivate hiervon. Mischungen solcher  Solid or liquid carriers are possible: e.g. Ammonium salts and natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and natural or synthetic silicates, resins, waxes, solid fertilizers, water, alcohols, especially butanol , organic solvents, mineral and vegetable oils and derivatives thereof. Mixtures of such
Trägerstoffe können ebenfalls verwendet werden. Als feste Trägerstoffe für Granulate kommen infrage: 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, Kokosnussschalen, Maiskolben und Tabakstängel. Carriers can also be used. Solid carriers for granules are possible: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems.
Als verflüssigte gasförmige Streckmittel oder Trägerstoffe kommen solche Flüssigkeiten infrage, welche bei normaler Temperatur und unter Normaldruck gasförmig sind, z.B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, sowie Butan, Propan, Stickstoff und Kohlendioxid.  Liquids which can be used as liquefied gaseous extenders or carriers are those which are gaseous at normal temperature and under normal pressure, e.g. Aerosol propellants, such as halogenated hydrocarbons, as well as butane, propane, nitrogen and carbon dioxide.
Es können in den Formulierungen Haftmittel wie Carboxymethylcellulose, natürliche und synthetische pulverige, körnige oder latexförmige Polymere verwendet werden, wie Gummiarabikum, Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, can be used in the formulations.
Polyvinylalkohol, Polyvinylacetat, sowie natürliche Phospholipide, wie Kephaline und Lecithine, und synthetische Phospholipide. Weitere Additive können mineralische und vegetabile Öle sein. Polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids. Other additives can be mineral and vegetable oils.
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösungsmittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösungsmittel kommen im Wesentlichen infrage: Aromaten, wie Xylol, Toluol oder Alkylnaphthaline, chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Dichlormethan, aliphatische Kohlenwasser stoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or dichloromethane, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils,
Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone, wie Aceton, Methyl- ethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel wie Dimethyl formamid und Dimethylsulfoxid, sowie Wasser. Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl formamide and dimethyl sulfoxide, and water.
Die erfindungsgemäßen Mittel können zusätzlich weitere Bestandteile enthalten, wie z.B. The agents according to the invention can additionally contain further constituents, e.g.
oberflächenaktive Stoffe. Als oberflächenaktive Stoffe kommen Emulgier- und/oder Schaum erzeugende Mittel, Dispergiermittel oder Benetzungsmittel mit ionischen oder nicht-ionischen surfactants. Suitable surface-active substances are emulsifiers and / or foam-generating agents, dispersants or wetting agents with ionic or nonionic
Eigenschaften oder Mischungen dieser oberflächenaktiven Stoffe infrage. Beispiele hierfür sind Salze von Polyacrylsäure, Salze von Lignosulphonsäure, Salze von Phenolsulphonsäure oder Properties or mixtures of these surfactants in question. Examples of these are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or
Naphthalinsulphonsäure, Polykondensate von Ethylenoxid mit Fettalkoholen oder mit Fettsäuren oder mit Fettaminen, substituierten Phenolen (vorzugsweise Alkylphenole oder Arylphenole), Salze von Sulphobemsteinsäureestem, Taurinderivate (vorzugsweise Alkyltaurate), Phosphorsäureester von polyethoxylierten Alkoholen oder Phenole, Fettsäureester von Polyolen, und Derivate der Verbindungen enthaltend Sulphate, Sulphonate und Phosphate, z.B. Alkylarylpolyglycolether, Alkylsulfonate, Alkyl sulfate, Arylsulfonate, Eiweißhydrolysate, Lignin- Sulfitablaugen und Methylcellulose. Die Anwesenheit einer oberflächenaktiven Substanz ist notwendig, wenn einer der Wirkstoff und/oder einer der inerten Trägerstoffe nicht in Wasser löslich ist und wenn die Anwendung in Wasser erfolgt. Der Anteil an oberflächenaktiven Stoffen liegt zwischen 5 und 40 Gewichtsprozent des erfindungsgemäßen Mittels.Naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurate derivatives), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulfates, sulfonates and phosphates, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolyzates, lignin sulfite waste liquors and methyl cellulose. The presence of a surface-active substance is necessary if one of the active ingredients and / or one of the inert carriers is not soluble in water and if the application takes place in water. The proportion of surface-active substances is between 5 and 40 percent by weight of the agent according to the invention.
Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe, wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
Gegebenenfalls können auch andere zusätzliche Komponenten enthalten sein, z.B. schützende Kolloide, Bindemittel, Klebstoffe, Verdicker, thixotrope Stoffe, Penetrationsförderer, Stabilisatoren, If necessary, other additional components may also be included, e.g. protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration enhancers, stabilizers,
Sequestiermittel, Komplexbildner. Im Allgemeinen können die Wirkstoffe mit jedem festen oder flüssigen Additiv, welches für Formulierungszwecke gewöhnlich verwendet wird, kombiniert werden. Im Allgemeinen enthalten die erfindungsgemäßen Mittel und Formulierungen zwischen 0,05 und 99 Gew.-%, 0,01 und 98 Gew.-%, vorzugsweise zwischen 0,1 und 95 Gew.-%, besonders bevorzugt zwischen 0,5 und 90 % Wirkstoff, ganz besonders bevorzugt zwischen 10 und 70 Gewichtsprozent. Die erfindungsgemäßen Wirkstoffe bzw. Mittel können als solche oder in Abhängigkeit von ihren je weiligen physikalischen und/oder chemischen Eigenschaften in Form ihrer Formulierungen oder den daraus bereiteten Anwendungsformen, wie Aerosole, Kapselsuspensionen, Kaltnebelkonzentrate, Heißnebelkonzentrate, verkapselte Granulate, Feingranulate, fließfähige Konzentrate für die Sequestering agents, complexing agents. In general, the active ingredients can be combined with any solid or liquid additive that is commonly used for formulation purposes. In general, the agents and formulations according to the invention contain between 0.05 and 99% by weight, 0.01 and 98% by weight, preferably between 0.1 and 95% by weight, particularly preferably between 0.5 and 90% Active ingredient, very particularly preferably between 10 and 70 percent by weight. The active compounds or agents according to the invention, as such or depending on their respective physical and / or chemical properties in the form of their formulations or the use forms prepared therefrom, such as aerosols, capsule suspensions, cold mist concentrates, hot mist concentrates, encapsulated granules, fine granules, flowable concentrates for the
Behandlung von Saatgut, gebrauchsfertige Lösungen, verstäubbare Pulver, emulgierbare Konzentrate, Öl-in-Wasser-Emulsionen, Wasser-in-Öl-Emulsionen, Makrogranulate, Mikrogranulate, Öl dispergierbare Pulver, Öl mischbare fließfähige Konzentrate, Öl mischbare Flüssigkeiten, Schäume, Pasten, Pestizid ummanteltes Saatgut, Suspensionskonzentrate, Suspensions-Emulsions-Konzentrate, lösliche Konzentrate, Suspensionen, Spritzpulver, lösliche Pulver, Stäubemittel und Granulate, wasser lösliche Granulate oder Tabletten, wasserlösliche Pulver für Saatgut-behandlung, benetzbare Pulver, Wirkstoff-imprägnierte Natur- und synthetische Stoffe sowie Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut, sowie ULV-Kalt- und Warmnebel-Formulierungen eingesetzt werden. Treatment of seeds, ready-to-use solutions, dustable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, macrogranules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, foams, pastes, Pesticide-coated seeds, suspension concentrates, suspension emulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble granules or tablets, water-soluble powders for seed treatment, wettable powders, active substance-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric materials and in coating compositions for seeds, as well as ULV cold and warm mist formulations.
Die genannten Formulierungen können in an sich bekannter Weise hergestellt werden, z.B. durch Ver mischen der Wirkstoffe mit mindestens einem üblichen Streckmittel, Lösungs- bzw. Verdünnungs mittel, Emulgator, Dispergier- und/oder Binde- oder Fixiermittels, Netzmittel, Wasser-Repellent, gegebenenfalls Sikkative und UV-Stabilisatoren und gegebenenfalls Farbstoffen und Pigmenten, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline sowie weiteren V erarbeitungshilfsmittein. Die erfindungsgemäßen Mittel umfassen nicht nur Formulierungen, welche bereits anwendungsfertig sind und mit einer geeigneten Apparatur auf die Pflanze oder das Saatgut ausgebracht werden können, sondern auch kommerzielle Konzentrate, welche vor Gebrauch mit Wasser verdünnt werden müssen. Die erfindungsgemäßen Wirkstoffe können als solche oder in ihren (handelsüblichen) Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen (bekannten) Wirkstoffen, wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden, Nema- tiziden, Fungiziden, Wachstumsregulatoren, Herbiziden, Düngemitteln, Safener bzw. Semiochemicals vorliegen. The formulations mentioned can be prepared in a manner known per se, for example by mixing the active compounds with at least one conventional extender, solvent or diluent, emulsifier, dispersant and / or binder or fixative, wetting agent, water repellent, if appropriate Drying agents and UV stabilizers and, if appropriate, dyes and pigments, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and other processing aids. The compositions according to the invention include not only formulations which are already ready for use and can be applied to the plant or the seed using suitable apparatus, but also commercial concentrates which must be diluted with water before use. The active compounds according to the invention can be used as such or in their (commercially available) formulations and in the use forms prepared from these formulations in a mixture with other (known) active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides , Fertilizers, safeners or semiochemicals are available.
Die erfindungsgemäße Behandlung der Pflanzen und Pflanzenteile mit den Wirkstoffen bzw. Mitteln erfolgt direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-) Spritzen, (Ver-) Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-) Streuen, Verschäumen, Bestreichen, Verstreichen, Gießen (drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Samen, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen usw. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low- Volume- Verfahren auszubringen oder die Wirkstoffzubereitung oder den Wirkstoff selbst in den Boden zu injizieren. The treatment of the plants and parts of plants according to the invention with the active compounds or agents is carried out directly or by acting on their surroundings, living space or storage space according to the usual treatment methods, e.g. by dipping, (spraying) spraying, (spraying) spraying, sprinkling, evaporating, atomizing, atomizing, (scattering) scattering, foaming, brushing, spreading, watering (drenching), drip irrigation and with propagation material, in particular with seeds by dry pickling, wet pickling, slurry pickling, incrustation, single- or multi-layer coating, etc. It is also possible to apply the active ingredients using the ultra-low-volume process or to inject the active ingredient preparation or the active ingredient into the soil itself.
Wie auch weiter unten beschrieben, ist die Behandlung von transgenem Saatgut mit den erfindungsge mäßen Wirkstoffen bzw. Mitteln von besonderer Bedeutung. Dies betrifft das Saatgut von Pflanzen, die wenigstens ein heterologes Gen enthalten, das die Expression eines Polypeptids oder Proteins mit insektiziden Eigenschaften ermöglicht. Das heterologe Gen in transgenem Saatgut kann z.B. aus Mikroorganismen der Arten Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Bevorzugt stammt dieses heterologe Gen aus Bacillus sp., wobei das Genprodukt eine Wirkung gegen den Maiszünsler (European com borer) und/oder Western Com Rootworm besitzt. Besonders bevorzugt stammt das heterologe Gen aus Bacillus thuringiensis. As also described below, the treatment of transgenic seeds with the active substances or agents according to the invention is of particular importance. This relates to the seeds of plants which contain at least one heterologous gene which enables the expression of a polypeptide or protein with insecticidal properties. The heterologous gene in transgenic seeds can e.g. from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. This heterologous gene preferably comes from Bacillus sp., The gene product having an action against the European corn borer (European comborer) and / or Western Com rootworm. The heterologous gene particularly preferably comes from Bacillus thuringiensis.
Im Rahmen der vorliegenden Erfindung wird das erfindungsgemäße Mittel alleine oder in einer geeig neten Formulierung auf das Saatgut aufgebracht. Vorzugsweise wird das Saatgut in einem Zustand behandelt, in dem so stabil ist, dass keine Schäden bei der Behandlung auftreten. Im Allgemeinen kann die Behandlung des Saatguts zu jedem Zeitpunkt zwischen der Ernte und der Aussaat erfolgen.  In the context of the present invention, the agent according to the invention is applied to the seed alone or in a suitable formulation. The seed is preferably treated in a state in which it is so stable that no damage occurs during the treatment. In general, the seed can be treated at any time between harvesting and sowing.
Üblicherweise wird Saatgut verwendet, das von der Pflanze getrennt und von Kolben, Schalen, Stängeln, Hülle, Wolle oder Fruchtfleisch befreit wurde. So kann zum Beispiel Saatgut verwendet werden, das geerntet, gereinigt und bis zu einem Feuchtigkeitsgehalt von unter 15 Gew.-% getrocknet wurde. Alternativ kann auch Saatgut verwendet werden, das nach dem Trocknen z.B. mit Wasser behandelt und dann erneut getrocknet wurde. Im Allgemeinen muss bei der Behandlung des Saatguts darauf geachtet werden, dass die Menge des auf das Saatgut aufgebrachten erfindungsgemäßen Mittels und/oder weiterer Zusatzstoffe so gewählt wird, dass die Keimung des Saatguts nicht beeinträchtigt bzw. die daraus hervorgehende Pflanze nicht geschädigt wird. Dies ist vor allem bei Wirkstoffen zu beachten, die in bestimmten Aufwandmengen phytotoxische Effekte zeigen können. Usually, seeds are used that have been separated from the plant and freed of pistons, shells, stems, husk, wool or pulp. For example, seeds can be used that have been harvested, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, seeds can be used that have been treated with water after drying and then dried again. In general, when treating the seed, care must be taken that the amount of the agent and / or other additives according to the invention applied to the seed is selected so that the germination of the seed is not impaired or the resulting plant is not damaged. This is particularly important for active substances that can show phytotoxic effects at certain application rates.
Die erfindungsgemäßen Mittel können unmittelbar aufgebracht werden, also ohne weitere The agents according to the invention can be applied directly, that is, without further ones
Komponenten zu enthalten und ohne verdünnt worden zu sein. In der Regel ist es vorzuziehen, die Mittel in Form einer geeigneten Formulierung auf das Saatgut aufzubringen. Geeignete Formulierungen und Verfahren für die Saatgutbehandlung sind dem Fachmann bekannt und werden z.B. in den folgenden Dokumenten beschrieben: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 Al, WO 2002/080675 Al, WO 2002/028186 A2. To contain components and without having been diluted. As a rule, it is preferable to apply the agents to the seeds in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to the person skilled in the art and are e.g. described in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430, US 5,876,739, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2.
