WO2019025153A1 - Use of substituted n-sulfonyl-n'-aryl diaminoalkanes and n-sulfonyl-n'-heteroaryl diaminoalkanes or salts thereof for increasing the stress tolerance in plants - Google Patents

Use of substituted n-sulfonyl-n'-aryl diaminoalkanes and n-sulfonyl-n'-heteroaryl diaminoalkanes or salts thereof for increasing the stress tolerance in plants Download PDF

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WO2019025153A1
WO2019025153A1 PCT/EP2018/068975 EP2018068975W WO2019025153A1 WO 2019025153 A1 WO2019025153 A1 WO 2019025153A1 EP 2018068975 W EP2018068975 W EP 2018068975W WO 2019025153 A1 WO2019025153 A1 WO 2019025153A1
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alkyl
methyl
phenyl
eth
aryl
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PCT/EP2018/068975
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German (de)
French (fr)
Inventor
Hendrik Helmke
Jana FRANKE
Jens Frackenpohl
Susana Manon GONZALEZ-FERNANDEZ-NINO
Dirk Schmutzler
Fabien Poree
Peter Lümmen
Linn SCHNEIDER
Marcus Koppitz
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Bayer Cropscience Aktiengesellschaft
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Publication of WO2019025153A1 publication Critical patent/WO2019025153A1/en

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
    • A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
    • A01N41/04—Sulfonic acids; Derivatives thereof
    • A01N41/06—Sulfonic acid amides
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C307/00—Amides of sulfuric acids, i.e. compounds having singly-bound oxygen atoms of sulfate groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C307/04—Diamides of sulfuric acids
    • C07C307/06—Diamides of sulfuric acids having nitrogen atoms of the sulfamide groups bound to acyclic carbon atoms
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    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/03—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C311/05—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atoms of the sulfonamide groups bound to hydrogen atoms or to acyclic carbon atoms to acyclic carbon atoms of hydrocarbon radicals substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/12—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
    • C07C311/13—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings the carbon skeleton containing six-membered aromatic rings
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    • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
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    • C07C311/15—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings
    • C07C311/16—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/18—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/24—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/23—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/27—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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    • C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
    • C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/31—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms
    • C07C311/35—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atoms of the sulfonamide groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing rings
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    • C07C311/30—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups
    • C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
    • C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
    • C07C311/39—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom
    • C07C311/41—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to hydrogen atoms or to an acyclic carbon atom to an acyclic carbon atom of a hydrocarbon radical substituted by nitrogen atoms, not being part of nitro or nitroso groups
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    • C07C311/48—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups having nitrogen atoms of sulfonamide groups further bound to another hetero atom
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    • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
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    • C07C311/52—Y being a hetero atom
    • C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
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    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
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    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
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  • Plural Heterocyclic Compounds (AREA)

Abstract

The invention relates to the use of substituted N-sulfonyl-N'-aryl diaminoalkanes and N-sulfonyl-N'-heteroaryl diaminoalkanes of general formula (I), or the salts thereof, formula (I), wherein the groups in general formula (I) are defined as cited in the description, for increasing the stress tolerance of plants with respect to abiotic stress and/or for increasing the plant yield.

Description

Verwendung von substituierten N-Sulfonyl-N'-aryldiaminoalkanen und N-Sulfonyl-N'- heteroaryldiaminoalkanen oder deren Salzen zur Steigerung der Stresstoleranz in Pflanzen.  Use of substituted N-sulfonyl-N'-aryldiaminoalkanes and N-sulfonyl-N'-heteroaryldiaminoalkanes or their salts for increasing the stress tolerance in plants.
Beschreibung description
Die Erfindung betrifft die Verwendung von substituierten N-Sulfonyl-N'-aryldiaminoalkanen und N- Sulfonyl-N'- heteroaryldiaminoalkanen oder deren Salzen zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. The invention relates to the use of substituted N-sulfonyl-N'-aryldiaminoalkanen and N-sulfonyl-N'-heteroaryldiaminoalkanen or their salts to increase the stress tolerance in plants to abiotic stress, and to increase plant growth and / or increase the plant yield.
Es ist bekannt, dass bestimmte Arylsulfonamide wie beispielsweise 2-Cyanobenzolsulfonamide Insektizide Eigenschaften besitzen (vgl. z. B. EP0033984 und WO 2005/035486, WO 2006/056433, WO 2007/060220). 2-Cyanobenzol-sulfonamide mit besonderen heterocyclischen Substitutenten werden in EP 2065370 beschrieben. Es ist weiter bekannt, dass bestimmte Aryl- und Heteroaryl-substituierte Sulfonamide als Wirkstoffe gegen abiotischen Pflanzenstress eingesetzt werden können (vgl. WO 2011/113861). Die Wirkung von bestimmten Aryl-, Heteroaryl- und Benzylsulfonamidocarbonsäuren, - carbonsäureestem, -carbonsäureamiden und -carbonitrilen gegen abiotischen Pflanzenstress wird in WO 2012/089721 und WO 2012/089722 beschrieben. It is known that certain arylsulfonamides such as, for example, 2-cyanobenzenesulfonamides have insecticidal properties (cf., for example, EP0033984 and WO 2005/035486, WO 2006/056433, WO 2007/060220). 2-Cyanobenzenesulfonamides with particular heterocyclic substituents are described in EP 2065370. It is further known that certain aryl- and heteroaryl-substituted sulfonamides can be used as active ingredients against abiotic plant stress (see WO 2011/113861). The action of certain aryl, heteroaryl and benzylsulfonamidocarboxylic acids, carboxylic acid esters, carboxamides and carbonitriles against abiotic plant stress is described in WO 2012/089721 and WO 2012/089722.
Die Herstellung von Sulfamidoalkancarbonsäuren und Sulfamidoalkancarbon-säurenitrilen wird in DE 847006 beschrieben. Die Verwendung ausgewählter Arylsulfonamide mit Alkylcarboxyl-Substituenten als Wuchsregulatoren vor allem zur Beschränkung der Wuchslänge von Reis- und Weizenpflanzen mit dem Ziel der Minimierung des wetterbedingten Umknickens wird in DE 2544859 beschrieben, während die fungizide Wirkung bestimmter N-Cyanoalkylsulfonamide in EP 176327 beschrieben wird. Es ist außerdem bekannt, dass substituierte N-Sulfonyl-aminoacetonitrile zur Kontrolle von Parasiten in Warmblütern eingesetzt werden können (vg. WO 2004/000798). Die Verwendung von l-(4- Methylphenyl)-N-(2-oxo-l -propyl-l,2,3,4-tetrahydrochinolin-6-yl)methansulfonamid gegen The preparation of sulfamidoalkanecarboxylic acids and sulfamidoalkanecarbonitriles is described in DE 847006. The use of selected 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 DE 2544859, while the fungicidal action of certain N-Cyanoalkylsulfonamide is described in EP 176327. It is also known that substituted N-sulfonyl-aminoacetonitriles can be used to control parasites in warm-blooded animals (see WO 2004/000798). The use of 1- (4-methylphenyl) -N- (2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl) methanesulfonamide against
Trockenstress in Arabidopsis thaliana und Soja wird in Proc. Natl. Acad. Sei. 2013, 110(29), 12132- 12137 beschrieben. Die Verwendung von l-(4-Methylphenyl)-N-(2-oxo-l-propyl-l,2,3,4- tetrahydrochinolin-6-yl)methansulfonamid zur Steigerung der Stresstoleranz von Pflanzen wird ebenfalls in CN 104170823 beschrieben. Weitere l-Aryl-N-(2-oxo-l-alkyl-l,2,3,4-tetrahydrochinolin-6- yl)methansulfonamide mit unverzweigter oder verzweigter, aber nicht weiter substituierter Alkylgruppe in der N-Tetrahydrochinolinyleinheit werden in WO 2013/148339 beschrieben. In WO 2013/148339 wird ebenfalls die agonistische Wirkung der betreffenden Substanzen an Abscisinsäurerezeptoren beschrieben. In WO2013/148339 werden weiterhin (2-Oxo-l,2,3,4-tetrahydrochinolin-6- yl)methansulfonamide mit unsubstituierten N-Cycloalkylresten beansprucht, während in WO Drought stress in Arabidopsis thaliana and soy is reported in Proc. Natl. Acad. Be. 2013, 110 (29), 12132-12137. The use of 1- (4-methylphenyl) -N- (2-oxo-1-propyl-1,2,3,4-tetrahydroquinolin-6-yl) methanesulfonamide to increase the stress tolerance of plants is also described in CN 104170823. Further 1-aryl-N- (2-oxo-1-alkyl-1,2,3,4-tetrahydroquinoline-6-yl) methanesulphonamides having an unbranched or branched but not further substituted alkyl group in the N-tetrahydroquinolinyl unit are disclosed in WO 2013 / 148339. In WO 2013/148339 also the agonistic effect of the substances in question on abscisic acid receptors described. In WO2013 / 148339 further claimed (2-oxo-l, 2,3,4-tetrahydroquinoline-6-yl) methanesulfonamide with unsubstituted N-cycloalkyl, while in WO
2015/155154 die Wirkung von speziell substituierten (2-Oxo-l,2,3,4-tetrahydrochinolin-6- yl)methansulfonamiden gegen abiotischen Stress sowie die agonistische Wirkung der betreffenden Substanzen an Abscisinsäure-rezeptoren beschrieben wird. In WO2015/049351 wird die Wirkung von Dihydrooxindolylsulfonamiden gegen abiotischen Stress in Pflanzen beschrieben. 2015/155154 the effect of specially substituted (2-oxo-l, 2,3,4-tetrahydroquinoline-6-yl) methanesulfonamiden against abiotic stress and the agonistic action of the substances in question on abscisic acid receptors is described. In WO2015 / 049351 the action of dihydrooxindolylsulfonamides against abiotic stress in plants is described.
Es ist außerdem bekannt, dass substituierte Arylsulfonamide (vgl. z. B. WO 2009/105774, WO 2006/124875, WO 96/36595) und substitituierte Hetarylsulfonamide (vgl. WO 2009/113600, WO 2007/122219) als pharmazeutische Wirkstoffe verwendet werden können. WO 2003/007931 beschreibt ebenfalls die pharmazeutische Verwendung von substituierten Naphthylsulfonamiden, während in Eur. J. Med. Chem. 2010, 45, 1760 Naphthylsulfonyl-substituierte Glutaminsäureamide und ihre It is also known that substituted arylsulfonamides (cf., for example, WO 2009/105774, WO 2006/124875, WO 96/36595) and substituted hetarylsulfonamides (cf., WO 2009/113600, WO 2007/122219) are used as pharmaceutical active ingredients can be. WO 2003/007931 likewise describes the pharmaceutical use of substituted naphthylsulfonamides, while in Eur. J. Med. Chem. 2010, 45, 1760 naphthylsulfonyl-substituted glutamic acid amides and their
Antitumorwirkung beschrieben werden. Effekte bei Krebsstammzellen werden außerdem in WO 2013/130603 beschrieben. Weiterhin ist bekannt, dass Pyrrolidinyl-substituierte Arylsulfonamide als Cathepsin C-Inhibitoren bei der Behandlung von Atemwegserkrankungen (WO 2009/026197) oder als Antiinfektiva bei der Behandlung von Hepatitis C (WO 2007/092588) eingesetzt werden können. Die pharmazeutische Verwendung von N-Arylsulfonylderivaten verschiedener weiterer Aminosäuren, z.B. als Urokinaseinhibitoren (vgl. WO 2000/05214), als Wirkstoffe zur Behandlung von Diabetes (vgl. WO 2003/091211), als Analgetika (vgl. WO 2008/131947) und als γ-Sekretasemodulatoren (vgl. WO 2010/108067) ist ebenfalls beschrieben. Antitumor effect can be described. Effects on cancer stem cells are also described in WO 2013/130603. Furthermore, it is known that pyrrolidinyl-substituted arylsulfonamides can be used as cathepsin C inhibitors in the treatment of respiratory diseases (WO 2009/026197) or as anti-infective agents in the treatment of hepatitis C (WO 2007/092588). The pharmaceutical use of N-arylsulfonyl derivatives of various other amino acids, e.g. as urokinase inhibitors (see WO 2000/05214), as active ingredients for the treatment of diabetes (see WO 2003/091211), as analgesics (compare WO 2008/131947) and as γ-secretase modulators (see WO 2010/108067) also described.
Es ist ebenfalls bekannt, dass bestimmte p-Cyano-substituierte Anilidderivate als pharmazeutische Wirkstoffe verwendet werden können, beispielsweise als antiandrogene Wirkstoffe (vgl. W098/22432, JP2001/261657, JP2001/328938, WO2000/017163, WO2008/011072, WO2007/137874, It is also known that certain p-cyano-substituted anilide derivatives can be used as pharmaceutically active substances, for example as antiandrogenic active substances (compare WO98 / 22432, JP2001 / 261657, JP2001 / 328938, WO2000 / 017163, WO2008 / 011072, WO2007 / 137874 .
WO2010092546). Die Synthese von p-Cyano-substituierten Aniliden und von N-Sulfonyl-N'-WO2010092546). The synthesis of p-cyano-substituted anilides and N-sulfonyl-N'-
(Cyanoaryl)-diaminoalkanen ist in Med Chem. Lett. 2012, 3, 454; J. Med. Chem. 2010, 53, 2779; Chem. Pharm. Bull. 2004, 52, 1330 beschrieben. Die Wirkung von N-Sulfonyl-N'-aryldiaminoalkanen und N-Sulfonyl-N'-heteroaryldiaminoalkanen gegen abiotischen Stress sowie an (Cyanoaryl) diaminoalkanes is described in Med. Chem. Lett. 2012, 3, 454; J. Med. Chem. 2010, 53, 2779; Chem. Pharm. Bull. 2004, 52, 1330. The effect of N-sulfonyl-N'-aryldiaminoalkanen and N-sulfonyl-N'-heteroaryldiaminoalkanen against abiotic stress and
Abscisinsäurerezeptoren in Pflanzen ist dagegen noch nicht beschrieben. Abscisic acid receptors in plants, however, has not been described.
Es ist bekannt, dass Pflanzen auf natürliche Stressbedingungen, wie beispielsweise Kälte-, Hitze-, Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), Verwundung, It is known that plants are affected by natural stress conditions, such as cold, heat, drought stress (stress caused by drought and / or lack of water), wounding,
Pathogenbefall (Viren, Bakterien, Pilze, Insekten) etc. aber auch auf Herbizide mit spezifischen oder unspezifischen Abwehrmechanismen reagieren können [Pflanzenbiochemie, S. 393-462 , Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996.; Biochemistry and Molecular Biology ofPlants, S. 1102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000] . In Pflanzen sind zahlreiche Proteine und die sie codierenden Gene bekannt, die an Abwehrreaktionen gegen abiotischen Stress (z.B. Kälte, Hitze, Trockenheit, Salz, Überflutung) beteiligt sind. Diese gehören teilweise zu Signaltransduktionsketten (z.B. Transkriptionsfaktoren, Kinasen, Phosphatasen) oder bewirken eine physiologische Antwort der Pflanzenzelle (z.B. Ionentransport, Entgiftung reaktiver Sauerstoff-Spezies). Zu den Signalkettengenen der abiotischen Stressreaktion gehören u.a. Pathogen infestation (viruses, bacteria, fungi, insects) etc. but also on herbicides with specific or nonspecific defense mechanisms can react [Plant Biochemistry, pp. 393-462, Spektrum Akademischer Verlag, Heidelberg, Berlin, Oxford, Hans W. Heidt, 1996; Biochemistry and Molecular Biology of Plants, pp. 1102-1203, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. In plants numerous proteins and their coding genes are known, which are involved in defense reactions against abiotic stress (eg cold, heat, drought, salt, flooding). These belong in part to signal transduction chains (eg transcription factors, kinases, phosphatases) or cause a physiological response of the plant cell (eg ion transport, detoxification of reactive oxygen species). Among the signal chain genes of the abiotic stress response include
Transkriptionsfaktoren der Klassen DREB und CBF (Jaglo-Ottosen et al., 1998, Science 280: 104-106). An der Reaktion auf Salzstress sind Phosphatasen vom Typ ATPK und MP2C beteiligt. Ferner wird bei Salzstress häufig die Biosynthese von Osmolyten wie Prolin oder Sucrose aktiviert. Beteiligt sind hier z.B. die Sucrose-Synthase und Prolin-Transporter (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). Die Stressabwehr der Pflanzen gegen Kälte und Trockenheit benutzt z.T. die gleichen molekularen Mechanismen. Bekannt ist die Akkumulation von sogenannten Late 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. Furthermore, in salt stress the biosynthesis of osmolytes such as proline or sucrose is often activated. Involved here are e.g. the sucrose synthase and proline transporters (Hasegawa et al., 2000, Annu Rev Plant Physiol Plant Mol Biol 51: 463-499). The stress defense of the plants against cold and drought uses z.T. the same molecular mechanisms. The accumulation of so-called Late is known
Embryogenesis Abundant Proteins (LEA-Proteine), zu denen als wichtige Klasse die Dehydrine gehören (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). Es handelt sich dabei um Chaperone, die Vesikel, Proteine und Membranstrukturen in gestressten Pflanzen stabilisieren (Bray, 1993, Plant Physiol 103: 1035-1040). Außerdem erfolgt häufig eine Induktion von Aldehyd-Deydrogenasen, welche die bei oxidativem Stress entstehenden reaktiven Sauerstoff-Spezies (ROS) entgiften (Kirch et al., 2005, Plant Mol Biol 57: 315-332). Embryogenesis Abundant Proteins (LEA Proteins), which include the dehydrins as an important class (Ingram and Bartels, 1996, Annu Rev Plant Physiol Plant Mol Biol 47: 277-403, Close, 1997, Physiol Plant 100: 291-296). These are chaperones that stabilize vesicles, proteins and membrane structures in stressed plants (Bray, 1993, Plant Physiol 103: 1035-1040). In addition, aldehyde dehydrogenases are often induced, detoxifying the reactive oxygen species (ROS) produced by oxidative stress (Kirch et al., 2005, Plant Mol Biol 57: 315-332).
Heat Shock Faktoren (HSF) und Heat Shock Proteine (HSP) werden bei Hitzestress aktiviert und spielen hier als Chaperone eine ähnliche Rolle wie die Dehydrine bei Kälte- und Trockenstress (Yu et al., 2005, Mol Cells 19: 328-333). Heat Shock Factors (HSF) and Heat Shock Proteins (HSP) are activated by heat stress and act as chaperones in a similar role to dehydrins in cold and dry stress (Yu et al., 2005, Mol Cells 19: 328-333).
Eine Reihe von pflanzenendogenen Signalstoffen, die in die Stresstoleranz bzw. die Pathogenabwehr involviert sind, sind bereits bekannt. Zu nennen sind hier beispielsweise Salicylsäure, Benzoesäure, Jasmonsäure oder Ethylen [Biochemistry and Molecular Biology of Plants, S. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Einige dieser Substanzen oder deren stabile synthetische Derivate und abgeleitete Strukturen sind auch bei externer Applikation auf pflanzen oder Saatgutbeizung wirksam und aktivieren Abwehrreaktionen, die eine erhöhte Stress- bzw. Pathogentoleranz der Pflanze zur Folge haben [Sembdner, and Parthier, 1993, Ann. Rev. Plant Physiol. Plant Mol. Biol. 44: 569-589]. A number of plant endogenous signaling substances involved in stress tolerance and pathogen defense are already known. These include, for example, salicylic acid, benzoic acid, jasmonic acid or ethylene [Biochemistry and Molecular Biology of Plants, pp. 850-929, American Society of Plant Physiologists, Rockville, Maryland, eds. Buchanan, Gruissem, Jones, 2000]. Some of these substances or their stable synthetic derivatives and derived structures are also effective in external application to plant 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].
Es ist weiter bekannt, dass chemische Substanzen die Toleranz von Pflanzen gegen abiotischen Stress erhöhen können. Derartige Substanzen werden dabei entweder durch Saatgut-Beizung, durch It is also known that chemical substances can increase the tolerance of plants to abiotic stress. Such substances are thereby either by seed dressing, by
Blattspritzung oder durch Bodenbehandung appliziert. So wird eine Erhöhung der abiotischen Blade spraying or applied by soil treatment. So will an increase in the abiotic
Stresstoleranz von Kulturpflanzen durch Behandlung mit Elicitoren der Systemic Acquired Resistance (SAR) oder Abscisinsäure-Derivaten beschrieben (Schading and Wei, WO 2000/28055; Abrams and Gusta, US 5201931 ; Abrams et al, WO 97/23441, Churchill et al., 1998, Plant Growth Regul 25: 35-45). Desweiteren wurden Effekte von Wachstumsregulatoren auf die Stresstoleranz von Kulturpflanzen beschrieben (Morrison and Andrews, 1992, J Plant Growth Regul 11: 113-117, RD-259027). In diesem Zusammenhang ist ebenfalls bekannt, dass ein wachstumsregulierendes Naphthylsulfonamid (4-Brom- N-(pyridin-2-ylmethyl)naphthalin-l -Sulfonamid) die Keimung von Pflanzensamen in der gleichen Weise wie Abscisinsäure beeinflusst (Park et al. Science 2009, 324, 1068-1071). Weiterhin zeigt eine Stress tolerance of crop plants by treatment with systemic acquired resistance (SAR) or abscisic acid derivatives elicitors (Schading and Wei, WO 2000/28055, Abrams and Gusta, US 5201931, Abrams et al, WO 97/23441, Churchill et al. 1998, Plant Growth Regul 25: 35-45). Furthermore, effects of growth regulators on the stress tolerance of crop plants have been described (Morrison and Andrews, 1992, J Plant Growth Regul 11: 113-117, RD-259027). In this context, it is also known that a growth-regulating 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). Furthermore, one shows
Naphthylsulfamidocarbonsäure (N-[(4-Brom-l-naphthyl)sulfonyl]-5-methoxynorvalin) eine Naphthylsulfamidocarboxylic acid (N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline)
Wirkungsweise in biochemischen Rezeptortests, die mit 4-Brom-N-(pyridin-2-ylmethyl)naphthalin-l- sulfonamid vergleichbar ist (Melcher et al. Nature Structural & Molecular Biology 2010, 17, 1102- 1108). Außerdem ist bekannt, dass ein weiteres Naphthylsulfonamid, N-(6-aminohexyl)-5- chlornaphthalin- 1 -Sulfonamid, den Calcium-Spiegel in Pflanzen beeinflusst, die einem Kälteschock ausgesetzt wurden (Cholewa et al. Can. J. Botany 1997, 75, 375-382). Mode of action in biochemical receptor assays comparable to 4-bromo-N- (pyridin-2-ylmethyl) naphthalene-l-sulfonamide (Melcher et al., Nature Structural & Molecular Biology 2010, 17, 1102-1108). In addition, it is known that another naphthylsulfonamide, N- (6-aminohexyl) -5-chloronaphthalene-1-sulfonamide, affects calcium levels in plants exposed to cold shock (Cholewa et al., Can. J. Botany 1997, Vol. 75, 375-382).
Auch bei Anwendung von Fungiziden, insbesondere aus der Gruppe der Strobilurine oder der Succinat Dehydrogenase Inhibitoren werden ähnliche Effekte beobachtet, die häufig auch mit einer Even with the use of fungicides, in particular from the group of strobilurins or succinate dehydrogenase inhibitors similar effects are observed, often with a
Ertragssteigerung einhergehen (Draber et al., DE 3534948, Bartlett et al., 2002, Pest Manag Sei 60: 309). Es ist ebenfalls bekannt, dass das Herbizid Glyphosat in niedriger Dosierung das Wachstum einiger Pflanzenarten stimuliert (Cedergreen, Env. Pollution 2008, 156, 1099). Increase in yield (Draber et al., DE 3534948, Bartlett et al., 2002, Pest Management 60: 309). It is also known that the low dose herbicide glyphosate stimulates the growth of some plant species (Cedergreen, Env. Pollution 2008, 156, 1099).
Bei osmotischem Stress ist eine Schutzwirkung durch Applikation von Osmolyten wie z.B. Glycinbetain oder deren biochemischen Vorstufen, z.B. Cholin-Derivate beobachtet worden (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE 4103253). Auch die Wirkung von Antioxidantien wie z.B Naphthole und Xanthine zur Erhöhung der abiotischen Stresstoleranz in Pflanzen wurde bereits beschrieben (Bergmann et al., DD 277832, Bergmann et al., DD 277835). Die molekularen Ursachen der Anti-Stress-Wirkung dieser Substanzen sind jedoch weitgehend unbekannt. At osmotic stress, a protective effect is provided by the application of osmolytes, e.g. Glycine betaine or its biochemical precursors, e.g. Choline derivatives have been observed (Chen et al., 2000, Plant Cell Environ 23: 609-618, Bergmann et al., DE 4103253). The effect of antioxidants such as naphthols and xanthines for increasing the abiotic stress tolerance in plants has also been described (Bergmann et al., DD 277832, Bergmann et al., DD 277835). However, the molecular causes of the anti-stress effects of these substances are largely unknown.
Es ist weiter bekannt, dass die Toleranz von Pflanzen gegenüber abiotischem Stress durch eine It is further known that the tolerance of plants to abiotic stress by a
Modifikation der Aktivität von endogenen Poly-ADP-ribose Polymerasen (PARP) oder Poly-(ADP- ribose) glycohydrolasen (PARG) erhöht werden kann (de Block et al., The Plant Journal, 2004, 41, 95; Levine et al., FEBS Lett. 1998, 440, 1 ; WO 00/04173; WO 2004/090140). Modification of the activity of endogenous poly-ADP-ribose polymerases (PARP) or poly (ADP-ribose) glycohydrolases (PARG) can be increased (de Block et al., The Plant Journal, 2004, 41, 95; Levine et al. , FEBS Lett. 1998, 440, 1, WO 00/04173, WO 2004/090140).
Somit ist bekannt, dass Pflanzen über mehrere endogene Reaktionsmechanismen verfügen, die eine wirksame Abwehr gegenüber verschiedensten Schadorganismen und/oder natürlichem abiotischem Stress bewirken können. Da sich die ökologischen und ökonomischen Anforderungen an moderne Pflanzenbehandlungsmittel laufend erhöhen, beispielsweise was deren Toxizität, Selektivität, Thus, it is known that plants have several endogenous reaction mechanisms that can effectively prevent various harmful organisms and / or natural abiotic stress. As the ecological and economic requirements of modern plant treatment products are constantly increasing, for example as regards their toxicity, selectivity,
Aufwandmenge, Rückstandsbildung und günstige Herstellbarkeit angeht, besteht die ständige Aufgabe, neue Pflanzenbehandlungsmittel zu entwickeln, die zumindest in Teilbereichen Vorteile gegenüber den bekannten aufweisen. Daher bestand die Aufgabe der vorliegenden Erfindung darin, Verbindungen bereitzustellen, die die Toleranz gegenüber abiotischem Stress in Pflanzen weiter erhöhen, eine Stärkung des Applied rate, residue formation and cheap manufacturability, there is the constant task of developing new plant treatment agents that have advantages over the known at least in some areas. Therefore, the object of the present invention to provide compounds which further increase the tolerance to abiotic stress in plants, a strengthening of the
Pflanzenwachstums bewirken und/oder zur Erhöhung des Pflanzenertrags beitragen. In diesem  Plant growth and / or contribute to increase the plant yield. In this
Zusammenhang wird unter Toleranz gegenüber abiotischem Stress beispielsweise die Toleranz gegenüber Kälte-, Hitze-, Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), Salzen und Überflutung verstanden.  For example, tolerance to abiotic stress is understood to mean tolerance to cold, heat, drought stress (stress caused by drought and / or lack of water), salting and flooding.
Überraschenderweise wurde nun gefunden, dass substituierte N-Sulfonyl-N'-aryldiaminoalkane und N- Sulfonyl-N'-heteroaryldiaminoalkane zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Surprisingly, it has now been found that substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane for increasing the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or to increase the
Pflanzenertrags verwendet werden können.  Plant yield can be used.
Gegenstand der vorliegenden Erfindung ist demnach die Verwendung substituierter N-Sulfonyl-N'- aryldiaminoalkane und N-Sulfonyl-N'-heteroaryldiaminoalkane der allgemeinen Formel (I) oder deren Salze zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags, The present invention accordingly provides for the use of substituted N-sulfonyl-N'-aryldiaminoalkanes and N-sulfonyl-N'-heteroaryldiaminoalkanes of the general formula (I) or salts thereof for increasing the stress tolerance in plants to abiotic stress and for increasing plant growth and / or to increase plant yield,
Figure imgf000006_0001
Figure imgf000006_0001
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 has the same or different meanings as defined below,
X für Cyano, Halogen, (Ci-C8)-Alkyl, OR12, (Ci-Cio)-Haloalkyl, (Ci-C8)-Haloalkoxy, X is cyano, halogen, (C 1 -C 8 ) -alkyl, OR 12 , (C 1 -C 10) -haloalkyl, (C 1 -C 8 ) -haloalkoxy,
Aminocarbonyl, Aminothiocarbonyl steht, für Wasserstoff, Halogen, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-Cg)- Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl- (Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl-(Ci-C8)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-Aminocarbonyl, aminothiocarbonyl, represents hydrogen, halogen, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-C 8) -alkyl, (C 2 -C 8) - Alkenyl, (C 2 -C 8 ) alkynyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, ( C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (Ci-Cg ) - Haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, (Ci-C8) alkylcarbonyl (Ci-C8) - alkyl, C (0) OR 12, C (O) NR 10 R u, C (0) R 12, -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N (O) C-
(Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkinyl, Heteroaryl-(Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)- alkyl](aryl)silyl-(C2-C8)-alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, (C3-C8)- Cycloalkyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)-alkenyl, Heterocyclyl- (C2-C8)-alkenyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkylaminosulfonylamino, (C3-C8)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)-alkyl]silyl steht, (C 1 -C 8 ) -alkyl, R 10 R u N- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkynyl, heteroaryl- (C 1 -C 8 ) -alkynyl, heterocyclyl- (Ci -C 8) -alkynyl, tris - [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, - bis [(Ci-C 8) - alkyl] silyl (aryl) (C C 2 -C 8 ) -alkynyl, bis-aryl [(C 1 -C 8 ) -alkyl] silyl- (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkynyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, (C 3 -C 8 ) -cycloalkyl- ( C 2 -C 8) alkenyl, (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) -Alkylaminosulfonylamino, (C3-C 8 ) -Cycloalkylaminosulfonylamino, diazo, aryldiazo, tris - [(C 1 -C 8 ) -alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) - alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, Cyano-(Ci-C8)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C 8) -alkyl, (C3-C8) cycloalkyl, cyano (Ci-C 8) - alkyl, (C 3 -C 8) -cycloalkyl- ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C8)- alkylsulfonyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cg)- Haloalkyl, Halo-(C2-C8)-alkinyl, Halo-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkylsulfonyl, Heterocyclyl- (Ci-C8)-alkylsulfonyl, (C4-C8)-Cycloalkenyl, (C4-C8)-Cycloalkenyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, Bis-[(Ci-C8)-Alkyl]aminocarbonyl stehen, Heteroarylsulfonyl, (C3-C8) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (Ci-C8) - alkylsulfonyl, (Ci-C 8) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C8) - cycloalkylcarbonyl, heterocyclylcarbonyl, (C -C 8) alkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci- Cg) - haloalkyl, halo (C 2 -C 8) alkynyl, halo (C 2 -C 8) alkenyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, amino, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkylsulfonyl, heterocyclyl- (C 1 -C 8 ) -alkylsulfonyl, (C 4 -C 8) cycloalkenyl, (C 4 -C 8) cycloalkenyl (Ci-C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, (Ci- C 8) alkylaminocarbonyl, (C3-C8) - cycloalkylaminocarbonyl, bis - [(Ci-C 8) -alkyl] aminocarbonyl stand,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, Halogen,R 3, R 4, R 7 and R 8 independently represent hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halogen,
(Ci-C8)-Haloalkyl, Aryl, Heteroaryl, (C3-C8)-Cycloalkyl, Heterocyclyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino-(Ci-C8)-alkyl, C(0)OR12, C(O)NR10Ru, (Ci-C8) haloalkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, heterocyclyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) - Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, bis [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u ,
C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)- alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N (O) C- (C 1 -C 8 ) -alkyl, R 10 R u is N- (C 1 -C 8 ) -alkyl, m is 0, 1 or 2, n is 1, 2 or 3, R 3 and R 4 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 7 and R 8 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome R 2 and R 6 with the nitrogen atoms to which they are attached, as well as the nitrogen atoms
verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  connecting carbon atoms form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R5 für Amino, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-R 5 is amino, (Ci-C 8) -alkyl, (C 3 -C 8) -cycloalkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (Ci-C 8) -
Haloalkyl, (C3-C8)-Halocycloalkyl, (C4-C8)-Cycloalkenyl, Aryl, Heteroaryl, Heterocyclyl, Aryl- (Ci-Cg)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl- (Ci-C8)-alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkoxycarbonyl- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)- alkoxycarbonyl-(Ci-C8)-alkyl, Aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl- (Ci-C8)-alkyl, (C3-C8)-Cycloalkylammocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- alkylaminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylamino, Arylamino, (C3-C8)-Cycloalkylamino, Aryl-(Ci-C8)-alkylamino, Heteroaryl-(Ci-C8)-alkylamino, Heteroarylamino, Heterocyclylamino, Aryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Heteroaryloxy-(Ci-C8)-alkyl, (C2-C8)- Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenylamino, (C2-C8)-Alkinylamino, Bis-[(Ci-Cg)- alkenyl] amino, Aryloxy, Bis- [(Ci-Cs)-Alkyl] amino, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)- alkenyl, Heterocyclyl-(C2-C8)-alkenyl, Aryloxycarbonyl-(Ci-C8)-alkyl, Heteroaryloxycarbonyl- (Ci-C8)-alkyl, Bis[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Cyano-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylsulfonylamino-(Ci-C8)-alkyl, (C3-C8)-Cycloalkylsulfonylamino-(Ci-C8)-alkyl, Haloalkyl, (C3-C 8) halocycloalkyl, (C4-C8) cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl (Ci-Cg) alkyl, heteroaryl (Ci-C 8) alkyl, heterocyclyl- ( Ci-C 8) alkyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (C 3 - C 8) -Cycloalkoxycarbonyl- (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, heteroaryl (Ci-C 8 ) - alkoxycarbonyl (Ci-C8) alkyl, aminocarbonyl (Ci-C8) alkyl, (Ci-C8) alkylaminocarbonyl (Ci-C8) alkyl, (C 3 -C 8) - Cycloalkylammocarbonyl- (Ci-C 8) alkyl, aryl (Ci-C8) - alkylaminocarbonyl (Ci-C8) alkyl, (Ci-C 8) alkylamino, arylamino, (C3-C8) cycloalkylamino , Aryl- (C 1 -C 8 ) -alkylamino, heteroaryl- (C 1 -C 8 ) -alkylamino, heteroarylamino, heterocyclylamino, aryloxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 4) -alkylamino, C 8) alkyl, heteroaryloxy- (Ci-C 8) alkyl, (C 2 -C 8) - alkenyl, (C 2 -C 8) -alkynyl, (C 2 -C 8) -alkenylamino, (C2- C 8 ) alkynylamino, bis - [(Ci-Cg) alkenyl] amino, aryloxy, bis [(Ci -Cs) alkyl] amino, aryl (C2-C8) alkenyl, heteroaryl (C2-C8) - alkenyl, heterocyclyl- (C 2 -C 8) alkenyl, aryloxycarbonyl (Ci-C 8) alkyl, heteroaryloxycarbonyl, (Ci-C 8) alkyl, bis [(Ci-C 8) alkyl] aminocarbonyl (Ci-C8) alkyl, (Ci-C8) alkylthio (Ci-C 8 ) alkyl, cyano (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - alkylsulfonylamino (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkylsulfonylamino- (C 1 -C 8 ) -alkyl,
Arylsulfonylamino-(Ci-C8)-alkyl, Heteroarylsulfonylamino-(Ci-C8)-alkyl, Arylsulfonylamino (C 1 -C 8 ) -alkyl, heteroarylsulfonylamino (C 1 -C 8 ) -alkyl,
Heterocyclylsulfonylamino-(Ci-C8)-alkyl, Bis-[(Ci-C8)-alkyl]aminosulfonyl-(Ci-C8)-alkyl steht, Heterocyclylsulfonylamino (C 1 -C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] aminosulfonyl- (C 1 -C 8 ) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl,R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR12, S02R13, (Ci-C8)-Alkyl-HN02S-, (C3-C8)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl, Heteroaryl-(C i-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)-Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C8)-alkyl steht (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 8 ) - Alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) alkyl, COR 12, S0 2 R 13, (Ci-C8) alkyl-S- HN0 2, (C 3 -C 8) cycloalkyl HN0 2 S-, heterocyclyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl, heteroaryl- (C iC 8) alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, heterocyclyl (Ci-C 8) -alkyl, is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) - haloalkyl, ( C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -Cio ) -Halocycloalkenyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, aryl, aryl (Ci-C 8) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 8 ) alkyl, (Ci-C8) - alkoxycarbonyl, (Ci-C 8) alkyl, (C 2 -C 8) -Alkenyloxycarbonyl- (Ci-C 8) alkyl, aryl (Ci-C8) - alkoxycarbonyl - (C 1 -C 8 ) -alkyl, hydroxycarbonyl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl
für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, NR10RU steht. is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (C1-C10) - haloalkyl, ( C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -Halocycloalkenyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, aryl, aryl (Ci-C8) - alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C4-C10) - Cycloalkenyl- (Ci-C 8 ) -alkyl, NR 10 R U stands.
