WO2020064260A1 - Substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides and salts thereof and their use as herbicidal active substances - Google Patents

Substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides and salts thereof and their use as herbicidal active substances Download PDF

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WO2020064260A1
WO2020064260A1 PCT/EP2019/073090 EP2019073090W WO2020064260A1 WO 2020064260 A1 WO2020064260 A1 WO 2020064260A1 EP 2019073090 W EP2019073090 W EP 2019073090W WO 2020064260 A1 WO2020064260 A1 WO 2020064260A1
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alkyl
ring
aryl
optionally substituted
compounds
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PCT/EP2019/073090
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German (de)
French (fr)
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Uwe Döller
Hendrik Helmke
Stefan Lehr
Michael Charles MCLEOD
Thomas Müller
Olaf Peters
Anu Bheemaiah MACHETTIRA
Dirk Schmutzler
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Bayer Aktiengesellschaft
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings

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 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides 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.
  • WO2016 / 182780 describes certain substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides as intermediates in the synthesis of aryl-substituted bicyclic compounds with herbicidal properties.
  • WO2015 / 084796 describes certain substituted 2-oxo-N, 4-diphenylpyrrolidine-3-carboxamides and N, 4-diphenyl-2-sulfanylidene-pyrrolidine-3-carboxamides with herbicidal properties, the underlying central ring system always being a lactam or thiolactam group
  • substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts as herbicidal active ingredients has not yet been described.
  • selected substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts are particularly suitable as herbicidal active compounds as herbicides.
  • the present invention relates to the use of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (1) or their salts as herbicidal active ingredients
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci-C 8) alkyl, (C 3- C 8) cycloalkyl, (C 2 -C 8) -alkenyl, (C 2 - C 8 ) -alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) - Halocycloalkyl
  • the compounds of general formula (1) can be added by adding a suitable one
  • inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , ftPO i 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, for example, p-toluenesulfonic acid, form salts to a basic group, such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents determined in deprotonated form, such as sulfonic acids
  • Sulphonic acid amides or carboxylic acids can form internal salts with protonatable groups such as amino groups. Salt formation can also be caused by exposure to a base
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or
  • Potassium hydroxide, sodium and potassium carbonate and sodium and potassium hydrogen carbonate 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 ammonium salts, for example with cations of the formula
  • R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl.
  • Alkylsulfoxonium salts such as (Ci-C ij-trialkylsulfonium and (Ci-C ij-trialkylsulfoxonium salts.
  • substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) to be used according to the invention can be present in various tautomeric structures depending on external conditions, such as pH, solvent and temperature all of which are intended to be encompassed by the general formula (I).
  • a preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, Alkyl, (C 3 -Cvj-cycloalkyl, (C 2 -Cv) alkenyl, (C 2 -Cv) alkynyl, aryl, aryl- (Ci-Cv) alkyl, aryl- (C 2 -Cv) alkenyl , Aryl- (C 2 -C 7 ) alkynyl, aryl- (Ci-C 7 ) -alkoxy, heteroaryl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (C 1 -C 7 ) - Hydroxyalkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 7 ) halocycloalkyl, (Ci-C 7 ) alkoxy, (Ci-C 7 )
  • a particularly preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-Cr,) - Hydroxyalkyl, (Ci-C 6 ) haloalkyl, (C3-C6) halocycloalkyl, (Ci-C 6 ) alkoxy, (Ci-C 6 )
  • a very particularly preferred subject of the invention is the use of
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-
  • R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl,
  • Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
  • Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
  • R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl,
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8 ) alkyl, (C3-C 8 ) cycloalkyl, (C2-C 8 ) alkenyl, (C2-C 8 ) -Alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C2-C 8 ) -alkenyl, aryl- (C2-C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C3-C 8 ) -halocycloalkyl, (Ci-C 8
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-Cv) alkyl, (C 3 -Cv) cycloalkyl, (C2-Cv) alkenyl, (C2-Cv) alkynyl, Aryl, aryl- (Ci-Cv) -alkyl, aryl- (C2-Cv) -alkenyl, aryl- (C2-C7) -alkynyl, aryl- (Ci-C7) -alkoxy, heteroaryl, (Ci-C7) - Alkoxy- (Ci-C7) -alkyl, (C1-C7) -hydroxyalkyl, (Ci-C7) -haloalkyl, (C 3 -C7) -halocycloalkyl, (Ci-C7) -alkoxy, (Ci-C7) -haloalkoxy , Aryloxy
  • Particularly preferred subject matter of the invention are compounds of the general formula (I), in which Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • Z represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (GG,) - hydroxyalkyl, (GG) -haloalkyl, (C3-C6) -halocycloalkyl, (GG) -alkoxy, (GG) -haloalkoxy, aryloxy, heteroaryloxy
  • Q represents an optionally substituted aryl, heteroaryl, with each ring or each
  • R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-
  • Particularly preferred subject matter of the invention are compounds of the general formula (I) in which Q is for the groups Q-1.1 to Q-10.14
  • R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
  • Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
  • Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
  • R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
  • 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-methyl 3-
  • heteroarylsulfonyl stands for 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) -, (C i-Cr,) - or (Ci-C i) -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, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio
  • cycloalkylthio means one bonded via a sulfur atom
  • (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 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) -, (C2-C6) - or (C2-C4) -alkenoxy or (C3-C10) -, (C3 -C6) - or (C3-C 4 ) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl 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 alkyl radical in the alkoxycarbonyl group.
  • 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) -, (C2-C6) - or (C2-C 4 ) alkenyloxycarbonyl or (C3-C 10) -, (C3-C6) - or (C3-C4) - alkynyloxycarbonyl.
  • 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.
  • 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, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthoxy, haloalkyl, haloalkyl Cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris- [alkyl] silyl, bis- [alkyl] arylsilyl, bis- [alkyl] alkylsilyl, tris- [alkyl] silylalkyny
  • 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 heteroaromatic and can be unsubstituted or substituted, where the binding site is 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 8-aza-bicyclo [3.2.1] octanyl, 8-aza-bicyclo [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 should be directly adjacent, such as 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 the 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
  • 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, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
  • Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
  • nitrogen heterocycle is partially or fully saturated, it can be linked to the rest of the molecule via carbon as well as nitrogen.
  • 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. Lactones and lactams are thereby preferably also included.
  • the oxo group can also occur on the hetero ring atoms, which can exist in various oxidation states, for example N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 (also 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; 1H-pyrrol-2-yl; lH-pyrrole
  • Carbon atoms are part of another aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multi-fused heteroaromatic.
  • 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-benz
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means for example 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 “Haloalkyl”, “- alkenyl” and “- alkynyl” mean alkyl, alkenyl or alkynyl, for example monohaloalkyl, which is partially or completely substituted by identical or different halogen atoms
  • ( 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, 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 ;
  • 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 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 residues 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.
  • the lower carbon skeletons for example with 1 to 6 C atoms or, in the case of unsaturated groups, with 2 to 6 C atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals.
  • Alkyl radicals also in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, 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
  • 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 e.g.
  • Vinyl which may optionally be substituted by further alkyl radicals, for example (but not limited to) (CAGO-alkyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl , 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -Methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl -3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l, l-dimethyl-2-propenyl, l, 2-dimethyl-l-prop
  • alkynyl also includes straight-chain or branched open-chain ones
  • C2-C6 alkynyl means, for example, 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-penty
  • 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
  • multicyclic 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
  • alkoxyalkyl stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy” means an alkoxyalkyl radical bonded via an oxygen atom, for example (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-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.
  • 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-1-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.
  • trialkylsilyl alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
  • Carbon atoms such as tri - [(Ci-C 8 ) -, (C i-Cr,) - or (Ci-C i) alkyl] silyl, for example (but not limited to) Trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (iso-propyl) silyl, tri- (n-butyl) silyl, tri- (l-methylprop-l-yl) silyl, tri- (2-methylprop -l-yl) silyl, tri (l, l-dimethyleth-l-yl) silyl, tri (2,2-dimethyleth-1-yl) silyl.
  • 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).
  • 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 also be prepared 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 their mixtures.
  • the cleaning can also be carried out by
  • the substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) according to the invention can be prepared starting from known processes.
  • the synthetic routes used and investigated are based on commercially available or easily produced amines, on appropriately substituted aldehydes and on commercially available chemicals such as malonic acid derivatives and nitromethane.
  • the groupings Q, Z, R 1 and R 2 of the general formula (I) have the meanings previously defined in the following schemes, unless exemplary but not restrictive definitions are given.
  • the compounds of the general formula (I) according to the invention are synthesized via an alkylation of an amide of the general formula (II) with an alkylating compound of the general formula (III) in the presence of a base such as, for example, potassium carbonate or
  • the reaction preferably takes place in the temperature range between 0 ° C and 100 ° C, in an adequate solvent such as dichloromethane, acetonitrile, W-dimethylformamide or ethyl acetate (see Scheme 1). Take the amide group and the rest Q.
  • the cis isomer can be detected in small amounts by NMR.
  • the compounds of the general formula (II) are synthesized by aminolysis of an ester of the general formula (IV) with an amine of the general formula (V).
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C (see scheme 2) and can be carried out without solvent by melting. Take the amide group and the rest Q. predominantly the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
  • R ' (Ci-C 4 ) alkyl
  • the compounds of the general formula (IV) are synthesized by reacting the general formula (VI) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • a sulfurization reagent such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 3).
  • the amide group and the rest Q predominantly assume the trans configuration.
  • the cis isomer can be detected in small amounts by NMR.
  • R ' (Ci-C 4 ) alkyl
  • the synthesis of the compound of the general formula (VI) can be prepared by reduction of the compound of the general formula (VII) and subsequent in situ cyclization of the amine intermediate formed by or analogously to methods known to the person skilled in the art (see Scheme 4).
  • the reduction of aliphatic nitro groups by catalytic hydrogenolysis is in the literature
  • Presence of palladium on coal or RaneyNickel, iron or zinc in the acidic medium (see for example reports of the German Chemical Society 1904, 37, 3520-3525), and lithium alanate.
  • the reduction can also be carried out with samarium (II) iodide in the presence of a proton source such as, for example, methanol (see, for example, Tetrahedron Leiters 1991, 32 (14), 1699-1702).
  • a proton source such as, for example, methanol
  • the reduction of the aliphatic nitro group with sodium borohydride can be carried out in the presence of nickel (II) acetate or nickel (II) chloride (see, for example, Tetrahedron Leiters 1985, 26 (52), 6413-6416).
  • R ' (Ci-C 4 ) alkyl
  • the base may be an alkanolate salt of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol.
  • the reaction can be carried out with bases such as lithium hexamethyldisilazane,
  • R ' (Ci-C 4 ) alkyl
  • the compounds of general formula (VIII) can be prepared by Knoevenagel condensation of an aldehyde of general formula (XI) and malonic esters of general formula (XII) (see Scheme 6; G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
  • R ' (Ci-C 4 ) alkyl
  • Scheme 7 describes the synthesis of the compound of the general formula (VII) by reacting a malonic ester of the general formula (XII) with a nitroolefin of the general formula (XIII) in the presence of a base.
  • the base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol, or bases such as lithium hexamethyldisilazane,
  • R ' (Ci-C 4 ) alkyl
  • the compounds of the general formula (XIII) can be prepared by condensing an aldehyde of the general formula (XI) and compounds of the general formula (IX) in the presence of a base such as sodium hydride in an adequate solvent such as tetrahydrofuran (see Scheme 8 ).
  • the compounds of the general formula (II) are synthesized by reacting the general formula (XV) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • a sulfurization reagent such as, for example, phosphorus pentasulfide or Lawesson's reagent.
  • the reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 9).
  • the amide group and the rest Q predominantly assume the trans configuration.
  • the cis isomer can be detected in small amounts by NMR.
  • the compound of the general formula (XIV) can also be formed in the reaction.
  • the compounds of the general formula (XV) are synthesized via an amide coupling of an acid of the general formula (XVI) with an amine of the general formula (V) in the presence of an amide coupling reagent such as, for example, T3P, dicyclohexylcarbodiimide, N- (3-dimcthylaminopropyl) - / ⁇ "- cthylcarbodiimide, / V,, VC abony 1 diimid azo 1, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthsis, Ed. N.
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction takes place preferably in the temperature range between 0 ° C.
  • the synthesis of the acid of the general formula (XVI) can be prepared by saponification of the compound of the general formula (VI) according to or analogously to methods known to the skilled worker (Scheme 11).
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base can be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium) and the saponification reaction preferably takes place in the temperature range between room temperature and 100 ° C.
  • the Lewis acid can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (Ci-C 4 ) alkyl
  • Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction.
  • the reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile,, V,, V- D imct hy 1 - for ma mid or ethyl acetate and in the presence of a base such as triethylamine, / V,, V- D iisop ro py 1 c t h y 1 a m i n or l, 8-diazabicyclo [5.4.0] undec-7-cen instead (see Scheme 12).
  • T3P peptide coupling conditions see Organic Process Research & Development 2009, 13, 900-906.
  • the amide group and the rest Q predominantly assume the trans configuration. In some cases, the
  • the synthesis of the acid of the general formula (XVII) can be prepared by saponification of the compound of the general formula (XVIII) according to or analogously to methods known to the person skilled in the art (Scheme 13).
  • the saponification can be carried out in the presence of a base or a Lewis acid.
  • the base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium) and the saponification reaction preferably takes place in the temperature range between
  • the Lewis acid can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
  • R ' (Ci-C 4 ) alkyl
  • R ' (Ci-C 4 ) alkyl
  • reaction mixture was stirred at room temperature overnight and then sat.
  • Ammonium chloride solution (20ml) and ethyl acetate (20ml) added and stirred for a further hour at room temperature.
  • the insoluble constituents were filtered off over Celite and the phases were subsequently separated.
  • the aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with sat.
  • Ammonium chloride solution and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
  • the resulting crude product was dissolved in ethanol (40 ml) and a solution of sodium hydroxide (1.12 g, 27.8 mmol, 3.0 equiv) in water (40 ml) was added.
  • the resulting reaction mixture was stirred at room temperature overnight and then water (50 ml) and diethyl ether (50 ml) were added.
  • the organic phase was discarded and the aqueous phase with conc. HCl adjusted to pH 2.
  • the aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated.
  • Table 1.1 Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.1-1 to 1.1-247 of table 1.1 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1.
  • Table 1.2 Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.2-1 to 1.2-247 of table 1.2 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.3 Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.3-1 to 1.3-247 of table 1.3 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1.
  • Table 1.4 Preferred compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.4-1 to 1.4-247 of table 1.4 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
  • Table 1.5 Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.5-1 to 1.5-247 of table 1.5 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.6 Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.6-1 to 1.6-247 of table 1.6 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.7 Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.7-1 to 1.7-247 of table 1.7 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.8 Preferred compounds of the formula (1.8) are the compounds 1.8-1 to 1.8-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.8-1 to 1.8-247 in Table 1.8 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.9 Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.9-1 to 1.9-247 of table 1.9 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
  • Table 1.10 Preferred compounds of the formula (1.10) are the compounds 1.10-1 to 1.10-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.10-1 to 1.10-247 of table 1.10 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.11 Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.11-1 to 1.11-247 of table 1.11 are thus by the meaning of the respective entries No. 1 to
  • Table 1.12 Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.12-1 to 1.12-247 of table 1.12 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.13 Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.13-1 to 1.13-247 of table 1.13 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.14 Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.14-1 to 1.14-247 of table 1.14 are thus by the meaning of the respective entries No. 1 to
  • Table 1.15 Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.15-1 to 1.15-247 of table 1.15 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.16 Preferred compounds of the formula (1.16) are the compounds 1.16-1 to 1.16-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.16-1 to 1.16-247 of table 1.16 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.17 Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.17-1 to 1.17-247 of table 1.17 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.18 Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.18-1 to 1.18-247 of table 1.18 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.19 Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.19-1 to 1.19-247 of table 1.19 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.20 Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.20-1 to 1.20-247 of table 1.20 are thus by the meaning of the respective entries No. 1 to
  • Table 1.21 Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.21-1 to 1.21-247 of table 1.21 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-247, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.23 Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-247, in which Q has the meanings of Table 1 given in the respective row.
  • Table 1.24 Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.25 Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.25-1 to 1.25-247 of table 1.25 are thus by the meaning of the respective entries No. 1 to
  • Table 1.26 Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.26-1 to 1.26-247 of table 1.26 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.27 Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.27-1 to 1.27-247 of table 1.27 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.28 Preferred compounds of the formula (1.28) are the compounds 1.28-1 to 1.28-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.28-1 to 1.28-247 of table 1.28 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.29 Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.29-1 to 1.29-247 of table 1.29 are thus by the meaning of the respective entries No. 1 to
  • Table 1.30 Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.30-1 to 1.30-247 of table 1.30 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.31 Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.31-1 to 1.31-247 of table 1.31 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.32 Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.32-1 to 1.32-247 of table 1.32 are thus by the meaning of the respective entries No. 1 to
  • Table 1.33 Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.33-1 to 1.33-247 of table 1.33 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.34 Preferred compounds of the formula (1.34) are the compounds 1.34-1 to 1.34-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.34-1 to 1.34-247 of table 1.34 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.35 Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.35-1 to 1.35-247 in table 1.35 are thus by the meaning of the respective entries No. 1 to
  • Table 1.36 Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.36-1 to 1.36-247 of table 1.36 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.37 Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.37-1 to 1.37-247 of table 1.37 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.38 Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.38-1 to 1.38-247 of table 1.38 are thus by the meaning of the respective entries No. 1 to
  • Table 1.39 Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.39-1 to 1.39-247 of table 1.39 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.40 Preferred compounds of the formula (1.40) are the compounds 1.40-1 to 1.40-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.40-1 to 1.40-247 of table 1.40 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.41 Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.41-1 to 1.41-247 of table 1.41 are thus by the meaning of the respective entries No. 1 to
  • Table 1.42 Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.42-1 to 1.42-247 in table 1.42 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.43 Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.43-1 to 1.43-247 of table 1.43 are thus by the meaning of the respective entries No. 1 to
  • Table 1.44 Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.44-1 to 1.44-247 of table 1.44 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.45 Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.45-1 to 1.45-247 in table 1.45 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.46 Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.46-1 to 1.46-247 in table 1.46 are thus by the meaning of the respective entries No. 1 to
  • Table 1.47 Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.47-1 to 1.47-247 of table 1.47 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.48 Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.48-1 to 1.48-247 of table 1.48 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.49 Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.49-1 to 1.49-247 of table 1.49 are thus by the meaning of the respective entries No. 1 to
  • Table 1.50 Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.50-1 to 1.50-247 of table 1.50 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.51 Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.51-1 to 1.51-247 of table 1.51 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.52 Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.52-1 to 1.52-247 of table 1.52 are thus by the meaning of the respective entries No. 1 to
  • Table 1.53 Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.53-1 to 1.53-247 of table 1.53 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.54 Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.54-1 to 1.54-247 of table 1.54 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.55 Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.55-1 to 1.55-247 of table 1.55 are thus by the meaning of the respective entries No. 1 to
  • Table 1.56 Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.56-1 to 1.56-247 of table 1.56 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.57 Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.57-1 to 1.57-247 of table 1.57 are thus by the meaning of the respective entries No. 1 to
  • Table 1.58 Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.58-1 to 1.58-247 of table 1.58 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.59 Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.59-1 to 1.59-247 of table 1.59 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.60 Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.60-1 to 1.60-247 of table 1.60 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.61 Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.61-1 to 1.61-247 of table 1.61 are thus by the meaning of the respective entries No. 1 to
  • Table 1.62 Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.62-1 to 1.62-247 of table 1.62 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.63 Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.63-1 to 1.63-247 of table 1.63 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.64 Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.64-1 to 1.64-247 of table 1.64 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.65 Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.65-1 to 1.65-247 of table 1.65 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.66 Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.66-1 to 1.66-247 of table 1.66 are thus by the meaning of the respective entries No. 1 to
  • Table 1.67 Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.67-1 to 1.67-247 of table 1.67 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.68 Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.68-1 to 1.68-247 of table 1.68 are thus by the meaning of the respective entries No. 1 to
  • Table 1.69 Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.69-1 to 1.69-247 of table 1.69 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.70 Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.70-1 to 1.70-247 of table 1.70 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.71 Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.71-1 to 1.71-247 of table 1.71 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.72 Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.72-1 to 1.72-247 in table 1.72 are thus by the meaning of the respective entries No. 1 to
  • Table 1.73 Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.73-1 to 1.73-247 of table 1.73 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.74 Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.75 Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-247, in which Q has the meanings of Table 1 given in the respective row. The connections
  • Table 1.76 Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.76-1 to 1.76-247 of table 1.76 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.77 Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.77-1 to 1.77-247 of table 1.77 are thus by the meaning of the respective entries No. 1 to
  • Table 1.78 Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.78-1 to 1.78-247 of table 1.78 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.79 Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.79-1 to 1.79-247 of table 1.79 are thus by the meaning of the respective entries No. 1 to
  • Table 1.80 Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.80-1 to 1.80-247 of table 1.80 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.81 Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.81-1 to 1.81-247 of table 1.81 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • Table 1.82 Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-247, in which Q has the meanings of Table 1 given in the respective row.
  • the connections 1.82-1 to 1.82-247 in table 1.82 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
  • 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 shown in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated from each other by semicolons.
  • the peak list of an example therefore has the form: di (intensity ⁇ ; d2 (intensity2);.; D; (intensity ⁇ ;.; D h (intensity n )
  • 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. With 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
  • the present invention thus relates to the use of one or more 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 (1.82) and / or their salts, each as defined above, as a 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 configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.82) and / or the salts thereof, in each case as defined above, or an agent according to the invention, as defined below, to which (harmful) plants, (harmful) plant seeds, the soil in or on which the (harmful) plants grow, or the cultivated area is applied.
  • an agent according to the invention as defined below
  • the present invention also relates to a method for controlling unwanted plants, preferably in crops, 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 characterized embodiment, in particular one or more compounds of the formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention, as defined below, on undesired plants (for example harmful plants such as mono - or dicotyledonous weeds or unwanted 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 land or non-cultivated land) or the acreage surface (i.e. the area on which the unwanted plants will grow) is applied.
  • undesired plants for example harmful plants such as mono - or dicotyledonous weeds
  • the present invention also relates to methods for combating
  • Regulating the growth of plants preferably 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, preferably in one of the configurations which are characterized as preferred or particularly preferred, in particular one or several compounds of the general formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention as defined below, the plant, the seed of the plant (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 plants grow (e.g. the soil of cultivated or non-cultivated land) or the area under cultivation (ie the area on which the plants will grow) is applied.
  • the seed of the plant 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 plants grow e.g. the soil of cultivated or non-cultivated land
  • the area under cultivation
  • the compounds according to the invention or the agents according to the invention can e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or
  • one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
  • the compounds of general formula (1) and / or their salts according to the invention are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
  • the compounds according to the invention are applied to the surface of the earth prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage approach, but then stop growing and eventually die completely after three to four weeks.
  • Post-emergence treatment stops growing after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain time, so that this is harmful to the crop plants
  • the compounds of the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crops of economically important crops e.g. dicotyledon cultures of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, lpomoea, Lactuca, Linum, Lycopersicon, Miscanthus, Nicotiana, Phaseolus,
  • the compounds according to the invention (depending on their respective structure and the application rate applied) have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate the harvest, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
  • the compounds according to the invention can also be used to control harmful plants in crops of plants which have been modified by genetic engineering or by conventional mutagenesis.
  • the transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • transgenic cultures Preferred with respect to transgenic cultures is the use of the compounds according to the invention and / or their salts in economically important transgenic cultures 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.
  • 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 according to the invention can preferably also be used as herbicides
  • Crop crops are used which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the compounds according to the invention 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 distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
  • Other special properties can include tolerance or resistance to abiotic stressors e.g. There is heat, cold, dryness, salt and ultraviolet radiation.
  • cereals such as wheat, barley, rye, oats, triticale, millet, rice, manioc and maize or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
  • 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.
  • nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
  • 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 gene product mentioned above.
  • 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 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 certain compartment, e.g. the coding region is linked 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). 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.
  • the transgenic plants can be any plants
  • the compounds (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential
  • Plant enzymes e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
  • ALS Inhibit acetolactate synthases
  • EPSP synthases glutamine synthases
  • HPPD hydoxyphenylpyruvate dioxygenases
  • 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, there are often effects 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 which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop is resistant, and influencing the growth and yield of the transgenic crop plants.
  • the invention therefore also relates to the use of the compounds of the general formula (I) and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, if appropriate 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 on 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 applied.
  • 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) customary in crop 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, antifoams, water, organic solvents, preferably at 25 ° C. and 1013 mbar, organic solvents miscible with water in any ratio.
  • formulation auxiliaries customary in crop 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
  • the compounds of the general formula (I) 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 herbicides and Plant growth regulating agents which contain compounds of the general formula (I) and / or their salts.
  • the compounds of general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, 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 ,
  • SC Suspension concentrates
  • CS Capsule suspensions
  • DP dusts
  • pickling agents granules for the litter
  • granules in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
  • Microcapsules and waxes are Microcapsules and waxes.
  • Spray powders are preparations which are uniformly dispersible in water.
  • they contain surfactants of an ionic and / or non-ionic type (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 also contain sodium acid.
  • the herbicidal active ingredients are finely ground, for example in conventional apparatus 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 obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or several surfactants of ionic and / or nonionic type (emulsifiers).
  • organic solvent for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or several surfactants of ionic and / or nonionic type (emulsifiers).
  • emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as
  • Ca-dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters
  • Alkylaryl polyglycol ether fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
  • Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid esters.
  • 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 types of formulation.
  • Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Also suitable ones
  • Active ingredients are 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 preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of compounds of the general formula (I) according to the invention and their salts.
  • 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. Dusty
  • Formulations contain 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.
  • the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating 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 usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity.
  • formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
  • the compounds of the 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.
  • Compounds (I) according to the invention of particular interest which contain the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners.
  • the safeners which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, maize, 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 (I) or their mixtures with further herbicides / pesticides and as
  • the herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water.
  • Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
  • the application rate can vary within wide limits.
  • the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications.
  • compounds of general formula (I) and / or their salts as
  • Plant growth regulator for example as a stalk shortener in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
  • the application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
  • the treatment of the seed which includes the different seed dressing and coating techniques, can also be used.
  • the application rate depends on the individual techniques and can be determined in preliminary tests.
  • agents according to the invention for example mixture formulations or in a tank mix
  • active ingredients which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
  • Protoporphyrinogen oxidase are used, such as those 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, 2012 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 (ISO) or with the chemical name or with the code number are designated.
  • ISO International Organization for Standardization
  • herbicidal mixture partners examples include:
  • flucarbazone flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium, glyphosate, glyph
  • metdicazthiazuron metam, metamifop, metamitron, metazachlor, metazosulfuron,
  • plant growth regulators as possible mix partners are:
  • Sl d compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
  • Fenchlorazole ethyl ester
  • S1-7 2,4-triazole-3-carboxylic acid ethyl ester
  • Sl e compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
  • 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),
  • RA 2 halogen (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m A 1 or 2;
  • VA is 0, 1, 2 or 3;
  • RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
  • RB 3 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl or (Ci-C 4 ) alkoxy and me is 1 or 2, for example those in which
  • RB 1 cyclopropyl
  • RB 2 hydrogen
  • (RB 3 ) 2-OMe
  • RB 1 cyclopropyl
  • R B 1 ethyl
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 5-Cl-2-OMe is (S4-4) and
  • R B 1 isopropyl
  • R B 2 hydrogen
  • (R B 3 ) 2-OMe is (S4-5);
  • Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
  • Rc 3 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, CF 3 and m c 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; m D 1 or 2; RD 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.
  • 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.
  • RD 1 is halogen, (Ci-C i) alkyl, (Ci-C i) haloalkyl, (Ci-C i) alkoxy, (Ci-C4) haloalkoxy,
  • R D 2 is hydrogen or (Ci-C i) alkyl
  • R D 3 is hydrogen, (Ci-CsjAlkyl, (C 2 -C4) alkenyl, (C 2 -C4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy, or their salts, n D is an integer from 0 to 2.
  • S9 active substances from the class of 3- (5-tetrazolylcarbonyl) -2-quinolones (S9), e.g.
  • YE, ZE independently of one another O or S, n ß an integer from 0 to 4,
  • RE 2 (Ci-Ci 6 ) alkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (Ci-C 6 ) alkyl.
  • Sl l active substances of the oxyimino compound type (Sl l), which are known as seed dressings, such as. B.
  • Oxabetrinil ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
  • Fluorofenim (1- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), which is used as a seed dressing -Safeer is known for millet against damage from metolachlor, and
  • Naphthalic anhydride (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
  • Cyanamide known as a safener for corn against damage to imidazolinones
  • 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,
  • Mephenate (4-chlorophenyl methyl carbamate) (S13-9).
  • Active substances which, in addition to a herbicidal action against harmful plants, also have safener action on crop plants such as rice, such as, for. B.
  • COD l-bromo-4- (chloromethylsulfonyl) benzene
  • Kumiai CAS Reg. No. 54091-06-4
  • S15 compounds of the formula (S15) or their tautomers
  • RH 1 represents a (Ci-C 6 ) haloalkyl radical and R H 2 represents hydrogen or halogen and
  • R H 3 , R H 4 independently of one another are hydrogen, (Ci-Ci 6 ) alkyl, (C2-Ci6) alkenyl or
  • (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-C i) haloalkoxy, (Ci C ij alkylthio, (Ci-C ij alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C i) alkoxy] carbonyl, [(Ci-C t j haloalkoxyj-carbonyl, (C3-C6) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl
  • R H 3 is (Ci-C 4 ) alkoxy, (C2-C 4 ) alkenyloxy, (C2-C6) alkynyloxy or (C2-C 4 ) haloalkoxy and R H 4 is hydrogen or (Ci-C 4 ) alkyl or
  • R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
  • heterocyclic ring which, in addition to the N atom, may 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 C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
  • Preferred safeners in combination with the compounds of the formula (I) and / or their salts are: cloquintocet-mexyl, cyprosulfamide, ethyl fenchlorazole, isoxadifene -ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.
  • Biological examples are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl.

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Abstract

The invention relates to substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides of general formula (I) (I) and to the their use as herbicides, in particular for controlling weeds and/or weed grasses in crops of useful plants and/or as plant growth regulators for influencing the growth of crops of useful plants. The present invention further relates to herbicidal and/or plant growth-regulating agents comprising one or more compounds of general formula (I).

Description

Substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide sowie deren Salze und ihre  Substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides and their salts and their
Verwendung als herbizide Wirkstoffe Use as herbicidal active ingredients
Beschreibung 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 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide sowie deren Salze, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide. In particular, this invention relates to substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides 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.
In WO2016/182780 werden bestimmte substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide als Intermediate in der Synthese von Aryl-substituierten bizyklischen Verbindungen mit herbiziden Eigenschaften beschrieben. WO2016 / 182780 describes certain substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides as intermediates in the synthesis of aryl-substituted bicyclic compounds with herbicidal properties.
In WO2015/084796 werden bestimmte substituierte 2-Oxo-N,4-diphenylpyrrolidin-3-carboxamide und N,4-Diphenyl-2-sulfanylidenpyrrolidin-3 -carboxamide mit herbiziden Eigenschaften beschrieben, wobei das zugrundeliegende zentrale Ringsystem stets durch eine Lactam oder Thiolactamgruppe WO2015 / 084796 describes certain substituted 2-oxo-N, 4-diphenylpyrrolidine-3-carboxamides and N, 4-diphenyl-2-sulfanylidene-pyrrolidine-3-carboxamides with herbicidal properties, the underlying central ring system always being a lactam or thiolactam group
gekennzeichnet ist und entsprechend eine exocyclische Doppelbindung aufweist. In WO2016/196593 werden bestimmte substituierte cyclische Amide mit 2-Oxo- bzw. 2 Thio- Substitution mit herbiziden Eigenschaften beschrieben. Auch hier ist das zugrundeliegende zentrale Ringsystem stets durch eine Lactam oder Thiolactamgruppe gekennzeichnet und weist in allen is characterized and accordingly has an exocyclic double bond. WO2016 / 196593 describes certain substituted cyclic amides with 2-oxo or 2 thio substitution with herbicidal properties. Here too, the underlying central ring system is always characterized by a lactam or thiolactam group and points in all
Ausführungen entsprechend eine exocyclische Doppelbindung auf. An exocyclic double bond accordingly.
Die Verwendung von substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamiden oder deren Salze als herbizide Wirkstoffe ist dagegen noch nicht beschrieben. Überraschenderweise wurde nun gefunden, dass ausgewählte substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide oder deren Salze als herbizide Wirkstoffe als Herbizide besonders gut geeignet sind. However, the use of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts as herbicidal active ingredients has not yet been described. Surprisingly, it has now been found that selected substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides or their salts are particularly suitable as herbicidal active compounds as herbicides.