Die erfindungsgemäßen Wirkstoffe können in die üblichen Beizmittel-Formulierungen überführt werden, wie Lösungen, Emulsionen, Suspensionen, Pulver, Schäume, Slurries oder andere Hüllmassen für Saatgut, sowie ULV-Formulierungen. The active compounds according to the invention can be converted into the customary mordant formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seeds, and also ULV formulations.
Diese Formulierungen werden in bekannter Weise hergestellt, indem man die Wirkstoffe mit üblichen Zusatzstoffen vermischt, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder These formulations are prepared in a known manner by mixing the active ingredients with conventional additives, such as conventional extenders and solvents or
Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konser vierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser. Diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
Als Farbstoffe, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle für derartige Zwecke üblichen Farbstoffe in Betracht. Dabei sind sowohl in Wasser wenig lösliche Pigmente als auch in Wasser lösliche Farbstoffe verwendbar. Als Beispiele genannt seien die unter den Bezeichnungen Rhodamin B, C.I. Pigment Red 112 und C.I. Solvent Red 1 bekannten Farbstoffe.  Suitable dyes which can be contained in the mordant formulations which can be used according to the invention are all dyes customary for such purposes. Both pigments that are sparingly soluble in water and dyes that are soluble in water can be used. Examples include those under the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
Als Netzmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin- Sulfonate, wie Diiso- propyl- oder Diisobutyl-naphthalin-Sulfonate. Suitable wetting agents which can be contained in the mordant formulations which can be used according to the invention are all substances which promote wetting and are customary for the formulation of agrochemical active ingredients. Alkyl naphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates, can preferably be used.
Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Beizmittel- Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen The dispersants and / or emulsifiers which can be contained in the mordant formulations which can be used according to the invention are all used to formulate agrochemicals
Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vor zugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid-Propylenoxid Blockpolymere, Alkylphenolpolyglykolether sowie Tristryryl- phenolpolyglykolether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat- Formaldehydkondensate. Active ingredients conventional nonionic, anionic and cationic dispersants into consideration. Nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants can preferably be used. Suitable nonionic dispersants are especially ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are, in particular, lignin sulfonates, polyacrylic acid salts and aryl sulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. The mordant formulations which can be used according to the invention can contain, as defoamers, all of the foam-inhibiting substances which are customary for the formulation of agrochemical active compounds. Silicone defoamers and magnesium stearate can preferably be used.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. All substances which can be used for such purposes in agrochemical compositions can be present as preservatives in the mordant formulations which can be used according to the invention. Examples include dichlorophene and benzyl alcohol hemiform.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Beizmittel-Formu- lierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Secondary thickeners which can be contained in the mordant formulations which can be used according to the invention are all substances which can be used in agrochemical compositions for such purposes. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and highly disperse silica are preferred.
Als Kleber, die in den erfindungsgemäß verwendbaren Beizmittel-Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Suitable adhesives which can be contained in the mordant formulations which can be used according to the invention are all binders customarily used in mordants. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose are preferred.
Die erfindungsgemäß verwendbaren Beizmittel-Formulierungen können entweder direkt oder nach vor herigem Verdünnen mit Wasser zur Behandlung von Saatgut der verschiedensten Art, auch von Saatgut transgener Pflanzen, eingesetzt werden. Dabei können im Zusammenwirken mit den durch Expression gebildeten Substanzen auch zusätzliche synergistische Effekte auftreten. The mordant formulations which can be used according to the invention can be used either directly or after prior dilution with water for treating a wide variety of seeds, including seeds of transgenic plants. In cooperation with the substances formed by expression, additional synergistic effects can also occur.
Zur Behandlung von Saatgut mit den erfindungsgemäß verwendbaren Beizmittel-Formulierungen oder den daraus durch Zugabe von Wasser hergestellten Zubereitungen kommen alle üblicherweise für die Beizung einsetzbaren Mischgeräte in Betracht lm einzelnen geht man bei der Beizung so vor, dass man das Saatgut in einen Mischer gibt, die jeweils gewünschte Menge an Beizmittel-Formulierungen entweder als solche oder nach vorherigem Verdünnen mit Wasser hinzufügt und bis zur gleichmäßigen Verteilung der Formulierung auf dem Saatgut mischt. Gegebenenfalls schließt sich ein Trocknungs vorgang an. For the treatment of seeds with the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by adding water, all mixing devices which can usually be used for dressing can be considered. In particular, the dressing is carried out by placing the seeds in a mixer which Add the desired amount of seed dressing formulations either as such or after prior dilution with water and mix until the formulation is evenly distributed on the seed. If necessary, a drying process follows.
Die erfindungsgemäßen Wirkstoffe eignen sich bei guter Pflanzenverträglichkeit, günstiger The active compounds according to the invention are more suitable if they are well tolerated by plants
Warmblütertoxizität und guter Umweltverträglichkeit zum Schutz von Pflanzen und Pflanzenorganen, zur Steigerung der Emteerträge, Verbesserung der Qualität des Emtegutes. Sie können vorzugsweise als Pflanzenschutzmittel eingesetzt werden. Sie sind gegen normal sensible und resistente Arten sowie gegen alle oder einzelne Entwicklungsstadien wirksam. Warmblood toxicity and good environmental compatibility to protect plants and plant organs, to increase the crop yield, improve the quality of the crop. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
Als Pflanzen, welche erfindungsgemäß behandelt werden können, seien folgende Hauptanbaupflanzen erwähnt: Mais, Sojabohne, Baumwolle, Brassica Ölsaaten wie Brassica napus (z.B. Canola), Brassica rapa, B. juncea (z.B. (Acker-)Senf) und Brassica carinata, Reis, Weizen Zuckerrübe, Zurckerrohr,The following main crops may be mentioned as plants which can be treated according to the invention: maize, soybean, cotton, Brassica oilseeds such as Brassica napus (for example Canola), Brassica rapa, B. juncea (for example (field) mustard) and Brassica carinata, rice, Wheat sugar beet, sugar cane,
Hafer, Roggen, Gerste, Hirse, Triticale, Flachs, Wein und verschiedene Früchte und Gemüse von verschiedenen botanischen Taxa wie z.B. Rosaceae sp. (beispielsweise Kernfrüchte wie Apfel und Birne, aber auch Steinfrüchte wie Aprikosen, Kirschen, Mandeln und Pfirsiche und Beerenfrüchte wie Erdbeeren), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (beispielsweise Oats, rye, barley, millet, triticale, flax, wine and various fruits and vegetables from various botanical taxa such as Rosaceae sp. (for example pome fruits such as apple and pear, but also stone fruits such as apricots, cherries, almonds and peaches and berries such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example
Bananenbäume und -plantagen), Rubiaceae sp. (beispielsweise Kaffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (beispielsweise Zitronen, Organen und Grapefruit); Solanaceae sp. (beispielsweise Tomaten, Kartoffeln, Pfeffer, Auberginen), Liliaceae sp., Compositae sp. (beispielsweise Salat, Artischocke and Chicoree - einschließlich Wurzelchicoree, Endivie oder gemeinen Chicoree), Umbelliferae sp. (beispielsweise Karrotte, Petersilie, Stangensellerie und Knollensellerie), Banana trees and plantations), Rubiaceae sp. (e.g. coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g. lemons, organs and grapefruit); Solanaceae sp. (for example tomatoes, potatoes, pepper, eggplants), Liliaceae sp., Compositae sp. (for example, lettuce, artichoke and chicory - including root chicory, endive or common chicory), Umbelliferae sp. (e.g. carrot, parsley, celery and tuber celery),
Cucurbitaceae sp. (beispielsweise Gurke - einschließlich Gewürzgurke, Kürbis, Wassermelone, Flaschenkürbis und Melonen), Alliaceae sp. (beispielsweise Lauch und Zwiebel), Cruciferae sp. Cucurbitaceae sp. (for example cucumber - including pickled cucumber, pumpkin, watermelon, bottle gourd and melons), Alliaceae sp. (for example leek and onion), Cruciferae sp.
(beispielsweise Weißkohl, Rotkohl, Brokkoli, Blumenkohl, Rosenkohl, Pak Choi, Kohlrabi, (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi,
Radieschen, Meerrettich, Kresse und Chinakohl), Leguminosae sp. (beispielsweise Erdnüsse, Erbsen, und Bohnen - wie z.B. Stangenbohne und Ackerbohne), Chenopodiaceae sp. (beispielsweise Mangold, Futterrübe, Spinat, Rote Rübe), Malvaceae (beispielsweise Okra), Asparagaceae (beispielsweise Spargel); Nutzpflanzen und Zierpflanzen in Garten und Wald; sowie jeweils genetisch modifizierte Arten dieser Pflanzen.  Radishes, horseradish, cress and Chinese cabbage), Leguminosae sp. (e.g. peanuts, peas, and beans - such as runner bean and field bean), Chenopodiaceae sp. (for example Swiss chard, beet, spinach, beet), Malvaceae (for example okra), Asparagaceae (for example asparagus); Useful plants and ornamental plants in garden and forest; as well as genetically modified species of these plants.
Wie oben erwähnt, können erfindungsgemäß alle Pflanzen und deren Teile behandelt werden ln einer bevorzugten Ausführungsform werden wild vorkommende oder durch konventionelle biologische Zuchtmethoden, wie Kreuzung oder Protoplastenfusion erhaltenen Pflanzenarten und Pflanzensorten sowie deren Teile behandelt. In einer weiteren bevorzugten Ausführungsform werden transgene Pflanzen und Pflanzensorten, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden (Genetically Modified Organisms) und deren Teile behandelt. Der Begriff„Teile“ bzw.„Teile von Pflanzen“ oder„Pflanzenteile“ wurde oben erläutert. Besonders bevorzugt werden erfindungsgemäß Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen As mentioned above, according to the invention, all plants and their parts can be treated. In a preferred embodiment, wild plant species and plant cultivars and their parts obtained by conventional organic breeding methods, such as hybridization or protoplast fusion, are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms) and their parts are treated. The term “parts” or “parts of plants” or “parts of plants” was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant varieties are plants with new ones
Eigenschaften („Traits“), die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Properties ("traits"), both by conventional breeding, by mutagenesis or by recombinant DNA techniques have been grown. These can be varieties, breeds, organic and
Genotypen sein. Be genotypes.
Das erfindungsgemäße Behandlungsverfahren kann für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das Zellkemgenom, das The treatment method according to the invention can be used for the treatment of genetically modified organisms (GMOs), e.g. B. plants or seeds can be used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene which is provided or assembled outside the plant and which, when introduced into the cell nucleus genome, the
Chloropiastengenom oder das Mitochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, dass es ein interessierendes Protein oder Polypeptid exprimiert oder dass es ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense-Technologie, Cosuppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet. Chloropiastene genome or the mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down-regulating or genes in the plant or genes in the plant switches off (for example by means of antisense technology, cosuppression technology or RNAi technology [RNA interference]). A heterologous gene that is present in the genome is also called a transgene. A transgene that is defined by its specific presence in the plant genome is called a transformation or transgenic event.
In Abhängigkeit von den Pflanzenarten oder Pflanzensorten, ihrem Standort und ihren Depending on the plant species or plant varieties, their location and their
Wachstumsbedingungen (Böden, Klima, Vegetationsperiode, Ernährung) kann die erfindungsgemäße Behandlung auch zu überadditiven ("synergistischen") Effekten führen. So sind zum Beispiel die folgenden Effekte möglich, die über die eigentlich zu erwartenden Effekte hinausgehen: verringerte Aufwandmengen und/oder erweitertes Wirkungsspektrum und/oder erhöhte Wirksamkeit der Wirkstoffe und Zusammensetzungen, die erfindungsgemäß eingesetzt werden können, besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegenüber Treatment conditions according to the invention can also lead to superadditive ("synergistic") effects in growth conditions (soils, climate, growing season, nutrition). For example, the following effects are possible that go beyond the effects that are actually to be expected: reduced application rates and / or expanded spectrum of activity and / or increased effectiveness of the active compounds and compositions which can be used according to the invention, better plant growth, increased tolerance to high or low Temperatures, increased tolerance to
Trockenheit oder Wasser- oder Bodensalzgehalt, erhöhte Blühleistung, Emteerleichterung, Dryness or water or soil salt content, increased flowering performance, easier harvesting,
Reifebeschleunigung, höhere Erträge, größere Früchte, größere Pflanzenhöhe, intensiver grüne Farbe des Blatts, frühere Blüte, höhere Qualität und/oder höherer Nährwert der Emteprodukte, höhere Zuckerkonzentration in den Früchten, bessere Lagerfähigkeit und/oder Verarbeitbarkeit der Accelerated ripening, higher yields, larger fruits, higher plant height, more intense green color of the leaf, earlier flowering, higher quality and / or higher nutritional value of the edible products, higher sugar concentration in the fruits, better storage stability and / or processability of the
Emteprodukte. Harvested products.
Zu Pflanzen und Pflanzensorten, die vorzugsweise erfindungsgemäß behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Plants and plant varieties which are preferably treated according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful traits (regardless of whether this was achieved by breeding and / or biotechnology).
Beispiele für Nematoden-resistente Pflanzen sind z.B. folgenden US Patentanmeldungen beschrieben: 11/765,491, 11/765,494, 10/926,819, 10/782,020, 12/032,479, 10/783,417, 10/782,096, 11/657,964, 12/192,904, 11/396,808, 12/166,253, 12/166,239, 12/166,124, 12/166,209, 11/762,886, 12/364,335, 11/763,947, 12/252,453, 12/209,354, 12/491,396 und 12/497,221. Pflanzen, die erfindungsgemäß behandelt werden können, sind Hybridpflanzen, die bereits die Examples of nematode-resistant plants are described, for example, in the following US patent applications: 11 / 765,491, 11 / 765,494, 10 / 926,819, 10 / 782,020, 12 / 032,479, 10 / 783,417, 10 / 782,096, 11 / 657,964, 12 / 192,904, 11 / 396.808, 12 / 166.253, 12 / 166.239, 12 / 166.124, 12 / 166.209, 11 / 762.886, 12 / 364.335, 11 / 763.947, 12 / 252.453, 12 / 209.354, 12 / 491.396 and 12 / 497.221. Plants that can be treated according to the invention are hybrid plants that already have the
Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im Allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Resistenz gegen biotische und abiotische Stressfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, dass man eine ingezüchtete pollensterile Eltemlinie (den weiblichen Kreuzungspartner) mit einer anderen Express properties of the heterosis or hybrid effect, which generally leads to higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants are typically created by crossing one inbred male-sterile parent line (the female crossing partner) with another
ingezüchteten pollenfertilen Eltemlinie (dem männlichen Kreuzungspartner) kreuzt. Das Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d.h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Pollensterilität auf genetischen Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpflanzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, dass die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, dass die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Hybridpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica- Arten beschrieben. Genetische Determinanten für Pollensterilität können jedoch auch im Zellkemgenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Bamase selektiv in den Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden. crosses inbred pollen fertile parent line (the male crossing partner). The hybrid seeds are typically harvested from the male-sterile plants and sold to propagators. Pollen-sterile plants can sometimes (e.g. in maize) be produced by detasseling (i.e. mechanically removing the male genital organs or the male flowers); however, it is more common for pollen sterility to be based on genetic determinants in the plant genome. In this case, especially when the desired product is seeds because one wants to harvest from the hybrid plants, it is usually beneficial to ensure that pollen fertility in hybrid plants contains the genetic determinants responsible for pollen sterility , is completely restored. This can be achieved by ensuring that the male crossing partners have appropriate fertility restorer genes that are capable of restoring pollen fertility in hybrid plants that contain the genetic determinants responsible for male sterility. Genetic determinants for male sterility can be localized in the cytoplasm. Examples of cytoplasmic pollen sterility (CMS) have been described, for example, for Brassica species. However, genetic determinants for male sterility can also be localized in the cell core genome. Pollen-sterile plants can also be obtained using methods of plant biotechnology, such as genetic engineering. A particularly favorable means for producing male-sterile plants is described in WO 89/10396, where, for example, a ribonuclease such as a bamase is selectively expressed in the tapetum cells in the stamens. Fertility can then be restored in the tapetum cells by expression of a ribonuclease inhibitor such as Barstar.