Die Verbindungen der allgemeinen Formel (I) können durch Anlagerung einer geeigneten The compounds of general formula (I) can be prepared by addition of a suitable
anorganischen oder organischen Säure, wie beispielsweise Mineralsäuren, wie beispielsweise HCl, HBr, H2SÜ4, H3P04 oder HN03, 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 S 4, H 3 PO 4 or HNO 3 , or organic acids, e.g. For example, 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 in deprotonated form, such as sulfonic acids, certain
Sulfonsäureamide oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden. Salzbildung kann auch durch Einwirkung einer Base auf  Sulfonsäureamide or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups. Salt formation can also be due to the action of 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, in particular sodium and
Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondere Alkalimetall-salze oder  Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. 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, in particular sodium and potassium salts, or else 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, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und [NR a R b R c R d ] + wherein R a to R d are each independently an organic radical, in particular Alkyl, aryl, aralkyl or alkylaryl represent. Also suitable are alkylsulfonium and
Alkylsulfoxoniumsalze, wie (Ci-C4)-Trialkylsulfonium- und (Ci-C4)-Trialkylsulfoxoniumsalze. Alkylsulfoxoniumsalze, such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
Im Folgenden werden die erfindungsgemäß verwendeten Verbindungen der In the following, the compounds used in the invention are the
Formel (I) und ihre Salze "Verbindungen der allgemeinen Formel (I)" bezeichnet. Formula (I) and its salts "compounds of general formula (I)".
Bevorzugter Erfindungsgegenstand ist die Verwendung von Verbindungen der allgemeinen Formel (I), worin The preferred subject of the invention is the use of compounds of general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 has the same or different meanings as defined below,
X für Cyano, Halogen, (Ci-Cv)-Alkyl, OR12, (Ci-Cv)-Haloalkyl, (Ci-Cv)-Haloalkoxy, X is cyano, halogen, (C 1 -C 4) -alkyl, OR 12 , (C 1 -C 4) -haloalkyl, (C 1 -C 4) -haloalkoxy,
Aminocarbonyl, Aminothiocarbonyl steht,  Aminocarbonyl, aminothiocarbonyl,
R1 für Wasserstoff, Halogen, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-Cv)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (C1-C7)- Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl- (Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl-(Ci-C7)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C7)-alkyl, R10RuN(O)C- (Ci-C7)-alkyl, R10RuN-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkinyl, Heteroaryl-(Ci-C7)-alkinyl, Heterocyclyl-(C 1 -C7)-alkinyl, Tris- [(C i-C7)-alkyl] silyl-(C2-C7)-alkinyl, Bis- [(C 1-C7)- alkyl](aryl)silyl-(C2-C7)-alkinyl, Bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, (C3-C7)- Cycloalkyl-(C2-C7)-alkinyl, Aryl-(C2-C7)-alkenyl, Heteroaryl-(C2-C7)-alkenyl, Heterocyclyl- (C2-C7)-alkenyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkylaminosulfonylamino, (C3-C7)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C7)-alkyl]silyl, Bis-[(Ci-C7)-alkyl](aryl)silyl, Bis-aryl[(Ci-C7)-alkyl]silyl steht, R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, Cyano-(Ci-C7)- alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylsulfonyl, Arylsulfonyl, R 1 represents hydrogen, halogen, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-Cv) alkyl, (C 2 -C 7) alkenyl, ( C 2 -C 7 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -) Cio) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy - (Ci-C 7 ) -haloalkyl, (Ci-C 7 ) -haloalkoxy- (Ci-C 7 ) -alkyl, aryl, aryl- (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 7 ) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -Cio) cycloalkenyl (C 7) alkyl, heterocyclyl, heterocyclyl (Ci-C 7 ) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C1-C7) - alkylthio (Ci-C7) alkyl, (Ci-C 7) -Haloalkylthio- (C -C 7) alkyl, (Ci-C 7) alkylcarbonyl (Ci-C7) - alkyl, C (0) OR 12, C (O) NR 10 R u, C (0) R 12, -C = NOR 12 , R 12 0 (0) C- (C 1 -C 7 ) -alkyl, R 10 R u N (O) C- (C 1 -C 7 ) -alkyl, R 10 R u N- (Ci-C 7 ) -alkyl, aryl- (Ci-C 7 ) -alkinyl, heteroaryl- (Ci-C 7) alkynyl, heterocyclyl (C 1 -C 7) -alkynyl, tris [(C iC 7) alkyl] silyl (C 2 -C 7) alkynyl, bis [(C1-C7) - alkyl] (aryl) silyl (C 2 -C 7) alkynyl, bis-aryl [(Ci-C 7) alkyl] silyl (C 2 -C 7) -alkynyl, (C3-C7) - cycloalkyl (C 2 -C 7 ) -alkynyl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7 ) -alkenyl, heterocyclyl- (C 2 -C 7 ) -alkenyl, (C 3 - C7) cycloalkyl (C 2 -C 7) alkenyl, (Ci-C7) alkoxy (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) -Alkylaminosulfonylamino, ( C 3 -C 7) -cycloalkylaminosulfonylamino, diazo, aryldiazo, tris - [(C 1 -C 7 ) -alkyl] silyl, bis - [(C 1 -C 7 ) -alkyl] (aryl) silyl, bis-aryl [( C 7 ) -alkyl] silyl, R 2 and R 6 independently of one another represent 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,
Heteroarylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C7)- alkylsulfonyl, (Ci-C7)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C7)-Alkoxycarbonyl, Aryl-(Ci-C7)- alkoxycarbonyl, (Ci-Cv)-Haloalkylcarbonyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Haloalkyl, Halo-(C2-C7)-alkinyl, Halo-(C2-C7)-alkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Amino, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkylsulfonyl, Heterocyclyl-Heteroarylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl, heterocyclylsulfonyl, aryl- (C 1 -C 7 ) - alkylsulfonyl, (Ci-C 7) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C7) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C 7) alkoxycarbonyl, aryl (Ci-C7) - alkoxycarbonyl, (Ci-Cv) Haloalkylcarbonyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 7 ) -haloalkyl, halo (C 2 -C 7 ) -alkynyl, halo (C 2 -) C 7 ) -alkenyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, amino, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) alkyl, heteroaryl- (C 1 -C 7 ) -alkylsulfonyl, heterocyclyl
(Ci-C7)-alkylsulfonyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Cycloalkenyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Bis-[(Ci-C7)-Alkyl]aminocarbonyl stehen, R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, Halogen, (Ci-C7) alkylsulfonyl, (C 4 -C 7) cycloalkenyl, (C 4 -C 7) cycloalkenyl (C 7) alkyl, (C2-C7) - alkenyloxycarbonyl, (C 2 -C 7 ) alkynyloxycarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl, bis - [(C 1 -C 7 ) -alkyl] -aminocarbonyl, R 3 , R 4 , R 7 and R 8 are independently hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, halogen,
(Ci-C7)-Haloalkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, Heterocyclyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (C1-C7)- Haloalkylthio-(Ci-C7)-alkyl, Bis-[(Ci-C7)-Alkyl]amino-(Ci-C7)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C7)-alkyl, R10RuN(O)C-(Ci-C7)-alkyl, R10RuN-(Ci-C7)- alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, (Ci-C7) haloalkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, heterocyclyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) - alkylthio (Ci-C7) alkyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (C1-C7) - Haloalkylthio- (Ci-C7) alkyl, - bis [( C 1 -C 7 ) -alkyl] amino- (C 1 -C 7 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (Ci-C 7) alkyl, R 10 R u N (O) C- (Ci-C 7) alkyl, R 10 R u N- (Ci-C 7) - are alkyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder form partially saturated, optionally further interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, R 2 and R 6 having the nitrogen atoms to which they are attached and the carbon atoms connecting the nitrogen atoms are completely saturated or partially saturated,
gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R5 für Amino, (Ci-Cv)-Alkyl, (C3-C7)-Cycloalkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C1-C7)- Haloalkyl, (C3-C7)-Halocycloalkyl, (C i-C7)-Cycloalkenyl, Aryl, Heteroaryl, Heterocyclyl, Aryl- (Ci-Cv)-alkyl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-Cv)-Alkoxycarbonyl- (Ci-C7)-alkyl, Aryl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkoxycarbonyl- (Ci-Cv)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkoxycarbonyl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)- alkoxycarbonyl-(Ci-C7)-alkyl, Aminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminocarbonyl- (Ci-Cv)-alkyl, (C3-C7)-Cycloalkylaminocarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-Cv)- alkylaminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylamino, Arylamino, (C3-C7)-Cycloalkylamino, Aryl-(Ci-C7)-alkylamino, Heteroaryl-(Ci-C7)-alkylamino, Heteroarylamino, Heterocyclylamino, Aryloxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Heteroaryloxy-(Ci-C7)-alkyl, (C2-C7)- Alkenyl, (C2-C7)-Alkinyl, (C2-C7)-Alkenylamino, (C2-C7)-Alkinylamino, Bis-[(Ci-C7)- alkenyl] amino, Aryloxy, Bis- [(Ci-C7)-Alkyl] amino, Aryl-(C2-C7)-alkenyl, Heteroaryl-(C2-C7)- alkenyl, Heterocyclyl-(C2-C7)-alkenyl, Aryloxycarbonyl-(Ci-C7)-alkyl, Heteroaryloxycarbonyl- (Ci-Cv)-alkyl, Bis[(Ci-C7)-alkyl]aminocarbonyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, Cyano-(C i -C7)-alkyl, (C i-C7)- Alkoxy-(C i -C7)-alkoxy-(C i-C7)-alkyl, (C 1-C7)- Alkylsulfonylamino-(Ci-C7)-alkyl, (C3-C7)-Cycloalkylsulfonylamino-(Ci-C7)-alkyl, R 5 is amino, (Ci-Cv) alkyl, (C 3 -C 7) -cycloalkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, (C1-C7) - haloalkyl, ( C 3 -C 7 ) -halocycloalkyl, (C 1 -C 7 ) -cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl- (C 1 -C 4) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 1 -C 4) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkoxycarbonyl- (C 1 -C 4) -alkyl, (C 3 -C 7) -cycloalkyl- (C 1 -C 7) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, aminocarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylaminocarbonyl- (C 1 -C 4 ) -alkyl, (C 3 -C 7 ) -cycloalkylaminocarbonyl- (C 1 -C 7 ) -alkyl, aryl - (Ci-Cv) - alkylaminocarbonyl (Ci-C7) -alkyl, (Ci-C 7 ) -alkylamino, arylamino, (C3-C7) -cycloalkylamino, aryl- (Ci-C7) -alkylamino, heteroaryl- (Ci -C 7) -alkylamino, heteroarylamino, heterocyclylamino, aryloxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, heteroaryloxy- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 2 -C 7 ) -alkenylamino, (C 2 -C 7 ) -alkynylamino, bis - [(C 1 -C 7 ) -alkenyl] -amino, aryloxy, bis- [(C 1 -C 7 ) -alkyl] -amino, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl (C2-C7) - alkenyl, heterocyclyl (C 2 -C 7) alkenyl, aryloxycarbonyl (Ci-C7) alkyl, heteroaryloxycarbonyl, (Ci-Cv) alkyl, bis [(Ci-C7) alkyl] aminocarbonyl (Ci C 7) alkyl, (Ci-C7) -alkylthio (Ci-C 7) alkyl, cyano (C i -C 7) alkyl, (C iC 7) - alkoxy (C i -C 7 ) alkoxy (C 7 iC) alkyl, (C1-C7) - alkylsulfonylamino (Ci-C7) alkyl, (C3-C 7) -Cycloalkylsulfonylamino- (Ci-C7) alkyl,
Arylsulfonylamino-(Ci-C7)-alkyl, Heteroarylsulfonylamino-(Ci-C7)-alkyl, Arylsulfonylamino (C 1 -C 7 ) -alkyl, heteroarylsulfonylamino (C 1 -C 7 ) -alkyl,
Heterocyclylsulfonylamino-(Ci-C7)-alkyl, Bis-[(Ci-C7)-alkyl]aminosulfonyl-(Ci-C7)-alkyl steht, R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-C7)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl,Heterocyclylsulfonylamino- (C 1 -C 7 ) -alkyl, bis - [(C 1 -C 7 ) -alkyl] aminosulfonyl- (C 1 -C 7 ) -alkyl, R 11 are identical or different and are each, independently of one another, hydrogen, C 7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-C7) haloalkyl, (C 2 -C 7 ) Haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl,
(C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, COR12, S02R13, (Ci-C7)-Alkyl-HN02S-, (C3-C7)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, (C1-C7)-(C 4 -Cio) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) haloalkoxy (Ci-C7) alkyl, (Ci-C 7 ) -Alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, aryl , aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -Cio) cycloalkenyl (C 7) alkyl, COR 12, S0 2 R 13, (Ci-C7) alkyl-S- HN0 2, (C 3 -C 7) -cycloalkyl-HN0 2 S-, heterocyclyl , (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -
Alkoxycarbonyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-Alkoxycarbonyl, Heteroaryl-(C i-C7)-Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen, für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-C8)-Cycloalkenyl, (C4-Cg)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)- alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C8)-Cycloalkenyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C7)-alkyl steht Alkoxycarbonyl, aryl (Ci-C7) alkoxycarbonyl (Ci-C7) alkyl, aryl (Ci-C 7) alkoxycarbonyl, heteroaryl- (C iC 7) alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, heterocyclyl (Ci-C7) alkyl, represents hydrogen, (Ci-C7) alkyl, (C 2 -C 7) -alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (C1-C10) - haloalkyl, (C 2 -C 7) haloalkenyl, (C 2 -C 7) haloalkynyl, (C 3 -Cio) Cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 8) -cycloalkenyl, (C 4 -C 6) -halocycloalkenyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, C 7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) - alkyl, (C 3 -C 7) cycloalkyl - (C 1 -C 7 ) -alkyl, (C 4 -C 8 ) -cycloalkenyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7) -Alkenyloxycarbonyl- (Ci-C7) alkyl, aryl (Ci-C7) - alkoxycarbonyl (Ci-C7) alkyl, hydroxycarbonyl- (Ci-C7) alkyl, heterocyclyl, heterocyclyl - (Ci-C 7 ) -alkyl
für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, (C4-C8)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C8)- Cycloalkenyl-(Ci-C7)-alkyl, NR10RU steht. Besonders bevorzugter Erfindungsgegenstand ist die Verwendung von Verbindungen der allgemeinen Formel (I), worin is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (C1-C10) - haloalkyl, ( C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C4 -Cio) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C 7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -C 8 ) - cycloalkenyl- (C 1 -C 7 ) -alkyl, NR 10 R U. A particularly preferred subject of the invention is the use of compounds of the general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 has the same or different meanings as defined below,
X für Cyano, Halogen, (Ci-C6)-Alkyl, OR12, (Ci-C6)-Haloalkyl, (Ci-C6)-Haloalkoxy, X is cyano, halogen, (C 1 -C 6 ) -alkyl, OR 12 , (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy,
Aminocarbonyl, Aminothiocarbonyl steht,  Aminocarbonyl, aminothiocarbonyl,
R1 für Wasserstoff, Halogen, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Pentafluorthio, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C7)-Cycloalkenyl- (Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl-(Ci-C6)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C6)-alkyl, R10RuN(O)C- (Ci-C6)-alkyl, R10RuN-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Bis-[(Ci-C6)- alkyl](aryl)silyl-(C2-C6)-alkinyl, Bis-aryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, (C3-C6)- Cycloalkyl-(C2-C6)-alkinyl, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)-alkenyl, Heterocyclyl- (C2-C6)-alkenyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkylaminosulfonylamino, (C3-C6)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C6)-alkyl]silyl, Bis-[(Ci-C6)-alkyl](aryl)silyl, Bis-aryl[(Ci-C6)-alkyl]silyl steht, R 1 represents hydrogen, halogen, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 7 ) cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -halocycloalkenyl, pentafluorothio, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (Ci -C 6) - haloalkoxy (Ci-C 6) -haloalkyl, (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, aryl, aryl (Ci-C 6) alkyl, heteroaryl, heteroaryl (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - alkylthio, (Ci-C 6) alkyl, (Ci-C 6 ) -Haloalkylthio- (Ci-C 6) alkyl, (Ci-C6) alkylcarbonyl (Ci-C 6) - alkyl, C (0) OR 12, C (O) NR 10 R u, C (0 ) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 6 ) -alkyl, R 10 R u N (O) C- (C 1 -C 6 ) -alkyl, R 10 R u N- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkynyl, heteroaryl - (Ci-C 6) alkynyl, heterocyclyl (Ci-C 6) -alkynyl, tris - [(Ci-C6) alkyl] (C 2 -C 6) alkynyl, silyl, bis - [(Ci- C 6 ) alkyl] (aryl) silyl (C 2 -C 6 ) alkynyl, bis-aryl [(Ci-C6) alkyl] silyl (C 2 -C 6 ) alkynyl, (C 3 -C 6) - cycloalkyl- (C 2 -C 6) alkynyl, aryl (C 2 -C 6) alkenyl, heteroaryl (C 2 -C 6) alkenyl, heterocyclyl (C 2 -C 6) alkenyl, (C3 -C 6) cycloalkyl (C 2 -C 6) alkenyl, (Ci-C6) alkoxy (Ci-C6) alkoxy (Ci-C 6) - alkyl, (Ci-C6) -Alkylaminosulfonylamino , (C 3 -C 6 ) -cycloalkylaminosulfonylamino, diazo, aryldiazo, tris - [(C 1 -C 6 ) -alkyl] silyl, bis - [(C 1 -C 6 ) -alkyl] (aryl) -silyl, bis-aryl [(Ci -C 6 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, Cyano-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C6) alkyl, (C3-C6) cycloalkyl, cyano (Ci-C6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C6)- alkylsulfonyl, (Ci-C6)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C6)-Alkoxycarbonyl, Aryl-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Ce)- Haloalkyl, Halo-(C2-C6)-alkinyl, Halo-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkylsulfonyl, Heterocyclyl- (Ci-C6)-alkylsulfonyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, Bis-[(Ci-C6)-Alkyl]aminocarbonyl stehen, 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 6) - Alkoxycarbonyl, aryl- (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) -haloalkylcarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 6) -haloalkyl, halo- (C 2 -C 6) -alkynyl, halo- (C 2 -C 6) alkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, amino, (Ci-C6) alkoxy (Ci -C6) alkoxy- (Ci-C6) -alkyl, heteroaryl- (Ci-C6) -alkylsulfonyl, heterocyclyl (Ci-C 6 ) -alkylsulfonyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6) cycloalkenyl (Ci-C 6) alkyl, (C 2 -C 6) - Alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, (C 1 -C 6) -alkylaminocarbonyl, (C 3 -C 6) -cycloalkylaminocarbonyl, bis - [(C 1 -C 6) -alkyl] aminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, Halogen, (Ci-C6)-Haloalkyl, Aryl, Heteroaryl, (C3-C6)-Cycloalkyl, Heterocyclyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, Bis-[(Ci-C6)-Alkyl]amino-(Ci-C6)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C6)-alkyl, R10RuN(O)C-(Ci-C6)-alkyl, R10RuN-(Ci-C6)- alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6) -alkenyl, halogen, (C 1 -C 6 ) -haloalkyl, aryl, heteroaryl, (C 3 -C 6) cycloalkyl, heterocyclyl, (Ci-C6) alkoxy (Ci-C 6) - alkyl, (Ci-C 6) alkylthio (Ci-C 6) alkyl, (Ci-C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, bis - [(C 1 -C 6 ) -alkyl] amino- (C 1 -C 6 ) -alkyl ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 6 ) -alkyl, R 10 R u N (O) C- (Ci-C 6) alkyl, R 10 R u N- (Ci-C 6) - alkyl is, m is 0, 1 or 2, n is 1, 2 or 3, R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome R 2 and R 6 with the nitrogen atoms to which they are attached, as well as the nitrogen atoms
verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten,  carbon atoms a fully saturated or partially saturated,
gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are each bonded, a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2 und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R5 für Amino, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-R 5 is amino, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) -
Haloalkyl, (C3-C6)-Halocycloalkyl, (C i-C6)-Cycloalkenyl, Aryl, Heteroaryl, Heterocyclyl, Aryl- (Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl- (Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkoxycarbonyl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkoxycarbonyl-(Ci-C6)-alkyl, Aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylaminocarbonyl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Arylamino, (C3-C6)-Cycloalkylamino, Aryl-(Ci-C6)-alkylamino, Heteroaryl-(Ci-C6)-alkylamino, Heteroarylamino, Heterocyclylamino, Aryloxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Heteroaryloxy-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenylamino, (C2-C6)-Alkinylamino, Bis-[(Ci-C6)- alkenyl] amino, Aryloxy, Bis- [(Ci-C6)-Alkyl] amino, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)- alkenyl, Heterocyclyl-(C2-C6)-alkenyl, Aryloxycarbonyl-(Ci-C6)-alkyl, Heteroaryloxycarbonyl- (Ci-C6)-alkyl, Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkylsulfonylamino-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylsulfonylamino-(Ci-C6)-alkyl, Haloalkyl, (C 3 -C 6) -halocycloalkyl, (C 1 -C 6) -cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl- (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl, C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyl- (C 1 -C 6) C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl , Aminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 4 ) -alkyl, C 6 ) - alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino, arylamino, (C 3 -C 6 ) -cycloalkylamino, aryl- (C 1 -C 6 ) -alkylamino, heteroaryl- (C 1 -C 6) - alkylamino, heteroarylamino, heterocyclylamino, aryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, heteroaryloxy- (C 1 -C 6 ) -alkyl, (C 2 -) C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C2-C6) -alkenylamino, (C2-C6) alkynylamino, bis - [(Ci-C 6) - alkenyl] amino, aryloxy, bis - [(C 1 -C 6) -alkyl] amino, aryl- (C 2 -C 6) -alkenyl, Het eroaryl- (C 2 -C 6) -alkenyl, heterocyclyl- (C 2 -C 6) -alkenyl, aryloxycarbonyl- (C 1 -C 6 ) -alkyl, heteroaryloxycarbonyl- (C 1 -C 6 ) -alkyl, bis [(C 1 -C 6 ) -alkyl] alkyl] aminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy - (C 1 -C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonylamino- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkylsulfonylamino- (C 1 -C 6 ) -alkyl .
Arylsulfonylamino-(Ci-C6)-alkyl, Heteroarylsulfonylamino-(Ci-C6)-alkyl,  Arylsulfonylamino (C 1 -C 6) -alkyl, heteroarylsulfonylamino (C 1 -C 6) -alkyl,
Heterocyclylsulfonylamino-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]aminosulfonyl-(Ci-C6)-alkyl steht, R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, (C i-C6)- Alkoxy-(C i-C6)-alkyl, (C i-C6)-Haloalkoxy-(C i -C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, COR12, S02R13, (Ci-C6)-Alkyl-HN02S-, (C3-C6)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl, Aryl-(Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl, Heteroaryl-(C i-Ce)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen, Heterocyclylsulfonylamino (C 1 -C 6) -alkyl, bis - [(C 1 -C 6) -alkyl] aminosulfonyl- (C 1 -C 6) -alkyl, R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -alkynyl, (C 1 -C 6 ) - Cyanoalkyl, (C 1 -C 6 ) -haloalkyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl , (C 4 -C 7) cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, (C iC 6) - alkoxy (C iC 6) alkyl, (C iC 6) haloalkoxy (C i -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl , (C 4 -Cio) cycloalkenyl (Ci-C 6) alkyl, COR 12, S0 2 R 13, (Ci-C 6) alkyl-S- HN0 2, (C 3 -C 6) -cycloalkyl -HNO 2 S-, heterocyclyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -alkyne loxycarbonyl, heterocyclyl- (C 1 -C 6) -alkyl,
R12 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (C1-C7)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)- Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C8)-Cycloalkenyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C6)-alkyl steht und R 12 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (C1-C7) - haloalkyl , (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, ( C 4 -C 7 ) -halocycloalkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- C 6) alkyl, heteroaryl, heteroaryl (Ci-C 6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 4 -C 8) cycloalkenyl (Ci- C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, hydroxycarbonyl- (C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl and
R13 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, (C4-C8)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C8)- Cycloalkenyl-(Ci-C6)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (C1-C10) - haloalkyl , (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 4 -C 8 ) -cycloalkenyl, ( C 4 -C 10) -halocycloalkenyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -haloalkyl, aryl, aryl- (C 1 -C 6) -alkyl , heteroaryl, heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C 3 -C 6) -cycloalkyl- (Ci-C 6) alkyl, (C 4 -C 8 ) - cycloalkenyl- (C 1 -C 6 ) -alkyl, NR 10 R U.
Ganz besonders bevorzugter Erfindungsgegenstand ist die Verwendung von Verbindungen der allgemeinen Formel (I), worin A very particularly preferred subject of the invention is the use of compounds of general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, für Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1 -Methyl- prop-l-yl, 2-Methylprop-l-yl, 1,1-Dimethyleth-l -yl, n-Pentyl, Methoxy, Ethoxy, n-Propyloxy, Trifluormethyl, Difluormethyl, Pentafluorethyl, Heptafluor-n-propyl, Heptafluor-iso-propyl, Trifluormethoxy, Difluormethoxy, Aminocarbonyl, Aminothiocarbonyl steht, für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, Hydroxy, Methylamino, Ethylamino, iso-Propylamino, n-Propylamino, Dimethylamino, Diethylamino, Cyclopropylamino, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 has the same or different meanings as defined below, for cyano, fluoro, chloro, bromo, iodo, methyl, ethyl, n -propyl, iso -propyl, n-butyl, 1-methyl-prop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth -l -yl, n -pentyl, methoxy, ethoxy, n -propyloxy, trifluoromethyl, difluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-iso-propyl, trifluoromethoxy, difluoromethoxy, aminocarbonyl, aminothiocarbonyl, for hydrogen, fluorine, chlorine , Bromine, iodine, cyano, nitro, hydroxy, methylamino, ethylamino, iso-propylamino, n-propylamino, dimethylamino, diethylamino, cyclopropylamino,
Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Methoxycarbonylmethylamino, Methoxycarbonylethylamino, Ethoxycarbonylmethylamino, Ethoxycarbonylethylamino, Methoxycarbonylamino, Ethoxycarbonylamino, tert-Butyloxycarbonylamino, Phenylamino, N- Piperidinyl, N-Pyrrolidinyl, N-Morpholinyl, Methylaminocarbonylamino, Cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, N-piperidinyl, N-pyrrolidinyl, N-morpholinyl, methylaminocarbonylamino,
Ethylaminocarbonylamino, n-Propylaminocarbonylamino, iso-propylaminocarbonylamino, Benzylaminocarbonylamino, Phenylaminocarbonylamino, p-Cl-Phenylaminocarbonylamino, m Cl-Phenylaminocarbonylamino, o-Cl-Phenylaminocarbonylamino, Ethylaminocarbonylamino, n-propylaminocarbonylamino, iso -propylaminocarbonylamino, benzylaminocarbonylamino, phenylaminocarbonylamino, p-Cl-phenylaminocarbonylamino, m is Cl-phenylaminocarbonylamino, o-Cl-phenylaminocarbonylamino,
Cyclopropylaminocarbonylamino, Cyclobutylaminocarbonylamino, Cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino,
Cyclopentylaminocarbonylamino, Cyclohexylaminocarbonylamino, Cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino,
Dimethylaminocarbonylamino, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert Butyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, tert-Butyloxycarbonyloxy,  Dimethylaminocarbonylamino, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert-butyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy,
Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n-Propylaminocarbonyloxy, iso- propylaminocarbonyloxy, Benzylaminocarbonyloxy, Phenylaminocarbonyloxy, Methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy,
Cyclopropylammocarbonyloxy, Cyclobutylaminocarbonyloxy, Cyclopentylaminocarbonyloxy, Cyclohexylaminocarbonyloxy, Dimethylaminocarbonyloxy, Phenyloxy, p-Cl-Phenyloxy, o-Cl- Phenyloxy, m-Cl-Phenyloxy, m-Trifluormethylphenyloxy, p-Trifluormethylphenyloxy, Trifluormethyloxy, Difluormethyloxy, 2,2-Difluorethyloxy, 2,2,2-Trifluorethyloxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Phenylthio, p-Cl-Phenylthio, m-Cl-Phenylthio, o-Cl- Phenylthio, Pyridin-2-ylthio, Pyridin-3-ylthio, Benzylthio, Trifluormethylthio, Cyclopropylammocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, phenyloxy, p-Cl-phenyloxy, o-Cl-phenyloxy, m-Cl-phenyloxy, m-trifluoromethylphenyloxy, p-trifluoromethylphenyloxy, trifluoromethyloxy, difluoromethyloxy, 2,2-difluoroethyloxy, 2, 2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, iso-propylthio, phenylthio, p-Cl-phenylthio, m-Cl-phenylthio, o-Cl-phenylthio, pyridin-2-ylthio, pyridin-3-ylthio, Benzylthio, trifluoromethylthio,
Pentafluorethylthio, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Methylsulfinyl, Ethylsulfinyl, n-Propylsulfinyl, iso-Propylsulfinyl, n-Butylsulfinyl, tert- Butylsulfinyl, Phenylsulfinyl, Benzylsulfinyl, Pyridin-2-ylsulfinyl, Methylsulfonyl, Pentafluoroethylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfinyl, tert-butylsulfinyl, phenylsulfinyl, benzylsulfinyl, pyridin-2-ylsulfinyl, methylsulfonyl,
Ethylsulfonyl, n-Propylsulfonyl, iso-Propylsulfonyl, n-Butylsulfonyl, tert-Butylsulfonyl, Phenylsulfonyl, Benzylsulfonyl, Pyridin-2-ylsulfonyl, 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-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3 -Dimethylbutyl, 3, 3 -Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 Ethyl- 1 -methylpropyl, 1 -Ethyl-2-methylpropyl, Thiocyanato, Isothiocyanato, Ethenyl, 1- Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1-propenyl, 2-Methyl- 1-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3- Pentenyl, 4-Pentenyl, 1 -Methyl- 1-butenyl, 2-Methyl- 1-butenyl, 3 -Methyl- 1-butenyl, 1-Methyl- 2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3- Methyl-3-butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl- 1-propenyl, 1 ,2-Dimethyl-2- propenyl, 1-Ethyl-l -propenyl, l-Ethyl-2-propenyl, Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1- Methyl-2-butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 -Methyl- 1-butinyl, 1 , 1 -Dimethyl-2- propinyl, 1 -Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 3,3-Difluorcyclobut-l-yl, 3- Fluorcyclobut-l-yl, 1-Fluorcyclobut-l-yl, 2,2-Difluorcycloprop-l-yl, 1-Fluorcycloprop-l-yl, 2- Fluorcycloprop-l-yl, 4-Fluorcyclohexyl, 4,4-Difluorcyclohexyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Methylcycloprop-l-yl, 2-Methylcycloprop-l-yl, 2,2- Dimethylcycloprop-l-yl, 2,3-Dimethylcyclopropyl, 1 -Cyanopropyl, 2-Cyanopropyl, 1- Methylcyclobutyl, 2-Methylcyclobutyl, 3-Methylcyclobutyl, 3,3-Dimethylcyclobutyl, 1- Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 1 -Allylcyclopropyl, 1- Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2- Methylcyclohexyl, 3 -Methylcyclohexyl, 1 -Methoxycyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Ethylsulfonyl, n-propylsulfonyl, iso -propylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, phenylsulfonyl, benzylsulfonyl, pyridin-2-ylsulfonyl, 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 ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, thiocyanato, isothiocyanato, ethenyl, 1 - Propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2- Methyl 2-propenyl, 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, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3 butinyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1, 1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 3, 3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluoro cyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1,1,2,2-Tetrafluorethyl, Heptafluor-n- propyl, Heptafluor-iso-propyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl,
Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, Fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl,
Chlormethyl, Brommethyl, Fluormethyl, 3,3,3-Trifluor-n-propyl, Methoxycarbonyl, Chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl,
Ethoxycarbonyl, iso-Propyloxycarbonyl, n-Propyloxycarbonyl, n-Butyloxycarbonyl, tert- Butyloxycarbonyl, Benzyloxycarbonyl, Allyloxycarbonyl, Methylaminocarbonyl, Ethoxycarbonyl, iso-propyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl,
Ethylaminocarbonyl, n-Propylaminocarbonyl, iso-Propylaminocarbonyl, Benzylaminocarbonyl, Phenylaminocarbonyl, Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Ethylaminocarbonyl, n-propylaminocarbonyl, iso -propylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
Cyclopentylaminocarbonyl, Cyclohexylaminocarbonyl, Dimethylaminocarbonyl, Cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl,
Diethylaminocarbonyl, Allylaminocarbonyl, Pentafluorthio, Methoxydifluormethyl, Diethylaminocarbonyl, allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl,
Ethoxydifluormethyl, n-Propyloxydifluormethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, Ethoxyethyl, Methoxyethyl, n-Propyloxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, 1-Methoxyeth-l-yl, 1- Methoxyprop-l-yl, 1-Ethoxyeth-l-yl, 2-Methoxyprop-2-yl, 2-Ethoxyprop-2-yl, Ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-l yl, 1-methoxyprop-1-yl, 1-ethoxyeth-1-yl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl,
Methylthiomethyl, Methylthioethyl, Methylthio-n-propyl, Ethylthiomethyl, Methylthiomethyl, methylthioethyl, methylthio-n-propyl, ethylthiomethyl,
Trifluormethylthiomethyl, Petntafluorethylthiomethyl, Trifluormethylthioethyl, Trifluoromethylthiomethyl, petlafluoroethylthiomethyl, trifluoromethylthioethyl,