Gegenstand der vorliegenden Erfindung ist die Verwendung von substituierten 5-(Sulfanyl)-3,4-dihydro- 2H-pyrrol-4-carboxamiden der allgemeinen Formel (1) oder deren Salze als herbizide Wirkstoffe The present invention relates to the use of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (1) or their salts as herbicidal active ingredients
Figure imgf000003_0001
Figure imgf000003_0001
worin wherein
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10 membered bicyclic ring system, in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms, which independently of one another to contain 2 O, up to 2 S and up to 5 N atoms, where up to three carbon ring atoms can be selected independently of one another from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from Groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and each ring or ring system optionally with up to 5 substituents is substituted from the group R 2 ,
R1 für (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkynyl steht, R 1 for (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -Cio) cycloalkyl, (C 3 -C 10 ) - cycloalkyl- (Ci-C 8 ) alkyl, (C 3 -C 8 ) halocycloalkyl, (C 3 -C 8 ) halocycloalkyl- (Ci-C 8 ) alkyl, (C 2 -C 8 ) alkenyl, (C 2 -C 8 ) -alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci-C8)-Alkyl, (C3- C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl, Aryl, Aryl-(Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Hydroxyalkyl, (Ci-C8)-Haloalkyl, (C3-C8)-Halocycloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C8)-Cycloalkyloxy, Hydroxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Cyanoalkylaminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (C2-C8)-Alkynylaminocarbonyl, (Ci-C8)-Alkylamino, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, Hydrothio, (Ci-C8)-Bisalkylamino, (C3-C8)-Cycloalkylamino, (Ci-C8)-Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Formylamino, (Ci-C8)-Haloalkylcarbonylamino, (Ci-C8)- Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (Ci-C8)-Dialkyl-aminocarbonylamino, (Ci-C8)-Alkylsulfonylamino, (C3-C8)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci-C 8) alkyl, (C 3- C 8) cycloalkyl, (C 2 -C 8) -alkenyl, (C 2 - C 8 ) -alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) - Halocycloalkyl, (Ci-C 8 ) alkoxy, (Ci-C 8 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 8 ) cycloalkyloxy, hydroxy, (C 3 -C 8 ) cycloalkyl- (Ci-C 8 ) -alkoxy, (Ci-C 8 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) - cycloalkylaminocarbonyl, (Ci-C 8 ) -cyanoalkylaminocarbonyl, (C 2 - C 8 ) alkenylaminocarbonyl, (C 2 -C 8 ) alkynylaminocarbonyl, (Ci-C 8 ) alkylamino, (Ci-C 8 ) alkylthio, (Ci-C 8 ) haloalkylthio, hydrothio, (Ci-C 8 ) -Bisalkylamino, (C 3 -C 8 ) -cycloalkylamino, (Ci-C 8 ) -alkylcarbonylamino, (C 3 -C 8 ) -cycloalkylcarbonylamino, formylamino, (Ci-C 8 ) -haloalkylcarbonylami no, (Ci-C 8 ) -alkoxycarbonylamino, (Ci-C 8 ) -alkylaminocarbonylamino, (Ci-C 8 ) -dialkyl-aminocarbonylamino, (Ci-C 8 ) -alkylsulfonylamino, (C 3 -C 8 ) -cycloalkylsulfonylamino, Arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C8)-Aminohaloalkylsulfonyl, (Ci-C8)- Alkylaminosulfonyl, (Ci-C8)-Bisalkylaminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)- Alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C8)-Alkylsulfmyl, (C3-C8)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C8)-Dialkylsulfonimidoyl, S-(Ci-C8)-Alkylsulfonimidoyl, (Ci-C8)-Alkylsulfonylaminocarbonyl, (C3-C8)-Cycloalkylsulfonylaminocarbonyl, (C3-C8)- Cycloalkylaminosulfonyl, Aryl-(Ci-C8)-alkylcarbonylamino, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, (Ci-C8)-Hydroxyalkylcarbonylamino, (Ci-C8)-Trialkylsilyl steht. Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 8) -Aminohaloalkylsulfonyl, (Ci-C 8) - alkylaminosulfonyl, (Ci-C 8) -Bisalkylaminosulfonyl, (C 3 -C 8) -Cycloalkylaminosulfonyl, (Ci-C 8) - Haloalkylaminosulfonyl, arylaminosulfonyl, aryl (Ci-C8) -alkylaminosulfonyl, (Ci-C 8) - alkylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 8) -Alkylsulfmyl, (C 3 -C 8) - Cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 8 ) -dialkylsulfonimidoyl, S- (Ci-C 8 ) -alkylsulfonimidoyl, (Ci-C 8 ) -alkylsulfonylaminocarbonyl, (C 3 -C 8 ) -cycloalkylsulfonylaminocarbonyl, ( 3 -C 8 ) -cycloalkylaminosulfonyl, aryl- (Ci-C 8 ) -alkylcarbonylamino, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 8 ) -alkoxy- ( Ci-C 8 ) -alkylcarbonylamino, (Ci-C 8 ) -hydroxyalkylcarbonylamino, (Ci-C 8 ) -trialkylsilyl.
Die Verbindungen der allgemeinen Formel (1) können durch Anlagerung einer geeigneten The compounds of general formula (1) can be added by adding a suitable one
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SO4, ftPO i 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. Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren, bestimmte inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , ftPO i 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, for example, p-toluenesulfonic acid, form salts to a basic group, such as, for example, amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino. These salts then contain the conjugate base of the acid as an anion. Suitable substituents determined in deprotonated form, such as sulfonic acids
Sulfonsäureamide oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salzbildung kann auch durch Einwirkung einer Base auf Sulphonic acid amides or carboxylic acids, can form internal salts with protonatable groups such as amino groups. Salt formation can also be caused by exposure to a base
Verbindungen der allgemeinen Formel (I) erfolgen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin und Pyridin sowie Ammonium-, Alkali- oder Compounds of the general formula (I) take place. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or
Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Alkaline earth metal hydroxides, carbonates and bicarbonates, especially sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der azide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetallsalze oder 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 Ammoniumsalze, zum Beispiel mit Kationen der Formel Alkaline earth metal salts, especially sodium and potassium salts, or also ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula
[NRaRbRcRd]+, worin Ra bis Rd jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Arylalkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und [NR a R b R c R d ] + , wherein R a to R d each independently represent an organic radical, in particular alkyl, aryl, arylalkyl or alkylaryl. Alkylsulfonium and
Alkylsulfoxoniumsalze, wie (Ci-C ij-Trialkylsulfonium- und (Ci-C ij-Trialkylsulfoxoniumsalze. Alkylsulfoxonium salts such as (Ci-C ij-trialkylsulfonium and (Ci-C ij-trialkylsulfoxonium salts.
Die erfindungsgemäß zu verwendenden substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4- carboxamide der allgemeinen Formel (I) können in Abhängigkeit von äußeren Bedingungen, wie pH- Wert, Lösungsmittel und Temperatur in verschiedenen tautomeren Strukturen vorliegen, die alle von der allgemeinen Formel (I) umfasst sein sollen. The substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) to be used according to the invention can be present in various tautomeric structures depending on external conditions, such as pH, solvent and temperature all of which are intended to be encompassed by the general formula (I).
Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. The compounds of the formula (I) used according to the invention and their salts are referred to below as "compounds of the general formula (I)".
Bevorzugter Erfindungsgegenstand ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin A preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-lO-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-lO-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-Cej-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Cyanoalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryl- (Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (C3-C8)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkynyl steht, R 1 for (Ci-Cej-alkyl, (Ci-C 6 ) -haloalkyl, (Ci-C 6 ) -cyanoalkyl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, aryl- (Ci -C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl- (Ci-C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) - cycloalkyl- ( Ci-C 6 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 6 ) -alkyl, (C 2 -C 6 ) - alkenyl, (C 2 -C 6 ) -alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen,
Figure imgf000006_0001
Alkyl, (C3- Cvj-Cycloalkyl, (C2-Cv)-Alkenyl, (C2-Cv)-Alkynyl, Aryl, Aryl-(Ci-Cv)-alkyl, Aryl-(C2-Cv)-alkenyl, Aryl-(C2-C7)-alkinyl, Aryl-(Ci-C7)-alkoxy, Heteroaryl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C1-C7)- Hydroxyalkyl, (Ci-C7)-Haloalkyl, (C3-C7)-Halocycloalkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C7)-Cycloalkyloxy, Hydroxy, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, (Ci-C7)-Cyanoalkylaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C2-C7)-Alkynylaminocarbonyl, (Ci-C7)-Alkylamino, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, Hydrothio, (Ci-C7)-Bisalkylamino, (C3-C7)-Cycloalkylamino, (Ci-C7)-Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Formylamino, (Ci-C7)-Haloalkylcarbonylamino, (C1-C7)- Alkoxycarbonylamino, (Ci-C7)-Alkylaminocarbonylamino, (Ci-C7)-Dialkyl-aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen,
Figure imgf000006_0001
Alkyl, (C 3 -Cvj-cycloalkyl, (C 2 -Cv) alkenyl, (C 2 -Cv) alkynyl, aryl, aryl- (Ci-Cv) alkyl, aryl- (C 2 -Cv) alkenyl , Aryl- (C 2 -C 7 ) alkynyl, aryl- (Ci-C 7 ) -alkoxy, heteroaryl, (Ci-C 7 ) -alkoxy- (Ci-C 7 ) -alkyl, (C 1 -C 7 ) - Hydroxyalkyl, (Ci-C 7 ) haloalkyl, (C 3 -C 7 ) halocycloalkyl, (Ci-C 7 ) alkoxy, (Ci-C 7 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 7 ) -cycloalkyloxy, hydroxy, (C 3 -C 7 ) -cycloalkyl- (Ci-C 7 ) -alkoxy, (Ci-C 7 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 7 ) -alkylaminocarbonyl, (C 3 -C 7 ) cycloalkylaminocarbonyl, (Ci-C 7 ) cyanoalkylaminocarbonyl, (C 2 -C 7 ) alkenylaminocarbonyl, (C 2 -C 7 ) alkynylaminocarbonyl, (Ci-C 7 ) alkylamino, (Ci-C 7 ) alkylthio, (Ci-C 7 ) haloalkylthio, hydrothio, (Ci-C 7 ) bisalkylamino, (C 3 -C 7 ) cycloalkylamino, (Ci-C 7 ) alkylcarbonylamino, (C 3 -C 7 ) -Cycloalkylcarbonylamino, formylamino, (Ci-C 7 ) -haloalkylcarbonylamino, (C 1 -C 7 ) -alkoxycarbonylamino, (Ci-C 7 ) -alkylaminocarbonylamino, (Ci-C 7 ) -dialkyl-aminocar bonylamino, (Ci-C 7 ) alkylsulfonylamino, (C 3 -C 7 ) cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C7)-Aminoalkylsulfonyl, (C1-C7)- Alkylaminosulfonyl, (Ci-C7)-Bisalkylaminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (C1-C7)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (C1-C7)- Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C7)-Alkylsulfinyl, (C3-C7)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C7)-Dialkylsulfonimidoyl, S-(Ci-C7)-Alkylsulfonimidoyl, (Ci-C7)-Alkylsulfonylaminocarbonyl, (C3-C7)-Cycloalkylsulfonylaminocarbonyl, (C3-C7)- Cycloalkylaminosulfonyl, Aryl-(Ci-C7)-alkylcarbonylamino, (C3-C7)-Cycloalkyl-(Ci-Cv)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C7)-Alkoxy-(Ci-C7)-alkylcarbonylamino, (Ci-C7)-Hydroxyalkylcarbonylamino, (Ci-C7)-Trialkylsilyl steht. Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 7 ) aminoalkylsulfonyl, (C 1 -C 7 ) alkylaminosulfonyl, (Ci-C 7 ) bisalkylaminosulfonyl, (C 3 -C 7 ) cycloalkylaminosulfonyl, (C 1 -C 7 ) - Haloalkylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C7) alkylaminosulfonyl, (C 1 -C 7) - alkylsulfonyl, (C 3 -C 7) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 7) alkylsulfinyl, (C 3 - C 7 ) -cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 7 ) -dialkylsulfonimidoyl, S- (Ci-C 7 ) -alkylsulfonimidoyl, (Ci-C 7 ) -alkylsulfonylaminocarbonyl, (C 3 -C 7 ) -cycloalkylsulfonylaminocarbon , (C 3 -C 7 ) - Cycloalkylaminosulfonyl, aryl- (Ci-C7) -alkylcarbonylamino, (C 3 -C 7 ) -cycloalkyl- (Ci-Cv) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C7) -alkoxy- (Ci-C7) -alkylcarbonylamino, (Ci -C7) hydroxyalkylcarbonylamino, (Ci-C7) -trialkylsilyl.
Besonders bevorzugter Erfindungsgegenstand ist die erfindungsgemäßeVerwendung von Verbindungen der allgemeinen Formel (I), worin A particularly preferred subject of the invention is the use according to the invention of compounds of the general formula (I) in which
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Cyanoalkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, Aryl- (Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C4)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C4)-alkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkynyl steht, R 1 for (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -cyanoalkyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, aryl- (Ci-C 4 ) -alkyl, heteroaryl- (Ci-C 4 ) -alkyl, heterocyclyl- (Ci-C 4 ) -alkyl, (C3-C6) -cycloalkyl, (C3-C6) - cycloalkyl- (Ci C 4 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C2-C 4 ) Alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci -Ce)- Alkyl, (C3- C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkynyl, Aryl, Aryl-(Ci-C6)-alkyl, Aryl-(C2-C6)-alkenyl, Aryl-(C2-C6)-alkinyl, Aryl-(Ci-C6)-alkoxy, Heteroaryl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-Cr,)- Hydroxyalkyl, (Ci-C6)-Haloalkyl, (C3-C6)-Halocycloalkyl, (Ci-C6)-Alkoxy, (Ci-C6)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C6)-Cycloalkyloxy, Hydroxy, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (Ci-C6)-Cyanoalkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (C2-C6)-Alkynylaminocarbonyl, (Ci-C6)-Alkylamino, (Ci-C6)-Alkylthio, (Ci-C6)-Haloalkylthio, Hydrothio, (Ci-C6)-Bisalkylamino, (C3-C6)-Cycloalkylamino, (Ci-C6)-Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Formylamino, (Ci-C6)-Haloalkylcarbonylamino, (G-G,)- Alkoxycarbonylamino, (Ci-C6)-Alkylaminocarbonylamino, (Ci-C6)-Dialkyl-aminocarbonylamino, (Ci-C6)-Alkylsulfonylamino, (C3-C6)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 is hydrogen, nitro, amino, cyano, thiocyanato, lsothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (Ci-Cr,) - Hydroxyalkyl, (Ci-C 6 ) haloalkyl, (C3-C6) halocycloalkyl, (Ci-C 6 ) alkoxy, (Ci-C 6 ) haloalkoxy, aryloxy, heteroaryloxy, (C3-C6) cycloalkyloxy, hydroxy , (C3-C6) -cycloalkyl- (Ci-C6) -alkoxy, (Ci-C 6 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 6 ) -alkylaminocarbonyl, (C3-C6) - cycloalkylaminocarbonyl, (Ci- C 6 ) cyanoalkylaminocarbonyl, (C2-C6) alkenylaminocarbonyl, (C2-C6) alkynylaminocarbonyl, (Ci-C 6 ) alkylamino, (Ci-C 6 ) alkylthio, (Ci-C 6 ) haloalkylthio, hydrothio , (Ci-C 6 ) bisalkylamino, (C3-C6) cycloalkylamino, (Ci-C 6 ) alkylcarbonylamino, (C3-C6) cycloalkylcarbonylamino, formylamino, (Ci-C 6 ) haloalkylcarbonylamino, (GG,) Alkoxycarbonylamino, (Ci-C 6 ) -alkylaminocarbonylamino, (Ci-C 6 ) -dialkyl-aminocarbonylamino, (Ci-C 6 ) -alkylsulfonylamino, (C3-C6) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C6)-Aminoalkylsulfonyl, (G-G,)- Alkylaminosulfonyl, (Ci-C6)-Bisalkylaminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (G-G,)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C6)-alkylaminosulfonyl, (G-G,)- Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C6)-Alkylsulfinyl, (C3-C6)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C6)-Dialkylsulfonimidoyl, S-(Ci-C6)-Alkylsulfonimidoyl, (Ci-C6)-Alkylsulfonylaminocarbonyl, (C3-C6)-Cycloalkylsulfonylaminocarbonyl, (C3-C6)- Cycloalkylaminosulfonyl, Aryl-(Ci-C6)-alkylcarbonylamino, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C6)-Alkoxy-(Ci-C6)-alkylcarbonylamino, (Ci-C6)-Hydroxyalkylcarbonylamino, (Ci-C6)-Trialkylsilyl steht. Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 6 ) -aminoalkylsulfonyl, (GG,) - alkylaminosulfonyl, (Ci-C 6 ) -bisalkylaminosulfonyl, (C3-C6) -cycloalkylaminosulfonyl, (GG,) - haloalkylaminosulfonyl, arylaminosulfonyl -C 6 ) -alkylaminosulfonyl, (GG,) - alkylsulfonyl, (C3-C6) -cycloalkylsulfonyl, arylsulfonyl, (Ci-C 6 ) -alkylsulfinyl, (C3-C6) - cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci- C 6) -Dialkylsulfonimidoyl, S- (Ci-C 6) -Alkylsulfonimidoyl, (Ci-C 6) -Alkylsulfonylaminocarbonyl, (C3-C6) -Cycloalkylsulfonylaminocarbonyl, (C3-C6) - Cycloalkylaminosulfonyl, aryl (Ci-C 6) -alkylcarbonylamino, (C 3 -C 6 ) -cycloalkyl- (Ci-C 6 ) - alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkylcarbonylamino, (Ci-C 6 ) -hydroxyalkylcarbonylamino , (Ci-C 6 ) -trialkylsilyl.
Ganz besonders bevorzugter Erfindungsgegenstand ist die erfindungsgemäße Verwendung von A very particularly preferred subject of the invention is the use of
Verbindungen der allgemeinen Formel (I), worin  Compounds of the general formula (I), wherein
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10 membered bicyclic ring system in which each ring or each Ring system consists of carbon atoms and 1-5 heteroatoms, which independently contain up to 2 O, up to 2 S and up to 5 N atoms, with up to three carbon ring atoms independently of one another from groups C (= 0) and C (= S) can be selected, and the sulfur ring atoms can additionally be selected from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) , and wherein each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C3)-Alkyl, (Ci-C3)-Haloalkyl, (Ci-C3)-Cyanoalkyl, (Ci-C3)-Alkoxy-(Ci-C3)-alkyl, Aryl- (Ci-C3)-alkyl, Heteroaryl-(Ci-C3)-alkyl, Heterocyclyl-(Ci-C3)-alkyl, (C3-C6)-Cycloalkyl, (C3-Ce)- Cycloalkyl-(Ci-C3)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C3)-alkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkynyl steht, R 1 for (Ci-C 3 ) alkyl, (Ci-C 3 ) haloalkyl, (Ci-C 3 ) cyanoalkyl, (Ci-C 3 ) alkoxy- (Ci-C 3 ) alkyl, aryl- (Ci-C 3 ) -alkyl, heteroaryl- (Ci-C 3 ) -alkyl, heterocyclyl- (Ci-C 3 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -Ce) - cycloalkyl- (Ci-C 3 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl- (Ci-C 3 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) -alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci-C i)-Alkyl, (C3- Csj-Cycloalkyl, (C2-C i)-Alkenyl, (C2-C4)-Alkynyl, Aryl, Aryl-(Ci-C4)-alkyl, Aryl-(C2-C3)-alkenyl, Aryl-(C2-C3)-alkinyl, Aryl-(Ci-C4)-alkoxy, Heteroaryl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (C1-C4)- Hydroxyalkyl, (Ci-C4)-Haloalkyl, (C3-C5)-Halocycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C5)-Cycloalkyloxy, Hydroxy, (C3-C5)-Cycloalkyl-(Ci-C4)-alkoxy, (Ci-C4)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-Cs)- Cycloalkylaminocarbonyl, (Ci-C4)-Cyanoalkylaminocarbonyl, (C2-C4)-Alkenylaminocarbonyl, (C2-C4)-Alkynylaminocarbonyl, (Ci-C4)-Alkylamino, (Ci-C4)-Alkylthio, (Ci-C4)-Haloalkylthio, Hydrothio, (Ci-C4)-Bisalkylamino, (C3-C5)-Cycloalkylamino, (Ci-C4)-Alkylcarbonylamino, (C3-C5)-Cycloalkylcarbonylamino, Formylamino, (Ci-C4)-Haloalkylcarbonylamino, (C1-C4)- Alkoxycarbonylamino, (Ci-C4)-Alkylaminocarbonylamino, (Ci-C4)-Dialkylaminocabonylamino, (Ci-C4)-Alkylsulfonylamino, (C3-C5)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 5 ) cycloalkyloxy, hydroxy, (C 3 -C 5 ) cycloalkyl- (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 4 ) -alkylaminocarbonyl, (C 3 -Cs) - cycloalkylaminocarbonyl, (Ci-C 4 ) -cyanoalkylaminocarbonyl, (C 2 -C 4 ) -Alkenylaminocarbonyl, (C 2 -C 4 ) -alkynylaminocarbonyl, (Ci-C 4 ) -alkylamino, (Ci-C 4 ) -alkylthio, (Ci-C 4 ) -haloalkylthio, hydrothio, (Ci-C 4 ) - Bisalkylamino, (C 3 -C 5 ) -cycloalkylamino, (Ci-C 4 ) -alkylcarbonylamino, (C 3 -C 5 ) -cycloalkylcarbonylamino, formylamino, (Ci-C 4 ) -haloalkylcarbonylamino, (C 1 -C 4 ) alkoxycarbonylamino, (Ci-C 4 ) alkylaminocarbonylamino, (Ci-C 4 ) dialkylaminocabonylamino, (Ci-C 4 ) alkylsulfonylamino, (C 3 -C 5 ) cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C4)-Aminoalkylsulfonyl, (C1-C4)- Alkylaminosulfonyl, (Ci-C4)-Bisalkylaminosulfonyl, (C3-C5)-Cycloalkylaminosulfonyl, (C1-C4)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C4)-alkylaminosulfonyl, (C1-C4)- Alkylsulfonyl, (C3-C5)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C4)-Alkylsulfinyl, (C3-Cs)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C4)-Dialkylsulfonimidoyl, S-(Ci-C4)-Alkylsulfonimidoyl, (Ci-C4)-Alkylsulfonylaminocarbonyl, (C3-C5)-Cycloalkylsulfonylaminocarbonyl, (C3-Cs)- Cycloalkylaminosulfonyl, Aryl-(Ci-C4)-alkylcarbonylamino, (C3-C5)-Cycloalkyl-(Ci-C4)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C4)-Alkoxy-(Ci-C4)-alkylcarbonylamino, (Ci-C4)-Hydroxyalkylcarbonylamino, (Ci-C4)-Trialkylsilyl steht. Im Speziellen bevorzugter Erfindungsgegenstand ist die erfindungsgemäße Verwendung von Verbindungen der allgemeinen Formel (I), worin Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 4) -Aminoalkylsulfonyl, (C 1 -C 4) - alkylaminosulfonyl, (Ci-C 4) -Bisalkylaminosulfonyl, (C 3 -C 5) -Cycloalkylaminosulfonyl, (C 1 -C 4) - Haloalkylaminosulfonyl, arylaminosulfonyl, aryl (Ci-C4) -alkylaminosulfonyl, (C 1 -C 4) - alkylsulfonyl, (C 3 -C 5) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 4) alkylsulfinyl, (C 3 - Cs) -cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 4 ) -dialkylsulfonimidoyl, S- (Ci-C 4 ) -alkylsulfonimidoyl, (Ci-C 4 ) -alkylsulfonylaminocarbonyl, (C 3 -C 5 ) -cycloalkylsulfonylaminocarbon (C 3 -Cs) cycloalkylaminosulfonyl, aryl- (Ci-C 4 ) -alkylcarbonylamino, (C 3 -C 5 ) -cycloalkyl- (Ci-C 4 ) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkylcarbonylamino, (Ci-C 4 ) -hydroxyalkylcarbonylamino, (Ci-C 4 ) -trialkylsilyl. A particularly preferred subject matter of the invention is the use according to the invention of compounds of the general formula (I) in which
Q für die nachfolgnde genannten Gruppen Q-l . l bis Q-10.14  Q for the following groups Q-1. l to Q-10.14
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
Figure imgf000010_0001
Figure imgf000011_0001
Figure imgf000012_0001
Figure imgf000013_0001
Figure imgf000014_0001
Figure imgf000015_0001
Figure imgf000016_0001
steht,  stands,
Z für die nachfolgend genannten Gruppen Z-l.l bis Z-4.3 Z for the groups Zl to Z-4.3 mentioned below
Figure imgf000017_0001
Figure imgf000018_0001
steht, und R1 für Methyl, Ethyl, n-Propyl, Isopropyl, Cyclopropyl, Cyclopropylmethyl, Benzyl, p-Methoxy- benzyl, 2-Phenethyl, Allyl, Propargyl steht,
Figure imgf000017_0001
Figure imgf000018_0001
stands, and R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl,
Im ganz Speziellen bevorzugter Erfindungsgegenstand ist die Verwendung von Verbindungen der allgemeinen Formel (I), worin The most particularly preferred subject of the invention is the use of compounds of the general formula (I) in which
Q für eine der zuvor spezifisch genannten Gruppen Q- 1.1 bis Q- 10.14 steht, Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
Z für eine der zuvor spezifisch geannten die Gruppen Z-l .1 bis Z-4.3 steht, und Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
R1 für Methyl, Ethyl, Cyclopropylmethyl, Benzyl, 2-Phenethyl, Allyl, Propargyl steht, R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl,
Einige der zuvorgenannten substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide der allgemeinen Formel (I) sind ebenfalls noch nicht im Stand der Technik bekannt. Somit gelten als weiterer Teil der Erfindung substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide der allgemeinen Formel (I) oder deren Salze, Some of the aforementioned substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) are also not yet known in the prior art. Substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) or their salts
Figure imgf000019_0001
wonn
Figure imgf000019_0001
wonn
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, with each ring or ring system optionally with up to 5
Substituenten aus der Gruppe R2 substituiert ist, steht, Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Substituent from the group R 2 is substituted, Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-Cx)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Aryl- (Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkynyl steht, R 1 for (Ci-Cx) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, aryl- ( Ci-C 8 ) -alkyl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C3-Cio) -cycloalkyl, (C3-C10) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 8 ) -alkyl, (C 2 -C 8 ) - alkenyl, (C2-C 8 ) -Alkynyl stands,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, Isothiocyanato, Halogen, (Ci-C8)-Alkyl, (C3- C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl, Aryl, Aryl-(Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Hydroxyalkyl, (Ci-C8)-Haloalkyl, (C3-C8)-Halocycloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C8)-Cycloalkyloxy, Hydroxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Cyanoalkylaminocarbonyl, (C2-C8)-Alkenylaminocarbonyl, (C2-C8)-Alkynylaminocarbonyl, (Ci-C8)-Alkylamino, (Ci-C8)-Alkylthio, (Ci-C8)-Haloalkylthio, Hydrothio, (Ci-C8)-Bisalkylamino, (C3-C8)-Cycloalkylamino, (Ci-C8)-Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Formylamino, (Ci-C8)-Haloalkylcarbonylamino, (Ci-C8)- Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (Ci-C8)-Dialkyl-aminocarbonylamino, (Ci-C8)-Alkylsulfonylamino, (C3-C8)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8 ) alkyl, (C3-C 8 ) cycloalkyl, (C2-C 8 ) alkenyl, (C2-C 8 ) -Alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C2-C 8 ) -alkenyl, aryl- (C2-C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl , (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) - hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C3-C 8 ) -halocycloalkyl, (Ci-C 8 ) -alkoxy, (Ci-C 8 ) -haloalkoxy, aryloxy, heteroaryloxy, (C3-C 8 ) -cycloalkyloxy, hydroxy, (C3-C 8 ) -cycloalkyl- (Ci-C 8 ) -alkoxy, (Ci- C 8 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C3-C 8 ) - cycloalkylaminocarbonyl, (Ci-C 8 ) -cyanoalkylaminocarbonyl, (C2-C 8 ) -alkenylaminocarbonyl, (C2-C 8 ) -alkynylaminocarbonyl, (Ci-C 8 ) -alkylamino, (Ci-C 8 ) -alkylthio, (Ci-C 8 ) -haloalkylthio, hydrothio, (Ci-C 8 ) -bisalkylamino, (C3-C 8 ) - Cycloalkylamino, (Ci-C 8 ) -alkylcarbonylamino, (C3-C 8 ) -cycloalkylcarbonylamino, formylamino, (Ci-C 8 ) -haloalkylcarbonylamino, (Ci-C 8 ) - alkoxycarb onylamino, (Ci-C 8 ) -alkylaminocarbonylamino, (Ci-C 8 ) -dialkyl-aminocarbonylamino, (Ci-C 8 ) -alkylsulfonylamino, (C3-C 8 ) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C8)-Aminohaloalkylsulfonyl, (Ci-C8)- Alkylaminosulfonyl, (Ci-C8)-Bisalkylaminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)- Alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C8)-Alkylsulfmyl, (C3-C8)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C8)-Dialkylsulfonimidoyl, S-(Ci-C8)-Alkylsulfonimidoyl, (Ci-C8)-Alkylsulfonylaminocarbonyl, (C3-C8)-Cycloalkylsulfonylaminocarbonyl, (C3-C8)- Cycloalkylaminosulfonyl, Aryl-(Ci-C8)-alkylcarbonylamino, (C3-C8)-Cycloalkyl-(Ci-C8)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, (Ci-C8)-Hydroxyalkylcarbonylamino, (Ci-C8)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 8) -Aminohaloalkylsulfonyl, (Ci-C 8) - alkylaminosulfonyl, (Ci-C 8) -Bisalkylaminosulfonyl, (C3-C8) -Cycloalkylaminosulfonyl, (Ci-C 8) - Haloalkylaminosulfonyl, arylaminosulfonyl , aryl (Ci-C8) -alkylaminosulfonyl, (Ci-C 8) - alkylsulfonyl, (C3-C8) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 8) -Alkylsulfmyl, (C3-C8) - cycloalkylsulfinyl, Arylsulfinyl, N, S- (Ci-C 8 ) -dialkylsulfonimidoyl, S- (Ci-C 8 ) -alkylsulfonimidoyl, (Ci-C 8 ) -alkylsulfonylaminocarbonyl, (C3-C 8 ) -cycloalkylsulfonylaminocarbonyl, (C3-C 8 ) - Cycloalkylaminosulfonyl, aryl- (Ci-C 8 ) -alkylcarbonylamino, (C3-C 8 ) -cycloalkyl- (Ci-C 8 ) - alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkylcarbonylamino, (Ci-C 8 ) -hydroxyalkylcarbonylamino, (Ci-C 8 ) -trialkylsilyl, with the exception of the following compounds:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8]).  N- (2-Fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8]).
Bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Preferred subject matter of the invention are compounds of general formula (I), wherein
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, R1 für (Ci-C6)-Alkyl, (Ci-C6)-Haloalkyl, (Ci-C6)-Cyanoalkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Aryl- (Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C8)-Cycloalkyl, (CF-Cx)- Cycloalkyl-(Ci-C6)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (Cx-GO-Alkynyl steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 , R 1 for (Ci-C 6 ) alkyl, (Ci-C 6 ) haloalkyl, (Ci-C 6 ) cyanoalkyl, (Ci-C 6 ) alkoxy- (Ci-C 6 ) alkyl, aryl- (Ci-C 6 ) -alkyl, heteroaryl- (Ci-C 6 ) -alkyl, heterocyclyl- (Ci-C 6 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, (CF-Cx) - cycloalkyl- ( Ci-C 6 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 6 ) -alkyl, (C 2 -C 6 ) - alkenyl, (Cx- GO alkynyl stands,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci-Cv)-Alkyl, (C3- Cv)-Cycloalkyl, (C2-Cv)-Alkenyl, (C2-Cv)-Alkynyl, Aryl, Aryl-(Ci-Cv)-alkyl, Aryl-(C2-Cv)-alkenyl, Aryl-(C2-C7)-alkinyl, Aryl-(Ci-C7)-alkoxy, Heteroaryl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C1-C7)- Hydroxyalkyl, (Ci-C7)-Haloalkyl, (C3-C7)-Halocycloalkyl, (Ci-C7)-Alkoxy, (Ci-C7)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C7)-Cycloalkyloxy, Hydroxy, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxy, (Ci-C7)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, (Ci-C7)-Cyanoalkylaminocarbonyl, (C2-C7)-Alkenylaminocarbonyl, (C2-C7)-Alkynylaminocarbonyl, (Ci-C7)-Alkylamino, (Ci-C7)-Alkylthio, (Ci-C7)-Haloalkylthio, Hydrothio, (Ci-C7)-Bisalkylamino, (C3-C7)-Cycloalkylamino, (Ci-C7)-Alkylcarbonylamino, (C3-C7)-Cycloalkylcarbonylamino, Formylamino, (Ci-C7)-Haloalkylcarbonylamino, (C1-C7)- Alkoxycarbonylamino, (Ci-C7)-Alkylaminocarbonylamino, (Ci-C7)-Dialkyl-aminocarbonylamino, (Ci-C7)-Alkylsulfonylamino, (C3-C7)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-Cv) alkyl, (C 3 -Cv) cycloalkyl, (C2-Cv) alkenyl, (C2-Cv) alkynyl, Aryl, aryl- (Ci-Cv) -alkyl, aryl- (C2-Cv) -alkenyl, aryl- (C2-C7) -alkynyl, aryl- (Ci-C7) -alkoxy, heteroaryl, (Ci-C7) - Alkoxy- (Ci-C7) -alkyl, (C1-C7) -hydroxyalkyl, (Ci-C7) -haloalkyl, (C 3 -C7) -halocycloalkyl, (Ci-C7) -alkoxy, (Ci-C7) -haloalkoxy , Aryloxy, heteroaryloxy, (C 3 -C7) cycloalkyloxy, hydroxy, (C 3 -C7) cycloalkyl- (Ci-C7) alkoxy, (Ci-C7) alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C7) -Alkylaminocarbonyl, (C 3 -C7) -cycloalkylaminocarbonyl, (Ci-C7) -cyanoalkylaminocarbonyl, (C2-C7) -alkenylaminocarbonyl, (C2-C7) -alkynylaminocarbonyl, (Ci-C7) -alkylamino, (Ci-C7) - Alkylthio, (Ci-C7) -haloalkylthio, hydrothio, (Ci-C7) bisalkylamino, (C 3 -C7) cycloalkylamino, (Ci-C7) alkylcarbonylamino, (C 3 -C7) cycloalkylcarbonylamino, formylamino, (Ci -C7) haloalkylcarbonylamino, (C1-C7) alkoxycarbonylamino, (Ci-C7) alkylaminocarbonylamino, (Ci-C7) -D ialkyl-aminocarbonylamino, (Ci-C7) -alkylsulfonylamino, (C 3 -C7) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C7)-Aminoalkylsulfonyl, (C1-C7)- Alkylaminosulfonyl, (Ci-C7)-Bisalkylaminosulfonyl, (C3-C7)-Cycloalkylaminosulfonyl, (C1-C7)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C7)-alkylaminosulfonyl, (C1-C7)- Alkylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C7)-Alkylsulfinyl, (C3-C7)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C7)-Dialkylsulfonimidoyl, S-(Ci-C7)-Alkylsulfonimidoyl, (Ci-C7)-Alkylsulfonylaminocarbonyl, (C3-C7)-Cycloalkylsulfonylaminocarbonyl, (C3-C7)- Cycloalkylaminosulfonyl, Aryl-(Ci-C7)-alkylcarbonylamino, (C3-C7)-Cycloalkyl-(Ci-C7)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C7)-Alkoxy-(Ci-C7)-alkylcarbonylamino, (Ci-C7)-Hydroxyalkylcarbonylamino, (Ci-C7)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: Heteroarylsulfonylamino, aminosulfonyl, (Ci-C7) -aminoalkylsulfonyl, (C1-C7) - alkylaminosulfonyl, (Ci-C7) -bisalkylaminosulfonyl, (C 3 -C7) -cycloalkylaminosulfonyl, (C1-C7) - haloalkylaminosulfonyl, arylaminosulfonyl Ci-C7) -alkylaminosulfonyl, (C1-C7) -alkylsulfonyl, (C 3 -C7) -cycloalkylsulfonyl, arylsulfonyl, (Ci-C7) -alkylsulfinyl, (C 3 -C7) - cycloalkylsulfinyl, arylsulfinyl, N, S- ( Ci-C7) -dialkylsulfonimidoyl, S- (Ci-C7) -alkylsulfonimidoyl, (Ci-C7) -alkylsulfonylaminocarbonyl, (C 3 -C7) -cycloalkylsulfonylaminocarbonyl, (C 3 -C7) - cycloalkylaminosulfonyl, aryl- (Ci -alkylcarbonylamino, (C 3 -C7) -cycloalkyl- (Ci-C7) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C7) -alkoxy- (Ci-C7) -alkylcarbonylamino, (Ci-C7) -hydroxyalkylcarbonylamino, (Ci-C7 ) -Trialkylsilyl stands, with the exception of the following compounds:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]). N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]).
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8]).  N- (2-Fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8]).
Besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Particularly preferred subject matter of the invention are compounds of the general formula (I), in which Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können;, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Cyanoalkyl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, Aryl- (Ci-C4)-alkyl, Heteroaryl-(Ci-C4)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, (C3-C6)-Cycloalkyl, (C3-C6)- Cycloalkyl-(Ci-C4)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C4)-alkyl, (C2-C4)- Alkenyl, (C2-C4)-Alkynyl steht, R 1 for (Ci-C 4 ) -alkyl, (Ci-C 4 ) -haloalkyl, (Ci-C 4 ) -cyanoalkyl, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, aryl- (Ci-C 4 ) -alkyl, heteroaryl- (Ci-C 4 ) -alkyl, heterocyclyl- (Ci-C 4 ) -alkyl, (C3-C6) -cycloalkyl, (C3-C6) - cycloalkyl- (Ci C 4 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl (Ci-C 4 ) alkyl, (C 2 -C 4 ) alkenyl, (C2-C 4 ) Alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, Isothiocyanato, Halogen, (Ci -Ce)- Alkyl, (C3- C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkynyl, Aryl, Aryl-(Ci-C6)-alkyl, Aryl-(C2-C6)-alkenyl, Aryl-(C2-C6)-alkinyl, Aryl-(Ci-C6)-alkoxy, Heteroaryl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (G-G,)- Hydroxyalkyl, (G-G)-Haloalkyl, (C3-C6)-Halocycloalkyl, (G-G)-Alkoxy, (G-G)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C6)-Cycloalkyloxy, Hydroxy, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxy, (Ci-Cej-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (G-G)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (Ci-G,)-Cyanoalkylaminocarbonyl, (C2-C6)-Alkenylaminocarbonyl, (C2-C6)-Alkynylaminocarbonyl, (Ci-G,)-Alkylamino, (Ci-G,)-Alkylthio, (Ci-G,)-Haloalkylthio, Hydrothio, (G-G)-Bisalkylamino, (C3-C6)-Cycloalkylamino, (Ci-G,)-Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Formylamino, (Ci-C6)-Haloalkylcarbonylamino, (G-G,)- Alkoxycarbonylamino, (Ci-C6)-Alkylaminocarbonylamino, (Ci-C6)-Dialkyl-aminocarbonylamino, (Ci-C6)-Alkylsulfonylamino, (C3-C6)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 represents hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci -Ce) - alkyl, (C3- C6) cycloalkyl, (C2-C6) alkenyl, (C2-C6) alkynyl, Aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkyl, (GG,) - hydroxyalkyl, (GG) -haloalkyl, (C3-C6) -halocycloalkyl, (GG) -alkoxy, (GG) -haloalkoxy, aryloxy, heteroaryloxy , (C3-C6) -cycloalkyloxy, hydroxy, (C3-C6) -cycloalkyl- (Ci-C6) -alkoxy, (Ci-Cej-alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (GG) -alkylaminocarbonyl, (C3-C6) - Cycloalkylaminocarbonyl, (Ci-G,) - cyanoalkylaminocarbonyl, (C2-C6) -alkenylaminocarbonyl, (C2-C6) -alkynylaminocarbonyl, (Ci-G,) - alkylamino, (Ci-G,) - alkylthio, (Ci-G, ) -Haloalkylthio, hydrothio, (GG) -bisalkylamino, (C3-C6) -cycloalkylamino, (Ci-G,) - alkylcarbonylamino, (C3-C6) -cycloalkylcarbonylamino, formylamino, (Ci-C 6 ) -haloalkylcarbonylamino, (GG,) - alkoxycarbonylamino, (Ci-C 6 ) -alkylaminocarbonylamino, (Ci-C 6 ) -dialkyl-aminocarbonylamino, (Ci-C 6 ) -alkylsulfonylamino, (C3-C6) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C6)-Aminoalkylsulfonyl, (G-G,)- Alkylaminosulfonyl, (Ci-C6)-Bisalkylaminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (G-G,)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(G-C6)-alkylaminosulfonyl, (G-G)- Alkylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Arylsulfonyl, (G-C6)-Alkylsulfinyl, (C3-C6)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C6)-Dialkylsulfonimidoyl, S-(G-C6)-Alkylsulfonimidoyl, (Ci-C6)-Alkylsulfonylaminocarbonyl, (C3-C6)-Cycloalkylsulfonylaminocarbonyl, (C3-C6)- Cycloalkylaminosulfonyl, Aryl-(G-C6)-alkylcarbonylamino, (C3-C6)-Cycloalkyl-(Ci-C6)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C6)-Alkoxy-(Ci-C6)-alkylcarbonylamino, (G-C6)-Hydroxyalkylcarbonylamino, (Ci-C6)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 6 ) -aminoalkylsulfonyl, (GG,) - alkylaminosulfonyl, (Ci-C 6 ) -bisalkylaminosulfonyl, (C3-C6) -cycloalkylaminosulfonyl, (GG,) - haloalkylaminosulfonyl, arylaminosulfonyl 6 ) -alkylaminosulfonyl, (GG) -alkylsulfonyl, (C3-C6) -cycloalkylsulfonyl, arylsulfonyl, (GC 6 ) -alkylsulfinyl, (C3-C6) -cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 6 ) -dialkylsulfonimidoyl , S- (GC 6 ) -alkylsulfonimidoyl, (Ci-C 6 ) -alkylsulfonylaminocarbonyl, (C3-C6) -cycloalkylsulfonylaminocarbonyl, (C3-C6) -cycloalkylaminosulfonyl, aryl- (GC 6 ) -alkylcarbonylamino, (C 3 -C 6 ) -Cycloalkyl- (Ci-C 6 ) - alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 6 ) -alkoxy- (Ci-C 6 ) -alkylcarbonylamino, (GC 6 ) -hydroxyalkylcarbonylamino, (Ci-C 6 ) -trialkylsilyl, except for the following connections:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8])  N- (2-fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8])
Ganz besonders bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Very particularly preferred subject matter of the invention are compounds of the general formula (I), in which
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Q represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 , Z represents an optionally substituted aryl, heteroaryl, with each ring or each
Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C3)-Alkyl, (Ci-C3)-Haloalkyl, (Ci-C3)-Cyanoalkyl, (Ci-C3)-Alkoxy-(Ci-C3)-alkyl, Aryl- (Ci-C3)-alkyl, Heteroaryl-(Ci-C3)-alkyl, Heterocyclyl-(Ci-C3)-alkyl, (C3-C6)-Cycloalkyl, (C3-Ce)- Cycloalkyl-(Ci-C3)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)-Halocycloalkyl-(Ci-C3)-alkyl, (C2-C4)- Alkenyl, (C2-C i)-Alkynyl steht, R 1 for (Ci-C 3 ) alkyl, (Ci-C 3 ) haloalkyl, (Ci-C 3 ) cyanoalkyl, (Ci-C 3 ) alkoxy- (Ci-C 3 ) alkyl, aryl- (Ci-C 3 ) -alkyl, heteroaryl- (Ci-C 3 ) -alkyl, heterocyclyl- (Ci-C 3 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -Ce) - cycloalkyl- (Ci-C 3 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl- (Ci-C 3 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C i) alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, Isothiocyanato, Halogen, (Ci-C i)-Alkyl, (C3- Csj-Cycloalkyl, (C2-C i)-Alkenyl, (C2-C4)-Alkynyl, Aryl, Aryl-(Ci-C4)-alkyl, Aryl-(C2-C3)-alkenyl, Aryl-(C2-C3)-alkinyl, Aryl-(Ci-C4)-alkoxy, Heteroaryl, (Ci-C4)-Alkoxy-(Ci-C4)-alkyl, (C1-C4)- Hydroxyalkyl, (Ci-C4)-Haloalkyl, (C3-C5)-Halocycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C5)-Cycloalkyloxy, Hydroxy, (C3-C5)-Cycloalkyl-(Ci-C4)-alkoxy, (Ci-C i)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-Cs)- Cycloalkylaminocarbonyl, (Ci-C4)-Cyanoalkylaminocarbonyl, (C2-C4)-Alkenylaminocarbonyl, (C2-C4)-Alkynylaminocarbonyl, (Ci-C4)-Alkylamino, (Ci-C i)-Alkylthio, (Ci-C4)-Haloalkylthio, Hydrothio, (Ci-C4)-Bisalkylamino, (C3-C5)-Cycloalkylamino, (Ci-C ij-Alkylcarbonylamino, (C3-C5)-Cycloalkylcarbonylamino, Formylamino, (Ci-C4)-Haloalkylcarbonylamino, (C1-C4)- Alkoxycarbonylamino, (Ci-C4)-Alkylaminocarbonylamino, (Ci-C4)-Dialkylaminocabonylamino, (Ci-C4)-Alkylsulfonylamino, (C3-C5)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C i) alkyl, (C 3 -Csj-cycloalkyl, (C 2 -C i) alkenyl, (C 2 -C 4 ) -Alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) - alkoxy, heteroaryl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, (C 1 -C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 3 -C 5 ) halocycloalkyl , (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 5 ) cycloalkyloxy, hydroxy, (C 3 -C 5 ) cycloalkyl- (Ci-C 4 ) -alkoxy, (Ci-C i) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 4 ) -alkylaminocarbonyl, (C 3 -Cs) - cycloalkylaminocarbonyl, (Ci-C 4 ) -cyanoalkylaminocarbonyl, (C 2 -C 4 ) -Alkenylaminocarbonyl, (C 2 -C 4 ) -alkynylaminocarbonyl, (Ci-C 4 ) -alkylamino, (Ci-C i) -alkylthio, (Ci-C 4 ) -haloalkylthio, hydrothio, (Ci-C 4 ) - Bisalkylamino, (C 3 -C 5 ) cycloalkylamino, (Ci-C ij-alkylcarbonylamino, (C 3 -C 5 ) cycloalkylcarbonylamino, formylamino, (Ci-C 4 ) -haloalkylcarbonylamino, (C 1 -C 4 ) -alkoxycarbonylamino, (Ci-C 4 ) -alkylaminocarbonylamino, (Ci-C 4 ) -dialkylaminocabonylamino, (Ci-C 4 ) -alkylsulfonylamino, (C 3 -C 5 ) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C4)-Aminoalkylsulfonyl, (C1-C4)- Alkylaminosulfonyl, (Ci-C4)-Bisalkylaminosulfonyl, (C3-C5)-Cycloalkylaminosulfonyl, (C1-C4)- Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C4)-alkylaminosulfonyl, (C1-C4)- Alkylsulfonyl, (C3-C5)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C4)-Alkylsulfinyl, (C3-Cs)- Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C4)-Dialkylsulfonimidoyl, S-(Ci-C4)-Alkylsulfonimidoyl, (Ci-C4)-Alkylsulfonylaminocarbonyl, (C3-C5)-Cycloalkylsulfonylaminocarbonyl, (C3-Cs)- Cycloalkylaminosulfonyl, Aryl-(Ci-C4)-alkylcarbonylamino, (C3-C5)-Cycloalkyl-(Ci-C4)- alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C4)-Alkoxy-(Ci-C4)-alkylcarbonylamino, (Ci-C4)-Hydroxyalkylcarbonylamino, (Ci-C4)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 4) -Aminoalkylsulfonyl, (C 1 -C 4) - alkylaminosulfonyl, (Ci-C 4) -Bisalkylaminosulfonyl, (C 3 -C 5) -Cycloalkylaminosulfonyl, (C 1 -C 4) - Haloalkylaminosulfonyl, arylaminosulfonyl, aryl (Ci-C4) -alkylaminosulfonyl, (C 1 -C 4) - alkylsulfonyl, (C 3 -C 5) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 4) alkylsulfinyl, (C 3 - Cs) -cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 4 ) -dialkylsulfonimidoyl, S- (Ci-C 4 ) -alkylsulfonimidoyl, (Ci-C 4 ) -alkylsulfonylaminocarbonyl, (C 3 -C 5 ) -cycloalkylsulfonylaminocarbon (C 3 -Cs) cycloalkylaminosulfonyl, aryl- (Ci-C 4 ) -alkylcarbonylamino, (C 3 -C 5 ) -cycloalkyl- (Ci-C 4 ) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkylcarbonylamino, (Ci-C 4 ) -hydroxyalkylcarbonylamino, (Ci-C 4 ) -trialkylsilyl, except for the following connections:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8])  N- (2-fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8])
Im Speziellen bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Q für die Gruppen Q-l.l bis Q-10.14 Particularly preferred subject matter of the invention are compounds of the general formula (I) in which Q is for the groups Q-1.1 to Q-10.14
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000026_0001
Figure imgf000027_0001
Figure imgf000028_0001
Figure imgf000029_0001
Figure imgf000030_0001
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0002
Figure imgf000031_0001
Figure imgf000032_0001
Figure imgf000033_0002
steht,  stands,
Z für die Gruppen Z-l.l bis Z-4.3  Z for groups Z-l.l to Z-4.3
Figure imgf000033_0001
Figure imgf000034_0001
steht, und
Figure imgf000033_0001
Figure imgf000034_0001
stands, and
R1 für Methyl, Ethyl, n-Propyl, Isopropyl, Cyclopropyl, Cyclopropylmethyl, Benzyl, p-Methoxy- benzyl, 2-Phenethyl, Allyl, Propargyl steht, ausgenommen der nachfolgend genannten Verbindungen: R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxybenzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8])  N- (2-fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8])
Im ganz Speziellen bevorzugter Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly preferred subject matter of the invention are compounds of the general formula (I) in which
Q für eine der zuvor spezifisch genannten Gruppen Q- 1.1 bis Q- 10.14 steht, Q represents one of the groups Q- 1.1 to Q- 10.14 specifically mentioned above,
Z für eine der zuvor spezifisch genannten Gruppen Z-l .1 bis Z-4.3 steht, und Z stands for one of the groups Z-1 .1 to Z-4.3 specifically mentioned above, and
R1 für Methyl, Ethyl, Cyclopropylmethyl, Benzyl, 2-Phenethyl, Allyl, Propargyl steht, ausgenommen der nachfolgend genannten Verbindungen: R 1 represents methyl, ethyl, cyclopropylmethyl, benzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8]).  N- (2-Fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8]).
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der allgemeinen Formel (I) 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 (I) and correspondingly to those for Production of required starting or intermediate products. These residual definitions can
untereinander, also auch zwischen den angegebenen bevorzugten Bereichen beliebig kombiniert werden. can be combined with each other, i.e. also between the specified preferred ranges.
Vor allem aus den Gründen der höheren herbiziden Wirkung, besseren Selektivität und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten allgemeinen Formel (I) oder deren Salze bzw. deren erfindungsgemäße Verwendung 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. Especially for the reasons of the higher herbicidal activity, better selectivity and / or better producibility, compounds of the general formula (I) according to the invention or their salts or their use according to the invention are of particular interest, wherein individual radicals are one of those already mentioned or mentioned below have preferred meanings, 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 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, i.e. for example in the case of (C2-Cg) alkenyloxy via the oxygen atom, and in the case of heterocyclyl (Ci-Cg) alkyl in each case via the C atom of the alkyl group.
Erfindungsgemäß steht "Alkylsulfonyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges 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-methyl 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, l, l-dimethylbutylsulfonyl, l, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3, 3-sulfonylbutylsylonyl 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" stands for 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. 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 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. 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
Kohlenstoffatomen, wie (Ci-Cio)-, (C i-Cr,)- oder (Ci-C i)-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. Carbon atoms, such as (Ci-Cio) -, (C i-Cr,) - or (Ci-C i) -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, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 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-trimethylpropylthio, 1, 2,2-trimethylpropylthio, l-ethyl-l-methylpropylthio and 1- Ethyl-2-methyl-propylthio.
„Cycloalkylthio“ bedeutet bedeutet erfindungsgemäß ein über ein Schwefelatom gebundenen According to the invention, “cycloalkylthio” means one bonded via a sulfur atom
Cycloalkylrest. Cycloalkyl group.
„Alkylsulfinyl (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)-, (CI-CÖ)- oder (Ci-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfinyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfinyl, 2-Methylpropylsulfinyl,"Alkylsulfinyl (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) -, ( CI-C Ö ) - or (Ci-C 4 ) - alkylsulfinyl, e.g. B. (but not limited to) (Ci-C 6 ) alkylsulfinyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl,
1 , 1 -Dimethylethylsulfinyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, l,l-Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1 -Ethylpropylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3 -Methylpentylsulfinyl, 4-Methylpentylsulfinyl, l,l-Dimethylbutylsulfinyl, 1 ,2-Dimethyl- butylsulfinyl, l,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1 -Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, l,l,2-Trimethylpropylsulfinyl, 1,2,2- Trimethylpropylsulfinyl, l-Ethyl-l -methylpropylsulfinyl und 1 -Ethyl-2-methylpropylsulfinyl. 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, l, l-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, l, l-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, l, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, l, l, 2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, l-ethyl-l-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
„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. „Cycloalkyloxy“ bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest. “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-methyl propoxy 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) -, (C2-C6) - or (C2-C4) -alkenoxy or (C3-C10) -, (C3 -C6) - or (C3-C 4 ) alkynoxy. “Cycloalkyloxy” means a cycloalkyl 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 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-C4) 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) -, (C2-C6) - or (C2-C 4 ) alkenyloxycarbonyl or (C3-C 10) -, (C3-C6) - 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. 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 skeleton 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.
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, 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, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, 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, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthoxy, haloalkyl, haloalkyl Cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroraryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris- [alkyl] silyl, bis- [alkyl] arylsilyl, bis- [alkyl] alkylsilyl, tris- [alkyl] silylalkynyl, alkylalkynyl, cycloalkylalkynyl, Haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino,
Alkylcarbonylamino, Cycloalkylcarbonylamino, Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Alkylcarbonylamino, cycloalkylcarbonylamino, arylcarbonylamino, alkoxycarbonylamino, Alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl, bis-alkylaminocarbonyl,
Heteroarylalkoxy, Arylalkoxy. Heteroarylalkoxy, 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 heteroaromatic and can be unsubstituted or substituted, where the binding site is 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 8-aza-bicyclo [3.2.1] octanyl, 8-aza-bicyclo [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 should be directly adjacent, such as 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-azepine
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-azepin-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- 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- oder2- 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- 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- oder 5- oder 6- oder 7-yl; 2,3,6,7-Tetrahydrooxepin-2- oder 3- oder 4-yl; 2,3-Dihydrooxepin-2- oder 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- oder4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydrooxepin-2- or 3- or 4-yl; 2,3-dihydrooxepin-2- or 3- 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, 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- oder2- 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 the 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
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- oder 4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-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 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- 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- oder6- 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-oxazepine 2- 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- oder 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; 2,5-7-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- 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- 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: 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 for optionally further substituted heterocycles are also listed below:
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_0001
Figure imgf000042_0001
Figure imgf000043_0001
Figure imgf000044_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, hydrogen, halogen, alkyl, haloalkyl, hydroxyl, 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, aminocarbonyl,
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. If a basic body is substituted “by one or more residues” from an enumeration of residues (= group) or a generically defined group of residues, then this includes the simultaneous substitution by several identical and / or structurally different residues.
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 the nitrogen heterocycle is partially or fully saturated, it can be linked to the rest of the molecule via carbon as well as 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. Lactones and lactams are thereby preferably also included. The oxo group can also occur on the hetero ring atoms, which can exist in various oxidation states, for example N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (0) 2 ( also 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; 1H-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; 1H-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; 1H-imidazol-5-yl; lH-pyrazol-l-yl; 1H-pyrazol-3-yl; 1H-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 also 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 another aromatic ring, so they are fused heteroaromatic systems, such as benzo-fused or multi-fused heteroaromatic.
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-Benzofüran-2-yl, l-Benzofüran-3-yl, l-Benzofüran-4-yl, l-Benzofüran-5- yl, l-Benzofüran-6-yl, l-Benzofüran-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; Cinnolin; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; Phthalazine; Pyridopyrazine; Pyridopyrimidines; Pyridopyridazines; Pteridine; Pyrimidopyrimidines. 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-benzthiazol-2-yl, l, 3-benzthiazol-4-yl, l, 3-benzthiazol-5-yl, l, 3-benzthiazol-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 beispielsweise Fluor, Chlor, Brom oder Iod. Wird die The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. Will the
Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom. Name used for a radical, then "halogen" means for example 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 lod. Die Vorsilbe„Bis“ schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl(Methyl). „Haloalkyl“, ,,-alkenyl“ und ,,-alkinyl“ bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl 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” and “- alkynyl” mean alkyl, alkenyl or alkynyl, for example monohaloalkyl, which is partially or completely substituted by identical or different halogen atoms
(= Monohalogenalkyl) wie z. B. CH2CH2CI, CH2CH2Br, CHCICH3, CH2CI, CH2F; Perhaloalkyl wie z. B. CCI3, CCIF2, CFC12,CF2CC1F2, CF2CCIFCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. (= 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, 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 “Partially fluorinated haloalkyl” means a straight-chain or branched, saturated
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. 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 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 residues 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 lower carbon skeletons, for example with 1 to 6 C atoms or, in the case of unsaturated groups, with 2 to 6 C atoms, are preferred for the hydrocarbon radicals, such as alkyl, alkenyl and alkynyl radicals, even in composite radicals. Alkyl radicals, also in the composite radicals such as alkoxy, haloalkyl, etc., mean, for example, 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 gegebenenfalls durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (CAGO-Alkcnyl wie Ethenyl, 1 -Propenyl, 2-Propenyl, 1 -Methylethenyl, 1 -Butenyl, 2- Butenyl, 3-Butenyl, 1 -Methyl- 1 -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-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, l,l-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, l-Methyl-4- pentenyl, 2-Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl,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 e.g. Vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (CAGO-alkyl, such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl , 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1 -Methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl -3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, l, l-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-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl , 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, l-methyl-4-pen tenyl, 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, l,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- Dimethy 1-2 -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. 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl 1-2 -butenyl, l-ethyl-l-butenyl, 1-ethyl-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 geradketige oder verzweigte offenketige 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, 1,1 -Dimethyl-3- butinyl, l,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 l-Ethyl-l-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, for example, 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, 2nd -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, 1,1 -dimethyl-3- butinyl, l, 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, multicyclic 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, adamantane 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. =CH2, =CH-CH3, =C(CH3)-CH3, =C(CH3)-C2H5 oder =C(C2FF)-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. = CH2, = CH-CH 3 , = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or = C (C2FF) -C2FF . Cycloalkylidene means a
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. „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. carbocyclic radical which is bonded via a double bond. "Alkoxyalkyl" stands for an alkoxy radical bonded via an alkyl group and "alkoxyalkoxy" means an alkoxyalkyl radical bonded via an oxygen atom, for example (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. “Heteroaryloxyalkyl” means a heteroaryloxy radical bonded via an alkyl group.
„Haloalkoxyalkyl“ steht für einen gebundenen Haloalkoxyrest und„Haloalkylthioalkyl“ bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. “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-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylprop-1-yl, 3-cyclopropylprop-1-yl.
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 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. 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 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-1-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.
Erfindungsgemäß steht "Trialkylsilyl" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes Si- Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention, "trialkylsilyl" - alone or as part of a chemical group - stands for straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie Tri-[(Ci-C8)-, (C i-Cr,)- oder (Ci-C i)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl, Tri-(n-propyl)silyl, Tri-(iso-propyl)silyl, Tri-(n-butyl)silyl, Tri-(l- methylprop-l-yl)silyl, Tri-(2-methylprop-l-yl)silyl, Tri(l,l-Dimethyleth-l-yl)silyl, Tri(2,2- Dimethyleth- 1 -yl)silyl. Carbon atoms, such as tri - [(Ci-C 8 ) -, (C i-Cr,) - or (Ci-C i) alkyl] silyl, for example (but not limited to) Trimethylsilyl, triethylsilyl, tri- (n-propyl) silyl, tri- (iso-propyl) silyl, tri- (n-butyl) silyl, tri- (l-methylprop-l-yl) silyl, tri- (2-methylprop -l-yl) silyl, tri (l, l-dimethyleth-l-yl) silyl, tri (2,2-dimethyleth-1-yl) silyl.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die allgemeine Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele If the compounds can form tautomers by hydrogen shift, which would not be structurally formally covered by the general formula (I), these tautomers are nevertheless included in the definition of the compounds of the general formula (I) according to the invention, unless a specific tautomer is the subject of consideration is. For example, many
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. 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 Stereoisomeren, die von der allgemeinen Formel (I) umfasst, jedoch nicht mit ihrer spezifischen Stereoform angegeben sind, sowie deren Gemische. 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. Stereoisomers can also be prepared 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 their mixtures.
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 (I) nicht auf den nachstehend beschriebenen Wegen zufriedenstellend zugänglich sind, können sie durch Derivatisierung anderer Verbindungen (I) hergestellt werden. Recrystallize or digest. If individual compounds (I) are not satisfactorily accessible in the ways described below, they can be prepared by derivatizing other compounds (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. 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 processes, any remaining mixtures can generally be separated by chromatographic separation, for example on chiral solid phases. Processes can be used for preparative quantities or on an industrial scale such as crystallization, for example diastereomeric salts, which can be obtained from the diastereomer mixtures with optically active acids and, if appropriate, with acid groups present with optically active bases.
Synthese von substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamiden der allgemeinen Formel (I). Synthesis of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I).
Die erfindungsgemäßen substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamiden der allgemeinen Formel (I) können ausgehend von bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Aminen, von entsprechend substituierten Aldehyden und von kommerziell erhältlichen Chemikalien wie Malonsäurederivaten und Nitromethan aus. Die Gruppierungen Q, Z, R1 und R2 der allgemeinen Formel (I) haben in den nachfolgenden Schemata die zuvor definierten Bedeutungen, sofern nicht beispielhafte, aber nicht einschränkende, Definitionen erfolgen. The substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the general formula (I) according to the invention can be prepared starting from known processes. The synthetic routes used and investigated are based on commercially available or easily produced amines, on appropriately substituted aldehydes and on commercially available chemicals such as malonic acid derivatives and nitromethane. The groupings Q, Z, R 1 and R 2 of the general formula (I) have the meanings previously defined in the following schemes, unless exemplary but not restrictive definitions are given.
Die Synthese der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) erfolgt über eine Alkylierung von einem Amid der allgemeinen Formel (II) mit einer alkylierenden Verbindung der allgemeinen Formel (III) in Gegenwart einer Base wie zum Beispiel Kaliumcarbonat oder The compounds of the general formula (I) according to the invention are synthesized via an alkylation of an amide of the general formula (II) with an alkylating compound of the general formula (III) in the presence of a base such as, for example, potassium carbonate or
Natriumcarbonat. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 0 °C und 100 °C, in einem adäquaten Lösungsmittel wie zum Beispiel Dichlormethan, Acetonitril, W-Dimcthyl- formamid oder Ethylacetat statt (siehe Schema 1). Die Amidgruppe und der Rest Q nehmen Sodium. The reaction preferably takes place in the temperature range between 0 ° C and 100 ° C, in an adequate solvent such as dichloromethane, acetonitrile, W-dimethylformamide or ethyl acetate (see Scheme 1). Take the amide group and the rest Q.
überwiegend die trans-Konfiguration ein. Das cis-Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. predominantly the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000052_0001
Figure imgf000052_0001
Mit X = Halogen.  With X = halogen.
Schema 1. Scheme 1.
Die Synthese der Verbindungen der allgemeinen Formel (II) erfolgt über eine Aminolyse von einem Ester der allgemeinen Formel (IV) mit einem Amin der allgemeinen Formel (V). Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 20 °C und 180 °C statt (siehe Schema 2) und kann ohne Lösungsmittel durch Aufschmelzen durchgeführt werden. Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis-Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. The compounds of the general formula (II) are synthesized by aminolysis of an ester of the general formula (IV) with an amine of the general formula (V). The reaction preferably takes place in the temperature range between 20 ° C and 180 ° C (see scheme 2) and can be carried out without solvent by melting. Take the amide group and the rest Q. predominantly the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000053_0001
Figure imgf000053_0001
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 2. Scheme 2.
Die Synthese der Verbindungen der allgemeinen Formel (IV) erfolgt über die Reaktion der allgemeinen Formel (VI) mit einem Schwefelungs-Reagenz, wie zum Beispiel Phosphorpentasulfid oder Lawessons Reagenz. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 20 °C und 180 °C, in einem adäquatem Lösungsmittel wie zum Beispiel Toluol, Chlorbenzol oder Dichlorbenzol statt (siehe Schema 3). Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis- Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. The compounds of the general formula (IV) are synthesized by reacting the general formula (VI) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent. The reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 3). The amide group and the rest Q predominantly assume the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000053_0002
Figure imgf000053_0002
(VI) (IV)  (VI) (IV)
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 3. Scheme 3.