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die erfindungsgemäß behandelt werden können, sind herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden. Plants or plant cultivars (which are obtained using methods of plant biotechnology, such as genetic engineering) which can be treated according to the invention are herbicide-tolerant plants, i.e. H. Plants that have been made tolerant to one or more specified herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation that confers such herbicide tolerance.
Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. Pflanzen können mit verschiedenen Methoden tolerant gegenüber Glyphosate gemacht werden. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5- Enolpyruvylshikimat-3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS-Gene sind das AroA-Gen (Mutante CT7) des Bakterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), das CP4-Gen des Bakteriums Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., 1986, Science 233, 478-481), für eine EPSPS aus der Tomate (Gasser et al., 1988, J. Biol. Chem. 263, 4280- 4289) oder für eine EPSPS aus Eleusine (WO 01/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln. Glyphosate-tolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym kodiert. Glyphosate-tolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate- acetyltransferase-Enzym kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene enthalten, selektiert. Pflanzen, die EPSPS Gene, welche Glyphosate-Toleranz verleihen, exprimieren, sind beschrieben. Pflanzen, welche andere Gene, die Glyphosate-Toleranz verleihen, z.B. Decarboxylase- Gene, sind beschrieben. Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants which have been made tolerant to the herbicide glyphosate or its salts. Plants can be made tolerant of glyphosate using various methods. For example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., 1983, Science 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., 1992, Curr. Topics Plant Physiol. 7, 139-145), the genes for an EPSPS from the petunia (Shah et al., 1986, Science 233, 478-481) for an EPSPS code from the tomato (Gasser et al., 1988, J. Biol. Chem. 263, 4280-4289) or for an EPSPS from Eleusine (WO 01/66704). It can also be a mutated EPSPS. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate oxidoreductase enzyme. Glyphosate-tolerant plants can also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme. Glyphosate-tolerant plants can also be obtained by selecting plants that contain naturally occurring mutations in the above-mentioned genes. Plants that express EPSPS genes that confer glyphosate tolerance are described. Plants which have other genes which confer glyphosate tolerance, for example decarboxylase genes, have been described.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Bialaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, dass man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Other herbicide-resistant plants are, for example, plants which have been made tolerant to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme that detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme that is used for a
Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat-Protein aus Streptomyces- Arten). Pflanzen, die eine exogene Phosphinotricin-acetyltransferase exprimieren, sind beschrieben. Encodes phosphinotricin acetyltransferase (such as the bar or pat protein from Streptomyces species). Plants that express an exogenous phosphinotricin acetyltransferase have been described.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Other herbicide-tolerant plants are also plants which have been made tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Both
Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para- Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes oder chimäres HPPD-Enzym kodiert, transformiert werden, wie in WO 96/38567, WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 oder US 6,768,044 beschrieben. Eine Toleranz gegenüber HPPD-Hemmern kann auch dadurch erzielt werden, dass man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD-Enzyms durch den HPPD- Hemmer ermöglichen. Solche Pflanzen sind in WO 99/34008 und WO 02/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, dass man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase-Enzym kodiert, wie in WO 2004/024928 beschrieben ist. Außerdem können Pflanzen noch toleranter gegen HPPD-Hemmern gemacht werden, indem man ein Gen in ihr Genom einfügt, welches für ein Enzym kodiert, das HPPD-Hemmer metabolisiert oder abbaut, wie z.B. CYP450 Enzyme (siehe WO 2007/103567 und WO 2008/150473). Hydroxyphenylpyruvate dioxygenases are enzymes that catalyze the reaction in which para-hydroxyphenylpyruvate (HPP) is converted to homogenate. Plants that are tolerant to HPPD inhibitors can be transformed with a gene encoding a naturally occurring resistant HPPD enzyme or a gene encoding a mutated or chimeric HPPD enzyme, as in WO 96/38567 , WO 99/24585, WO 99/24586, WO 2009/144079, WO 2002/046387 or US 6,768,044. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes that code for certain enzymes that enable the formation of homogenate despite the inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants are described in WO 99/34008 and WO 02/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants, in addition to a gene which codes for an HPPD-tolerant enzyme, with a gene which codes for a prephenate dehydrogenase enzyme, as in WO 2004/024928 is described. In addition, plants can be made more tolerant of HPPD inhibitors by using inserts a gene into their genome which codes for an enzyme which metabolizes or degrades HPPD inhibitors, such as CYP450 enzymes (see WO 2007/103567 and WO 2008/150473).
Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmem tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyl- triazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als Other herbicide-resistant plants are plants which have been made tolerant to acetolactate synthase (ALS) inhibitors. Known ALS inhibitors include, for example, sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen wie z.B. in Tranel und Wright (Weed Science 2002, 50, 700- 712) beschrieben ist. Die Herstellung von sulfonylhamstofftoleranten Pflanzen und Acetohydroxy acid synthase (AHAS, known) impart tolerance to different herbicides or groups of herbicides, such as in Tranel and Wright (Weed Science 2002, 50, 700 - 712). The production of plants tolerant of sulfonylurea and
imidazo linontoleranten Pflanzen ist beschrieben. Weitere Sulfonylharnstoff- und imidazo linontolerante Pflanzen sind auch beschrieben. imidazo linon-tolerant plants is described. Other sulfonylurea and imidazo linone tolerant plants are also described.
Weitere Pflanzen, die gegenüber Imidazolinonen und/oder Sulfonylharnstoffen tolerant sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden (vgl. z.B. für Sojabohne US 5,084,082, für Reis WO 97/41218, für Zuckerrübe US 5,773,702 und WO 99/057965, für Salat US 5,198,599 oder für Sonnenblume WO 01/065922). Further plants which are tolerant to imidazolinones and / or sulfonylureas can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding (cf. for example for soybean US 5,084,082, for rice WO 97/41218, for sugar beet US 5,773,702 and WO 99/057965, for salad US 5,198,599 or for sunflower WO 01/065922).
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind gegenüber abiotischen Stressfaktoren tolerant. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Stressresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Stresstoleranz zählen folgende: Plants or plant cultivars (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are tolerant of abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such stress resistance. Particularly useful plants with stress tolerance include the following:
a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Pflanzen zu reduzieren vermag. a. Plants which contain a transgene which is able to reduce the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants.
b. Pflanzen, die ein stresstoleranzfÖrdemdes Transgen enthalten, das die Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oder Pflanzenzellen zu reduzieren vermag; b. Plants which contain a stress tolerance-promoting transgene which is capable of reducing the expression and / or activity of the PARG-coding genes of the plants or plant cells;
c. Pflanzen, die ein stresstoleranzfÖrdemdes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage-Biosynthesewegs kodiert, darunter Nicotinamidase, Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotidadenyltransferase, Nicotinamidadenindinu- kleotidsynthetase oder Nicotinamidphosphoribosyltransferase. c. Plants that contain a stress-tolerant transgene that encodes a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase, nicotinamidinamide transidiboribinotinosinodidase niborotinosinodinase diborobenzylase.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Emteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Emteprodukts auf, wie zum Beispiel: 1) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch-physi kalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin-Verhältnisses, des Verzweigungsgrads, der durchschnittlichen Kettenlänge, der Verteilung der Seitenketten, des Plants or plant cultivars (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, have a changed amount, quality and / or storability of the edged product and / or changed properties of certain constituents of the edged product, such as: 1) Transgenic plants that synthesize a modified starch, the chemical-physical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the side chains, the
Viskositätsverhaltens, der Gelfestigkeit, der Stärkekomgröße und/oder Stärkekommorphologie im Vergleich mit der synthetisierten Stärke in Wildtyppflanzenzellen oder -pflanzen verändert ist, so dass sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Viscosity behavior, the gel strength, the starch size and / or starch comorphology is changed compared to the synthesized starch in wild type plant cells or plants, so that this modified starch is more suitable for certain applications.
2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder  2) transgenic plants that synthesize non-starch carbohydrate polymers, or
Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des lnulin- und Levantyps, produzieren, Pflanzen, die alpha-l,4-Glucane produzieren, Pflanzen, die alpha- l,6-verzweigte alpha-l,4-Glucane produzieren und Pflanzen, die Alteman produzieren. Non-starch carbohydrate polymers, the properties of which have changed in comparison to wild type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, plants which produce alpha-1,4-glucans, plants which produce alpha-1,4-branched alpha-1,4-glucans and plants which Produce Alteman.
3) Transgene Pflanzen, die Hyaluronan produzieren.  3) Transgenic plants that produce hyaluronan.
4) Transgene Pflanzen oder Hybridpflanzen wie Zwiebeln mit bestimmten Eigenschaften wie „hohem Anteil an löslichen Feststoffen“ (,high soluble solids content’), geringe Schärfe (,low pungency’, LP) und/oder lange Lagerfähigkeit (,long storage’, LS).  4) Transgenic plants or hybrid plants such as onions with certain properties such as "high soluble solids content" ("high soluble solids content"), low sharpness ("low pungency", LP) and / or long shelf life ("long storage", LS ).
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie  Plants or plant varieties (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as
Baumwollpflanzen mit veränderten Fasereigenschaften. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen: Cotton plants with changed fiber properties. Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which confers such modified fiber properties; these include:
a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Cellulosesynthasegenen enthalten, a) plants, such as cotton plants, which contain a modified form of cellulose synthase genes,
b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3 -homologen Nukleinsäuren enthalten, wie Baumwollpflanzen mit einer erhöhten Expression der Saccharosephosphatsyn- thase; b) Plants such as cotton plants which contain a modified form of rsw2 or rsw3 homologous nucleic acids, such as cotton plants with an increased expression of sucrose phosphate synthase;
c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Saccharosesynthase; c) plants such as cotton plants with an increased expression of sucrose synthase;
d) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Herunterregulieren der faserselektiven ß-l,3-Glucanase; e) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen. d) Plants such as cotton plants in which the timing of the passage control of the plasmodesms at the base of the fiber cell is changed, e.g. B. by down-regulating the fiber-selective β-1,3-glucanase; e) Plants such as cotton plants with fibers with changed reactivity, e.g. B. by expression of the N-acetylglucosamine transferase gene, including nodC, and of chitin synthase genes.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen: Plants or plant cultivars (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with changed properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants which contain a mutation which imparts such altered oil properties; these include:
a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen Ölsäuregehalt produziere; b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren. a) Plants such as oilseed rape plants that produce oil with a high oleic acid content; b) Plants such as rapeseed plants that produce oil with a low linolenic acid content.
c) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen gesättigten Fettsäuregehalt produzieren. Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten werden können), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie Kartoffeln, welche Virus-resistent sind z.B. gegen den Kartoffelvirus Y (Event SY230 und SY233 von Tecnoplant, Argentinien), oder welche resistent gegen Krankheiten wie die Kraut- und Knollenfäule (potato late blight) (z.B. RB Gen), oder welche eine verminderte kälteinduzierte Süße zeigen (welche die Gene Nt-Inh, II-INV tragen) oder welche den Zwerg-Phänotyp zeigen (Gen A-20 Oxidase). c) Plants such as oilseed rape plants that produce oil with a low saturated fatty acid content. Plants or plant varieties (which can be obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as potatoes which are virus-resistant, e.g. against the potato virus Y (event SY230 and SY233 from Tecnoplant, Argentina), or which are resistant to diseases such as late blight (potato late blight) (e.g. RB gene), or which show a reduced cold-induced sweetness (which the genes Nt- Inh, carry II-INV) or which show the dwarf phenotype (gene A-20 oxidase).
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls erfindungsgemäß behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften im Samenausfall (seed shattering). Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Eigenschaften verleihen, und umfassen Pflanzen wie Raps mit verzögertem oder vermindertem Samenausfall.  Plants or plant cultivars (which were obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated according to the invention, are plants such as oilseed rape or related Brassica plants with altered properties in seed loss (seed shattering). Such plants can be genetically transformed or selected from plants containing a mutation that confer such altered properties and include plants such as oilseed rape with delayed or reduced seed loss.
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen mit Transformationsevents oder Kombinationen von Transformationsevent, welche in den USA beim Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) Gegenstand von erteilten oder anhängigen Petitionen für den nicht-regulierten Status sind. Die Information hierzu ist jederzeit beim APHIS (4700 River Road Riverdale, MD 20737, USA) erhältlich, z.B. über die Intemetseite http://www.aphis.usda.gov/brs/not_reg.html. Am Anmeldetag dieser Particularly useful transgenic plants which can be treated according to the invention are plants with transformation events or combinations of transformation events which have been issued or pending petitions by the Animal and Plant Health Inspection Service (APHIS) of the United States Department of Agriculture (USDA) for the unregulated status. Information on this is available at any time from APHIS (4700 River Road Riverdale, MD 20737, USA), e.g. via the website http://www.aphis.usda.gov/brs/not_reg.html. On the filing date of this
Anmeldung waren beim APHIS die Petitionen mit folgenden Informationen entweder erteilt oder anhängig: At the APHIS the petitions were either issued or pending with the following information:
- Petition: Identifikationsnummer der Petition. Die Technische Beschreibung des Transformations events kann im einzelnen Petitionsdokument erhältlich von APHIS auf der Website über die  - Petition: identification number of the petition. The technical description of the transformation event can be obtained from APHIS on the website via the individual petition document
Petitionsnummer gefunden werden. Diese Beschreibungen sind hiermit per Referenz offenbart. Petition number can be found. These descriptions are hereby disclosed by reference.