Trifluormethylthio-n-propyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, n- Butylcarbonyl, tert-Butylcarbonyl, Phenylcarbonyl, o-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, p-Cl-Phenylcarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n-Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, tert- Butyloxycarbonylethyl, Hydroxycarbonylmethyl, Hydroxycarbonylethyl, Hydroxycarbonyl, Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, n-Propylaminocarbonylmethyl, iso- Propylaminocarbonylmethyl, Benzylaminocarbonylmethyl, Phenylaminocarbonylmethyl, Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl, Trifluoromethylthio-n-propyl, methylcarbonyl, ethylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, o-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, p-Cl-phenylcarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, tert Butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl, methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, iso- propylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl,
Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl,  Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl,
Dimethylaminocarbonylmethyl, Diethylaminocarbonylmethyl, Allylaminocarbonylmethyl, Methylaminomethyl, Dimethylaminomethyl, Diethylaminomethyl, Ethylaminomethyl, iso- Propylaminomethyl, n-Propylaminomethyl, n-Butylaminomethyl, Methylaminoethyl,  Dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, iso-propylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl,
Dimethylaminoethyl, Diethylaminoethyl, N-Pyrrolidinylmethyl, N-Piperidinylmethyl,  Dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, N-piperidinylmethyl,
Hydroxyimino, Methoxyimino, Ethoxyimino, n-Propyloxyimino, n-Butyloxyimino, iso- Propyloxyimino, tert-Butyloxyimino, Cyclopropylmethoxyimino,  Hydroxyimino, methoxyimino, ethoxyimino, n-propyloxyimino, n-butyloxyimino, iso-propyloxyimino, tert-butyloxyimino, cyclopropylmethoxyimino,
Cyclobutylmethoxyimino,Cyclopentylmethoxyimino, Cyclohexylmethoxyimino,  Cyclobutylmethoxyimino, cyclopentylmethoxyimino, cyclohexylmethoxyimino,
Benzyloxyimino, Phenyloxyimino, Allyloxyimino, p-Cl-Phenylmethyloxyimino, Phenylethinyl, p-Cl-Phenylethinyl, m-Cl-Phenylethinyl, o-Cl-Phenylethinyl, p-F-Phenylethinyl, m-F- Phenylethinyl, o-F-Phenylethinyl, Pyridin-2-ylethinyl, Pyridin-3-ylethinyl, Thiophen-2- ylethinyl, Trimethylsilylethinyl, Triethylsilylethinyl, Tri(iso-propyl)silylethinyl,  Benzyloxyimino, phenyloxyimino, allyloxyimino, p-Cl-phenylmethyloxyimino, phenylethynyl, p-Cl-phenylethynyl, m-Cl-phenylethynyl, o-Cl-phenylethynyl, pF-phenylethynyl, mF-phenylethynyl, oF-phenylethynyl, pyridin-2-ylethynyl, Pyridin-3-ylethynyl, thiophen-2-ylethynyl, trimethylsilylethynyl, triethylsilylethynyl, tri (iso-propyl) silylethynyl,
Cyclopropylethinyl, Cyclobutylethinyl, Cyclopentylethinyl, Cyclohexylethinyl, Phenyl, Benzyl, p-Cl-Phenyl, m-Cl-Phenyl, o-Cl-Phenyl, p-F-Phenyl, m-F-Phenyl, o-F-Phenyl, p- Trifluormethylphenyl, m-Trifluormethylphenyl, o-Trifluormethylphenyl, p-Methylphenyl, m- Methylphenyl, o-Methylphenyl, p-Methoxyphenyl, m-Methoxyphenyl, o-Methoxyphenyl, p-Cl- Phenylmethyl, m-Cl-Phenylmethyl, o-Cl-Phenylmethyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Thiophen-2-yl, Thiophen-3-yl, Furan-2-yl, Furan-3-yl, Pyrimidin-2-yl, Pyrazin-2-yl,  Cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, phenyl, benzyl, p-Cl-phenyl, m-Cl-phenyl, o-Cl-phenyl, pF-phenyl, mF-phenyl, oF-phenyl, p-trifluoromethylphenyl, m-trifluoromethylphenyl, o-trifluoromethylphenyl, p-methylphenyl, m-methylphenyl, o-methylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-Cl-phenylmethyl, m-Cl-phenylmethyl, o-Cl-phenylmethyl, pyridin-2 yl, pyridin-3-yl, pyridin-4-yl, thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrimidin-2-yl, pyrazine-2-yl,
Methoxymethoxymethyl, Ethoxyethoxymethyl, Methoxyethoxymethyl,  Methoxymethoxymethyl, ethoxyethoxymethyl, methoxyethoxymethyl,
Methylaminosulfonylamino, Dimethylaminosulfonylamino, Ethylaminosulfonylamino, Diethylaminosulfonylamino, iso-Propylaminosulfonylamino, Cyclopropylaminosulfonylamino, Cyclobutylaminosulfonylamino, Cyclopentylaminosulfonylamino,  Methylaminosulfonylamino, dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, iso-propylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino, cyclopentylaminosulfonylamino,
Cyclohexylaminosulfonylamino, steht,  Cyclohexylaminosulfonylamino,
R2 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1 - Methyl-prop-l-yl, 2-Methyl-prop-l-yl, n-Pentyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanomethyl, 2-Cyanoeth-l-yl, 1-Cyano-eth-l-yl, 3-Cyanoprop-l-yl, R 2 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methyl-prop-1-yl, 2-methyl-prop-1-yl, n-pentyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanomethyl, 2-cyanoeth-1-yl, 1-cyano-eth-1-yl, 3-cyanoprop-1-yl,
Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Cyclopentylmethyl,  Cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Methylsulfonyl, Ethylsulfonyl, iso-Propylsulfonyl, n-Propylsulfonyl, n- Butylsulfonyl, 1-Methylprop-l-yl, 2-Methylprop-l -yl, 1,1-Dimethyleth-l-ylsulfonyl,  Cyclohexylmethyl, methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsulfonyl,
Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl, Cyclohexylsulfonyl, Phenylsulfonyl, p-Cl-Phenylsulfonyl, m-Cl-Phenylsulfonyl, p-Cl-Phenylsulfonyl, p-F- Phenylsulfonyl, m-F-Phenylsulfonyl, p-F-Phenylsulfonyl, p-Cyano-Phenylsulfonyl, m-Cyano- Phenylsulfonyl, p-Cyano-Phenylsulfonyl, p-Methylphenylsulfonyl, m-Methylphenylsulfonyl, p- Methylphenylsulfonyl, p-Trifluormethylphenylsulfonyl, m-Trifluormethylphenylsulfonyl, p- Trifluormethylphenylsulfonyl, Benzylsulfonyl, p-Cl-Phenylmethylsulfonyl, m-Cl- Phenylmethylsulfonyl, p-Cl-Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, m-F- Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, m-Cyano- Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, m- Methyl-phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, m-Trifluormethyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, tert.-Butylcarbonyl, Phenylcarbonyl, p-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, o-Cl-Phenylcarbonyl, p-F- Phenylcarbonyl, m-F-Phenylcarbonyl, o-F-Phenylcarbonyl, Pyridin-2-ylcarbonyl, Pyridin-3- ylcarbonyl, Pyridin-4-ylcarbonyl, 4-Trifluormethyl-pyridin-3-ylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexylcarbonyl, Methoxycarbonyl, Cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl, Phenylsulfonyl, p-Cl-phenylsulfonyl, m-Cl-phenylsulfonyl, p-Cl-phenylsulfonyl, pF-phenylsulfonyl, mF-phenylsulfonyl, pF-phenylsulfonyl, p-cyano-phenylsulfonyl, m-cyano-phenylsulfonyl, p-cyano-phenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, p-methylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, m-trifluoromethylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, benzylsulfonyl, p-Cl-phenylmethylsulfonyl, m-Cl-phenylmethylsulfonyl, p-Cl-phenylmethylsulfonyl, pF-phenylmethylsulfonyl, mF- Phenylmethylsulfonyl, p-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, m-cyano-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, p-methylphenylmethylsulfonyl, m-methylphenylmethylsulfonyl, p-methylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, m- Trifluoromethylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, methylcarbonyl, ethylcarbonyl, iso -propylcarbonyl, tert -butylcarbonyl, phenylcarbonyl, p-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, o-Cl-phenylc arbonyl, pF-phenylcarbonyl, mF-phenylcarbonyl, oF-phenylcarbonyl, pyridin-2-ylcarbonyl, pyridin-3-ylcarbonyl, pyridin-4-ylcarbonyl, 4-trifluoromethylpyridin-3-ylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoxycarbonyl,
Ethoxycarbonyl, tert-Butyloxycarbonyl, Benzyloxycarbonyl, Trifluormethylcarbonyl,  Ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, trifluoromethylcarbonyl,
Difluormethylcarbonyl, Allyl, Propargyl, 2,2-Difluorethyl, 3,3,3-Trifluorethyl, Methoxymethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxyethyl, Ethoxymethyl, Ethoxy-n-propyl, Amino, Methylaminocarbonyl, Ethylaminocarbonyl, Dimethylaminocarbonyl stehen,  Difluoromethylcarbonyl, allyl, propargyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, methoxymethyl, methoxyethyl, methoxy-n-propyl, ethoxyethyl, ethoxymethyl, ethoxy-n-propyl, amino, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Trifluormethyl, Difluormethyl, Phenyl, p-Cl-Phenyl, m-Cl-Phenyl, o-Cl-Phenyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, trifluoromethyl, difluoromethyl, phenyl, p-Cl-phenyl, m-Cl-phenyl, Cl-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxymethyl, ethoxymethyl, ethoxyethyl,
Methoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methylthioethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethylthiomethyl, Trifluormethylthioethyl,  Methoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl,
Dimethylaminomethyl, Dimethylaminoethyl, Hydroxycarbonyl, methoxycarbonyl,  Dimethylaminomethyl, dimethylaminoethyl, hydroxycarbonyl, methoxycarbonyl,
Ethoxycarbonyl, ior-Propyloxycarbonyl, n-Propyloxycarbonyl, tert-Butyloxycarbonyl, Allyloxycarbonyl, Benzyloxycarbonyl, Dimethylaminocarbonyl, Aminocarbonyl,  Ethoxycarbonyl, ior-propyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, dimethylaminocarbonyl, aminocarbonyl,
Methylaminocarbonyl, Ethylaminocarbonyl, iso-Propylaminocarbonyl,  Methylaminocarbonyl, ethylaminocarbonyl, iso-propylaminocarbonyl,
Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentylaminocarbonyl,  Cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl,
Cyclohexylaminocarbonyl, Hydroxycarbonylmethyl, Methoxycarbonylmethyl,  Cyclohexylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl, ior-Propyloxycarbonylmethyl, n-Propyloxycarbonylmethyl, tert- Butyloxycarbonylmethyl, Allyloxycarbonylmethyl, Benzyloxycarbonylmethyl,  Ethoxycarbonylmethyl, iorpropyloxycarbonylmethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl,
Dimethylaminocarbonylmethyl, Aminocarbonylmethyl, Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, iso-Propylaminocarbonylmethyl,  Dimethylaminocarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, iso-propylaminocarbonylmethyl,
Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl,  Cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl,
Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl stehen, m für 0, 1 oder 2 steht, n für 1, 2 oder 3 steht, Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 4 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or R 7 and R 8 with the carbon atom, to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome R 2 and R 6 with the nitrogen atoms to which they are attached, as well as the nitrogen atoms
verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  connecting carbon atoms form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R und R mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or R and R with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden und R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are each bonded, form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring and
R5 für 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 und 1 -Ethyl-2-methylpropyl. Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluorpropyl, Pentafluorethyl, Heptafluor-n-Propyl, Heptafluor-iso-propyl, Nonafluor-n-butyl, Phenyl, 2-Cyanophenyl, 3-Cyanophenyl, 4-Cyanophenyl, 2-Fluor-Phenyl, 3- Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3- Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor- Phenyl, 2-Chlor-Phenyl, 3-Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor- Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5- Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3-Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4- Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3- Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3- Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3-Methyl-Phenyl, 4-Methyl- Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl- Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl- Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy- Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl- Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor- Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3- Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy- Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, 2-Ethyl- Phenyl, 3-Ethyl-Phenyl, 4-Ethyl-Phenyl, 2-Methoxycarbonyl-Phenyl, 3-Methoxycarbonyl- Phenyl, 4-Methoxycarbonyl-Phenyl, 2-Ethoxycarbonyl-Phenyl, 3-Ethoxycarbonyl-Phenyl, 4- Ethoxycarbonyl-Phenyl, 4-(Methylcarbonylamino)phenyl, 4-(iso-Propylcarbonylamino)phenyl, 4-(cyclo-Propylamino)phenyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyridazin- 3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-5-yl, Pyrimidin-4-yl, Pyridazin-3 -ylmethyl, Pyridazin-4-ylmethyl, Pyrimidin-2 -ylmethyl, Pyrimidin-5-ylmethyl, Pyrimidin-4-ylmethyl, Pyrazin-2-ylmethyl, 3-Chlor-Pyrazin-2-yl, 3-Brom-Pyrazin-2-yl, 3-Methoxy-Pyrazin-2-yl, 3- Ethoxy-Pyrazin-2-yl, 3-Trifluormethylpyrazin-2-yl, 3-Cyanopyrazin-2-yl, Naphth-2-yl, Naphth- 1 -yl, Chinolin-4-yl, Chinolin-6-yl, Chinolin-8-yl, Chinolin-2-yl, Chinoxalin-2-yl, 2- Naphthylmethyl, 1 -Naphthylmethyl, Chinolin-4-ylmethyl, Chinolin-6-ylmethyl, Chinolin-8- ylmethyl, Chinolin-2-ylmethyl, Chinoxalin-2 -ylmethyl, Pyrazin-2-ylmethyl, 4-Chloropyridin-2- yl, 3-Chloropyridin-4-yl, 2-Chloropyridin-3-yl, 2-Chloropyridin-4-yl, 2-Chlorpyridin-5-yl, 2,6- Dichlorpyridin-4-yl, 3-Chlorpyridin-5-yl, 3,5-Dichlorpyridin-2-yl, 3-Chlor-5- Trifluormethylpyridin-2-yl, (4-Chloropyridin-2-yl)methyl, (3-Chloropyridin-4-yl)methyl, (2- Chloropyridin-3-yl)methyl, (2-Chloropyridin-4-yl)methyl, (2-Chlorpyridin-5-yl)methyl, (2,6- Dichlorpyridin-4-yl)methyl, (3-Chlorpyridin-5-yl)methyl, (3,5-Dichlorpyridin-2-yl)methyl, Thiophen-2-yl, Thiophen-3-yl, 5-Methylthiophen-2-yl, 5-Ethylthiophen-2-yl, 5-Chlorthiophen- 2-yl, 5-Bromthiophen-2-yl, 4-Methylthiophen-2-yl, 3-Methylthiophen-2-yl, 5-Fluorthiophen-3- yl, 3,5-Dimethylthiophen-2-yl, 3-Ethylthiophen-2-yl, 4,5-Dimethylthiophen-2-yl, 3,4- Dimethylthiophen-2-yl, 4-Chlorthiophen-2-yl, Furan-2-yl, 5-Methylfuran-2-yl, 5-Ethylfuran-2- yl, 5-Methoxycarbonylfuran-2-yl, 5-Chlorfuran-2-yl, 5-Bromfuran-2-yl, Thiophan-2-yl, Thiophan-3-yl, Sulfolan-2-yl, Sulfolan-3-yl, Tetrahydrothiopyran-4-yl, Tetrahydropyran-4-yl, Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, 2-Phenyleth-l-yl, l-(4-Methylphenyl)eth-l-yl, 1- (3-Methylphenyl)eth-l-yl, l-(2-Methylphenyl)eth-l-yl, l-(4-Chlorphenyl)eth-l-yl, l-(3- Chlorphenyl)eth-l-yl, l-(2-Chlorphenyl)eth-l-yl, l-(4-Trifluormethylphenyl)eth-l-yl, l-(3- Trifluormethylphenyl)eth- 1 -yl, 1 -(2-Trifluormethylphenyl)eth- 1 -yl, 1 -(4-Fluorphenyl)eth- 1 -yl, l-(3-Fluorphenyl)eth-l-yl, l-(2-Fluorphenyl)eth-l-yl, l-(4-Cyanophenyl)eth-l-yl, l-(3- Cyanophenyl)eth-l-yl, l-(2-Cyanophenyl)eth-l-yl, 2-(3-Fluorphenyl)eth-l-yl, 2-(4- Fluorphenyl)eth-l-yl, 2-(2-Fluorphenyl)eth-l -yl, 2-(2-Chlorphenyl)eth-l-yl, 2-(3- Chlorphenyl)eth-l-yl, 2-(4-Chlorphenyl)eth-l-yl, 2-(2-Bromphenyl)eth-l-yl, 2-(3- Bromphenyl)eth-l-yl, 2-(4-Bromphenyl)eth-l-yl, 2-(2-Cyanophenyl)eth-l-yl, 2-(3- Cyanophenyl)eth-l-yl, 2-(4-Cyanophenyl)eth-l-yl, 2-(2-Trifluormethylphenyl)eth-l-yl, 2-(3- Trifluormethylphenyl)eth- 1 -yl, 2-(4-Trifluormethylphenyl)eth- 1 -yl, 2-(2-Methoxyphenyl)eth- 1 - yl, 2-(3 -Methoxyphenyl)eth- 1 -yl, 2-(4-Methoxyphenyl)eth- 1 -yl, 2-(4-Methylphenyl)eth- 1 -yl, 2-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-ethyl-2-methylpropyl. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, pentafluoroethyl, heptafluoro-n-propyl, Heptafluoro-isopropyl, nonafluoro-n-butyl, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro- Phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,3-difluoro-phenyl, 3,4-difluoro-phenyl, 3,5-difluoro-phenyl, 2,4,5-trifluoro-phenyl Phenyl, 3,4,5-trifluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,4-dichloro-phenyl, 2,5-dichloro-phenyl, 2,6- Dichloro-phenyl, 2,3-dichloro-phenyl, 3,4-dichloro-phenyl, 3,5-dichloro-phenyl, 2,4,5-trichloro-phenyl, 3,4,5-trichloro-phenyl, 2, 4,6-trichloro-phenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3-iodo-phenyl, 4-iodo-phenyl, 2-bromo-4 Fluorine-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chloro-phenyl, 3-bromo-5-fluoro Phenyl, 3-bromo-5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo Phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro Phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3-methyl-phenyl, 4-methyl-phenyl , 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2 , 4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4-methoxy-phenyl, 2,4 -Dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dimethoxy-phenyl, 2,4,5 Trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4- Trifluoromethoxy-phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl- Phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluoro-phenyl, 3-trifluoromethyl-5-chloro-phenyl, 3-methyl-5-fluoro-phenyl, 3 -Methyl-5-chloro-phenyl, 3-methoxy-5-fluoro-phenyl, 3-methoxy-5-chloro-phenyl, 3-trifluoromethoxy-5-chloro-phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl , 4-ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, 2-ethyl-phenyl, 3 Ethyl-phenyl, 4-ethyl-phenyl, 2-methoxycarbonyl-phenyl, 3-methoxycarbonyl-phenyl, 4-methoxycarbonyl-phenyl, 2-ethoxycarbonyl-phenyl, 3-ethoxycarbonyl-phenyl, 4-ethoxycarbonyl-phenyl, 4- (2-methoxycarbonyl-phenyl) Methylcarbonylamino) phenyl, 4- (iso -propylcarbonylamino) phenyl, 4- (cyclopropylamino) phenyl, pyridin-2-yl, Pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazine 3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazine-2-ylmethyl, 3-chloro-pyrazine-2-yl, 3-bromo-pyrazine 2-yl, 3-methoxy-pyrazine-2-yl, 3-ethoxy-pyrazine-2-yl, 3-trifluoromethyl-pyrazine-2-yl, 3-cyanopyrazine-2-yl, naphth-2-yl, naphth-1 - yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinoline-6 ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxaline-2-ylmethyl, pyrazin-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5 Trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl) methyl, (3-chloropyridin-4-yl) methyl, (2-chloropyridin-3-yl) methyl, (2-chloropyridine-4 -yl) methyl, (2-chloropyridin-5-yl) methyl, (2,6-dichloropyridin-4-yl) methyl, (3-chloropyridin-5-yl) methyl, (3,5-dichloropyridin-2-yl ) methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophen-2-yl, 5-ethylthiophene-2-yl, 5-chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophene -2-yl, 3-methylthiophene-2-yl, 5-fluorothiophene-3-yl, 3,5-dimethylthiophene-2-yl, 3-ethylthiophene-2-yl, 4,5-dimethylthiophene-2-yl, 3 , 4-Dimethylthiophene-2-yl, 4-chlorothiophene-2-yl, furan-2-yl, 5-methyl-furan-2-yl, 5-ethyl-furan-2-yl, 5-methoxycarbonyl-furan-2-yl, 5-chlorofuran -2-yl, 5-bromo-furan-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran -2-yl, tetrahydrofuran-3-yl, 2-phenyleth-1-yl, 1- (4-methylphenyl) eth-1-yl, 1- (3-methylphenyl) eth-1-yl, 1- (2-yl) Methylphenyl) eth-1-yl, 1- (4-chlorophenyl) eth-1-yl, 1- (3-chlorophenyl) eth-1-yl, 1- (2-chlorophenyl) eth-1-yl, 1- ( 4-trifluoromethylphenyl) eth-1-yl, 1- (3-trifluoromethylphenyl) eth-1-yl, 1 - (2-trifluoromethyl 1-phenyl) eth-1-yl, 1- (4-fluorophenyl) eth-1-yl, 1- (3-fluorophenyl) eth-1-yl, 1- (2-fluorophenyl) eth-1-yl, l- ( 4-cyanophenyl) eth-1-yl, 1- (3-cyanophenyl) eth-1-yl, 1- (2-cyanophenyl) eth-1-yl, 2- (3-fluorophenyl) eth-1-yl, 2 (4-fluorophenyl) eth-1-yl, 2- (2-fluorophenyl) eth-1-yl, 2- (2-chlorophenyl) eth-1-yl, 2 (3) Chlorophenyl) eth-1-yl, 2- (4-chlorophenyl) eth-1-yl, 2- (2-bromophenyl) eth-1-yl, 2- (3-bromophenyl) eth-1-yl, 2- ( 4-bromophenyl) eth-1-yl, 2- (2-cyanophenyl) eth-1-yl, 2- (3-cyanophenyl) eth-1-yl, 2- (4-cyanophenyl) eth-1-yl, 2 - (2-trifluoromethylphenyl) eth-1-yl, 2- (3-trifluoromethylphenyl) eth-1-yl, 2- (4-trifluoromethylphenyl) eth-1-yl, 2- (2-methoxyphenyl) eth-1-yl , 2- (3-Methoxyphenyl) eth-1-yl, 2- (4-methoxyphenyl) eth-1-yl, 2- (4-methylphenyl) eth-1-yl, 2
(2-Methylphenyl)eth-l-yl, Benzyl, (4-Fluorphenyl)methyl, (3-Fluorphenyl)methyl, (2- Fluorphenyl)methyl, (2,4-Difluorphenyl)methyl, (3,5-Difluorphenyl)methyl, (2,5- Difluorphenyl)methyl, (2,6-Difluorphenyl)methyl, (2,4,5-Trifluorphenyl)methyl, (2,4,6- Trifluorphenyl)methyl, (4-Chlorphenyl)methyl, (3-Chlorphenyl)methyl, (2-Chlorphenyl)methyl, (2,4-Dichlorphenyl)methyl, (3,5-Dichlorphenyl)methyl, (2,5-Dichlorphenyl)methyl, (2,6-(2-methylphenyl) eth-1-yl, benzyl, (4-fluorophenyl) methyl, (3-fluorophenyl) methyl, (2-fluorophenyl) methyl, (2,4-difluorophenyl) methyl, (3,5-difluorophenyl) methyl, (2,5-difluorophenyl) methyl, (2,6-difluorophenyl) methyl, (2,4,5-trifluorophenyl) methyl, (2,4,6-trifluorophenyl) methyl, (4-chlorophenyl) methyl, ( 3-chlorophenyl) methyl, (2-chlorophenyl) methyl, (2,4-dichlorophenyl) methyl, (3,5-dichlorophenyl) methyl, (2,5-dichlorophenyl) methyl, (2,6-
Dichlorphenyl)methyl, (2,4,5-Trichlorphenyl)methyl, (2,4,6-Trichlorphenyl)methyl, (4- Bromphenyl)methyl, (3-Bromphenyl)methyl, (2-Bromphenyl)methyl, (4-Iodphenyl)methyl, (3- Iodphenyl)methyl, (2-Iodphenyl)methyl, (3-Chlor-5-Trifluormethyl-pyridin-2-yl)methyl, (2- Brom-4-Fluorphenl)methyl, (2-Brom-4-Chlorphenyl)methyl, (3-Brom-4-Fluorphenyl)methyl, (3-Brom-4-Chlorphenyl)methyl, (3-Brom-5-Fluorphenyl)methyl, (3-Brom-5-Dichlorophenyl) methyl, (2,4,5-trichlorophenyl) methyl, (2,4,6-trichlorophenyl) methyl, (4-bromophenyl) methyl, (3-bromophenyl) methyl, (2-bromophenyl) -methyl, (4- Iodophenyl) methyl, (3-iodophenyl) methyl, (2-iodophenyl) methyl, (3-chloro-5-trifluoromethylpyridin-2-yl) methyl, (2-bromo-4-fluorophenol) methyl, (2-bromo 4-chlorophenyl) methyl, (3-bromo-4-fluorophenyl) methyl, (3-bromo-4-chlorophenyl) methyl, (3-bromo-5-fluorophenyl) methyl, (3-bromo-5-
Chlorphenyl)methyl, (2-Fluor-4-Bromphenyl)methyl, (2-Chlor-4-Bromphenyl)methyl, (3-Fluor- 4-Bromphenyl)methyl, (3-Chlor-4-Bromphenyl)methyl, (2-Chlor-4-Fluorphenyl)methyl, (3- Chlor-4-Fluorphenyl)methyl, (2-Fluor-3 -Chlorphenyl)methyl, (2-Fluor-4-Chlorphenyl)methyl, (2-Fluor-5-Chlorphenyl)methyl, (3-Fluor-4-Chlorphenyl)methyl, (3-Fluor-5- Chlorphenyl)methyl, (2-Fluor-6-Chlorphenyl)methyl, 2-Phenyleth-l-yl, 3-Trifluormethyl-4-Chlorophenyl) methyl, (2-fluoro-4-bromophenyl) methyl, (2-chloro-4-bromophenyl) methyl, (3-fluoro-4-bromophenyl) methyl, (3-chloro-4-bromophenyl) methyl, (2 -Chloro-4-fluorophenyl) methyl, (3-chloro-4-fluorophenyl) methyl, (2-fluoro-3-chlorophenyl) methyl, (2-fluoro-4-chlorophenyl) methyl, (2-fluoro-5-chlorophenyl ) methyl, (3-fluoro-4-chlorophenyl) methyl, (3-fluoro-5-chlorophenyl) methyl, (2-fluoro-6-chlorophenyl) methyl, 2-phenyleth-1-yl, 3-trifluoromethyl-4
Chlorphenyl, 3-Chlor-4-Trifluormethylphenyl, 2-Chlor-4-Trifluormethylphenyl, 3,5- Dfluorpyridin-2-yl, (3,6-Dichlor-pyridin-2-yl)methyl, (4-Trifluormethylphenyl)methyl, (3- Trifluormethylphenyl)methyl, (2-Trifluormethylphenyl)methyl, (4-Ethylphenyl)methyl, (3- Ethylphenyl)methyl, (2-Ethylphenyl)methyl, (4-Trifluormethoxyphenyl)methyl, (3- Trifluormethoxyphenyl)methyl, (2-Trifluormethoxyphenyl)methyl, (4-Methoxyphenyl)methyl,Chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-difluoropyridin-2-yl, (3,6-dichloropyridin-2-yl) methyl, (4-trifluoromethylphenyl) methyl, (3-trifluoromethylphenyl) methyl, (2-trifluoromethylphenyl) methyl, (4-ethylphenyl) methyl, (3-ethylphenyl) methyl, (2-ethylphenyl) methyl, (4-trifluoromethoxyphenyl) methyl, (3-trifluoromethoxyphenyl) methyl, ( 2-trifluoromethoxyphenyl) methyl, (4-methoxyphenyl) methyl,
(3-Methoxyphenyl)methyl, (2-Methoxyphenyl)methyl, (4-Methylphenyl)methyl, (3- Methylphenyl)methyl, (2-Methylphenyl)methyl, (4-Cyanophenyl)methyl, (3- Cyanophenyl)methyl, (2-Cyanophenyl)methyl, (2,4-Diethylphenyl)methyl, (3,5- Diethylphenyl)methyl, (3,4-Dimethylphenyl)methyl, (3,5-Dimethoxyphenyl)methyl, 1- Phenyleth-l-yl, l-(2,4-Dichlorphenyl)eth-l -yl, l,3-Thiazol-2-yl, 4-Methyl-l,3-thiazol-2-yl, 1,3-(3-Methoxyphenyl) methyl, (2-methoxyphenyl) methyl, (4-methylphenyl) methyl, (3-methylphenyl) methyl, (2-methylphenyl) methyl, (4-cyanophenyl) methyl, (3-cyanophenyl) methyl, ( 2-cyanophenyl) methyl, (2,4-diethylphenyl) methyl, (3,5-diethylphenyl) methyl, (3,4-dimethylphenyl) methyl, (3,5-dimethoxyphenyl) methyl, 1-phenyleth-1-yl, 1- (2,4-dichlorophenyl) eth-1-yl, l, 3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, 1,3-
Thiazol-2-yl, l-Methyl-imidazol-4-yl, 1 -Methyl- imidazol-5-yl, 1 -Ethyl-imidazol-4-yl, 1-Ethyl- imidazol-5-yl, l-iso-Propyl-imidazol-4-yl, l-iso-Propyl-imidazol-5-yl, 4- (Methylcarbonylamino)phenylmethyl, 4-(iso-Propylcarbonylamino)phenylmethyl,4-(cyclo- Propylamino)phenylmethyl, Aminophenyl, Methylaminophenyl, Ethylaminophenyl, Thiazol-2-yl, 1-methyl-imidazol-4-yl, 1-methyl-imidazol-5-yl, 1-ethyl-imidazol-4-yl, 1-ethyl-imidazol-5-yl, 1-iso Propylimidazol-4-yl, 1-isopropyl-imidazol-5-yl, 4- (methylcarbonylamino) phenylmethyl, 4- (iso -propylcarbonylamino) phenylmethyl, 4- (cyclopropylamino) phenylmethyl, aminophenyl, methylaminophenyl, ethylaminophenyl .
Dimethylaminophenyl, , 2-(5-Chlor-2-fluorphenyl)eth-l-yl, 2-(4-Chlor-2-fluorphenyl)eth-l -yl,Dimethylaminophenyl, 2- (5-chloro-2-fluorophenyl) eth-1-yl, 2- (4-chloro-2-fluorophenyl) eth-1-yl,
2-(2-Chlor-4-fluorphenyl)eth- 1 -yl, 2-(2-Chlor-5-fluorphenyl)eth- 1 -yl, 2-(3 -Chlor-2- fluorphenyl)eth-l-yl, 2-(3-Chlor-4-fluorphenyl)eth-l-yl, 2-(3-Chlor-5-fluorphenyl)eth-l-yl, 2- (4-Chlor-3 -fluorphenyl)eth- 1 -yl, 2-(2-Chlor-6-fluorphenyl)eth- 1 -yl, 2-(2,6-Difluorphenyl)eth- 1 - yl, 2-(2,5-Difluorphenyl)eth-l -yl , 2-(2,4-Difluorphenyl)eth-l -yl, 2-(2,6-Dichlorphenyl)eth-l -yl, 2-(2,5-Dichlorphenyl)eth-l -yl , 2-(2,4-Dichlorphenyl)eth-l -yl, 2-(2,3-Dichlorphenyl)eth-l -yl, 2- (3,5-Dichlorphenyl)eth-l -yl, 2-(4-Nitrophenyl)eth-l -yl, 2-(2-Nitrophenyl)eth-l -yl steht. 2- (2-chloro-4-fluorophenyl) eth-1-yl, 2- (2-chloro-5-fluorophenyl) eth-1-yl, 2- (3-chloro-2-fluorophenyl) eth-1-yl , 2- (3-chloro-4-fluorophenyl) eth-1-yl, 2- (3-chloro-5-fluorophenyl) eth-1-yl, 2 (4-chloro-3-fluorophenyl) eth-1-yl, 2- (2-chloro-6-fluorophenyl) eth-1-yl, 2- (2,6-difluorophenyl) eth-1-yl, 2- 2,5-difluorophenyl) eth-1-yl, 2- (2,4-difluorophenyl) eth-1-yl, 2- (2,6-dichlorophenyl) eth-1-yl, 2- (2,5-dichlorophenyl ) eth-1-yl, 2- (2,4-dichlorophenyl) eth-1-yl, 2- (2,3-dichlorophenyl) eth-1-yl, 2- (3,5-dichlorophenyl) eth-1 - yl, 2- (4-nitrophenyl) eth-1-yl, 2- (2-nitrophenyl) eth-1-yl.
Einige der zuvor genannten substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I) sind ebenfalls noch nicht im Stand der Technik bekannt. Somit gelten als weiterer Teil der Erfindung substituierte N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'-heteroaryldiaminoalkane der allgemeinen Formel (I) oder deren Salze, Some of the abovementioned substituted N-sulfonyl-N'-aryldiaminoalkanes and N-sulfonyl-N'-heteroaryldiaminoalkanes of the general formula (I) are likewise not yet known in the prior art. Thus, as a further part of the invention substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I) or salts thereof,
Figure imgf000027_0001
worin
Figure imgf000027_0001
wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Halogen, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-Cg)- Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl- (Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl-(Ci-C8)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C- (Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkinyl, Heteroaryl-(Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)- alkyl](aryl)silyl-(C2-C8)-alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, (C3-C8)- Cycloalkyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)-alkenyl, Heterocyclyl- (C2-C8)-alkenyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkylaminosulfonylamino, (C3-C8)-Cycloalkylaminosulfonylamino, Tris- [(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)-alkyl]silyl steht, R 1 represents hydrogen, halogen, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -Cio) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (Ci-Cg) - Haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl (Ci-C8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, (Ci-C8) alkylcarbonyl (Ci-C8) - alkyl, C (0) OR 12, C (O) NR 10 R u, C (0) R 12, -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N (O) C- (C 1 -C 8 ) -alkyl, R 10 R u N- (Ci -C 8) alkyl, aryl (Ci-C 8) alkynyl, heteroaryl (C i-C 8) alkynyl, heterocyclyl (Ci-C8) -alkynyl, tris - [(Ci-C 8) alkyl] (C silyl- 2 -C 8) -alkynyl, - bis [(Ci-C 8) alkyl] (aryl) silyl (C 2 -C 8 ) alkynyl, bis-aryl [(Ci-C 8 ) alkyl] silyl (C 2 -C 8 ) alkynyl, (C 3 -C 8 ) - cycloalkyl- (C 2 -C 8 ) -alkynyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8) alkenyl, (C3-C8) cycloalkyl (C 2 -C 8) alkenyl, (Ci-C 8) alkoxy (Ci-C 8) alkoxy (Ci-C 8 ) -alkyl, (C 1 -C 8 ) -alkylaminosulfonylamino, (C 3 -C 8 ) -cycloalkylaminosulfonylamino, tris [(C 1 -C 8 ) -alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, Cyano-(Ci-C8)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C 8) -alkyl, (C3-C8) cycloalkyl, cyano (Ci-C 8) - alkyl, (C 3 -C 8) -cycloalkyl- ( C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C8)- alkylsulfonyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cg)- Haloalkyl, Halo-(C2-C8)-alkinyl, Halo-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkylsulfonyl, Heterocyclyl- (Ci-C8)-alkylsulfonyl, (C4-C8)-Cycloalkenyl, (C4-C8)-Cycloalkenyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-C8)-Alkylaminocarbonyl, (C3-C8)- Cycloalkylaminocarbonyl, Bis-[(Ci-C8)-Alkyl]aminocarbonyl stehen, Heteroarylsulfonyl, (C3-C8) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (Ci-C8) - alkylsulfonyl, (Ci-C 8) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C8) - cycloalkylcarbonyl, heterocyclylcarbonyl, (C -C 8) alkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci- Cg) - haloalkyl, halo (C 2 -C 8) alkynyl, halo (C 2 -C 8) alkenyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, amino, ( C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkylsulfonyl, heterocyclyl- (C 1 -C 8 ) -alkylsulfonyl, (C 4 -C 8) cycloalkenyl, (C 4 -C 8) cycloalkenyl (Ci-C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, (Ci- C 8) alkylaminocarbonyl, (C3-C8) - cycloalkylaminocarbonyl, bis - [(Ci-C 8) -alkyl] aminocarbonyl stand,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, Halogen,R 3, R 4, R 7 and R 8 independently represent hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halogen,
(Ci-C8)-Haloalkyl, Aryl, Heteroaryl, (C3-C8)-Cycloalkyl, Heterocyclyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)- Haloalkylthio-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino-(Ci-C8)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)- alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, (Ci-C8) haloalkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, heterocyclyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) - Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, bis [ (C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (Ci-C 8) alkyl, R 10 R u N (O) C- (Ci-C 8) alkyl, R 10 R u N- (Ci-C8) - alkyl, , m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden,  form part-saturated, optionally heteroatom-interrupted and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R5 für Heteroaryl, Heterocyclyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl- (Ci-Cg)-alkyl steht, R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 8) -alkyl, heteroaryl- (C 1 -C 8) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl,R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 8) -alkyl,
(C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR12, S02R13, (Ci-C8)-Alkyl-HN02S-, (C3-C8)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl, Heteroaryl-(C i-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 8 ) - Alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 8) alkyl, COR 12, S0 2 R 13, (Ci-C8) alkyl-S- HN0 2, (C 3 -C 8) cycloalkyl HN0 2 S-, heterocyclyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl, heteroaryl- (C iC 8) alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, heterocyclyl (Ci-C 8) -alkyl,
R12 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)-Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- Alkoxycarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C8)-alkyl steht und R 12 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) - haloalkyl (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -Cio) -Halocycloalkenyl, (Ci-C 8) alkoxy (Ci-C 8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) haloalkyl, aryl, aryl (Ci-C 8 ) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (Ci-C 8 ) -alkyl, (C 4 -Cio) -cycloalkenyl- (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, (Ci-C 8) alkyl, (C 2 -C 8) -Alkenyloxycarbonyl- (Ci-C 8) alkyl, aryl (Ci-C 8) Alkoxycarbonyl- (C 1 -C 8 ) -alkyl, hydroxycarbonyl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl and
R13 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C i-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkyl, (Ci-Cg)-Alkoxy-(Ci-Cg)-haloalkyl, Aryl, Aryl-(Ci-Cg)-alkyl, Heteroaryl, Heteroaryl- (Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (C1-C10) - haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 1 -C 10) -cycloalkenyl, (C 4 -Cio) -halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) - alkyl, (Ci-Cg) -alkoxy- (Ci-Cg) -haloalkyl, aryl, aryl- (Ci-Cg) -alkyl, heteroaryl, heteroaryl- (Ci-C 8 ) -alkyl, heterocyclyl- (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 8 ) -alkyl, (C 4 -C 10 ) -cycloalkenyl- (C 1 -C 8 ) -alkyl, NR 10 R U.
