EP3128841A1 - Verwendung von substituierten oxotetrahydrochinolinylsulfonamiden oder deren salzen zur steigerung der stresstoleranz in pflanzen - Google Patents

Verwendung von substituierten oxotetrahydrochinolinylsulfonamiden oder deren salzen zur steigerung der stresstoleranz in pflanzen

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Publication number
EP3128841A1
EP3128841A1 EP15715709.0A EP15715709A EP3128841A1 EP 3128841 A1 EP3128841 A1 EP 3128841A1 EP 15715709 A EP15715709 A EP 15715709A EP 3128841 A1 EP3128841 A1 EP 3128841A1
Authority
EP
European Patent Office
Prior art keywords
alkyl
aryl
alkoxy
cycloalkyl
heteroaryl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP15715709.0A
Other languages
German (de)
English (en)
French (fr)
Inventor
Jens Frackenpohl
Guido Bojack
Hendrik Helmke
Stefan Lehr
Thomas Müller
Lothar Willms
Hansjörg Dietrich
Dirk Schmutzler
Rachel Baltz
Udo Bickers
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
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Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP3128841A1 publication Critical patent/EP3128841A1/de
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
    • 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
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
    • A01N25/04—Dispersions, emulsions, suspoemulsions, suspension concentrates or gels
    • A01N25/06—Aerosols
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
    • A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
    • C07D215/38—Nitrogen atoms

Definitions

  • the invention relates to the use of substituted ones
  • arylsulfonamides such as, for example, 2-cyanobenzenesulfonamides have insecticidal properties (compare, for example, EP0033984 and WO2005 / 035486, WO2006 / 056433, WO2007 / 060220).
  • 2-Cyanobenzenesulfone amides with particular heterocyclic substituents are described in EP2065370.
  • certain aryl- and heteroaryl-substituted sulfonamides can be used as active ingredients against abiotic plant stress (see WO201 1/1 13861).
  • Arylsulfonamides having alkylcarboxyl substituents as growth regulators, especially for limiting the growth length of rice and wheat plants with the aim of minimizing the weather-related kinking is described in DE2544859, while the fungicidal action of certain N-Cyanoalkylsulfonamide is described in EP176327. It is also known that substituted N-sulfonylaminoacetonitriles can be used to control parasites in warm-blooded animals (see WO2004 / 000798).
  • WO2013 / 148339 described.
  • WO2013 / 148339 likewise describes the agonistic action of the substances in question on abscisic acid receptors.
  • Hetarylsulfonamides can be used as pharmaceutical active ingredients.
  • WO2003 / 007931 likewise describes the pharmaceutical use of substituted naphthylsulfonamides, while in Eur. J. Med. Chem. 2010, 45, 1760 naphthylsulfonyl-substituted glutamic acid amides and their antitumor action are described. Effects on cancer stem cells are also described in WO2013 / 130603.
  • pyrrolidinyl-substituted arylsulfonamides can be used as cathepsin C inhibitors in the treatment of respiratory diseases (WO2009 / 026197) or as anti-infective agents in the treatment of hepatitis C (WO2007 / 092588).
  • Diabetes see WO2003 / 09121 1
  • analgesics see WO2008 / 131947
  • ⁇ -secretase modulators see WO2010 / 108067
  • the signal chain genes of the abiotic stress reaction include, among others. Transcription factors of classes DREB and CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106).
  • the response to salt stress involves phosphatases of the ATPK and MP2C types.
  • salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol. Biol. 57: 463-499).
  • sucrose synthase and proline transporters Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol. Biol. 57: 463-499.
  • Late Embryogenesis Abundant Proteins which include dehydrins as an important class, is known (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 700: 291-296). These are chaperones, the vesicles, proteins and
  • HSF Heat Shock Factors
  • HSP Heat Shock Proteins
  • Substances or their stable synthetic derivatives and derived structures are also effective in external application to plants or seed dressing and activate defense reactions that result in an increased stress or pathogen tolerance of the plant [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589].
  • naphthylsulfonamide (4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide) influences the germination of plant seeds in the same manner as abscisic acid (Park et al., Science 2009, 324, 1068-1071).
  • a naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline) exhibits a mode of action in biochemical receptor assays that react with 4-bromo-N- (pyridin-2-ylmethyl) naphthalene-1-sulfonamide is comparable (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1, 102-1 108).
  • osmolytes e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives
  • Xanthines for increasing the abiotic stress tolerance in plants has already been described (Bergmann et al., DD277832, Bergmann et al., DD277835).
  • the molecular causes of the anti-stress effects of these substances are largely unknown.
  • PARP poly-ADP-ribose polymerases
  • PARG poly (ADP-ribose) glycohydrolases
  • the object of the present invention was to provide compounds which further increase the tolerance to abiotic stress in plants, cause a strengthening of plant growth and / or contribute to the increase of the plant yield.
  • tolerance to abiotic stress for example, tolerance to cold, heat, Drought stress (stress caused by drought and / or lack of water), salting and flooding understood.
  • Oxotetrahydroquinolinylsulfonamides can be used to increase the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase plant yield.
  • the subject of the present invention is therefore the use of
  • R 1 is halogen, cyano, (C 3 -C 10 ) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 - C 8 ) -haloalkoxy, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 8 ) -alkylamino, bis [(C 1 C 8 ) -alkyl] amino, hydrothio,
  • R 7 and R 8 form an oxo group with the carbon atom to which they are attached, or
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, cyano,
  • (C 1 -C 8 ) -haloalkyl cyano- (C 1 -C 8 ) -alkyl, aryl, heteroaryl, (C 3 -C 8 ) -cycloalkyl, (C 8 -C 8 ) -cycloalkenyl, heterocyclyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl stand,
  • W is oxygen or sulfur
  • X, Y independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -haloalkyl, Hydroxy (C 1 -C 8 ) alkyl, cyano (C 1 -C 8 ) alkyl, aryl, heteroaryl, (C 3 -C 8 ) cycloalkyl, (C 2 -C 8 ) cycloalkenyl, heterocyclyl, cyano , Nitro, hydroxy, (C 1 -C 8 ) alkoxy, (C 1 -C 8 ) alkylthio, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, (C 1 -C 8 ) -alkenyl- (C 1 -C 8 ) -alkyl, ary
  • the compounds of general formula (I) may be prepared by addition of a suitable inorganic or organic acid, such as mineral acids such as HCl, HBr, H 2 SO 4 , HsPO 4 or HNO 3 , or organic acids, e.g.
  • a suitable inorganic or organic acid such as mineral acids such as HCl, HBr, H 2 SO 4 , HsPO 4 or HNO 3
  • organic acids e.g.
  • carboxylic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid to form a basic group such as amino, alkylamino, dialkylamino, piperidino, morpholino or pyridino, salts.
  • These salts then contain the conjugate base of the acid as an anion.
  • Suitable substituents which are in deprotonated form such as
  • Sulfonic acids certain sulfonic acid amides or carboxylic acids are present, internal salts can in turn form protonatable groups, such as amino groups.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine, and ammonium, alkali or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and
  • Hydrogen is replaced by a cation suitable for agriculture
  • metal salts in particular alkali metal salts or alkaline earth metal salts, in particular sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary ammonium salts, for example with cations of the formula [NR a R b R c R d ] + , wherein R a to Each R d is independently one
  • R 1 represents halogen, cyano, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) halocycloalkyl, (C 4 -C 10) - cycloalkenyl, (C 4 -C 10) -Halocycloalkenyl, (C 3 -C 10 ) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, aryl, aryl- (C 1 -C 7 ) -alkyl .