- Erweiterung einer Petition: Referenz zu einer frühere Petition, für die eine Erweiterung oder Verlängerung beantragt wird.  - Extension of a petition: reference to a previous petition for which an extension or extension is requested.
- Institution: Name der die Petition einreichenden Person.  - Institution: name of the person submitting the petition.
- Regulierter Artikel: die betroffen Pflanzenspecies.  - Regulated article: the affected plant species.
- Transgener Phänotyp: die Eigenschaft („Trait“), die der Pflanze durch das Transformationsevent verliehen wird.  - Transgenic phenotype: the trait that is given to the plant by the transformation event.
- Transformationevent oder -linie: der Name des oder der Events (manchmal auch als Linie(n) bezeichnet), für die der nicht-regulierte Status beantragt ist.  - Transformation event or line: the name of the event (s) (sometimes referred to as line (s)) for which the non-regulated status is requested.
- APHIS Documente: verschiedene Dokumente, die von APHIS bzgl. der Petition veröffentlicht warden oder von APHIS auf Anfrage erhalten werden können. Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® (Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link® (Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Sylfonylhamstoffioleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais). - APHIS Documente: various documents that have been published by APHIS regarding the petition or can be obtained from APHIS on request. Particularly useful transgenic plants which can be treated according to the invention are plants with one or more genes which code for one or more toxins, are the transgenic plants which are offered under the following trade names: YIELD GARD® (for example corn, cotton, Soybeans), KnockOut® (e.g. corn), BiteGard® (e.g. corn), BT-Xtra® (e.g. corn), StarLink® (e.g. corn), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (e.g. maize), Protecta® and NewLeaf® (potato). Herbicide-tolerant plants to be mentioned are, for example, maize varieties, cotton varieties and soybean varieties, which are offered under the following trade names: Roundup Ready® (glyphosate tolerance, for example maize, cotton, soybean), Liberty Link® (phosphinotricine tolerance, for example rapeseed) , IMI® (imidazolinone tolerance) and SCS® (Sylfonylurstoffioleranz), for example maize. The herbicide-resistant plants (plants bred traditionally to herbicide tolerance) that should be mentioned include the varieties offered under the name Clearfield® (for example maize).
Besonders nützliche transgene Pflanzen, die erfindungsgemäß behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind (siehe zum Beispiel http://gmoinfo.jrc.it/gmp_browse.aspx und Particularly useful transgenic plants which can be treated according to the invention are plants which contain transformation events or a combination of transformation events and which are listed, for example, in the files of various national or regional authorities (see, for example, http: / /gmoinfo.jrc.it/gmp_browse.aspx and
http://cera-gmc.org/index.php?evidcode=&hstlDXCode=&gType=&AbbrCode=&atCode=&stCode=&colDhttp://cera-gmc.org/index.php?evidcode=&hstlDXCode=&gType=&AbbrCode=&atCode=&stCode=&colD
Code=&action=gm_crop_database&mode=Submit). Code = & action = gm_crop_database & mode = Submit).
Biologische Beispiele: Biological examples:
A. Herbizide Wirkung im frühen Nachauflauf A. Early post-herbicidal effects
Samen von mono- bzw. dikotylen Unkrautpflanzen wurden in 96-well Mikrotiterplatten in Quarzsand ausgelegt und in der Klimakammer unter kontrollierten Wachstumsbedingungen angezogen. 5 bis 7 Tage nach der Aussaat wurden die Versuchspflanzen im Keimblattstadium behandelt. Die in Form von Emulsionskonzentraten (EC) formulierten erfindungsgemäßen Verbindungen wurden mit einer Wasseraufwandmenge von umgerechnet 2200 Liter pro Hektar appliziert. Nach 9 bis 12 Tagen Standzeit der Versuchspflanzen in der Klimakammer unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. In den nachstehenden Tabllen Al bis A5 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.137 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1900 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. Seeds of monocotyledonous or dicotyledonous weed plants were laid out in 96-well microtiter plates in quartz sand and grown in the climatic chamber under controlled growth conditions. 5 to 7 days after sowing, the test plants were treated at the cotyledon stage. The compounds according to the invention formulated in the form of emulsion concentrates (EC) were applied with a water application rate of the equivalent of 2200 liters per hectare. After the test plants had stood in the climatic chamber for 9 to 12 days under optimal growth conditions, the effect of the preparations was assessed visually in comparison to untreated controls. For example, 100% activity = plants have died, 0% activity = like control plants. The following tables A1 to A5 show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.137 on various harmful plants and an application rate corresponding to 1900 g / ha, which were obtained in accordance with the aforementioned test instructions.
Tabelle Al : Wirkung bei 1900 g/ha gegen Setaria viridis /SET VI) Table A1: Effect at 1900 g / ha against Setaria viridis / SET VI)
Figure imgf000154_0001
Tabelle A2: Wirkung bei 1900 g/ha gegen Diplotaxis tenuifolia (DIPTE)
Figure imgf000154_0001
Table A2: Effect at 1900 g / ha against Diplotaxis tenuifolia (DIPTE)
Figure imgf000154_0002
Figure imgf000154_0002
Tabelle A3: Wirkung bei 1900 g/ha gegen Matricaria chamonilla (MATCH) Table A3: Effect at 1900 g / ha against Matricaria chamonilla (MATCH)
Figure imgf000154_0003
Figure imgf000154_0003
Tabelle A4: Wirkung bei 1900 g/ha gegen Stellaria media (STEME) Table A4: Effect at 1900 g / ha against Stellaria media (STEME)
Figure imgf000154_0004
Figure imgf000154_0004
Tabelle A5: Wirkung bei 1900 g/ha gegen Veronica persica (VERPE) Table A5: Effect at 1900 g / ha against Veronica persica (VERPE)
Figure imgf000154_0005
Wie die Ergebnisse zeigten, weisen erfindungsgemäße Verbindungen, wie beispielsweise die
Figure imgf000154_0005
As the results showed, compounds according to the invention, such as the
Verbindungen Nr. 1.1-2, 1.1-15, 1.1-58, 1.1-65, 1.136-15 und andere Verbindungen aus den Tabellen 1.1 bis 1.137, bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf. Beispielsweise haben dabei die Verbindungen Nr. 1.1-2, 1.1-15, 1.1-58, 1.1-65 und 1.136-15 im Compounds No. 1.1-2, 1.1-15, 1.1-58, 1.1-65, 1.136-15 and other compounds from Tables 1.1 to 1.137, when treated post-emergence, have good herbicidal activity against harmful plants. For example, the compounds Nos. 1.1-2, 1.1-15, 1.1-58, 1.1-65 and 1.136-15 have
Nachauflaufverfahren eine sehr gute herbizide Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Diplotaxis tenuifolia , Matricaria chamonilla , Setaria viridis, Stellaria media und Veronica persica bei einer Aufwandmenge von 1900 g Aktivsubstanz pro Hektar. Post-emergence method has a very good herbicidal activity (80% to 100% herbicidal activity) against harmful plants such as Diplotaxis tenuifolia, Matricaria chamonilla, Setaria viridis, Stellaria media and Veronica persica at a rate of 1900 g of active ingredient per hectare.
B. Herbizide Wirkung und Kulturverträglichkeit im Nachauflauf B. Post-emergence herbicidal activity and crop tolerance
Samen von mono- bzw. dikotylen Unkraut- bzw. Kulturpflanzen wurden in Kunststoff- oder organischen Pflanztöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter kontrollierten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat wurden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen wurden dann als wässrige Suspension bzw. Emulsion unter Zusatz von 0,5% Additiv mit einer Wasseraufwandmenge von umgerechnet 600 1/ha auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus, unter optimalen Wachstumsbedingungen, wurde die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert. Beispielsweise bedeutet 100% Wirkung = Pflanzen sind abgestorben, 0% Wirkung = wie Kontrollpflanzen. Seeds of monocotyledonous or dicotyledonous weed or crop plants were placed in plastic or organic plant pots in sandy loam soil, covered with soil and grown in the greenhouse under controlled growth conditions. The test plants were treated at the single-leaf stage 2 to 3 weeks after sowing. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) were then sprayed onto the green parts of the plant as an aqueous suspension or emulsion with the addition of 0.5% additive with a water application rate of 600 l / ha. After the test plants had stood in the greenhouse for about 3 weeks under optimal growth conditions, the effect of the preparations was assessed visually in comparison with untreated controls. For example, 100% activity = plants have died, 0% activity = like control plants.
In den nachstehenden Tabllen Bl bis B6 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.137 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 320 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. The following tablets B1 to B6 show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.137 on various harmful plants and an application rate corresponding to 320 g / ha, which were obtained in accordance with the aforementioned test instructions.
Tabelle Bl Table Bl
Figure imgf000155_0001
Figure imgf000155_0001
Figure imgf000156_0001
Figure imgf000156_0001
Tabelle B2
Figure imgf000156_0002
Table B2
Figure imgf000156_0002
Tabelle B3
Figure imgf000156_0003
Table B3
Figure imgf000156_0003
Tabelle B4
Figure imgf000156_0004
Table B4
Figure imgf000156_0004
Tabelle B5
Figure imgf000156_0005
Figure imgf000157_0001
Table B5
Figure imgf000156_0005
Figure imgf000157_0001
Tabelle B6 Table B6
Figure imgf000157_0002
Figure imgf000157_0002
Wie die Ergebnisse zeigten, weisen erfindungsgemäße Verbindungen, wie beispielsweise die As the results showed, compounds according to the invention, such as the
Verbindungen Nr. 1.4-15, 1.2-15, 1.1-9, 1.9-9a, I.l36-9a, I. l36-9b, 1.135-15, 1.1-16, 1.3-16, 1. l37-9a, 1.9- 9b, I.3-9a, 1.11-16, 1.3-15, 1. l5-9a, 1.6-16, 1.1-46, 1.1-1 und andere aufgeführte Verbindungen aus den Tabellen 1.1 bis 1.137 bei Behandlung im Nachauflauf eine gute herbizide Wirksamkeit gegen Compounds No. 1.4-15, 1.2-15, 1.1-9, 1.9-9a, I.l36-9a, I. l36-9b, 1.135-15, 1.1-16, 1.3-16, 1. l37-9a, 1.9 - 9b, I.3-9a, 1.11-16, 1.3-15, 1. l5-9a, 1.6-16, 1.1-46, 1.1-1 and other listed compounds from Tables 1.1 to 1.137 are good for post-emergence treatment herbicidal activity against
Schadpflanzen auf. Beispielsweise haben dabei die Verbindungen Nr. 1.4-15, 1.2-15, 1.1-9, 1.9-9a, 1.136- 9a, I. l36-9b, 1.135-15, 1.1-16, 1.3-16, 1. l37-9a, I.9-9b, I.3-9a, 1.11-16, 1.3-15, 1. l5-9a, 1.6-16, 1.1-46, 1.1-1 im Nachauflaufverfahren eine sehr gute herbizide Wirkung (80% bis 100% herbizide Wirkung) gegen Schadpflanzen wie Abutilon theophrasti, Amaranthus retroflexus, Polygonum convolvulus,Harmful plants. For example, compounds no. 1.4-15, 1.2-15, 1.1-9, 1.9-9a, 1.136-9a, I. 136-9b, 1.135-15, 1.1-16, 1.3-16, 1.137-9a , I.9-9b, I.3-9a, 1.11-16, 1.3-15, 1.15-9a, 1.6-16, 1.1-46, 1.1-1 in the post-emergence process a very good herbicidal activity (80% to 100 % herbicidal activity) against harmful plants such as Abutilon theophrasti, Amaranthus retroflexus, Polygonum convolvulus,
Setaria viridi , Stellaria media und Viola tricolor bei einer Aufwandmenge von 320 g Aktivsubstanz pro Hektar. Setaria viridi, Stellaria media and Viola tricolor at a rate of 320 g of active ingredient per hectare.