Bevorzugter weiterer Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Preferred further subject of the invention are compounds of general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Fluor, Chlor, Brom, lod, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-Cv)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C7)- Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-C10)- Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-Cv)- alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)- Alkylcarbonyl-(Ci-C7)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C- (Ci-C7)-alkyl, R10RuN(O)C-(Ci-C7)-alkyl, R10RuN-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkinyl, Heteroaryl-(Ci-C7)-alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, Tris-[(Ci-C7)-alkyl]silyl-(C2-C7)- alkinyl, Bis-[(Ci-C7)-alkyl](aryl)silyl-(C2-C7)-alkinyl, Bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)- alkinyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkinyl, Aryl-(C2-C7)-alkenyl, Heteroaryl-(C2-C7)-alkenyl, Heterocyclyl-(C2-C7)-alkenyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminosulfonylamino, (C3-C7)-R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, NR 10 R U , OR 12 , S (0) m R 13 , thiocyanato, isothiocyanato, (C 1 -C 4) -alkyl, (C 2 -C 7 ) alkenyl, (C 2 -C 7 ) alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) Haloalkoxy- (C 1 -C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, aryl, aryl- (C 1 -C 4 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 4 -alkyl) 7) alkyl, (C3-C7) -cycloalkyl- (Ci-C7) alkyl, (C4-C10) - cycloalkenyl (Ci-C7) alkyl, heterocyclyl, heterocyclyl (Ci-C 7) alkyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) -alkylthio (Ci-C 7) alkyl, (Ci-C 7) -Haloalkylthio- (C -C 7) alkyl, (Ci-C7) - alkylcarbonyl (Ci-C7) alkyl, C (0) OR 12, C (O) NR 10 R u, C (0) R 12, -C = NOR 12 , R 12 0 (0) C- (C 1 -C 7 ) -alkyl, R 10 R u N (O) C- (C 1 -C 7 ) -alkyl, R 10 R u N- (Ci-C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkynyl, heteroaryl (Ci-C7) alkynyl, heterocyclyl (Ci-C7) alkynyl, tris - [(Ci-C 7) alkyl] silyl (C 2 -C 7) - alkynyl, - bis [(Ci- C 7) alkyl] (aryl) silyl (C 2 -C 7) alkynyl, bis-aryl [(Ci-C 7) alkyl] silyl (C 2 -C 7) - alkynyl, (C 3 - C 7 ) -cycloalkyl- (C 2 -C 7 ) -alkynyl, aryl- (C 2 -C 7 ) -alkenyl, heteroaryl- (C 2 -C 7 ) -alkenyl, heterocyclyl- (C 2 -C 7 ) - alkenyl, (C 3 -C 7) cycloalkyl (C 2 -C 7) alkenyl, (Ci-C7) alkoxy (Ci-C7) - alkoxy- (Ci-C7) alkyl, ( Ci-C 7) -Alkylaminosulfonylamino, (C 3 -C 7) -
Cycloalkylaminosulfonylamino, Tris-[(Ci-C7)-alkyl]silyl, Bis-[(Ci-C7)-alkyl](aryl)silyl, Bis- aryl[(Ci-C7)-alkyl]silyl steht, Cycloalkylaminosulfonylamino, tris - [(C 1 -C 7 ) -alkyl] silyl, bis - [(C 1 -C 7 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 7 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, Cyano-(Ci-C7)- alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl, cyano (Ci-C7) - alkyl, (C 3 -C 7) cycloalkyl (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C7)- alkylsulfonyl, (Ci-C7)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C7)-Alkoxycarbonyl, Aryl-(Ci-C7)- alkoxycarbonyl, (Ci-C7)-Haloalkylcarbonyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Haloalkyl, Halo-(C2-C7)-alkinyl, Halo-(C2-C7)-alkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Amino, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-Cv)-alkyl, Heteroaryl-(Ci-C7)-alkylsulfonyl, Heterocyclyl- (Ci-C7)-alkylsulfonyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Cycloalkenyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl, (C2-Cv)-Alkinyloxycarbonyl, (Ci-C7)-Alkylaminocarbonyl, (C3-C7)- Cycloalkylaminocarbonyl, Bis-[(Ci-C7)-Alkyl]aminocarbonyl stehen, Heteroarylsulfonyl, (C 3 -C 7) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (Ci-C7) - alkylsulfonyl, (Ci-C 7) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 3 -C 7) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C 7) alkoxycarbonyl, aryl (Ci-C7) - alkoxycarbonyl, (Ci-C 7) haloalkylcarbonyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, ( C1-C7) - haloalkyl, halo (C 2 -C 7) alkynyl, halo (C 2 -C 7) alkenyl, (Ci-C7) alkoxy (Ci-C7) alkyl, amino . (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkoxy- (C 1 -C 4) -alkyl, heteroaryl- (C 1 -C 7 ) -alkylsulfonyl, heterocyclyl- (C 1 -C 7 ) -alkylsulfonyl, (C 4 - C 7 ) -cycloalkenyl, (C 4 -C 7 ) -cycloalkenyl- (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyloxycarbonyl, (C 2 -C 4 ) -alkynyloxycarbonyl, (C 1 -C 7 ) -alkylaminocarbonyl, (C3 -C7) - cycloalkylaminocarbonyl, bis - [(Ci-C7) -alkyl] aminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, Fluor, Chlor, Brom, Iod, (Ci-C7)-Haloalkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, Heterocyclyl, (C 1-C7)- Alkoxy-(C 1 -C7)-alkyl, (C 1-C7)- Alkylthio-(C i-C7)-alkyl, (C i-C7)-Haloalkoxy-(C 1 -C7)- alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, Bis-[(Ci-C7)-Alkyl]amino-(Ci-C7)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C7)-alkyl, R10RuN(O)C-(Ci-C7)-alkyl,R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, (C 1 -C 7) -alkyl, (C 2 -C 7) -alkenyl, fluorine, chlorine, bromine, iodine, (C 1 -C 7) -haloalkyl, aryl, Heteroaryl, (C 3 -C 7 ) -cycloalkyl, heterocyclyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C iC 7) haloalkoxy (C 1 -C 7) - alkyl, (Ci-C7) -Haloalkylthio- (Ci-C7) alkyl, - bis [(Ci-C7) alkyl] amino- (Ci-C7 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 7 ) -alkyl, R 10 R u N (O) C- (C 1 -C 7) -alkyl,
R10RuN-(Ci-C7)-alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R 10 is R u N- (C 1 -C 7) -alkyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or R 3 and R 7 with the Kohlenstoffatomem to which they are attached, a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further form substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden,  form part-saturated, optionally heteroatom-interrupted and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R5 für Heteroaryl, Heterocyclyl, Aryl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl- (Ci-C7)-alkyl steht, R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl,R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 7) -alkyl,
(C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)- haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, COR12, S02R13, (Ci-C7)-Alkyl-HN02S-, (C3-C7)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-Alkoxycarbonyl, Heteroaryl-(C i-C7)-Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen (C 2 -C 7) alkenyl, (C2-C7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-Cio) -haloalkyl, (C2-C7) haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (Ci-C 7 ) -alkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl , heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 -Cio) cycloalkenyl (C 7) alkyl, COR 12 , S0 2 R 13 , (C 1 -C 7 ) -alkyl-HNO 2 S-, (C 3 -C 7 ) -cycloalkyl-HNO 2 S-, heterocyclyl, (C 1 -C 7 ) -alkoxycarbonyl- (Ci-C 7) alkyl, (C1-C7) - alkoxycarbonyl, aryl (Ci-C7) alkoxycarbonyl (Ci-C7) alkyl, aryl (Ci-C 7) alkoxycarbonyl, heteroaryl- (C 7 iC ) alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C 2 are -C 7) -alkynyloxycarbonyl, heterocyclyl (Ci-C7) alkyl
R12 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)-Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- Alkoxycarbonyl-(Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C7)-alkyl steht und R 12 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (C1-C10) - haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -Cio) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C 7 ) alkyl, heteroaryl, heteroaryl (Ci-C 7 ) alkyl, (C 3 -C 7 ) cycloalkyl (Ci-C 7 ) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 7) alkyl, (C 1 -C 7) - alkoxycarbonyl (Ci-C7) alkyl, (C 2 -C 7) -Alkenyloxycarbonyl- (Ci-C7) alkyl, aryl (Ci-C 7) Alkoxycarbonyl- (C 1 -C 7 ) -alkyl, hydroxycarbonyl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl and
R13 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (C1-C10)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy-(Ci-C7)- alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl- (Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C7)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (C1-C10) - haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -haloalkynyl, Cio) -Halocycloalkenyl, (Ci-C7) alkoxy (Ci-C7) - alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C 7 ) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, heterocyclyl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C4- C10) - cycloalkenyl (Ci-C7) alkyl, NR 10 R U stands.
Besonders bevorzugter weiterer Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Particularly preferred further subject of the invention are compounds of general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C6)- Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-C10)- Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)- alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-Cö)- alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)- Alkylcarbonyl-(Ci-C6)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C- (Ci-C6)-alkyl, R10RuN(O)C-(Ci-C6)-alkyl, R10RuN-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)- alkinyl, Bis-[(Ci-C6)-alkyl](aryl)silyl-(C2-C6)-alkmyl, Bis-aryl[(Ci-C6)-alkyl]silyl-(C2-C6)- alkinyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkinyl, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)-alkenyl, Heterocyclyl-(C2-C6)-alkenyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylaminosulfonylamino, (C3-C6)-R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-C 6) -alkyl, (C 2 - C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 6) - Haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (Ci -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, aryl , aryl (Ci-C 6) - alkyl, heteroaryl, heteroaryl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C4-C10) - cycloalkenyl - (C 1 -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 4 ) -alkyl 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylcarbonyl- (C 1 -C 6 ) -alkyl, C (O) OR 12 , C (O ) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 6 ) -alkyl, R 10 R u N (O) C- (Ci-C 6 ) -alkyl, R 10 R u N- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkynyl, heteroaryl- (C 1 -C 6 ) -alkynyl, heterocyclyl- (C 1 -C 6 ) -alkynyl, tris - [(C 1 -C 6 ) alkyl] silyl (C 2 -C 6 ) alkynyl, bis - [(C 1 -C 6 ) alkyl] (aryl) silyl (C 2 -C 6 ) alkynyl , Bis-aryl [(C 1 -C 6 ) -alkyl] silyl (C 2 -C 6 ) -alkynyl, (C 3 -C 6 ) -cycloalkyl- (C2 -C 6 ) -alkynyl, aryl- (C 2 -C 6 ) -alkenyl, heteroaryl- (C 2 -C 6 ) -alkenyl, heterocyclyl- (C 2 -C 6 ) -alkenyl, (C 3 -C 6 ) -cycloalkyl- (C 2 - C 6 ) -alkenyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylaminosulfonylamino, (C 3 -C 6 ) -
Cycloalkylaminosulfonylamino, Tris-[(Ci-C6)-alkyl]silyl, Bis-[(Ci-C6)-alkyl](aryl)silyl, Bis- aryl[(Ci-C6)-alkyl]silyl steht, Cycloalkylaminosulfonylamino, tris - [(C 1 -C 6 ) -alkyl] silyl, bis - [(C 1 -C 6 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 6 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, Cyano-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C6) alkyl, (C3-C6) cycloalkyl, cyano (Ci-C6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C6)- alkylsulfonyl, (Ci-C6)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C6)-Alkoxycarbonyl, Aryl-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Ce)- Haloalkyl, Halo-(C2-C6)-alkinyl, Halo-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkylsulfonyl, Heterocyclyl- (Ci-C6)-alkylsulfonyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, Bis-[(Ci-C6)-Alkyl]aminocarbonyl stehen, 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 6) - Alkoxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl, (C 1 -C 6) -haloalkylcarbonyl, (C 2 -C 6) -alkenyl, (C 2 -C 6) -alkynyl, (C 1 -C 6) -haloalkyl, halo- (C 2 - C 6) alkynyl, halo (C 2 -C 6) alkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, amino, (Ci-C6) alkoxy (Ci-C6 ) -alkoxy- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkylsulfonyl, heterocyclyl- (C 1 -C 6 ) -alkylsulfonyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6 ) - Cycloalkenyl- (C 1 -C 6 ) -alkyl, (C 2 -C 6 ) -alkenyloxycarbonyl, (C 2 -C 6 ) -alkynyloxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl, bis [(Ci -C 6) -alkyl] aminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, Fluor, Chlor, Brom, Iod, (Ci-C6)-Haloalkyl, Aryl, Heteroaryl, (C3-C6)-Cycloalkyl, Heterocyclyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)- alkyl, (Ci-C6)-Haloalkylthio-(Ci-C7)-alkyl, Bis-[(Ci-C6)-Alkyl]amino-(Ci-C6)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C6)-alkyl, R10RuN(O)C-(Ci-C6)-alkyl, R10RuN-(Ci-C6)-alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl, fluorine, chlorine, bromine, iodine, (C 1 -C 6) -haloalkyl, aryl, Heteroaryl, (C 3 -C 6 ) -cycloalkyl, heterocyclyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, (Ci -C 6) haloalkoxy (Ci-C 6) - alkyl, (Ci-C 6) -Haloalkylthio- (Ci-C7) alkyl, - bis [(Ci-C6) alkyl] amino- (Ci- C 6 ) alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C (Ci-C 6 ) alkyl , R 10 R u is N (O) C- (C 1 -C 6 ) -alkyl, R 10 is R u N- (C 1 -C 6 ) -alkyl, m is 0, 1 or 2, n is 1, 2 or 3,
R und R mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R and R with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden,  form part-saturated, optionally heteroatom-interrupted and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R5 für Heteroaryl, Heterocyclyl, Aryl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl- (Ci-C6)-alkyl steht, R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl,R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 6) -alkyl,
(C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, COR12, S02R13, (Ci-C6)-Alkyl-HN02S-, (C3-C6)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl, Aryl-(Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl, Heteroaryl-(C i-Ce)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-Cio) -haloalkyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 6 ) - Alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 6 ) -alkyl, C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl ( C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 6 ) -alkyl, COR 12 , SO 2 R 13 , (Ci-C 6) alkyl-S- HN0 2, (C 3 -C 6) cycloalkyl-HN0 2 S-, heterocyclyl, (Ci-C 6) alkoxycarbonyl (Ci-C 6) alkyl, ( C 1 -C 6 ) - alkoxycarbonyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, heterocyclyl- (C 1 -C 6) -alkyl,
R12 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C6)-alkyl steht und R 12 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-Cio) - haloalkyl , (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) ) -Halocycloalkenyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -haloalkyl, aryl, aryl- (C 1 -C 6) -alkyl, heteroaryl, heteroaryl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 4 -Cio) cycloalkenyl (Ci-C 6) alkyl, (Ci-C 6 ) - alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- (Ci -C 6) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl and
R13 für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C6)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-Cio) - haloalkyl , (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) ) -Halocycloalkenyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -haloalkyl, aryl, aryl- (C 1 -C 6) -alkyl, heteroaryl, Heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 10) -cycloalkenyl (C 1 -C 4 ) -alkyl C 6 ) alkyl, NR 10 R U.
Ganz besonders bevorzugter weiterer Erfindungsgegenstand sind Verbindungen der allgemeinen Formel (I), worin Very particularly preferred further subject of the invention are compounds of general formula (I) wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, Hydroxy, Amino, Methylamino, R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, amino, methylamino,
Ethylamino, Dimethylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Methoxycarbonylmethylamino, Methoxycarbonylethylamino,  Ethylamino, dimethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino,
Ethoxycarbonylmethylamino, Ethoxycarbonylethylamino, Methoxycarbonylamino,  Ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino,
Ethoxycarbonylamino, tert-Butyloxycarbonylamino, Phenylamino, N-Piperidinyl, N- Pyrrolidinyl, N-Morpholinyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert- Butyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, tert-Butyloxycarbonyloxy,  Ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, N-piperidinyl, N-pyrrolidinyl, N-morpholinyl, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert-butyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy,
Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n-Propylaminocarbonyloxy, iso- propylaminocarbonyloxy, Benzylaminocarbonyloxy, Phenylaminocarbonyloxy,  Methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy,
Cyclopropylaminocarbonyloxy, Cyclobutylaminocarbonyloxy, Cyclopentylaminocarbonyloxy, Cyclohexylaminocarbonyloxy, Dimethylaminocarbonyloxy, Trifluormethyloxy,  Cyclopropylaminocarbonyloxy, cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, trifluoromethyloxy,
Difluormethyloxy, 2,2-Difluorethyloxy, 2,2,2-Trifluorethyloxy, Methylthio, Ethylthio, n- Propylthio, iso-Propylthio, Methyl, Ethyl, n-Propyl, 1 -Methylethyl, n-Butyl, 1-Methylprop-l-yl, 2- Methylprop-l-yl, 1,1-Dimethyleth-l -yl, n-Pentyl, 1 -Methylbutyl, 2-Methylbutyl, 3- Methylbutyl, 1,1-Dimethylprop-l -yl, 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-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3- Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1 , 1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 - Ethyl-l-methylpropyl, 1 -Ethyl-2-methylpropyl, 3,3-Difluorcyclobut-l-yl, 3-Fluorcyclobut-l-yl, 1-Fluorcyclobut-l-yl, 2,2-Difluorcycloprop-l-yl, 1-Fluorcycloprop-l-yl, 2-Fluorcycloprop-l -yl, 4-Fluorcyclohexyl, 4,4-Difluorcyclohexyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Methylcycloprop-l-yl, 2-Methylcycloprop-l-yl, 2,2-Dimethylcycloprop-l-yl, 2,3- Dimethylcyclopropyl, 1 -Cyanopropyl, 2-Cyanopropyl, 1 -Methylcyclobutyl, 2-Methylcyclobutyl,Difluoromethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, isopropylthio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylprop-l yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-yl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylprop-1-yl, 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-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-one yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcyclopropyl 1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl,
3 - Methylcyclobutyl, 3,3-Dimethylcyclobutyl, 1 -Cyanocyclobutyl, 2-Cyanocyclobutyl, 3- Cyanocyclobutyl, 1 -Allylcyclopropyl, 1 -Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1- Ethylcyclopropyl, 1 -Methylcyclohexyl, 2-Methylcyclohexyl, 3-Methylcyclohexyl, 1- Methoxycyclohexyl, 2-Methoxycyclohexyl, 3-Methoxycyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1 , 1 ,2,2-Tetrafluorethyl, Heptafluor-n-propyl, Heptafluor-iso-propyl, Nonafluorbutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluorobutyl,
Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl,
Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, 3,3,3-Trifluor-n-propyl, Methoxycarbonyl, Bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl,
Ethoxycarbonyl, iso-Propyloxycarbonyl, n-Propyloxycarbonyl, tert-Butyloxycarbonyl, Ethoxycarbonyl, iso-propyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl,
Benzyloxycarbonyl, Allyloxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n- Propylaminocarbonyl, iso-Propylaminocarbonyl, Benzylaminocarbonyl, Phenylaminocarbonyl, Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentylaminocarbonyl, Benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, iso -propylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl,
Cyclohexylaminocarbonyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, Cyclohexylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,
Allylaminocarbonyl, Pentafluorthio, Methoxydifluormethyl, Ethoxydifluormethyl, n- Propyloxydifluormethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n- propyl, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, Ethoxyethyl, Methoxyethyl, n- Propyloxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, 1-Methoxyeth-l-yl, 1-Methoxyprop-l-yl, l-Ethoxyeth-l-yl, 2-Methoxyprop-2-yl, 2-Ethoxyprop-2-yl, Methylthiomethyl, Methylthioethyl, Methylthio-n-propyl, Ethylthiomethyl, Trifluormethylthiomethyl, Petntafluorethylthiomethyl, Trifluormethylthioethyl, Trifluormethylthio-n-propyl, Methoxycarbonylmethyl, Allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-1-yl, 1-methoxyprop-1-yl, 1-ethoxyeth-1-yl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, methylthiomethyl, methylthioethyl, methylthio-n-propyl, Ethylthiomethyl, trifluoromethylthiomethyl, petntafluoroethylthiomethyl, trifluoromethylthioethyl, trifluoromethylthio-n-propyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, tert-Butyloxycarbonylethyl, Ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, tert-butyloxycarbonylethyl,
Hydroxycarbonylmethyl, Hydroxycarbonylethyl, Hydroxycarbonyl, Hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl,
Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, n-Propylaminocarbonylmethyl, iso- Propylaminocarbonylmethyl, Benzylaminocarbonylmethyl, Phenylaminocarbonylmethyl, Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl, Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl, Methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, iso-propylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl,
Dimethylaminocarbonylmethyl, Diethylammocarbonylmethyl, Allylammocarbonylmethyl, Methylaminomethyl, Dimethylaminomethyl, Diethylaminomethyl, Ethylaminomethyl, iso- Propylaminomethyl, n-Propylaminomethyl, n-Butylaminomethyl, Methylaminoethyl,  Dimethylaminocarbonylmethyl, diethylammocarbonylmethyl, allylammocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, iso-propylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl,
Dimethylaminoethyl, Diethylaminoethyl, N-Pyrrolidinylmethyl, N-Piperidinylmethyl steht,  Dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, N-piperidinylmethyl,
R2 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1 - Methyl-prop-l-yl, 2-Methyl-prop-l-yl, n-Pentyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanomethyl, 2-Cyanoeth-l-yl, 1-Cyano-eth-l-yl, 3-Cyanoprop-l-yl, R 2 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methyl-prop-1-yl, 2-methyl-prop-1-yl, n-pentyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanomethyl, 2-cyanoeth-1-yl, 1-cyano-eth-1-yl, 3-cyanoprop-1-yl,
Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Cyclopentylmethyl,  Cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Methylsulfonyl, Ethylsulfonyl, iso-Propylsulfonyl, n-Propylsulfonyl, n- Butylsulfonyl, 1-Methylprop-l-yl, 2-Methylprop-l -yl, 1,1-Dimethyleth-l-ylsulfonyl,  Cyclohexylmethyl, methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsulfonyl,
Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl, Cyclohexylsulfonyl,  Cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl,
Phenylsulfonyl, p-Cl-Phenylsulfonyl, m-Cl-Phenylsulfonyl, p-Cl-Phenylsulfonyl, p-F- Phenylsulfonyl, m-F-Phenylsulfonyl, p-F-Phenylsulfonyl, p-Cyano-Phenylsulfonyl, m-Cyano- Phenylsulfonyl, p-Cyano-Phenylsulfonyl, p-Methylphenylsulfonyl, m-Methylphenylsulfonyl, p- Methylphenylsulfonyl, p-Trifluormethylphenylsulfonyl, m-Trifluormethylphenylsulfonyl, p- Trifluormethylphenylsulfonyl, Benzylsulfonyl, p-Cl-Phenylmethylsulfonyl, m-Cl- Phenylmethylsulfonyl, p-Cl-Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, m-F- Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, m-Cyano- Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, m- Methyl-phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, m-Trifluormethyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, tert.-Butylcarbonyl, Phenylcarbonyl, p-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, o-Cl-Phenylcarbonyl, p-F- Phenylcarbonyl, m-F-Phenylcarbonyl, o-F-Phenylcarbonyl, Pyridin-2-ylcarbonyl, Pyridin-3- ylcarbonyl, Pyridin-4-ylcarbonyl, 4-Trifluormethyl-pyridin-3-ylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexylcarbonyl, Methoxycarbonyl,  Phenylsulfonyl, p-Cl-phenylsulfonyl, m-Cl-phenylsulfonyl, p-Cl-phenylsulfonyl, pF-phenylsulfonyl, mF-phenylsulfonyl, pF-phenylsulfonyl, p-cyano-phenylsulfonyl, m-cyano-phenylsulfonyl, p-cyano-phenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, p-methylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, m-trifluoromethylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, benzylsulfonyl, p-Cl-phenylmethylsulfonyl, m-Cl-phenylmethylsulfonyl, p-Cl-phenylmethylsulfonyl, pF-phenylmethylsulfonyl, mF- Phenylmethylsulfonyl, p-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, m-cyano-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, p-methylphenylmethylsulfonyl, m-methylphenylmethylsulfonyl, p-methylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, m- Trifluoromethylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, methylcarbonyl, ethylcarbonyl, iso -propylcarbonyl, tert -butylcarbonyl, phenylcarbonyl, p-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, o-Cl-P henylcarbonyl, pF-phenylcarbonyl, mF-phenylcarbonyl, oF-phenylcarbonyl, pyridin-2-ylcarbonyl, pyridin-3-ylcarbonyl, pyridin-4-ylcarbonyl, 4-trifluoromethylpyridin-3-ylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoxycarbonyl,
Ethoxycarbonyl, tert-Butyloxycarbonyl, Benzyloxycarbonyl, Trifluormethylcarbonyl,  Ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, trifluoromethylcarbonyl,
Difluormethylcarbonyl, Allyl, Propargyl, 2,2-Difluorethyl, 3,3,3-Trifluorethyl, Methoxymethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxyethyl, Ethoxymethyl, Ethoxy-n-propyl, Amino, Methylaminocarbonyl, Ethylaminocarbonyl, Dimethylaminocarbonyl stehen,  Difluoromethylcarbonyl, allyl, propargyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, methoxymethyl, methoxyethyl, methoxy-n-propyl, ethoxyethyl, ethoxymethyl, ethoxy-n-propyl, amino, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n- Butyl, 1-Methylprop-l-yl, 2-Methylprop-l-yl, tert-Butyl, Trifluormethyl, Difluormethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl stehen, m für 0, 1 oder 2 steht, n für 1, 2 oder 3 steht, R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylprop-1-yl, 2-methylprop-1-yl, tert-butyl Butyl, trifluoromethyl, difluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 7 form the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden und R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, and
R5 für Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyridazin-3-yl, Pyridazin-4-yl, R 5 is pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyridazin-3-yl, pyridazin-4-yl,
Pyrimidin-2-yl, Pyrimidin-5-yl, Pyrimidin-4-yl, Pyridazin-3-ylmethyl, Pyridazin-4-ylmethyl, Pyrimidin-2-ylmethyl, Pyrimidin-5-ylmethyl, Pyrimidin-4-ylmethyl, Pyrazin-2-ylmethyl, 3- Chlor-Pyrazin-2-yl, 3-Brom-Pyrazin-2-yl, 3-Methoxy-Pyrazin-2-yl, 3-Ethoxy-Pyrazin-2-yl, 3- Trifluormethylpyrazin-2-yl, 3-Cyanopyrazin-2-yl, Naphth-2-yl, Naphth-l-yl, Chinolin-4-yl, Chinolin-6-yl, Chinolin-8-yl, Chinolin-2-yl, Chinoxalin-2-yl, 2-Naphthylmethyl, 1- Naphthylmethyl, Chinolin-4-ylmethyl, Chinolin-6-ylmethyl, Chinolin-8-ylmethyl, Chinolin-2- ylmethyl, Chinoxalin-2-ylmethyl, Pyrazin-2-ylmethyl, 4-Chloropyridin-2-yl, 3-Chloropyridin-4- yl, 2-Chloropyridin-3-yl, 2-Chloropyridin-4-yl, 2-Chlorpyridin-5-yl, 2,6-Dichlorpyridin-4-yl, 3- Chlorpyridin-5-yl, 3,5-Dichlorpyridin-2-yl, 3-Chlor-5-Trifluormethylpyridin-2-yl, (4- Chloropyridin-2-yl)methyl, (3-Chloropyridin-4-yl)methyl, (2-Chloropyridin-3-yl)methyl, (2- Chloropyridin-4-yl)methyl, (2-Chlorpyridin-5-yl)methyl, (2,6-Dichlorpyridin-4-yl)methyl, (3- Chlorpyridin-5-yl)methyl, (3,5-Dichlorpyridin-2-yl)methyl, Thiophen-2-yl, Thiophen-3-yl, 5- Methylthiophen-2-yl, 5-Ethylthiophen-2-yl, 5-Chlorthiophen-2-yl, 5-Bromthiophen-2-yl, 4- Methylthiophen-2-yl, 3-Methylthiophen-2-yl, 5-Fluorthiophen-3-yl, 3,5-Dimethylthiophen-2-yl, 3-Ethylthiophen-2-yl, 4,5-Dimethylthiophen-2-yl, 3,4-Dimethylthiophen-2-yl, 4-Chlorthiophen- 2-yl, Furan-2-yl, 5-Methylfuran-2-yl, 5-Ethylfuran-2-yl, 5-Methoxycarbonylfuran-2-yl, 5- Chlorfuran-2-yl, 5-Bromfuran-2-yl, Thiophan-2-yl, Thiophan-3-yl, Sulfolan-2-yl, Sulfolan-3-yl, Tetrahydrothiopyran-4-yl, Tetrahydropyran-4-yl, Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, 2- Phenyleth-l-yl, l-(4-Methylphenyl)eth-l -yl, l-(3-Methylphenyl)eth-l-yl, l-(2- Methylphenyl)eth-l-yl, l-(4-Chlorphenyl)eth-l-yl, l-(3-Chlorphenyl)eth-l-yl, l-(2- Chlorphenyl)eth- 1 -yl, 1 -(4-Trifluormethylphenyl)eth- 1 -yl, 1 -(3 -Trifluormethylphenyl)eth- 1 -yl,Pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazine 2-ylmethyl, 3-chloro-pyrazino-2-yl, 3-bromo-pyrazino-2-yl, 3-methoxy-pyrazino-2-yl, 3-ethoxy-pyrazino-2-yl, 3-trifluoromethylpyrazine-2 yl, 3-cyanopyrazino-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxaline-2 yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazine-2-ylmethyl, 4-chloropyridine 2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridine 5-yl, 3,5-dichloropyridin-2-yl, 3-chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl) methyl, (3-chloropyridin-4-yl) methyl, (2 -Chloropyridin-3-yl) methyl, (2-chloropyridin-4-yl) methyl, (2-chloropyridin-5-yl) methyl, (2,6-dichloropyridin-4-yl) methyl, (3-Chl orpyridin-5-yl) methyl, (3,5-dichloropyridin-2-yl) methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophene-2-yl, 5-ethylthiophene-2-yl, 5 -Chlorothiophen-2-yl, 5-bromothiophen-2-yl, 4-methylthiophene-2-yl, 3-methylthiophene-2-yl, 5-fluorothiophene-3-yl, 3,5-dimethylthiophene-2-yl, 3 -Ethylthiophen-2-yl, 4,5-dimethylthiophen-2-yl, 3,4-dimethylthiophen-2-yl, 4-chlorothiophen-2-yl, furan-2-yl, 5-methyl-furan-2-yl, 5 Ethyl-furan-2-yl, 5-methoxycarbonyl-furan-2-yl, 5- Chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, Tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 2-phenyleth-1-yl, 1- (4-methylphenyl) eth-1-yl, 1- (3-methylphenyl) eth-1-yl, 1- (2 Methylphenyl) eth-1-yl, 1- (4-chlorophenyl) eth-1-yl, 1- (3-chlorophenyl) eth-1-yl, 1- (2-chlorophenyl) eth-1-yl, 1 - (4-trifluoromethylphenyl) eth-1-yl, 1- (3-trifluoromethyl-phenyl) -eth-1-yl,
1- (2-Trifluormethylphenyl)eth-l-yl, l-(4-Fluorphenyl)eth-l-yl, l-(3-Fluorphenyl)eth-l-yl, l-(2- Fluorphenyl)eth-l-yl, l-(4-Cyanophenyl)eth-l-yl, l-(3-Cyanophenyl)eth-l-yl, l-(2- Cyanophenyl)eth-l-yl, 2-(3-Fluorphenyl)eth-l-yl, 2-(4-Fluorphenyl)eth-l-yl, 2-(2- Fluorphenyl)eth-l-yl, 2-(2-Chlorphenyl)eth-l -yl, 2-(3-Chlorphenyl)eth-l-yl, 2-(4- Chlorphenyl)eth-l-yl, 2-(2-Bromphenyl)eth-l-yl, 2-(3-Bromphenyl)eth-l-yl, 2-(4- Bromphenyl)eth-l-yl, 2-(2-Cyanophenyl)eth-l-yl, 2-(3-Cyanophenyl)eth-l-yl, 2-(4- Cyanophenyl)eth- 1 -yl, 2-(2-Trifluormethylphenyl)eth- 1 -yl, 2-(3 -Trifluormethylphenyl)eth- 1 -yl,1- (2-trifluoromethylphenyl) eth-1-yl, 1- (4-fluorophenyl) eth-1-yl, 1- (3-fluorophenyl) eth-1-yl, 1- (2-fluorophenyl) eth-1 yl, 1- (4-cyanophenyl) eth-1-yl, 1- (3-cyanophenyl) eth-1-yl, 1- (2-cyanophenyl) eth-1-yl, 2- (3-fluorophenyl) ethane 1-yl, 2- (4-fluorophenyl) eth-1-yl, 2- (2-fluorophenyl) eth-1-yl, 2- (2-chlorophenyl) eth-1-yl, 2- (3-chlorophenyl) eth-1-yl, 2- (4-chlorophenyl) eth-1-yl, 2- (2-bromophenyl) eth-1-yl, 2- (3-bromophenyl) eth-1-yl, 2- (4- Bromophenyl) eth-1-yl, 2- (2-cyanophenyl) eth-1-yl, 2- (3-cyanophenyl) eth-1-yl, 2- (4-cyanophenyl) eth-1-yl, 2 ( 2-trifluoromethylphenyl) eth-1-yl, 2- (3-trifluoromethyl-phenyl) -eth-1-yl,
2- (4-Trifluormethylphenyl)eth- 1 -yl, 2-(2-Methoxyphenyl)eth- 1 -yl, 2-(3 -Methoxyphenyl)eth- 1 - yl, 2-(4-Methoxyphenyl)eth-l-yl, 2-(4-Methylphenyl)eth-l-yl, 2-(2-Methylphenyl)eth-l-yl, Benzyl, (4-Fluorphenyl)methyl, (3-Fluorphenyl)methyl, (2-Fluorphenyl)methyl, (2,4- Difluorphenyl)methyl, (3,5-Difluorphenyl)methyl, (2,5-Difluorphenyl)methyl, (2,6- Difluorphenyl)methyl, (2,4,5-Trifluorphenyl)methyl, (2,4,6-Trifluorphenyl)methyl, (4- Chlorphenyl)methyl, (3-Chlorphenyl)methyl, (2-Chlorphenyl)methyl, (2,4- Dichlorphenyl)methyl, (3,5-Dichlorphenyl)methyl, (2,5-Dichlorphenyl)methyl, (2,6- Dichlorphenyl)methyl, (2,4,5-Trichlorphenyl)methyl, (2,4,6-Trichlorphenyl)methyl, (4- Bromphenyl)methyl, (3-Bromphenyl)methyl, (2-Bromphenyl)methyl, (4-Iodphenyl)methyl, (3- Iodphenyl)methyl, (2-Iodphenyl)methyl, (3-Chlor-5-Trifluormethyl-pyridin-2-yl)methyl, (2- Brom-4-Fluorphenl)methyl, (2-Brom-4-Chlorphenyl)methyl, (3-Brom-4-Fluorphenyl)methyl, (3-Brom-4-Chlorphenyl)methyl, (3-Brom-5-Fluorphenyl)methyl, (3-Brom-5- Chlorphenyl)methyl, (2-Fluor-4-Bromphenyl)methyl, (2-Chlor-4-Bromphenyl)methyl, (3-Fluor- 4-Bromphenyl)methyl, (3-Chlor-4-Bromphenyl)methyl, (2-Chlor-4-Fluorphenyl)methyl, (3- Chlor-4-Fluorphenyl)methyl, (2-Fluor-3 -Chlorphenyl)methyl, (2-Fluor-4-Chlorphenyl)methyl, (2-Fluor-5-Chlorphenyl)methyl, (3-Fluor-4-Chlorphenyl)methyl, (3-Fluor-5- Chlorphenyl)methyl, (2-Fluor-6-Chlorphenyl)methyl, 1-Phenyleth-l-yl, 3,5-Dfluorpyridin-2-yl, (3 ,6-Dichlor-pyridin-2-yl)methyl, (4-Trifluormethylphenyl)methyl, (3 - Trifluormethylphenyl)methyl, (2-Trifluormethylphenyl)methyl, (4-Ethylphenyl)methyl, (3- Ethylphenyl)methyl, (2-Ethylphenyl)methyl, (4-Trifluormethoxyphenyl)methyl, (3- Trifluormethoxyphenyl)methyl, (2-Trifluormethoxyphenyl)methyl, (4-Methoxyphenyl)methyl, (3-Methoxyphenyl)methyl, (2-Methoxyphenyl)methyl, (4-Methylphenyl)methyl, (3- Methylphenyl)methyl, (2-Methylphenyl)methyl, (4-Cyanophenyl)methyl, (3- Cyanophenyl)methyl, (2-Cyanophenyl)methyl, (2,4-Diethylphenyl)methyl, (3,5- Diethylphenyl)methyl, (3,4-Dimethylphenyl)methyl, (3,5-Dimethoxyphenyl)methyl, 1- Phenyleth-l -yl, l -(2,4-Dichlorphenyl)eth-l -yl, 2-(5-Chlor-2-fluorphenyl)eth-l -yl, 2-(4-Chlor-2- fluorphenyl)eth-l -yl, 2-(2-Chlor-4-fluorphenyl)eth-l -yl, 2-(2-Chlor-5-fluorphenyl)eth-l -yl, 2- (3-Chlor-2-fluorphenyl)eth-l -yl, 2-(3-Chlor-4-fluorphenyl)eth-l -yl, 2-(3-Chlor-5- fluorphenyl)eth-l -yl, 2-(4-Chlor-3-fluorphenyl)eth-l -yl, 2-(2-Chlor-6-fluorphenyl)eth-l -yl, 1 ,3- Thiazol-2-yl, 4-Methyl-l ,3-thiazol-2-yl, l ,3-Thiazol-2-yl, 1 -Methyl-imidazol-4-yl, 1 -Methyl- imidazol-5-yl, 1 -Ethyl-imidazol-4-yl, l -Ethyl-imidazol-5-yl, 1 -iso-Propyl-imidazol-4-yl, 1 -iso- Propyl-imidazol-5-yl, 4-(Methylcarbonylamino)phenylmethyl, 4-(iso- Propylcarbonylamino)phenylmethyl,4-(cyclo-Propylamino)phenylmethyl, 2-(2,6- Difluorphenyl)eth-l -yl, 2-(2,5-Difluorphenyl)eth-l -yl , 2-(2,4-Difluorphenyl)eth-l -yl, 2-(2,6- Dichlorphenyl)eth-l -yl, 2-(2,5-Dichlorphenyl)eth-l -yl , 2-(2,4-Dichlorphenyl)eth-l -yl, 2-(2,3-2- (4-trifluoromethylphenyl) eth-1-yl, 2- (2-methoxyphenyl) eth-1-yl, 2- (3-methoxyphenyl) eth-1-yl, 2- (4-methoxyphenyl) eth-1-yl yl, 2- (4-methylphenyl) eth-1-yl, 2- (2-methylphenyl) eth-1-yl, benzyl, (4-fluorophenyl) methyl, (3-fluorophenyl) methyl, (2-fluorophenyl) methyl , (2,4-Difluorophenyl) methyl, (3,5-difluorophenyl) methyl, (2,5-difluorophenyl) methyl, (2,6-difluorophenyl) methyl, (2,4,5-trifluorophenyl) methyl, (2 , 4,6-trifluorophenyl) methyl, (4-chlorophenyl) methyl, (3-chlorophenyl) methyl, (2-chlorophenyl) methyl, (2,4-dichlorophenyl) methyl, (3,5-dichlorophenyl) methyl, (2 , 5-dichlorophenyl) methyl, (2,6-dichlorophenyl) methyl, (2,4,5-trichlorophenyl) methyl, (2,4,6-trichlorophenyl) methyl, (4-bromophenyl) methyl, (3-bromophenyl) methyl, (2-bromophenyl) methyl, (4-iodophenyl) methyl, (3-iodophenyl) methyl, (2-iodophenyl) methyl, (3-chloro-5-trifluoromethylpyridin-2-yl) methyl, (2- Bromo-4-fluorophenol) methyl, (2-bromo-4-chlorophenyl) methyl, (3-bromo-4-fluorophenyl) methyl, (3-bromo-4-chlorophenyl) methyl, (3-bromo-5-fluorophenyl) methyl 1, (3-bromo-5-chlorophenyl) methyl, (2-fluoro-4-bromophenyl) methyl, (2-chloro-4-bromophenyl) methyl, (3-fluoro-4-bromophenyl) methyl, (3-chloro 4-bromophenyl) methyl, (2-chloro-4-fluorophenyl) methyl, (3-chloro-4-fluorophenyl) methyl, (2-fluoro-3-chlorophenyl) methyl, (2-fluoro-4-chlorophenyl) methyl , (2-fluoro-5-chlorophenyl) methyl, (3-fluoro-4-chlorophenyl) methyl, (3-fluoro-5-chlorophenyl) methyl, (2-fluoro-6-chlorophenyl) methyl, 1-phenyleth-1 -yl, 3,5-Dfluoropyridin-2-yl, (3, 6-dichloropyridin-2-yl) methyl, (4-trifluoromethylphenyl) methyl, (3-trifluoromethylphenyl) methyl, (2-trifluoromethylphenyl) methyl, ( 4-ethylphenyl) methyl, (3-ethylphenyl) methyl, (2-ethylphenyl) methyl, (4-trifluoromethoxyphenyl) methyl, (3-trifluoromethoxyphenyl) methyl, (2-trifluoromethoxyphenyl) methyl, (4-methoxyphenyl) methyl, (3 -Methoxyphenyl) methyl, (2-methoxyphenyl) methyl, (4-methylphenyl) methyl, (3-methylphenyl) methyl, (2-methylphenyl) methyl, (4-cyanophenyl) methyl, (3-cyanophenyl) methyl, (2- Cyanophenyl) methyl, (2,4-diethylphenyl) methyl, (3,5 - diethylphenyl) methyl, (3,4-dimethylphenyl) methyl, (3,5-dimethoxyphenyl) methyl, 1- Phenyleth-1-yl, 1- (2,4-dichlorophenyl) eth-1-yl, 2- (5-chloro-2-fluorophenyl) eth-1-yl, 2- (4-chloro-2-fluorophenyl) eth -l -yl, 2- (2-chloro-4-fluorophenyl) eth-1-yl, 2- (2-chloro-5-fluorophenyl) eth-1-yl, 2- (3-chloro-2-fluorophenyl) eth-1-yl, 2- (3-chloro-4-fluorophenyl) eth-1-yl, 2- (3-chloro-5-fluorophenyl) eth-1-yl, 2- (4-chloro-3-fluorophenyl ) eth-1-yl, 2- (2-chloro-6-fluorophenyl) eth-1-yl, 1, 3-thiazol-2-yl, 4-methyl-1,3-thiazol-2-yl, 3-Thiazol-2-yl, 1-methyl-imidazol-4-yl, 1-methyl-imidazol-5-yl, 1-ethyl-imidazol-4-yl, 1-ethyl-imidazol-5-yl, 1 - iso -propyl-imidazol-4-yl, 1-iso -propyl-imidazol-5-yl, 4- (methylcarbonylamino) phenylmethyl, 4- (iso -propylcarbonylamino) phenylmethyl, 4- (cyclopropylamino) phenylmethyl, 2- ( 2,6-difluorophenyl) eth-1-yl, 2- (2,5-difluorophenyl) eth-1-yl, 2- (2,4-difluorophenyl) eth-1-yl, 2- (2,6-dichlorophenyl ) eth-1-yl, 2- (2,5-dichlorophenyl) eth-1-yl, 2- (2,4-dichlorophenyl) eth-1-yl, 2- (2,3-
Dichlorphenyl)eth-l -yl, 2-(3,5-Dichlorphenyl)eth-l -yl, 2-(4-Nitrophenyl)eth-l -yl, 2-(2- Nitrophenyl)eth-l -yl steht. Dichlorophenyl) eth-1-yl, 2- (3,5-dichlorophenyl) eth-1-yl, 2- (4-nitrophenyl) eth-1-yl, 2- (2-nitrophenyl) eth-1-yl.