Die Synthese der Verbindung der allgemeinen Formel (VI) lässt sich durch Reduktion der Verbindung der allgemeinen Formel (VII) und anschließender in situ Cyclisierung des enstehenden Amin- Intermediates nach oder analog dem Fachmann bekannten Methoden hersteilen (siehe Schema 4). In der Literatur ist die Reduktion von aliphatischen Nitro-Gruppen durch katalytische Hydrogenolyse inThe synthesis of the compound of the general formula (VI) can be prepared by reduction of the compound of the general formula (VII) and subsequent in situ cyclization of the amine intermediate formed by or analogously to methods known to the person skilled in the art (see Scheme 4). The reduction of aliphatic nitro groups by catalytic hydrogenolysis is in the literature
Gegenwart von Palladium auf Kohle oder RaneyNickel, Eisen oder Zink im sauren Medium (siehe zum Beispiel Berichte der Deutschen Chemischen Gesellschaft 1904, 37, 3520-3525), und Lithiumalanat beschrieben. Die Reduktion lässt sich auch mit Samarium(II)iodid in Gegenwart einer Protonen-Quelle wie zum Beispiel Methanol (siehe zum Beispiel Tetrahedron Leiters 1991, 32 (14), 1699-1702) durchführen. Alternativ lässt sich die Reduktion der aliphatischen Nitro-Gruppe mit Natriumborhydrid in Gegenwart von Nickel(II)acetat oder Nickel(II)chlorid (siehe zum Beispiel Tetrahedron Leiters 1985, 26 (52), 6413-6416) durchführen.
Figure imgf000054_0001
Presence of palladium on coal or RaneyNickel, iron or zinc in the acidic medium (see for example reports of the German Chemical Society 1904, 37, 3520-3525), and lithium alanate. The reduction can also be carried out with samarium (II) iodide in the presence of a proton source such as, for example, methanol (see, for example, Tetrahedron Leiters 1991, 32 (14), 1699-1702). Alternatively, the reduction of the aliphatic nitro group with sodium borohydride can be carried out in the presence of nickel (II) acetate or nickel (II) chloride (see, for example, Tetrahedron Leiters 1985, 26 (52), 6413-6416).
Figure imgf000054_0001
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 4. In Schema 5 wird die Synthese der Verbindung der allgemeinen Formel (VII) durch Reaktion einesScheme 4. In Scheme 5, the synthesis of the compound of general formula (VII) by reaction of a
Diesters der allgemeinen Formel (VIII) mit Nitromethan (IX) in Gegenwart einer Base beschrieben. Die Base kann ein Alkanolat-Salz von einem Alkali-Metall (wie zum Beispiel Natriummethylat oder Natriumethylat) sein, in einem adäquaten Lösungsmittel wie zum Beispiel Methanol oder Ethanol. Alternativ kann man die Reaktion mit Basen wie Lithiumhexa-methyldisilazan, Diesters of the general formula (VIII) with nitromethane (IX) in the presence of a base. The base may be an alkanolate salt of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol. Alternatively, the reaction can be carried out with bases such as lithium hexamethyldisilazane,
Natriumhexamethyldisilazan oder Lithiumdiisopropylamid, in einem adäquaten Lösungsmittel wie zum Beispiel Tetrahydrofuran durchführen. Carry out sodium hexamethyldisilazane or lithium diisopropylamide in an adequate solvent such as tetrahydrofuran.
Figure imgf000054_0002
Figure imgf000054_0002
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 5.  Scheme 5.
Die Verbindungen der allgemeinen Formel (VIII) lassen sich durch Knoevenagel Kondensation eines Aldehydes der allgemeinen Formel (XI) und Malonestem der allgemeinen Formel (XII) hersteilen (siehe Schema 6; G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967). The compounds of general formula (VIII) can be prepared by Knoevenagel condensation of an aldehyde of general formula (XI) and malonic esters of general formula (XII) (see Scheme 6; G. Jones, Organic Reactions Volume 15, John Wiley and Sons, 1967 ).
Figure imgf000054_0003
Figure imgf000054_0003
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 6. In Schema 7 wird die Synthese der Verbindung der allgemeinen Formel (VII) durch Reaktion eines Malonesters der allgemeinen Formel (XII) mit einem Nitroolefin der allgemeinen Formel (XIII) in Gegenwart einer Base beschrieben. Die Base kann ein Alkanolat-Salz bzw. Hydroxid von einem Alkali- Metall (wie zum Beispiel Natriummethylat oder Natriumethylat) sein, in einem adäquaten Lösungsmittel wie zum Beispiel Methanol oder Ethanol, oder Basen wie Lithiumhexamethyldisilazan, Scheme 6. Scheme 7 describes the synthesis of the compound of the general formula (VII) by reacting a malonic ester of the general formula (XII) with a nitroolefin of the general formula (XIII) in the presence of a base. The base may be an alkanolate salt or hydroxide of an alkali metal (such as sodium methylate or sodium ethylate) in an adequate solvent such as methanol or ethanol, or bases such as lithium hexamethyldisilazane,
Natriumhexamethyldisilazan oder Lithiumdiisopropylamid, in einem adäquaten Lösungsmittel wie zum Beispiel Tetrahydrofuran durchführen.  Carry out sodium hexamethyldisilazane or lithium diisopropylamide in an adequate solvent such as tetrahydrofuran.
Figure imgf000055_0001
Figure imgf000055_0001
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 7. Scheme 7.
Die Verbindungen der allgemeinen Formel (XIII) lassen sich durch Kondensation eines Aldehydes der allgemeinen Formel (XI) und Verbindungen der allgemeinen Formel (IX) in Gegenwart einer Base wie zum Beispiel Natriumhydrid, in einem adäquaten Lösungsmittel wie zum Beispiel Tetrahydrofuran hersteilen (siehe Schema 8). The compounds of the general formula (XIII) can be prepared by condensing an aldehyde of the general formula (XI) and compounds of the general formula (IX) in the presence of a base such as sodium hydride in an adequate solvent such as tetrahydrofuran (see Scheme 8 ).
Figure imgf000055_0002
Figure imgf000055_0002
(XI) (IX)  (XI) (IX)
(Xi")  (Xi ")
Schema 8.  Scheme 8.
Die Synthese der Verbindungen der allgemeinen Formel (II) erfolgt über die Reaktion der allgemeinen Formel (XV) mit einem Schwefelungs-Reagenz, wie zum Beispiel Phosphorpentasulfid oder Lawessons Reagenz. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 20 °C und 180 °C, in einem adäquatem Lösungsmittel wie zum Beispiel Toluol, Chlorbenzol oder Dichlorbenzol statt (siehe Schema 9). Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis- Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. Bei der Reaktion kann auch die Verbindung der allgemeinen Formel (XIV) entstehen.
Figure imgf000056_0001
The compounds of the general formula (II) are synthesized by reacting the general formula (XV) with a sulfurization reagent, such as, for example, phosphorus pentasulfide or Lawesson's reagent. The reaction preferably takes place in the temperature range between 20 ° C and 180 ° C, in an adequate solvent such as toluene, chlorobenzene or dichlorobenzene (see scheme 9). The amide group and the rest Q predominantly assume the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR. The compound of the general formula (XIV) can also be formed in the reaction.
Figure imgf000056_0001
Schema 9.  Scheme 9.
Die Synthese der Verbindungen der allgemeinen Formel (XV) erfolgt über eine Amidkupplung von einer Säure der allgemeinen Formel (XVI) mit einem Amin der allgemeinen Formel (V) in Gegenwart eines Amidkupplungsreagenzes wie zum Beispiel T3P, Dicyclohexylcarbodiimid, N-(3- Dimcthylaminopropyl)-/\"-cthylcarbodiimid, /V, ,V C a b o n y 1 d i i m i d azo 1 , 2-Chlor-l,3-dimethyl- imidazolium chlorid oder 2-Chlor-l-methylpyridinium iodid (siehe Chemistry of Peptide Synthsis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymergebundene Reagenzien wie zum Beispiel polymergebundenes Dicyclohexylcarbodiimid sind auch für diese Kupplungs-reaktion geeignet. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 0 °C und 80 °C, in einem adäquaten Lösungsmittel wie zum Beispiel Dichlormethan, Acetonitril, ,V, ,V- D i m c t hy 1 - f o r ma m i d oder Ethylacetat und in Gegenwart eine Base wie zum Beispiel Triethylamin, /V, ,V- D i i s o p ro p y 1 c t h y 1 a m i n oder l,8-Diazabicyclo[5.4.0]undec-7-cen statt (siehe Schema 10). Für die T3P Peptidkupplungsbedingungen siehe Organic Process Research & Development 2009, 13, 900-906. Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis-Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. The compounds of the general formula (XV) are synthesized via an amide coupling of an acid of the general formula (XVI) with an amine of the general formula (V) in the presence of an amide coupling reagent such as, for example, T3P, dicyclohexylcarbodiimide, N- (3-dimcthylaminopropyl) - / \ "- cthylcarbodiimide, / V,, VC abony 1 diimid azo 1, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthsis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction takes place preferably in the temperature range between 0 ° C. and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile, V,, V-D imct hy 1 - for ma mid or ethyl acetate and in the presence of a base such as triethylamine, / V,, V-D iisop ro py 1 cthy 1 a m i n or l, 8-diazabicyclo [5.4.0] undec-7-cen instead (see Scheme 10). For the T3P peptide coupling conditions see Organic Process Research & Development 2009, 13, 900-906. The amide group and the rest Q predominantly assume the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000056_0002
Figure imgf000056_0002
Schema 10.  Scheme 10.
Die Synthese der Säure der allgemeinen Formel (XVI) lässt sich durch Verseifung der Verbindung der allgemeinen Formel (VI) nach oder analog dem Fachmann bekannten Methoden hersteilen (Schema 11). Die Verseifung lässt sich in Gegenwart einer Base oder einer Lewis-Säure durchführen. Die Base kann ein Hydroxid-Salz von einem Alkali-Metall (wie zum Beispiel Lithium, Natrium oder Kalium) sein, und die Verseifungsreaktion findet bevorzugt in dem Temperaturbereich zwischen Raumtemperatur und 100 °C statt. Die Lewis-Säure kann Bortribromid sein, und die Reaktion in einem Temperaturbereich zwischen -20 °C und 100 °C, vorzugsweise -5 °C und 50 °C durchgeführt werden.
Figure imgf000057_0001
The synthesis of the acid of the general formula (XVI) can be prepared by saponification of the compound of the general formula (VI) according to or analogously to methods known to the skilled worker (Scheme 11). The saponification can be carried out in the presence of a base or a Lewis acid. The base can be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium) and the saponification reaction preferably takes place in the temperature range between room temperature and 100 ° C. The Lewis acid can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
Figure imgf000057_0001
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 11. Die Synthese der Verbindungen der allgemeinen Formel (Ia) erfolgt über eine Amidkupplung von einer Säure der allgemeinen Formel (XVII) mit einem Amin der allgemeinen Formel (V) in Gegenwart eines Amidkupplungsreagenzes wie zum Beispiel T3P, Dicyclohexylcarbodiimid, N-(3- Dimcthylaminopropyl)-/\"-cthylcarbodiimid, /V, ,V C a b o n y 1 d i i m i d azo 1 , 2-Chlor-l,3-dimethyl- imidazolium chlorid oder 2-Chlor-l-methylpyridinium iodid (siehe Chemistry of Peptide Synthsis, Ed. N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymergebundene Reagenzien wie zum Beispiel polymergebundenes Dicyclohexylcarbodiimid sind auch für diese Kupplungs-reaktion geeignet. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 0 °C und 80 °C, in einem adäquaten Lösungsmittel wie zum Beispiel Dichlormethan, Acetonitril, ,V, ,V- D i m c t hy 1 - f o r ma m i d oder Ethylacetat und in Gegenwart eine Base wie zum Beispiel Triethylamin, /V, ,V- D i i s o p ro p y 1 c t h y 1 a m i n oder l,8-Diazabicyclo[5.4.0]undec-7-cen statt (siehe Schema 12). Für die T3P Peptidkupplungsbedingungen siehe Organic Process Research & Development 2009, 13, 900-906. Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis-Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. Scheme 11. The synthesis of the compounds of general formula (Ia) takes place via an amide coupling of an acid of general formula (XVII) with an amine of general formula (V) in the presence of an amide coupling reagent such as T3P, dicyclohexylcarbodiimide, N- (3 - Dimcthylaminopropyl) - / \ "- Cthylcarbodiimid, / V,, VC abony 1 diimid azo 1, 2-chloro-l, 3-dimethyl-imidazolium chloride or 2-chloro-l-methylpyridinium iodide (see Chemistry of Peptide Synthsis, Ed N. Leo Benoiton, Taylor & Francis, 2006, ISBN-10: 1-57444-454-9). Polymer-bound reagents such as polymer-bound dicyclohexylcarbodiimide are also suitable for this coupling reaction. The reaction preferably takes place in the temperature range between 0 ° C and 80 ° C, in an adequate solvent such as dichloromethane, acetonitrile,, V,, V- D imct hy 1 - for ma mid or ethyl acetate and in the presence of a base such as triethylamine, / V,, V- D iisop ro py 1 c t h y 1 a m i n or l, 8-diazabicyclo [5.4.0] undec-7-cen instead (see Scheme 12). For the T3P peptide coupling conditions see Organic Process Research & Development 2009, 13, 900-906. The amide group and the rest Q predominantly assume the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000057_0002
Figure imgf000057_0002
Schema 12. Scheme 12.
Die Synthese der Säure der allgemeinen Formel (XVII) lässt sich durch Verseifung der Verbindung der allgemeinen Formel (XVIII) nach oder analog dem Fachmann bekannten Methoden hersteilen (Schema 13). Die Verseifung lässt sich in Gegenwart einer Base oder einer Lewis-Säure durchführen. Die Base kann ein Hydroxid-Salz von einem Alkali-Metall (wie zum Beispiel Lithium, Natrium oder Kalium) sein, und die Verseifungsreaktion findet bevorzugt in dem Temperaturbereich zwischen The synthesis of the acid of the general formula (XVII) can be prepared by saponification of the compound of the general formula (XVIII) according to or analogously to methods known to the person skilled in the art (Scheme 13). The saponification can be carried out in the presence of a base or a Lewis acid. The base may be a hydroxide salt of an alkali metal (such as lithium, sodium or potassium) and the saponification reaction preferably takes place in the temperature range between
Raumtemperatur und 100 °C statt. Die Lewis-Säure kann Bortribromid sein, und die Reaktion in einem Temperaturbereich zwischen -20 °C und 100 °C, vorzugsweise -5 °C und 50 °C durchgeführt werden.
Figure imgf000058_0001
Room temperature and 100 ° C instead. The Lewis acid can be boron tribromide and the reaction can be carried out in a temperature range between -20 ° C and 100 ° C, preferably -5 ° C and 50 ° C.
Figure imgf000058_0001
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 13. Die Synthese der Verbindungen der allgemeinen Formel (XVIII) erfolgt über eine Alkylierung von einem Esterder allgemeinen Formel (IV) mit einer Verbindung der allgemeinen Formel (III) in Gegenwart einer Base wie zum Beispiel Kaliumcarbonat oder Natriumcarbonat. Die Reaktion findet bevorzugt in dem Temperaturbereich zwischen 0 °C und 100 °C, in einem adäquaten Lösungsmittel wie zum Beispiel Dichlormethan, Acetonitril, ,V, ,V- D i m c t hy 1 - f o r ma m i d oder Ethylacetat statt (siehe Schema 14). Die Amidgruppe und der Rest Q nehmen überwiegend die trans-Konfiguration ein. Das cis-Isomer lässt sich in einigen Fällen in geringen Mengen per NMR detektieren. Scheme 13. The synthesis of the compounds of the general formula (XVIII) takes place via an alkylation of an ester of the general formula (IV) with a compound of the general formula (III) in the presence of a base such as, for example, potassium carbonate or sodium carbonate. The reaction preferably takes place in the temperature range between 0 ° C and 100 ° C, in an adequate solvent such as dichloromethane, acetonitrile,, V,, V- D i m c t hy 1 - for m i d or ethyl acetate (see Scheme 14). The amide group and the rest Q predominantly assume the trans configuration. In some cases, the cis isomer can be detected in small amounts by NMR.
Figure imgf000058_0002
Figure imgf000058_0002
Mit X = Halogen.  With X = halogen.
Mit R' = (Ci-C4)-Alkyl. With R '= (Ci-C 4 ) alkyl.
Schema 14. Scheme 14.
Alternativ lassen sich die Verbindungen der der allgemeinen Formel (I) nach oder analog dem Alternatively, the compounds of the general formula (I) according to or analogous to
Fachmann bekannten Methoden hersteilen (siehe WO2016/182780). Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) sind im Folgenden aufgeführt. Die angegebenen Beispielnummem entsprechen den in den nachstehenden Tabellen 1.1 bis 1.82 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 CDCF, CD3OD oder dö-DMSO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Broker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, 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. Manufacture methods known to those skilled in the art (see WO2016 / 182780). Selected detailed synthesis examples for the compounds of the general formula (I) according to the invention are listed below. The example numbers given correspond to the numbering given in Tables 1.1 to 1.82 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 CDCF, CD3OD or d ö -DMSO, internal standard: tetramethylsilane d = 0.00 ppm) were obtained with a Broker device, and the signals indicated have the meanings given below: br = broad (es); 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 the following meanings, for example: 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.
Synthesebeispiele: Synthesis examples:
Synthesebeispiel No. 1.51-12: (3/?*,45)-N-(2,3-Dihydro-lH-inden-4-yl)-5-(methylsulfanyl)-3-[3- (trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4-carboxamid  Synthesis example No. 1.51-12: (3 /? *, 45) -N- (2,3-dihydro-lH-inden-4-yl) -5- (methylsulfanyl) -3- [3- (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide
Synthesestufel : Diethyl 2-[[3-(trifluoromethyl)phenyl]methylen]propanedioat
Figure imgf000059_0001
Synthesis level: Diethyl 2 - [[3- (trifluoromethyl) phenyl] methylene] propane dioate
Figure imgf000059_0001
3-Trifluoromethylbenzaldehyd (15.0 g, 86.15 mmol, 1.0 equiv) und Diethylmalonat (14.4 ml, 144 mmol, 1.1 equiv) wurde in Toluol (200 ml) gelöst, und mit Piperidin (1.28 ml, 12.9 mmol, 0.1 equiv) versetzt. Das resultierende Reaktionsgemisch wurde am Wasserabscheider über Nacht unter Rückfluss gerührt und anschließend auf Raumtemperatur abgekühlt und mit 1M wässriger HCl und ges. 3-trifluoromethylbenzaldehyde (15.0 g, 86.15 mmol, 1.0 equiv) and diethyl malonate (14.4 ml, 144 mmol, 1.1 equiv) were dissolved in toluene (200 ml) and piperidine (1.28 ml, 12.9 mmol, 0.1 equiv) was added. The resulting reaction mixture was stirred under reflux on a water separator overnight and then cooled to room temperature and washed with 1M aqueous HCl and sat.
Natriumchloridlösung gewaschen, über Natriumsulfat getrocknet, filtriert und eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte Diethyl 2-[[3-(trifluoromethyl)phenyl]methylen]propanedioat in Form eines gelben Feststoffs isoliert werden (15.3 g, 56% der Theorie).‘H-NMR (400 MHz, CDCI3 d, ppm) 7.74 (s, 1H), 7.71 (s, 1H), 7.66-7.62 (m, 2H), 7.52 (t, 1H), 4.36-4.30 (m, 4H), 1.35 (t, 3H), 1.29 (t, 3H). Washed sodium chloride solution, dried over sodium sulfate, filtered and concentrated. By final column chromatography purification (gradient ethyl acetate / heptane) of the resulting crude product, diethyl 2 - [[3- (trifluoromethyl) phenyl] methylene] propanedioate could be isolated in the form of a yellow solid (15.3 g, 56% of theory). 'H-NMR (400 MHz, CDCI3 d, ppm) 7.74 (s, 1H), 7.71 (s, 1H), 7.66-7.62 (m, 2H), 7.52 (t, 1H), 4.36-4.30 (m, 4H), 1.35 ( t, 3H), 1.29 (t, 3H).
Synthesestufe 2: Diethyl 2-[2-nitro-l-[3-(trifluoromethyl)phenyl]ethyl]propanedioat Synthesis stage 2: diethyl 2- [2-nitro-l- [3- (trifluoromethyl) phenyl] ethyl] propane dioate
Figure imgf000059_0002
Figure imgf000059_0002
Diethyl 2-[[3-(trifluoromethyl)phenyl]methylene]propanedioate (19.6 g, 61.9 mmol, 1.0 equiv) und Nitromethan (33.4 ml, 620 mmol, 10 equiv) wurde in Ethanol (160 ml) gelöst, und mit Natriummethylat (30% Lösung in Methanol, 1.15 ml) versetzt. Das resultierende Reaktionsgemisch wurde über Nacht bei Raumtemperatur gerührt und anschließend eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte Diethyl 2-[2-nitro-l- [3-(trifluoromethyl)phenyl]ethyl]propanedioat in Form eines gelben Öls isoliert werden (17.3 g, 74% der Theorie). 'H-NMR (400 MHz, CDCh d, ppm) 7.58-7.46 (m, 4H), 4.99-4.86 (m, 2H), 4.34-4.18 (m, 3H), 4.03 (q, 2H), 3.82 (d, 1H), 1.28 (t, 3H), 1.07 (t, 3H). Diethyl 2 - [[3- (trifluoromethyl) phenyl] methylene] propanedioate (19.6 g, 61.9 mmol, 1.0 equiv) and nitromethane (33.4 ml, 620 mmol, 10 equiv) was dissolved in ethanol (160 ml) and with sodium methylate ( 30% solution in methanol, 1.15 ml) was added. The resulting reaction mixture was stirred at room temperature overnight and then concentrated. By concluding column chromatography Purification (gradient ethyl acetate / heptane) of the resulting crude product, diethyl 2- [2-nitro-l- [3- (trifluoromethyl) phenyl] ethyl] propanedioate was isolated in the form of a yellow oil (17.3 g, 74% of theory). 'H NMR (400 MHz, CDCh d, ppm) 7.58-7.46 (m, 4H), 4.99-4.86 (m, 2H), 4.34-4.18 (m, 3H), 4.03 (q, 2H), 3.82 (d , 1H), 1.28 (t, 3H), 1.07 (t, 3H).
Synthesestufe 3: (3/?*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidin-3-carbonsäure Synthesis stage 3: (3 /? *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylic acid
Figure imgf000060_0001
Figure imgf000060_0001
Diethyl 2-[2-nitro-l -[3-(trifluoromethyl)phenyl]ethyl]propanedioate (3.00 g, 7.95 mmol, 1.0 equiv) wurde in Ethanol (200 ml) gelöst, und mit Nickel(II)-acetat Tetrahydrat (9.88 g, 39.7 mmol, 5.0 equiv) versetzt. Das resultierende Reaktionsgemisch wurde auf eine Temperatur von 0 °C abgekühlt und mit Natriumborhydrid (1.50 g, 39.7 mmol, 5.0 equiv) portionweise versetzt. Das resultierende Diethyl 2- [2-nitro-l - [3- (trifluoromethyl) phenyl] ethyl] propanedioate (3.00 g, 7.95 mmol, 1.0 equiv) was dissolved in ethanol (200 ml) and treated with nickel (II) acetate tetrahydrate ( 9.88 g, 39.7 mmol, 5.0 equiv) added. The resulting reaction mixture was cooled to a temperature of 0 ° C. and sodium borohydride (1.50 g, 39.7 mmol, 5.0 equiv) was added in portions. The resulting
Reaktionsgemisch wurde über Nacht bei Raumtemperatur gerührt und anschließend wurde ges. The reaction mixture was stirred at room temperature overnight and then sat.
Ammoniumchloridlösung (20ml) und Essigester (20ml) zugegeben und eine weitere Stunde bei Raumtemperatur gerührt. Die unlösbare Bestandteile wurden über Celite abfiltriert und nachfolgend die Phasen getrennt. Die wässrige Phase wurde mehrfach mit Essigester extrahiert, und die vereinigten organischen Phasen wurden danach mit ges. Ammoniumchloridlösung und ges. Natriumchloridlösung gewaschen, über Magnesiumsulfat getrocknet, filtriert und eingeengt. Ammonium chloride solution (20ml) and ethyl acetate (20ml) added and stirred for a further hour at room temperature. The insoluble constituents were filtered off over Celite and the phases were subsequently separated. The aqueous phase was extracted several times with ethyl acetate, and the combined organic phases were then washed with sat. Ammonium chloride solution and sat. Washed sodium chloride solution, dried over magnesium sulfate, filtered and concentrated.
Das resultierende Rohprodukt wurde in Ethanol (40 ml) gelöst, und mit einer Lösung von Natrium hydroxid (1.12 g, 27.8 mmol, 3.0 equiv) in Wasser (40 ml) versetzt. Das resultierende Reaktionsgemisch wurde Übemacht bei Raumtemperatur gerührt und anschließend wurde Wasser (50 ml) und Diethylether (50 ml) zugegeben. Die organische Phase wurde verworfen und die wässrige Phase mit konz. HCl auf pH 2 gestellt. Die wässrige Phase wurde mehrfach mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden danach über Magnesiumsulfat getrocknet, filtriert und eingeengt. Man erhält (3R*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidine-3-carbonsäure in Form eines farblosen Feststoffs (1.57 g, 72% der Theorie nach zwei Stufen). 'H-NMR (400 MHz, DMSO d, ppm) 8.12 (s, 1H) 7.73-7.57 (m, 4H), 3.81 (dd, 1H), 3.66 (dd, 1H), 3.51-3.47 (m, 1H), 3.28-3.23 (dd, 1H). The resulting crude product was dissolved in ethanol (40 ml) and a solution of sodium hydroxide (1.12 g, 27.8 mmol, 3.0 equiv) in water (40 ml) was added. The resulting reaction mixture was stirred at room temperature overnight and then water (50 ml) and diethyl ether (50 ml) were added. The organic phase was discarded and the aqueous phase with conc. HCl adjusted to pH 2. The aqueous phase was extracted several times with dichloromethane, and the combined organic phases were then dried over magnesium sulfate, filtered and concentrated. This gives (3R *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylic acid in the form of a colorless solid (1.57 g, 72% of theory after two steps). 'H NMR (400 MHz, DMSO d, ppm) 8.12 (s, 1H) 7.73-7.57 (m, 4H), 3.81 (dd, 1H), 3.66 (dd, 1H), 3.51-3.47 (m, 1H) , 3.28-3.23 (dd, 1H).
Synthesestufe 4: Ethyl- (3/?*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat
Figure imgf000061_0001
Synthesis step 4: ethyl (3 /? *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate
Figure imgf000061_0001
(3/?*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidin-3-carbonsäure (5.46 g, 19.98 mmol, 1.0 equiv) wurde in Ethanol (50 ml) gelöst und drei Tropfen Schwefelsäure versetzt. Das resultierende Reaktionsgemisch wurde 6 Stunden zum Sieden erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Lösungsmittel im Vakuum entfernt und der Rückstand mit Dichlormethan und Wasser extrahiert. Die organischen Phase über Magnesiumsulfat getrocknet, filtriert und eingeengt. Man erhält Ethyl- (3R*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat in Form eines farblosen Feststoffs (5.51 g, 86% der Theorie). 'H-NMR (400 MHz, DMSO d, ppm) 7.58-7.45 (m, 4H), 6.42 (bs, 1H), 4.26 (q, 2H), 4.18 (m, 1H), 3.86 (dt, 1H), 3.54 (d, 1H), 3.45 (dt, 1H), 1.29 (t, 3H). (3 /? *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylic acid (5.46 g, 19.98 mmol, 1.0 equiv) was dissolved in ethanol (50 ml) and three Drops of sulfuric acid added. The resulting reaction mixture was boiled for 6 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was extracted with dichloromethane and water. The organic phase dried over magnesium sulfate, filtered and concentrated. Ethyl (3R *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate is obtained in the form of a colorless solid (5.51 g, 86% of theory). 'H NMR (400 MHz, DMSO d, ppm) 7.58-7.45 (m, 4H), 6.42 (bs, 1H), 4.26 (q, 2H), 4.18 (m, 1H), 3.86 (dt, 1H), 3.54 (d, 1H), 3.45 (dt, 1H), 1.29 (t, 3H).
Synthesestufe 5: Ethyl- (3R*,45'*)-2-sulfanyliden -4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat Synthesis step 5: ethyl (3R *, 45 '*) - 2-sulfanylidene -4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate
Figure imgf000061_0002
Figure imgf000061_0002
Ethyl-(3R*,45,*)-2-Oxo-4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat (2.25 g, 7.47 mmol, 1.0 equiv) und Lawesson Reagenz (1.51 g, 3.73 mmol, 0.5 equiv) wurden in Toluol (50 ml) gelöst und 7 Stunden zum Sieden erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das Lösungsmittel im Vakuum entfernt und der Rückstand mit Dichlormethan und Wasser extrahiert. Die organischen Phase über Magnesiumsulfat getrocknet, filtriert und im Vakuum eingeengt. Durch abschließende Ethyl (3R *, 45 , *) - 2-oxo-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate (2.25 g, 7.47 mmol, 1.0 equiv) and Lawesson reagent (1.51 g, 3.73 mmol, 0.5 equiv) were dissolved in toluene (50 ml) and heated to boiling for 7 hours. After cooling to room temperature, the solvent was removed in vacuo and the residue was extracted with dichloromethane and water. The organic phase dried over magnesium sulfate, filtered and concentrated in vacuo. By closing
säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte Ethyl-(3R*,45'*)-2-sulfanyliden -4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat in Form eines farblosen Feststoffs (1.93 g, 77% der Theorie).‘H-NMR (400 MHz, CDCF d, ppm) 8.00 (bs, 1H), 7.58-7.43 (m, 4H), 4.33-4.11 (m, 3H), 3.89 (m, 1H), 3.70 (dd, 1H), 1.31 (t, 3H). column chromatography purification (gradient ethyl acetate / heptane) of the resulting crude product was able to give ethyl (3R *, 45 '*) - 2-sulfanylidene -4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate in the form of a colorless solid (1.93 g , 77% of theory). 'H NMR (400 MHz, CDCF d, ppm) 8.00 (bs, 1H), 7.58-7.43 (m, 4H), 4.33-4.11 (m, 3H), 3.89 (m, 1H ), 3.70 (dd, 1H), 1.31 (t, 3H).
Synthesestufe 5: (3R*,45,*)-N-(2,3-Dihydro-lH-inden-4-yl)-2-sulfanyliden-4-[3- (trifluormethyl)phenyl]pyrrolidin-3-carboxamid Synthesis step 5: (3R *, 45 , *) - N- (2,3-dihydro-lH-inden-4-yl) -2-sulfanylidene-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxamide
Figure imgf000062_0001
Figure imgf000062_0001
Ethyl-(3/?*,45'*)-2-sulfanyliden -4-[3-(trifluoromethyl)phenyl]pyrrolidin-3- carboxylat (0.45 g, 1.42 mmol, 1.0 equiv) und Indan-4-amin (2.27 g, 17.02 mmol, 10 equiv) wurden 16 Stunden auf 120 °C erhitzt. Nach dem Abkühlen auf Raumtemperatur wurde das im Vakuum eingeengt. Durch Ethyl- (3 /? *, 45 '*) - 2-sulfanylidene -4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxylate (0.45 g, 1.42 mmol, 1.0 equiv) and indan-4-amine (2.27 g, 17.02 mmol, 10 equiv) were heated to 120 ° C for 16 hours. After cooling to room temperature, this was concentrated in vacuo. By
abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte (3R*,45,*)-N-(2,3-Dihydro-lH-inden-4-yl)-2-sulfanyliden-4-[3- (trifluormethyl)phenyl]pyrrolidin-3-carboxamid in Form eines farblosen Feststoffs (0.40 g, 66% der Theorie).‘H-NMR (400 MHz, CDC13 d, ppm) 9.40 (bs, 1H), 7.84 (d, 1H), 7.72 (bs, 1H), 7.56-7.42 (m, 4H), 7.14 (t, 1H), 7.01 (d, 1H), 4.67 (m, 1H), 4.16 (dd, 1H), 3.91 (d, 1H), 3.70 (dd, 1H), 3.01-2.88 (m, 4H), 2.15-2.08 (m, 2H). final column chromatographic purification (gradient ethyl acetate / heptane) of the resulting crude product was able to (3R *, 45 , *) - N- (2,3-dihydro-lH-inden-4-yl) -2-sulfanyliden-4- [3- ( trifluoromethyl) phenyl] pyrrolidine-3-carboxamide in the form of a colorless solid (0.40 g, 66% of theory). 'H-NMR (400 MHz, CDC1 3 d, ppm) 9.40 (bs, 1H), 7.84 (d, 1H ), 7.72 (bs, 1H), 7.56-7.42 (m, 4H), 7.14 (t, 1H), 7.01 (d, 1H), 4.67 (m, 1H), 4.16 (dd, 1H), 3.91 (d, 1H), 3.70 (dd, 1H), 3.01-2.88 (m, 4H), 2.15-2.08 (m, 2H).