Claims

Patentansprüche : Claims:
1. Substituierte Heterocyclylpyrrolone der allgemeinen Formel (I) oder deren Salze 1. Substituted heterocyclylpyrrolones of the general formula (I) or their salts
Figure imgf000158_0001
Figure imgf000158_0001
worin  wherein
Q für die Gruppe Q for the group
Figure imgf000158_0002
steht
Figure imgf000158_0002
stands
A unabhängig voneinander für O (Sauerstoff), S (Schwefel) oder die Gruppierung NR10 oder C-RUR12 stehen, wobei R10, R1 1 und R12 in den Gruppierungen NR10 oder C-RUR12 jeweils gleiche oder verschiedene Bedeutungen gemäß der unten stehenden Definition haben, A independently represents O (oxygen), S (sulfur), the grouping or NR 10 or CR U R are 12, wherein R 10, R 1 1 and R 12 are identical or different meanings in the groups NR 10 or CR U R 12 according to the definition below,
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Halogen, Cyano, (Ci-Cg)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-Cg)-Hydroxyalkyl, ( C i - C s ) - Alkoxyalkyl, (Ci-Cg)-Alkoxy, (Ci-Cg)-Haloalkoxy, (Ci-C8)-Alkylthio, (Ci-Cs)- Haloalkylthio, Aryl, Heteroaryl, Aryloxy, Heteroaryloxy, Heterocyclyl, (C3-C10)- Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)- Halocycloalkyl-(Ci-C8)-alkyl, (Ci-Cg)-Alkylcarbonyl, (C2-Cg)-Alkenyl, (C2-C8)- Alkenyloxy, (C2-C8)-Alkinyl steht, R2 für Hydroxy, Hydrothio, Halogen, NR13R14, (Ci-Cg)-Alkoxy, (C3-Cio)-Cycloalkyl-R 1 for halogen, cyano, (Ci-Cg) -alkyl, (Ci-C8) -haloalkyl, (Ci-Cg) -hydroxyalkyl, (C i - C s) - alkoxyalkyl, (Ci-Cg) -alkoxy, ( Ci-Cg) -haloalkoxy, (Ci-C8) -alkylthio, (Ci-Cs) - haloalkylthio, aryl, heteroaryl, aryloxy, heteroaryloxy, heterocyclyl, (C 3 -C 10 ) - cycloalkyl, (C 3 -Cio) - Cycloalkyl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C8) -alkyl, (Ci-Cg) -alkylcarbonyl, (C 2 -Cg) alkenyl, (C 2 -C 8 ) alkenyloxy, (C 2 -C 8 ) alkynyl, R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-Cg) alkoxy, (C3-Cio) cycloalkyl-
(Ci-Cg)-alkoxy, Aryl-(Ci-Cg)-alkoxy, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkoxy, Arylcarbonyloxy, (Ci-Cg)-Alkylcarbonyloxy, Aryl-(Ci-Cg)-alkylcarbonyloxy, Heteroarylcarbonyloxy, (C3-Cio)-Cycloalkylcarbonyloxy, Heterocyclylcarbonyloxy, (Ci-Cg)-Haloalkyl- carbonyloxy, (C2-Cg)-Alkenylcarbonyloxy, OC(0)OR15, OC(0)SR16, OC(S)OR15, OC(S)SR16, 0S02R16, OSO2OR15, OCHO, 0C(0)NR13R14 steht, (Ci-Cg) -alkoxy, aryl- (Ci-Cg) -alkoxy, (Ci-Cg) -alkoxy- (Ci-Cg) -alkoxy, arylcarbonyloxy, (Ci-Cg) -alkylcarbonyloxy, aryl- (Ci-Cg ) -alkylcarbonyloxy, heteroarylcarbonyloxy, (C3-Cio) -cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-Cg) -haloalkylcarbonyloxy, (C 2 -Cg) -alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , 0S0 2 R 16 , OSO2OR 15 , OCHO, 0C (0) NR 13 R 14 ,
R3 für Wasserstoff, (Ci-Cg)-Alkyl steht, R 3 represents hydrogen, (Ci-Cg) alkyl,
R4, R5, R6, R7,R8 und R9 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-Cg)- Alkyl, (Ci-Cg)-Hydroxyalkyl, (Ci-Cg)-Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cg)- alkyl, Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-Cg)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)- Alkinyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, Arylcarbonyloxy-(Ci-Cg)-alkyl, Heteroarylcarbonyloxy-(Ci-Cg)-alkyl, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (Ci-Cg) - alkyl, (Ci-Cg) -hydroxyalkyl, (Ci-Cg) -haloalkyl, (C 3 -Cio) cycloalkyl, (C3-C10) cycloalkyl- (Ci-Cg) alkyl, (Ci-Cg) alkoxy, aryl, heteroaryl, heterocyclyl, aryl- (Ci-Cg) alkyl, heteroaryl - (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C2-Cg) -alkenyl, (C 2 -Cg) -alkynyl, (Ci-Cg) -alkoxycarbonyl- (Ci-Cg) - alkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -alkyl, arylcarbonyloxy- (Ci-Cg) -alkyl, heteroarylcarbonyloxy- (Ci-Cg) -alkyl,
Heterocyclylcarbonyloxy-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyloxy-(Ci-Cg)-alkyl, (C3-Cg)-Cycloalkylcarbonyloxy-(Ci-Cg)-alkyl, C(0)OR15, C(0)NR13R14, SR16, SOR16, SO2R16, NR13R14, Cyano stehen, oder wobei R4, R5, R6, R7,R8 und R9 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen gesättigten oder teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7-gliedrigen Ring bilden, Heterocyclylcarbonyloxy- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyloxy- (Ci-Cg) -alkyl, (C 3 -Cg) -cycloalkylcarbonyloxy- (Ci-Cg) -alkyl, C (0) OR 15 , C (0) NR 13 R 14 , SR 16 , SOR 16 , SO2R 16 , NR 13 R 14 , cyano, or where R 4 , R 5 , R 6 , R 7 , R 8 and R 9 together with the C- Atom to which they are each bonded form a saturated or partially saturated, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted, a total of 3-7-membered ring,
R10 für Wasserstoff, (Ci-Cg)-Alkyl, (Ci-Cg)-Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl-(Ci-Cg)-alkyl, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cg)-alkyl, R 10 is hydrogen, (Ci-Cg) alkyl, (Ci-Cg) haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -C 10 ) cycloalkyl (Ci-Cg) alkyl, aryl, Heteroaryl, heterocyclyl, aryl- (Ci-Cg) -alkyl,
Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-Cg)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (C4-Cio)-Cycloalkenyl, Aryl-(C2-Cg)-alkenyl, Heteroaryl-(C2-Cg)-alkenyl, Heterocyclyl-(C2-Cg)-alkenyl, Arylcarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl-(Ci-Cg)-alkyl, Heteroarylcarbonyl-(Ci-Cg)-alkyl, (C3-C10)- Cycloalkylcarbonyl-(Ci-Cg)-alkyl, Aryl-(Ci-Cg)-alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)- Alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Haloalkoxy-(Ci- Cg)-alkyl, (Ci-Cg)-Alkylcarbonyl, S02R16, CHO, C(0)OR15, R13R14N-(Ci-Cg)-alkyl oder Cyano-(Ci-Cg)-alkyl steht, Heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-Cg) -alkyl, (C2-Cg) -alkenyl, (C2-Cg) -alkynyl, (C2-Cg) -haloalkenyl, (C2-Cg) - Haloalkynyl, (C4-Cio) -cycloalkenyl, aryl- (C2-Cg) -alkenyl, heteroaryl- (C2-Cg) -alkenyl, heterocyclyl- (C2-Cg) -alkenyl, arylcarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl- (Ci-Cg) -alkyl, heteroarylcarbonyl- (Ci-Cg) -alkyl, (C 3 -C 10 ) - cycloalkylcarbonyl- (Ci-Cg) -alkyl, aryl- (Ci-Cg ) -alkoxycarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) - alkoxycarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -alkyl, (Ci-Cg) - Haloalkoxy- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyl, S0 2 R 16 , CHO, C (0) OR 15 , R 13 R 14 N- (Ci-Cg) -alkyl or cyano- (Ci -Cg) alkyl,
R11 und R12 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-Cg)-Alkyl, R 11 and R 12 independently of one another are hydrogen, hydroxyl, halogen, (Ci-Cg) -alkyl,
(Ci-Cg)-Haloalkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-Cg)-alkyl, (Ci-Cg)- Alkoxy, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-Cg)-alkyl, Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-Cg)-alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-Cg)-Alkoxycarbonyl- (Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, Arylcarbonyloxy-(Ci-Cg)-alkyl, (Ci-Cg) haloalkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- (Ci-Cg) alkyl, (Ci-Cg) - Alkoxy, aryl, heteroaryl, heterocyclyl, aryl (Ci-Cg) alkyl, heteroaryl (Ci-Cg) alkyl, heterocyclyl (Ci-Cg) alkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-Cg) alkoxycarbonyl- (Ci-Cg) alkyl, (Ci-Cg) alkoxy- (Ci-Cg) alkyl, arylcarbonyloxy- (Ci-Cg) alkyl,
Heteroarylcarbonyloxy-(Ci-Cg)-alkyl, Heterocyclylcarbonyloxy-(Ci-Cg)-alkyl, (Ci-Cg)- Alkylcarbonyloxy-(Ci-Cg)-alkyl, (C3-Cg)-Cycloalkylcarbonyloxy-(Ci-Cg)-alkyl, C(0)OR15, C(0)NR13R14, SR16, SOR16, S02R16, NR13R14, Cyano stehen, oder wobei R1 1 und R12 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7- gliedrigen Ring bilden, Heteroarylcarbonyloxy- (Ci-Cg) -alkyl, heterocyclylcarbonyloxy- (Ci-Cg) -alkyl, (Ci-Cg) -alkylcarbonyloxy- (Ci-Cg) -alkyl, (C 3 -Cg) -cycloalkylcarbonyloxy- (Ci-Cg) -alkyl, C (0) OR 15 , C (0) NR 13 R 14 , SR 16 , SOR 16 , S0 2 R 16 , NR 13 R 14 , cyano, or where R 1 1 and R 12 together with the C Atom to which they are each bonded form a partially saturated, in total 3-7-membered ring, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted,
R13 und R14 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cg)-R 13 and R 14 are the same or different and are independently hydrogen, (Ci-Cg) -
Alkyl, alkyl,
(C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-Cg)-Cyanoalkyl, (Ci-Cg)-Haloalkyl, (C2-Cg)- Haloalkenyl, (C2-Cg)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-Cg)-Cycloalkenyl, (Ci-Cg)- Alkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Haloalkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Alkylthio-(Ci-Cg)- alkyl, (Ci-Cg)-Haloalkylthio-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-haloalkyl, Aryl, Aryl-(Ci-Cg)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cg)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-Cg)- alkyl, (C4-Cg)-Cycloalkenyl-(Ci-Cg)-alkyl, S02R16, Heterocyclyl, (Ci-Cg)- Alkoxycarbonyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxycarbonyl, Aryl-(Ci-Cg)-Alkoxycarbonyl- (Ci-Cg)-alkyl, Aryl-(Ci-Cg)-Alkoxycarbonyl, Heteroaryl-(Ci-Cg)-Alkoxycarbonyl, (C2- Cg)-Alkenyloxycarbonyl, (C2-Cg)-Alkinyloxycarbonyl oder Heterocyclyl-(Ci-Cg)-alkyl stehen, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-Cg) cyanoalkyl, (Ci-Cg) haloalkyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) - Haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -Cg) cycloalkenyl, (Ci-Cg) - alkoxy- (Ci-Cg) -alkyl, (Ci-Cg) -haloalkoxy- (Ci-Cg) - alkyl, (Ci-Cg) -alkylthio- (Ci-Cg) -alkyl, (Ci-Cg) -haloalkylthio- (Ci-Cg) -alkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -haloalkyl, Aryl, aryl- (Ci-Cg) -alkyl, heteroaryl, heteroaryl- (Ci-Cg) -alkyl, (C 3 -Cio) -cycloalkyl- (Ci-Cg) -alkyl, (C 4 -Cg) -cycloalkenyl- (Ci-Cg) -alkyl, S0 2 R 16 , heterocyclyl, (Ci-Cg) - alkoxycarbonyl- (Ci-Cg) -alkyl, (Ci-Cg) -alkoxycarbonyl, aryl- (Ci-Cg) -alkoxycarbonyl- ( Ci-Cg) -alkyl, aryl- (Ci-Cg) -alkoxycarbonyl, heteroaryl- (Ci-Cg) -alkoxycarbonyl, (C 2 - Cg) -alkenyloxycarbonyl, (C 2 -Cg) -alkynyloxycarbonyl or heterocyclyl- (Ci Cg) alkyl,
R15 für (Ci-Cg)-Alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-Cg)-Cyanoalkyl, (Ci-Cg)- Haloalkyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-C10)- Cycloalkenyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-haloalkyl, Aryl, Aryl-(Ci-Cg)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cg)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-Cg)- alkyl, (C4-Cio)-Cycloalkenyl-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-Cg)-alkyl, (C2- Cg)-Alkenyloxycarbonyl-(Ci-Cg)-alkyl, Aryl-(Ci-Cg)-Alkoxycarbonyl-(Ci-Cg)-alkyl, Hydroxycarbonyl-(Ci-Cg)-alkyl, Heterocyclyl oder Heterocyclyl-(Ci-Cg)-alkyl steht, R 15 is for (Ci-Cg) alkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-Cg) cyanoalkyl, (Ci-Cg) haloalkyl, (C 2 -Cg ) -Haloalkenyl, (C 2 -Cg) -haloalkynyl, (C 3 -Cio) -cycloalkyl, (C 4 -C 10 ) -cycloalkenyl, (Ci-Cg) -alkoxy- (Ci-Cg) -alkyl, (Ci -Cg) alkoxy- (Ci-Cg) -haloalkyl, aryl, aryl- (Ci-Cg) -alkyl, heteroaryl, heteroaryl- (Ci-Cg) -alkyl, (C 3 -Cio) cycloalkyl- (Ci- Cg) alkyl, (C 4 -Cio) cycloalkenyl (Ci-Cg) alkyl, (Ci-Cg) alkoxycarbonyl- (Ci-Cg) alkyl, (C 2 - Cg) alkenyloxycarbonyl- (Ci Cg) -alkyl, aryl- (Ci-Cg) -alkoxycarbonyl- (Ci-Cg) -alkyl, hydroxycarbonyl- (Ci-Cg) -alkyl, heterocyclyl or heterocyclyl- (Ci-Cg) -alkyl,
R16 für (Ci-Cg)-Alkyl, (C2-Cg)-Alkenyl, (C2-Cg)-Alkinyl, (Ci-Cg)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-Cg)-Haloalkenyl, (C2-Cg)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C4-C10)- Cycloalkenyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-haloalkyl, Aryl, Aryl-(Ci-Cg)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cg)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl-(Ci-Cg)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-Cg)-alkyl steht, und wobei die cyclischen Strukturelemente, insbesondere die Strukturelemente Aryl, R 16 represents (Ci-Cg) alkyl, (C 2 -Cg) alkenyl, (C 2 -Cg) alkynyl, (Ci-Cg) cyanoalkyl, (C 1 -C 10 ) haloalkyl, (C 2 -Cg) haloalkenyl, (C 2 -Cg) haloalkynyl, (C 3 -Cio) cycloalkyl, (C 4 -C 10 ) cycloalkenyl, (Ci-Cg) alkoxy- (Ci-Cg) alkyl, (Ci-Cg) alkoxy- (Ci-Cg) haloalkyl, aryl, Aryl- (Ci-Cg) -alkyl, heteroaryl, heteroaryl- (Ci-Cg) -alkyl, heterocyclyl- (Ci-C8) -alkyl, (C3-Cio) -cycloalkyl- (Ci-Cg) -alkyl, (C4 -Cio) -Cycloalkenyl- (Ci-Cg) -alkyl, and wherein the cyclic structural elements, in particular the structural elements aryl,
Cycloalkyl, Cycloalkenyl, Heteroaryl und Heterocyclyl, der jeweils in R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12 R13, R14, R15 und R16 genannten Reste unsubstituiert sind oder durch einen oder mehrere Reste, ausgewählt aus der Gruppe bestehend aus Halogen, Nitro, Hydroxy, Cyano, NR13R14, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, (Ci-C4)- Alkylthio, (Ci-C4)-Alkylsulfoxy, (Ci-C4)-Alkylsulfon, (Ci-C4)-Haloalkylthio, (Ci-C4)- Haloalkylsulfoxy, (Ci-C4)-Haloalkylsulfon, (Ci-C4)-Alkoxy-carbonyl, (Ci-C4)-Haloalkoxy- carbonyl, (Ci-C4)-Alkylcarboxy, (Cs-Cej-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C4)- Alkoxy-carbonyl-(Ci-C4)-alkyl, Hydroxycarbonyl, Hydroxycarbonyl-(Ci-C4)-alkyl, R13R14N- carbonyl, und wobei die Strukturelemente Cycloalkyl bzw. Heterocyclyl n Oxogruppen aufweisen, wobei n = 0, 1 oder 2 ist, substituiert sind. Cycloalkyl, cycloalkenyl, heteroaryl and heterocyclyl, each of which is in R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 R 13 , R 14 , R 15 and R 16 radicals are unsubstituted or by one or more radicals selected from the group consisting of halogen, nitro, hydroxy, cyano, NR 13 R 14 , (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, (Ci-C 4 ) -alkylthio, (Ci-C 4 ) -alkylsulfoxy, (Ci-C 4 ) -alkylsulfone, (Ci-C 4 ) haloalkylthio, (Ci-C 4 ) haloalkylsulfoxy, (Ci-C 4 ) haloalkylsulfone, (Ci-C 4 ) alkoxycarbonyl, (Ci-C 4 ) haloalkoxycarbonyl, ( Ci-C 4 ) alkylcarboxy, (Cs-Cej-cycloalkyl, (C3-C6) -cycloalkyl- (Ci-C6) -alkyl, (Ci-C 4 ) -alkoxy-carbonyl- (Ci-C 4 ) -alkyl , Hydroxycarbonyl, Hydroxycarbonyl- (Ci-C 4 ) alkyl, R 13 R 14 N-carbonyl, and wherein the structural elements cycloalkyl or heterocyclyl n oxo groups, where n = 0, 1 or 2, are substituted.