Die oben aufgeführten allgemeinen oder in Vorzugsbereichen aufgeführten Restedefinitionen gelten sowohl für die Endprodukte der Formel (I) als auch entsprechend für die jeweils zur Herstellung benötigten Ausgangs- oder Zwischenprodukte. Diese Restedefinitionen können untereinander, also auch zwischen den angegebenen bevorzugten Bereichen, beliebig kombiniert werden. The general or preferred radical definitions given above apply both to the end products of the formula (I) and correspondingly to the starting materials or intermediates required in each case for the preparation. These remainder definitions can be combined with one another as desired, ie also between the specified preferred ranges.
Vor allem aus den Gründen der erhöhten Stresstoleranz und/oder besseren Herstellbarkeit sind erfindungsgemäße Verbindungen der genannten Formel (I) oder deren Salze bzw. deren Above all, for reasons of increased stress tolerance and / or better manufacturability, compounds of the formula (I) according to the invention or their salts or their compounds
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. Use according to the invention of particular interest, in which individual radicals have one of the meanings already mentioned or mentioned below, 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: Sofern nicht anders definiert, gilt generell für die Bezeichnung von chemischen Gruppen, dass die Anbindung an das Gerüst bzw. den Rest des Moleküls über das zuletzt genannte Strukturelement der betreffenden chemischen Gruppe erfolgt, d.h. beispielsweise im Falle von (C2-Cg)-Alkenyloxy über das Sauerstoffatom, und im Falle von Heterocyclyl-(Ci-Cg)-alkyl oder R120(0)C-(Ci-Cg)-Alkyl jeweils über das C-Atom der Alkylgruppe. In einer zusammengesetzten chemischen Gruppe wie z. B. Heterocyclyl- (Ci-Cg)-alkyl oder R120(0)C-(Ci-Cg)-Alkyl steht die Bezeichnung "Alkyl" daher auch für eine Alkylengruppe. 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 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: Unless defined otherwise, the designation of chemical groups generally means that the attachment to the skeleton or the rest of the molecule takes place via the last-mentioned structural element of the relevant chemical group that is, for example, in the case of (C 2 -C 6) -alkenyloxy via the oxygen atom, and in the case of heterocyclyl (Ci-Cg) -alkyl or R 12 0 (0) C (Ci-Cg) -alkyl in each case via the C Atom of the alkyl group. In a composite chemical group such. B. Heterocyclyl- (Ci-Cg) -alkyl or R 12 0 (0) C- (Ci-Cg) -alkyl, the term "alkyl" is therefore also an alkylene group. According to the invention "alkylsulfonyl" - alone or as part of a chemical group - is 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, 1,1-Dimethylethylsulfonyl, Pentylsulfonyl, 1 -Methylbutylsulfonyl, 2-Methylbutyl- sulfonyl, 3 -Methylbutylsulfonyl, 1,1-Dimethylpropylsulfonyl, 1 ,2-Dimethylpropylsulfonyl, 2,2-Di- methylpropylsulfonyl, 1 -Ethylpropylsulfonyl, Hexylsulfonyl, 1 -Methylpentylsulfonyl, 2-Methyl- pentylsulfonyl, 3 -Methylpentylsulfonyl, 4-Methylpentylsulfonyl, 1,1 -Dimethylbutylsulfonyl, 1,2-Di- methylbutylsulfonyl, 1 ,3 -Dimethylbutylsulfonyl, 2,2-Dimethylbutylsulfonyl, 2,3-Dimethylbutylsulfonyl, 3, 3 -Dimethylbutylsulfonyl, 1 -Ethylbutylsulfonyl, 2-Ethylbutylsulfonyl, 1,1,2-Trimethylpropylsulfonyl, 1 ,2,2-Trimethylpropylsulfonyl, 1 -Ethyl- 1 -methylpropylsulfonyl und 1 -Ethyl-2-methylpropylsulfonyl. Carbon atoms, e.g. (but not limited to) (C 1 -C 6) alkylsulfonyl such as methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methyl-propylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 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" is 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, Iod, Cyano, Nitro, Alkyl-, Haloalkyl-, Haloalkoxy-, Amino-, Alkylamino-, Alkylcarbonylamino-, Dialkylamino- oder Alkoxygruppen. Heteroarylsulfonyl, here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
Erfindungsgemäß steht "Alkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Alkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 According to the invention "alkylthio" - alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cio)-, (CI-CÖ)- oder (Ci-C4)-Alkylthio, z.B. (aber nicht beschränkt auf) (Ci- Ce)-Alkylthio wie 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, 2,2-Dimethylpropylthio, 1- Ethylpropylthio, Hexylthio, 1 -Methylpentylthio, 2-Methylpentylthio, 3-Methylpentylthio, 4-Methyl- pentylthio, 1,1-Dimethylbutylthio, 1 ,2-Dimethylbutylthio, 1,3-Dimethylbutylthio, 2,2-Dimethylbutyl- thio, 2,3-Dimethylbutylthio, 3,3-Dimethylbutylthio, 1 -Ethylbutylthio, 2-Ethylbutylthio, 1,1,2-Tri- methylpropylthio, 1 ,2,2-Trimethylpropylthio, 1 -Ethyl- 1 -methylpropylthio und 1 -Ethyl-2-methyl- propylthio.  Carbon atoms, such as (Ci-Cio) -, (CI-CÖ) - or (Ci-C4) -alkylthio, e.g. (but not limited to) (ci-Ce) 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, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1- Dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-triethiol methylpropylthio, 1, 2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio.
„Alkenylthio" bedeutet erfindungsgemäßt ein über ein Schwefelatom gebundenen Alkenylrest, "Alkenylthio" in the invention means an alkenyl radical bonded via a sulfur atom,
Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Alkynylthio represents an alkynyl group bonded through a sulfur atom, cycloalkylthio represents a cycloalkyl group bonded through a sulfur atom, and cycloalkenylthio represents an above
Schwefelatom gebundenen Cycloalkenylrest. Sulfur atom bonded cycloalkenyl radical.
„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 (C1-C4)- Alkylsulfinyl, z. B. (aber nicht beschränkt auf) (Ci-C6)-Alkylsulfmyl wie Methylsulfinyl, Ethylsulfinyl, Propylsulfinyl, 1 -Methylethylsulfinyl, Butylsulfinyl, 1 -Methylpropylsulfinyl, 2-Methylpropylsulfinyl, 1 , 1 -Dimethylethylsulfinyl, Pentylsulfinyl, 1 -Methylbutylsulfinyl, 2-Methylbutylsulfinyl, 3- Methylbutylsulfinyl, 1 ,1 -Dimethylpropylsulfinyl, 1 ,2-Dimethylpropylsulfinyl, 2,2-Di- methylpropylsulfinyl, 1 -Ethylpropylsulfinyl, Hexylsulfinyl, 1 -Methylpentylsulfinyl, 2-Methylpentyl- sulfinyl, 3 -Methylpentylsulfinyl, 4-Methylpentylsulfinyl, 1 ,1 -Dimethylbutylsulfinyl, 1 ,2-Dimethyl- butylsulfinyl, 1 ,3-Dimethylbutylsulfinyl, 2,2-Dimethylbutylsulfinyl, 2,3-Dimethylbutylsulfinyl, 3,3- Dimethylbutylsulfinyl, 1 -Ethylbutylsulfinyl, 2-Ethylbutylsulfinyl, 1 ,1 ,2-Trimethylpropylsulfinyl, 1 ,2,2- Trimethylpropylsulfinyl, 1 -Ethyl-l -methylpropylsulfinyl und 1 -Ethyl-2-methylpropylsulfinyl. "Alkylsulfinyl (alkyl-S (= 0) -)", unless otherwise defined elsewhere, according to the invention for alkyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 1 -C 10) -, ( CI-CÖ) - or (C1-C4) - Alkylsulfinyl, e.g. (But not limited to) (C 1 -C 6) alkylsulfmyl such as methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2 Methylbutylsulfinyl, 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1, 1, 2-trimethylpropylsulfinyl, 1, 2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.
Analog sind„Alkenylsulfinyl" und„Alkinylsulfinyl", erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfmyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfmyl. Analog sind„Alkenylsulfonyl" und„Alkinylsulfonyl" erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über -S(=0)2- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkenylsulfonyl bzw. (C3-C10)-, (C3-C6)- oder (C3-C4)-Alkinylsulfonyl. Analogously, "alkenylsulfinyl" and "alkynylsulfinyl" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= O) -, such as (C 2 -C 10) -, (C 2 -C 6) - or ( C2-C4) - alkenylsulfmyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfmyl. Analogously, "alkenylsulfonyl" and "alkynylsulfonyl" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via -S (= O) 2-, such as (C 2 -C 10) -, (C 2 -C 6) - or ( C2-C4) - alkenylsulfonyl or (C3-C10) -, (C3-C6) - or (C3-C4) -alkynylsulfonyl.
„Alkoxy" bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, z. B. (aber nicht beschränkt auf) (Ci-Ce)-Alkoxy wie Methoxy, Ethoxy, Propoxy, 1 -Methylethoxy, Butoxy, 1 -Methylpropoxy, 2-"Alkoxy" means an alkyl radical attached 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-alkoxy.
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-Di- methylbutoxy, 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-l -methylpropoxy 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)-Alkmoxy. „Cycloalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest. 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-1-methylpropoxy and 1-ethyl-2-methylpropoxy. Alkenyloxy a bonded via an oxygen atom alkenyl group, an alkynyloxy bonded via an oxygen atom alkynyl group such as (C 2 -C 1 0) -, (C 2 -C 6) - or (C 2 -C 4) alkenoxy or (C3 C10) -, (C 3 -C 6) - or (C 3 -C 4) -Alkmoxy. "Cycloalkyloxy" means a cycloalkyl radical bonded via an oxygen atom, and cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
„Alkylcarbonyl" (Alkyl-C(=0)-), soweit nicht an anderer Stelle anders definiert, steht erfindungsgemäß für Alkylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (Ci-Ce)- oder (C1-C4)- Alkylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der "Alkylcarbonyl" (alkyl-C (= O) -), unless otherwise defined elsewhere, is according to the invention alkyl radicals which are bonded to the skeleton via -C (= O) -, such as (C 1 -C 10) -, (Ci-Ce) - or (C1-C4) - alkylcarbonyl The number of carbon atoms refers to the alkyl radical in the
Alkylcarbonylgruppe. Analog stehen„Alkenylcarbonyl" und„Alkinylcarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyl bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)- Alkinylcarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonylgruppe. Alkylcarbonyl. Analogously, "alkenylcarbonyl" and "alkynylcarbonyl" are, unless otherwise defined elsewhere, according to the invention for alkenyl or alkynyl radicals which are bonded to the skeleton via -C (= O) -, such as (C 2 -C 10) -, ( C 2 -C 6) - or (C 2 -C 4) -alkenylcarbonyl or (C 2 -C 10) -, (C 2 -C 6) - or (C 2 -C 4) -alkynylcarbonyl. The number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
„Alkoxycarbonyl (Alkyl-0-C(=0)-)", soweit nicht an anderer Stelle anders definiert: Alkylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C1-C10)-, (CI-CÖ)- oder (Ci-C4)-Alkoxycarbonyl. Die Anzahl der C-Atome bezieht sich dabei auf den Alkylrest in der Alkoxycarbonylgruppe. Analog stehen „Alkenyloxycarbonyl" und„Alkinyloxycarbonyl", soweit nicht an anderer Stelle anders definiert, erfindungsgemäß für Alkenyl- bzw. Alkinylreste, die über -0-C(=0)- an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenyloxycarbonyl bzw. (C3-C10)-, (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 radicals attached to the skeleton via -0-C (= 0) - such as (C1-C10) - , (CI-CÖ) - or (C 1 -C 4) -alkoxycarbonyl The number of C atoms here refers to the alkyl radical in the alkoxycarbonyl group, analogously "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 (= O), such as (C 2 -C 10) -, (C 2 -C 6 ) - or (C 2 -C 4 ) - alkenyloxycarbonyl or (C3-C10) -, (C 3 -C 6) - or (C3-C4) - alkynyloxycarbonyl the number of carbon atoms refers to the alkenyl and alkynyl group in the alkynyloxycarbonyl group or alkene. ,
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) -O-) is according to the invention, unless otherwise defined elsewhere, for alkyl radicals which have a carbonyloxy group (-C (= O) -O-) with the oxygen the skeleton are bonded, such as (C 1 -C 10) -, (C 1 -C 6) - or (C 1 -C 4) -alkylcarbonyloxy The number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
Analog sind„Alkenylcarbonyloxy" und„Alkinylcarbonyloxy" erfindungsgemäß definiert als Alkenyl- bzw. Alkinylreste, die über (-C(=0)-0-) mit dem Sauerstoff an das Gerüst gebunden sind, wie (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkenylcarbonyloxy bzw. (C2-C10)-, (C2-C6)- oder (C2-C4)-Alkinylcarbonyloxy. Die Anzahl der C-Atome bezieht sich dabei auf den Alkenyl- bzw. Alkinylrest in der Alkenyl- bzw. Alkinylcarbonyloxygruppe. Analogously, "alkenylcarbonyloxy" and "alkynylcarbonyloxy" are defined according to the invention as alkenyl or alkynyl radicals which are bonded to the skeleton via (-C (= O) -O-), such as (C 2 -C 10) -, (C 2 -C 4) -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.
In Kurzformen wie z.B. C(0)R12, C(0)OR12, OC(O)NR10Ru, oder C(O)NR10Ru steht die in Klammern aufgeführte Kurzform O für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes Sauerstoffatom. In short forms such as, for example, C (O) R 12 , C (O) OR 12 , OC (O) NR 10 R u , or C (O) NR 10 R u , the short form O shown in parentheses represents a double bond to the adjacent carbon atom bound oxygen atom.
In Kurzformen wie z.B. OC(S)OR12, OC(S)SR13, OC(S)NR10RU, steht die in Klammern aufgeführte Kurzform S für ein über eine Doppelbindung an das benachbarte Kohlenstoffatom gebundenes In short forms such as, for example, OC (S) OR 12 , OC (S) SR 13 , OC (S) NR 10 R U , the abbreviation S shown in parentheses S stands for a double bond bound to the adjacent carbon atom
Schwefelatom. 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. Vom Begriff„gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist. Von der Systematik her ist„Aryl" in der Regel auch von dem Begriff „gegebenenfalls substituiertes Phenyl" umfasst. Bevorzugte Aryl-Substituenten sind hier zum Beispiel Wasserstoff, Halogen, Alkyl, Cycloalkyl, Cycloalkylalkyl, Cycloalkenyl, Halocycloalkyl, Alkenyl, Alkinyl, Aryl, Arylalkyl, Arylalkenyl, Heteroaryl, Heteroarylalkyl, Heterocyclyl, Heterocyclylalkyl, Alkoxyalkyl, Alkylthio, Haloalkylthio, Haloalkyl, Alkoxy, Haloalkoxy, Cycloalkoxy, Cycloalkylalkoxy, Aryloxy, Heteroraryloxy, Alkoxyalkoxy, Alkinylalkoxy, Alkenyloxy, Bis-alkylaminoalkoxy, Tris- [alkyl] silyl, Bis- [alkyl] arylsilyl, Bis- [alkyl] alkylsilyl, Tris- [alkyl] silylalkinyl, Arylalkinyl, Sulfur atom. The term "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. The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, the binding site being on the aromatic system. "Aryl" is also generally known from the term "optionally Preferred aryl substituents here are, for example, hydrogen, halogen, alkyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, halocycloalkyl, alkenyl, alkynyl, aryl, arylalkyl, arylalkenyl, heteroaryl, heteroarylalkyl, heterocyclyl, heterocyclylalkyl, alkoxyalkyl, alkylthio, haloalkylthio , Haloalkyl, alkoxy, haloalkoxy, cycloalkoxy, cycloalkylalkoxy, aryloxy, heteroaryloxy, alkoxyalkoxy, alkynylalkoxy, alkenyloxy, bis-alkylaminoalkoxy, tris [alkyl] silyl, bis [alkyl] arylsilyl, bis [alkyl] alkylsilyl, tris [alkyl ] silylalkynyl, arylalkynyl,
Heteroarylalkinyl, Alkylalkinyl, Cycloalkylalkinyl, Haloalkylalkinyl, Heterocyclyl-N-alkoxy, Nitro, Cyano, Amino, Alkylamino, Bis-alkylamino, Alkylcarbonylamino, Cycloalkylcarbonylamino,  Heteroarylalkynyl, alkylalkynyl, cycloalkylalkynyl, haloalkylalkynyl, heterocyclyl-N-alkoxy, nitro, cyano, amino, alkylamino, bis-alkylamino, alkylcarbonylamino, cycloalkylcarbonylamino,
Arylcarbonylamino, Alkoxycarbonylamino, Alkoxycarbonylalkylamino, Arylcarbonylamino, alkoxycarbonylamino, alkoxycarbonylalkylamino,
Arylalkoxycarbonylalkylamino, Hydroxycarbonyl, Alkoxycarbonyl, Aminocarbonyl, Arylalkoxycarbonylalkylamino, hydroxycarbonyl, alkoxycarbonyl, aminocarbonyl,
Alkylaminocarbonyl, Cycloalkylaminocarbonyl, Bis-Alkylaminocarbonyl, Heteroarylalkoxy, Alkylaminocarbonyl, cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
Arylalkoxy arylalkoxy
Ein heterocyclischer Rest (Heterocyclyl) enthält mindestens einen heterocyclischen Ring A heterocyclic radical (heterocyclyl) contains at least one heterocyclic ring
(=carbocyclischer Ring, in dem mindestens ein C-Atom durch ein Heteroatom ersetzt ist, vorzugsweise durch ein Heteroatom aus der Gruppe N, O, S, P) der gesättigt, ungesättigt, teilgesättigt oder heteroaromatisch ist und dabei unsubstituiert oder substituiert sein kann, wobei die Bindungsstelle an einem Ringatom lokalisiert ist. Ist der Heterocyclylrest oder der heterocyclische Ring gegebenenfalls substituiert, kann er mit anderen carbocyclischen oder heterocyclischen Ringen annelliert sein. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch mehrcyclische Systeme umfasst, wie beispielsweise 8-Aza-bicyclo[3.2.1]octanyl, 8-Aza-bicyclo[2.2.2]octanyl oder 1-Aza- bicyclo[2.2.1]heptyl. Im Falle von gegebenenfalls substituiertem Heterocyclyl werden auch (= carbocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P) which is saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom. When the heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings. In the case of optionally substituted heterocyclyl, polycyclic systems are also included, for example 8-azabicyclo [3.2.1] octanyl, 8-azabicyclo [2.2.2] octanyl or 1-azabicyclo [2.2.1] heptyl. In the case of optionally substituted heterocyclyl also become
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 spiro-cyclic systems such as 1-oxa-5-aza-spiro [2.3] hexyl. Unless defined otherwise, the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
Sauerstoffatome direkt benachbart sein sollen, wie beispielsweise mit einem Heteroatom aus der Gruppe N, O und S 1- oder 2- oder 3-Pyrrolidinyl, 3,4-Dihydro-2H-pyrrol-2- oder 3-yl, 2,3-Dihydro-lH-pyrrol- Oxygen atoms are to 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-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyridin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,4-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-pyrrol-1 - or 2- or 3-yl, 1- or 2- or 3- or 4-piperidinyl; 2,3,4,5-tetrahydropyridine-2- or 3- or 4- or 5-yl or 6-yl; 1,2,3,6-tetrahydropyridine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,2,3,4-tetrahydropyridine-1- or 2- or 3- or 4- or 5- or 6-yl; 1,4-dihydropyridine-I - 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-1- 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- 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- 2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 3,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 5,6-Dihydro-2H-azepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydro-3H-azepin-2- or 3- or 4- or 5- or 6-yl; 2,5-dihydropyridine-2- or 3- or 4- or 5- or 6-yl, 1- or 2- or 3- or 4-azepanyl; 2,3,4,5-tetrahydro-1H-azepine-1 or 2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,7-tetrahydro-1H-azepine-1 or 2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7-tetrahydro-1H-azepine-1 or 2 or 3 or 4-yl; 3,4,5,6-tetrahydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1H-azepine-1 or 2 or 3 or 4-yl; 2,5-dihydro-1H-azepine 1 or 2 or 3 or 4 or 5 or 6 or 7-yl; 2,7-dihydro-1H-azepine-1 or -2 or 3 or 4 yl; 2,3-dihydro-1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 3,4-dihydro-2H-azepine 2- or 3- or 4- or 5- or 6- or 7-yl; 3,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 5,6-dihydro-2H-azepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-3H-azepine
2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 1H-Azepin-1- 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- oder2- or 3- or 4- or 5- or 6- or 7-yl; 1H-azepine-1 or -2 or 3 or 4 or 5 or 6 or 7-yl; 2H-azepine-2- or 3- or 4- or 5- or 6- or 7-yl; 3H-azepine-2 or 3 or 4 or 5 or
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-Dihydrofüran-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrofüran-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; 2,3,4,5-6- or 7-yl; 4H-azepine-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- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2,3,4,7-Tetrahydrooxepin-2- oder 3- oderTetrahydrooxepine-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- 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- oder 4- oder 5- oder 6- oder 7-yl; 4,5-Dihydrooxepin-2- oder 3- oder 4-yl; 2,5-Dihydrooxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; Oxepin-2- oder 3- oder 4- oder 5- oder 6- oder 7-yl; 2- oder 3- Tetrahydrothiophenyl; 2,3-Dihydrothiophen-2- oder 3- oder 4- oder 5-yl; 2,5-Dihydrothiophen-2- oder 3-yl; Tetrahydro-2H-thiopyran-2- oder 3- oder 4-yl; 3,4-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder3- or 4- or 5- or 6- or 7-yl; 4,5-dihydrooxepin-2 or 3 or 4-yl; 2,5-dihydrooxepin-2 or 3 or 4 or 5 or 6 or 7-yl; Oxepin-2 or 3 or 4 or 5 or 6 or 7-yl; 2- or 3-tetrahydrothiophenyl; 2,3-dihydrothiophene-2 or 3 or 4 or 5-yl; 2,5-dihydrothiophene-2 or 3-yl; Tetrahydro-2H-thiopyran-2- or 3- or 4-yl; 3,4-dihydro-2H-thiopyran-2 or 3 or 4 or
5- oder 6-yl; 3,6-Dihydro-2H-thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 2H-Thiopyran-2- oder 3- oder 4- oder 5- oder 6-yl; 4H-Thiopyran-2- oder 3- oder 4-yl. Bevorzugte 3-Ring und 4-Ring- Heterocyclen sind beispielsweise 1- oder 2-Aziridinyl, Oxiranyl, Thiiranyl, 1- oder 2- oder 3-Azetidinyl, 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- oder 3- oder 4- oder 5-yl; 1- oder 2- oder 3- oder 4- Imidazolidinyl; 2,3-Dihydro-lH-imidazol-l- oder 2- oder 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-1- oder 2- oder 3- oder 4-yl; 1,2,3,4-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2,3, 6-Tetrahydropyridazin-l- oder 2- oder 3- oder 4- oder 5- oder5- 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-imidazol-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- or 2- or 3- or 4- or 5- or 6-yl; 1,2,3,6-tetrahydropyridazine-l- or 2- or 3- or 4- or 5- or
6- yl; 1,4,5, 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; 1,6-Dihydropyriazin-l- oder 3- oder 4- oder 5- oder 6-yl; 6-yl; 1,4,5,6-tetrahydropyridazine-1- or 3- or 4- or 5- or 6-yl; 3,4,5,6-tetrahydropyridazine-3- or 4- or 5-yl; 4,5-dihydropyridazine-3 or 4-yl; 3,4-dihydropyridazine-3- or 4- or 5- or 6-yl; 3,6-dihydropyridazine-3 or 4-yl; 1,6-dihydropyriazine-1- or 3- or 4- or 5- or 6-yl;
Hexahydropyrimidin-1- oder 2- oder 3- oder 4-yl; 1,4,5,6-Tetrahydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2,5,6-Tetrahydropyrimidin-l - oder 2- oder 4- oder 5- oder 6-yl; 1,2,3,4- Tetrahydropyrimidin-1- oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,6-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1,2-Dihydropyrimidin-l - oder 2- oder 4- oder 5- oder 6-yl; 2,5-Dihydropyrimidin-Hexahydropyrimidine-1 or 2 or 3 or 4-yl; 1,4,5,6-tetrahydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2,5,6-tetrahydropyrimidine-1 - or 2- or 4- or 5- or 6-yl; 1,2,3,4 Tetrahydropyrimidine-1 or 2 or 3 or 4 or 5 or 6-yl; 1,6-dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1,2-dihydropyrimidine-1 - 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; 1,4-Dihydropyrimidin-l- oder 2- oder 4- oder 5- oder 6-yl; 1- oder 2- oder 3-Piperazinyl; 1,2,3,6-Tetrahydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,2,3,4-Tetrahydropyrazin-l - oder 2- oder 3- oder 4- oder 5- oder 6-yl; 1,2-Dihydropyrazin-l- oder 2- oder 3- oder 5- oder 6-yl; 1,4-Dihydropyrazin-l - oder 2- oder 3-yl; 2,3-Dihydropyrazin-2- oder2- or 4- or 5-yl; 4,5-dihydropyrimidine-4- or 5- or 6-yl; 1,4-dihydropyrimidine-1- or 2- or 4- or 5- or 6-yl; 1- or 2- or 3-piperazinyl; 1,2,3,6-tetrahydropyrazine-1- or 2- or 3- or 5- or 6-yl; 1,2,3,4-tetrahydropyrazine-1 - or 2- or 3- or 4- or 5- or 6-yl; 1,2-dihydropyrazine 1- or 2- or 3- or 5- or 6-yl; 1,4-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; l,2-Dithiolan-3- oder 4-yl; 3H-l,2-Dithiol-3- oder 4- oder 5-yl; l,3-Dithiolan-2- oder 4-yl; 1,3-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-3- or 5- or 6-yl; 2,5-dihydropyrazine-2 or 3-yl; l, 3-dioxolane-2- or 4- or 5-yl; l, 3-dioxol-2 or 4-yl; 1, 3-dioxan-2 or 4 or 5-yl; 4H-l, 3-dioxin-2 or 4 or 5 or 6-yl; 1, 4-dioxane-2 or 3 or 5 or 6-yl; 2,3-dihydro-1,4-dioxin-2- or 3- or 5- or 6-yl; l, 4-dioxin-2 or 3-yl; l, 2-dithiolan-3 or 4-yl; 3H-1,2-dithiol-3- or 4- or 5-yl; l, 3-dithiolan-2 or 4-yl; 1,3-dithiol-2- or 4-yl; 1, 2-dithian-3 or 4-yl; 3,4-dihydro-1,2-dithiin-3 or 4 or 5 or 6-yl; 3,6-dihydro-
1.2- dithiin-3- oder 4-yl; l,2-Dithiin-3- oder 4-yl; l,3-Dithian-2- oder 4- oder 5-yl; 4H-l,3-Dithiin-2- oder 4- oder 5- oder 6-yl; Isoxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydroisoxazol-2- oder 3- oder1,2-dithiin-3 or 4-yl; l, 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; Isoxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydroisoxazole-2- or 3- or
4- oder 5-yl; 2,5-Dihydroisoxazol-2- oder 3- oder 4- oder 5-yl; 4,5-Dihydroisoxazol-3- oder 4- oder 5-yl; l,3-Oxazolidin-2- oder 3- oder 4- oder 5-yl; 2,3-Dihydro-l,3-oxazol-2- oder 3- oder 4- oder 5-yl; 2,5-4- or 5-yl; 2,5-dihydroisoxazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisoxazole-3 or 4 or 5-yl; l, 3-oxazolidine-2 or 3 or 4 or 5-yl; 2,3-dihydro-1,3-oxazol-2 or 3 or 4 or 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-Dihydro-1, 3-oxazol-2 or 4 or 5-yl; 4,5-dihydro-1,3-oxazol-2 or 4 or 5-yl; 1, 2-oxazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-1,2-oxazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-4H-1,2-oxazine-3 or 4 or 5 or 6-yl; 2H-l, 2-oxazine-2 or 3 or 4 or 5 or 6-yl; 6H-l, 2-oxazine-3 or 4 or 5 or 6-yl; 4H-1, 2-oxazine-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-1,3-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,3-oxazine-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- l,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-oxazine-2- or 4- or 5- or 6-yl; 5,6-dihydro-4H-1,3-oxazine-2- or 4- or 5- or 6-yl; 2H-, 3-oxazine-2- or 4- or 5- or 6-yl; 6H-1, 3-oxazine-2 or 4 or 5 or 6-yl; 4H-1, 3-oxazine-2 or 4 or 5 or 6-yl; Morpholine-2- or 3- or 4-yl; 3,4-dihydro-2H-1,4-oxazine-2- or 3- or 4- or 5- or 6-yl; 3,6-dihydro-2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 2H-1,4-oxazine-2- or 3- or 5- or 6-yl; 4H-1,4-oxazine-2 or 3-yl; 1, 2-oxazepan-2 or 3 or 4 or 5 or 6 or 7 yl; 2,3,4,5-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-1, 2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 2,3-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5-dihydro-1,2-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,2-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 4,5-dihydro-1, 2-oxazepine-3 or 4 or 5 or 6 or 7-yl; 4,7-dihydro-1,2-oxazepine-3 or 4 or 5 or 6 or 7-yl; 6,7-dihydro-1,2-oxazepine-3- or 4- or 5- or 6- or 7-yl; 1, 2-oxazepine-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-1, 3-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3,4,7-tetrahydro-l, 3-oxazepine-2 or 3-or 4- or 5- or 6- or 7-yl; 2,3,6,7-tetrahydro-1,3-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,5,6,7-tetrahydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-1, 3-oxazepine-2 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,3-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; 4,7-6- or 7-yl; 2,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 2,7-dihydro-1,3-oxazepine 2- or 4- or 5- or 6- or 7-yl; 4,5-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 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- oderDihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; 6,7-dihydro-1,3-oxazepine-2- or 4- or 5- or 6- or 7-yl; l, 3-oxazepine-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-1,4-oxazepine-2- or 3- or 4- or 5- or 6- or 7-yl; 2,3,4,7-tetrahydro-l, 4-oxazepine-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-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5,6,7-tetrahydro-l, 4-oxazepine-2 or 3 or 4 or 5 or 6 or 7-yl; 2,3-dihydro-1,4-oxazepine-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- 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- oder7- yl; 2,7-dihydro-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 4,5-dihydro-1,4-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-1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; 1,4-oxazepine-2- or 3- or 5- or 6- or 7-yl; Isothiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydroisothiazole-2 or 3 or 4 or 5 yl; 2,5-dihydroisothiazole-2 or 3 or 4 or 5-yl; 4,5-dihydroisothiazole-3 or 4 or 5-yl; 1,3-thiazolidine-2- or 3- or 4- or 5-yl; 2,3-dihydro-1,3-thiazole-2 or 3 or 4 or 5-yl; 2,5-dihydro-1,3-thiazol-2 or 4 or 5-yl; 4,5-dihydro-1,3-thiazol-2 or 4 or 5-yl; l, 3-thiazinan-2 or 3 or 4 or 5 or 6-yl; 3,4-dihydro-2H-1, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 3,6-dihydro-2H-l, 3-thiazine-2 or 3 or 4 or 5 or 6-yl; 5,6-dihydro-2H-l, 3-thiazine-2 or 4 or
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: 5- or 6-yl; 5,6-dihydro-4H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 2H-1, 3-thiazine-2 or 4 or 5 or 6-yl; 6H-l, 3-thiazine-2 or 4 or 5 or 6-yl; 4H-l, 3-thiazine-2 or 4 or 5 or 6-yl. Further examples of "heterocyclyl" are a partially or fully hydrogenated heterocyclic radical having 3 heteroatoms from the group N, O and S, such as, for example, l, 4,2-dioxazolidin-2 or 3 or 5-yl; l, 4,2-dioxazol-3 or 5-yl; 1,2,2-dioxazinane-2- or -3- or 5- or 6-yl; 5,6-dihydro-l, 4,2-dioxazine-3 or 5 or 6-yl; l, 4,2-dioxazine-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-dioxazepine-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-1, 4,2-dioxazepine-2 or 3 or 5 or 6 or 7-yl; 5H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl; 7H-l, 4,2-dioxazepine-3 or 5 or 6 or 7-yl. Structural examples of optionally further substituted heterocycles are also listed below:
Figure imgf000047_0001
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Figure imgf000047_0001
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Figure imgf000048_0001
Figure imgf000049_0001
Die oben aufgeführten Heterocyclen sind bevorzugt beispielsweise durch Wasserstoff, Halogen, Alkyl, Haloalkyl, Hydroxy, Alkoxy, Cycloalkoxy, Aryloxy, Alkoxyalkyl, Alkoxyalkoxy, Cycloalkyl,
Figure imgf000048_0001
Figure imgf000049_0001
The heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
Halocycloalkyl, Aryl, Arylalkyl, Heteroaryl, Heterocyclyl, Alkenyl, Alkylcarbonyl, Cycloalkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, Alkoxycarbonyl, Hydroxycarbonyl, Cycloalkoxycarbonyl, Halocycloalkyl, aryl, arylalkyl, heteroaryl, heterocyclyl, alkenyl, alkylcarbonyl, cycloalkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, alkoxycarbonyl, hydroxycarbonyl, cycloalkoxycarbonyl,
Cycloalkylalkoxycarbonyl, Alkoxycarbonylalkyl, Arylalkoxycarbonyl, Arylalkoxycarbonylalkyl, Alkinyl, Alkinylalkyl, Alkylalkinyl, Tris-alkylsilylalkinyl, Nitro, Amino, Cyano, Haloalkoxy, Cycloalkylalkoxycarbonyl, alkoxycarbonylalkyl, arylalkoxycarbonyl, arylalkoxycarbonylalkyl, alkynyl, alkynylalkyl, alkylalkynyl, trisalkylsilylalkynyl, 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, bisalkylamino, alkylamino, cycloalkylamino, hydroxycarbonylalkylamino, alkoxycarbonylalkylamino, arylalkoxycarbonylalkylamino, alkoxycarbonylalkyl (alkyl) amino, aminocarbonyl,
Alkylaminocarbonyl, Bis-alkylaminocarbonyl, Cycloalkylaminocarbonyl, Alkylaminocarbonyl, bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
Hydroxycarbonylalkylaminocarbonyl, Alkoxycarbonylalkylaminocarbonyl, Hydroxycarbonylalkylaminocarbonyl, alkoxycarbonylalkylaminocarbonyl,
Arylalkoxycarbonylalkylaminocarbonyl substituiert. 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. Arylalkoxycarbonylalkylaminocarbonyl substituted. If a main body is "substituted by one or more radicals" from an enumeration of radicals (= group) or a generically defined group of radicals, this includes the simultaneous substitution by a plurality of identical and / or structurally different radicals.