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 7 ) -alkoxy, (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkyl, (C 1 - C 7 ) -haloalkoxy, (C 1 -C 7 ) -alkylthio, (C 1 -C 7 ) -haloalkylthio, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 7 ) -alkylamino, bis - [(C 1 -C 7 ) -alkyl] amino,
  • R 7 and R 8 with the carbon atom to which they are attached form an oxo group or
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, cyano, (C 1 -C 7 ) -haloalkyl, cyano- (C 1 -C 7 ) -alkyl, aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C -C 7 ) -cycloalkenyl, heterocyclyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio - (C 1 -C 7 ) -alkyl,
  • W is oxygen or sulfur
  • X, Y independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -haloalkyl, Hydroxy (C 1 -C 7 ) alkyl, cyano (C 1 -C 7 ) alkyl, aryl, heteroaryl, (C 3 -C 7 ) cycloalkyl, (C 7 -C 7 ) cycloalkenyl, heterocyclyl, cyano , Nitro, hydroxy, (C 1 -C 7 ) alkoxy, (C 1 -C 7 ) alkylthio, (C 1 -C 7 ) alkoxy (C 1 -C 7 ) alkyl, (C 1 -C 7 ) -alkenyl (C 1 -C 7 ) -alkyl, aryl
  • R 1 represents fluorine, chlorine, bromine, iodine, cyano, (C 3 -C 10 ) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -cycloalkenyl, (C 4 -C 10 ) -Halocycloalkenyl, (C 3 -C 10 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 - C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 6 ) -alkylamino, bis - [(C 1 -C 6 ) -alkyl] amino
  • R 5 is amino, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl,
  • R 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, cyano- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl, heterocyclylsulfonyl, aryl- (C 1 -C 6 ) -alkylsulfonyl, (C 1 -C 6 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 3 -C 6 ) -cycloalkylcarbonyl, heterocyclylcarbonyl, (C 1 -C
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 6 ) -haloalkyl, cyano- (C 1 -C 6 ) - alkyl, aryl, heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, heterocyclyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -Al kylth io- (C 1 -C 6 ) -alcyl,
  • W is oxygen or sulfur, preferably oxygen
  • X, Y independently of one another are hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, (C 2 -C 6 ) -alkenyl, (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) - Cycloalkyl, (C -C 6 ) -cycloalkenyl,
  • R 1 represents fluorine, chlorine, bromine, iodine, cyano, (C 3 -C 10 ) -cycloalkyl, (C 3 -C 10 ) -halocycloalkyl, (C 4 -C 10 ) -cycloalkenyl, (C 4 -C 10 ) -Halocycloalkenyl, (C 3 -C 10 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl,
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 5 ) -alkoxy, (C 1 -C 5 ) -alkyl, (C 1 -C 5 ) -haloalkyl, (C 1 - C 5 ) -haloalkoxy, (C 1 -C 5 ) -alkylthio, (C 1 -C 5 ) -haloalkylthio, aryl, aryl- (C 1 -C 5 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 5 ) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 5 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 5 ) -alkylamino, bis - [(C 1 -C 5 ) -alkyl] amino,
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, fluorine, chlorine, bromine, iodine, cyano, (C 1 -C 6 ) -haloalkyl, cyano- (C 1 -C 6 ) - alkyl, aryl, heteroaryl, (C 3 -C 6 ) -cycloalkyl, (C 4 -C 6 ) -cycloalkenyl, heterocyclyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl,
  • W is oxygen or sulfur, preferably oxygen.
  • R 1 is fluorine, chlorine, bromine, iodine, preferably fluorine and chlorine, cyano, cyclopropyl,
  • Difluoromethyl fluoro-n-propyl, 2-fluoro-prop-2-yl, 1-fluoro-prop-2-yl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 1,1-difluoroethyl, 3, 3,3-trifluoropropyl, 4,4,4-trifluorobutyl, 3,3-difluoropropyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoroisopropyl, nonafluoro-n-butyl, chlorodifluoromethyl, bromodifluoromethyl,
  • Dichlorofluoromethyl bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, 2,2-dichloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, difluoro-tert-butyl, 2-bromo-1, 1, 2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, 1 , 2,2,2-Tetrafluoroethyl, 2-chloro-1, 1, 2-trifluoroethyl, 2-chloro-1, 1, 2,2-tetrafluoroethyl, 1, 2,2,3,3,3-hexafluoropropyl, 1 - methyl 2,2,2-trifluoroethyl, 1-chloro-2,2,2-trifluoroethyl, 2,2,3,3,3-pentafluoropropyl, 1, 2,2,3,3,4,4,4 octafluorobuty
  • Cyclobutylmethoxydifluoromethyl but-3-yn-1-yloxyethyl, pent-4-yn-1-yloxydifluoromethyl, hex-3-yn-1-ylxydifluoromethyl, but-3-yn-1-yl-oxydifluoromethyl, 2,2,2- trifluoroethoxydifluoromethyl, 3,3,3-trifluoropropoxydifluoromethyl, 4,4,4-trifluorobutoxyd iflormethyl, 3-chloro-1-methoxybut-3-yl, cyanomethyl,
  • Methoxy-n-pentyl 2-methoxy-2-methylpropyl, 2-methoxy-1-methylpropyl, ethoxymethyl, ethoxyethyl, ethoxy-n-propyl, ethoxy-iso-propyl, ethoxy-n-butyl, ethoxy-n-pentyl, 2-ethoxy-2-methylpropyl, 2-ethoxy-1-methylpropyl, n-propyloxymethyl, n-propyloxyethyl, n-propyloxy-n-propyl, n-propyloxy-isopropyl, n-propyloxy-n-butyl, 2- n-propyloxy-2-methylpropyl, 2-n-propyloxy-1-methylpropyl, iso -propyloxymethyl, iso -propyloxyethyl, iso-propyloxy-n-propyl, iso-propyloxy-iso
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, preferably fluorine and chlorine, methoxy, ethoxy, n-propyloxy, isopropoxy, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, Pentafluoroethyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy, 3,3,3-trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, optionally substituted phenyl, benzyl, phenylethyl, p-chlorophenylethyl, heteroaryl, heterocyclyl, cyclopropyl, cyclobutyl, nitro, hydroxy, Dimethylamino, diethylamino, formyl, hydroxyiminomethyl,
  • Triisopropylsilylethynyl 2-pyridylethynyl, 3-pyridylethynyl, 4-chloro-3-pyridylethynyl,
  • R 5 is amino, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl , 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3 -Di-methylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-e
  • Heterocyclyl- (C 2 -C 5 ) -alkenyl is hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neo -Pentyl, n-hexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
  • W is oxygen or sulfur, preferably oxygen.
  • Trifluoromethoxymethyl trifluoromethylthiomethyl, pentafluoroethoxymethyl, pentafluoroethylthiomethyl, methoxyethoxymethyl, methoxycarbonyl,
  • R 2 independently of one another represent hydrogen, fluorine, chlorine, methoxy, ethoxy, methyl, ethyl, trifluoromethyl , optionally substituted phenyl, is amino, methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1 , 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, he
  • R 6 represents hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, cyclopropyl, cyclobutyl, Cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
  • R 9 , R 10 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, tert-butyl, fluorine, chlorine, cyano, trifluoromethyl, difluoromethyl,
  • Pentafluoroethyl cyanomethyl, cyanoethyl, cyano-n-propyl, optionally substituted phenyl, heteroaryl, cyclopropyl, cyclobutyl, heterocyclyl,
  • Methoxymethyl methoxyethyl, ethoxymethyl, ethoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl and
  • W is oxygen or sulfur, preferably oxygen.