2. Verbindung der allgemeinen Formel (I) gemäß Anspruch lund/oder deren Salze, dadurch 2. A compound of general formula (I) according to claim 1 and / or its salts, thereby
gekennzeichnet, dass  characterized that
Q für die Gruppe Q for the group
Figure imgf000161_0001
Figure imgf000161_0001
Q-1 Q-2 steht Q-1 Q-2 stands
A unabhängig voneinander für O (Sauerstoff), oder die Gruppierung NR10 oder C-RUR12 stehen, wobei R10, R11 und R12 in den Gruppierungen NR10 oder C-RUR12 jeweils gleiche oder verschiedene Bedeutungen gemäß der unten stehenden Definition haben, A independently of one another represents O (oxygen), or the grouping NR 10 or CR U R 12 , where R 10 , R 11 and R 12 in the groupings NR 10 or CR U R 12 each have the same or different meanings according to the definition below to have,
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, R1 für Halogen, Cyano, (Ci-Cv)-Alkyl, (Ci-C7)-Haloalkyl, (Ci-C7)-Hydroxyalkyl, (C1-C7)- Alkoxyalkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Haloalkoxy, (Ci-C7)-Alkylthio, (C1-C7)- Haloalkylthio, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor- Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl,X stands for the grouping CR 1 , if Y stands for CH, R 1 for halogen, cyano, (Ci-Cv) alkyl, (Ci-C7) haloalkyl, (Ci-C7) hydroxyalkyl, (C1-C7) alkoxyalkyl, (Ci-C7) alkoxy, (Ci C7) haloalkoxy, (Ci-C7) alkylthio, (C1-C7) haloalkylthio, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2 , 5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl,
3.5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3- Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor- Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor- Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2- Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5- Fluor-Phenyl, 3-Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom- Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3- Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5- Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor- Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl- Phenyl, 2,4-Dimethyl-Phenyl,3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichloro- Phenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichloro- Phenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodo- Phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chloro-phenyl, 3- Bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3- Chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2- Fluorine-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl,
2.5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl- Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6- Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4- Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy- Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl,2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3, 4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy- Phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl,
3.4.5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3- Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3- Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3- Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3- Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor- Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor- Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4- Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3 -Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)-alkyl, (C3-C7)-Halocycloalkyl, (C3-C7)-Halocycloalkyl- (Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl, (C2-C7)-Alkenyl, (C2-C7)-Alkenyloxy, (C2-C7)- Alkinyl steht, R2 für Hydroxy, Hydrothio, Halogen, NR13R14, (Ci-Cv)-Alkoxy, (C3-Cs)-Cycloalkyl- (Ci-Cv)-alkoxy, Aryl-(Ci-Cv)-alkoxy, (Ci-C7)-Alkoxy-(Ci-Cv)-alkoxy, (C1-C7)- Alkylcarbonyloxy, Phenylcarbonyloxy, p-Chlorphenylcarbonyloxy, m- Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p-Fluorphenylcarbonyloxy, m- Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, (C3-C9)- Cycloalkylcarbonyloxy, Heterocyclylcarbonyloxy, (Ci-C7)-Haloalkyl-carbonyloxy, (C2-C7)-Alkenylcarbonyloxy, OC(0)OR15, OC(0)SR16, OC(S)OR15, OC(S)SR16, OSO2R16, OSO2OR15, OCHO steht, 3.4.5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4- Difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl , 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl , 3-methoxy-5-chloro-phenyl, 3-trifluoromethoxy-5-chloro-phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl , 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl , Pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, (C3-C9) cycloalkyl, (C3-C9) cycloalkyl- (Ci C7) alkyl, (C3- C7) halocycloalkyl, (C3-C7) halocycloalkyl- (Ci-C 7 ) alkyl, (Ci-C 7 ) alkylcarbonyl, (C 2 -C 7 ) alkenyl, (C 2 -C 7 ) alkenyloxy , (C 2 -C 7 ) alkynyl, R 2 for hydroxy, hydrothio, halogen, NR 13 R 14 , (Ci-Cv) alkoxy, (C3-Cs) cycloalkyl (Ci-Cv) alkoxy, aryl (Ci-Cv) alkoxy, (Ci -C7) alkoxy- (Ci-Cv) alkoxy, (C1-C7) - alkylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyl (C3-C9) cycloalkylcarbonyloxy, heterocyclylcarbonyloxy, (Ci-C7) haloalkylcarbonyloxy, (C 2 -C 7 ) alkenylcarbonyloxy, OC (0) OR 15 , OC (0) SR 16 , OC (S) OR 15 , OC (S) SR 16 , OSO2R 16 , OSO2OR 15 , OCHO stands,
R3 für Wasserstoff, (Ci-C7)-Alkyl steht, R 3 represents hydrogen, (Ci-C 7 ) alkyl,
R4, R5, R6, R7,R8 und R9 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (C1-C7)- Alkyl, (Ci-C7)-Hydroxyalkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)- Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Phenyl, 2- Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5- Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor- Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor- Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor- Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-lod- Phenyl, 3-lod-Phenyl, 4-lod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3-Brom-5- Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2- Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4- Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3- Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6- Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy- Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy- Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5- Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6- Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4- Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4- Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor- Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5- Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio- Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Benzyl, (C2-Cv)-Alkenyl, (C2-C7)-Alkinyl, Cyano stehen, oder wobei R4, R5, R6, R7,R8 und R9 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen gesättigten oder teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N, O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7-gliedrigen Ring bilden, R 4 , R 5 , R 6 , R 7 , R 8 and R 9 independently of one another for hydrogen, hydroxy, halogen, (C1-C7) - alkyl, (Ci-C 7 ) -hydroxyalkyl, (Ci-C 7 ) - Haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (Ci-C7) alkyl, (Ci-C7) alkoxy, (Ci-C7) alkoxy- (Ci-C7 ) -alkyl, phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2, 3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3 - Chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4- Fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluorophenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromophenyl, 2-chloro-4- bromo-Phe nyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro Phenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chloro Phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl Phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2- Methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3, 4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4- difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2- dIfL uormethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluoro- Phenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chloro Phenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2- Trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridine- 4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl, benzyl, (C2-Cv) alkenyl, (C2-C7) alkynyl, cyano, or where R 4 , R 5 , R 6 , R 7 , R 8 and R 9 together with the carbon atom to which they are each bound, a saturated or partially saturated, optionally interrupted by one to three heteroatoms from the group N, O and S and optionally further substituted , form a total of 3-7-membered ring,
R10 für Wasserstoff, (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)-R 10 for hydrogen, (Ci-C 7 ) alkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 9 ) cycloalkyl, (C3-C9) -
Cycloalkyl-(Ci-C7)-alkyl, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4- Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4- Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2- Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5- Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3-Brom- Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor- Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3- Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4- Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor- Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2- Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6- Chlor-Phenyl, 2-Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl- Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4- Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl- Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy- Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3- Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy- Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3- Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3- Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3- Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor- Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor- Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4- Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3 -Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Benzyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, CHO, C(0)OR15, Cyano-(Ci-C7)-alkyl (Ci-C7)-Alkylcarbonyl steht, Cycloalkyl- (Ci-C7) -alkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6- Difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2- Chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,4-dichloro-phenyl, 2,5-dichloro-phenyl, 2,6-dichloro-phenyl, 2,3-dichloro-phenyl, 3, 4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro-6-chloro r-phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3- Dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy- Phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3- Difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl , 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxy -Phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl -Phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3-yl, tetrahydrofuran-2-yl , Benzyl, (C2-C 7 ) alkenyl, (C 2 -C 7 ) alkynyl, CHO, C (0) OR 15 , cyano- (Ci-C 7 ) alkyl (Ci-C 7 ) alkylcarbonyl .
R11 und R12 unabhängig voneinander für Wasserstoff, Hydroxy, Halogen, (Ci-C7)-Alkyl, R 11 and R 12 independently of one another are hydrogen, hydroxy, halogen, (C 1 -C 7 ) -alkyl,
(Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)- Alkoxy, Phenyl, 2-Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl,(Ci-C 7 ) haloalkyl, (C 3 -C 9 ) cycloalkyl, (C 3 -C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, (Ci-C 7 ) alkoxy, phenyl, 2 -Fluorophenyl, 3 -fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl,
2.5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5- Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3-Chlor- Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl,2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3, 4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl,
3.4.5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom- Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4- Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor- Phenyl, 3-Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3- Fluor-4-Brom-Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4- Fluor-Phenyl, 2-Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor- Phenyl, 3-Fluor-4-Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2- Methyl-Phenyl, 3 -Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5- Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl,3.4.5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodophenyl, 3-iodophenyl, 4- Iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chloro-phenyl, 3-bromo-5- Fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4- Bromophenyl, 2-chloro-4-fluorophenyl, 3-chloro-4-fluorophenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5- Chloro-phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl- Phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl,
3.5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl- Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy- Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4- Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5- Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3- Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3- Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3- Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3- Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3- Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3 -Methyl-5 -Fluor- Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor- Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4- Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluonnethylthio-Phenyl, 3 -Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Benzyl, (C2-Cv)-Alkenyl, (C2-C7)-Alkinyl, Cyano stehen, oder wobei R11 und R12 zusammen mit dem C-Atom, an das sie jeweils gebunden sind, einen teilgesättigten, gegebenenfalls durch ein bis drei Heteroatome aus der Gruppe N,3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4- Methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy- Phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4- Difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5 -Chloro-phenyl, 3-methoxy-5-fluoro-phenyl, 3-methoxy-5-chloro- Phenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2- Trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridine- 4-yl, furan-2-yl, furan-3-yl, benzyl, (C2-Cv) alkenyl, (C2-C7) alkynyl, cyano, or where R 11 and R 12 together with the C atom , to which they are bound, a partially saturated, optionally by one to three, heteroatoms from the group N,
O und S unterbrochenen und gegebenenfalls weiter substituierten, insgesamt 3-7- gliedrigen Ring bilden, O and S form an interrupted and optionally further substituted, total 3-7-membered ring,
R13 und R14 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (C1-C7)- Alkyl, (Ci-C7)-Cyanoalkyl, (Ci-C7)-Haloalkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Phenyl, 2- Fluor-Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5- Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor- Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor- Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor- Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod- Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3-Brom-5- Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2- Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4- Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3- Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6- Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy- Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy- Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5- Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6- Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4- Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4- Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor- Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5- Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio- Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Benzyl, (C3-C9)-Cycloalkyl, (C3-C9)-Cycloalkyl-(Ci-C7)-alkyl, S02R16, (Ci- Cv)-Alkoxycarbonyl, (C2-Cv)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl steht, R 13 and R 14 are the same or different and are independently hydrogen, (C1-C7) alkyl, (Ci-C 7 ) cyanoalkyl, (Ci-C 7 ) haloalkyl, (Ci-C 7 ) alkoxy- (Ci-C 7 ) alkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro -Phenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorine -Phenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4 -Dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3 -Bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3 -Bromo-4-fluoro-phenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2 -Chlor-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chlorine -4-fluoro-phenyl, 2-fluoro-3-chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluorine -5-chlorophenyl, 2-fluoro-6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl , 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl -Phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6 -Dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2nd , 4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl , 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluor methyl) -phenyl, 3-trifluoromethyl-5-fluoro- Phenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chloro Phenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2- Trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridine- 4-yl, furan-2-yl, furan-3-yl, benzyl, (C 3 -C 9 ) cycloalkyl, (C3-C 9 ) cycloalkyl- (Ci-C 7 ) alkyl, S0 2 R 16 , (Ci-Cv) -alkoxycarbonyl, (C2-Cv) -alkenyloxycarbonyl, (C2-C7) -alkynyloxycarbonyl,
R15 für (Ci-Cv)-Alkyl, (Ci-Cv)-Haloalkyl, (C3-C9)-Cycloalkyl, Phenyl, 2-Fluor-Phenyl, 3- Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor- Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor- Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4- Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4- Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl,R 15 for (Ci-Cv) alkyl, (Ci-Cv) haloalkyl, (C3-C 9 ) cycloalkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2, 4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,3-difluoro-phenyl, 3,4-difluoro-phenyl, 3,5-difluoro-phenyl, 2,4, 5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5-trichloro- phenyl,
2.4.6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl,2.4.6-trichlorophenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl,
3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo
4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor- Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3- Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor- Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3-Methyl- Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl- Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5- Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl,4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro 4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro 3- chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro 6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2, 3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl- Phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl,
2.6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy- Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2- Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2- Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2- Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5- Chlor-Phenyl, 3-Methyl-5-Fluor-Phenyl, 3 -Methyl-5 -Chlor-Phenyl, 3-Methoxy-5-Fluor- Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy- Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4- Trifluormethylthio-Phenyl, Benzyl, (C3-C9)-Cycloalkyl-(Ci-Cv)-alkyl steht, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl- Phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorine - phenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorine Phenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, benzyl, (C3-C9) -cycloalkyl- (Ci-Cv) -alkyl,
R16 für (Ci-C7)-Alkyl, (Ci-C7)-Haloalkyl, (C3-C9)-Cycloalkyl, Phenyl, 2-Fluor-Phenyl, 3- Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor- Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor- Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor-Phenyl, 2,4- Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4- Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl,R 16 is for (Ci-C 7 ) alkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 9 ) cycloalkyl, phenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl , 2,4-difluoro-phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,3-difluoro-phenyl, 3,4-difluoro-phenyl, 3,5-difluoro-phenyl, 2 , 4,5-trifluoro-phenyl, 3,4,5-trifluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,4-dichloro-phenyl, 2,5-dichloro -Phenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichlorophenyl, 3,4,5 trichloro-phenyl,
2.4.6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl,2.4.6-trichlorophenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl,
3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluorophenyl, 2-bromo-4-chlorophenyl, 3-bromo
4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3 -Brom-5 -Chlor- Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom-Phenyl, 3- Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor- Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3-Methyl- Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl- Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5- Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl,4-fluorophenyl, 3-bromo-4-chlorophenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chlorophenyl, 2-fluoro-4-bromo-phenyl, 2-chloro 4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro 3- chlorophenyl, 2-fluoro-4-chlorophenyl, 2-fluoro-5-chlorophenyl, 3-fluoro-4-chlorophenyl, 3-fluoro-5-chlorophenyl, 2-fluoro 6-chlorophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,4-dimethylphenyl, 2,5-dimethylphenyl, 2,6-dimethylphenyl, 2, 3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl- Phenyl, 2-methoxyphenyl,
3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl,3-methoxy-phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl,
2.6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy- Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4-Trifluormethoxy-Phenyl, 2- Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4-Difluormethoxy-Phenyl, 2- Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl-Phenyl, 2- Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5- Chlor-Phenyl, 3-Methyl-5-Fluor-Phenyl, 3 -Methyl-5 -Chlor-Phenyl, 3-Methoxy-5-Fluor- Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy- Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl,2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl Phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorine - phenyl, 3-trifluoromethyl-5-chlorophenyl, 3-methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluorophenyl, 3-methoxy-5-chlorine Phenyl, 3-trifluoromethoxy-5-chlorophenyl, 2-ethoxyphenyl, 3-ethoxyphenyl, 4-ethoxyphenyl, 2-methylthio-phenyl, 3-methylthio-phenyl,
4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4- Trifluormethylthio-Phenyl, Benzyl, (C3-C9)-Cycloalkyl-(Ci-Cv)-alkyl steht. 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, benzyl, (C3-C9) -cycloalkyl- (Ci-Cv) -alkyl.