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 it is a partially or fully saturated nitrogen heterocycle, it may be linked to the rest of the molecule via both carbon and nitrogen.
Als Substituenten für einen substituierten heterocyclischen Rest kommen die weiter unten genannten Substituenten in Frage, zusätzlich auch Oxo und Thioxo. Die Oxogruppe als Substituent an einem Ring- C-Atom bedeutet dann beispielsweise eine Carbonylgruppe im heterocyclischen Ring. Dadurch sind vorzugsweise auch Lactone und Lactame umfasst. Die Oxogruppe kann auch an den Heteroringatomen, die in verschiedenen Oxidationsstufen existieren können, z.B. bei N und S, auftreten und bilden dann beispielsweise die divalenten Gruppen N(O) , S(O) (auch kurz SO) und S(0)2 (auch kurz SO2) im heterocyclischen Ring. Im Fall von -N(O)- und -S(0)-Gruppen sind jeweils beide Enantiomere umfasst. Suitable substituents for a substituted heterocyclic radical are the substituents mentioned below, in addition to oxo and thioxo. The oxo group as a substituent on a ring C atom then means, for example, a carbonyl group in the heterocyclic ring. As a result, lactones and lactams are preferably also included. The oxo group may also be attached to the hetero ring atoms, which may exist in different oxidation states, e.g. For example, at N and S, the divalent groups N (O), S (O) (also SO for short) and S (O) 2 (also SO2 for short) occur and form 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.
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- 3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, lH-Imidazol-l -yl; lH-Imidazol-2-yl; lH-Imidazol- 4-yl; lH-Imidazol-5-yl; lH-Pyrazol-l-yl; lH-Pyrazol-3-yl; lH-Pyrazol-4-yl; lH-Pyrazol-5-yl, 1H-1,2,3- 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, completely unsaturated aromatic heterocyclic compounds, preferably for 5- to 7-membered rings having 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-1-yl; lH-pyrrol-2-yl; 1H-pyrrol-3-yl; Furan-2-yl; Furan-3-yl; Thien-2-yl; Thien-3-yl, 1H-imidazol-1-yl; lH-imidazol-2-yl; 1H-imidazol-4-yl; lH-imidazol-5-yl; lH-pyrazol-l-yl; lH-pyrazol-3-yl; lH-pyrazol-4-yl; lH-pyrazol-5-yl, 1H-1,2,3-triazol-1-yl, 1H-l, 2,3-triazol-4-yl, 1H-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-1-yl, lH-l, 2,4-triazol-3-yl, 4H-l, 2,4-triazol-4-yl, l, 2,4-oxadiazole 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, pyrazine-2-yl, pyrazine-3-yl, pyrimidine-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 1,2,6-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 Heteroarylgrappen können femer 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, 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 1,2,6-oxazinyl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, 1,3-oxazole-2 -yl, 1,3-oxazol-4-yl, 1,3-oxazol-5-yl, isothiazol-3-yl, isothiazol-4-yl, isothiazol-5-yl, l, 3-thiazol-2-yl , 1, 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, 1H-l, 2,3,4-tetrazol-5-yl, l, 2,3,4-oxatriazol-5-yl, l, 2,3,4-thiatriazol-5-yl 1,2,3,5-Oxatriazol-4-yl, 1,2,3,5-thiatriazol-4-yl. The Heteroarylgrappen invention can be further substituted with one or more, identical or different radicals. Are two neighbors
Kohlenstoffatome Bestandteil eines weiteren aromatischen Rings, so handelt es sich um annellierte heteroaromatische Systeme, wie benzokondensierte oder mehrfach annellierte Heteroaromaten. Carbon atoms part of another aromatic ring, they are fused heteroaromatic systems, such as benzo-fused or multiply 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; 1,5-Naphthyridin; 1 ,6-Naphthyridin; 1 ,7-Naphthyridin; 1,8-Naphthyridin; 2,6- Naphthyridin; 2,7-Naphthyridin; Phthalazin; Pyridopyrazine; Pyridopyrimidine; Pyridopyridazine; Pteridine; Pyrimidopyrimidine. Beispiele für Heteroaryl sind auch 5- oder 6-gliedrige benzokondensierte Ringe aus der Gruppe lH-Indol-l-yl, lH-Indol-2-yl, lH-Indol-3-yl, lH-Indol-4-yl, lH-Indol-5-yl, 1H- Indol-6-yl, lH-Indol-7-yl, l-Benzofuran-2-yl, l-Benzofuran-3-yl, l-Benzofuran-4-yl, l-Benzofuran-5- yl, l-Benzofuran-6-yl, l-Benzofuran-7-yl, l-Benzothiophen-2-yl, l-Benzothiophen-3-yl, 1- Benzothiophen-4-yl, l-Benzothiophen-5-yl, l-Benzothiophen-6-yl, l-Benzothiophen-7-yl, lH-Indazol- 1-yl, lH-Indazol-3-yl, lH-Indazol-4-yl, lH-Indazol-5-yl, lH-Indazol-6-yl, lH-Indazol-7-yl, 2H-Indazol- 2-yl, 2H-Indazol-3-yl, 2H-Indazol-4-yl, 2H-Indazol-5-yl, 2H-Indazol-6-yl, 2H-Indazol-7-yl, 2H-Preferred are, 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-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl, isoquinolin-8-yl); quinoxaline; 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. Examples of heteroaryl are also 5- or 6-membered benzo-fused rings from the group 1H-indol-1-yl, 1H-indol-2-yl, 1H-indol-3-yl, 1H-indol-4-yl, 1H- 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-benzothiophene-2-yl, 1-benzothiophen-3-yl, 1-benzothiophene-4-yl, 1-benzothiophene-5 yl, 1-benzothiophene-6-yl, 1-benzothiophene-7-yl, 1H-indazol-1-yl, 1H-indazol-3-yl, 1H-indazol-4-yl, 1H-indazol-5-yl, 1H-indazol-6-yl, 1H-indazol-7-yl, 2H-indazol-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, 1 ,2-Benzisothiazol-7-yl. Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder Iod. Wird die 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, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl, l, 3 Benzoxazol-7-yl, 1,3-benzthiazol-2-yl, 1,3-benzthiazol-4-yl, 1,3-benzthiazol-5-yl, 1,3-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, 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. 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 Iodatom. Erfindungsgemäß bedeutet„Alkyl" einen geradkettigen oder verzweigten offenkettigen, gesättigten Kohlenwasserstoffrest, der gegebenenfalls ein- oder mehrfach substituiert ist und im letzteren Falle als „substituiertes Alkyl" bezeichnet wird. Bevorzugte Substituenten sind Halogenatome, Alkoxy-, Haloalkoxy-, Cyano-, Alkylthio, Haloalkylthio-, Amino- oder Nitrogruppen, besonders bevorzugt sind Methoxy, Methyl, Fluoralkyl, Cyano, Nitro, Fluor, Chlor, Brom oder Iod. Die Vorsilbe„Bis" schließt auch die Kombination unterschiedlicher Alkylreste ein, z. B. Methyl(Ethyl) oder Ethyl(Methyl). When used to denote a radical, then "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom. According to the invention, "alkyl" means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted 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, particularly preferred are methoxy, methyl, fluoroalkyl, cyano, nitro, fluorine, chlorine, bromine or iodine. The prefix "bis" also includes the combination of different alkyl radicals, for example, methyl (ethyl) or ethyl (methyl).
„Haloalkyl", ,,-alkenyl" und ,,-alkinyl" bedeuten durch gleiche oder verschiedene Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl "Haloalkyl", "-alkenyl" and "-alkynyl" mean by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
(= Monohalogenalkyl) wie z. B. CH2CH2C1, CH2CH2Br, CHC1CH3, CH2C1, CH2F; Perhaloalkyl wie z. B. CCI3, CC1F2, CFC12,CF2CC1F2, CF2CC1FCF3; Polyhaloalkyl wie z. B. CH2CHFC1, CF2CC1FH, CF2CBrFH, CH2CF3; Der Begriff Perhaloalkyl umfasst dabei auch den Begriff Perfluoralkyl. „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 (= Monohaloalkyl) such. CH 2 CH 2 Cl, CH 2 CH 2 Br, CHClCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such. B. CCl 3, CC1F 2, CFC1 2 CF 2 CC1F 2, CF 2 CC1FCF 3; Polyhaloalkyl such. CH 2 CHFC1, CF 2 CC1FH, CF 2 CBrFH, CH 2 CF 3; The term perhaloalkyl also encompasses the term perfluoroalkyl. "Partially fluorinated alkyl" means a straight-chain or branched, saturated hydrocarbon which is monosubstituted or polysubstituted by fluorine, it being possible for the corresponding fluorine atoms to be present as substituents on one or more different carbon atoms of the straight-chain or branched hydrocarbon chain, for example CHFCH3, CH 2 CH 2 F, CH 2 CH 2 CF 3, CHF 2, CH 2 F, CF 3 CHFCF 2
„Teilfluoriertes Haloalkyl" bedeutet einen geradkettigen oder verzweigten, gesättigten "Partially fluorinated haloalkyl" means a straight-chain or branched, saturated one
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. „Haloalkoxy" ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und 0CH2CH2C1; Entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste. Hydrocarbon which is substituted by various halogen atoms having at least one fluorine atom, wherein all other optional 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 complete substitution of halogen with the participation of at least one fluorine atom of the straight-chain or branched chain. "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, and the same applies to haloalkenyl and other radicals substituted by halogen.
Der hier beispielhaft genannte Ausdruck "(Ci-C4)-Alkyl" bedeutet eine Kurzschreibweise für geradkettiges oder verzweigtes Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der The term "(C 1 -C 4) -alkyl" given here by way of example denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
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 for C atoms, ie, includes the radicals methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals having a larger specified range of carbon atoms, eg. B. "(Ci-C6) -alkyl", accordingly also include straight-chain or branched alkyl radicals having a larger number of C atoms, ie, according to the example, the alkyl radicals having 5 and 6 C 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 1,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1 -Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred. Alkyl radicals, also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or
Dreifachbindung. Triple bond.
Der Begriff„Alkenyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige The term "alkenyl" in particular also includes straight-chain or branched open-chain
Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1,3-Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1,2-Propadienyl), 1 ,2-Butadienyl und 1,2,3-Pentatrienyl. Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert sein kann, z B. (aber nicht beschränkt auf) (C2-C6)- Alkenyl wie Ethenyl, 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, 1- Pentenyl, 2-Pentenyl, 3-Pentenyl, 4-Pentenyl, 1 -Methyl- 1 -butenyl, 2-Methyl-l -butenyl, 3 -Methyl- 1- butenyl, 1 -Methyl-2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3 -butenyl, 2-Methyl-3- butenyl, 3 -Methyl-3 -butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl- 1 -propenyl, 1 ,2-Dimethyl-2- propenyl, 1 -Ethyl- 1-propenyl, 1 -Ethyl-2-propenyl, 1-Hexenyl, 2-Hexenyl, 3-Hexenyl, 4-Hexenyl, 5- Hexenyl, 1 -Methyl- 1-pentenyl, 2-Methyl-l -pentenyl, 3-Methyl-l-pentenyl, 4-Methyl-l-pentenyl, 1- Methyl-2-pentenyl, 2-Methyl-2-pentenyl, 3-Methyl-2-pentenyl, 4-Methyl-2-pentenyl, l-Methyl-3- pentenyl, 2-Methyl-3 -pentenyl, 3 -Methyl-3 -pentenyl, 4-Methyl-3 -pentenyl, 1 -Methyl-4-pentenyl, 2- Methyl-4-pentenyl, 3-Methyl-4-pentenyl, 4-Methyl-4-pentenyl, 1 , 1 -Dimethyl-2-butenyl, 1 , 1 -Dimethyl- 3 -butenyl, 1 ,2-Dimethyl- 1 -butenyl, 1 ,2-Dimethyl-2-butenyl, 1 ,2-Dimethyl-3 -butenyl, 1,3-Dimethyl-l- butenyl, l,3-Dimethyl-2-butenyl, l,3-Dimethyl-3-butenyl, 2,2-Dimethyl-3 -butenyl, 2,3-Dimethyl-l- butenyl, 2,3-Dimethyl-2-butenyl, 2,3-Dimethyl-3-butenyl, 3,3-Dimethyl-l -butenyl, 3,3-Dimethyl-2- butenyl, l-Ethyl-l-butenyl, 1-Ethy 1-2 -butenyl, 1 -Ethyl- 3 -butenyl, 2-Ethyl-l -butenyl, 2-Ethyl-2-butenyl, 2-Ethyl-3 -butenyl, 1 , 1 ,2-Trimethyl-2-propenyl, 1 -Ethyl- 1 -methyl-2-propenyl, 1 -Ethyl-2-methyl- 1 - propenyl und 1 -Ethyl-2-methyl-2-propenyl. Hydrocarbon radicals 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 cumulated double bonds, such as allenyl (1,2-propadienyl), 1, 2-butadienyl and 1,2,3-pentatrienyl. Alkenyl means e.g. Vinyl, which may optionally be substituted by further alkyl radicals, for example (but not limited to) (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-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2 -Methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl 2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-penteny 1, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1, 1-dimethyl-2-butenyl, 1, 1-dimethyl-3-butenyl, 1, 2 Dimethyl 1-butenyl, 1, 2-dimethyl-2-butenyl, 1, 2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1, 3 Dimethyl 3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3- Dimethyl-1-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-1, 2 -butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2 Ethyl-2-butenyl, 2-ethyl-3-butenyl, 1, 1, 2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl.
Der Begriff„Alkinyl" schließt insbesondere auch geradkettige oder verzweigte offenkettige The term "alkynyl" in particular also includes straight-chain or branched open-chain
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1,3-Butatrienyl bzw. 3-Penten-l -in-l -yl. (C2-C6)-Alkinyl bedeutet z.B. Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, l-Methyl-2- butinyl, l-Methyl-3 -butinyl, 2-Methyl-3 -butinyl, 3 -Methyl- 1-butinyl, 1 , 1 -Dimethyl-2-propinyl, 1-Ethyl- 2-propinyl, 1-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- 1-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- 1-butinyl, 1 -Ethyl-2-butinyl, 1- Ethyl-3-butinyl, 2-Ethyl-3 -butinyl und 1-Ethyl- 1 -methyl-2-propinyl. Hydrocarbon radicals with more than one triple bond or with one or more Triple bonds and one or more double bonds, such as 1,3-butatrienyl and 3-penten-1-yn-1-yl, respectively. (C 2 -C 6) -Alkynyl means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-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-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-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3, 3-dimethyl-1-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 preferably having 3-8 ring C atoms, eg 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 are included with substituents, wherein substituents 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[1.1.0]butan-l-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-l -yl, Bicyclo [1.1.1 ]pentan-l - yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Bicyclo[2.1.1]hexyl, Bicyclo[2.2.1]hept-2-yl, Bicyclo[2.2.2]octan-2-yl, Bicyclo[3.2.1]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-Cv)-Cycloalkyl" bedeutet eine Kurzschreibweise für Cycloalkyl mit drei bis 7 Cycloalkyl, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [1.1.1] pentan-1-yl, bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.1.1] hexyl, bicyclo [2.2.1 ] hept-2-yl, bicyclo [2.2.2] octan-2-yl, bicyclo [3.2.1] octan-2-yl, bicyclo [3.2.2] nonan-2-yl, adamantan-1-yl and adamantane -2-yl, but also systems such. B. l, l-Bi (cyclopropyl) -l-yl, l, l'-Bi (cyclopropyl) -2-yl. The term "(C3-Cv) cycloalkyl" means a shorthand notation for cycloalkyl of three to seven
Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome. Carbon atoms corresponding to the range for C atoms.
Im 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, Spiro[3.3]hept-l-yl, Spiro[3.3]hept-2-yl. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-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.
„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, 1,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend. 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(C2H5)-C2H5. Cycloalkyliden bedeutet ein "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, substituents also having a double bond on the cycloalkenyl radical, eg an alkylidene group such as methylidene, being included In the case of optionally substituted cycloalkenyl, the explanations apply to substituted Corresponding to cycloalkyl. The term "alkylidene", for example also in the form of (C 1 -C 10) -alkylidene, means the radical of a straight-chain or branched open-chain hydrocarbon radical which is bonded via a double bond.As a binding site for alkylidene, only positions on the main body naturally occur Question in which two hydrogen atoms can be replaced by the double bond: radicals are eg = CH 2 , = CH-CH 3 , = C (CH 3 ) -CH 3 , = C (CH 3 ) -C 2 H 5 or = C (C 2 H 5 ) -C 2 H 5. Cycloalkylidene means
carbocyclischer Rest, der über eine Zweifachbindung gebunden ist. carbocyclic radical bonded via a double bond.
„Cycloalkylalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylalkylrest und „Arylalkyloxy" bedeutet ein über ein Sauerstoffatom gebundenen Arylalkylrest. "Cycloalkylalkyloxy" means a cycloalkylalkyl radical bonded via an oxygen atom, and "arylalkyloxy" means an arylalkyl radical bonded via an oxygen atom.
„Alkoxyalkyl" steht für einen über eine Alkylgruppe gebundenen Alkoxyrest und„Alkoxyalkoxy" bedeutet einen über ein Sauerstoffatom gebundenen Alkoxyalkylrest, z.B. (aber nicht beschränkt auf) Methoxymethoxy, Methoxyethoxy, Ethoxyethoxy, Methoxy-n-propyloxy. „Alkylthioalkyl" steht für einen über eine Alkylgruppe gebundenen Alkylthiorest und "Alkoxyalkyl" means an alkoxy group attached via an alkyl group, and "alkoxyalkoxy" means an alkoxyalkyl group bonded via an oxygen atom, e.g. (but not limited to) methoxymethoxy, methoxyethoxy, ethoxyethoxy, methoxy-n-propyloxy. "Alkylthioalkyl" means 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 bound via an alkyl group and
„Heteroaryloxyalkyl" bedeutet einen über eine Alkylgruppe gebundenen Heteroaryloxyrest. "Heteroaryloxyalkyl" means a heteroaryloxy group bonded via an alkyl group.
„Haloalkoxyalkyl" steht für einen gebundenen Haloalkoxyrest und„Haloalkylthioalkyl" bedeutet einen über eine Alkylgruppe gebundenen Haloalkylthiorest. "Haloalkoxyalkyl" means a haloalkoxy radical attached and "haloalkylthioalkyl" means a haloalkylthio radical attached 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" means an aryl group attached via an alkyl group, "heteroarylalkyl" means a heteroaryl group bonded via an alkyl group, and "heterocyclylalkyl" means a heterocyclyl group bonded through 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, 1 -Cyclopropylprop-l -yl, 3-Cyclopropylprop-l -yl. "Cycloalkylalkyl" means a cycloalkyl radical attached via an alkyl group, for example (but not limited to) cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, 1-cyclopropyleth-1-yl, 2-cyclopropyleth-1-yl, 1-cyclopropylpropyl l -yl, 3-cyclopropylprop-1-yl.
„Arylalkenyl" steht für einen über eine Alkenylgruppe gebundenen Arylrest,„Heteroarylalkenyl" bedeutet einen über eine Alkenylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkenyl" bedeutet einen über eine Alkenylgruppe gebundenen Heterocyclylrest. „Arylalkinyl" steht für einen über eine Alkinylgruppe gebundenen Arylrest,„Heteroarylalkinyl" bedeutet einen über eine Alkinylgruppe gebundenen Heteroarylrest, und„Heterocyclylalkinyl" bedeutet einen über eine Alkinylgruppe gebundenen Heterocyclylrest. Erfindungsgemäß steht "Haloalkylthio" - in Alleinstellung oder als Bestandteil einer chemischen Gruppe - für geradkettiges oder verzweigtes S-Halogenalkyl, vorzugsweise mit 1 bis 8, oder mit 1 bis 6 "Arylalkenyl" is an aryl group bonded through an alkenyl group, "heteroarylalkenyl" means a heteroaryl group bonded via an alkenyl group, and "heterocyclylalkenyl" means a heterocyclyl group bonded via an alkenyl group. "Arylalkynyl" denotes an aryl radical bonded via an alkynyl group, "heteroarylalkynyl" denotes a heteroaryl radical bonded via an alkynyl group, and "heterocyclylalkynyl" denotes a heterocyclyl radical bonded via an alkynyl group. According to the invention, "haloalkylthio", alone or as part of a chemical group, for straight-chain or branched S-haloalkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie (Ci-Cs)-, (CI-CÖ)- oder (Ci-C4)-Haloalkylthio, z.B. (aber nicht beschränkt auf) Trifluormethylthio, Pentafluorethylthio, Difluormethyl, 2,2-Difluoreth-l -ylthio, 2,2,2-Difluoreth-l - ylthio, 3,3,3-prop-l -ylthio. Carbon atoms, such as (Ci-Cs) -, (CI-CÖ) - or (Ci-C4) haloalkylthio, e.g. (but not limited to) trifluoromethylthio, pentafluoroethylthio, difluoromethyl, 2,2-difluoroeth-1-ylthio, 2,2,2-difluoroeth-1-ylthio, 3,3,3-prop-1-ylthio.
„Halocycloalkyl" und„Halocycloalkenyl" bedeuten durch gleiche oder verschiedene Halogenatome, wie z. B. F, Cl und Br, oder durch Haloalkyl, wie z. B. Trifluormethyl oder Difluormethyl teilweise oder vollständig substituiertes Cycloalkyl oder Cycloalkenyl , z.B. 1 -Fluorcycloprop-l -yl, 2-Fluorcycloprop- 1 -yl, 2,2-Difluorcycloprop-l -yl, 1 -Fluorcyclobut-l -yl, 1 -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 the same or different halogen atoms, such as. B. F, Cl and Br, or by haloalkyl, such as. Trifluoromethyl or difluoromethyl, partially or fully substituted cycloalkyl or cycloalkenyl, e.g. 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocyclobutyl-1, 1-trifluoromethylcycloprop-1-yl, 2-trifluoromethylcycloprop-1-yl, 1-chlorocycloprop-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 - is straight-chain or branched Si-alkyl, preferably with 1 to 8, or with 1 to 6
Kohlenstoffatomen, wie Tri-[(Ci-Cg)-, (Ci-Ce)- oder (Ci-C4)-alkyl]silyl, z.B. (aber nicht beschränkt auf) Trimethylsilyl, Triethylsilyl, Tri-(n-propyl)silyl, Tri-(iso-propyl)silyl, Tri-(n-butyl)silyl, Tri-(1 - methylprop-l -yl)silyl, Tri-(2-methylprop-l -yl)silyl, Tri(l ,l -Dimethyleth-l -yl)silyl, Tri(2,2- Dimethyleth- 1 -yl)silyl. „Trialkylsilylalkinyl" steht für einen über eine Alkinylgruppe gebundenen Trialkylsilylrest. Carbon atoms such as tri - [(Ci-Cg) -, (Ci-Ce) - or (Ci-C4) -alkyl] silyl, e.g. (but not limited to) trimethylsilyl, triethylsilyl, tri (n-propyl) silyl, tri (iso-propyl) silyl, tri (n-butyl) silyl, tri (1-methylprop-1-yl) silyl, Tri- (2-methylprop-1-yl) silyl, tri (1,1-dimethyleth-1-yl) silyl, tri (2,2-dimethyl-1-yl) silyl. "Trialkylsilylalkinyl" stands for a trialkylsilyl radical bonded via an alkynyl group.
Wenn die Verbindungen durch Wasserstoffverschiebung Tautomere bilden können, welche strukturell formal nicht durch die Formel (I) erfasst würden, so sind diese Tautomere gleichwohl von der Definition der erfindungsgemäßen Verbindungen der Formel (I) umfasst, sofern nicht ein bestimmtes Tautomer Gegenstand der Betrachtung ist. So können beispielsweise viele Carbonylverbindungen sowohl in der Ketoform wie auch in der Enolform vorliegen, wobei beide Formen durch die Definition der If the compounds can form tautomers by hydrogen shift which would not be structurally formally recognized by the formula (I), these tautomers are nevertheless encompassed by the definition of the compounds of the formula (I) according to the invention, unless a particular tautomer is the subject of consideration. For example, many carbonyl compounds may be present in both the keto form and the enol form, both of which are defined by the definition of
Verbindung der Formel (I) umfasst werden. Compound of formula (I) are included.
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 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 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. Depending on the nature and linkage of the substituents, 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). For example, if one or more alkenyl groups are present, diastereomers (Z- and E- Isomers) 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 carried out both on an analytical scale to determine the enantiomeric excess or the diastereomeric excess, as well as on a preparative scale for the preparation of test samples for the biological assay. Similarly, 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.
Sofern die Verbindungen als Feststoffe erhalten werden, kann die Reinigung auch durch If the compounds are obtained as solids, the purification can also 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. Unless individual compounds (I) are satisfactorily accessible by the routes described below, they can be prepared by derivatization of other compounds (I).
Als Isolierungs-, Reinigungs- und Stereoisomerenauftrennungsverfahren von Verbindungen der 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 Suitable isolation, purification and stereoisomer separation methods of compounds of formula (I) are those which are well known to those skilled in the art from analogous cases, e.g. through physical processes such as crystallization, chromatography, especially
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. Column chromatography and HPLC (high pressure liquid chromatography), distillation, optionally under reduced pressure, extraction and other methods, may optionally contain remaining mixtures, usually by chromatographic separation, e.g. at chiral solid phases, to be separated. For preparative amounts or on an industrial scale, such processes as crystallization, e.g. diastereomeric salts which can be obtained from the diastereomeric mixtures with optically active acids and optionally in the presence of acidic groups with optically active bases.
Synthese von N-Sulfonyl-N'-aryldiaminoalkanen und N-Sulfonyl-N'- heteroaryldiaminoalkanen der allgemeinen Formel (I) Synthesis of N-sulfonyl-N'-aryldiaminoalkanes and N-sulfonyl-N'-heteroaryldiaminoalkanes of the general formula (I)
Die erfindungsgemäßen gegebenenfalls weiter substituierten N-Sulfonyl-N'-aryldiaminoalkane und N- Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I) können nach bekannten Verfahren hergestellt werden. Die eingesetzten und untersuchten Syntheserouten gehen dabei von kommerziell erhältlichen oder leicht herstellbaren Fluroaromaten, Anilinen, Fluorheteroaromaten oder The optionally further substituted N-sulfonyl-N'-aryldiaminoalkane according to the invention and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I) can be prepared by known processes. The synthetic routes used and investigated are based on commercially available or easily prepared fluoroaromatics, anilines, fluoro heteroaromatics or
Aminoheteroaromaten sowie den entsprechenden Sulfonylchloriden aus. Vergleichbare Synthesen sind beispielsweise in W01998/22432, WO2000/017163, JP2001/328938, JP2001/261657 beschrieben. Aryl- und Heteroarylsulfonylchloridvorstufen können beispielsweise über direkte Chlorsulfonierung der entsprechenden substituierten Aromaten und Heteroaromaten (vgl. Eur J. Med. Chem. 2010, 45, 1760) oder über Diazotierung eines Amino-substituierten Aromaten oder Heteroaromaten und anschließende Chlorsulfonierung hergestellt werden (vgl. WO2005/035486). Die erfindungsgemäßen gegebenenfalls weiter substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiammoalkane der allgemeinen Formel (I) können über eine Umsetzung von gegebenenfalls weiter substituierten Aryl- oder Heteroarylfluoriden mit geeigneten gegebenenfalls weiter substituierten Diaminen und Aminoheteroaromaten and the corresponding sulfonyl chlorides. Comparable syntheses are described for example in WO1998 / 22432, WO2000 / 017163, JP2001 / 328938, JP2001 / 261657. Aryl and heteroarylsulfonyl chloride precursors may be prepared, for example, by direct chlorosulfonation of the corresponding substituted aromatics and heteroaromatics (see Eur J Med Chem., 2010, 45, 1760) or by diazotization of an amino-substituted aromatic or heteroaromatic and subsequent Chlorosulfonation are prepared (see WO2005 / 035486). The optionally further substituted N-sulfonyl-N'-aryldiaminoalkane according to the invention and N-sulfonyl-N'-heteroaryldiammoalkane of the general formula (I) can be prepared by reacting optionally further substituted aryl or heteroaryl fluorides with suitable optionally substituted diamines and
nachfolgende Kupplung mit den entsprechenden substituierten Sulfonylchloridvorstufen mit Hilfe einer geeigneten Base (z. B. Triethylamin, Pyridin oder Natriumhydroxid) in einem geeigneten Lösemittel (z. B. Tetrahydrofuran, Acetonitril, Dimethylsulfoxid oder Dichlormethan) hergestellt werden. Alternativ können die gegebenenfalls weiter substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I), wenn n für 1 steht, durch Umsetzung einer gegebenenfalls substituierten Sulfonylchloridvorstufe mit einem geeigneten gegebenenfalls weiter substituierten Bromalkylamin in ein intermediäres gegebenenfalls weiter substituiertes Sulfonylaziridin überführt werden. Durch Reaktion des intermediären gegebenenfalls weiter substituierten subsequent coupling with the corresponding substituted sulfonyl chloride precursors with the aid of a suitable base (eg triethylamine, pyridine or sodium hydroxide) in a suitable solvent (eg tetrahydrofuran, acetonitrile, dimethylsulfoxide or dichloromethane). Alternatively, the optionally further substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I), when n is 1, by reacting an optionally substituted Sulfonylchloridvorstufe with a suitable optionally substituted bromoalkylamine in an intermediate optionally further substituted sulfonylaziridine be transferred. By reaction of the intermediate optionally further substituted
Sulfonylaziridins mit einem gegebenenfalls weiter substituierten Anilin oder Aminoheteroaromaten unter Zugabe von Siliziumdioxid in einem geeigneten polar-protischen Lösemittel (z. B. Wasser) wird das gewünschte erfindungsgemäße gegebenenfalls weiter substituierte N-Sulfonyl-N' -aryldiaminoalkan oder N-Sulfonyl-N'- heteroaryldiammoalkan der Formel (I) erhalten (Schema 1). A1, A2, A3, A4, R5 und X haben im folgenden Schema 1 die zuvor definierten Bedeutungen. R3, R4, R5, R6, R7 und R8 werden beispielhaft, aber nicht einschränkend, durch H dargestellt und n steht beispielhaft, aber nicht einschränkend, für 1. Sulfonylaziridins with an optionally further substituted aniline or aminoheteroaromatics with the addition of silicon dioxide in a suitable polar protic solvent (for example water), the desired inventive optionally further substituted N-sulfonyl-N '-aryldiaminoalkan or N-sulfonyl-N' heteroaryldiammoalkane of the formula (I) (Scheme 1). A 1 , A 2 , A 3 , A 4 , R 5 and X in the following Scheme 1 have the meanings defined above. R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are exemplified, but not limited to, by H and n is illustrative, but not limiting, of FIG.
Figure imgf000058_0001
Figure imgf000058_0001
Schema 1.  Scheme 1.
Ausgewählte detaillierte Synthesebeispiele für die erfindungsgemäßen Verbindungen der allgemeinen Formeln (I) sind im Folgenden aufgeführt. Die angegebenen Beispielnummern entsprechen den in den nachstehenden Tabellen L I bis 1.50 genannten Numerierungen. 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 "F-NMR, Lösungsmittel CDC13, CD3OD oder de-DMSO, interner Standard: Tetramethylsilan δ = 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 of the compounds of the general formulas (I) according to the invention are listed below. The given example numbers correspond to the numbers given in the following tables LI to 1.50. 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 for "F-NMR, solvent CDC1 3 , CD3OD or de-DMSO, internal standard: tetramethylsilane δ = 0.00 ppm), were obtained with a Broker device, and the designated signals have the following meanings: br = broad (es); s = singlet, d = doublet, t = triplet, dd = double doublet, ddd = doublet of double doublet, m = multiplet, q = quartet, quint = quintet, sext = sextet, sept = septet, dq = double quartet, dt = double triplet. For diastereomeric mixtures, either the respective significant signals of both diastereomers or the characteristic signal of the main diastereomer are given. The abbreviations used for chemical groups have, for example, the following meanings: Me = CH 3 , Et = CH 2 CH 3 , t-Hex = C (CH 3 ) 2 CH (CH 3 ) 2, t-Bu = C (CH 3 ) 3 , n-Bu = unbranched butyl, n-Pr = unbranched propyl, i-Pr = branched propyl, c-Pr = cyclopropyl, c-hex = cyclohexyl.