  • Residue definitions apply both to the end products of general formula (I) as also according to the required in each case for the production of starting or
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, halogen, (C 1 -C 8 ) -alkoxy, (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkyl, (C 1 - C 8 ) -haloalkoxy, (C 1 -C 8 ) -alkylthio, (C 1 -C 8 ) -haloalkylthio, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, nitro, amino, hydroxy, (C 1 -C 8 ) -alkylamino, bis [(C 1 C 8 ) -alkyl] amino, hydrothio,
  • Alkylaminocarbonyl (C 3 -C 8 ) -cycloalkylaminocarbonyl, aryl- (C 1 -C 8 ) -alkylaminocarbonyl, heteroarylaminocarbonyl or
  • R 7 and R 8 with the carbon atom to which they are attached form an oxo group or
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, cyano,
  • (C 1 -C 8 ) -haloalkyl cyano- (C 1 -C 8 ) -alkyl, aryl, heteroaryl, (C 3 -C 8 ) -cycloalkyl, (C 8 -C 8 ) -cycloalkenyl, heterocyclyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl,
  • W is oxygen or sulfur and X, Y independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, halogen, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -haloalkyl, Hydroxy (C 1 -C 8 ) alkyl, cyano (C 1 -C 8 ) alkyl, aryl, heteroaryl, (C 3 -C 8 ) cycloalkyl, (C 2 -C 8 ) cycloalkenyl, heterocyclyl, cyano , Nitro, hydroxy, (C 1 -C 8 ) alkoxy, (C 1 -C 8 ) alkylthio, (C 1 -C 8 ) alkoxy (C 1 -C 8 ) alkyl, (C 1 -C 8 ) -alkenyl- (C 1 -C 8 ) -
  • X and Y with the atom to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 7-membered monocyclic or bicyclic ring.
  • Preferred subject of the invention are compounds of the general formula (I) wherein
  • R 1 represents halogen, cyano, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) halocycloalkyl, (C 4 -C 10) - cycloalkenyl, (C 4 -C 10) -Halocycloalkenyl, (C 3 -C 10 ) -haloalkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylcarbonyl- (C 1 -C 7 ) -alkyl, hydroxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2
  • Heterocyclyl (C 1 -C 7) alkylaminocarbonyl, (C 1 -C 7) alkylsulphonyl, (C 3 -C 7) - cycloalkylsulfonyl, arylsulfonyl, aryl (C 1 -C 7) alkylsulfonyl, heteroarylsulfonyl, heterocyclylsulfonyl, Cyano (C 1 -C 7 ) alkyl, (C 4 -C 7 ) cycloalkenyl (C 1 -C 7 ) alkyl, nitro (C 1 -C 7 ) alkyl, (C 1 -C 7 ) Haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, bis - [(C 1 -C 7 ) -al
  • R 5 is amino, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl,
  • R 6 is hydrogen, (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl, cyano- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylsulfonyl, arylsulfonyl, aryl- (C 1 -C 7 ) -alkylsulfonyl, heteroarylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl,
  • R 7 , R 8 are independently hydrogen, hydroxy, amino, (C 1 -C 7 ) -alkylamino, bis [(C 1 -C 7 ) -alkyl] amino, (C 3 -C 7 ) -cycloalkylamino, (C 1 -C 7 ) -alkyl, fluorine, chlorine,
  • Alkylaminocarbonyl (C 3 -C 7 ) -cycloalkylaminocarbonyl, aryl- (C 1 -C 7 ) -alkylaminocarbonyl, heteroarylaminocarbonyl or
  • R 7 and R 8 with the carbon atom to which they are attached form an oxo group or R 7 and R 8 with the carbon atom to which they are attached, a by
  • R 9 , R 10 independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, cyano, (C 1 -C 7 ) -haloalkyl, cyano- (C 1 -C 7 ) -alkyl, aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C -C 7 ) -cycloalkenyl, heterocyclyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio - (C 1 -C 7 ) -alkyl,
  • W is oxygen or sulfur
  • X, Y independently of one another represent hydrogen, (C 1 -C 7 ) -alkyl, halogen, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -haloalkyl, Hydroxy (C 1 -C 7 ) -alkyl, cyano- (C 1 -C 7 ) -alkyl, aryl, heteroaryl, (C 3 -C 7 ) -cycloalkyl, (C -C 7 ) -cycloalkenyl,
  • X and Y with the atom to which they are attached, a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 7-membered monocyclic or bicyclic ring,
  • a particularly preferred subject of the invention are compounds of the general formula (I) which are described by the formulas (Iaa) to (Ibi),
  • R 1 represents halogen, cyano, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) halocycloalkyl, (C 4 -C 10) - cycloalkenyl, (C 4 -C 10) -Halocycloalkenyl, (C 3 -C 10 ) -haloalkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, hydroxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, ( C 2
  • R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, (C 1 -C 6 ) -alkoxy, (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy, (C 1 -C 6 ) -alkylthio, (C 1 -C 6 ) -haloalkylthio, optionally substituted phenyl, heteroaryl,
  • R 6 is hydrogen, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, cyano- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl, aryl- (C 1 -C 6 ) -alkylsulfonyl, heteroarylsulfonyl, (C 3 -C 6 ) -cycloalkylsulfonyl,
  • R 1 is fluorine, chlorine, bromine, iodine, preferably fluorine and chlorine, cyano, cyclopropyl,
  • Dichlorofluoromethyl bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, 2,2-dichloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, difluoro-tert-butyl, 2-bromo-1, 1, 2-trifluoroethyl, 1, 1, 2,2-tetrafluoroethyl, 1, 2,2,2-tetrafluoroethyl, 2-chloro-1, 1, 2-trifluoroethyl, 2-chloro-1, 1, 2,2-tetrafluoroethyl, 2,2,3,3,3pentafluoropropyl,
  • Cyclobutylmethoxydifluoromethyl but-3-yn-1-ylxydifluoromethyl, pent-4-yn-1-yloxydifluoromethyl, hex-3-yn-1-ylxydifluoromethyl, but-3-en-1-yl-oxydifluoromethyl, 2,2,2-trifluoroethoxydifluoromethyl, 3,3,3-trifluoropropoxydifluoromethyl, 4,4,4-trifluorobutoxyd iflormethyl, 3-chloro-1-methoxybut-3-yl, cyanomethyl,
  • Methoxymethoxymethyl methoxymethoxy, ethoxymethoxy, methoxyethoxy, methoxy-n-propyloxy, ethoxy-n-propyloxy, n-propyloxymethoxy, isopropyloxymethoxy, methoxymethoxyethyl, ethoxymethoxymethyl,
  • Methoxyethoxy-n-propyl methoxymethoxy-n-propyl, methoxy-n-propyloxymethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, trifluoromethoxy-isopropyl, difluoromethoxymethyl,
  • Methoxycarbonylmethyl 1-methoxycarbonyleth-1-yl, 1-methoxycarbonyleth-2-yl methoxycarbonyl-n-propyl, 2-methoxycarbonyl-prop-2-yl, 1-methocycarbonyl-prop-2-yl, 2-methocycarbonyl-prop-1 -yl, methoxycarbonyl-n-butyl,
  • Heterocyclylaminocarbonyl heteroaryl (C 1 -C 6 ) -alkylaminocarbonyl,
  • R 2 , R 3 , R 4 independently of one another represent hydrogen, fluorine, chlorine, bromine, iodine, preferably fluorine and chlorine, methoxy, ethoxy, n-propyloxy, isopropoxy, methyl, ethyl, isopropyl, trifluoromethyl, difluoromethyl, Pentafluoroethyl, trifluoromethoxy, difluoromethoxy, 2,2-difluoroethoxy, 3,3,3-trifluoroethoxy, methylthio, ethylthio, trifluoromethylthio, optionally substituted phenyl, heteroaryl,
  • R 5 is amino, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl , 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1 , 2-Dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2 , 2-trimethylpropyl, 1-e
  • Pentafluoroethyl 1,1,2,2-difluoroethyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, Cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-iso-propyl, heteroaryl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, (C 4 -C 8 ) cycloalkenyl, heterocyclyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl and
  • W is oxygen or sulfur, preferably oxygen.