Synthesestufe 6: (3R*,45)-N-(2,3-Dihydro-lH-inden-4-yl)-5-(methylsulfanyl)-3-[3- (trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4-carboxamid (Synthesebeispiel No. 1.51-12) Synthesis step 6: (3R *, 45) -N- (2,3-dihydro-lH-inden-4-yl) -5- (methylsulfanyl) -3- [3- (trifluoromethyl) phenyl] -3,4-dihydro -2H-pyrrole-4-carboxamide (Synthesis Example No. 1.51-12)
Figure imgf000062_0002
Figure imgf000062_0002
(3R*,45,*)-N-(2,3-Dihydro-lH-inden-4-yl)-2-sulfanyliden-4-[3-(trifluormethyl)phenyl]pyrrolidin-3- carboxamid (0.35 g, 0.86 mmol, 1.0 equiv), Iodmethan (0.15 g, 1.2 equiv) und Kaliumcarbonat (0.25 g, 2.1 equiv) wurden in Acetonitril (40 ml) suspendiert. Die Suspension wurde anschließend 3 Tage bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde das im Vakuum eingeengt und der Rückstand mit Ethylacetat und Wasser extrahiert. Die organischen Phase über Magnesiumsulfat getrocknet, filtriert und im Vakuum eingeengt. Durch abschließende säulenchromatographische Reinigung (Gradient Essigester/Heptan) des resultierenden Rohproduktes konnte (3R*,45)-N-(2,3-Dihydro-lH-inden-4-yl)-5- (methylsulfanyl)-3-[3-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4-carboxamid in Form eines farblosen Feststoffs (0.157 g, 41% der Theorie). 'H-NMR (400 MHz, CDCh d, ppm) 7.74 (d, 1H), 7.54- 7.40 (m, 4H), 7.18-7.14 (m, 2H), 7.05 (d, 1H), 4.50 (dd, 1H), 4.25 (m, 1H), 3.99 (dd, 1H), 3.72 (d, 1H), 2.95 (t, 2H), 2.84-2.78 (m, 2H), 2.58 (s, 3H), 2.13-2.09 (m, 2H). In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von substituierten 5-(Sulfanyl)- 3,4-dihydro-2H-pyrrol-4-carboxamide erhält man die nachfolgend genannten Verbindungen: (3R *, 45 , *) - N- (2,3-dihydro-lH-inden-4-yl) -2-sulfanyliden-4- [3- (trifluoromethyl) phenyl] pyrrolidine-3-carboxamide (0.35 g, 0.86 mmol, 1.0 equiv), iodomethane (0.15 g, 1.2 equiv) and potassium carbonate (0.25 g, 2.1 equiv) were suspended in acetonitrile (40 ml). The suspension was then stirred for 3 days at room temperature. The reaction mixture was concentrated in vacuo and the residue extracted with ethyl acetate and water. The organic phase dried over magnesium sulfate, filtered and concentrated in vacuo. By final column chromatography purification (gradient ethyl acetate / heptane) of the resulting crude product, (3R *, 45) -N- (2,3-dihydro-lH-inden-4-yl) -5- (methylsulfanyl) -3- [3- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide in the form of a colorless solid (0.157 g, 41% of theory). 'H NMR (400 MHz, CDCh d, ppm) 7.74 (d, 1H), 7.54-7.40 (m, 4H), 7.18-7.14 (m, 2H), 7.05 (d, 1H), 4.50 (dd, 1H) ), 4.25 (m, 1H), 3.99 (dd, 1H), 3.72 (d, 1H), 2.95 (t, 2H), 2.84-2.78 (m, 2H), 2.58 (s, 3H), 2.13-2.09 ( m, 2H). The following compounds are obtained analogously to the preparation examples given above and recited at the appropriate place and taking into account the general information on the preparation of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides:
Figure imgf000063_0001
Tabelle 1.1 : Bevorzugte Verbindungen der Formel (1.1) sind die Verbindungen 1.1-1 bis 1.1-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.1-1 bis 1.1-247 der Tabelle 1.1 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der Tabelle 1 definiert.
Figure imgf000063_0001
Table 1.1: Preferred compounds of the formula (1.1) are the compounds 1.1-1 to 1.1-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.1-1 to 1.1-247 of table 1.1 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1.
Tabelle 1 :  Table 1 :
Figure imgf000063_0002
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0002
Figure imgf000063_0002
Figure imgf000064_0001
Figure imgf000065_0001
Figure imgf000066_0001
Figure imgf000067_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000070_0002
Figure imgf000070_0001
Tabelle 1.2: Bevorzugte Verbindungen der Formel (1.2) sind die Verbindungen 1.2-1 bis 1.2-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.2-1 bis 1.2-247 der Tabelle 1.2 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000070_0001
Table 1.2: Preferred compounds of the formula (1.2) are the compounds 1.2-1 to 1.2-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.2-1 to 1.2-247 of table 1.2 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000071_0001
Figure imgf000071_0001
Tabelle 1.3: Bevorzugte Verbindungen der Formel (1.3) sind die Verbindungen 1.3-1 bis 1.3-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.3-1 bis 1.3-247 der Tabelle 1.3 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der Tabelle 1 definiert. Table 1.3: Preferred compounds of the formula (1.3) are the compounds 1.3-1 to 1.3-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.3-1 to 1.3-247 of table 1.3 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1.
Figure imgf000071_0002
Figure imgf000071_0002
Tabelle 1.4: Bevorzugte Verbindungen der Formel (1.4) sind die Verbindungen 1.4-1 bis 1.4-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.4-1 bis 1.4-247 der Tabelle 1.4 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.4-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.4-1 to 1.4-247 of table 1.4 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
Figure imgf000071_0003
Tabelle 1.5: Bevorzugte Verbindungen der Formel (1.5) sind die Verbindungen 1.5-1 bis 1.5-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.5-1 bis 1.5-247 der Tabelle 1.5 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000071_0003
Table 1.5: Preferred compounds of the formula (1.5) are the compounds 1.5-1 to 1.5-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.5-1 to 1.5-247 of table 1.5 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000072_0001
Figure imgf000072_0001
Tabelle 1.6: Bevorzugte Verbindungen der Formel (1.6) sind die Verbindungen 1.6-1 bis 1.6-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.6-1 bis 1.6-247 der Tabelle 1.6 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.6: Preferred compounds of the formula (1.6) are the compounds 1.6-1 to 1.6-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.6-1 to 1.6-247 of table 1.6 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000072_0002
Figure imgf000072_0002
Tabelle 1.7: Bevorzugte Verbindungen der Formel (1.7) sind die Verbindungen 1.7-1 bis 1.7-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.7-1 bis 1.7-247 der Tabelle 1.7 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.7: Preferred compounds of the formula (1.7) are the compounds 1.7-1 to 1.7-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.7-1 to 1.7-247 of table 1.7 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000073_0001
Figure imgf000073_0001
Tabelle 1.8: Bevorzugte Verbindungen der Formel (1.8) sind die Verbindungen 1.8-1 bis 1.8-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.8-1 bis 1.8-247 der Tabelle 1.8 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.8-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.8-1 to 1.8-247 in Table 1.8 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000073_0002
Tabelle 1.9: Bevorzugte Verbindungen der Formel (1.9) sind die Verbindungen 1.9-1 bis 1.9-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.9-1 bis 1.9-247 der Tabelle 1.9 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000073_0002
Table 1.9: Preferred compounds of the formula (1.9) are the compounds 1.9-1 to 1.9-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.9-1 to 1.9-247 of table 1.9 are thus by the meaning of the respective entries no. 1 to 247 defined for Q of Table 1 above.
Figure imgf000073_0003
Figure imgf000073_0003
Tabelle 1.10: Bevorzugte Verbindungen der Formel (1.10) sind die Verbindungen 1.10-1 bis 1.10-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.10-1 bis 1.10-247 der Tabelle 1.10 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.10-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.10-1 to 1.10-247 of table 1.10 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000074_0001
Figure imgf000074_0001
Tabelle 1.11: Bevorzugte Verbindungen der Formel (1.11) sind die Verbindungen 1.11-1 bis 1.11-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.11-1 bis 1.11-247 der Tabelle 1.11 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.11: Preferred compounds of the formula (1.11) are the compounds 1.11-1 to 1.11-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.11-1 to 1.11-247 of table 1.11 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000074_0002
Tabelle 1.12: Bevorzugte Verbindungen der Formel (1.12) sind die Verbindungen 1.12-1 bis 1.12-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.12-1 bis 1.12-247 der Tabelle 1.12 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000074_0002
Table 1.12: Preferred compounds of the formula (1.12) are the compounds 1.12-1 to 1.12-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.12-1 to 1.12-247 of table 1.12 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000074_0003
Figure imgf000074_0003
Tabelle 1.13: Bevorzugte Verbindungen der Formel (1.13) sind die Verbindungen 1.13-1 bis 1.13-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.13-1 bis 1.13-247 der Tabelle 1.13 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000075_0001
Table 1.13: Preferred compounds of the formula (1.13) are the compounds 1.13-1 to 1.13-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.13-1 to 1.13-247 of table 1.13 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000075_0001
Tabelle 1.14: Bevorzugte Verbindungen der Formel (1.14) sind die Verbindungen 1.14-1 bis 1.14-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.14-1 bis 1.14-247 der Tabelle 1.14 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.14: Preferred compounds of the formula (1.14) are the compounds 1.14-1 to 1.14-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.14-1 to 1.14-247 of table 1.14 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000075_0002
Tabelle 1.15: Bevorzugte Verbindungen der Formel (1.15) sind die Verbindungen 1.15-1 bis 1.15-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.15-1 bis 1.15-247 der Tabelle 1.15 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000075_0002
Table 1.15: Preferred compounds of the formula (1.15) are the compounds 1.15-1 to 1.15-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.15-1 to 1.15-247 of table 1.15 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000075_0003
Figure imgf000075_0003
Tabelle 1.16: Bevorzugte Verbindungen der Formel (1.16) sind die Verbindungen 1.16-1 bis 1.16-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.16-1 bis 1.16-247 der Tabelle 1.16 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.16-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.16-1 to 1.16-247 of table 1.16 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000076_0001
Figure imgf000076_0001
Tabelle 1.17: Bevorzugte Verbindungen der Formel (1.17) sind die Verbindungen 1.17-1 bis 1.17-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.17-1 bis 1.17-247 der Tabelle 1.17 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.17: Preferred compounds of the formula (1.17) are the compounds 1.17-1 to 1.17-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.17-1 to 1.17-247 of table 1.17 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000076_0002
Figure imgf000076_0002
Tabelle 1.18: Bevorzugte Verbindungen der Formel (1.18) sind die Verbindungen 1.18-1 bis 1.18-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.18-1 bis 1.18-247 der Tabelle 1.18 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.18: Preferred compounds of the formula (1.18) are the compounds 1.18-1 to 1.18-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.18-1 to 1.18-247 of table 1.18 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000076_0003
Tabelle 1.19: Bevorzugte Verbindungen der Formel (1.19) sind die Verbindungen 1.19-1 bis 1.19-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.19-1 bis 1.19-247 der Tabelle 1.19 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000076_0003
Table 1.19: Preferred compounds of the formula (1.19) are the compounds 1.19-1 to 1.19-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.19-1 to 1.19-247 of table 1.19 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000077_0001
Figure imgf000077_0001
Tabelle 1.20: Bevorzugte Verbindungen der Formel (1.20) sind die Verbindungen 1.20-1 bis 1.20-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.20-1 bis 1.20-247 der Tabelle 1.20 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.20: Preferred compounds of the formula (1.20) are the compounds 1.20-1 to 1.20-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.20-1 to 1.20-247 of table 1.20 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000077_0002
Tabelle 1.21 : Bevorzugte Verbindungen der Formel (1.21) sind die Verbindungen 1.21-1 bis 1.21-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.21-1 bis 1.21-247 der Tabelle 1.21 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000077_0002
Table 1.21: Preferred compounds of the formula (1.21) are the compounds 1.21-1 to 1.21-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.21-1 to 1.21-247 of table 1.21 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000077_0003
Tabelle 1.22: Bevorzugte Verbindungen der Formel (1.22) sind die Verbindungen 1.22-1 bis 1.22-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen
Figure imgf000077_0003
Table 1.22: Preferred compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-247, in which Q has the meanings of Table 1 given in the respective row. The connections
1.22-1 bis 1.22-247 der Tabelle 1.22 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. 1.22-1 to 1.22-247 of table 1.22 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000078_0001
Figure imgf000078_0001
Tabelle 1.23: Bevorzugte Verbindungen der Formel (1.23) sind die Verbindungen 1.23-1 bis 1.23-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.23: Preferred compounds of the formula (1.23) are the compounds 1.23-1 to 1.23-247, in which Q has the meanings of Table 1 given in the respective row. The connections
1.23-1 bis 1.23-247 der Tabelle 1.23 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. 1.23-1 to 1.23-247 of table 1.23 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000078_0002
Figure imgf000078_0002
Tabelle 1.24: Bevorzugte Verbindungen der Formel (1.24) sind die Verbindungen 1.24-1 bis 1.24-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.24: Preferred compounds of the formula (1.24) are the compounds 1.24-1 to 1.24-247, in which Q has the meanings of Table 1 given in the respective row. The connections
1.24-1 bis 1.24-247 der Tabelle 1.24 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000079_0001
1.24-1 to 1.24-247 of table 1.24 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000079_0001
Tabelle 1.25: Bevorzugte Verbindungen der Formel (1.25) sind die Verbindungen 1.25-1 bis 1.25-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.25-1 bis 1.25-247 der Tabelle 1.25 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.25: Preferred compounds of the formula (1.25) are the compounds 1.25-1 to 1.25-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.25-1 to 1.25-247 of table 1.25 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000079_0002
Tabelle 1.26: Bevorzugte Verbindungen der Formel (1.26) sind die Verbindungen 1.26-1 bis 1.26-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.26-1 bis 1.26-247 der Tabelle 1.26 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000079_0002
Table 1.26: Preferred compounds of the formula (1.26) are the compounds 1.26-1 to 1.26-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.26-1 to 1.26-247 of table 1.26 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000079_0003
Figure imgf000079_0003
Tabelle 1.27: Bevorzugte Verbindungen der Formel (1.27) sind die Verbindungen 1.27-1 bis 1.27-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.27-1 bis 1.27-247 der Tabelle 1.27 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.27: Preferred compounds of the formula (1.27) are the compounds 1.27-1 to 1.27-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.27-1 to 1.27-247 of table 1.27 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000080_0001
Figure imgf000080_0001
Tabelle 1.28: Bevorzugte Verbindungen der Formel (1.28) sind die Verbindungen 1.28-1 bis 1.28-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.28-1 bis 1.28-247 der Tabelle 1.28 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.28-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.28-1 to 1.28-247 of table 1.28 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000080_0002
Figure imgf000080_0002
Tabelle 1.29: Bevorzugte Verbindungen der Formel (1.29) sind die Verbindungen 1.29-1 bis 1.29-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.29-1 bis 1.29-247 der Tabelle 1.29 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.29: Preferred compounds of the formula (1.29) are the compounds 1.29-1 to 1.29-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.29-1 to 1.29-247 of table 1.29 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000080_0003
(1-30) Tabelle 1.30: Bevorzugte Verbindungen der Formel (1.30) sind die Verbindungen 1.30-1 bis 1.30-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.30-1 bis 1.30-247 der Tabelle 1.30 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000080_0003
(1-30) Table 1.30: Preferred compounds of the formula (1.30) are the compounds 1.30-1 to 1.30-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.30-1 to 1.30-247 of table 1.30 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000081_0001
Figure imgf000081_0001
Tabelle 1.31 : Bevorzugte Verbindungen der Formel (1.31) sind die Verbindungen 1.31-1 bis 1.31-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.31-1 bis 1.31-247 der Tabelle 1.31 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.31: Preferred compounds of the formula (1.31) are the compounds 1.31-1 to 1.31-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.31-1 to 1.31-247 of table 1.31 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000081_0002
Figure imgf000081_0002
Tabelle 1.32: Bevorzugte Verbindungen der Formel (1.32) sind die Verbindungen 1.32-1 bis 1.32-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.32-1 bis 1.32-247 der Tabelle 1.32 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.32: Preferred compounds of the formula (1.32) are the compounds 1.32-1 to 1.32-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.32-1 to 1.32-247 of table 1.32 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000081_0003
Tabelle 1.33: Bevorzugte Verbindungen der Formel (1.33) sind die Verbindungen 1.33-1 bis 1.33-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.33-1 bis 1.33-247 der Tabelle 1.33 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000081_0003
Table 1.33: Preferred compounds of the formula (1.33) are the compounds 1.33-1 to 1.33-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.33-1 to 1.33-247 of table 1.33 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000082_0001
Figure imgf000082_0001
Tabelle 1.34: Bevorzugte Verbindungen der Formel (1.34) sind die Verbindungen 1.34-1 bis 1.34-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.34-1 bis 1.34-247 der Tabelle 1.34 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.34-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.34-1 to 1.34-247 of table 1.34 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000082_0002
Figure imgf000082_0002
Tabelle 1.35: Bevorzugte Verbindungen der Formel (1.35) sind die Verbindungen 1.35-1 bis 1.35-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.35-1 bis 1.35-247 der Tabelle 1.35 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.35: Preferred compounds of the formula (1.35) are the compounds 1.35-1 to 1.35-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.35-1 to 1.35-247 in table 1.35 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000082_0003
Tabelle 1.36: Bevorzugte Verbindungen der Formel (1.36) sind die Verbindungen 1.36-1 bis 1.36-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.36-1 bis 1.36-247 der Tabelle 1.36 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000082_0003
Table 1.36: Preferred compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.36-1 to 1.36-247 of table 1.36 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000083_0001
Figure imgf000083_0001
Tabelle 1.37: Bevorzugte Verbindungen der Formel (1.37) sind die Verbindungen 1.37-1 bis 1.37-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.37-1 bis 1.37-247 der Tabelle 1.37 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.37: Preferred compounds of the formula (1.37) are the compounds 1.37-1 to 1.37-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.37-1 to 1.37-247 of table 1.37 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000083_0002
Figure imgf000083_0002
Tabelle 1.38: Bevorzugte Verbindungen der Formel (1.38) sind die Verbindungen 1.38-1 bis 1.38-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.38-1 bis 1.38-247 der Tabelle 1.38 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.38: Preferred compounds of the formula (1.38) are the compounds 1.38-1 to 1.38-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.38-1 to 1.38-247 of table 1.38 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000083_0003
Figure imgf000083_0003
Tabelle 1.39: Bevorzugte Verbindungen der Formel (1.39) sind die Verbindungen 1.39-1 bis 1.39-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.39-1 bis 1.39-247 der Tabelle 1.39 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.39: Preferred compounds of the formula (1.39) are the compounds 1.39-1 to 1.39-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.39-1 to 1.39-247 of table 1.39 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000084_0001
Figure imgf000084_0001
Tabelle 1.40: Bevorzugte Verbindungen der Formel (1.40) sind die Verbindungen 1.40-1 bis 1.40-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.40-1 bis 1.40-247 der Tabelle 1.40 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 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 1.40-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.40-1 to 1.40-247 of table 1.40 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000084_0002
Figure imgf000084_0002
Tabelle 1.41 : Bevorzugte Verbindungen der Formel (1.41) sind die Verbindungen 1.41-1 bis 1.41-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.41-1 bis 1.41-247 der Tabelle 1.41 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.41: Preferred compounds of the formula (1.41) are the compounds 1.41-1 to 1.41-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.41-1 to 1.41-247 of table 1.41 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000084_0003
Tabelle 1.42: Bevorzugte Verbindungen der Formel (1.42) sind die Verbindungen 1.42-1 bis 1.42-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.42-1 bis 1.42-247 der Tabelle 1.42 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000084_0003
Table 1.42: Preferred compounds of the formula (1.42) are the compounds 1.42-1 to 1.42-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.42-1 to 1.42-247 in table 1.42 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000085_0001
Figure imgf000085_0001
Tabelle 1.43: Bevorzugte Verbindungen der Formel (1.43) sind die Verbindungen 1.43-1 bis 1.43-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.43-1 bis 1.43-247 der Tabelle 1.43 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.43: Preferred compounds of the formula (1.43) are the compounds 1.43-1 to 1.43-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.43-1 to 1.43-247 of table 1.43 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000085_0002
Tabelle 1.44: Bevorzugte Verbindungen der Formel (1.44) sind die Verbindungen 1.44-1 bis 1.44-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.44-1 bis 1.44-247 der Tabelle 1.44 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000085_0002
Table 1.44: Preferred compounds of the formula (1.44) are the compounds 1.44-1 to 1.44-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.44-1 to 1.44-247 of table 1.44 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000085_0003
Tabelle 1.45: Bevorzugte Verbindungen der Formel (1.45) sind die Verbindungen 1.45-1 bis 1.45-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.45-1 bis 1.45-247 der Tabelle 1.45 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000085_0003
Table 1.45: Preferred compounds of the formula (1.45) are the compounds 1.45-1 to 1.45-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.45-1 to 1.45-247 in table 1.45 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000086_0001
Figure imgf000086_0001
Tabelle 1.46: Bevorzugte Verbindungen der Formel (1.46) sind die Verbindungen 1.46-1 bis 1.46-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.46-1 bis 1.46-247 der Tabelle 1.46 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.46: Preferred compounds of the formula (1.46) are the compounds 1.46-1 to 1.46-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.46-1 to 1.46-247 in table 1.46 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000086_0002
Tabelle 1.47: Bevorzugte Verbindungen der Formel (1.47) sind die Verbindungen 1.47-1 bis 1.47-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.47-1 bis 1.47-247 der Tabelle 1.47 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000086_0002
Table 1.47: Preferred compounds of the formula (1.47) are the compounds 1.47-1 to 1.47-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.47-1 to 1.47-247 of table 1.47 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000086_0003
Tabelle 1.48: Bevorzugte Verbindungen der Formel (1.48) sind die Verbindungen 1.48-1 bis 1.48-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.48-1 bis 1.48-247 der Tabelle 1.48 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000086_0003
Table 1.48: Preferred compounds of the formula (1.48) are the compounds 1.48-1 to 1.48-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.48-1 to 1.48-247 of table 1.48 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000087_0001
Figure imgf000087_0001
Tabelle 1.49: Bevorzugte Verbindungen der Formel (1.49) sind die Verbindungen 1.49-1 bis 1.49-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.49-1 bis 1.49-247 der Tabelle 1.49 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.49: Preferred compounds of the formula (1.49) are the compounds 1.49-1 to 1.49-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.49-1 to 1.49-247 of table 1.49 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000087_0002
Tabelle 1.50: Bevorzugte Verbindungen der Formel (1.50) sind die Verbindungen 1.50-1 bis 1.50-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.50-1 bis 1.50-247 der Tabelle 1.50 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000087_0002
Table 1.50: Preferred compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.50-1 to 1.50-247 of table 1.50 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000087_0003
Tabelle 1.51 : Bevorzugte Verbindungen der Formel (1.51) sind die Verbindungen 1.51-1 bis 1.51-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.51-1 bis 1.51-247 der Tabelle 1.51 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000087_0003
Table 1.51: Preferred compounds of the formula (1.51) are the compounds 1.51-1 to 1.51-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.51-1 to 1.51-247 of table 1.51 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000088_0001
Figure imgf000088_0001
Tabelle 1.52: Bevorzugte Verbindungen der Formel (1.52) sind die Verbindungen 1.52-1 bis 1.52-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.52-1 bis 1.52-247 der Tabelle 1.52 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.52: Preferred compounds of the formula (1.52) are the compounds 1.52-1 to 1.52-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.52-1 to 1.52-247 of table 1.52 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000088_0002
Tabelle 1.53: Bevorzugte Verbindungen der Formel (1.53) sind die Verbindungen 1.53-1 bis 1.53-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.53-1 bis 1.53-247 der Tabelle 1.53 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000088_0002
Table 1.53: Preferred compounds of the formula (1.53) are the compounds 1.53-1 to 1.53-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.53-1 to 1.53-247 of table 1.53 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000088_0003
Tabelle 1.54: Bevorzugte Verbindungen der Formel (1.54) sind die Verbindungen 1.54-1 bis 1.54-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.54-1 bis 1.54-247 der Tabelle 1.54 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000088_0003
Table 1.54: Preferred compounds of the formula (1.54) are the compounds 1.54-1 to 1.54-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.54-1 to 1.54-247 of table 1.54 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000089_0001
Figure imgf000089_0001
Tabelle 1.55: Bevorzugte Verbindungen der Formel (1.55) sind die Verbindungen 1.55-1 bis 1.55-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.55-1 bis 1.55-247 der Tabelle 1.55 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.55: Preferred compounds of the formula (1.55) are the compounds 1.55-1 to 1.55-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.55-1 to 1.55-247 of table 1.55 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000089_0002
Tabelle 1.56: Bevorzugte Verbindungen der Formel (1.56) sind die Verbindungen 1.56-1 bis 1.56-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.56-1 bis 1.56-247 der Tabelle 1.56 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000090_0001
Figure imgf000089_0002
Table 1.56: Preferred compounds of the formula (1.56) are the compounds 1.56-1 to 1.56-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.56-1 to 1.56-247 of table 1.56 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000090_0001
Tabelle 1.57: Bevorzugte Verbindungen der Formel (1.57) sind die Verbindungen 1.57-1 bis 1.57-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.57-1 bis 1.57-247 der Tabelle 1.57 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.57: Preferred compounds of the formula (1.57) are the compounds 1.57-1 to 1.57-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.57-1 to 1.57-247 of table 1.57 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000090_0002
Tabelle 1.58: Bevorzugte Verbindungen der Formel (1.58) sind die Verbindungen 1.58-1 bis 1.58-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.58-1 bis 1.58-247 der Tabelle 1.58 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000090_0002
Table 1.58: Preferred compounds of the formula (1.58) are the compounds 1.58-1 to 1.58-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.58-1 to 1.58-247 of table 1.58 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000090_0003
Figure imgf000090_0003
(1-59)  (1-59)
Tabelle 1.59: Bevorzugte Verbindungen der Formel (1.59) sind die Verbindungen 1.59-1 bis 1.59-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.59-1 bis 1.59-247 der Tabelle 1.59 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.59: Preferred compounds of the formula (1.59) are the compounds 1.59-1 to 1.59-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.59-1 to 1.59-247 of table 1.59 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000091_0001
Figure imgf000091_0001
Tabelle 1.60: Bevorzugte Verbindungen der Formel (1.60) sind die Verbindungen 1.60-1 bis 1.60-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.60-1 bis 1.60-247 der Tabelle 1.60 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.60: Preferred compounds of the formula (1.60) are the compounds 1.60-1 to 1.60-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.60-1 to 1.60-247 of table 1.60 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000091_0002
Figure imgf000091_0002
Tabelle 1.61 : Bevorzugte Verbindungen der Formel (1.61) sind die Verbindungen 1.61-1 bis 1.61-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.61-1 bis 1.61-247 der Tabelle 1.61 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.61: Preferred compounds of the formula (1.61) are the compounds 1.61-1 to 1.61-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.61-1 to 1.61-247 of table 1.61 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000091_0003
Tabelle 1.62: Bevorzugte Verbindungen der Formel (1.62) sind die Verbindungen 1.62-1 bis 1.62-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.62-1 bis 1.62-247 der Tabelle 1.62 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000091_0003
Table 1.62: Preferred compounds of the formula (1.62) are the compounds 1.62-1 to 1.62-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.62-1 to 1.62-247 of table 1.62 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000092_0001
Figure imgf000092_0001
Tabelle 1.63: Bevorzugte Verbindungen der Formel (1.63) sind die Verbindungen 1.63-1 bis 1.63-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.63-1 bis 1.63-247 der Tabelle 1.63 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.63: Preferred compounds of the formula (1.63) are the compounds 1.63-1 to 1.63-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.63-1 to 1.63-247 of table 1.63 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000092_0002
Tabelle 1.64: Bevorzugte Verbindungen der Formel (1.64) sind die Verbindungen 1.64-1 bis 1.64-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.64-1 bis 1.64-247 der Tabelle 1.64 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000092_0002
Table 1.64: Preferred compounds of the formula (1.64) are the compounds 1.64-1 to 1.64-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.64-1 to 1.64-247 of table 1.64 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000092_0003
Tabelle 1.65: Bevorzugte Verbindungen der Formel (1.65) sind die Verbindungen 1.65-1 bis 1.65-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.65-1 bis 1.65-247 der Tabelle 1.65 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000092_0003
Table 1.65: Preferred compounds of the formula (1.65) are the compounds 1.65-1 to 1.65-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.65-1 to 1.65-247 of table 1.65 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000093_0001
Figure imgf000093_0001
Tabelle 1.66: Bevorzugte Verbindungen der Formel (1.66) sind die Verbindungen 1.66-1 bis 1.66-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.66-1 bis 1.66-247 der Tabelle 1.66 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.66: Preferred compounds of the formula (1.66) are the compounds 1.66-1 to 1.66-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.66-1 to 1.66-247 of table 1.66 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000093_0002
Tabelle 1.67: Bevorzugte Verbindungen der Formel (1.67) sind die Verbindungen 1.67-1 bis 1.67-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.67-1 bis 1.67-247 der Tabelle 1.67 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000093_0002
Table 1.67: Preferred compounds of the formula (1.67) are the compounds 1.67-1 to 1.67-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.67-1 to 1.67-247 of table 1.67 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000094_0001
Figure imgf000094_0001
Tabelle 1.68: Bevorzugte Verbindungen der Formel (1.68) sind die Verbindungen 1.68-1 bis 1.68-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.68-1 bis 1.68-247 der Tabelle 1.68 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.68: Preferred compounds of the formula (1.68) are the compounds 1.68-1 to 1.68-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.68-1 to 1.68-247 of table 1.68 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000094_0002
Tabelle 1.69: Bevorzugte Verbindungen der Formel (1.69) sind die Verbindungen 1.69-1 bis 1.69-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.69-1 bis 1.69-247 der Tabelle 1.69 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000094_0002
Table 1.69: Preferred compounds of the formula (1.69) are the compounds 1.69-1 to 1.69-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.69-1 to 1.69-247 of table 1.69 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000094_0003
Figure imgf000094_0003
Tabelle 1.70: Bevorzugte Verbindungen der Formel (1.70) sind die Verbindungen 1.70-1 bis 1.70-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.70-1 bis 1.70-247 der Tabelle 1.70 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.70: Preferred compounds of the formula (1.70) are the compounds 1.70-1 to 1.70-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.70-1 to 1.70-247 of table 1.70 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000095_0001
Figure imgf000095_0001
Tabelle 1.71 : Bevorzugte Verbindungen der Formel (1.71) sind die Verbindungen 1.71-1 bis 1.71-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.71-1 bis 1.71-247 der Tabelle 1.71 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.71: Preferred compounds of the formula (1.71) are the compounds 1.71-1 to 1.71-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.71-1 to 1.71-247 of table 1.71 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000095_0002
Figure imgf000095_0002
Tabelle 1.72: Bevorzugte Verbindungen der Formel (1.72) sind die Verbindungen 1.72-1 bis 1.72-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.72-1 bis 1.72-247 der Tabelle 1.72 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.72: Preferred compounds of the formula (1.72) are the compounds 1.72-1 to 1.72-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.72-1 to 1.72-247 in table 1.72 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000095_0003
Figure imgf000095_0003
Tabelle 1.73: Bevorzugte Verbindungen der Formel (1.73) sind die Verbindungen 1.73-1 bis 1.73-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.73-1 bis 1.73-247 der Tabelle 1.73 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.73: Preferred compounds of the formula (1.73) are the compounds 1.73-1 to 1.73-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.73-1 to 1.73-247 of table 1.73 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000096_0001
Tabelle 1.74: Bevorzugte Verbindungen der Formel (1.74) sind die Verbindungen 1.74-1 bis 1.74-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen
Figure imgf000096_0001
Table 1.74: Preferred compounds of the formula (1.74) are the compounds 1.74-1 to 1.74-247, in which Q has the meanings of Table 1 given in the respective row. The connections
1.74-1 bis 1.74-247 der Tabelle 1.74 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. 1.74-1 to 1.74-247 of table 1.74 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000096_0002
Figure imgf000096_0002
Tabelle 1.75: Bevorzugte Verbindungen der Formel (1.75) sind die Verbindungen 1.75-1 bis 1.75-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die VerbindungenTable 1.75: Preferred compounds of the formula (1.75) are the compounds 1.75-1 to 1.75-247, in which Q has the meanings of Table 1 given in the respective row. The connections
1.75-1 bis 1.75-247 der Tabelle 1.75 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. 1.75-1 to 1.75-247 of table 1.75 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000096_0003
Tabelle 1.76: Bevorzugte Verbindungen der Formel (1.76) sind die Verbindungen 1.76-1 bis 1.76-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.76-1 bis 1.76-247 der Tabelle 1.76 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000096_0003
Table 1.76: Preferred compounds of the formula (1.76) are the compounds 1.76-1 to 1.76-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.76-1 to 1.76-247 of table 1.76 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000097_0001
Figure imgf000097_0001
Tabelle 1.77: Bevorzugte Verbindungen der Formel (1.77) sind die Verbindungen 1.77-1 bis 1.77-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.77-1 bis 1.77-247 der Tabelle 1.77 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.77: Preferred compounds of the formula (1.77) are the compounds 1.77-1 to 1.77-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.77-1 to 1.77-247 of table 1.77 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000097_0002
Tabelle 1.78: Bevorzugte Verbindungen der Formel (1.78) sind die Verbindungen 1.78-1 bis 1.78-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.78-1 bis 1.78-247 der Tabelle 1.78 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000097_0002
Table 1.78: Preferred compounds of the formula (1.78) are the compounds 1.78-1 to 1.78-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.78-1 to 1.78-247 of table 1.78 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000098_0001
Figure imgf000098_0001
Tabelle 1.79: Bevorzugte Verbindungen der Formel (1.79) sind die Verbindungen 1.79-1 bis 1.79-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.79-1 bis 1.79-247 der Tabelle 1.79 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bisTable 1.79: Preferred compounds of the formula (1.79) are the compounds 1.79-1 to 1.79-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.79-1 to 1.79-247 of table 1.79 are thus by the meaning of the respective entries No. 1 to
247 für Q der oben stehenden Tabelle 1 definiert. 247 for Q of Table 1 above.