Synthesebeispiele: Synthesis Examples:
Beispiel 1.3-73: N-(2- {[4-Cyan-3-(trifluormeth l)phenyl]amino}ethyl)-3-methoxybenzolsulfonamid Example 1.3-73: N- (2- {[4-cyano-3- (trifluoromethyl) phenyl] amino} ethyl) -3-methoxybenzenesulfonamide
Figure imgf000059_0001
Figure imgf000059_0001
2-Aminoethylamin (1 equiv.) und 2-Trifluormethyl-4-Fluorbenzonitril (1 equiv.) wurden unter Argon in Acetonitril gelöst und mit Triethylamin (1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde daraufhin 4 h lang bei einer Temperatur von 50 °C gerührt. Nach dem Abkühlen auf Raumtemperatur erfolgte die Zugabe von Wasser und Dichlormethan sowie eine gründliche Extraktion. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, abfiltriert und unter vermindertem Druck eingeengt. Eine Teilmenge des so erhaltenen 4-[(2-Aminoethyl)amino]-2-(trifluormethyl)benzonitrils (160 mg, 0.69 mmol) wurde in abs. Dichlormethan (20 mL) unter Argon in einem ausgeheizten Rundkolben suspendiert und mit Diisopropylethylamin (0.37 mL, 2.09 mmol) versetzt. Nach 5 Minuten Rühren bei Raumtemperatur erfolgte die Zugabe einer Lösung von 3-Methoxyphenylsulfonsäurechlorid (144 mg, 0.69 mmol) in abs. Dichlormethan (5 mL), und das resultierende Reaktionsgemisch wurde 20h lang bei Raumtemperatur gerührt. Nach der Zugabe von Wasser und Dichlormethan wurde die wässrige Phase mehrfach mit Dichlormethan extrahiert. Die vereinigten organischen Phasen wurden über Magnesiumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch 2-Aminoethylamine (1 equiv.) And 2-trifluoromethyl-4-fluorobenzonitrile (1 equiv.) Were dissolved in acetonitrile under argon and treated with triethylamine (1.5 equiv.). The resulting reaction mixture was then stirred for 4 hours at a temperature of 50 ° C. After cooling to room temperature, the addition of water and dichloromethane and a thorough extraction. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. A portion of the resulting 4 - [(2-aminoethyl) amino] -2- (trifluoromethyl) benzonitrile (160 mg, 0.69 mmol) was dissolved in abs. Dichloromethane (20 mL) was suspended under argon in a heated round bottom flask and treated with diisopropylethylamine (0.37 mL, 2.09 mmol). After stirring for 5 minutes at room temperature, the addition of a solution of 3-methoxyphenylsulfonyl chloride (144 mg, 0.69 mmol) in abs. Dichloromethane (5 mL) and the resulting reaction mixture was stirred at room temperature for 20 h. After the addition of water and dichloromethane, the aqueous phase was extracted several times with dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. By
säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurdecolumn chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) was
N-(2- {[4-Cyan-3-(trifluormethyl)phenyl]amino}-ethyl)-3-methoxybenzolsulfonamid (232 mg, 83 % der Theorie) als farbloser Feststoff isoliert. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.77 (br. S, 1H, NH), 7.69 (d, 1H), 7.49 (m, 1H), 7.36 (m, 1H), 7.28 (m, 1H), 7.22-7.17 (m, 2H), 6.97 (br. s, 1H, NH), 6.79 (m, 1H), 3.80 (s, 3H), 3.27-3.22 (m, 1H), 2.94-2.88 (m, 2H). Beispiel 1.13-34: N-(2- { [3,4-Bis(trifluormethyl)phenyl]amino} ethyl)-4-fluorbenzolsulfonamid Isolated N- (2- {[4-cyano-3- (trifluoromethyl) phenyl] amino} ethyl) -3-methoxybenzenesulfonamide (232 mg, 83% of theory) as a colorless solid. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.77 (br. S, 1H, NH), 7.69 (d, 1H), 7.49 (m, 1H), 7.36 (m, 1H), 7.28 (m , 1H), 7.22-7.17 (m, 2H), 6.97 (br s, 1H, NH), 6.79 (m, 1H), 3.80 (s, 3H), 3.27-3.22 (m, 1H), 2.94-2.88 (m, 2H). Example 1.13-34: N- (2- {[3,4-bis (trifluoromethyl) phenyl] amino} ethyl) -4-fluorobenzenesulfonamide
Figure imgf000060_0001
Figure imgf000060_0001
2-Bromoethylamin (1 equiv.) und 4-Fluorphenylsulfonylchlorid (1 equiv.) wurden unter Argon in abs. Dichlormethan gelöst und mit Triethylamin (1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde daraufhin 5 h lang bei Raumtemperatur gerührt und nach der Zugabe von Wasser und 2-Bromoethylamine (1 equiv.) And 4-fluorophenylsulfonyl chloride (1 equiv.) Were added under argon in abs. Dissolved dichloromethane and triethylamine (1.5 equiv.). The resulting reaction mixture was then stirred for 5 hours at room temperature and after the addition of water and
Dichlormethan gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, ab filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung wurde N-(2-Bromethyl)-4-Fluorbenzolsulfonamid als Intermediat erhalten, das danach in Toluol (15 mL/mmol) gelöst wurde und mit einer Lösung von Kaliumhydroxid (3 equiv) in Wasser (1 mL/mmol) versetzt. Das resultierende Reaktionsgemisch wurde 90 Minuten lang bei Raumtemperatur gerührt und nach vollständiger Umsetzung mit Essigester und Wasser versetzt sowie gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Extract dichloromethane thoroughly. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. Purification by column chromatography gave N- (2-bromoethyl) -4-fluorobenzenesulfonamide as an intermediate, which was then dissolved in toluene (15 mL / mmol) and treated with a solution of potassium hydroxide (3 equiv) in water (1 mL / mmol) , The resulting reaction mixture was stirred at room temperature for 90 minutes and, after completion of the reaction, combined with ethyl acetate and water and extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the obtained
Rohproduktes (Gradient Essigester/Heptan) wurde l-[(4-Fluorphenyl)sulfonyl]aziridin (200 mg, 82 % der Theorie) als farbloser Feststoff isoliert. l-[(4-Fluorphenyl)sulfonyl]aziridin (200 mg, 0.99 mmol), 3,4-bis(trifluormethyl)anilin (228 mg, 0.99 mmol) und Siliciumdioxid (299 mg, 4.97 mmol) wurden in Wasser (4 mL) suspendiert, und das resultierende Reaktionsgemisch wurde 3d lang bei Raumtemperatur gerührt. Nach der Zugabe von Wasser und Essigester wurde die wässrige Phase mehrfach mit Essigester extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Crude product (gradient ethyl acetate / heptane) was l - [(4-fluorophenyl) sulfonyl] aziridine (200 mg, 82% of theory) isolated as a colorless solid. l - [(4-Fluorophenyl) sulfonyl] aziridine (200 mg, 0.99 mmol), 3,4-bis (trifluoromethyl) aniline (228 mg, 0.99 mmol) and silica (299 mg, 4.97 mmol) were dissolved in water (4 mL ) and the resulting reaction mixture was stirred at room temperature for 3d. After the addition of water and ethyl acetate, the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the obtained
Rohproduktes (Gradient Essigester/Heptan) konnte N-(2- {[3,4-bis-(trifluormethyl)phenyl]amino}ethyl)- 4-fluorbenzolsulfonamid (217 mg, 51 % der Theorie) als farbloser Feststoff isoliert werden. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.88-7.81 (m, 3H), 7.62 (br. m, 1H, NH), 7.42-7.36 (m, 2H), 7.02 (s, 1H), 6.89 (m, 1H), 6.80 (m, 1H), 3.25-3.17 (m, 2H), 2.93-2.89 (m, 2H). Beispiel 1.33-34: N-(2- {[4-Fluor-3-(trifluormethyl)phenyl]amino}ethyl)-4-fluorbenzolsulfonamid Crude product (gradient ethyl acetate / heptane), N- (2- {[3,4-bis (trifluoromethyl) phenyl] amino} ethyl) - 4-fluorobenzenesulfonamide (217 mg, 51% of theory) was isolated as a colorless solid. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.88-7.81 (m, 3H), 7.62 (br, m, 1H, NH), 7.42-7.36 (m, 2H), 7.02 (s, 1H) , 6.89 (m, 1H), 6.80 (m, 1H), 3.25-3.17 (m, 2H), 2.93-2.89 (m, 2H). Example 1.33-34: N- (2- {[4-Fluoro-3- (trifluoromethyl) phenyl] amino} ethyl) -4-fluorobenzenesulfonamide
Figure imgf000061_0001
2-Bromoethylamin (1 equiv.) und 4-Fluorphenylsulfonylchlorid (1 equiv.) wurden unter Argon in abs. Dichlormethan gelöst und mit Triethylamin (1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde daraufhin 5 h lang bei Raumtemperatur gerührt und nach der Zugabe von Wasser und
Figure imgf000061_0001
2-Bromoethylamine (1 equiv.) And 4-fluorophenylsulfonyl chloride (1 equiv.) Were added under argon in abs. Dissolved dichloromethane and triethylamine (1.5 equiv.). The resulting reaction mixture was then stirred for 5 hours at room temperature and after the addition of water and
Dichlormethan gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, ab filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung wurde N-(2-Bromethyl)-4-Fluorbenzolsulfonamid als Intermediat erhalten, das danach in Toluol (15 mL/mmol) gelöst wurde und mit einer Lösung von Kaliumhydroxid (3 equiv) in Wasser (1 mL/mmol) versetzt. Das resultierende Reaktionsgemisch wurde 90 Minuten lang bei Raumtemperatur gerührt und nach vollständiger Umsetzung mit Essigester und Wasser versetzt sowie gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Extract dichloromethane thoroughly. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. Purification by column chromatography gave N- (2-bromoethyl) -4-fluorobenzenesulfonamide as an intermediate, which was then dissolved in toluene (15 mL / mmol) and treated with a solution of potassium hydroxide (3 equiv) in water (1 mL / mmol) , The resulting reaction mixture was stirred at room temperature for 90 minutes and, after completion of the reaction, combined with ethyl acetate and water and extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the obtained
Rohproduktes (Gradient Essigester/Heptan) wurde l-[(4-Fluorphenyl)sulfonyl]aziridin (200 mg, 82 % der Theorie) als farbloser Feststoff isoliert. l-[(4-Fluorphenyl)sulfonyl]aziridin (200 mg, 0.99 mmol), 4- Fluor-3-trifluormethylanilin (178 mg, 0.99 mmol) und Siliciumdioxid (299 mg, 4.97 mmol) wurden in Wasser (4 mL) suspendiert, und das resultierende Reaktionsgemisch wurde 3d lang bei Raumtemperatur gerührt. Nach der Zugabe von Wasser und Essigester wurde die wässrige Phase mehrfach mit Essigester extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen  Crude product (gradient ethyl acetate / heptane) was l - [(4-fluorophenyl) sulfonyl] aziridine (200 mg, 82% of theory) isolated as a colorless solid. l - [(4-Fluorophenyl) sulfonyl] aziridine (200 mg, 0.99 mmol), 4-fluoro-3-trifluoromethylaniline (178 mg, 0.99 mmol) and silica (299 mg, 4.97 mmol) were suspended in water (4 mL) and the resulting reaction mixture was stirred at room temperature for 3d. After the addition of water and ethyl acetate, the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the obtained
Rohproduktes (Gradient Essigester/Heptan) wurde N-(2- {[4-Fluor-3-Crude product (gradient ethyl acetate / heptane) was N- (2- {[4-fluoro-3-
(trifluormethyl)phenyl]amino}ethyl)-4-fluorbenzolsulfonamid (297 mg, 79 % der Theorie) als farbloser Feststoff isoliert. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.89-7.83 (m, 2H), 7.78 (br. t, 1H, NH), 7.43- 7.38 (m, 2H), 7.20-7.17 (m, 1H), 6.78-6.73 (m, 2H), 5.98 (br. t, 1H, NH), 3.14-3.09 (m, 2H), 2.91-2.86 (m, 2H). Beispiel 1.33-35: N-(2- { [4-Fluor-3 -(trifluormethyl)phenyl] amino } ethyl)-4-chlorbenzolsulfonamid (trifluoromethyl) phenyl] amino} ethyl) -4-fluorobenzenesulfonamide (297 mg, 79% of theory) as a colorless solid. 'H-NMR (400 MHz, de-DMSO δ, ppm) 7.89-7.83 (m, 2H), 7.78 (br.t, 1H, NH), 7.43-7.38 (m, 2H), 7.20-7.17 (m, 1H), 6.78-6.73 (m, 2H), 5.98 (br t, 1H, NH), 3.14-3.09 (m, 2H), 2.91-2.86 (m, 2H). Example 1.33-35: N- (2- {[4-Fluoro-3 - (trifluoromethyl) phenyl] amino} ethyl) -4-chlorobenzenesulfonamide
Figure imgf000062_0001
2-Bromoethylamin (1 equiv.) und 4-Chlorphenylsulfonylchlorid (1 equiv.) wurden unter Argon in abs. Dichlormethan gelöst und mit Triethylamin (1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde daraufhin 5 h lang bei Raumtemperatur gerührt und nach der Zugabe von Wasser und
Figure imgf000062_0001
2-Bromoethylamine (1 equiv.) And 4-chlorophenylsulfonyl chloride (1 equiv.) Were added under argon in abs. Dissolved dichloromethane and triethylamine (1.5 equiv.). The resulting reaction mixture was then stirred for 5 hours at room temperature and after the addition of water and
Dichlormethan gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, ab filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung wurde N-(2-Bromethyl)-4-Chlorbenzolsulfonamid als Intermediat erhalten, das danach in Toluol (15 mL/mmol) gelöst wurde und mit einer Lösung von Kaliumhydroxid (3 equiv) in Wasser (1 mL/mmol) versetzt. Das resultierende Reaktionsgemisch wurde 90 Minuten lang bei Raumtemperatur gerührt und nach vollständiger Umsetzung mit Essigester und Wasser versetzt sowie gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Extract dichloromethane thoroughly. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. Purification by column chromatography gave N- (2-bromoethyl) -4-chlorobenzenesulfonamide as an intermediate, which was then dissolved in toluene (15 mL / mmol) and treated with a solution of potassium hydroxide (3 equiv) in water (1 mL / mmol) , The resulting reaction mixture was stirred at room temperature for 90 minutes and, after completion of the reaction, combined with ethyl acetate and water and extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the obtained
Rohproduktes (Gradient Essigester/Heptan) wurde l-[(4-Chlorphenyl)sulfonyl]aziridin (150 mg, 87 % der Theorie) als farbloser Feststoff isoliert. l-[(4-Chlorphenyl)sulfonyl]aziridin (150 mg, 0.69 mmol), 4- Fluor-3-trifluormethylanilin (123 mg, 0.69 mmol) und Siliciumdioxid (100 mg, 1.66 mmol) wurden in Wasser (2 mL) suspendiert, und das resultierende Reaktionsgemisch wurde 20h lang bei  Crude product (gradient ethyl acetate / heptane) was l - [(4-chlorophenyl) sulfonyl] aziridine (150 mg, 87% of theory) isolated as a colorless solid. l - [(4-Chlorophenyl) sulfonyl] aziridine (150 mg, 0.69 mmol), 4-fluoro-3-trifluoromethylaniline (123 mg, 0.69 mmol) and silica (100 mg, 1.66 mmol) were suspended in water (2 mL) and the resulting reaction mixture was allowed to stand for 20h
Raumtemperatur gerührt, davon 90 Minuten im Ultraschallbad. Nach der Zugabe von Wasser undRoom temperature stirred, thereof 90 minutes in an ultrasonic bath. After the addition of water and
Essigester wurde die wässrige Phase mehrfach mit Essigester extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurde N-(2- {[4-Fluor-3-(trifluormethyl)phenyl]amino}ethyl)-4-chlorbenzolsulfonamid (210 mg, 77 % der Theorie) als farbloser Feststoff isoliert. 'H-NMR (400 MHz, CDC13 δ, ppm) 7.80 (d, 2H), 7.48 (d, 2H), 7.00 (m, 1H), 6.70-6.64 (m, 2H), 4.92 (br. t, 1H, NH), 4.02 (br. m, 1H, NH), 6.79 (m, 1H), 3.30-3.25 (m, 2H), 3.22-3.17 (m, 2H). Beispiel 1.33-50: N-(2- {[4-Fluor-3-(trifluormethyl)phenyl]amino}ethyl)-4-methylbenzolsulfonamid Essigester the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) was N- (2- {[4-fluoro-3- (trifluoromethyl) phenyl] amino} ethyl) -4-chlorobenzenesulfonamide (210 mg, 77% of theory) as colorless Solid isolated. 'H-NMR (400 MHz, CDC1 3 δ, ppm) 7.80 (d, 2H), 7.48 (d, 2H), 7.00 (m, 1H), 6.70-6.64 (m, 2H), 4.92 (br. 1H, NH), 4.02 (br, m, 1H, NH), 6.79 (m, 1H), 3.30-3.25 (m, 2H), 3.22-3.17 (m, 2H). Example 1.33-50: N- (2- {[4-Fluoro-3- (trifluoromethyl) phenyl] amino} ethyl) -4-methylbenzenesulfonamide
Figure imgf000063_0001
2-Bromoethylamin (1 equiv.) und 4-Methylphenylsulfonylchlorid (1 equiv.) wurden unter Argon in abs. Dichlormethan gelöst und mit Triethylamin (1.5 equiv) versetzt. Das resultierende Reaktionsgemisch wurde daraufhin 5 h lang bei Raumtemperatur gerührt und nach der Zugabe von Wasser und
Figure imgf000063_0001
2-Bromoethylamine (1 equiv.) And 4-methylphenylsulfonyl chloride (1 equiv.) Were added under argon in abs. Dissolved dichloromethane and triethylamine (1.5 equiv.). The resulting reaction mixture was then stirred for 5 hours at room temperature and after the addition of water and
Dichlormethan gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, ab filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung wurde N-(2-Bromethyl)-4-methylbenzolsulfonamid (1.00 g, 3.54 mmol) als Intermediat erhalten, das danach in Toluol (100 mL) gelöst wurde und mit einer Lösung von Kaliumhydroxid (1.19 g, 21.27 mmol) in Wasser (15mL) versetzt. Das resultierende Reaktionsgemisch wurde 90 Minuten lang bei Raumtemperatur gerührt und nach vollständiger Umsetzung mit Essigester und Wasser versetzt sowie gründlich extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurde l-[(4-Methylphenyl)sulfonyl]aziridin (781 mg, 98 % der Theorie) als farbloser Feststoff isoliert. 'H-NMR (400 MHz, CDC13 δ, ppm) 7.85 (d, 2H), 7.37 (d, 1H), 2.45 (s, 3H), 2.42-2.30 (m, 4H). l-[(4-Methylphenyl)sulfonyl]aziridin (120 mg, 9.61 mmol), 4-Fluor-3-trifluormethylanilin (109 mg, 0.61 mmol) und Siliciumdioxid (110 mg, 1.83 mmol) wurden in Wasser (2 mL) suspendiert, und das resultierende Reaktionsgemisch wurde 20h lang bei Raumtemperatur gerührt. Nach der Zugabe von Wasser und Essigester wurde die wässrige Phase mehrfach mit Essigester extrahiert. Die vereinigten organischen Phasen wurden über Natriumsulfat getrocknet, filtriert und unter vermindertem Druck eingeengt. Durch säulenchromatographische Reinigung des erhaltenen Rohproduktes (Gradient Essigester/Heptan) wurde N-(2- {[4-Fluor-3- (trifluormethyl)phenyl]amino}ethyl)-4-methylbenzolsulfonamid (70 mg, 31 % der Theorie) als farbloser Feststoff isoliert. 'H-NMR (400 MHz, CDCI3 δ, ppm) 7.75 (d, 2H), 7.31 (d, 2H), 7.00 (m, 1H), 6.68- 6.64 (m, 2H), 4.79 (br. t, 1H, NH), 4.05 (br. m, 1H, NH), 6.79 (m, 1H), 3.25-3.16 (m, 4H), 2.43 (s, 3H). Extract dichloromethane thoroughly. The combined organic phases were dried over sodium sulfate, filtered off and concentrated under reduced pressure. Purification by column chromatography gave N- (2-bromoethyl) -4-methylbenzenesulfonamide (1.00 g, 3.54 mmol) as an intermediate, which was then dissolved in toluene (100 mL) and treated with a solution of potassium hydroxide (1.19 g, 21.27 mmol) in Water (15mL) offset. The resulting reaction mixture was stirred at room temperature for 90 minutes and, after completion of the reaction, combined with ethyl acetate and water and extracted thoroughly. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the crude product obtained (gradient ethyl acetate / heptane) was l - [(4-methylphenyl) sulfonyl] aziridine (781 mg, 98% of theory) isolated as a colorless solid. 'H NMR (400 MHz, CDC1 3 δ, ppm) 7.85 (d, 2H), 7.37 (d, 1H), 2.45 (s, 3H), 2.42-2.30 (m, 4H). l - [(4-Methylphenyl) sulfonyl] aziridine (120 mg, 9.61 mmol), 4-fluoro-3-trifluoromethylaniline (109 mg, 0.61 mmol) and silica (110 mg, 1.83 mmol) were suspended in water (2 mL) and the resulting reaction mixture was stirred at room temperature for 20 hours. After the addition of water and ethyl acetate, the aqueous phase was extracted several times with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered and concentrated under reduced pressure. By column chromatographic purification of the resulting crude product (gradient ethyl acetate / heptane) was N- (2- {[4-fluoro-3- (trifluoromethyl) phenyl] amino} ethyl) -4-methylbenzenesulfonamide (70 mg, 31% of theory) as a colorless Solid isolated. 'H NMR (400 MHz, CDCl3 δ, ppm) 7.75 (d, 2H), 7.31 (d, 2H), 7.00 (m, 1H), 6.68-6.64 (m, 2H), 4.79 (br t, 1H , NH), 4.05 (br, m, 1H, NH), 6.79 (m, 1H), 3.25-3.16 (m, 4H), 2.43 (s, 3H).
In Analogie zu den oben angeführten und an entsprechender Stelle rezitierten Herstellungsbeispielen und unter Berücksichtigung der allgemeinen Angaben zur Herstellung von N-Sulfonyl-N'- aryldiaminoalkanen und N-Sulfonyl-N'- heteroaryldiaminoalkanen der allgemeinen Formel (I) erhält man die nachfolgend genannten Verbindungen, wobei ein Pfeil im Falle von R5 für eine Bindung zum Schwefel und im Falle von R6 für eine Bindung zum Stickstoff in der allgemeinen Formel (I) steht,
Figure imgf000064_0001
By analogy with the production examples recited above and recited at the appropriate place and taking into account the general information on the preparation of N-sulfonyl-N'-aryldiaminoalkanen and N-sulfonyl-N'-heteroaryldiaminoalkanen the general formula (I) gives the compounds mentioned below in which, in the case of R 5 , an arrow represents a bond to the sulfur and in the case of R 6 represents a bond to the nitrogen in the general formula (I),
Figure imgf000064_0001
Tabelle LI : Bevorzugt für die Verwendung von Verbindungen der Formel (L I) sind die Verbindungen 1.1-1 bis 1.1-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.1-1 bis 1.1-650 der Tabelle LI sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Preferred for the use of compounds of the formula (LI) are the compounds 1.1-1 to 1.1-650, in which R 5 and R 6 have the meanings of Table 1 indicated in the respective line. The compounds 1.1-1 to 1.1-650 of the table LI are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Tabelle 1 Table 1
Figure imgf000064_0002
Figure imgf000064_0002
Figure imgf000065_0001
R5 R6
Figure imgf000065_0001
R 5 R 6
4-(cyclo-Propylamino)phenyl H4- (cyclopropylamino) phenyl H
NH2 HH NH 2
4-Methylphenyl H4-methylphenyl H
3 ,4-Dimethylphenyl H3, 4-dimethylphenyl H
2,3-Dimethylphenyl H2,3-dimethylphenyl H
2-Methyl-3 -Chlorphenyl H2-methyl-3-chlorophenyl H
3 -Chlorphenyl H3-chlorophenyl H
3-Methylphenyl H3-methylphenyl H
3-Cyanophenyl H3-cyanophenyl H
3 ,4-Dichlorphenyl H3, 4-dichlorophenyl H
3,5-Dichlorphenyl H3,5-dichlorophenyl H
2,5-Dichlorphenyl H2,5-dichlorophenyl H
2,4-Dichlorphenyl H2,4-dichlorophenyl H
2-Chlorphenyl H2-Chlorophenyl H
2-Fluorphenyl H2-fluorophenyl H
3 ,4-Difluorphenyl H3,4-difluorophenyl H
3-Fluorphenyl H3-fluorophenyl H
3,5-Difluorphenyl H3,5-difluorophenyl H
3 -Difluormethoxyphenyl H3-difluoromethoxyphenyl H
3 -Trifluormethoxyphenyl H3 -trifluoromethoxyphenyl H
2,3-Dichlorphenyl H2,3-dichlorophenyl H
2-Trifluormethylphenyl H2-trifluoromethylphenyl H
2-Methoxyphenyl H2-methoxyphenyl H
3-Bromphenyl H3-bromophenyl H
3-Iodphenyl H3-iodophenyl H
3 -Methoxyphenyl H3-methoxyphenyl H
3 -Hydropxyphenyl H3 -hydroxyphenyl H
Pyridin-3-yl HPyridin-3-yl H
Pyridin-4-yl H Pyridin-4-yl H
H R5 R6 H R 5 R 6
H H
H H
H H
H H
H H
H H
H H
H H
HH
H H
Aminophenyl H Aminophenyl H
Methylammophenyl HMethylammophenyl H
Ethylammophenyl HEthylammophenyl H
Dimethylaminophenyl H Dimethylaminophenyl H
Figure imgf000068_0001
Figure imgf000068_0001
Figure imgf000069_0001
Figure imgf000069_0001
Figure imgf000070_0001
R5 R6
Figure imgf000070_0001
R 5 R 6
4-Trifluormethoxyphenyl 4-trifluoromethoxyphenyl
o 1 o 1
4-Cyanophenyl 4-cyanophenyl
o 1 o 1
4-Hydroxycarbonylphenyl H4-hydroxycarbonylphenyl H
4-Methoxycarbonylphenyl H4-methoxycarbonylphenyl H
4-Ethoxycarbonylphenyl H4-ethoxycarbonylphenyl H
4-tert-Butyloxycarbonylphenyl H4-tert-butyloxycarbonylphenyl H
3 -Hydroxycarbonylphenyl H3 -hydroxycarbonylphenyl H
3 -Methoxycarbonylphenyl H3-methoxycarbonylphenyl H
3 -Ethoxycarbonylphenyl H3 -ethoxycarbonylphenyl H
2-Methoxycarbonylphenyl H2-methoxycarbonylphenyl H
2-Ethoxycarbonylphenyl H2-ethoxycarbonylphenyl H
3 ,4-Dimethoxyphenyl H3,4-dimethoxyphenyl H
Benzyl HBenzyl H
(4-Methylphenyl)methyl H(4-methylphenyl) methyl H
(3 -Methylphenyl)methyl H(3-methylphenyl) methyl H
(3 ,4-Dimethylphenyl)methyl H(3, 4-dimethylphenyl) methyl H
(2-Methylphenyl)methyl H(2-methylphenyl) methyl H
(2,4-Dimethylphenyl)methyl H(2,4-dimethylphenyl) methyl H
1-Phenyleth-l-yl H1-phenyleth-1-yl H
(4-Fluorphenyl)methyl H(4-fluorophenyl) methyl H
(3 -Fluorphenyl)methyl H(3-fluorophenyl) methyl H
(3 ,4-Difluorphenyl)methyl H(3,4-difluorophenyl) methyl H
(2-Fluorphenyl)methyl H(2-fluorophenyl) methyl H
(2,4-Difluorphenyl)methyl H(2,4-difluorophenyl) methyl H
(2,5 -Difluorphenyl)methyl H(2,5-difluorophenyl) methyl H
(3,5 -Difluorphenyl)methyl H(3,5-difluorophenyl) methyl H
(4-Chlorphenyl)methyl H(4-chlorophenyl) methyl H
(3 -Chlorphenyl)methyl H(3-chlorophenyl) methyl H
(3 ,4-Dichlorphenyl)methyl H(3, 4-dichlorophenyl) methyl H
(2-Chlorphenyl)methyl H(2-chlorophenyl) methyl H
(2,4-Dichlorphenyl)methyl H(2,4-dichlorophenyl) methyl H
(2,5 -Dichlorphenyl)methyl H No. R5 R6 (2,5-dichlorophenyl) methyl H No. R 5 R 6
171 (3,5 -Dichlorphenyl)methyl H171 (3,5-dichlorophenyl) methyl H
172 (4-Bromphenyl)methyl H172 (4-bromophenyl) methyl H
173 (3 -Bromphenyl)methyl H173 (3-bromophenyl) methyl H
174 (2-Bromphenyl)methyl H174 (2-bromophenyl) methyl H
175 (4-Nitrophenyl)methyl H175 (4-nitrophenyl) methyl H
176 (3 -Nitrophenyl)methyl H176 (3-nitrophenyl) methyl H
177 (2-Nitrophenyl)methyl H177 (2-nitrophenyl) methyl H
178 (4-Trifluormethylphenyl)methyl H178 (4-trifluoromethylphenyl) methyl H
179 (3 -Trifluormethylphenyl)methyl H179 (3-trifluoromethylphenyl) methyl H
180 (2-Trifluormethylphenyl)methyl H180 (2-trifluoromethylphenyl) methyl H
181 (4-Cyanophenyl)methyl H181 (4-cyanophenyl) methyl H
182 (3 -Cyanophenyl)methyl H182 (3-cyanophenyl) methyl H
183 (2-Cyanophenyl)methyl H183 (2-cyanophenyl) methyl H
184 (4-Trifluormethoxyphenyl)methyl H184 (4-trifluoromethoxyphenyl) methyl H
185 (3 -Trifluormethoxyphenyl)methyl H185 (3-trifluoromethoxyphenyl) methyl H
186 (4-Trifluormethylthiophenyl)methyl H186 (4-trifluoromethylthiophenyl) methyl H
187 (3-Trifluormethylthiophenyl)methyl H187 (3-trifluoromethylthiophenyl) methyl H
188 (4-Difluormethoxyphenyl)methyl H188 (4-difluoromethoxyphenyl) methyl H
189 (3 -Difluormethoxyphenyl)methyl H189 (3-difluoromethoxyphenyl) methyl H
190 (4-Methoxycarbonylphenyl)methyl H190 (4-methoxycarbonylphenyl) methyl H
191 (3 -Methoxycarbonylphenyl)methyl H191 (3-Methoxycarbonylphenyl) methyl H
192 (4-Ethoxycarbonylphenyl)methyl H192 (4-ethoxycarbonylphenyl) methyl H
193 (3 -Ethoxycarbonylphenyl)methyl H193 (3-ethoxycarbonylphenyl) methyl H
194 (4-Hydroxycarbonylphenyl)methyl H194 (4-hydroxycarbonylphenyl) methyl H
195 (3 -Hydr oxycarbonylphenyl)methyl H195 (3-hydoxycarbonylphenyl) methyl H
196 (6-Chlorpyridin-3 -yl)methyl H196 (6-chloropyridin-3-yl) methyl H
197 (Pyridin-3 -yl)methyl H197 (pyridin-3-yl) methyl H
198 (Pyridin-4-yl)methyl H198 (pyridin-4-yl) methyl H
199 (Pyridin-2-yl)methyl H199 (pyridin-2-yl) methyl H
200 (6-Trifluormethylpyridin-3-yl)methyl H200 (6-trifluoromethylpyridin-3-yl) methyl H
201 2-(3-Fluorphenyl)eth-l-yl H201 2- (3-fluorophenyl) eth-1-yl H
202 2-(4-Fluorphenyl)eth- 1 -yl H202 2- (4-fluorophenyl) eth-1-yl H
203 2-(2-Fluorphenyl)eth- 1 -yl H203 2- (2-fluorophenyl) eth-1-yl H.
204 2-(2-Chlorphenyl)eth- 1 -yl H204 2- (2-chlorophenyl) eth-1-yl H
205 2-(3-Chlorphenyl)eth-l-yl H No. R5 R6 205 2- (3-chlorophenyl) eth-1-yl H No. R 5 R 6
206 2-(4-Chlorphenyl)eth- 1 -yl H206 2- (4-chlorophenyl) eth-1-yl H
207 2-(2-Bromphenyl)eth- 1 -yl H207 2- (2-bromophenyl) eth-1-ylyl H
208 2-(3 -Bromphenyl)eth- 1 -yl H208 2- (3-Bromophenyl) eth-1-yl H
209 2-(4-Bromphenyl)eth- 1 -yl H209 2- (4-bromophenyl) eth-1-yl H
210 2-(2-Cyanophenyl)eth- 1 -yl H210 2- (2-cyanophenyl) eth-1-yl H.
211 2-(3-Cyanophenyl)eth-l-yl H211 2- (3-cyanophenyl) eth-1-yl H
212 2-(4-Cyanophenyl)eth- 1 -yl H212 2- (4-cyanophenyl) eth-1-yl H.
213 2-(2-Trifluormethylphenyl)eth- 1 -yl H213 2- (2-trifluoromethylphenyl) eth-1-yl H
214 2-(3 -Trifluormethylphenyl)eth- 1 -yl H214 2- (3-trifluoromethylphenyl) eth-1-yl H
215 2-(4-Trifluormethylphenyl)eth- 1 -yl H215 2- (4-trifluoromethylphenyl) eth-1-yl H
216 2-(2-Methoxyphenyl)eth- 1 -yl H216 2- (2-methoxyphenyl) eth-1-yl H.
217 2-(3 -Methoxyphenyl)eth- 1 -yl H217 2- (3-Methoxyphenyl) eth-1-yl H
218 2-(4-Methoxyphenyl)eth- 1 -yl H218 2- (4-methoxyphenyl) eth-1-yl H
219 2-(4-Methylphenyl)eth- 1 -yl H219 2- (4-methylphenyl) eth-1-yl H
220 2-(2-Methylphenyl)eth- 1 -yl H220 2- (2-methylphenyl) eth-1-yl H
221 (4-Cyanophenyl)methyl CH3 221 (4-cyanophenyl) methyl CH 3
222 (3 -Cyanophenyl)methyl CH3 222 (3 -Cyanophenyl) methyl CH 3
223 (4-Trifluormethylphenyl)methyl CH3 223 (4-trifluoromethylphenyl) methyl CH 3
224 (3 -Trifluormethylphenyl)methyl CH3 224 (3-trifluoromethylphenyl) methyl CH 3
225 (4-Nitrophenyl)methyl CH3 225 (4-nitrophenyl) methyl CH 3
226 (2-Trifluormethoxyphenyl)methyl CH3 226 (2-trifluoromethoxyphenyl) methyl CH 3
227 (4-Chlorphenyl)methyl CH3 227 (4-chlorophenyl) methyl CH 3
228 (4-Bromphenyl)methyl CH3 228 (4-bromophenyl) methyl CH 3
229 (4-Fluorphenyl)methyl CH3 229 (4-fluorophenyl) methyl CH 3
230 (4-Methylphenyl)methyl CH3 230 (4-Methylphenyl) methyl CH 3
231 (4-Cyanophenyl)methyl 231 (4-cyanophenyl) methyl
0  0
232 (3 -Cyanophenyl)methyl V 0 232 (3-cyanophenyl) methyl V 0
233 (4-Trifluormethylphenyl)methyl V 0 233 (4-trifluoromethylphenyl) methyl V 0
234 (3 -Trifluormethylphenyl)methyl V 0 No. R5 R6 234 (3-trifluoromethylphenyl) methyl V 0 No. R 5 R 6
235 (4-Nitrophenyl)methyl V 0 235 (4-nitrophenyl) methyl V 0
236 (3 -Nitrophenyl)methyl V 0 236 (3-nitrophenyl) methyl V 0
237 (4-Chlorphenyl)methyl V 0 237 (4-chlorophenyl) methyl V 0
238 (4-Bromphenyl)methyl V 0 238 (4-bromophenyl) methyl V 0
239 (4-Fluorphenyl)methyl 239 (4-fluorophenyl) methyl
0  0
240 (4-Methylphenyl)methyl V 0 240 (4-methylphenyl) methyl V 0
241 (4-Cyanophenyl)methyl 241 (4-cyanophenyl) methyl
0  0
242 (3 -Cyanophenyl)methyl 242 (3-cyanophenyl) methyl
0  0
243 (4-Trifluormethylphenyl)methyl 243 (4-trifluoromethylphenyl) methyl
0  0
244 (3 -Trifluormethylphenyl)methyl 244 (3-trifluoromethylphenyl) methyl
0  0
245 (4-Nitrophenyl)methyl 245 (4-nitrophenyl) methyl
0  0
246 (3 -Nitrophenyl)methyl 246 (3-nitrophenyl) methyl
0  0
247 (4-Chlorphenyl)methyl 247 (4-chlorophenyl) methyl
0 R5 R6 0 R 5 R 6
(4-Bromphenyl)methyl (4-bromophenyl) methyl
0  0
(4-Fluorphenyl)methyl (4-fluorophenyl) methyl
0  0
(4-Methylphenyl)methyl (4-methylphenyl) methyl
0  0
(4-Cyanophenyl)methyl (4-cyanophenyl) methyl
(3 -Cyanophenyl)methyl (3-cyanophenyl) methyl
(4-Trifluormethylphenyl)methyl (4-trifluoromethylphenyl) methyl
(3 -Trifluormethylphenyl)methyl (3-trifluoromethylphenyl) methyl
(4-Nitrophenyl)methyl (4-nitrophenyl) methyl
(3 -Nitrophenyl)methyl (3-nitrophenyl) methyl
(4-Chlorphenyl)methyl (4-chlorophenyl) methyl
(4-Bromphenyl)methyl (4-bromophenyl) methyl
(4-Fluorphenyl)methyl
Figure imgf000076_0001
(4-fluorophenyl) methyl
Figure imgf000076_0001
Figure imgf000077_0001
No. R5 R6
Figure imgf000077_0001
No. R 5 R 6
291 2-(2,6-Difluorphenyl)eth- 1 -yl H291 2- (2,6-Difluorophenyl) eth-1-yl H
292 2-(2,5-Difluorphenyl)eth- 1 -yl H292 2- (2,5-difluorophenyl) eth-1-ylyl H
293 2-(2,4-Difluorphenyl)eth- 1 -yl H293 2- (2,4-Difluorophenyl) eth-1-yl H
294 2-(2,6-Dichlorphenyl)eth- 1 -yl H294 2- (2,6-dichlorophenyl) eth-1-ylyl H
295 2-(2,5-Dichlorphenyl)eth- 1 -yl H295 2- (2,5-dichlorophenyl) eth-1-yl H
296 2-(2,4-Dichlorphenyl)eth- 1 -yl H296 2- (2,4-dichlorophenyl) eth-1-yl H
297 2-(2,3-Dichlorphenyl)eth-l-yl H297 2- (2,3-dichlorophenyl) eth-1-yl H
298 2-(3,5-Dichlorphenyl)eth-l-yl H298 2- (3,5-dichlorophenyl) eth-1-yl H
299 2-(4-Nitrophenyl)eth- 1 -yl H299 2- (4-nitrophenyl) eth-1-yl H
300 2-(2-Nitrophenyl)eth- 1 -yl H 300 2- (2-nitrophenyl) eth-1-ylyl H
301 H 301 H
302 Pyrimidin-4-ylmethyl H302 pyrimidin-4-ylmethyl H
303 Pyrazin-2-ylmethyl H303 pyrazine-2-ylmethyl H
304 Pyridazin-3 -ylmethyl H304 pyridazine-3-ylmethyl H
305 Pyridazin-4-ylmethyl H305 pyridazin-4-ylmethyl H
306 Pyrimidin-2-ylmethyl H306 pyrimidin-2-ylmethyl H
307 Pyrimidin- 5 -ylmethyl H307 pyrimidine-5-ylmethyl H
308 (6-Methylpyridin-2-yl)methyl H308 (6-methylpyridin-2-yl) methyl H
309 l-(Pyridin-3-yl)ethyl H309 l- (pyridin-3-yl) ethyl H
310 l-(Pyridin-2-yl)ethyl H310 L- (pyridin-2-yl) ethyl H
311 (2-Methylpyridin-4-yl)methyl H311 (2-methylpyridin-4-yl) methyl H
312 (4-Hydroxyphenyl)methyl H312 (4-hydroxyphenyl) methyl H
313 (3 -Hydr oxyphenyl)methyl H313 (3-hydroxyphenyl) methyl H
314 1 -(Pyrazin-2-yl)ethyl H314 1 - (pyrazine-2-yl) ethyl H
315 (5-Methylpyrazin-2-yl)methyl H315 (5-methylpyrazine-2-yl) methyl H
316 (2-Methylpyrimidin-2-yl)methyl H316 (2-methylpyrimidin-2-yl) methyl H
317 (2-Cyanopyridin-4-yl)methyl H317 (2-cyanopyridin-4-yl) methyl H
318 (4-Ethenylphenyl)methyl H318 (4-ethenylphenyl) methyl H
319 2,3-Dihydro- 1 H-indan- 1 -yl H319 2,3-dihydro-1H-indan-1-yl-H
320 (2-Formylphenyl)methyl H320 (2-formylphenyl) methyl H
321 (3 -Formylphenyl)methyl H321 (3-formylphenyl) methyl H
322 (4-Formylphenyl)methyl H322 (4-formylphenyl) methyl H
323 (2-Ethylphenyl)methyl H323 (2-ethylphenyl) methyl H
324 (3 -Ethylphenyl)methyl H No. R5 R6 324 (3-ethylphenyl) methyl H No. R 5 R 6
325 (4-Ethylphenyl)methyl H325 (4-ethylphenyl) methyl H
326 1 -Phenylpropan- 1 -yl H326 1 -phenylpropane-1-yl H.