  • R 1 is cyano, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, adamantan-1-yl, adamantan-2-yl, difluoromethyl, trifluoromethyl, fluoromethyl, 2-fluoroethyl, 2-fluoroprop-2-yl, 1, 1-difluoroethyl, 2 , 2,2-trifluoroethyl, 3,3,3-trifluoropropyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, nonafluorobutyl, cyanomethyl, cyanoeth-1-yl , Cyanoeth-2-yl, cyano-n-propyl, cyano-n-butyl, cyano-iso-propyl, 1-methylcycloprop
  • Pentafluoroethoxymethyl pentafluoroethylthiomethyl, methoxyethoxymethyl, methoxycarbonyl, ethoxycarbonyl, methoxycarbonylmethyl,
  • R 4 independently of one another represent hydrogen, fluorine, chlorine, methoxy, ethoxy, methyl, ethyl, trifluoromethyl, optionally substituted phenyl, amino, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1 - Methylpropyl, 2-methylpropyl, 1, 1-dimethylethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1, 1-dimethylbutyl, 1, 2-dimethylbutyl, 1, 3-dimethylbutyl, 2,2-dimethylbutyl, 2,3- Dimethylbutyl, 3,3
  • R 9 , R 10 independently of one another represent hydrogen, methyl, ethyl, isopropyl, n-propyl, fluorine, chlorine, cyano, trifluoromethyl, difluoromethyl, pentafluoroethyl, 3,3,3-
  • Methylthiomethyl, ethylthiomethyl, methylthioethyl, ethylthioethyl and W is oxygen or sulfur, preferably oxygen.
  • arylsulfonyl is optionally substituted phenylsulfonyl or optionally substituted polycyclic arylsulfonyl, here in particular optionally substituted naphthyl-sulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino,
  • Alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups
  • cycloalkylsulfonyl alone or as part of a chemical group - is optionally substituted Cycloalkylsulfonyl, preferably having 3 to 6 carbon atoms such as cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl or cyclohexylsulfonyl.
  • alkylsulfonyl by itself or as part of a chemical group, represents straight-chain or branched alkylsulfonyl, preferably of 1 to 8, or of 1 to 6 carbon atoms, e.g.
  • alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethyl-propylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methyl
  • heteroarylsulfonyl is optionally substituted
  • substituted polycyclic heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino,
  • alkylthio alone or as part of a chemical group - represents straight-chain or branched S-alkyl, preferably having 1 to 8, or having 1 to 6 carbon atoms, such as (C 1 -C 10 ) -, (C 1 - C 6 ) or (C 1 -C 4 ) alkylthio, for example (but not limited to) (C 1 -C 6 ) alkylthio, such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2 Methylpropylthio, 1, 1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio,
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio means an alkynyl radical bonded via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom
  • Alkoxy means an alkyl radical bonded via an oxygen atom, for example (but not limited to) (C 1 -C 6 ) alkoxy, such as methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy , 1, 1-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, 1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3 -Dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy, 1, 2,2-trimethylpropoxy, 1-ethyl
  • Oxygen-bonded alkenyl radical, alkynyloxy means one over one
  • Oxygen-bonded alkynyl radical such as (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenoxy or (C 3 -C 10 ) -, (C 3 -C 6 ) - or (C 3 -C) alkynoxy.
  • Cycloalkyloxy means a cycloalkyl radical bonded through an oxygen atom
  • cycloalkenyloxy represents a cycloalkenyl radical attached via an oxygen atom.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
  • the number of C atoms refers to the alkyl radical in the alkoxycarbonyl group.
  • alkenyloxycarbonyl and “alkynyloxycarbonyl”, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -O-C (OO) -, such as (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkenyloxycarbonyl or (C 3 -C 10 ) -, (C 3 -C 6 ) - or (C 3 -C 4 ) - alkynyloxycarbonyl.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkene or
  • alkynyloxycarbonyl Alkynyloxycarbonyl.
  • the number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
  • alkenylcarbonyloxy and “alkynylcarbonyloxy” are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (OO) -O-), such as (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) alkenylcarbonyloxy or (C 2 -C 10 ) -, (C 2 -C 6 ) - or (C 2 -C 4 ) -alkynylcarbonyloxy.
  • the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
  • aryl means an optionally substituted mono-, bi- or
  • polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system
  • Rule also includes the term "optionally substituted phenyl”.
  • Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl,
  • heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
  • heterocyclic ring preferably contains 3 to 9 ring atoms, especially 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, as
  • heteroatom from the group N, O and S 1 - or 2- or 3-pyrrolidinyl, 3,4-dihydro-2H-pyrrole-2 or 3-yl, 2, 3-dihydro-1 H-pyrrole 1 - or 2 - or
  • 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 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-membered and 4-membered heterocycles are, for example, 1- or 2-aziridinyl, oxiranyl, thiiranyl, 1- or 2- or 3-azetidinyl, 2- or 3-oxetanyl, 2- or 3-thietanyl, 1,3 -Dioxetan-2-yl. Further examples of
  • Heterocyclyl are a partially or fully hydrogenated heterocyclic radical having two heteroatoms from the group N, O and S, such as 1- or 2- or 3- or 4-pyrazolidinyl; 4,5-dihydro-3H-pyrazole-3 or 4 or 5-yl; 4,5-dihydro-1H-pyrazole-1 - or 3- or 4- or 5-yl; 2,3-dihydro-1H-pyrazole-1 - or 2- or 3- or 4- or 5-yl; 1- or 2- or 3- or 4-imidazolidinyl; 2,3-dihydro-1H-imidazole-1 - or 2- or 3- 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; Hexahydropyridazine-1 - or 2- or 3- or 4-yl; 1,2,3,4-tetrahydropyridazine-1
  • heterocyclyl are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, 1, 4,2-dioxazolidin-2 or 3 or 5-yl; 1, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-1,2,2,2-dioxazine-3- or 5- or 6-yl; 1,2,2-dioxazine-3- or 5- or 6-yl; 1, 4,2-Dioxazepan-2 or 3 or 5 or
  • Heterocycles listed above are at one or more positions, preferably one position, for example in the case of several substituents by the same or various radicals selected from the group consisting of hydrogen, halogen, alkyl,
  • Haloalkyl hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy,
  • Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo.
  • Oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring.
  • lactones and lactams are preferably also included.