3. Verbindungen der allgemeinen Formel (I) gemäß Anspruch lund/oder deren Salze, dadurch gekennzeichnet, dass X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei 3. Compounds of general formula (I) according to claim 1 and / or their salts, characterized in that X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Fluor, Chlor, Brom, Iod, Cyano, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1- Methylpropyl, 2-Methylpropyl, l,l-Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2- Methylbutyl, 3 -Methylbutyl, l,l-Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2- Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3- Methylpentyl, 4-Methylpentyl, l,l-Dimethylbutyl, 1 ,2-Dimethylbutyl, 1,3-Di- methylbutyl, 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, 1- Ethyl-2-methylpropyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1- Methylcyclopropyl, 2-Methylcyclopropyl, 2,2-Dimethylcyclopropyl, 2,3- Dimethylcyclopropyl, l,l'-Bi(cyclopropyl)-l-yl, l,l'-Bi(cyclopropyl)-2-yl, 2'-Methyl- 1 , 1 '-bi(cyclopropyl)-2-yl, 1 -Cyanocyclopropyl, 2-Cyanocyclopropyl, 1 - Methylcyclobutyl, 2-Methylcyclobutyl, 3-Methylcyclobutyl, 3,3-Dimethylcyclobut-l-yl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 3,3-Difluorcyclobut-l-yl, 3-Fluorcyclobut-l-yl, 2,2-Difluorcycloprop-l-yl, l-Fluorcycloprop-l-yl, 2- Fluorcycloprop-l-yl, 1 -Allylcyclopropyl, 1 -Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1- Ethylcyclopropyl, 1 -Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 1- Methoxycyclohexyl, 2-Methoxycyclohexyl, 3-Methoxycyclohexyl, Trifluormethyl, Pentafluorethyl, l,l,2,2-Tetrafluorethyl, Heptafluorpropyl, Nonafluorbutyl, R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl , 2-methylbutyl, 3-methylbutyl, l, l-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl , l, l-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, 1-ethyl-2-methylpropyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcyclopropyl, 2-methylcyclopropyl, 2,2-dimethylcyclopropyl , 2,3-Dimethylcyclopropyl, l, l'-Bi (cyclopropyl) -l-yl, l, l'-Bi (cyclopropyl) -2-yl, 2'-methyl-1, 1'-bi (cyclopropyl) - 2-yl, 1-cyanocyclopropyl, 2-cyanocyclopropyl, 1 - methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobut-l-yl, 1-cyanocyclobutyl, 2-cyanoc yclobutyl, 3-cyanocyclobutyl, 3,3-difluorocyclobut-l-yl, 3-fluorocyclobut-l-yl, 2,2-difluorocycloprop-l-yl, l-fluorocycloprop-l-yl, 2-fluorocycloprop-l-yl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, trifluoromethyl, pentafluoroethyl, l, 2-tetrafluoroethyl, heptafluoropropyl, nonafluorobutyl,
Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Bromfluormethyl, l-Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2- Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, Chlormethyl, Brommethyl, Hydroxymethyl, Hydroxyethyl, Hydroxy-n-propyl, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, n-Butyloxy, tert-Butyloxy, Methoxymethyl, Ethoxymethyl, n- Propyloxymethyl, iso-Propyloxymethyl, Methoxyethyl, Ethoxyethyl, n-Propyloxyethyl, iso-Propyloxy ethyl, Trifluormethoxy, Difluormethoxy, Pentafluorethoxy, 2, 2,1,1 - Tetrafluorethoxy, 2,2,2-Trifluorethoxy, 2,2-Difluorethoxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, Trifluormethylthio, Pentafluorethylthio, Phenyl, 2-Fluor- Phenyl, 3 -Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6- Difluor-Phenyl, 2,3-Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5- Trifluor-Phenyl, 3,4,5-Trifluor-Phenyl, 2-Chlor-Phenyl, 3 -Chlor-Phenyl, 4-Chlor- Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor-Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor- Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5-Trichlor-Phenyl, 3,4,5-Trichlor- Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3 -Brom-Phenyl, 4-Brom-Phenyl, 2-Iod- Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4-Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3-Brom-5- Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2- Fluor-3 -Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4- Chlor-Phenyl, 3-Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3- Methyl-Phenyl, 4-Methyl-Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6- Dimethyl-Phenyl, 2,3-Dimethyl-Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl-Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy- Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy- Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5- Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy-Phenyl, 2,4,6- Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4- Trifluormethyl-Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4- Difluormethyl-Phenyl, 3,5-Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor- Phenyl, 3-Trifluormethyl-5-Chlor-Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor- Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3-Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5- Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy-Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio- Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2-Trifluormethylthio-Phenyl, 3- Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, Phenyloxy, p-Cl-Phenyloxy, Thiophen-2-yl, Thiophen-3-yl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Furan-2-yl, Furan-3-yl, Tetrahydrofuran-2-yl, Cyclopropylmethyl, Cyclobutylmethyl, Chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, l-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl, hydroxymethyl , Hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, iso-propyloxy ethyl, trifluoromethoxy, difluoromethoxy, pentafluoroethoxy, 2, 2,1,1 - tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, isopropylthio, trifluoromethylthio, pentafluoroethylthio, phenyl 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,4-difluorophenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 2,3-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2,4,5-trifluorophenyl, 3,4,5-trifluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4- Chlorophenyl, 2,4-dichlorophen yl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 2,3-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2,4,5-trichloro- Phenyl, 3,4,5-trichlorophenyl, 2,4,6-trichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-iodine Phenyl, 3-iodophenyl, 4-iodophenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chlorophenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4- Chloro-phenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4- Bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4- Chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3- methyl-phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl Phenyl, 3,5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy- Phenyl, 4-methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3, 5- dimethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-Phe nyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluorophenyl, 3-trifluoromethyl-5-chlorophenyl, 3 -Methyl-5-fluorophenyl, 3-methyl-5-chlorophenyl, 3-methoxy-5-fluoro-phenyl, 3-methoxy-5-chlorophenyl, 3-trifluoromethoxy-5-chlorophenyl, 2 -Ethoxy-phenyl, 3-ethoxy-phenyl, 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio -Phenyl, phenyloxy, p-Cl-phenyloxy, thiophene-2-yl, thiophene-3-yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, furan-2-yl, furan-3 -yl, tetrahydrofuran-2-yl, cyclopropylmethyl, cyclobutylmethyl,
Cyclopentylmethyl, Cyclohexylmethyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, l-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1 -propenyl, 2-Methyl-l -propenyl,Cyclopentylmethyl, cyclohexylmethyl, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,
1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, l-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4- Pentenyl, 1 -Methyl- l-butenyl, 2-Methyl-l -butenyl, 3 -Methyl- l-butenyl, l-Methyl-2- butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3 -butenyl, 2-Methyl-3- butenyl, 3 -Methyl-3 -butenyl, 1 , 1 -Dimethyl-2-propenyl, l,2-Dimethyl-l -propenyl, 1,2- Dimethyl-2-propenyl, l-Ethyl-l -propenyl, 1 -Ethyl-2-propenyl, l-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5-Hexenyl, 1 -Methyl- l-pentenyl, 2-Methyl- l-pentenyl, 3- Methyl- l-pentenyl, 4-Methyl- l-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, l,l-Dimethyl-3- butenyl, 1 ,2-Dimethyl- l-butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3 -butenyl, 1,3- Dimethyl-l-butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3- butenyl, 2,3 -Dimethyl-l-butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3- Dimethyl-l-butenyl, 3,3-Dimethyl-2-butenyl, l-Ethyl-l-butenyl, l-Ethyl-2-butenyl, 1- Ethyl-3-butenyl, 2-Ethyl-l-butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3-butenyl, 1,1,2- Trimethyl-2-propenyl, l-Ethyl-l-methyl-2-propenyl, l-Ethyl-2-methyl-l-propenyl und l-Ethyl-2-methyl-2-propenyl, Prop-2-en-l-yloxy, But-3-en-l-yloxy, Pent-4-en-l-yloxy, Ethinyl, l-Propinyl, 2-Propinyl, l-Butinyl, 2-Butinyl, 3-Butinyl, l-Methyl-2-propinyl,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, l-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-l-pentenyl, 2-methyl-l-pentenyl, 3-methyl-l-pentenyl, 4-methyl-l- 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, l, l-dimethyl-3-butenyl, 1, 2-dimethyl-l-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1, 3 Dimethyl-l-butenyl, l, 3-dimethyl-2-butenyl, l, 3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-l-butenyl, 2,3- Dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, l-ethyl-l-butenyl, l-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- l-methyl-2-propenyl, l-ethyl-2-methyl-l-propenyl and l-ethyl-2-methyl-2-propenyl, prop-2-en-l-yloxy, but-3-en-l- yloxy, pent-4-en-l-yloxy, ethynyl, l-propynyl, 2-propynyl, l-butynyl, 2-butynyl, 3-butynyl, l-methyl-2-propynyl,
1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1 -Methyl-2-butinyl, l-Methyl-3-butinyl,1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, l-methyl-3-butynyl,
2-Methyl-3-butinyl, 3 -Methyl- l-butinyl, 1 , 1 -Dimethyl-2-propinyl, 1 -Ethyl-2-propinyl,2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl,
1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 4-Hexinyl, 5-Hexinyl, 1 -Methyl-2-pentinyl, l-Methyl-1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, l-methyl-
3-pentinyl, 1 -Methyl-4-pentinyl, 2-Methyl-3-pentinyl, 2-Methyl-4-pentinyl, 3 -Methyl- 1- pentinyl, 3-Methyl-4-pentinyl, 4-Methyl- l-pentinyl, 4-Methyl-2-pentinyl, 1 , 1 -Dimethyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-l- pentinyl, 4-methyl-2-pentinyl, 1, 1 -dimethyl-
2-butinyl, l,l-Dimethyl-3-butinyl, l,2-Dimethyl-3-butinyl, 2,2-Dimethyl-3-butinyl, 3,3- Dimethyl- l-butinyl, 1 -Ethyl-2-butinyl, l-Ethyl-3-butinyl, 2-Ethyl-3-butinyl, l-Ethyl-l- methyl-2-propinyl steht, 2-butynyl, l, l-dimethyl-3-butynyl, l, 2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-l-butynyl, 1-ethyl-2- butynyl, l-ethyl-3-butynyl, 2-ethyl-3-butynyl, l-ethyl-l-methyl-2-propynyl,
R2 für Hydroxy, Fluor, Chlor, Brom, Iod, Hydrothio, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 - Methylethylcarbonyloxy, n-Butylcarbonyloxy, 1 -Methylpropylcarbonyloxy, 2- Methylpropylcarbonyloxy, l,l-Dimethylethylcarbonyloxy, n-Pentylcarbonyloxy, 1- Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1,1- Dimethylpropylcarbonyloxy, 1 ,2-Dimethylpropylcarbonyloxy, 2,2- Dimethylpropylcarbonyloxy, 1 -Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1 - Methylpentylcarbonyloxy, 2-Methylpentylcarbonyloxy, 3-Methylpentylcarbonyloxy, 4- Methylpentylcarbonyloxy, l,l-Dimethylbutylcarbonyloxy, 1,2- Dimethylbutylcarbonyloxy, l,3-Di-methylbutylcarbonyloxy, 2,2- Dimethylbutylcarbonyloxy, 2,3-Dimethylbutylcarbonyloxy, 3,3- Dimethylbutylcarbonyloxy, 1 -Ethylbutylcarbonyloxy, 2-Ethylbutylcarbonyloxy, 1,1,2- Trimethylpropylcarbonyloxy, 1 ,2,2-Trimethylpropylcarbonyloxy, 1 -Ethyl- 1 - methylpropylcarbonyloxy, 1 -Ethyl-2-methylpropylcarbonyloxy, Phenylcarbonyloxy, p- Chlorphenylcarbonyloxy, m-Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p- Fluorphenylcarbonyloxy, m-Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n - methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, l, l-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, l, 3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3 Dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1, 2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy, 1-ethyl-2 -methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy,
Cyclopentylcarbonyloxy, Cyclohexylcarbonyloxy, Trifluormethylcarbonyloxy, Difluormethylcarbonyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- Propyloxycarbonyloxy, iso-Propyloxycarbonyloxy, n-Butyloxycarbonyloxy, 1,1- Dimethylethyloxycarbonyloxy, 2,2-Dimethyl-propyloxycarbonyloxy, 2- Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy, Allylcarbonyloxy, Amino, Methylamino, Dimethylamino, Ethylamino, Diethylamino, n-Propylamino, iso- Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Benzylamino steht, Cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethyl-propyloxycarbonyloxy, 2- Methylpropyloxycarbonyloxy, benzyloxycarbonyloxy, allylcarbonyloxy, amino, methylamino, dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, benzylamino,