Figure imgf000098_0002
Tabelle 1.80: Bevorzugte Verbindungen der Formel (1.80) sind die Verbindungen 1.80-1 bis 1.80-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.80-1 bis 1.80-247 der Tabelle 1.80 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert.
Figure imgf000098_0002
Table 1.80: Preferred compounds of the formula (1.80) are the compounds 1.80-1 to 1.80-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.80-1 to 1.80-247 of table 1.80 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000098_0003
Figure imgf000098_0003
(1-81 )  (1-81)
Tabelle 1.81 : Bevorzugte Verbindungen der Formel (1.81) sind die Verbindungen 1.81-1 bis 1.81-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.81-1 bis 1.81-247 der Tabelle 1.81 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.81: Preferred compounds of the formula (1.81) are the compounds 1.81-1 to 1.81-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.81-1 to 1.81-247 of table 1.81 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Figure imgf000099_0001
Figure imgf000099_0001
Tabelle 1.82: Bevorzugte Verbindungen der Formel (1.82) sind die Verbindungen 1.82-1 bis 1.82-247, worin Q die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 hat. Die Verbindungen 1.82-1 bis 1.82-247 der Tabelle 1.82 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 247 für Q der oben stehenden Tabelle 1 definiert. Table 1.82: Preferred compounds of the formula (1.82) are the compounds 1.82-1 to 1.82-247, in which Q has the meanings of Table 1 given in the respective row. The connections 1.82-1 to 1.82-247 in table 1.82 are thus by the meaning of the respective entries No. 1 to 247 defined for Q of Table 1 above.
Spektroskopische Daten ausgewählter Tabellenbeispiele: Spectroscopic data from selected table examples:
Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formeln (1) sind im Folgenden aufgeführt. 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 CDCF, CD3OD oder de- DM SO, interner Standard: Tetramethylsilan d = 0.00 ppm), wurden mit einem Gerät der Firma Broker erhalten, und die bezeichneten Signale haben die nachfolgend aufgeführten Bedeutungen: br = breit(es); s = Singulett, d = Dublett, t = Triplett, dd = Doppeldublett, ddd = Dublett eines Doppeldubletts, m = Multiplett, q = Quartett, quint = Quintett, sext = Sextett, sept = Septett, 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. Selected detailed synthesis examples for the compounds of the general formulas (1) according to the invention are listed 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 CDCF, CD3OD or de- DM SO, internal standard: tetramethylsilane d = 0.00 ppm) were obtained with a Broker device, and the signals indicated have the meanings given below: br = broad (es); 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.
Die nachfolgend aufgeführten spektroskopischen Daten ausgewählter Tabellenbeispiele wurden über klassische H-NMR-Intcrprctation oder über NMR-Peak-Listenverfahren ausgewertet. Klassische H-NMR-Intcrprctation Beispiel Nr. 1.5-13: The spectroscopic data of selected table examples listed below were evaluated using classic H-NMR interpretation or using NMR peak list methods. Classic H-NMR interpretation Example No. 1.5-13:
‘H-NMR (400 MHz, CDC13 d, ppm): 8.06 (t, 1H), 7.59 (d, 2H), 7.33 (d, 2H), 7.11-7.03 (m, 1H), 7.00- 6.92 (m, 1H), 4.51 (ddd, 1H), 4.22 (m, 1H), 4.01 (dd, 1H), 3.76 (d, 1H), 2.58 (s, 3H). 'H NMR (400 MHz, CDC1 3 d, ppm): 8.06 (t, 1H), 7.59 (d, 2H), 7.33 (d, 2H), 7.11-7.03 (m, 1H), 7.00-6.92 (m , 1H), 4.51 (ddd, 1H), 4.22 (m, 1H), 4.01 (dd, 1H), 3.76 (d, 1H), 2.58 (s, 3H).
Beispiel Nr. 1.5-12: Example No. 1.5-12:
1H-NMR (400 MHz, CDCI3 d, ppm): 8.06 (t, 1H), 7.59-7.41 (m, 5H), 7.08 (dq, 1H), 6.94 (q, 1H), 4.52 (ddd, 1H), 4.22 (m, 1H), 4.01 (dd, 1H), 3.78 (d, 1H), 2.58 (s, 3H). 1 H NMR (400 MHz, CDCI 3 d, ppm): 8.06 (t, 1H), 7.59-7.41 (m, 5H), 7.08 (dq, 1H), 6.94 (q, 1H), 4.52 (ddd, 1H ), 4.22 (m, 1H), 4.01 (dd, 1H), 3.78 (d, 1H), 2.58 (s, 3H).
Beispiel Nr. 1.2-12: Example No. 1.2-12:
1H-NMR (400 MHz, CDCI3 d, ppm): 8.31 (t, 1H), 7.59-7.39 (m, 6H), 7.18-7.07 (m, 2H), 4.52 (ddd, 1H), 4.39 (m, 1H), 4.01 (dd, 1H), 3.78 (d, 1H), 2.57 (s, 3H). 1 H-NMR (400 MHz, CDCI 3 d, ppm): 8.31 (t, 1H), 7.59-7.39 (m, 6H), 7.18-7.07 (m, 2H), 4.52 (ddd, 1H), 4.39 (m , 1H), 4.01 (dd, 1H), 3.78 (d, 1H), 2.57 (s, 3H).
Beispiel Nr. 1.6-13: Example No. 1.6-13:
1H-NMR (400 MHz, CDCI3 d, ppm): 7.99 (m, 1H), 7.60 (d, 2H), 7.43 (m, 1H, NH), 7.33 (d, 2H), 6.98 1 H NMR (400 MHz, CDCI 3 d, ppm): 7.99 (m, 1H), 7.60 (d, 2H), 7.43 (m, 1H, NH), 7.33 (d, 2H), 6.98
(m, 1H), 4.50 (ddd, 1H), 4.22 (m, 1H), 4.02 (dd, 1H), 3.75 (d, 1H), 2.58 (s, 3H). (m, 1H), 4.50 (ddd, 1H), 4.22 (m, 1H), 4.02 (dd, 1H), 3.75 (d, 1H), 2.58 (s, 3H).
Beispiel Nr. 1.2-13: Example No. 1.2-13:
‘H-NMR (400 MHz, CDCI3 d, ppm): 8.31 (t, 1H), 7.59 (d, 2H), 7.34 (d, 2H), 7.18-6.95 (m, 4H), 4.53 (ddd, 1H), 4.22 (m, 1H), 4.02 (dd, 1H), 3.74 (d, 1H), 2.59 (s, 3H). 'H NMR (400 MHz, CDCI 3 d, ppm): 8.31 (t, 1H), 7.59 (d, 2H), 7.34 (d, 2H), 7.18-6.95 (m, 4H), 4.53 (ddd, 1H ), 4.22 (m, 1H), 4.02 (dd, 1H), 3.74 (d, 1H), 2.59 (s, 3H).
Beispiel Nr. 1.2-32: Example No. 1.2-32:
‘H-NMR (300.1 MHz, DMSO d, ppm): 10.17 (s, 1H), 7.90 (t, 1H), 7.45-7.07 (m, 7H), 4.34 (ddd, 1H), ’H-NMR (300.1 MHz, DMSO d, ppm): 10.17 (s, 1H), 7.90 (t, 1H), 7.45-7.07 (m, 7H), 4.34 (ddd, 1H),
4.29 (m, 1H), 4.01 (q, 1H), 3.77 (dd, 1H), 2.52 (s, 3H). 4.29 (m, 1H), 4.01 (q, 1H), 3.77 (dd, 1H), 2.52 (s, 3H).
Beispiel Nr. 1.54-37: Example No. 1.54-37:
‘H-NMR (300.1 MHz, DMSO d, ppm): 10.14 (s, 1H), 7.91 (dt, 1H), 7.67-7.15 (m, 6H), 4.40-4.31 (m, ’H-NMR (300.1 MHz, DMSO d, ppm): 10.14 (s, 1H), 7.91 (dt, 1H), 7.67-7.15 (m, 6H), 4.40-4.31 (m,
2H), 4.08 (q, 1H), 3.78 (dd, 1H), 3.06 (q, 2H), 1.30 (t, 3H). 2H), 4.08 (q, 1H), 3.78 (dd, 1H), 3.06 (q, 2H), 1.30 (t, 3H).
Beispiel Nr. 1.64-37: Example No. 1.64-37:
‘H-NMR (300.1 MHz, DMSO d, ppm): 10.16 (s, 1H), 7.89 (dt, 1H), 7.67-7.16 (m, 6H), 5.92 (m, 1H), ’H-NMR (300.1 MHz, DMSO d, ppm): 10.16 (s, 1H), 7.89 (dt, 1H), 7.67-7.16 (m, 6H), 5.92 (m, 1H),
5.29 (d, 1H), 5.11 (d, 1H), 4.40-4.30 (m, 2H), 4.11 (q, 1H), 3-80-3.74 (m, 3H). 5.29 (d, 1H), 5.11 (d, 1H), 4.40-4.30 (m, 2H), 4.11 (q, 1H), 3-80-3.74 (m, 3H).
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. 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 shown in ppm and then the signal intensity in round brackets. The d-value - signal intensity-number pairs of different signal peaks are listed separated from each other by semicolons.
Die Peakliste eines Beispieles hat daher die Form: di (Intensität^; d2 (Intensität2); . ; d; (Intensität^; . ; dh (Intensitätn) The peak list of an example therefore has the form: di (intensity ^; d2 (intensity2);.; D; (intensity ^;.; D h (intensity n )
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 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. With 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 specifying compound 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 given 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. 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 Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. Recognize manufacturing process based on "by-product fingerprints". 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. Further details on 1H NMR peak lists can be found in Research Disclosure Database Number 564025.
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Gegenstand der vorliegenden Erfindung ist somit die Verwendung 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 Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.82) und/oder deren Salze, jeweils wie oben definiert, als Herbizid und/oder Pflanzenwachstumsregulator, vorzugsweise in Kulturen von Nutz- und/oder Zierpflanzen. 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 Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.82) 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. The present invention thus relates to the use of one or more 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 (1.82) and / or their salts, each as defined above, as a 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 configurations characterized as preferred or particularly preferred, in particular one or more compounds of the formulas (1.1) to (1.82) and / or the salts thereof, in each case as defined above, or an agent according to the invention, as defined below, to which (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 Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der Formeln (1.1) bis (1.82) 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. The present invention also relates to a method for controlling unwanted plants, preferably in crops, 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 characterized embodiment, in particular one or more compounds of the formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention, as defined below, on undesired plants (for example harmful plants such as mono - or dicotyledonous weeds or unwanted 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 land or non-cultivated land) or the acreage surface (i.e. the 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 Ausgestaltung, insbesondere einer oder mehrerer Verbindungen der allgemeinen Formeln (1.1) bis (1.82) 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 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. Regulating the growth of plants, preferably 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, preferably in one of the configurations which are characterized as preferred or particularly preferred, in particular one or several compounds of the general formulas (1.1) to (1.82) and / or their salts, each as defined above, or an agent according to the invention as defined below, the plant, the seed of the plant (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 plants grow (e.g. the soil of cultivated or non-cultivated land) or the area under cultivation (ie the area on which the plants will grow) is applied.
Dabei können die erfindungsgemäßen Verbindungen bzw. die erfindungsgemäßen Mittel z.B. im Vorsaat- (gegebenenfalls auch durch Einarbeitung in den Boden), Vorauflauf- und/oder The compounds according to the invention or the agents according to the invention can e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence and / or
Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll. Post-emergence procedures are applied. Some representatives of the monocotyledonous and dicotyledonous weed flora, which can be used to control the compounds according to the invention, should be mentioned by way of example, without any intention that the name should limit them to certain species.
Vorzugsweise werden in einem erfindungsgemäßen Verfahren zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung von Pflanzen eine oder mehrere Verbindungen der allgemeinen Formel (I) und/oder deren Salze zur Bekämpfung von Schadpflanzen oder zur Wachstumsregulierung in Kulturen von Nutzpflanzen oder Zierpflanzen eingesetzt, wobei die Nutzpflanzen oder Zierpflanzen in einer bevorzugten Ausgestaltung transgene Pflanzen sind. In a process according to the invention for controlling harmful plants or for regulating the growth of plants, one or more compounds of the general formula (I) and / or their salts are preferably used for controlling harmful plants or for regulating growth in crops of useful plants or ornamental plants, the useful plants or ornamental plants in a preferred embodiment are transgenic plants.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (1) und/oder deren Salze eignen sich zur Bekämpfung der folgenden Gattungen von monokotylen und dikotylen Schadpflanzen: The compounds of general formula (1) and / or their salts according to the invention are suitable for combating the following genera of monocotyledonous and dicotyledonous harmful plants:
Monokotyle Schadpflanzen der Gattungen: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, lmperata, lschaemum, 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, Echinochloa, Eleocharis, Eleusine, Eragrostata, Festiochaperimist, Eriochaperim , lschaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Schadpflanzen 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, lpomoea, 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.  Dicotyledonous harmful plants of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphor , Galinsoga, Galium, Hibiscus, lpomoea, 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.
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. If the compounds according to the invention are applied to the surface of the earth prior to germination of the harmful plants (grasses and / or weeds) (pre-emergence method), either the emergence of the weed or weed seedlings is completely prevented or they grow to the cotyledon stage approach, but then stop growing and eventually die completely after three to four weeks.
Bei Applikation der erfindungsgemäßen Verbindungen auf die grünen Pflanzenteile im When applying the compounds of the invention to the green parts of the plant in
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 Post-emergence treatment stops growing after the treatment and the harmful plants remain in the growth stage at the time of application or die completely after a certain time, so that this is harmful to the crop plants
Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird. Weed competition is eliminated very early and sustainably.
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 of the invention have excellent herbicidal activity against mono- and dicotyledon weeds, crops of economically important crops 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 particular compound according to the invention and its application rate only insignificantly or not harmed at all. For these reasons, the present compounds are very suitable for the selective control of undesired plant growth in crops such as
landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen. agricultural crops or ornamental crops.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Emteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativem Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann. In addition, the compounds according to the invention (depending on their respective structure and the application rate applied) have excellent growth-regulating properties in crop plants. They intervene regulating the plant's own metabolism and can thus be used to influence plant constituents in a targeted manner and to facilitate the harvest, e.g. by triggering desiccation and stunted growth. Furthermore, they are also suitable for general control and inhibition of undesirable vegetative growth without killing the plants. Inhibiting vegetative growth plays a major role in many monocotyledonous and dicotyledonous crops, since, for example, this can reduce or completely prevent stock formation.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfindungsgemäßen Verbindungen auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Due to their herbicidal and plant growth regulatory properties, the compounds according to the invention can also be used to control harmful plants in crops of plants which have been modified by genetic engineering or by conventional mutagenesis. The transgenic plants are generally distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern, for example, the crop in terms of quantity, quality, shelf life, composition and special ingredients. Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known.
Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen und/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. Preferred with respect to transgenic cultures is the use of the compounds according to the invention and / or their salts in economically important transgenic cultures 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.
Vorzugsweise können die erfindungsgemäßen Verbindungen auch als Herbizide in  The compounds according to the invention can preferably also be used as herbicides
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.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die erfindungsgemäßen Verbindungen 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 Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z.B. das Emtegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe.Due to their herbicidal and plant growth regulatory properties, the compounds according to the invention 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 distinguished by special advantageous properties, for example resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties concern e.g. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Emteguts bekannt. Weitere besondere Eigenschaften können in einer Toleranz oder Resistenz gegen abiotische Stressoren z.B. Hitze, Kälte, Trockenheit, Salz und ultraviolette Strahlung liegen. Transgenic plants with an increased starch content or altered starch quality or those with a different fatty acid composition of the crop are known. Other special properties can include tolerance or resistance to abiotic stressors e.g. There is 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, Triticale, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten. 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, triticale, millet, rice, manioc and maize or also crops of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetables.
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 Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden. Conventional ways of producing new plants, which have modified properties compared to previously occurring plants, are, for example, classic ones Breeding methods and the generation of mutants. Alternatively, new plants with modified properties can be created using genetic engineering methods.
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind dem Fachmann bekannt. 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. Numerous molecular biological techniques with which new transgenic plants with modified properties can be produced are known to the person skilled in the art. For such genetic engineering manipulations, nucleic acid molecules can be introduced into plasmids which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard procedures e.g. Base exchanges made, partial sequences removed or natural or synthetic sequences added. To connect the DNA fragments to one another, adapters or linkers can be attached to the fragments.
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. 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 gene product mentioned above.
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. 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). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden. 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 certain compartment, e.g. the coding region is linked 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). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen 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, ie 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 (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z.B. Dicamba oder gegen Herbizide, die essentielle The compounds (I) according to the invention can preferably be used in transgenic cultures which are active against growth substances, e.g. Dicamba or against herbicides, the essential
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, resistent sind. Plant enzymes, e.g. Inhibit acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or hydoxyphenylpyruvate dioxygenases (HPPD), or are resistant to herbicides from the group of sulfonylureas, glyphosates, glufosinates or benzoylisoxazoles and analogous active ingredients.
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, there are often effects 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 which can be used for the application, preferably good combinability with the herbicides to which the transgenic crop 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) und/oder deren Salze als Herbizide zur Bekämpfung von Schadpflanzen in Kulturen von Nutz- oder Zierpflanzen, gegebenenfalls in transgenen Kulturpflanzen. The invention therefore also relates to the use of the compounds of the general formula (I) and / or their salts as herbicides for controlling harmful plants in crops of useful or ornamental plants, if appropriate 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. Pre-or post-soya use is also preferred.
Die erfindungsgemäße Verwendung zur Bekämpfung von Schadpflanzen oder zur 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, gegebenenfalls 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 on 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 applied.
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 (1.82) und/oder deren Salze, jeweils wie oben definiert, Design, in particular one or more compounds of the formulas (1.1) to (1.82) 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) customary in crop 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, antifoams, water, organic solvents, preferably at 25 ° C. and 1013 mbar, organic solvents miscible with water in any ratio.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) 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, die Verbindungen der allgemeinen Formel (I) und/oder deren Salze enthalten. The compounds of the general formula (I) 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 herbicides and Plant growth regulating agents which contain compounds of the general formula (I) and / or their salts.
Die Verbindungen der allgemeinen Formel (I) und/oder deren Salze können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als 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, The compounds of general formula (I) and / or their salts can be formulated in various ways, depending on which biological and / or chemical-physical parameters are specified. Possible formulation options are, 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 ,
Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Suspension concentrates (SC), dispersions based on oil or water, oil-miscible solutions,
Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Capsule suspensions (CS), dusts (DP), pickling agents, granules for the litter and
Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations,
Mikrokapseln und Wachse. Microcapsules and waxes.
Diese einzelnen Formulierungstypen und die Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind dem Fachmann bekannt, und werden beispielsweise beschrieben 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 Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Grenzflächenaktive These individual types of formulation and formulation auxiliaries such as inert materials, surfactants, solvents and other additives are known to the person skilled in the art 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 Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt, "Interface Active
Äthylenoxidaddukte", Wiss. Verlagsgesellschaft, Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986. Äthylenoxidaddukte ", Scientific Publishing Company, Stuttgart 1976; Winnacker-Küchler," Chemical Technology ", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
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. In addition to the active substance, they contain surfactants of an ionic and / or non-ionic type (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 also contain sodium acid. To produce the wettable powders, the herbicidal active ingredients are finely ground, for example in conventional apparatus 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 Calcium-Salze wie Emulsifiable concentrates are obtained by dissolving the active ingredient in an organic solvent, for example butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or several 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, F ettalkoholpolyglykolether, Propylenoxid-Ethylenoxid- Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Alkylaryl polyglycol ether, fatty alcohol polyglycol ether, propylene oxide-ethylene oxide condensation products, alkyl polyether, sorbitan esters such as e.g. Sorbitan fatty acid esters or
Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester. Polyoxethylene sorbitan esters such as e.g. Polyoxyethylene sorbitan fatty acid esters.
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 types of formulation.
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 Granules can either be produced by spraying the active ingredient onto adsorbable, granulated inert material or by applying active ingredient concentrates by means of adhesives, e.g. Polyvinyl alcohol, sodium polyacrylic acid or mineral oils, on the surface of carriers such as sand, kaolinite or granulated inert material. Also suitable ones
Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden. Active ingredients are 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 Sprühgranulaten siehe z.B. Verfahren 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. 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, 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 further details on the formulation of crop protection agents see, for example, GC Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.
Die agrochemischen Zubereitungen, vorzugsweise herbizide oder pflanzenwachstumsregulierende Mittel der vorliegenden Erfindung enthalten vorzugsweise eine Gesamtmenge von 0,1 bis 99 Gew.-%, bevorzugt 0,5 bis 95 Gew.-%, weiter bevorzugt 1 bis 90 Gew.-%, insbesondere bevorzugt 2 bis 80 Gew.-%, an erfindungsgemäßen Verbindungen der allgemeinen Formel (I) und deren Salzen. The agrochemical preparations, preferably herbicidal or plant growth-regulating agents of the present invention preferably contain a total amount of 0.1 to 99% by weight, preferably 0.5 to 95% by weight, more preferably 1 to 90% by weight, particularly preferably 2 to 80% by weight of compounds of the general formula (I) according to the invention and their salts.
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. Dusty
Formulierungen enthalten 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 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.-%. Formulations contain 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. In the case of water-dispersible granules, the active ingredient content depends in part on whether the active compound is in liquid or solid form and which granulating 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. Beispiele für Formulierungshilfsmittel sind unter anderem in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998) beschrieben. In addition, the active ingredient formulations mentioned may contain the usual adhesives, wetting agents, dispersing agents, emulsifying agents, penetration agents, preservatives, antifreeze agents and solvents, fillers, carriers and dyes, defoamers, evaporation inhibitors and the pH and Agents influencing viscosity. Examples of formulation auxiliaries are described, inter alia, in "Chemistry and Technology of Agrochemical Formulations", ed. D. A. Knowles, Kluwer Academic Publishers (1998).
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 the 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 der allgemeinen Formel (I) in Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA-Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat- Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. in Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", l6th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 und der dort zitierten Literatur beschrieben sind. As a combination partner for the compounds of the general formula (I) according to the invention in mixture formulations or in a tank mix, there are, for example, known active substances which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate Synthase, glutamine synthetase, p-hydroxyphenylpyruvate Dioxygenase, phytoendesaturase, Photosystem I, Photosystem II, protoporphyrinogen oxidase are used, as described, for example, in Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 16th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2012 and the literature cited therein.
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 in the crop plants in principle in some crops and especially also in the case of mixtures with other herbicides which are less selective. In this regard, combinations are
erfindungsgemäßer Verbindungen (I) von besonderem Interesse, welche die Verbindungen der allgemeinen Formel (I) 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 (I) according to the invention of particular interest which contain the compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners. The safeners, which are used in an antidote effective content, reduce the phytotoxic side effects of the herbicides / pesticides used, e.g. in economically important crops such as cereals (wheat, barley, rye, maize, 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 (I) 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 (I) 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 provided and applied.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Herbizid- oder Herbizid- Safener- Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvem, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- bzw. Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren inerten Stoffen verdünnt. For use, the herbicide or herbicide safener formulations present in commercially available form are optionally diluted in the customary manner, for example in the case of wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules using water. Preparations in the form of dust, ground granules or scattering granules and sprayable solutions are usually no longer diluted with other inert substances before use.
Äußere Bedingungen wie Temperatur, Feuchtigkeit etc. beeinflussen zu einem gewissen Teil die Aufwandmenge der Verbindungen der allgemeinen Formel (I) und/oder deren Salze. Die External conditions such as temperature, humidity etc. influence to a certain extent the application rate of the compounds of the general formula (I) and / or their salts. The
Aufwandmenge kann dabei innerhalb weiter Grenzen variieren. Für die Anwendung als Herbizid zur Bekämpfung von Schadpflanzen liegt die Gesamtmenge an Verbindungen der allgemeinen Formel (I) und deren Salze vorzugsweise im Bereich von 0,001 bis 10,0 kg/ha, bevorzugt im Bereich von 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. Dies gilt sowohl für die Anwendung im Vorauflauf oder im Nachauflauf. Bei der Anwendung von Verbindungen der allgemeinen Formel (I) und/oder deren Salzen als The application rate can vary within wide limits. For use as a herbicide for controlling harmful plants, the total amount of compounds of the general formula (I) and their salts is preferably in the range from 0.001 to 10.0 kg / ha, preferably in the range from 0.005 to 5 kg / ha, more preferably in Range from 0.01 to 1.5 kg / ha, particularly preferably in the range from 0.05 to 1 kg / ha. This applies to both pre-emergence and post-emergence applications. When using compounds of general formula (I) and / or their salts as
Pflanzenwachstumsregulator, beispielsweise als Halmverkürzer bei Kulturpflanzen, wie sie oben genannt worden sind, vorzugsweise bei Getreidepflanzen wie Weizen, Gerste, Roggen, Triticale, Hirse, Reis oder Mais, liegt die Gesamt- Aufwandmenge vorzugsweise im Bereich von 0,001 bis 2 kg/ha, vorzugsweise im Bereich von 0,005 bis 1 kg/ha, insbesondere im Bereich von 10 bis 500 g/ha, ganz besonders bevorzugt im Bereich von 20 bis 250 g/ha. Dies gilt sowohl für die Anwendung im Plant growth regulator, for example as a stalk shortener in crop plants as mentioned above, preferably in cereal plants such as wheat, barley, rye, triticale, millet, rice or corn, the total application rate is preferably in the range from 0.001 to 2 kg / ha, preferably in the range from 0.005 to 1 kg / ha, in particular in the range from 10 to 500 g / ha, very particularly preferably in the range from 20 to 250 g / ha. This applies both to the application in
Vorauflauf oder im Nachauflauf. Pre-emergence or post-emergence.
Die Applikation als Halmverkürzer kann in verschiedenen Stadien des Wachstums der Pflanzen erfolgen. Bevorzugt ist beispielsweise die Anwendung nach der Bestockung am Beginn des The application as a straw shortener can take place in different stages of the growth of the plants. For example, use after planting at the beginning of the
Längenwachstums . Linear growth.
Alternativ kommt bei der Anwendung als Pflanzenwachstumsregulator auch die Behandlung des Saatguts in Frage, welche die unterschiedlichen Saatgutbeiz- und Beschichtungstechniken einschließt. Die Aufwandmenge hängt dabei von den einzelnen Techniken ab und kann in Vorversuchen ermittelt werden. Alternatively, when used as a plant growth regulator, the treatment of the seed, which includes the different seed dressing and coating techniques, can also be used. The application rate depends on the individual techniques and can be determined in preliminary tests.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in erfindungsgemäßen Mitteln (z.B. Mischungsformulierungen oder im Tank-Mix) sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p- Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II oder As a combination partner for the compounds of the general formula (I) according to the invention in agents according to the invention (for example mixture formulations or in a tank mix), there are, for example, known active ingredients which are based on inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate -3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoendesaturase, Photosystem I, Photosystem II or
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, 2012 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 International Organization for Standardization (ISO) oder mit dem chemischen Namen bzw. mit der Codenummer bezeichnet sind. Dabei sind stets sämtliche Protoporphyrinogen oxidase are used, such as those 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, 2012 and the literature cited therein. Hereinafter 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 (ISO) or with the chemical name or with the code number are designated. There are always everyone
Anwendungsformen wie beispielsweise Säuren, Salze, Ester sowie auch alle isomeren Formen wie Stereoisomere und optische Isomere umfasst, auch wenn diese nicht explizit erwähnt sind. Application forms such as acids, salts, esters and also all isomeric forms such as stereoisomers and optical isomers, 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, amidosulfüron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3- methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- 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, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, 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-l,2-oxazolidin-3- one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-l,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, ethametsulfuron-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, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfüron, 4-amino-3-chloro-6- (4-chloro-2-fluoro-3-methylphenyl ) -5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor- potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammonium sulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, benzenulfonon, benzone clonbenzene benzophenone, bensulophenone, bentobenzene benzophenone, benzene benzophenone, benzene benzophenone bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate and -octanoate, busoxinone, butachlor, butafenacil, butachlorateimine, butamifos, butamifos , cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chloridhalonuron, dimethyl, chloridhalonuron, dimethyl -ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloran sulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 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, -dimethylammonium, isooctyl, -potassium and -sodium , daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2- (2,4-dichlorobenzyl) -4,4-dimethyl-l, 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, diphenamid, diquat, diquat-dibromid, dithiopyr, endogenous, dithron, EPH halfluralin, ethametsulfuron, ethametsulfuron-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-lH-tetrazol-l-yl] phenyl] ethanesulfonamide, F-7967, ie 3- [7-chloro-5-fluoro-2- (trifluoromethyl) -IH -benzimidazol-4-yl] -l-methyl-6- (trifluoromethyl) pyrimidine-2,4 (1H, 3H) -dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, 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, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium und -trimesium, H-9201, i.e. 0-(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. l-(Dimethoxyphosphoryl)-ethyl-(2,4- dichlorphenoxy)acetat, 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, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonoglypane-cyanogen flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate ammonium, pufosinate ammonium P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, - potassium, -sodium and -trimesium, H-9201, ie 0- (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, ie l- (dimethoxyphosphoryl) ethyl (2,4-dichlorophenoxy) acetate, 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, -potazaben, isopurone, isofurone, iprophonone, isulfonone, isopurone and ip, , carbutilate, KUH-043, ie 3 - ({[5- (difluoromethyl) -l-methyl-3- (trifluoromethyl) -1H-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, 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, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, 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, SL-261, sulcotrion, sulfentrazone, sulfometuron, 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, triflusulfüron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, i.e. 3,4-Dichlor-N-{2- [(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}anilin, sowie die folgenden Verbindungen: 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, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulone, pentachloramide, pentachlorone, pentachlorone, pentachlorone phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone-sodium, propoxycarbazone furon, Propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen- ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, 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, quizalofonofulfonyl , sethoxydim, siduron, simazine, simetryn, SL-261, 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, tebuthiuron, tefuryltrione , Tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazine, 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, triflusulfüron-methyl, tritosulfuron, urea sulfate, vemolate, XDE-848, ZJ-0862, ie 3,4-dichloro-N- {2- [(4,6-dimethoxypyrimidin-2-yl) oxy] benzyl} aniline, and the following connections:
Figure imgf000122_0001
Figure imgf000122_0001
Beispiele für Pflanzenwachstumsregulatoren als mögliche Mischungspartner sind: Examples of plant growth regulators as possible mix 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.