  • the oxo group can also occur on the hetero ring atoms, which can exist in different oxidation states, for example at N and S, and then form, for example, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • N (O), S (O) (also SO for short) and S (O) 2 (also short SO2) in the heterocyclic ring.
  • -N (O) and -S (O) groups both enantiomers are included.
  • heteroaryl stands for heteroaromatic compounds, ie completely unsaturated aromatic heterocyclic compounds
  • Heteroaryls of the invention are, for example, 1H-pyrrol-1-yl; 1H-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazole-1-yl; 1 H-imidazol-2-yl; 1 H -imidazol-4-yl; 1 H -imidazol-5-yl; 1H-pyrazole-1-yl; 1H-pyrazol-3-yl; 1H-pyrazol-4-yl; 1 H-pyrazol-5-yl, 1 H-1, 2,3-triazol-1-yl, 1 H-1, 2,3-triazol-4-yl, 1 H-1, 2,3-triazole 5-yl, 2H-1, 2,3-triazol-2-yl, 2H-1,2,3-triazol-4-yl, 1H-1, 2,4-triazol-1-yl
  • heteroaryl groups according to the invention may furthermore be substituted by one or more identical or different radicals. If two adjacent carbon atoms are part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatics.
  • quinolines for example 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-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl
  • quinoxaline for example quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
  • quinoxaline e.g., isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-
  • quinazoline cinnoline; 1,5-naphthyridine; 1,6-naphthyridine; 1,7-naphthyridine; 1,8-naphthyridine; 2,6-naphthyridine; 2,7-naphthyridine; phthalazine; Pyridopyrazine;
  • pyridopyrimidines Pyridopyridazine; pteridines; Pyrimidopyrimidine.
  • Heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1 H-indol-1-yl, 1 H-indol-2-yl, 1 H-indol-3-yl, 1 H-indol-4-yl, 1 H-indol-5-yl, 1H-indol-6-yl, 1H-indol-7-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl , 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1 - Benzothiophen-4-yl, 1-benzothiophene-5-yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-
  • Benzisoxazol-7-yl 1,2-benzisothiazol-3-yl, 1,2-benzisothiazol-4-yl, 1,2-benzisothiazol-5-yl, 1,2-benzisothiazol-6-yl, 1, 2 benzisothiazol-7-yl.
  • 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 monosubstituted or polysubstituted
  • Preferred substituents are halogen atoms, alkoxy, haloalkoxy, cyano, alkylthio, haloalkylthio, amino or nitro groups, particularly preferred
  • bis also includes the combination of different alkyl radicals, for example, methyl (ethyl) or ethyl (methyl).
  • Haloalkyl means the same or different
  • Polyhaloalkyl such as CH 2 CHFCI, CF 2 CCIFH, CF 2 CBrFH, CH 2 CF 3 ;
  • perhaloalkyl also encompasses the term perfluoroalkyl.
  • Partially fluorinated alkyl means a straight-chain or branched, saturated
  • Hydrocarbon which is mono- or polysubstituted by fluorine, wherein the corresponding fluorine atoms as substituents on one or more
  • Hydrocarbon chain can be located, such as. 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 various halogen atoms having at least one fluorine atom, all other optionally present
  • Halogen atoms are selected from the group fluorine, chlorine or bromine, iodine.
  • the corresponding halogen atoms may be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain.
  • Partially fluorinated haloalkyl also includes the
  • Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; The same applies to haloalkenyl and other halogen-substituted radicals.
  • (C 1 -C 4 ) -alkyl given here by way of example means a
  • Carbon atoms corresponding to the range given for C atoms include general alkyl radicals having a larger specified range of C atoms Atoms, z. B. "(C 1 -C 6 ) alkyl”, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are lower
  • Alkyl radicals including in the assembled 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, wherein at least one double bond or triple bond is contained.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more cumulative double bonds, such as For example, allenyl (1,2-propadienyl), 1,2-butadienyl and 1,2,3-pentatrienyl.
  • alkenyl means, for example, vinyl, which may optionally be substituted by further alkyl radicals, for example (but not
  • (C 2 -C 6 ) alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl 1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1 -butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl , 3-
  • Methyl 3-butenyl 1, 1-dimethyl-2-propenyl, 1, 2-dimethyl-1-propenyl, 1, 2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl
  • alkynyl in particular also includes straight-chain or branched open-chain hydrocarbon radicals having more than one triple bond or else having one or more triple bonds and one or more double bonds, for example 1,3-butatrienyl or 3-penten-1-yn-1 -yl.
  • (C 2 -C 6 ) -alkynyl is, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-yl propynyl, 1-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, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl- 3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-penty
  • Haloalkyl amino, alkylamino, bisalkylamino, alkocycarbonyl, hydroxycarbonyl, arylalkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, cycloalkylaminocarbonyl.
  • substituents having a double bond on
  • Cycloalkyl, z As an alkylidene group such as methylidene, are included.
  • polycyclic aliphatic systems are also included, such as bicyclo [1, 1] -butan-1-yl, bicyclo [1, 1] -butan-2-yl, bicyclo [2.1.0] pentane 1 -yl, bicyclo [1 .1 .1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl,
  • (C 3 -C 7 ) -cycloalkyl means a
  • substituted cycloalkyl are also spirocyclic aliphatic
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, eg 1-cyclobutenyl, 2-cyclobutenyl, 1 - Cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1,3-cyclohexadienyl or 1,4-cyclohexadienyl, wherein also substituents having a double bond on the cycloalkenyl radical, e.g. Legs
  • Alkylidene group such as methylidene, are included. In case of if necessary
  • Cycloalkylidene means a carbocyclic radical which is bonded via a double bond.
  • the compounds of the general formula (I) can exist as stereoisomers.
  • the possible stereoisomers defined by their specific spatial form, such as enantiomers, diastereomers, Z and E isomers, are all encompassed by the formula (I). If, for example, 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 may occur.
  • Stereoisomers can be obtained from the resulting mixtures in the preparation by conventional separation methods. The chromatographic separation can be used both on an analytical scale for
  • stereoisomers can be selectively prepared by using stereoselective reactions using optically active sources and / or adjuvants.
  • the invention thus also relates to all stereoisomers which comprises the general formula (I) but are not specified with their specific stereoform, and mixtures thereof.
  • Oxotetrahydroquinolinylsulfonamides of the general formula (I) can according to
  • Synthetic routes are based on commercially available or easily prepared Oxotetrahydrochinolinylaminen and the corresponding sulfonyl chlorides.
  • Optionally further substituted Oxotetrahydrochinolinylamine (A) can be prepared starting from appropriately substituted anilines (Scheme 1).
  • an optionally further substituted aniline with a corresponding Halogenpropionklarhalogenid be coupled using a suitable base in a suitable polar aprotic solvent and reacted in the following step with a suitable Lewis acid in a Friedel-Crafts alkylation to give correspondingly substituted Oxotetrahydrochinolinen in which in further reaction steps, first the radical CR 1 R 9 R 10 , wherein R 1 , R 9 and R 10 have the meaning mentioned above, with the aid of a suitable base (eg. aprotic
  • Solvent e.g., acetonitrile or ⁇ , ⁇ -dimethylformamide, also abbreviated to DMF
  • a suitable nitrating acid e.g., conc.