R3 für Wasserstoff, Methyl, Ethyl steht, und für eine der in der folgenden T abeile spezifisch genannten Gruppierungen Q- 1.1 bis Q- 1.69 steht R 3 represents hydrogen, methyl, ethyl, and represents one of the groups Q-1.1 to Q-1.69 specifically mentioned in the following table
Figure imgf000172_0001
Figure imgf000173_0001
Figure imgf000174_0001
Figure imgf000172_0001
Figure imgf000173_0001
Figure imgf000174_0001
4. Verbindungen der allgemeinen Formel (I) gemäß Anspruch 1 und/oder deren Salze, dadurch gekennzeichnet, dass 4. Compounds of general formula (I) according to claim 1 and / or their salts, characterized in that
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Fluor, Chlor, Brom, lod, Cyano, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1 - Methylpropyl, 2-Methylpropyl, l,l-Dimethylethyl, n-Pentyl, 1 -Methylbutyl, 2- Methylbutyl, 3 -Methylbutyl, l,l-Dimethylpropyl, 1 ,2-Dimethylpropyl, 2,2- Dimethylpropyl, 1 -Ethylpropyl, n-Hexyl, 1 -Methylpentyl, 2-Methylpentyl, 3- Methylpentyl, 4-Methylpentyl, l,l-Dimethylbutyl, 1 ,2-Dimethylbutyl, l,3-Di- methylbutyl, 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, 1- Ethyl-2-methylpropyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, R 1 for fluorine, chlorine, bromine, iodine, cyano, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, l, l-dimethylethyl, n-pentyl, 1-methylbutyl , 2-methylbutyl, 3-methylbutyl, l, l-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl , l, l-dimethylbutyl, 1, 2-dimethylbutyl, l, 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-methyl propyl, 1-ethyl-2-methyl propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,
Trifluormethyl, Pentafluorethyl, l,l,2,2-Tetrafluorethyl, Heptafluorpropyl,  Trifluoromethyl, pentafluoroethyl, l, l, 2,2-tetrafluoroethyl, heptafluoropropyl,
Nonafluorbutyl, Chlor difluormethyl, Bromdifluormethyl, Dichlorfluormethyl, loddifluormethyl, Bromfluormethyl, l-Fluorethyl, 2-Fluorethyl, Fluormethyl,  Nonafluorobutyl, chlorofluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, l-fluoroethyl, 2-fluoroethyl, fluoromethyl,
Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, Chlormethyl, Brommethyl, Hydroxymethyl, Hydroxyethyl, Hydroxy-n-propyl, Methoxy, Ethoxy, n- Propyloxy, iso-Propyloxy, n-Butyloxy, tert-Butyloxy, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, iso-Propyloxymethyl, Methoxyethyl, Ethoxyethyl, n- Propyloxyethyl, iso-Propyloxyethyl, Trifluormethoxy, Difluormethoxy, Pentafluorethoxy, 2,2,l,l-Tetrafluorethoxy, 2,2,2-Trifluorethoxy, 2,2-Difluorethoxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Trifluormethylthio, Pentafluorethylthio, Phenyl, Phenyloxy, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, l-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1 -propenyl, 2-Methyl-l -propenyl, Difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, chloromethyl, bromomethyl, hydroxymethyl, hydroxyethyl, hydroxy-n-propyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n -Butyloxy, tert-butyloxy, methoxymethyl, ethoxymethyl, n-propyloxymethyl, iso-propyloxymethyl, methoxyethyl, ethoxyethyl, n-propyloxyethyl, iso-propyloxyethyl, trifluoromethoxy, difluoromethoxy, pentafluoroethoxy, 2.2, l, l-tetrafluoroethoxy, 2.2 , 2-trifluoroethoxy, 2,2-difluoroethoxy, methylthio, ethylthio, n-propylthio, iso-propylthio, trifluoromethylthio, pentafluoroethylthio, phenyl, phenyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, propenyl, propenyl, ethenyl -Methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl,
1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, l-Pentenyl, 2-Pentenyl, 3-Pentenyl, 4- Pentenyl, 1 -Methyl- l-butenyl, 2-Methyl-l-butenyl, 3 -Methyl- l-butenyl, l-Methyl-2- butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3- butenyl, 3-Methyl-3-butenyl, 1 , 1 -Dimethyl-2-propenyl, l,2-Dimethyl-l-propenyl, 1,2- Dimethyl-2-propenyl, l-Ethyl-l-propenyl, 1 -Ethyl-2-propenyl, Prop-2-en-l-yloxy, But- 3-en-l-yloxy, Pent-4-en-l-yloxy, Ethinyl, l-Propinyl, 2-Propinyl steht, 1-methyl-2-propenyl, 2-methyl-2-propenyl, l-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, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1, 1-dimethyl-2-propenyl, l, 2-dimethyl-l-propenyl, 1,2-dimethyl 2-propenyl, l-ethyl-l-propenyl, 1-ethyl-2-propenyl, prop-2-en-l-yloxy, but-3-en-l-yloxy, pent-4-en-l-yloxy, Ethynyl, l-propynyl, 2-propynyl,
R2 für Hydroxy, Fluor, Chlor, Brom, Iod, Hydrothio, Methoxy, Ethoxy, n-Propyloxy, iso- Propyloxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 - Methylethylcarbonyloxy, n-Butylcarbonyloxy, 1 -Methylpropylcarbonyloxy, 2- Methylpropylcarbonyloxy, l,l-Dimethylethylcarbonyloxy, n-Pentylcarbonyloxy, 1- Methylbutylcarbonyloxy, 2-Methylbutylcarbonyloxy, 3-Methylbutylcarbonyloxy, 1,1- Dimethylpropylcarbonyloxy, 1 ,2-Dimethylpropylcarbonyloxy, 2,2- Dimethylpropylcarbonyloxy, 1 -Ethylpropylcarbonyloxy, n-Hexylcarbonyloxy, 1 - Methylpentylcarbonyloxy, 2-Methylpentylcarbonyloxy, 3-Methylpentylcarbonyloxy, 4- Methylpentylcarbonyloxy, l,l-Dimethylbutylcarbonyloxy, 1,2- Dimethylbutylcarbonyloxy, l,3-Di-methylbutylcarbonyloxy, 2,2- Dimethylbutylcarbonyloxy, 2,3-Dimethylbutylcarbonyloxy, 3,3- Dimethylbutylcarbonyloxy, 1 -Ethylbutylcarbonyloxy, 2-Ethylbutylcarbonyloxy, 1,1,2- Trimethylpropylcarbonyloxy, 1 ,2,2-Trimethylpropylcarbonyloxy, 1 -Ethyl- 1 - methylpropylcarbonyloxy, 1 -Ethyl-2-methylpropylcarbonyloxy, Phenylcarbonyloxy, p- Chlorphenylcarbonyloxy, m-Chlorphenylcarbonyloxy, o-Chlorphenylcarbonyloxy, p- Fluorphenylcarbonyloxy, m-Fluorphenylcarbonyloxy, o-Fluorphenylcarbonyloxy, Benzylcarbonyloxy, Cyclopropylcarbonyloxy, Cyclobutylcarbonyloxy, R 2 for hydroxy, fluorine, chlorine, bromine, iodine, hydrothio, methoxy, ethoxy, n-propyloxy, isopropyloxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 - methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy , l, l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1, 2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n - methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, l, l-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, l, 3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3 Dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1, 2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropylcarbonyloxy, 1-ethyl-2 -methylpropylcarbonyloxy, phenylcarbonyloxy, p-chlorophenylcarbonyloxy, m-chlorophenylcarbonyloxy, o-chlorophenylcarbonyloxy, p-fluorophenylcarbonyloxy, m-fluorophenylcarbonyloxy, o-fluorophenylcarbonyloxy, benzylcarbonyloxy, cyclopropylcarbonyloxy, cyclobutylcarbonyloxy,
Cyclopentylcarbonyloxy, Cyclohexylcarbonyloxy, Trifluormethylcarbonyloxy, Difluormethylcarbonyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, n- Propyloxycarbonyloxy, iso-Propyloxycarbonyloxy, n-Butyloxycarbonyloxy, 1,1- Dimethylethyloxycarbonyloxy, 2,2-Dimethyl-propyloxycarbonyloxy, 2- Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy, Allylcarbonyloxy, Amino, Methylamino, Dimethylamino, Ethylamino, Diethylamino, n-Propylamino, iso- Propylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino,  Cyclopentylcarbonyloxy, cyclohexylcarbonyloxy, trifluoromethylcarbonyloxy, difluoromethylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n-propyloxycarbonyloxy, iso-propyloxycarbonyloxy, n-butyloxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2,2-dimethyl-propyloxyoxyylyloxycarbonyloxy, methylyloxycarbonyloxy, methylyloxycarbonyloxy, methylamyloxycarbonyloxy, methylamyloxycarbonyloxy, methyloxyloxycarbonyloxy, methyloxyloxycarbonyloxy, methyloxyyloxycarbonyloxy, methyloxyyloxycarbonyloxy, 2- methyl Dimethylamino, ethylamino, diethylamino, n-propylamino, isopropylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino,
Cyclohexylamino, Benzylamino steht,  Cyclohexylamino, benzylamino stands,
R3 für Wasserstoff steht, R 3 represents hydrogen,
und Q für eine der in Anspruch 3 spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht. and Q stands for one of the groupings Ql .1 to Ql .69 specifically mentioned in claim 3.
5. Verbindungen der allgemeinen Formel (I) gemäß Anspruch lund/oder deren Salze, dadurch gekennzeichnet, dass 5. Compounds of general formula (I) according to claim 1 and / or their salts, characterized in that
X und Y unabhängig voneinander für C-H oder die Gruppierung C-R1 stehen, wobei X and Y independently of one another represent CH or the grouping CR 1 , where
X für C-H steht, wenn Y für die Gruppierung C-R1 steht und X stands for CH if Y stands for the grouping CR 1 and
X für die Gruppierung C-R1 steht, wenn Y für C-H steht, X stands for the grouping CR 1 , if Y stands for CH,
R1 für Chlor, Brom, Methyl, Ethyl, 1 -Methylethyl, l,l-Dimethylethyl, Trifluormethyl, Methoxy, Ethoxy, Methoxymethyl, Methylthio, Ethylthio, Phenyl steht, R 1 represents chlorine, bromine, methyl, ethyl, 1-methylethyl, l, l-dimethylethyl, trifluoromethyl, methoxy, ethoxy, methoxymethyl, methylthio, ethylthio, phenyl,
R2 für Hydroxy, Methylcarbonyloxy, Ethylcarbonyloxy, n-Propylcarbonyloxy, 1 -R 2 for hydroxy, methylcarbonyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1 -
Methylethylcarbonyloxy, 1 , 1 -Dimethylethylcarbonyloxy, 2-Methylpropylcarbonyloxy, Cyclopropylcarbonyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, 1,1- Dimethylethyloxycarbonyloxy, 2-Methylpropyloxycarbonyloxy, Benzyloxycarbonyloxy steht, Methylethylcarbonyloxy, 1, 1-dimethylethylcarbonyloxy, 2-methylpropylcarbonyloxy, cyclopropylcarbonyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, 1,1-dimethylethyloxycarbonyloxy, 2-methylpropyloxycarbonyloxy, benzyloxycarbonyloxy,
R3 für Wasserstoff steht, R 3 represents hydrogen,
Q für eine der in Anpruch 3 spezifisch genannten Gruppierungen Q-l .1 bis Q-l .69 steht. Q stands for one of the groupings Q-1 .1 to Q-1 .69 specifically mentioned in Claim 3.
6. Verwendung einer oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salzen wie in einem der Ansprüche 1 bis 5 definiert, als Herbizid und/oder 6. Use of one or more compounds of general formula (I) and / or their salts as defined in one of claims 1 to 5, as a herbicide and / or
Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen.  Plant growth regulator, preferably in crops of useful and / or ornamental plants.
7. Herbizides und/oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass das Mittel eine oder mehrere Verbindungen der Formel (I) und/oder deren Salze enthält wie in einem der Ansprüche 1 bis 5 definiert, und ein oder mehrere weitere Stoffe ausgewählt aus den Gruppen (i) und/oder (ii), mit 7. Herbicidal and / or plant growth regulating agent, characterized in that the agent contains one or more compounds of the formula (I) and / or their salts as defined in one of claims 1 to 5, and one or more further substances selected from the groups (i) and / or (ii), with
(i) ein oder mehrere weitere agrochemisch wirksame Stoffe, vorzugsweise ausgewählt aus der Gruppe bestehend aus Insektiziden, Akariziden, Nematiziden, weiteren Herbiziden, Fungiziden, Safenern, Düngemitteln und/oder weiteren Wachstumsregulatoren, (i) one or more further agrochemically active substances, preferably selected from the group consisting of insecticides, acaricides, nematicides, further herbicides, fungicides, safeners, fertilizers and / or further growth regulators,
(ii) ein oder mehrere im Pflanzenschutz übliche Formulierungshilfsmittel. (ii) one or more formulation auxiliaries customary in crop protection.
8. Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen, dadurch gekennzeichnet, dass eine wirksame Menge 8. A method for controlling harmful plants or for regulating the growth of plants, characterized in that an effective amount
einer oder mehrerer Verbindungen der Formel (I) und/oder deren Salzen, wie in einem der Ansprüche 1 bis 5 definiert, oder  one or more compounds of formula (I) and / or their salts as defined in any one of claims 1 to 5, or
eines Mittels nach Anspruch 7,  an agent according to claim 7,
auf die Pflanzen, Pflanzensamen, den Boden, in dem oder auf dem die Pflanzen wachsen, oder die Anbaufläche appliziert wird.  on the plants, plant seeds, the soil in or on which the plants grow, or the cultivated area is applied.
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Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016071359A1 (en) * 2014-11-07 2016-05-12 Syngenta Participations Ag Herbicidal compounds
WO2016071360A1 (en) * 2014-11-07 2016-05-12 Syngenta Participations Ag Herbicidal pyrrolone derivatives
WO2018029104A1 (en) * 2016-08-11 2018-02-15 Bayer Cropscience Aktiengesellschaft Substituted pyrazolinyl derivates, method for the production thereof and use thereof as herbicides and/or plant growth regulators

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2016071359A1 (en) * 2014-11-07 2016-05-12 Syngenta Participations Ag Herbicidal compounds
WO2016071360A1 (en) * 2014-11-07 2016-05-12 Syngenta Participations Ag Herbicidal pyrrolone derivatives
WO2018029104A1 (en) * 2016-08-11 2018-02-15 Bayer Cropscience Aktiengesellschaft Substituted pyrazolinyl derivates, method for the production thereof and use thereof as herbicides and/or plant growth regulators

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