Ebenfalls als Kombinationspartner für die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) kommen beispielsweise die folgenden Safener in Frage: Sl) Verbindungen aus der Gruppe heterocyclischer Carbonsäurederivate: The following safeners are also suitable as combination partners for the compounds of the general formula (I) according to the invention: S1) Compounds from the group of heterocyclic carboxylic acid derivatives:
S 1 a) V erbindungen vom Typ der Dichlorphenylpyrazolin-3 -carbonsäure (S 1 a), vorzugsweise S 1 a ) Compounds of the type of dichlorophenylpyrazoline-3-carboxylic acid (S 1 a ), preferably
Verbindungen wie l-(2,4-Dichlorphenyl)-5-(ethoxycarbonyl)-5-methyl-2-pyrazolin-3-carbonsäure,Connections like 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; 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;
S 1 b) Derivate der Dichlorphenylpyrazolcarbonsäure (S 1 b), vorzugsweise V erbindungen wie S 1 b ) derivatives of dichlorophenylpyrazole carboxylic acid (S 1 b ), preferably compounds such as
1 -(2,4-Dichlorphenyl)-5-methylpyrazol-3 -carbonsäureethylester (S 1 -2),  1 - (2,4-dichlorophenyl) -5-methylpyrazole-3-carboxylic acid ethyl ester (S 1 -2),
l-(2,4-Dichlorphenyl)-5-isopropylpyrazol-3-carbonsäureethylester (Sl-3),  l- (2,4-dichlorophenyl) -5-isopropylpyrazole-3-carboxylic acid ethyl ester (S1-3),
1 -(2,4-Dichlorphenyl)-5-(l , 1 -dimethyl-ethyl)pyrazol-3-carbonsäureethylester (S 1 -4) und verwandte Verbindungen, wie sie in EP-A-333131 und EP-A-269806 beschrieben sind;  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-333131 and EP-A-269806 are described;
Slc) Derivate der l,5-Diphenylpyrazol-3-carbonsäure (Slc), vorzugsweise Verbindungen wie Sl c ) derivatives of l, 5-diphenylpyrazole-3-carboxylic acid (Sl c ), preferably compounds such as
l-(2,4-Dichlorphenyl)-5-phenylpyrazol-3-carbonsäureethylester (Sl-5),  ethyl 1- (2,4-dichlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-5),
l-(2-Chlorphenyl)-5-phenylpyrazol-3-carbonsäuremethylester (Sl-6) und verwandte  Methyl 1- (2-chlorophenyl) -5-phenylpyrazole-3-carboxylate (S1-6) and related
Verbindungen wie sie beispielsweise in der EP-A-268554 beschrieben sind;  Compounds as described for example in EP-A-268554;
Sld) Verbindungen vom Typ der Triazolcarbonsäuren (Sld), vorzugsweise Verbindungen wie Sl d ) compounds of the triazole carboxylic acid type (Sl d ), preferably compounds such as
Fenchlorazol(-ethylester), d.h. l-(2,4-Dichlorphenyl)-5-trichlormethyl-(lH)-l,2,4-triazol-3- carbonsäureethylester (Sl-7), und verwandte Verbindungen, wie sie in EP-A-174562 und EP-A-346620 beschrieben sind;  Fenchlorazole (ethyl ester), i.e. l- (2,4-dichlorophenyl) -5-trichloromethyl- (lH) -l, 2,4-triazole-3-carboxylic acid ethyl ester (S1-7), and related compounds as described in EP-A-174562 and EP- A-346620;
Sle) 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 Sl e ) compounds of the 5-benzyl- or 5-phenyl-2-isoxazoline-3-carboxylic acid type, or the 5,5-diphenyl-2-isoxazoline-3-carboxylic acid (Sl e ), preferably compounds such as
5-(2,4-Dichlorbenzyl)-2-isoxazolin-3 -carbonsäureethylester (Sl-8) oder  5- (2,4-dichlorobenzyl) -2-isoxazoline-3-carboxylic acid ethyl ester (Sl-8) or
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-carbonsäure (S1-10) oder 5,5-Diphenyl-2-isoxazolin-3-carbonsäureethylester (Sl-l 1) ("Isoxadifen-ethyl")  5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S1-9) and related compounds, as described in WO-A-91/08202, or 5,5-diphenyl-2-isoxazoline-carboxylic acid (S1-10 ) or 5,5-Diphenyl-2-isoxazoline-3-carboxylic acid ethyl ester (Sl-l 1) ("Isoxadifen-ethyl")
oder -n-propylester (S1-12) oder 5-(4-Fluorphenyl)-5-phenyl-2-isoxazolin-3-carbon- säureethylester (S 1-13), wie sie in der Patentanmeldung WO-A-95/07897 beschrieben sind.  or -n-propyl ester (S1-12) or 5- (4-fluorophenyl) -5-phenyl-2-isoxazoline-3-carboxylic acid ethyl ester (S 1-13), as described in patent application WO-A-95 / 07897 are described.
S2) Verbindungen aus der Gruppe der 8-Chinolinoxyderivate (S2): S2) Compounds from the group of 8-quinoline oxy-derivatives (S2):
S2a) Verbindungen vom Typ der 8-Chinolinoxyessigsäure (S2a), vorzugsweise S2 a ) Compounds of the 8-quinolineoxyacetic acid (S2 a ) type, preferably
(5-Chlor-8-chinolinoxy)essigsäure-(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 (l-methylhexyl) ester ("Cloquintocet-mexyl") (S2-1), (5-chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but -l-yl) -ester (S2-2),
(5-Chlor-8-chinolinoxy)essigsäure-4-allyl-oxy-butylester (S2-3),  (5-chloro-8-quinolinoxy) 4-allyl-oxy-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-Chlor-8-chinolinoxy)essigsäureallylester (S2-7), (5-chloro-8-quinolinoxy) methyl acetate (S2-6), (5-chloro-8-quinolinoxy) allyl acetate (S2-7),
(5-Chlor-8-chinolinoxy)essigsäure-2-(2-propyliden-iminoxy)-l-ethylester (S2-8),  (5-chloro-8-quinolinoxy) acetic acid 2- (2-propylidene-iminoxy) -l-ethyl ester (S2-8),
(5-Chlor-8-chinolinoxy)essigsäure-2-oxo-prop-l-ylester (S2-9) und verwandte Verbindungen, wie sie in EP-A-86750, EP-A-94349 und EP-A-191736 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;  (5-Chloro-8-quinolinoxy) 2-oxo-prop-1-yl acetate (S2-9) and related compounds as described in EP-A-86750, EP-A-94349 and EP-A-191736 or EP-A-0 492 366 are described, and (5-chloro-8-quinolinoxy) acetic acid (S2-10), their hydrates and salts, for example their lithium, sodium, potassium, calcium, magnesium, aluminum , Iron, ammonium, quaternary ammonium, sulfonium, or phosphonium salts as described in WO-A-2002/34048;
S2b) Verbindungen vom Typ der (5-Chlor-8-chinolinoxy)malonsäure (S2b), vorzugsweise S2 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-chloro-8-quinolinoxy) diallyl malonate,
(5-Chlor-8-chinolinoxy)malonsäure-methyl-ethylester und verwandte Verbindungen, wie sie in EP-A-0 582 198 beschrieben sind.  Methyl (5-chloro-8-quinolinoxy) malonic acid and related compounds as described in EP-A-0 582 198.
53) Wirkstoffe vom Typ der Dichloracetamide (S3), die häufig als Vorauflaufsafener 53) Active substances of the type of dichloroacetamide (S3), often as pre-emergence safeners
(bodenwirksame Safener) angewendet werden, wie z. B.  (Soil-effective 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-28725" (3-Dichloracetyl-2,2,-dimethyl-l,3-oxazolidin) der Firma Stauffer (S3-3),  "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),
"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  "PPG-1292" (N-allyl-N - [(1,3-dioxolan-2-yl) methyl] dichloroacetamide) from PPG
Industries (S3-5),  Industries (S3-5),
"DKA-24" (N-Allyl-N-[(allylaminocarbonyl)methyl]-dichloracetamid) der Firma Sagro-Chem (S3-6),  "DKA-24" (N-allyl-N - [(allylaminocarbonyl) methyl] dichloroacetamide) from Sagro-Chem (S3-6),
"AD-67" oder "MON 4660" (3-Dichloracetyl-l-oxa-3-aza-spiro[4,5]decan) der Firma  "AD-67" or "MON 4660" (3-dichloroacetyl-l-oxa-3-aza-spiro [4,5] decane) from the company
Nitrokemia bzw. Monsanto (S3-7),  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).  ((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), as well as its (R) -isomer (S3-11).
54) Verbindungen aus der Klasse der Acylsulfonamide (S4): 54) Compounds from the class of acylsulfonamides (S4):
S4a) N- Acylsulfonamide der Formel (S4a) und deren Salze wie sie in der WO-A-97/45016 S4 a ) N-acylsulfonamides of the formula (S4 a ) and their salts as described in WO-A-97/45016
beschrieben sind,
Figure imgf000125_0001
wonn are described
Figure imgf000125_0001
wonn
RA 1 (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, wobei die 2 letztgenannten Reste durch VA R A 1 (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, the 2 last-mentioned radicals by VA
Substituenten aus der Gruppe Halogen, (Ci-C i)Alkoxy, (Ci-C6)Haloalkoxy und (Ci- C i)Alkyltliio und im Falle cyclischer Reste auch durch (Ci-C i)Alkyl und (Ci-C4)Haloalkyl substituiert sind; Substituents from the group halogen, (Ci-C i) alkoxy, (Ci-C 6 ) haloalkoxy and (Ci-Ci) alkyltliio and in the case of cyclic radicals also by (Ci-Ci) alkyl and (Ci-Ci) haloalkyl are substituted;
RA2 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; mA 1 oder 2; RA 2 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m A 1 or 2;
VA ist 0, 1 , 2 oder 3 bedeuten; VA is 0, 1, 2 or 3;
S4b) Verbindungen vom Typ der 4-(Benzoylsulfamoyl)benzamide der Formel (S4b) und deren Salze, wie sie in der WO-A-99/16744 beschrieben sind, S4 b ) compounds of the 4- (benzoylsulfamoyl) benzamide type of the formula (S4 b ) and their salts, as described in WO-A-99/16744,
Figure imgf000125_0002
wonn
Figure imgf000125_0002
wonn
RB1, RB2 unabhängig voneinander Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C3- C6)Alkenyl, (C3-C6)Alkinyl, RB 1 , RB 2 independently of one another hydrogen, (Ci-C 6 ) alkyl, (C3-C6) cycloalkyl, (C3-C 6 ) alkenyl, (C3-C 6 ) alkynyl,
RB3 Halogen, (Ci-C4)Alkyl, (Ci-C4)Haloalkyl oder (Ci-C4)Alkoxy und me 1 oder 2 bedeuten, z.B. solche worin RB 3 is halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl or (Ci-C 4 ) alkoxy and me is 1 or 2, for example those in which
RB1 = Cyclopropyl, RB2 = Wasserstoff und (RB3) = 2-OMe ist ("Cyprosulfamide", S4-1),RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 2-OMe ("Cyprosulfamide", S4-1),
RB1 = Cyclopropyl, RB2 = Wasserstoff und (RB3) = 5-Cl-2-OMe ist (S4-2), RB 1 = Ethyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist(S4-3), RB 1 = cyclopropyl, RB 2 = hydrogen and (RB 3 ) = 5-Cl-2-OMe is (S4-2), R B 1 = ethyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is (S4-3),
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 5-Cl-2-OMe ist (S4-4) und R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 5-Cl-2-OMe is (S4-4) and
RB 1 = Isopropyl, RB 2 = Wasserstoff und (RB 3) = 2-OMe ist(S4-5); R B 1 = isopropyl, R B 2 = hydrogen and (R B 3 ) = 2-OMe is (S4-5);
S4C) Verbindungen aus der Klasse der Benzoylsulfamoylphenylhamstoffe der Formel (S4C), wie sie in der EP-A-365484 beschrieben sind, S4 C ) compounds from the class of the benzoylsulfamoylphenylureas of the formula (S4 C ) as described in EP-A-365484,
Figure imgf000126_0001
wonn
Figure imgf000126_0001
wonn
Rc1, Rc2 unabhängig voneinander Wasserstoff, (Ci-Cg)Alkyl, (C3-Cg)Cycloalkyl, (C3-Rc 1 , Rc 2 independently of one another hydrogen, (Ci-Cg) alkyl, (C3-Cg) cycloalkyl, (C3-
C6)Alkenyl, (C3-C6)Alkinyl, C 6 ) alkenyl, (C 3 -C 6 ) alkynyl,
Rc3 Halogen, (Ci-C i)Alkyl, (Ci-C4)Alkoxy, CF3 und mc 1 oder 2 bedeuten; beispielsweise l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3-methylhamstoff, Rc 3 is halogen, (Ci-C i) alkyl, (Ci-C4) alkoxy, CF 3 and m c 1 or 2; for example 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea,
l-[4-(N-2-Methoxybenzoylsulfamoyl)phenyl]-3,3-dimethylhamstoff,  1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethyl urea,
l-[4-(N-4,5-Dimethylbenzoylsulfamoyl)phenyl]-3-methylhamstoff;  1- [4- (N-4,5-Dimethylbenzoylsulfamoyl) phenyl] -3-methylurea;
S4d) Verbindungen vom Typ der N-Phenylsulfonylterephthalamide der Formel (S4d) und deren Salze, die z.B. bekannt sind aus CN 101838227, S4 d ) compounds of the N-phenylsulfonylterephthalamide type of the formula (S4 d ) and their salts, which are known, for example, from CN 101838227,
Figure imgf000126_0002
wonn
Figure imgf000126_0002
wonn
RD 4 Halogen, (Ci-C4)Alkyl, (Ci-C4)Alkoxy, CF3; mD 1 oder 2; RD5 Wasserstoff, (Ci-C6)Alkyl, (C3-C6)Cycloalkyl, (C2-C6)Alkenyl, (C2-C6)Alkinyl, (C5- C6)Cycloalkenyl bedeutet. R D 4 halogen, (Ci-C 4 ) alkyl, (Ci-C 4 ) alkoxy, CF 3; m D 1 or 2; RD 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- 3,4,5-triacetoxybenzoic acid ethyl ester, 3,5-dimethoxy-4-hydroxybenzoic acid, 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. 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)-l ,2-dihydrochinoxalin-2-on, 1 -Methyl-3-(2-thienyl)-l ,2-dihydro- chinoxalin-2-thion, l-(2-Aminoethyl)-3-(2-thienyl)-l,2-dihydro-chinoxalin-2-on-hydrochlorid, l-(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) -l, 2-dihydroquinoxalin-2-one, 1-methyl-3- (2-thienyl) -l, 2-dihydroquinoxalin-2-thione, l- (2nd -Aminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin-2-one hydrochloride, l- (2-methylsulfonylaminoethyl) -3- (2-thienyl) -l, 2-dihydro-quinoxalin- 2-one, as described in WO-A-2005/112630.
57) Verbindungen aus der Klasse der Diphenylmethoxyessigsäurederivate (S7), z.B. 57) Compounds from the class of diphenylmethoxyacetic acid derivatives (S7), e.g.
Diphenylmethoxyessigsäuremethylester (CAS-Reg.Nr. 41858-19-9) (S7-1),  Diphenylmethoxyacetic acid methyl ester (CAS Reg. No. 41858-19-9) (S7-1),
Diphenylmethoxyessigsäureethylester oder Diphenylmethoxyessigsäure wie sie in der WO-A- 98/38856 beschrieben sind.  Diphenylmethoxyacetic acid ethyl ester or Diphenylmethoxyacetic acid as described in WO-A-98/38856.
58) Verbindungen der Formel (S8), wie sie in der WO-A-98/27049 beschrieben sind, 58) compounds of the formula (S8), as described in WO-A-98/27049,
Figure imgf000127_0001
Figure imgf000127_0001
worin die Symbole und Indizes folgende Bedeutungen haben: where the symbols and indices have the following meanings:
RD1 ist Halogen, (Ci-C i)Alkyl, (Ci-C i)Haloalkyl, (Ci-C i)Alkoxy, (Ci-C4)Haloalkoxy, RD 1 is halogen, (Ci-C i) alkyl, (Ci-C i) haloalkyl, (Ci-C i) alkoxy, (Ci-C4) haloalkoxy,
RD 2 ist Wasserstoff oder (Ci-C i)Alkyl, R D 2 is hydrogen or (Ci-C i) alkyl,
RD 3 ist 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; oder deren Salze, nD ist eine ganze Zahl von 0 bis 2. R D 3 is hydrogen, (Ci-CsjAlkyl, (C 2 -C4) alkenyl, (C 2 -C4) alkynyl, or aryl, where each of the aforementioned C-containing radicals is unsubstituted or by one or more, preferably up to three of the same or various radicals from the group consisting of halogen and alkoxy, or their salts, n D is an integer from 0 to 2.
S9) Wirkstoffe aus der Klasse der 3-(5-Tetrazolylcarbonyl)-2-chinolone (S9), z.B. 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), l,2-Dihydro-4-hydroxy-l-methyl-3-(5-tetrazolyl-carbonyl)-2-chinolon (CAS-Reg.Nr.  l, 2-Dihydro-4-hydroxy-l-ethyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS Reg.No .: 219479-18-2), l, 2-dihydro-4-hydroxy- l-methyl-3- (5-tetrazolylcarbonyl) -2-quinolone (CAS reg. no.
95855-00-8), wie sie in der WO-A-1999/000020 beschrieben sind.  95855-00-8), as described in WO-A-1999/000020.
S10) Verbindungen der Formeln (Sl0a) oder (Sl0b), wie sie in der WO-A-2007/023719 und WO-A-2007/023764 beschrieben sind, S10) compounds of the formulas (Sl0 a ) or (Sl0 b ) as described in WO-A-2007/023719 and WO-A-2007/023764,
Figure imgf000128_0001
Figure imgf000128_0001
worin wherein
RE1 Halogen, (Ci-C i)Alkyl, Methoxy, Nitro, Cyano, CF3, OCF3 RE 1 halogen, (Ci-C i) alkyl, methoxy, nitro, cyano, CF3, OCF3
YE, ZE unabhängig voneinander O oder S, nß eine ganze Zahl von 0 bis 4, YE, ZE independently of one another O or S, n ß an integer from 0 to 4,
RE2 (Ci-Ci6)Alkyl, (C2-C6)Alkenyl, (C3-C6)Cycloalkyl, Aryl; Benzyl, Halogenbenzyl, RE3 Wasserstoff oder (Ci-C6)Alkyl bedeuten. RE 2 (Ci-Ci 6 ) alkyl, (C2-C6) alkenyl, (C3-C6) cycloalkyl, aryl; Benzyl, halobenzyl, RE 3 is hydrogen or (Ci-C 6 ) alkyl.
Sl l) Wirkstoffe vom Typ der Oxyimino- Verbindungen (Sl l), die als Saatbeizmittel bekannt sind, wie z. B. Sl l) active substances of the oxyimino compound type (Sl l), 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,  "Oxabetrinil" ((Z) -l, 3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile) (Sl l-l), which is known as a seed dressing safener for millet against damage to metolachlor,
"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 "Fluxofenim" (1- (4-chlorophenyl) -2,2,2-trifluoro-l-ethanone-0- (1,3-dioxolan-2-ylmethyl) -oxime) (Sl 1-2), which is used as a seed dressing -Safeer is known for millet against damage from metolachlor, and
"Cyometrinil" oder "CGA-43089" ((Z)-Cyanomethoxyimino(phenyl)acetonitril) (Sl l-3), das als Saatbeiz-Safener für Hirse gegen Schäden von Metolachlor bekannt ist. ) Wirkstoffe aus der Klasse der Isothiochromanone (S12), wie z.B. Methyl- [(3 -oxo-lH-2- benzothiopyran-4(3H)-yliden)methoxy]acetat (CAS-Reg.Nr. 205121-04-6) (S12-1) und verwandte Verbindungen aus WO-A-1998/13361. ) Eine oder mehrere Verbindungen aus Gruppe (S13): "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. ) Active ingredients from the class of isothiochromanones (S12), such as methyl- [(3-oxo-lH-2-benzothiopyran-4 (3H) -ylidene) methoxy] acetate (CAS reg. No. 205121-04-6) (S12-1) and related compounds from WO-A-1998/13361. ) One or more connections from group (S13):
"Naphthalic anhydrid" (l,8-Naphthalindicarbonsäureanhydrid) (S13-1), das als Saatbeiz-Safener für Mais gegen Schäden von Thiocarbamatherbiziden bekannt ist, "Naphthalic anhydride" (1,8-naphthalenedicarboxylic anhydride) (S13-1), which is known as a seed dressing safener for maize against damage from thiocarbamate herbicides,
"Fenclorim" (4,6-Dichlor-2-phenylpyrimidin) (S13-2), das als Safener für Pretilachlor in gesätem Reis bekannt ist, "Fenclorim" (4,6-dichloro-2-phenylpyrimidine) (S13-2), which is 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  (4-Carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid) (S13-4) from American
Cyanamid, das als Safener für Mais gegen Schäden von lmidazolinonen bekannt ist,  Cyanamide, known as a safener for corn 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 "Disulfoton" (O,O-Diethyl S-2-ethylthioethyl phosphordithioat) (S13-7),  (2-propenyl l-oxa-4-azaspiro [4.5] decane-4-carbodithioate) (S13-6) from Nitrokemia "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). ) 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). ) Active substances which, in addition to a herbicidal action against harmful plants, also have 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,  "Dimepiperate" or "MY-93" (S- 1 -methyl-1-phcnylcthyl-pipcridin-1-carbothioate), which is known as a safener for rice against damage to the herbicide Molinate,
"Daimuron" oder "SK 23" (l-(l-Methyl-l-phenylethyl)-3-p-tolyl-hamstoff), das als Safener für Reis gegen Schäden des Herbizids Imazosulfuron bekannt ist, "Daimuron" or "SK 23" (l- (l-methyl-l-phenylethyl) -3-p-tolylurea), which is known as a safener for rice against damage to the herbicide imazosulfuron,
"Cumyluron" = "JC-940" (3-(2-Chlorphenylmethyl)-l-(l-methyl-l-phenyl-ethyl)hamstoff, siehe JP-A-60087270), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Methoxyphenon" oder "NK 049" (3,3'-Dimethyl-4-methoxy-benzophenon), das als Safener für Reis gegen Schäden einiger Herbizide bekannt ist, "Cumyluron" = "JC-940" (3- (2-chlorophenylmethyl) -l- (l-methyl-l-phenyl-ethyl) urea, see JP-A-60087270), which acts as a safener for rice against damage to some herbicides is known "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. S15) Verbindungen der Formel (S15) oder deren Tautomere, "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) compounds of the formula (S15) or their tautomers,
Figure imgf000130_0001
wie sie in der WO-A-2008/131861 und WO-A-2008/131860 beschrieben sind, worin
Figure imgf000130_0001
as described in WO-A-2008/131861 and WO-A-2008/131860, in which
RH1 einen (Ci-C6)Haloalkylrest bedeutet und RH 2 Wasserstoff oder Halogen bedeutet und RH 1 represents a (Ci-C 6 ) haloalkyl radical and R H 2 represents 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-C i)Haloalkoxy, (Ci-C ijAlkylthio, (Ci-C ijAlkylamino, Di[(Ci-C4)alkyl]-amino, [(Ci-C i)Alkoxy]- carbonyl, [(Ci-C tjHaloalkoxyj-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 gesätigten oder ungesättigten carbocyclischen Ring kondensiert ist, oder (C4-C6)Cycloalkenyl, das an einer Seite des Rings mit einem 4 bis 6-gliedrigen gesätigten oder ungesätigten 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)Al oxy, (Ci-C4)Haloalkoxy, (Ci-C4)Alkylthio, (Ci-C4)Alkylamino, Di[(Ci- C4)alkyl]-amino, [(Ci-C4)Alkoxy]-carbonyl, [(Ci-C4)Haloalkoxy]-carbonyl, (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-C i) haloalkoxy, (Ci C ij alkylthio, (Ci-C ij alkylamino, di [(Ci-C4) alkyl] amino, [(Ci-C i) alkoxy] carbonyl, [(Ci-C t j haloalkoxyj-carbonyl, (C3-C6) cycloalkyl, which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted, or (C3-C6) cycloalkyl, (C4-C6) cycloalkenyl, (C3-C6) cycloalkyl, which is one side of the ring is fused with a 4 to 6 membered saturated or unsaturated carbocyclic ring, or (C4-C6) cycloalkenyl fused to one side of the ring with a 4 to 6 membered saturated or unsaturated carbocyclic ring, each the latter 4 residues unsubstituted or by one or more residues from the group halogen, hydroxy, cyano, (Ci-C4) alkyl, (Ci-C4) haloa lkyl, (Ci-C 4 ) Al oxy, (Ci-C 4 ) haloalkoxy, (Ci-C 4 ) alkylthio, (Ci-C 4 ) alkylamino, di [(Ci-C 4 ) alkyl] -amino, [(Ci C 4 ) alkoxy] carbonyl, [(Ci-C 4 ) 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  (C3-C6) cycloalkyl which is unsubstituted or substituted, phenyl which is unsubstituted or substituted and heterocyclyl which is unsubstituted or substituted is substituted or
RH 3 (Ci-C4)-Alkoxy, (C2-C4)Alkenyloxy, (C2-C6)Alkinyloxy oder (C2-C4)Haloalkoxy bedeutet und RH 4 Wasserstoff oder (Ci-C4)-Alkyl bedeutet oder R H 3 is (Ci-C 4 ) alkoxy, (C2-C 4 ) alkenyloxy, (C2-C6) alkynyloxy or (C2-C 4 ) haloalkoxy and R H 4 is hydrogen or (Ci-C 4 ) alkyl or
RH 3 und RH 4 zusammen mit dem direkt gebundenen N-Atom einen vier- bis achtgliedrigen R H 3 and R H 4 together with the directly bound N atom form a four- to eight-membered group
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, may 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 C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) alkoxy, (Ci-C 4 ) haloalkoxy and (Ci-C 4 ) alkylthio is substituted.
S16) Wirkstoffe, die vorrangig als Herbizide eingesetzt werden, jedoch auch Safenerwirkung auf Kulturpflanzen aufweisen, z. B. S16) Active ingredients which are primarily used as herbicides, but also have safener action on crops, for. B.
(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).
Bevorzugte Safener in Kombination mit den erfindungsgemäßen Verbindungen der Formel (I) und/oder deren Salze, insbesondere mit den Verbindungen der Formeln (1.1) bis (1.82) und/oder deren Salze sind: Cloquintocet-mexyl, Cyprosulfamid, Fenchlorazol-ethylester, Isoxadifen-ethyl, Mefenpyr-diethyl, Fenclorim, Cumyluron, S4-1 und S4-5, und besonders bevorzugte Safener sind: Cloquintocet-mexyl, Cyprosulfamid, Isoxadifen-ethyl und Mefenpyr-diethyl. Biologische Beispiele Preferred safeners in combination with the compounds of the formula (I) and / or their salts, in particular with the compounds of the formulas (1.1) to (1.82) and / or their salts, are: cloquintocet-mexyl, cyprosulfamide, ethyl fenchlorazole, isoxadifene -ethyl, mefenpyr-diethyl, fenclorim, cumyluron, S4-1 and S4-5, and particularly preferred safeners are: cloquintocet-mexyl, cyprosulfamide, isoxadifen-ethyl and mefenpyr-diethyl. Biological examples
Herbizide Wirkung im frühen Nachauflauf Herbicidal effects in the early post-emergence
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  Seeds of monocotyledonous or dicotyledonous weed plants were placed 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 treated with a
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.  The amount of water applied is equivalent to 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.
In den nachstehenden Tabllen Al bis A7 sind die Wirkungen ausgewählter Verbindungen der allgemeinen Formel (I) gemäß der Tabellen 1.1 bis 1.82 auf verschiedene Schadpflanzen und einer Aufwandmenge entsprechend 1900 g/ha, die gemäß zuvor genannter Versuchvorschrift erhalten wurden, dargestellt. The following tables A1 to A7 show the effects of selected compounds of the general formula (I) according to Tables 1.1 to 1.82 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 Table Al
Figure imgf000132_0001
Figure imgf000132_0001
Figure imgf000133_0001
Figure imgf000133_0001
Tabelle A2
Figure imgf000133_0002
Table A2
Figure imgf000133_0002
Figure imgf000134_0001
Figure imgf000134_0001
Tabelle A3
Figure imgf000134_0002
Table A3
Figure imgf000134_0002
Figure imgf000135_0001
Figure imgf000135_0001
Tabelle A4
Figure imgf000135_0002
Figure imgf000136_0001
Table A4
Figure imgf000135_0002
Figure imgf000136_0001
Tabelle A5
Figure imgf000136_0002
Tabelle A6 Table A5
Figure imgf000136_0002
Table A6
Figure imgf000137_0001
Figure imgf000137_0001
Tabelle A7 Table A7
Figure imgf000137_0002
Figure imgf000137_0002
Wie die Ergebnisse zeigen, weisen erfindungsgemäße Verbindungen, wie beispielsweise die As the results show, compounds according to the invention, such as the
Verbindungen Nr. 1.2-12, 1.2-13, 1.5-12, 1.6-13, 1.51-12, 1.5-13, 1.74-13, 1.54-13, 1.57-13, 1.57-12, 1.54- 12, 1.56-12, 1.66-12, 1.67-12, 1.77-12, 1.74-12, 1.77-13, 1.67-13 und 1.64-13 bei Behandlung im  Compounds No. 1.2-12, 1.2-13, 1.5-12, 1.6-13, 1.51-12, 1.5-13, 1.74-13, 1.54-13, 1.57-13, 1.57-12, 1.54-12, 1.56-12 , 1.66-12, 1.67-12, 1.77-12, 1.74-12, 1.77-13, 1.67-13 and 1.64-13 when treated in
Nachauflauf eine gute herbizide Wirksamkeit gegen Schadpflanzen auf.  Post-emergence a good herbicidal activity against harmful plants.
Beispielsweise haben dabei die Verbindungen Nr. 1.2-12, 1.2-13, 1.5-12, 1.6-13, 1.51-12, 1.5-13, 1.74-13, 1.54-13, 1.57-13, 1.57-12, 1.54-12, 1.66-12, 1.67-12, 1.77-12, 1.74-12, 1.77-13, 1.67-13, 1.64-13, 1.64-12, 1.76-12, 1.64-32, 1.74-32, 1.77-37, 1.67-37, 1.57-37, 1.66-37 und 1.64-13 im Nachauflaufverfahren eine gute herbizide Wirkung gegen die Schadpflanze Agrostis tenuis, die Verbindungen 1.2-13, 1.5-12, 1.6-13, 1.51-12, , 1.5-13, 1.57-13, 1.57-12, 1.54-12, 1.56-12, 1.67-12, 1.77-12, 1.74-12, 1.64-12, 1.77-37, 1.67-37, For example, compounds no. 1.2-12, 1.2-13, 1.5-12, 1.6-13, 1.51-12, 1.5-13, 1.74-13, 1.54-13, 1.57-13, 1.57-12, 1.54-12 , 1.66-12, 1.67-12, 1.77-12, 1.74-12, 1.77-13, 1.67-13, 1.64-13, 1.64-12, 1.76-12, 1.64-32, 1.74-32, 1.77-37, 1.67 -37, 1.57-37, 1.66-37 and 1.64-13 in the post-emergence process a good herbicidal action against the harmful plant Agrostis tenuis, the compounds 1.2-13, 1.5-12, 1.6-13, 1.51-12,, 1.5-13, 1.57 -13, 1.57-12, 1.54-12, 1.56-12, 1.67-12, 1.77-12, 1.74-12, 1.64-12, 1.77-37, 1.67-37,
1.57-37, 1.66-37 und 1.67-13 eine gute herbizide Wirkung gegen die Schadpflanze Lolium perenne, und die Verbindungen 1.2-13, 1.5-12, 1.5-13 und 1.51-12 eine gute herbizide Wirkung gegen die 1.57-37, 1.66-37 and 1.67-13 a good herbicidal action against the harmful plant Lolium perenne, and the compounds 1.2-13, 1.5-12, 1.5-13 and 1.51-12 a good herbicidal action against the
Schadpflanze Veronica persica, jeweils bei einer Aufwandmenge von 1900 g Aktivsubstanz pro Hektar.  Harmful plant Veronica persica, each with an application rate of 1900 g of active substance per hectare.

Claims

Patentansprüche Claims
1. Verwendung von substituierten 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamiden der 1. Use of substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides
allgemeinen Formel (I) oder deren Salze als herbizide Wirkstoffe  general formula (I) or their salts as herbicidal active ingredients
Figure imgf000138_0001
Figure imgf000138_0001
worin  wherein
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Q represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, R1 für (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl steht, Z represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 , R 1 for (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- ( Ci-C 8 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci-C8)- Alkyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl, Aryl, Aryl-(Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Haloalkyl, (C3-C8)- Halocycloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C8)- Cycloalkyloxy, Hydroxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Cyanoalkylaminocarbonyl, (C2-C8)- Alkenylaminocarbonyl, (C2-C8)-Alkynylaminocarbonyl, (Ci-C8)-Alkylamino, (Ci-C8)- Alkylthio, (Ci-C8)-Haloalkylthio, Hydrothio, (Ci-C8)-Bisalkylamino, (C3-C8)- Cycloalkylamino, (Ci-C8)-Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Formylamino, (Ci-C8)-Haloalkylcarbonylamino, (Ci-C8)-Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (Ci-C8)-Dialkyl-aminocarbonylamino, (Ci-C8)- Alkylsulfonylamino, (C3-C8)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8 ) alkyl, (C 3- C 8 ) cycloalkyl, (C 2 -C 8 ) alkenyl, (C 2 - C 8 ) -alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C 2 -C 8 ) -alkenyl, aryl- (C 2 -C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, heteroaryl, (Ci-C 8 ) - alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) - Halocycloalkyl, (Ci-C 8 ) alkoxy, (Ci-C 8 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 8 ) cycloalkyloxy, hydroxy, (C 3 -C 8 ) cycloalkyl- (Ci-C 8 ) -alkoxy, (Ci-C 8 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) - cycloalkylaminocarbonyl, (Ci-C 8 ) -cyanoalkylaminocarbonyl, (C 2 - C 8 ) alkenylaminocarbonyl, (C 2 -C 8 ) alkynylaminocarbonyl, (Ci-C 8 ) alkylamino, (Ci-C 8 ) alkylthio, (Ci-C 8 ) haloalkylthio, hydrothio, (Ci-C 8 ) -Bisalkylamino, (C 3 -C 8 ) -cycloalkylamino, (Ci-C 8 ) -alkylcarbonylamino, (C 3 -C 8 ) -cycloalkylcarbonylamino, formylamino, (Ci-C 8 ) -haloalkylcarbo nylamino, (Ci-C8) alkoxycarbonylamino, (Ci-C8) alkylaminocarbonylamino, (Ci-C 8) -dialkyl-aminocarbonylamino, (Ci-C 8) - alkylsulfonylamino, (C 3 -C 8) -Cycloalkylsulfonylamino, Arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C8)-Aminohaloalkylsulfonyl, (Ci-C8)- Alkylaminosulfonyl, (Ci-C8)-Bisalkylaminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)-Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C8)-Alkylsulfmyl, (C3-C8)-Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C8)-Dialkylsulfonimidoyl, S-(Ci-C8)- Alkylsulfonimidoyl, (Ci-C8)-Alkylsulfonylaminocarbonyl, (C3-C8)- Cycloalkylsulfonylaminocarbonyl, (C3-C8)-Cycloalkylaminosulfonyl, Aryl-(Ci-C8)- alkylcarbonylamino, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylcarbonylamino, Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 8) -Aminohaloalkylsulfonyl, (Ci-C 8) - alkylaminosulfonyl, (Ci-C 8) -Bisalkylaminosulfonyl, (C 3 -C 8) -Cycloalkylaminosulfonyl, (Ci-C 8) -Haloalkylaminosulfonyl, Arylaminosulfonyl, aryl- (Ci-C 8 ) -alkylaminosulfonyl, (Ci-C 8 ) -alkylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, arylsulfonyl, (Ci-C 8 ) -alkylsulfmyl, (C 3 -C 8 ) cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C8) -Dialkylsulfonimidoyl, S- (Ci-C8) - Alkylsulfonimidoyl, (Ci-C 8) -Alkylsulfonylaminocarbonyl, (C 3 -C 8) - Cycloalkylsulfonylaminocarbonyl, (C 3 -C 8 ) -cycloalkylaminosulfonyl, aryl- (Ci-C 8 ) -alkylcarbonylamino, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkylcarbonylamino,
Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, (Ci-C8)- Hydroxyalkylcarbonylamino, (Ci-C8)-Trialkylsilyl steht. Heteroarylcarbonylamino, (Ci-C 8) alkoxy (Ci-C8) alkylcarbonylamino, (Ci-C 8) - Hydroxyalkylcarbonylamino, (Ci-C 8) is trialkylsilyl.