  • Nitric acid nitrated and then the nitro group using a suitable
  • Reductant eg., Tin (II) chloride dihydrate, iron in acetic acid or hydrogen over palladium on carbon
  • Reductant eg., Tin (II) chloride dihydrate, iron in acetic acid or hydrogen over palladium on carbon
  • a nitro-substituted oxotetrahydroquinoline can be obtained via a tandem reaction of an optionally further substituted alkyl acrylate with an optionally further substituted o-haloaniline by tributyltin hydride and azo-bis- (isobutyronitrile) (corresponding to the abbreviation AIBN) (see Tetrahedron 2009, 65, Giese et al., Org. React., 1996, 48).
  • This type of cyclization can also be carried out electrocatalytically or photochemically (compare J. Org. Chem., 1991, 56, 3246, J. Am. Chem. Soc., 2009, 131, 5036, Photochem., & Photobiol., 2009, 8 , 751).
  • Another alternative to the preparation of nitro-substituted oxotetrahydroquinolines is the
  • Alkylation can be introduced, can be prepared via alternative synthetic routes. By way of example, but not limitation, some of these approaches are described below.
  • 'dba' stands for dibenzylideneacetone
  • BINAP stands for 2,2'-bis (diphenylphosphino) -1, 1'-binaphthyl
  • t-BuXPhos for 2-di-tert-butylphosphino-3,4,5,6 tetramethyl 2 ', 4', 6'-triisopropyl-1, 1'-biphenyl.
  • a suitable Lewis acid eg., Aluminum trichloride or titanium tetrachloride
  • a suitable reducing agent eg stannous chloride hydrate, iron in acetic acid or hydrogen with palladium on carbon
  • R 1 haloalkyl runs the synthesis of the corresponding N-Haloalkylmethyl- substituted, optionally further substituted Oxotetrahydrochinolinylamine exemplary, but not restrictive (via alkylation using an appropriate Haloalkyltrifluormethansulfonats and a suitable base such as
  • a suitable polar aprotic solvent e.g., N, N-
  • N-haloalkylmethyl-substituted nitro-oxotetrahydroquinoline may be prepared by reduction with a suitable reducing agent (e.g., stannous chloride hydrate, iron in acetic acid, or hydrogen with palladium Carbon) is converted into the desired N-haloalkylmethyl-substituted and optionally further substituted oxotetrahydroquinolinylamine (C).
  • a suitable reducing agent e.g., stannous chloride hydrate, iron in acetic acid, or hydrogen with palladium Carbon
  • Aryl and heteroarylsulfonyl chloride precursors may be prepared, for example, via direct
  • R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 9 and R 10 have in
  • Example numbers correspond to the numbers given in Tables A1 to J5 below.
  • Diastereomeric mixtures are given either the respectively significant signals of both diastereomers or the characteristic signal of the main diastereomer.
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (1.09 g, 69% of theory) was isolated as a colorless solid.
  • 6-Nitro-3,4-dihydroquinoline-2 (1H) -one (2000 mg, 2.60 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide, cooled to a temperature of 0 ° C and treated with sodium hydride (458 mg, 1 1 .45 mmol, purity 60%).
  • 6-Amino-1 - (2,2-difluoroethyl) -3,4-dihydroquinolin-2 (1H) -one (142 mg, 0.63 mmol) was added together with (3-methylphenyl) methanesulfonyl chloride (167 mg, 0.82 mmol ) in a heated round bottom flask under argon in abs. Acetonitrile 105 ml), then with pyridine (0.16 ml, 1 .95 mmol) and stirred for 3 hours at a temperature of 70 ° C. The reaction mixture was then concentrated under reduced pressure, the residue remaining admixed with dil.
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (500 mg, 68% of theory) was isolated as a colorless solid. 6-nitro-3,4-dihydroquinoline-2 (1H) -one (500 mg, 2.60 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide and mixed with finely powdered potassium carbonate (1.08 g, 7.81 mmol). After stirring at room temperature for 5 min, chloromethylcyclopropane (306 mg, 3.38 mmol) and Potassium iodide (6 mg, 0.04 mmol) was added.
  • the resulting reaction mixture was stirred for 2 h at 120 ° C and after cooling to room temperature, treated with water and ethyl acetate. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were over
  • 6-Amino-1-cyclopropylmethyl-3,4-dihydroquinoline-2 (1 H) -one (90 mg, 0.42 mmol) was combined with (4-ethylphenyl) methanesulfonyl chloride (100 mg, 0.46 mmol) in a heated round bottom flask under argon in abs. Dissolved acetonitrile (5 ml), then with pyridine (0.07 ml, 0.83 mmol) and stirred for 9 h at room temperature. The reaction mixture was then concentrated under reduced pressure, the residue remaining admixed with dil. HCl and dichloromethane and the aqueous phase extracted several times with dichloromethane.
  • 6-Amino-1-cyclopropylmethyl-3,4-dihydroquinoline-2 (1 H) -one (90 mg, 0.42 mmol) was co-precipitated with (3-fluoro-4-methylphenyl) methanesulfonyl chloride (102 mg, 0.46 mmol) in a heated round bottom flask under argon in abs.
  • Acetonitrile (5 ml) was dissolved, then treated with pyridine (0.07 ml, 0.83 mmol) and stirred for 6 hours at room temperature.
  • the reaction mixture was then concentrated under reduced pressure, the residue remaining admixed with dil. HCl and dichloromethane and the aqueous phase extracted several times with dichloromethane.
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (1.09 g, 69% of theory) was isolated as a colorless solid.
  • 6-nitro-3,4-dihydroquinolin-2 (1H) -one (2.0 g, 10.41 mmol) was dissolved under argon in abs.
  • Dissolve N, N-dimethylformamide (25 mL) and add finely powdered potassium carbonate (4.31 g, 31.22 mmol). After stirring for 5 min at room temperature, cyclobutylmethylbromide (2.02 g, 13.53 mmol) and
  • step 1 (cyclobutylmethyl) -6-nitro-3,4-dihydroquinolin-2 (1 H) -one 1 .34 g, 5.15 mmol) was added together with tin (II) chloride dihydrate (4.65 g, 20.59 mmol ) in abs. Ethanol (10 ml) and stirred under argon at a temperature of 40-50 ° C for 3 h. After cooling to room temperature, the reaction mixture was poured onto ice water and then adjusted to pH 12 with 6N NaOH. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product (gradient
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (1.09 g, 69% of theory) was isolated as a colorless solid.
  • 6-Nitro-3,4-dihydroquinolin-2 (1H) -one (1.20 g, 6.24 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide and mixed with finely powdered potassium carbonate (2.59 g, 18.73 mmol).
  • 6-Nitro-3,4-dihydroquinoline-2 (1 H) -one (2.35 g, 12.23 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide and mixed with finely powdered potassium carbonate (5.07 g, 36.69 mmol). After stirring for 5 min at room temperature, ethyl 2- (chloromethyl) cyclopropanecarboxylate (2.59 g, 15.89 mmol) and potassium iodide (1.01 g, 6.1 mmol) were added. The resulting reaction mixture was stirred for 4 h at 120 ° C and after cooling to room temperature with water and ethyl acetate.
  • 6-Amino-1 - (methoxyethyl) -3,4-dihydroquinoline-2 (1 H) -one 120 mg, 0.55 mmol was combined with (4-methylphenyl) methanesulfonyl chloride (123 mg, 0.60 mmol) in a heated round bottom flask under argon in abs.
  • 6-nitro-3,4-dihydroquinoline-2 (1H) -one (1.09 g, 69% of theory) was isolated as a colorless solid.
  • 6-Nitro-3,4-dihydroquinoline-2 (1 H) -one (1.30 g, 6.77 mmol) was dissolved under argon in abs.
  • 6-Nitro-3,4-dihydroquinoline-2 (1H) -one (2.00 g, 10.41 mmol) was dissolved under argon in abs. Dissolved ⁇ , ⁇ -dimethylformamide and mixed with finely powdered potassium carbonate (4.31 g, 31.22 mmol). After stirring for 5 min at room temperature, 1-bromomethyladamantane (3.10 g, 13.53 mmol) and potassium iodide (0.86 g, 5.20 mmol) were added. The resulting reaction mixture was stirred for 5 h at 120 ° C and after cooling to room temperature with water and ethyl acetate. The aqueous phase was then extracted several times with ethyl acetate.
  • N-2,2,2-trifluoroethylaniline (1.50 g, 8.56 mmol) was dissolved under argon in abs.
  • Tin (II) chloride dihydrate (2.51 g, 11.2 mmol) in abs. Ethanol and stirred for 6 hours under argon at a temperature of 60 ° C. After cooling to
  • reaction mixture was stirred for 4 hours at 50 ° C and after cooling to room temperature carefully diluted with ice water.
  • the aqueous phase was then extracted several times with ethyl acetate.
  • the combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) was 4,4-dimethyl-6-nitro-3,4-dihydroquinoline-2 (1 H) -one (990 mg, 67% of theory) isolated as a colorless solid.
  • reaction mixture was stirred for 30 min at room temperature, cooled to 0 ° C and then treated dropwise with 2- (trifluoromethoxy) ethyl trifluoromethanesulfonate (3.57 g, 13.62 mmol).
  • the reaction mixture was then stirred for 3 hours at room temperature and then added to ice-water and treated with dichloromethane.
  • the aqueous phase was then extracted several times with dichloromethane.
  • the combined organic phases were over
  • Triethylphopsphonoacetate (80.0 g, 1 .0 equiv) was dissolved in abs.
  • Dissolved tetrahydrofuran 50 ml and added to a cooled to 0 ° C suspension of sodium hydride (14.1 g, 1 .03 equiv, 60% dispersion) in abs tetrahydrofuran (50 ml).
  • the resulting reaction mixture was stirred for 10 minutes at a temperature of 0 ° C and then with a solution of butan-2- ⁇ (25.0 g, 1 .0 equiv) in abs.
  • Tetrahydrofuran 150 ml was added and stirred for 4 h at room temperature.
  • step 1 (cyclopropylmethyl) -4-ethyl-4-methyl-6-nitro-3,4-dihydroquinolin-2 (1H) -one (900 mg, 1 .0 equiv.) was added together with zinc powder (1010 mg, 5.0 eq.) and ammonium chloride (828 mg, 5.0 eq.) in methanol (10 ml) and water (1 .0 ml) at a temperature of 0 ° C and stirred for 1 hour under argon at room temperature. The reaction mixture was then on
  • H3-45 4-cyano-N- [1 '- (cyclopropylmethyl) -2'-oxo-2', 3'-dihydro-1'-spiro [cyclopentyl-1, 4'-quinoline] -6'-yl ] phenylsulfonannid
  • Triethylphopsphonoacetate (272.0 g, 1 .0 equiv) was dissolved in abs. Dissolved tetrahydrofuran and added to a cooled to 0 ° C suspension of sodium hydride (49.0 g, 1 .02 equiv, 60% dispersion) in abs tetrahydrofuran (500 ml). The resulting reaction mixture was stirred for 10 minutes at a temperature of 0 ° C and then with a solution of cyclopentanone (100.0 g, 1 .0 equiv) in abs.
  • Tin (II) chloride dihydrate (4 equiv.) In abs. Ethanol and stirred for 6 hours under argon at a temperature of 60 ° C. After cooling to room temperature, the reaction mixture was poured into ice-water and then adjusted to pH 12 with 6N NaOH. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Triethylphopsphonoacetate (232.0 g, 1 .0 equiv) was dissolved in abs. Tetra hydrofu ran (200 ml) and added to a cooled to 0 ° C suspension of sodium hydride (42.0 g, 1 .02 equiv, 60% dispersion) in abs tetrahydrofuran (200 ml).
  • step 1 (cyclopropylmethyl) - 6'-nitro-1 'H-spiro [cyclohexyl-1,4'-quinoline] -2'(3'H) -one (900 mg, 1 .0 equiv.) together with zinc powder (931 mg, 5.0 eq.) and ammonium chloride (759 mg, 5.0 eq.) in abs. Methanol at a temperature of 0 ° C and stirred for 1 h under argon at room temperature. The reaction mixture was then poured onto ice-water and then adjusted to pH 12 with 6N NaOH. The aqueous phase was then extracted several times with ethyl acetate. The combined organic phases were over
  • J3-50 4-methyl-N- [1 '- (cyclopropylmethyl) -2'-oxo-2', 3'-dihydro-1 'H-spiro [cyclobutyl-1, 4'-quinoline] -6' yl] phenylsulfonannid
  • Tnethylphopsphonoacetate (3.32 g, 1 .0 equiv) was dissolved in abs. Dissolved tetrahydrofuran and added to a cooled to 0 ° C suspension of Nat umhydrid (0.58 g, 1 .02 equiv, 60% dispersion) in abs tetrahydrofuran (5 ml). The resulting
  • reaction mixture was stirred for 10 minutes at a temperature of 0 ° C and then with a solution of cyclobutanone (1 .0 g, 1 .0 equiv) in abs. Tetrahydrofuran (5 ml) and stirred for 4 h at room temperature. After the careful addition of water, the reaction mixture was concentrated under reduced pressure and added with dichloromethane. The aqueous phase was then extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure.
  • Ethylcyclobutylidenacetat was isolated (1 .5 g, 75% of theory). Ethylcyclobutylidenacetat (1 .0 g, 1 .0 equiv.) was dissolved in methanol and treated with a 1 M solution of KOH in aq. Methanol. The resulting reaction mixture was stirred for 16 h at room temperature, then neutralized with dil. HCl, water added, concentrated under reduced pressure and then with
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions (Nos 1 to 650, corresponding to compounds A1 -1 to A1-650) in the Table 1 below.
  • An arrow in one of the definitions given for R 5 , R 6 in Table 1 represents a bond of the relevant radical to the core structure (Iaa).
  • R 2 , R 3 and R 4 are hydrogen
  • R 9 and R 10 are hydrogen and W
  • R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding compounds A3-1 to A3-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds A4-1 to A4-650).
  • A7 Compounds A7-1 to A7-650 of the general formula (Iaa) in which R 1 is 2,2,2-trifluoroethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds A7-1 to A7-650).
  • R 1 is 2,2,2-trifluoroethyl
  • R 2 , R 3 and R 4 are hydrogen
  • R 9 and R 10 are hydrogen and W
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds A7-1 to A7-650).
  • A1 1 Compounds A1 1 -1 to A1 1-650 of the general formula (Iaa) in which R 1 is 1, 1, 2,2-tetrafluoroethyl, R 2 , R 3 and R 4 are hydrogen, R 9 is fluorine and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Residue definitions (Nos 1 to 650, corresponding to compounds A21 -1 to A21 -650).
  • A22. Compounds A22-1 to A22-650 of the general formula (Iaa) in which R 1 is cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 denote Definitions for the particular individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds A22-1 to A22-650) correspond.