2. Verwendung gemäß Anspruch 1, wobei in Formel (I) 2. Use according to claim 1, wherein in formula (I)
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-lO-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Q represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-lO-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Z represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (Ci-C4)-Cyanoalkyl, (Ci-C4)-Alkoxy-(Ci-C4)- alkyl, Aryl-(Ci-C i)-alkyl, Heteroaryl-(Ci-C i)-alkyl, Heterocyclyl-(Ci-C4)-alkyl, (C3-C6)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C4)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C4)-alkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkynyl steht, R 1 for (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkyl, (Ci-C 4 ) cyanoalkyl, (Ci-C 4 ) alkoxy- (Ci-C 4 ) alkyl, aryl- (Ci-C i) -alkyl, heteroaryl- (Ci-C i) -alkyl, heterocyclyl- (Ci-C4) -alkyl, (C3-C6) - cycloalkyl, (C3-C 6 ) -cycloalkyl- (Ci C 4 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl (Ci-C 4 ) alkyl, (C2-C 4 ) alkenyl, (C2-C 4 ) -Alkynyl stands,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, Isothiocyanato, Halogen, (CI-CÖ)- Alkyl, (C3-C6)-Cycloalkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkynyl, Aryl, Aryl-(Ci-C6)-alkyl, Aryl-(C2-C6)-alkenyl, Aryl-(C2-C6)-alkinyl, Aryl-(Ci-C6)-alkoxy, Heteroaryl, (CI-CÖ)- Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Hydroxyalkyl, (Ci-C6)-Haloalkyl, (C3-C6)- Halocycloalkyl, (Ci-Cr,)-Alkoxy, (Ci-Cr,)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C6)- Cycloalkyloxy, Hydroxy, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxy, (Ci-C6)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-Cr,)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, (Ci-C6)-Cyanoalkylaminocarbonyl, (C2-CÖ)- Alkenylaminocarbonyl, (C2-C6)-Alkynylaminocarbonyl, (Ci-Cej-Alkylamino, (CI-CÖ)- Alkylthio, (Ci-Cej-Haloalkylthio, Hydrothio, (Ci-Cej-Bisalkylamino, (C3-C6)- Cycloalkylamino, (Ci-Cej-Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Formylamino, (Ci-Cej-Haloalkylcarbonylamino, (Ci-Cej-Alkoxycarbonylamino, (Ci-Cej-Alkylaminocarbonylamino, (Ci-Cej-Dialkyl-aminocarbonylamino, (CI-CÖ)- Alkylsulfonylamino, (C3-C6)-Cycloalkylsulfonylamino, Arylsulfonylamino, Heteroarylsulfonylamino, Aminosulfonyl, (Ci-Cej-Aminoalkylsulfonyl, (CI-CÖ)- Alkylaminosulfonyl, (Ci-Cej-Bisalkylaminosulfonyl, (C3-C6)-Cycloalkylaminosulfonyl, (Ci-Cej-Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C6)-alkylaminosulfonyl, (Ci-Cej-Alkylsulfonyl, (Cs-Cej-Cycloalkylsulfonyl, Arylsulfonyl, (C 1 -Cr,)- Alkylsulfinyl, (C3-C6)-Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C6)-Dialkylsulfonimidoyl, S-(Ci-C6)- Alkylsulfonimidoyl, (Ci-Cej-Alkylsulfonylaminocarbonyl, (C3-C6)- Cycloalkylsulfonylaminocarbonyl, (C3-C6)-Cycloalkylaminosulfonyl, Aryl-(Ci-C6)- alkylcarbonylamino, (C3-C6)-Cycloalkyl-(Ci-C6)-alkylcarbonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C I -C Ö ) alkyl, (C 3- C 6 ) cycloalkyl, (C2-C6) alkenyl, (C2-C6) -Alkynyl, aryl, aryl- (Ci-C 6 ) -alkyl, aryl- (C2-C6) -alkenyl, aryl- (C2-C6) -alkynyl, aryl- (Ci-C 6 ) -alkoxy, heteroaryl, ( C I -C Ö ) - alkoxy- (Ci-C 6 ) -alkyl, (Ci-C 6 ) -hydroxyalkyl, (Ci-C 6 ) -haloalkyl, (C 3 -C 6 ) - halocycloalkyl, (Ci-Cr ,) - alkoxy, (Ci-Cr,) - haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 6 ) - cycloalkyloxy, hydroxy, (C 3 -C 6 ) -cycloalkyl- (Ci-C 6 ) -alkoxy, ( Ci-C 6 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-Cr,) - alkylaminocarbonyl, (C 3 -C 6 ) - Cycloalkylaminocarbonyl, (Ci-C 6 ) -cyanoalkylaminocarbonyl, (C2-C Ö ) - alkenylaminocarbonyl, (C2-C6) -alkynylaminocarbonyl, (Ci-Cej-alkylamino, (C I -C Ö ) - alkylthio, (Ci-Cej- Haloalkylthio, hydrothio, (Ci-Cej-bisalkylamino, (C3-C6) - cycloalkylamino, (Ci-Cej-alkylcarbonylamino, (C3-C6) -cycloalkylcarbonylamino, formylamino, (Ci-Cej-haloalkylcarbonylamino, (Ci-Cej-alkoxycarbonylamino, (Ci-Cej-alkylaminocarbonylamino, (Ci-Cej-dialkyl-aminocarbonylamino, (C I -C Ö) - alkylsulfonylamino, (C3-C6) -Cycloalkylsulfonylamino, arylsulfonylamino, Heteroarylsulfonylamino, aminosulfonyl, (Ci-Cej-Aminoalkylsulfonyl, (C I -C Ö ) - alkylaminosulfonyl, (Ci-Cej-bisalkylaminosulfonyl, (C3-C6) -cycloalkylaminosulfonyl, (Ci-Cej-haloalkylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C 6 ) -alkylaminosulfonyl, (Ci-Cej-alkylsulfonyl, ( Cs-Cej-cycloalkylsulfonyl, arylsulfonyl, (C 1 -Cr,) - alkylsulfinyl, (C3-C6) -cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 6 ) -dialkylsulfonimidoyl, S- (Ci-C 6 ) - Alkylsulfonimidoyl, (Ci -Cej-alkylsulfonylaminocarbonyl, (C3-C6) -cycloalkylsulfonylaminocarbonyl, (C3-C6) -cycloalkylaminosulfonyl, aryl- (Ci-C 6 ) -alkylcarbonylamino, (C3-C6) -cycloalkyl- (Ci-C6) -alkylcarbonylamino,
Heteroarylcarbonylamino, (Ci-C6)-Alkoxy-(Ci-C6)-alkylcarbonylamino, (CI-CÖ)- Hydroxyalkylcarbonylamino, (Ci-Cöj-Trialkylsilyl steht. Heteroarylcarbonylamino, (Ci-C6) alkoxy (Ci-C6) alkylcarbonylamino, (C I -C Ö) - Hydroxyalkylcarbonylamino, (Ci-C-j ö trialkylsilyl.
3. Verwendung gemäß Anspruch 1, wobei in Formel (I) 3. Use according to claim 1, wherein in formula (I)
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Q represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Z represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10 membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms consists independently of one another of up to 2 O, up to 2 S and up to 5 N atoms, where up to three carbon ring atoms can be selected independently of one another from the groups C (= 0) and C (= S), and the sulfur ring atoms can additionally be selected from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0), and each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C3)-Alkyl, (Ci-C3)-Haloalkyl, (Ci-C3)-Cyanoalkyl, (Ci-C3)-Alkoxy-(Ci-C3)- alkyl, Aryl-(Ci-C3)-alkyl, Heteroaryl-(Ci-C3)-alkyl, Heterocyclyl-(Ci-C3)-alkyl, (C3-Ce)- Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C3)-alkyl, (C3-C6)-Halocycloalkyl, (C3-C6)- Halocycloalkyl-(Ci-C3)-alkyl, (C2-C4)-Alkenyl, (C2-C i)-Alkynyl steht, R 1 for (Ci-C 3 ) -alkyl, (Ci-C 3 ) -haloalkyl, (Ci-C 3 ) -cyanoalkyl, (Ci-C 3 ) -alkoxy- (Ci-C 3 ) -alkyl, aryl- (Ci-C 3 ) -alkyl, heteroaryl- (Ci-C 3 ) -alkyl, heterocyclyl- (Ci-C 3 ) -alkyl, (C 3 -Ce) - cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (Ci-C 3 ) alkyl, (C 3 -C 6 ) halocycloalkyl, (C 3 -C 6 ) halocycloalkyl- (Ci-C 3 ) alkyl, (C 2 -C 4 ) alkenyl, (C 2 -C i) alkynyl,
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (C1-C4)- Alkyl, (C3-C5)-Cycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Alkynyl, Aryl, Aryl-(Ci-C4)-alkyl, Aryl-(C2-C3)-alkenyl, Aryl-(C2-C3)-alkinyl, Aryl-(Ci-C4)-alkoxy, Heteroaryl, (C1-C4)- Alkoxy-(Ci-C4)-alkyl, (Ci-C4)-Hydroxyalkyl, (Ci-C4)-Haloalkyl, (C3-C5)- Halocycloalkyl, (Ci-C4)-Alkoxy, (Ci-C4)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-Cs)- Cycloalkyloxy, Hydroxy, (C3-C5)-Cycloalkyl-(Ci-C4)-alkoxy, (Ci-C4)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C4)-Alkylaminocarbonyl, (C3-Cs)- Cycloalkylaminocarbonyl, (Ci-C4)-Cyanoalkylaminocarbonyl, (C2-C4)- Alkenylaminocarbonyl, (C2-C4)-Alkynylaminocarbonyl, (Ci-C4)-Alkylamino, (C1-C4)- Alkylthio, (Ci-C4)-Haloalkylthio, Hydrothio, (Ci-C4)-Bisalkylamino, (C3-Cs)- Cycloalkylamino, (Ci-C4)-Alkylcarbonylamino, (C3-C5)-Cycloalkylcarbonylamino, Formylamino, (Ci-C4)-Haloalkylcarbonylamino, (Ci-C4)-Alkoxycarbonylamino, (Ci-C4)-Alkylaminocarbonylamino, (Ci-C4)-Dialkylaminocabonylamino, (C1-C4)- Alkylsulfonylamino, (C3-C5)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (C 1 -C 4 ) alkyl, (C 3 -C 5 ) cycloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) alkynyl, aryl, aryl- (Ci-C 4 ) -alkyl, aryl- (C 2 -C 3 ) -alkenyl, aryl- (C 2 -C 3 ) -alkynyl, aryl- (Ci-C 4 ) -alkoxy, heteroaryl, (C 1 -C 4 ) -alkoxy- (Ci-C 4 ) -alkyl, (Ci-C 4 ) -hydroxyalkyl, (Ci-C 4 ) -haloalkyl, (C 3 -C 5 ) - Halocycloalkyl, (Ci-C 4 ) -alkoxy, (Ci-C 4 ) -haloalkoxy, aryloxy, heteroaryloxy, (C 3 -Cs) - cycloalkyloxy, hydroxy, (C 3 -C 5 ) -cycloalkyl- (Ci- C 4 ) -alkoxy, (Ci-C 4 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 4 ) -alkylaminocarbonyl, (C 3 -Cs) - cycloalkylaminocarbonyl, (Ci-C 4 ) -cyanoalkylaminocarbonyl, (C 2 - C 4 ) alkenylaminocarbonyl, (C 2 -C 4 ) alkynylaminocarbonyl, (Ci-C 4 ) alkylamino, (C 1 -C 4 ) alkylthio, (Ci-C 4 ) haloalkylthio, hydrothio, (Ci-C 4 ) -Bisalkylamino, (C 3 -Cs) -cycloalkylamino, (Ci-C 4 ) -alkylcarbonylamino, (C 3 -C 5 ) -cycloalkylcarbonylamino, formylamino, (Ci-C 4 ) -haloalkylcarbo nylamino, (Ci-C 4 ) -alkoxycarbonylamino, (Ci-C 4 ) -alkylaminocarbonylamino, (Ci-C 4 ) -dialkylaminocabonylamino, (C 1 -C 4 ) -alkylsulfonylamino, (C 3 -C 5 ) -cycloalkylsulfonylamino, arylsulfonylamino ,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C4)-Aminoalkylsulfonyl, (C1-C4)- Alkylaminosulfonyl, (Ci-C4)-Bisalkylaminosulfonyl, (C3-C5)-Cycloalkylaminosulfonyl, (Ci-C4)-Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C4)-alkylaminosulfonyl, (Ci-C4)-Alkylsulfonyl, (C3-C5)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C4)-Alkylsulfinyl, (C3-C5)-Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C4)-Dialkylsulfonimidoyl, S-(Ci-C4)- Alkylsulfonimidoyl, (Ci-C4)-Alkylsulfonylaminocarbonyl, (C3-Cs)- Cycloalkylsulfonylaminocarbonyl, (C3-C5)-Cycloalkylaminosulfonyl, Aryl-(Ci-C4)- alkylcarbonylamino, (C3-C5)-Cycloalkyl-(Ci-C4)-alkylcarbonylamino, Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 4) -Aminoalkylsulfonyl, (C 1 -C 4) - alkylaminosulfonyl, (Ci-C 4) -Bisalkylaminosulfonyl, (C 3 -C 5) -Cycloalkylaminosulfonyl, (Ci-C 4) -Haloalkylaminosulfonyl , Arylaminosulfonyl, aryl- (Ci-C 4 ) -alkylaminosulfonyl, (Ci-C 4 ) -alkylsulfonyl, (C 3 -C 5 ) -cycloalkylsulfonyl, arylsulfonyl, (Ci-C 4 ) -alkylsulfinyl, (C 3 -C 5 ) cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 4) -Dialkylsulfonimidoyl, S- (Ci-C4) - Alkylsulfonimidoyl, (Ci-C 4) -Alkylsulfonylaminocarbonyl, (C 3 -Cs) - Cycloalkylsulfonylaminocarbonyl, (C 3 -C 5 ) -cycloalkylaminosulfonyl, aryl- (Ci-C 4 ) -alkylcarbonylamino, (C 3 -C 5 ) -cycloalkyl- (Ci-C 4 ) -alkylcarbonylamino,
Heteroarylcarbonylamino, (Ci-C4)-Alkoxy-(Ci-C4)-alkylcarbonylamino, (C1-C4)- Hydroxyalkylcarbonylamino, (Ci-C4)-Trialkylsilyl steht. Heteroarylcarbonylamino, (Ci-C 4 ) -alkoxy- (Ci-C 4 ) -alkylcarbonylamino, (C 1 -C 4 ) - hydroxyalkylcarbonylamino, (Ci-C 4 ) -trialkylsilyl.
4. Verwendung gemäß Anspruch 1, wobei in Formel (I) Q für die Gruppen Q- 1.1 bis Q- 10.144. Use according to claim 1, wherein in formula (I) Q for the groups Q-1.1 to Q-10.14
Figure imgf000143_0001
Figure imgf000144_0001
Figure imgf000143_0001
Figure imgf000144_0001
Figure imgf000145_0001
Figure imgf000146_0001
Figure imgf000147_0001
Figure imgf000148_0001
Figure imgf000149_0001
steht, Z für die Gruppen Z-l .1 bis Z-4.3
Figure imgf000145_0001
Figure imgf000146_0001
Figure imgf000147_0001
Figure imgf000148_0001
Figure imgf000149_0001
stands, Z for groups Zl .1 to Z-4.3
Figure imgf000150_0001
Figure imgf000151_0001
steht, und
Figure imgf000150_0001
Figure imgf000151_0001
stands, and
R1 für Methyl, Ethyl, n-Propyl, Isopropyl, Cyclopropyl, Cyclopropylmethyl, Benzyl, p- Methoxy-benzyl, 2-Phenethyl, Allyl, Propargyl steht. R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxy-benzyl, 2-phenethyl, allyl, propargyl.
5. Herbizide Mitel, gekennzeichnet durch einen herbizid wirksamen Gehalt an mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4. 5. Herbicidal agents, characterized by a herbicidally active content of at least one compound of the general formula (I) according to one of claims 1 to 4.
6. Herbizide Mitel nach Anspruch 5 in Mischung mit Formulierungshilfsmitteln. 6. Herbicidal agents according to claim 5 in a mixture with formulation auxiliaries.
7. Herbizide Mitel nach Anspruch 5 oder 6, enthaltend mindestens einen weiteren pestizid 7. Herbicidal agent according to claim 5 or 6, containing at least one further pesticide
wirksamen Stoff aus der Gruppe Insektizide, Akarizide, Herbizide, Fungizide, Safener und W achstumsregulatoren.  active substance from the group insecticides, acaricides, herbicides, fungicides, safeners and growth regulators.
8. Herbizide Mitel nach einem der Ansprüche 5-7 weiter enthaltend mindestens einen Safener. 8. Herbicidal agent according to any one of claims 5-7 further containing at least one safener.
9. Herbizide Mitel nach Anspruch 8 enthaltend cyprosulfamid, cloquintocet-mexyl, mefenpyr- diethyl oder isoxadifen-ethyl. 9. Herbicidal agent according to claim 8 containing cyprosulfamide, cloquintocet-mexyl, mefenpyr-diethyl or isoxadifen-ethyl.
10. Verfahren zur Bekämpfung unerwünschter Pflanzen, dadurch gekennzeichnet, dass man eine wirksame Menge mindestens einer Verbindung der allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4 oder eines herbiziden Mittels nach einem der Ansprüche 5 bis 9 auf die Pflanzen oder auf den Ort des unerwünschten Pflanzenwachstums appliziert. 10. A method for controlling unwanted plants, characterized in that an effective amount of at least one compound of the general formula (I) according to one of claims 1 to 4 or a herbicidal composition according to one of claims 5 to 9 on the plants or on the site of unwanted plant growth applied.
11. Verfahren gemäß Anspruch 10, dadurch gekennzeichnet, dass die Verbindungen der 11. The method according to claim 10, characterized in that the compounds of
allgemeinen Formel (I) gemäß einem der Ansprüche 1 bis 4 zur Bekämpfung unerwünschter Pflanzen in Kulturen von Nutzpflanzen eingesetzt werden.  general formula (I) according to any one of claims 1 to 4 for controlling undesirable plants in crops of useful plants.
12. Verfahren gemäß Anspruch 11, dadurch gekennzeichnet, dass die Nutzpflanzen transgene 12. The method according to claim 11, characterized in that the crop plants are transgenic
Nutzpflanzen sind.  Crops are.
13. Substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide der Formel (I) 13. Substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides of the formula (I)
Figure imgf000152_0001
worin
Figure imgf000152_0001
wherein
Q für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Q represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, with each ring or ring system optionally with up to 5
Substituenten aus der Gruppe R2 substituiert ist, steht, Substituent from the group R 2 is substituted,
Z für ein gegebenenfalls substituiertes Aryl, Heteroaryl, steht, wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert sein kann; oder für einen gegebenenfalls substituierten 5-7-gliedrigen heterocyclischen Ring steht; oder für ein gegebenenfalls substituiertes 8-l0-gliedriges bicyclisches Ringsystem, in dem jeder Ring oder jedes Ringsystem aus Kohlenstoffatomen und 1-5 Heteroatomen besteht, die unabhängig voneinander bis zu 2 O-, bis zu 2 S- und bis zu 5 N-Atome enthalten, wobei bis zu drei Kohlenstoffringatome unabhängig voneinander aus den Gruppen C(=0) und C(=S) gewählt werden können, und die Schwefelringatome zusätzlich aus den Gruppen S, S(=0), S(=0)2, S(=NR1) und S(=NR1)(=0) gewählt werden können, und wobei jeder Ring oder jedes Ringsystem optional mit bis zu 5 Substituenten aus der Gruppe R2 substituiert ist, steht, Z represents an optionally substituted aryl, heteroaryl, where each ring or ring system can optionally be substituted with up to 5 substituents from the group R 2 ; or represents an optionally substituted 5-7 membered heterocyclic ring; or for an optionally substituted 8-10-membered bicyclic ring system in which each ring or ring system consists of carbon atoms and 1-5 heteroatoms which independently of one another have up to 2 O, up to 2 S and up to 5 N atoms contain, where up to three carbon ring atoms can be selected independently from the groups C (= 0) and C (= S), and the sulfur ring atoms additionally from the groups S, S (= 0), S (= 0) 2 , S (= NR 1 ) and S (= NR 1 ) (= 0) can be selected, and where each ring or ring system is optionally substituted with up to 5 substituents from the group R 2 ,
R1 für (Ci-C8)-Alkyl, (Ci-C8)-Haloalkyl, (Ci-C8)-Cyanoalkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Cycloalkyl-(Ci-C8)-alkyl, (C3-C8)-Halocycloalkyl, (C3-C8)-Halocycloalkyl-(Ci-C8)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl steht, und R 1 for (Ci-C 8 ) -alkyl, (Ci-C 8 ) -haloalkyl, (Ci-C 8 ) -cyanoalkyl, (Ci-C 8 ) -alkoxy- (Ci-C 8 ) -alkyl, aryl- (Ci-C 8 ) -alkyl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -Cio) cycloalkyl, (C 3 -Cio) cycloalkyl- ( Ci-C 8 ) -alkyl, (C 3 -C 8 ) -halocycloalkyl, (C 3 -C 8 ) -halocycloalkyl- (Ci-C 8 ) -alkyl, (C2-C 8 ) -alkenyl, (C2-C 8 ) -alkynyl, and
R2 für Wasserstoff, Nitro, Amino, Cyano, Thiocyanato, lsothiocyanato, Halogen, (Ci-C8)- Alkyl, (C3-C8)-Cycloalkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkynyl, Aryl, Aryl-(Ci-C8)-alkyl, Aryl-(C2-C8)-alkenyl, Aryl-(C2-C8)-alkinyl, Aryl-(Ci-C8)-alkoxy, Heteroaryl, (Ci-C8)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Hydroxyalkyl, (Ci-C8)-Haloalkyl, (C3-C8)- Halocycloalkyl, (Ci-C8)-Alkoxy, (Ci-C8)-Haloalkoxy, Aryloxy, Heteroaryloxy, (C3-C8)- Cycloalkyloxy, Hydroxy, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxy, (Ci-C8)-Alkoxycarbonyl, Hydroxycarbonyl, Aminocarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, (Ci-C8)-Cyanoalkylaminocarbonyl, (C2-C8)- Alkenylaminocarbonyl, (C2-C8)-Alkynylaminocarbonyl, (Ci-C8)-Alkylamino, (Ci-C8)- Alkylthio, (Ci-C8)-Haloalkylthio, Hydrothio, (Ci-C8)-Bisalkylamino, (C3-C8)- Cycloalkylamino, (Ci-C8)-Alkylcarbonylamino, (C3-C8)-Cycloalkylcarbonylamino, Formylamino, (Ci-C8)-Haloalkylcarbonylamino, (Ci-C8)-Alkoxycarbonylamino, (Ci-C8)-Alkylaminocarbonylamino, (Ci-C8)-Dialkyl-aminocarbonylamino, (Ci-Cs)- Alkylsulfonylamino, (C3-C8)-Cycloalkylsulfonylamino, Arylsulfonylamino, R 2 for hydrogen, nitro, amino, cyano, thiocyanato, isothiocyanato, halogen, (Ci-C 8 ) alkyl, (C 3 -C 8 ) cycloalkyl, (C2-C 8 ) alkenyl, (C2-C 8 ) -Alkynyl, aryl, aryl- (Ci-C 8 ) -alkyl, aryl- (C2-C 8 ) -alkenyl, aryl- (C2-C 8 ) -alkynyl, aryl- (Ci-C 8 ) -alkoxy, Heteroaryl, (Ci-C 8 ) - alkoxy- (Ci-C 8 ) -alkyl, (Ci-C 8 ) -hydroxyalkyl, (Ci-C 8 ) -haloalkyl, (C 3 -C 8 ) - halocycloalkyl, (Ci -C 8 ) alkoxy, (Ci-C 8 ) haloalkoxy, aryloxy, heteroaryloxy, (C 3 -C 8 ) cycloalkyloxy, hydroxy, (C 3 -C 8 ) cycloalkyl (Ci-C 8 ) alkoxy , (Ci-C 8 ) -alkoxycarbonyl, hydroxycarbonyl, aminocarbonyl, (Ci-C 8 ) -alkylaminocarbonyl, (C 3 -C 8 ) - cycloalkylaminocarbonyl, (Ci-C 8 ) -cyanoalkylaminocarbonyl, (C2-C 8 ) - alkenylaminocarbonyl , (C2-C 8 ) -alkynylaminocarbonyl, (Ci-C 8 ) -alkylamino, (Ci-C 8 ) -alkylthio, (Ci-C 8 ) -haloalkylthio, hydrothio, (Ci-C 8 ) -bisalkylamino, (C 3 -C 8 ) - Cycloalkylamino, (Ci-C 8 ) -alkylcarbonylamino, (C3-C8) -cycloalkylcarbonylamino, formylamino, (Ci-C 8 ) -haloalkylcarbonylamino, (Ci-C 8 ) -alkoxycarbonylamino, (Ci-C 8 ) -alkylaminocarbonylamino, (Ci -C 8 ) -dialkyl-aminocarbonylamino, (Ci-Cs) - alkylsulfonylamino, (C3-C8) -cycloalkylsulfonylamino, arylsulfonylamino,
Heteroarylsulfonylamino, Aminosulfonyl, (Ci-C8)-Aminohaloalkylsulfonyl, (Ci-Cs)-Heteroarylsulfonylamino, aminosulfonyl, (Ci-C 8 ) -aminohaloalkylsulfonyl, (Ci-Cs) -
Alkylaminosulfonyl, (Ci-C8)-Bisalkylaminosulfonyl, (C3-C8)-Cycloalkylaminosulfonyl, (Ci-C8)-Haloalkylaminosulfonyl, Arylaminosulfonyl, Aryl-(Ci-C8)-alkylaminosulfonyl, (Ci-C8)-Alkylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Arylsulfonyl, (Ci-C8)-Alkylsulfmyl, (C3-C8)-Cycloalkylsulfinyl, Arylsulfinyl, N,S-(Ci-C8)-Dialkylsulfonimidoyl, S-(Ci-C8)- Alkylsulfonimidoyl, (Ci-C8)-Alkylsulfonylaminocarbonyl, (C3-Cs)-Alkylaminosulfonyl, (Ci-C 8 ) -bisalkylaminosulfonyl, (C3-C8) -cycloalkylaminosulfonyl, (Ci-C 8 ) -haloalkylaminosulfonyl, arylaminosulfonyl, aryl- (Ci-C 8 ) -alkylaminosulfonyl, (Ci-C 8 ) -alkylsulfonyl, (C3-C8) cycloalkylsulfonyl, arylsulfonyl, (Ci-C 8 ) alkylsulfmyl, (C3-C8) cycloalkylsulfinyl, arylsulfinyl, N, S- (Ci-C 8 ) dialkylsulfonimidoyl, S- (Ci-C 8 ) - alkylsulfonimidoyl, (Ci-C 8 ) -alkylsulfonylaminocarbonyl, (C3-Cs) -
Cycloalkylsulfonylaminocarbonyl, (C3-C8)-Cycloalkylaminosulfonyl, Aryl-(Ci-C8)- alkylcarbonylamino, (C3-C8)-Cycloalkyl-(Ci-C8)-alkylcarbonylamino, Heteroarylcarbonylamino, (Ci-C8)-Alkoxy-(Ci-C8)-alkylcarbonylamino, (Ci-Cs)- Hydroxyalkylcarbonylamino, (Ci-C8)-Trialkylsilyl steht, ausgenommen der nachfolgend genannten Verbindungen: Cycloalkylsulfonylaminocarbonyl, (C3-C8) -cycloalkylaminosulfonyl, aryl- (Ci-C 8 ) -alkylcarbonylamino, (C3-C8) -cycloalkyl- (Ci-C8) -alkylcarbonylamino, heteroarylcarbonylamino, (Ci-C 8 ) -alkoxy- (Ci -C 8 ) -alkylcarbonylamino, (Ci-Cs) - hydroxyalkylcarbonylamino, (Ci-C 8 ) -trialkylsilyl, with the exception of the following compounds:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol- N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-
4-carboxamid (CAS [2043629-62-3]), und 4-carboxamide (CAS [2043629-62-3]), and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8]).  N- (2-Fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8]).
14. Substituierte 5-(Sulfanyl)-3,4-dihydro-2H-pyrrol-4-carboxamide gemäß Anspruch 13, worin in14. Substituted 5- (sulfanyl) -3,4-dihydro-2H-pyrrole-4-carboxamides according to claim 13, wherein in
Formel (I) Formula (I)
Q für die Gruppen Q- 1.1 bis Q- 10.14  Q for groups Q- 1.1 to Q- 10.14
Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000158_0001
Figure imgf000159_0001
Figure imgf000160_0001
Figure imgf000154_0001
Figure imgf000155_0001
Figure imgf000156_0001
Figure imgf000157_0001
Figure imgf000158_0001
Figure imgf000159_0001
Figure imgf000160_0001
Figure imgf000161_0001
Figure imgf000161_0001
steht,  stands,
Z für die Gruppen Z-l.l bis Z-4.3  Z for groups Z-l.l to Z-4.3
Figure imgf000161_0002
Figure imgf000161_0002
Figure imgf000162_0001
Figure imgf000163_0001
steht, und
Figure imgf000162_0001
Figure imgf000163_0001
stands, and
R1 für Methyl, Ethyl, n-Propyl, Isopropyl, Cyclopropyl, Cyclopropylmethyl, Benzyl, p- Methoxy-benzyl, 2-Phenethyl, Allyl, Propargyl steht, ausgenommen der nachfolgend genannten Verbindungen: R 1 represents methyl, ethyl, n-propyl, isopropyl, cyclopropyl, cyclopropylmethyl, benzyl, p-methoxy-benzyl, 2-phenethyl, allyl, propargyl, except for the compounds mentioned below:
N-(2-Fluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-56-5]), N- (2-fluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-56-5]),
N-(2,3-Difluorphenyl)-5-(methylsulfanyl)-3-[4-(trifluormethyl)phenyl]-3,4-dihydro-2H-pyrrol- 4-carboxamid (CAS [2043629-62-3]), und  N- (2,3-difluorophenyl) -5- (methylsulfanyl) -3- [4- (trifluoromethyl) phenyl] -3,4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-62-3]) , and
N-(2-Fluorphenyl)-5 -(methylsulfanyl)-3 - [3 -(trifluormethyl)phenyl] -3 ,4-dihydro-2H-pyrrol-4- carboxamid (CAS [2043629-33-8]).  N- (2-Fluorophenyl) -5 - (methylsulfanyl) -3 - [3 - (trifluoromethyl) phenyl] -3, 4-dihydro-2H-pyrrole-4-carboxamide (CAS [2043629-33-8]).
PCT/EP2019/073090 2018-09-24 2019-08-29 Substituted 5-(sulfanyl)-3,4-dihydro-2h-pyrrol-4-carboxamides and salts thereof and their use as herbicidal active substances WO2020064260A1 (en)

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