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Residue definitions (nos 1 to 650, corresponding to compounds A37-1 to A37-650).
  • A40 Compounds A40-1 to A40-650 of the general formula (Iaa) in which R 1 is trimethylsilylmethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 denote Definitions for the particular individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds A40-1 to A40-650) correspond.
  • A41 Compounds A41-1 to A41 -650 of the general formula (Iaa) in which R 1 is trifluoromethoxymethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound the residue definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds B1 -1 to B1 - 650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding compounds B3-1 to B3-650).
  • Residue definitions (Nos 1 to 650, corresponding to compounds B21 -1 to B21 -650).
  • B22. Compounds B22-1 to B22-650 of the general formula (lac), wherein R 1 is cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 den Definitions for the particular individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds B22-1 to B22-650) correspond.
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • B28 Compounds B28-1 to B28-650 of the general formula (lac) in which R 1 is cyclopropyl, R 2 is fluorine, R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds B28-1 to B28-650).
  • B29 Compounds B29-1 to B29-650 of the general formula (lac), wherein R 1 is
  • R 2 , R 3 are fluorine and R 4 is hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions mentioned in Table 1 (Nos 1 to 650; corresponding to compounds B29-1 to B29-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Residue definitions (nos 1 to 650, corresponding to compounds B37-1 to B37-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • B50 Compounds B50-1 to B50-650 of the general formula (Iaa) in which R 1 is methoxycarbonyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 denote Definitions for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds B50-1 to B50-650).
  • B51 Compounds B51-1 to B51-650 of the general formula (Iaa) in which R 1 is methoxycarbonylmethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are each
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding compounds C1 -1 to C1 - 650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds C3-1 to C3-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 is cyclopropyl and R 10 is hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions mentioned in Table 1 (Nos 1 to 650; corresponding
  • R 1 is cyclobutyl
  • R 2 , R 3 and R 4 are hydrogen
  • R 9 and R 10 are hydrogen and W
  • R 5 , R 6 are the definitions for the particular individual compound mentioned in Table 1
  • Cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650; C6-1 to C6-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound shown in Table 1 residue definitions (Nos 1 to 650, corresponding to compounds C7-1 to C7-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650; C8-1 to C8-650). C9. Compounds C9-1 to C9-650 of the general formula (lad), wherein R 1 is for
  • Trimethylsilylmethyl R 2, R 3 and R 4 is hydrogen, R 9 and R 10 are hydrogen and W, R 5, R 6 the definitions of the respective individual compound mentioned in Table 1 radical definitions (Nos 1-650, corresponding compounds C9-1 to C9-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds D1 -1 to D1 - 650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds D3-1 to D3-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Residue definitions (Nos 1 to 650, corresponding to compounds D5-1 to D5-650).
  • Cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of in Table 1 the remaining definitions (Nos 1 to 650, corresponding to compounds D6-1 to D6-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds D7-1 to D7-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650; D8-1 to D8-650).
  • Trimethylsilylmethyl R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds D9-1 to D9-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds E3-1 to E3-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 is cyclopropyl and R 10 is hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions mentioned in Table 1 (Nos 1 to 650; corresponding
  • R 1 is cyclobutyl
  • R 2 , R 3 and R 4 are hydrogen
  • R 9 and R 10 are hydrogen and W
  • R 5 , R 6 are the definitions for the particular individual compound mentioned in Table 1 Residue definitions (nos 1 to 650, corresponding to compounds E5-1 to E5-650).
  • Cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650; E6-1 to E6-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds E7-1 to E7-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650; E8-1 to E8-650).
  • Trimethylsilylmethyl R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds E9-1 to E9-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • E1 Compounds E1 1 -1 to E1 1-650 of the general formula (Ia) in which R 1 is trifluoromethylthiomethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 is
  • R 5 , R 6 correspond to the definitions for the respective individual compounds of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds F2-1 to F2-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds F3-1 to F3-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 is cyclopropyl and R 10 is hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound the residue definitions given in Table 1 (Nos 1 to 650;
  • R 1 is cyclobutyl
  • R 2 , R 3 and R 4 are hydrogen
  • R 9 and R 10 are hydrogen and W
  • R 5 , R 6 are the definitions for the particular individual compound mentioned in Table 1
  • Cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650; F6-1 to F6-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds F7-1 to F7-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650; F8-1 to F8-650).
  • R 5 , R 6 correspond to the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650;
  • Cyclobutyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650; G5-1 to G5-650).
  • G6 Compounds G6-1 to G6-650 of the general formula (lay), wherein R 1 is cyclopentyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 den Definitions for each individual compound of Table 1 These definitions of radicals (Nos 1 to 650, corresponding to compounds G6-1 to G6-650) correspond to one another.
  • G7 Compounds G7-1 to G7-650 of the general formula (lay), wherein R 1 is methoxymethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 den Definitions for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds G7-1 to G7-650).
  • lay general formula (lay) wherein R 1 is methoxymethyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 den Definitions for the particular individual compound correspond to the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds G7-1 to G7-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the radical definitions given in Table 1 (Nos 1 to 650, corresponding to compounds H3-1 to H3-650).
  • Cyclobutyl, R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound of the radical definitions given in Table 1 (Nos 1 to 650; H4-1 to H4-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the respective individual compound of the definitions given in Table 1 (Nos 1 to 650, corresponding to compounds H5-1 to H5-650).
  • R 2 , R 3 and R 4 are hydrogen, R 9 and R 10 are hydrogen and W, R 5 , R 6 are the definitions for the particular individual compound shown in Table 1 residue definitions (Nos 1 to 650, corresponding to compounds 12-1 to I2-650).

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EP15715709.0A 2014-04-10 2015-04-07 Verwendung von substituierten oxotetrahydrochinolinylsulfonamiden oder deren salzen zur steigerung der stresstoleranz in pflanzen Withdrawn EP3128841A1 (de)

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JP6505825B2 (ja) * 2014-08-08 2019-04-24 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニア 植物成長調節剤化合物
JP6906501B2 (ja) * 2015-08-27 2021-07-21 ザ リージェンツ オブ ザ ユニバーシティ オブ カリフォルニアＴｈｅ Ｒｅｇｅｎｔｓ Ｏｆ Ｔｈｅ Ｕｎｉｖｅｒｓｉｔｙ Ｏｆ Ｃａｌｉｆｏｒｎｉａ ハロキナバクチン誘導体
US10842151B2 (en) 2015-08-28 2020-11-24 Cas Center For Excellence In Molecular Plant Sciences Small molecule compound for enhancing plant stress resistance
US11076597B2 (en) * 2015-12-28 2021-08-03 Cas Center For Excellence In Molecular Plant Sciences High stress resistant plant growth regulator and preparation method and use thereof
CN106749044B (zh) * 2015-12-28 2020-04-21 中国科学院上海生命科学研究院 增强植物抗逆性的aba类似物
WO2019025153A1 (de) 2017-07-31 2019-02-07 Bayer Cropscience Aktiengesellschaft Verwendung von substituierten n-sulfonyl-n'-aryldiaminoalkanen und n-sulfonyl-n'-heteroaryldiaminoalkanen oder deren salzen zur steigerung der stresstoleranz in pflanzen
WO2022268520A1 (de) 2021-06-21 2022-12-29 Bayer Aktiengesellschaft Verwendung von substituierten pyrrolidinonen oder deren salzen zur steigerung der stresstoleranz in pflanzen.

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