327 (2-iso-Propylphenyl)methyl H327 (2-iso-propylphenyl) methyl H
328 (3 -iso-Propylphenyl)methyl H328 (3-iso-propylphenyl) methyl H
329 (4-iso-Propylphenyl)methyl H329 (4-iso-propylphenyl) methyl H
330 (2-tert-Butylphenyl)methyl H330 (2-tert-butylphenyl) methyl H
331 (3 -tert-Butylphenyl)methyl H331 (3-tert-butylphenyl) methyl H
332 (4-tert-Butylphenyl)methyl H332 (4-tert-butylphenyl) methyl H
333 (2-n-Propylphenyl)methyl H333 (2-n-Propylphenyl) methyl H
334 (3 -n-Propylphenyl)methyl H334 (3-n-propylphenyl) methyl H
335 (4-n-Propylphenyl)methyl H335 (4-n-Propylphenyl) methyl H
336 (2-c-Propylphenyl)methyl H336 (2-c-Propylphenyl) methyl H
337 (3 -c-Propylphenyl)methyl H337 (3-C-Propylphenyl) methyl H
338 (4-c-Propylphenyl)methyl H338 (4-c-Propylphenyl) methyl H
339 1 -(4-Methylphenyl)eth- 1 -yl H339 1 - (4-methylphenyl) eth-1-yl H
340 1 -(3 -Methylphenyl)eth- 1 -yl H340 1 - (3-methylphenyl) eth-1-yl H
341 1 -(2-Methylphenyl)eth- 1 -yl H341 1 - (2-methylphenyl) eth-1-ylyl H
342 (2,5 -Dimethylphenyl)methyl H342 (2,5-dimethylphenyl) methyl H
343 (3,5 -Dimethylphenyl)methyl H343 (3,5-dimethylphenyl) methyl H
344 (2,3-Dimethylphenyl)methyl H344 (2,3-dimethylphenyl) methyl H
345 (2,6-Dimethylphenyl)methyl H345 (2,6-dimethylphenyl) methyl H
346 (2-Methoxyphenyl)methyl H346 (2-methoxyphenyl) methyl H
347 (3 -Methoxyphenyl)methyl H347 (3-methoxyphenyl) methyl H
348 (4-Methoxyphenyl)methyl H348 (4-methoxyphenyl) methyl H
349 (2,5 -Dimethoxyphenyl)methyl H349 (2,5-dimethoxyphenyl) methyl H
350 (3,5 -Dimethoxyphenyl)methyl H350 (3,5-dimethoxyphenyl) methyl H
351 (2,4-Dimethoxyphenyl)methyl H351 (2,4-dimethoxyphenyl) methyl H
352 (6-Methoxypyridin-2-yl)methyl H352 (6-methoxypyridin-2-yl) methyl H
353 (5-Methoxypyridin-2-yl)methyl H353 (5-methoxypyridin-2-yl) methyl H
354 (6-Methoxypyridin-3-yl)methyl H354 (6-methoxypyridin-3-yl) methyl H
355 (5-Methoxypyrazin-2-yl)methyl H355 (5-methoxypyrazine-2-yl) methyl H
356 (2-Methoxypyrimidin-5-yl)methyl H356 (2-methoxypyrimidin-5-yl) methyl H
357 (3 -Fluor-4-Methylphenyl)methyl H357 (3-fluoro-4-methylphenyl) methyl H
358 (2-Fluor-4-Methylphenyl)methyl H358 (2-fluoro-4-methylphenyl) methyl H
359 (4-Fluor-2-Methylphenyl)methyl H No. R5 R6 359 (4-fluoro-2-methylphenyl) methyl H No. R 5 R 6
360 (4-Fluor-3 -Methylphenyl)methyl H360 (4-fluoro-3-methylphenyl) methyl H
361 1 -(3-Fluorphenyl)eth- 1 -yl H361 1 - (3-fluorophenyl) eth-1-ylyl H
362 1 -(4-Fluorphenyl)eth- 1 -yl H362 1 - (4-fluorophenyl) eth-1-yl H
363 1 -(2-Fluorphenyl)eth- 1 -yl H363 1 - (2-fluorophenyl) eth-1-yl H
364 1 -(2-Chlorphenyl)eth- 1 -yl H364 1 - (2-Chlorophenyl) eth-1-ylyl H
365 1 -(3-Chlorphenyl)eth- 1 -yl H365 1 - (3-chlorophenyl) eth-1-yl H
366 1 -(4-Chlorphenyl)eth- 1 -yl H366 1 - (4-chlorophenyl) eth-1-yl H
367 1 -(2-Bromphenyl)eth- 1 -yl H367 1 - (2-bromophenyl) eth-1-yl H
368 1 -(3 -Bromphenyl)eth- 1 -yl H368 1 - (3-Bromophenyl) eth-1-yl H
369 1 -(4-Bromphenyl)eth- 1 -yl H369 1 - (4-bromophenyl) eth-1-yl H
370 1 -(2-Cyanophenyl)eth- 1 -yl H370 1 - (2-cyanophenyl) eth-1-yl H
371 1 -(3-Cyanophenyl)eth- 1 -yl H371 1 - (3-cyanophenyl) eth-1-yl H
372 1 -(4-Cyanophenyl)eth- 1 -yl H372 1 - (4-cyanophenyl) eth-1-yl H
373 1 -(2-Trifluormethylphenyl)eth- 1 -yl H373 1 - (2-trifluoromethylphenyl) eth-1-yl H
374 1 -(3 -Trifluormethylphenyl)eth- 1 -yl H374 1 - (3-trifluoromethylphenyl) eth-1-yl H
375 1 -(4-Trifluormethylphenyl)eth- 1 -yl H375 1 - (4-trifluoromethylphenyl) eth-1-yl H
376 1 -(2-Methoxyphenyl)eth- 1 -yl H376 1 - (2-methoxyphenyl) eth-1-ylyl H
377 1 -(3 -Methoxyphenyl)eth- 1 -yl H377 1 - (3-Methoxyphenyl) eth-1-yl H
378 1 -(4-Methoxyphenyl)eth- 1 -yl H378 1 - (4-methoxyphenyl) eth-1-ylyl H
379 (4-Chloropyridin-2-yl)methyl H379 (4-chloropyridin-2-yl) methyl H
380 (3 -Chloropyridin-4-yl)methyl H380 (3-chloropyridin-4-yl) methyl H
381 (2-Chloropyridin-3 -yl)methyl H381 (2-chloropyridin-3-yl) methyl H
382 (2-Chloropyridin-4-yl)methyl H382 (2-chloropyridin-4-yl) methyl H
383 (2,6-Difluorphenyl)methyl H383 (2,6-difluorophenyl) methyl H
384 (2,3-Difluorphenyl)methyl H384 (2,3-difluorophenyl) methyl H
385 (5-Chlorpyrazin-2-yl)methyl H385 (5-chloropyrazine-2-yl) methyl H
386 (2-Chlorpyrimidin-5-yl)methyl H386 (2-chloropyrimidin-5-yl) methyl H
387 1 -Benzofuran-5-ylmethyl H387 1-benzofuran-5-ylmethyl H
388 Cyclopropyl(phenyl)methyl H388 cyclopropyl (phenyl) methyl H
389 Cyclopropyl(4-chlorphenyl)methyl H389 cyclopropyl (4-chlorophenyl) methyl H
390 Cyclopropyl(4-methylphenyl)methyl H390 cyclopropyl (4-methylphenyl) methyl H
391 Cyclopropyl(4-cyanophenyl)methyl H391 Cyclopropyl (4-cyanophenyl) methyl H
392 Cyclopropyl(4 - fluorphenyl)methyl H392 Cyclopropyl (4-fluorophenyl) methyl H
393 Indan- 5 -y lmethy 1 H393 indane 5 -y lmethy 1 H
394 (2 ,4, 6-Trimethylphenyl)methyl H No. R5 R6 394 (2, 4, 6-trimethylphenyl) methyl H No. R 5 R 6
395 (2,6-Dichlor-4-methylphenyl)methyl H395 (2,6-dichloro-4-methylphenyl) methyl H
396 1 -(3 -Fluorphenyl)propyl H396 1 - (3-fluorophenyl) propyl H
397 1 -(4-Fluorphenyl)propyl H397 1 - (4-fluorophenyl) propyl H
398 1 -(2-Fluorphenyl)propyl H398 1 - (2-fluorophenyl) propyl H
399 1 -(2-Chlorphenyl)propyl H399 1 - (2-chlorophenyl) propyl H
400 1 -(3-Chlorphenyl)propyl H400 1 - (3-chlorophenyl) propyl H
401 1 -(4-Chlorphenyl)propyl H401 1 - (4-chlorophenyl) propyl H
402 1 -(2-Bromphenyl)propyl H402 1 - (2-bromophenyl) propyl H
403 1 -(3 -Bromphenyl)propyl H403 1 - (3-bromophenyl) propyl H
404 1 -(4-Bromphenyl)propyl H404 1 - (4-bromophenyl) propyl H
405 1 -(2-Cyanophenyl)propyl H405 1 - (2-cyanophenyl) propyl H
406 1 -(3-Cyanophenyl)propyl H406 1 - (3-cyanophenyl) propyl H
407 1 -(4-Cyanophenyl)propyl H407 1 - (4-cyanophenyl) propyl H
408 1 -(2-Trifluormethylphenyl)propyl H408 1 - (2-trifluoromethylphenyl) propyl H
409 1 -(3 -Trifluormethylphenyl)propyl H409 1 - (3-trifluoromethylphenyl) propyl H
410 1 -(4-Trifluormethylphenyl)propyl H410 1 - (4-trifluoromethylphenyl) propyl H
411 1 -(2-Methoxyphenyl)propyl H411 1 - (2-methoxyphenyl) propyl H
412 1 -(3 -Methoxyphenyl)propyl H412 1 - (3-Methoxyphenyl) propyl H
413 1 -(4-Methoxyphenyl)propyl H413 1 - (4-methoxyphenyl) propyl H
414 1 -(2-Methylphenyl)propyl H414 1 - (2-methylphenyl) propyl H
415 1 -(3 -Methylphenyl)propyl H415 1 - (3-methylphenyl) propyl H
416 1 -(4-Methylphenyl)propyl H416 1 - (4-methylphenyl) propyl H
417 1 -(2,4-dimethylphenyl)ethyl H417 1 - (2,4-dimethylphenyl) ethyl H
418 1 -(4-ethylphenyl)ethyl H418 1 - (4-ethylphenyl) ethyl H
419 1 -(3 ,4-Dimethylphenyl)ethyl H419 1 - (3,4-dimethylphenyl) ethyl H
420 1 -(2,5-Dimethylphenyl)ethyl H420 1 - (2,5-dimethylphenyl) ethyl H
421 l-(Phenyl)butyl H421 l- (phenyl) butyl H
422 2-Methyl- 1 -(Phenyl)propyl H422 2-methyl-1 - (phenyl) propyl H
423 (2,4,5-Trimethylphenyl)methyl H423 (2,4,5-trimethylphenyl) methyl H
424 (5-Cyano-2-fluorphenyl)methyl H424 (5-cyano-2-fluorophenyl) methyl H
425 (4-Cyano-2-fluorphenyl)methyl H425 (4-cyano-2-fluorophenyl) methyl H
426 (2-Cyano-4-fluorphenyl)methyl H426 (2-cyano-4-fluorophenyl) methyl H
427 (2-Cyano-5-fluorphenyl)methyl H427 (2-cyano-5-fluorophenyl) methyl H
428 4-(Dimethylamino)phenylmethyl H428 4- (dimethylamino) phenylmethyl H
429 3 -(Dimethylamino)phenylmethyl H No. R5 R6 429 3 - (dimethylamino) phenylmethyl H No. R 5 R 6
430 B enzo [1,3] dioxol-5 -yl-methyl H430 B enzo [1,3] dioxol-5-ylmethyl H
431 4-(Methoxymethyl)phenylmethyl H431 4- (methoxymethyl) phenylmethyl H
432 3 -(Methoxymethyl)phenylmethyl H432 3 - (methoxymethyl) phenylmethyl H
433 2-(Methoxymethyl)phenylmethyl H433 2- (methoxymethyl) phenylmethyl H
434 (2-Methoxy-5-methyl-phenyl)methyl H434 (2-methoxy-5-methylphenyl) methyl H
435 (3 -Fluor-4-methoxyphenyl)methyl H435 (3-fluoro-4-methoxyphenyl) methyl H
436 (2-Fluor-4-methoxyphenyl)methyl H436 (2-fluoro-4-methoxyphenyl) methyl H
437 (2-Fluor-5-methoxyphenyl)methyl H437 (2-fluoro-5-methoxyphenyl) methyl H
438 1 -(2,6-Difluorphenyl)ethyl H438 1 - (2,6-Difluorophenyl) ethyl H
439 1 -(2,5-Difluorphenyl)ethyl H439 1 - (2,5-difluorophenyl) ethyl H
440 1 -(2,4-Difluorphenyl)ethyl H440 1 - (2,4-difluorophenyl) ethyl H
441 1 -(2,6-Dichlorphenyl)ethyl H441 1 - (2,6-dichlorophenyl) ethyl H
442 1 -(2,5-Dichlorphenyl)ethyl H442 1 - (2,5-dichlorophenyl) ethyl H
443 1 -(2,4-Dichlorphenyl)ethyl H443 1 - (2,4-dichlorophenyl) ethyl H
444 1 -(2,3-Dichlorphenyl)ethyl H444 1 - (2,3-dichlorophenyl) ethyl H
445 1 -(3,5-Dichlorphenyl)ethyl H445 1 - (3,5-dichlorophenyl) ethyl H
446 2-Naphthylmethyl H446 2-naphthylmethyl H
447 1 -Naphthylmethyl H447 1 -naphthylmethyl H
448 Chinolin-4-ylmethyl H448 quinolin-4-ylmethyl H
449 Chinolin-6-ylmethyl H449 Quinolin-6-ylmethyl H
450 Chinolin-8-ylmethyl H450 quinolin-8-ylmethyl H
451 Chinolin-2-ylmethyl H451 quinolin-2-ylmethyl H
452 Chinoxalin-2-ylmethyl H452 quinoxalin-2-ylmethyl H
453 (5-Chlor-2-fluorphenyl)methyl H453 (5-chloro-2-fluorophenyl) methyl H
454 (4-Chlor-2-fluorphenyl)methyl H454 (4-chloro-2-fluorophenyl) methyl H
455 (2-Chlor-4-fluorphenyl)methyl H455 (2-chloro-4-fluorophenyl) methyl H
456 (2-Chlor-5-fluorphenyl)methyl H456 (2-chloro-5-fluorophenyl) methyl H
457 (3 -Chlor-2-fluorphenyl)methyl H457 (3-chloro-2-fluorophenyl) methyl H
458 (3 -Chlor-4-fluorphenyl)methyl H458 (3-chloro-4-fluorophenyl) methyl H
459 (3-Chlor-5-fluorphenyl)methyl H459 (3-chloro-5-fluorophenyl) methyl H
460 (4-Chlor-3 -fluorphenyl)methyl H460 (4-chloro-3-fluorophenyl) methyl H
461 (2-Chlor-6-fluorphenyl)methyl H461 (2-chloro-6-fluorophenyl) methyl H
462 (2,4,5-Trifluorphenyl)methyl H462 (2,4,5-trifluorophenyl) methyl H
463 (2 ,4, 6-Trifluorphenyl)methyl H463 (2, 4, 6-trifluorophenyl) methyl H
464 (3 ,4,5-Trifluorphenyl)methyl H No. R5 R6 464 (3, 4,5-trifluorophenyl) methyl H No. R 5 R 6
465 (3 -Cyano-4-methoxyphenyl)methyl H465 (3-cyano-4-methoxyphenyl) methyl H
466 (4-Cyano-3 -methoxyphenyl)methyl H466 (4-cyano-3-methoxyphenyl) methyl H
467 (4-Cyano-2-methoxyphenyl)methyl H467 (4-cyano-2-methoxyphenyl) methyl H
468 (4-Cyclopropoxyphenyl)methyl H468 (4-Cyclopropoxyphenyl) methyl H
469 1 -Benzothiophen-6-ylmethyl H469 1-benzothiophene-6-ylmethyl H
470 1 -Benzothiophen-5-ylmethyl H470 1-benzothiophene-5-ylmethyl H
471 1 -(2,4,5-Trimethylphenyl)ethyl H471 1 - (2,4,5-trimethylphenyl) ethyl H
472 1 -(4-Ethylphenyl)propyl H472 1 - (4-ethylphenyl) propyl H
473 1 -(4-Propan-2-ylphenyl)ethyl H473 1 - (4-propan-2-yl-phenyl) ethyl H
474 3 -Methyl- 1 -phenylbutan- 1 -yl H474 3-methyl-1-phenyl-butan-1-yl H
475 (3 -Acetamidophenyl)methyl H475 (3-acetamidophenyl) methyl H
476 (4-Acetamidophenyl)methyl H476 (4-acetamidophenyl) methyl H
477 [4-(Methylcarbamoyl)phenyl)methyl H477 [4- (methylcarbamoyl) phenyl] methyl H
478 [3-(Methylcarbamoyl)phenyl)methyl H478 [3- (methylcarbamoyl) phenyl] methyl H
479 [4-(Ethylcarbamoyl)phenyl)methyl H479 [4- (ethylcarbamoyl) phenyl] methyl H
480 [3-(Ethylcarbamoyl)phenyl)methyl H480 [3- (ethylcarbamoyl) phenyl] methyl H
481 1 -(2 ,4, 6-Trimethylpyridin- 3 -yl) ethyl H481 1 - (2, 4, 6-trimethylpyridin-3-yl) ethyl H
482 [4-(Propan-2-yloxy)phenyl]methyl H482 [4- (propan-2-yloxy) phenyl] methyl H
483 [3-(Propan-2-yloxy)phenyl]methyl H483 [3- (propan-2-yloxy) phenyl] methyl H
484 (2-Methyl-6-nitrophenyl)methyl H484 (2-methyl-6-nitrophenyl) methyl H
485 (4-Methyl-3 -nitrophenyl)methyl H485 (4-methyl-3-nitrophenyl) methyl H
486 (2-Methyl-3 -nitrophenyl)methyl H486 (2-methyl-3-nitrophenyl) methyl H
487 (2-Methyl-4-nitrophenyl)methyl H487 (2-methyl-4-nitrophenyl) methyl H
488 2-(2-Nitrophenyl)eth- 1 -yl H488 2- (2-Nitrophenyl) eth-1-yl H
489 2-(3 -Nitrophenyl)eth- 1 -yl H489 2- (3-nitrophenyl) eth-1-yl H
490 2-(4-Nitrophenyl)eth- 1 -yl H490 2- (4-Nitrophenyl) eth-1-yl H
491 (3 ,4-Dimethoxyphenyl)methyl H491 (3,4-dimethoxyphenyl) methyl H
492 (4-Methoxy-3,5-dimethylpyridin-2-yl)methyl H492 (4-methoxy-3,5-dimethylpyridin-2-yl) methyl H
493 (4,5-Dimethoxypyridin-2-yl)methyl H493 (4,5-dimethoxypyridin-2-yl) methyl H
494 1 -(2-Naphthyl)methyl H494 1 - (2-naphthyl) methyl H
495 1 -( 1 -Naphthyl)methyl H495 1 - (1-naphthyl) methyl H
496 (3 -Chlor-4-methoxyphenyl)methyl H496 (3-chloro-4-methoxyphenyl) methyl H
497 (4-Chlor-3 -methoxyphenyl)methyl H497 (4-chloro-3-methoxyphenyl) methyl H
498 (4-Chlor-2-methoxyphenyl)methyl H498 (4-chloro-2-methoxyphenyl) methyl H
499 (5-Chlor-2-methoxyphenyl)methyl H No. R5 R6 499 (5-chloro-2-methoxyphenyl) methyl H No. R 5 R 6
500 (3-Chlor-5-methoxyphenyl)methyl H500 (3-chloro-5-methoxyphenyl) methyl H
501 (2-Methylchinolin-4-yl)methyl H501 (2-methylquinolin-4-yl) methyl H
502 2-(5-Chlor-2-fluorphenyl)eth- 1 -yl H502 2- (5-chloro-2-fluorophenyl) eth-1-yl H
503 2-(4-Chlor-2-fluorphenyl)eth- 1 -yl H503 2- (4-chloro-2-fluorophenyl) eth-1-yl H
504 2-(2-Chlor-4-fluorphenyl)eth- 1 -yl H504 2- (2-chloro-4-fluorophenyl) eth-1-yl H
505 2-(2-Chlor-5-fluorphenyl)eth- 1 -yl H505 2- (2-chloro-5-fluorophenyl) eth-1-yl H
506 2-(3-Chlor-2-fluorphenyl)eth- 1 -yl H506 2- (3-chloro-2-fluorophenyl) eth-1-yl H
507 2-(3-Chlor-4-fluorphenyl)eth- 1 -yl H507 2- (3-chloro-4-fluorophenyl) eth-1-yl H
508 2-(3-Chlor-5-fluorphenyl)eth- 1 -yl H508 2- (3-chloro-5-fluorophenyl) eth-1-yl H
509 2-(4-Chlor-3-fluorphenyl)eth- 1 -yl H509 2- (4-chloro-3-fluorophenyl) eth-1-yl H
510 2-(2-Chlor-6-fluorphenyl)eth- 1 -yl H510 2- (2-chloro-6-fluorophenyl) eth-1-yl H
511 (2-Hydroxychinolin-3 -yl)methyl H511 (2-hydroxyquinolin-3-yl) methyl H
512 l-(5,6,7,8-Tetrahydronaphthalin-2-yl)ethyl H512 l- (5,6,7,8-tetrahydronaphthalen-2-yl) ethyl H
513 [5-(Trifluormethyl)pyridin-2-yl]methyl H513 [5- (trifluoromethyl) pyridin-2-yl] methyl H
514 [2-(Trifluormethyl)pyridin-4-yl]methyl H514 [2- (trifluoromethyl) pyridin-4-yl] methyl H
515 (3,6-Dichlorpyridin-2-yl)methyl H515 (3,6-dichloropyridin-2-yl) methyl H
516 [5-(Trifluormethyl)pyrazin-2-yl]methyl H516 [5- (trifluoromethyl) pyrazin-2-yl] methyl H
517 [2-(Trifluormethyl)pyrimidin-2-yl]methyl H517 [2- (trifluoromethyl) pyrimidin-2-yl] methyl H
518 1 -Phenylhexan- 1 -yl H518 1 -phenylhexan-1-yl-H
519 1 -(3 -tert-Butylphenyl)ethyl H519 1 - (3-tert-butylphenyl) ethyl H
520 1 -(4-tert-Butylphenyl)ethyl H520 1 - (4-tert-butylphenyl) ethyl H
521 1 -(2-Nitrophenyl)propyl H521 1 - (2-Nitrophenyl) propyl H
522 1 -(3 -Nitrophenyl)propyl H522 1 - (3-nitrophenyl) propyl H
523 1 -(4-Nitrophenyl)propyl H523 1 - (4-Nitrophenyl) propyl H
524 (2-Methoxy-5-nitrophenyl)methyl H524 (2-methoxy-5-nitrophenyl) methyl H
525 (4-Methoxy-3 -nitrophenyl)methyl H525 (4-methoxy-3-nitrophenyl) methyl H
526 (2-Methoxy-4-nitrophenyl)methyl H526 (2-methoxy-4-nitrophenyl) methyl H
527 (3 -Methoxy-4-nitrophenyl)methyl H527 (3-methoxy-4-nitrophenyl) methyl H
528 Diphenylmethyl H528 diphenylmethyl H
529 (4-Phenylphenyl)methyl H529 (4-phenylphenyl) methyl H
530 Phenyl(pyridin-2-yl)methyl H530 phenyl (pyridin-2-yl) methyl H
531 Phenyl(pyridin-3 -yl)methyl H531 phenyl (pyridin-3-yl) methyl H
532 Phenyl(pyridin-4-yl)methyl H532 phenyl (pyridin-4-yl) methyl H
533 (5-Chlor-2-Ethoxyphenyl)methyl H533 (5-chloro-2-ethoxyphenyl) methyl H
534 (5-Chlor-2-nitrophenyl)methyl H No. R5 R6 534 (5-chloro-2-nitrophenyl) methyl H No. R 5 R 6
535 (4-Chlor-2-nitrophenyl)methyl H535 (4-chloro-2-nitrophenyl) methyl H
536 (2-Chlor-4-nitrophenyl)methyl H536 (2-chloro-4-nitrophenyl) methyl H
537 (2-Chlor-5-nitrophenyl)methyl H537 (2-chloro-5-nitrophenyl) methyl H
538 (3 -Chlor-2-nitrophenyl)methyl H538 (3-chloro-2-nitrophenyl) methyl H
539 (3 -Chlor-4-nitrophenyl)methyl H539 (3-chloro-4-nitrophenyl) methyl H
540 (3-Chlor-5-nitrophenyl)methyl H540 (3-chloro-5-nitrophenyl) methyl H
541 (4-Chlor-3 -nitrophenyl)methyl H541 (4-chloro-3-nitrophenyl) methyl H
542 (2-Chlor-6-nitrophenyl)methyl H542 (2-chloro-6-nitrophenyl) methyl H
543 (5-Brompyridin-2-yl)methyl H543 (5-bromopyridin-2-yl) methyl H
544 (2-Brompyridin-4-yl)methyl H544 (2-bromopyridin-4-yl) methyl H
545 (6-Brompyridin-2-yl)methyl H545 (6-bromopyridin-2-yl) methyl H
546 (2,4-Difluor-5-nitrophenyl)methyl H546 (2,4-difluoro-5-nitrophenyl) methyl H
547 (3-Methyl-2-trifluormethylphenyl)methyl H547 (3-methyl-2-trifluoromethylphenyl) methyl H
548 3,3,3 -Trifluor- 1 -phenylpropyl H548,3,3,3-trifluoro-1-phenylpropyl H
549 Cyclohexyl(phenyl)methyl H549 cyclohexyl (phenyl) methyl H
550 Cyclopentyl(phenyl)methyl H550 cyclopentyl (phenyl) methyl H
551 1 -(3,4-Dichlorphenyl)ethyl H551 1 - (3,4-dichlorophenyl) ethyl H
552 [4-(Cyclopentyloxy)phenyl]methyl H552 [4- (cyclopentyloxy) phenyl] methyl H
553 [2-Fluor-4-(trifluormethyl)phenyl]methyl H553 [2-Fluoro-4- (trifluoromethyl) phenyl] methyl H
554 [3-Fluor-4-(trifluormethyl)phenyl]methyl H554 [3-Fluoro-4- (trifluoromethyl) phenyl] methyl H
555 [2-Fluor-5-(trifluormethyl)phenyl]methyl H555 [2-fluoro-5- (trifluoromethyl) phenyl] methyl H
556 [3-Fluor-5-(trifluormethyl)phenyl]methyl H556 [3-fluoro-5- (trifluoromethyl) phenyl] methyl H
557 1 -(2-Nitrophenyl)butyl H557 1 - (2-Nitrophenyl) butyl H
558 1 -(3 -Nitrophenyl)butyl H558 1 - (3-nitrophenyl) butyl H
559 1 -(4-Nitrophenyl)butyl H559 1 - (4-Nitrophenyl) butyl H
560 1 -(2-Cyanophenyl)butyl H560 1 - (2-cyanophenyl) butyl H
561 1 -(3-Cyanohenyl)butyl H561 1 - (3-cyanohenyl) butyl H
562 1 -(4-Cyanophenyl)butyl H562 1 - (4-cyanophenyl) butyl H
563 1 -(2-Fluorphenyl)butyl H563 1 - (2-fluorophenyl) butyl H
564 1 -(3 -Fluorphenyl)butyl H564 1 - (3-fluorophenyl) butyl H
565 1 -(4-Fluorphenyl)butyl H565 1 - (4-fluorophenyl) butyl H
566 1 -(2-Chlorphenyl)butyl H566 1 - (2-chlorophenyl) butyl H
567 1 -(3-Chlorphenyl)butyl H567 1 - (3-chlorophenyl) butyl H
568 1 -(4-Chlorphenyl)butyl H568 1 - (4-chlorophenyl) butyl H
569 (2,4-Dinitrophenyl)methyl H No. R5 R6 569 (2,4-dinitrophenyl) methyl H No. R 5 R 6
570 (2-Methylphenyl)(phenyl)methyl H570 (2-methylphenyl) (phenyl) methyl H
571 1 ,2-Diphenylethyl H571 1, 2-diphenylethyl H
572 1 -(4-Phenylphenyl)ethyl H572 1 - (4-phenylphenyl) ethyl H
573 (4-Brom-3 -methylphenyl)methyl H573 (4-bromo-3-methylphenyl) methyl H
574 (4-Brom-3 -fluorphenyl)methyl H574 (4-bromo-3-fluorophenyl) methyl H
575 (4-Brom-3 -chlorphenyl)methyl H575 (4-bromo-3-chlorophenyl) methyl H
576 (3 -Brom-4-chlorphenyl)methyl H576 (3-Bromo-4-chlorophenyl) methyl H
577 (3-Brom-5-chlorphenyl)methyl H577 (3-bromo-5-chlorophenyl) methyl H
578 4-Brom-3 -methylphenyl H578 4-bromo-3-methylphenyl H
579 4-Brom-3 -fluorphenyl H579 4-bromo-3-fluorophenyl H
580 4-Brom-3 -chlorphenyl H580 4-bromo-3-chlorophenyl H
581 3 -Brom-4-chlorphenyl H581 3 -bromo-4-chlorophenyl H
582 3-Brom-5-chlorphenyl H582 3-bromo-5-chlorophenyl H
583 4-Brom-2-fluorphenyl H583 4-bromo-2-fluorophenyl H
584 (5-Brom-2-fluorphenyl)methyl H584 (5-bromo-2-fluorophenyl) methyl H
585 (2-Brom-4-fluorphenyl)methyl H585 (2-bromo-4-fluorophenyl) methyl H
586 (4-Brom-2-fluorphenyl)methyl H586 (4-bromo-2-fluorophenyl) methyl H
587 (3-Brom-5-fluorphenyl)methyl H587 (3-bromo-5-fluorophenyl) methyl H
588 5-Brom-2-fluorphenyl H588 5-bromo-2-fluorophenyl H
589 2-Brom-4-fluorphenyl H589 2-bromo-4-fluorophenyl H
590 3-Brom-5-fluorphenyl H590 3-bromo-5-fluorophenyl H
591 1 -(2,4-Dichlorphenyl)propyl H591 1 - (2,4-dichlorophenyl) propyl H
592 1 -(3 ,4-Dichlorphenyl)propyl H592 1 - (3, 4-dichlorophenyl) propyl H
593 l-(2,6-Dichlor-3-fluorphenyl)ethyl H593 l- (2,6-dichloro-3-fluorophenyl) ethyl H
594 l-(2,4-Dichlor-5-fluorphenyl)ethyl H594 l- (2,4-dichloro-5-fluorophenyl) ethyl H
595 (2-Chlor-6-Trifluormethylphenyl)methyl H595 (2-chloro-6-trifluoromethylphenyl) methyl H
596 (2-Chlor-4-Trifluormethylphenyl)methyl H596 (2-chloro-4-trifluoromethylphenyl) methyl H
597 (4-Chlor-3-Trifluormethylphenyl)methyl H597 (4-chloro-3-trifluoromethylphenyl) methyl H
598 (2-Chlor-4-Trifluormethylphenyl)methyl H598 (2-chloro-4-trifluoromethylphenyl) methyl H
599 (3 -Brom-4-Methoxyphenyl)methyl H599 (3-Bromo-4-methoxyphenyl) methyl H
600 4-Brom-3 -Methoxyphenyl H600 4-bromo-3-methoxyphenyl H
601 4-Ethylphenyl H601 4-ethylphenyl H
602 4-n-Propylphenyl H602 4-n-Propylphenyl H
603 4-iso-Propylphenyl H603 4-iso-propylphenyl H
604 4-Cyclopropylphenyl H No. R5 R6 604 4-Cyclopropylphenyl H No. R 5 R 6
605 4-n-Butylphenyl H605 4-n-butylphenyl H
606 Thiophen-2-yl H606 thiophen-2-yl H
607 Thiophen-3-yl H607 thiophen-3-yl H
608 5-Methylthiophen-2-yl H608 5-Methylthiophene-2-yl H
609 5-Ethylthiophen-2-yl H609 5-ethylthiophene-2-yl H
610 5-Chlorthiophen-2-yl H610 5-chlorothiophene-2-yl H
611 5-Bromthiophen-2-yl H611 5-bromothiophene-2-yl H
612 4-Methylthiophen-2-yl H612 4-methylthiophene-2-yl H
613 3 -Methylthiophen-2-yl H613 3-methylthiophene-2-yl H
614 5-Fluorthiophen-3-yl H614 5-fluorothiophen-3-yl H
615 3,5-Dimethylthiophen-2-yl H615 3,5-dimethylthiophene-2-yl H
616 3 -Ethylthiophen-2-yl H616 3 -ethylthiophene-2-yl H
617 4,5-Dimethylthiophen-2-yl H617 4,5-dimethylthiophene-2-yl H
618 3 ,4-Dimethylthiophen-2-yl H618,3,4-dimethylthiophene-2-yl H
619 4-Chlorthiophen-2-yl H619 4-chlorothiophene-2-yl H
620 5-Ethyl-4-methylthiophen-2-yl H620 5-ethyl-4-methylthiophene-2-yl H
621 5-Propylthiophen-2-yl H621 5-Propylthiophene-2-yl H
622 5-Nitrothiophen-2-yl H622 5-Nitrothiophene-2-yl H
623 3 -Nitrothiophen-2-yl H623 3 -Nitrothiophene-2-yl H
624 4-Nitrothiophen-2-yl H624 4-Nitrothiophene-2-yl H
625 5-n-Butylthiophen-2-yl H625 5-n-butylthiophene-2-yl H
626 5-tert-Butylthiophen-2-yl H626 5-tert-butylthiophene-2-yl H
627 5-iso-Butylthiophen-2-yl H627 5-iso-butylthiophene-2-yl H
628 5-(2-methoxyethyl)-thiophen-2-yl H628 5- (2-methoxyethyl) -thiophen-2-yl H
629 3-(2-methoxyethyl)-thiophen-2-yl H629 3- (2-methoxyethyl) -thiophen-2-yl H
630 2,3-Dichlorthiophen-2-yl H630 2,3-dichlorothiophen-2-yl H
631 3-(l,2-Oxazol-3-yl)thiophen-2-yl H631 3- (1,2-oxazol-3-yl) thiophen-2-yl H
632 4-(l,2-Oxazol-5-yl)thiophen-2-yl H632 4- (1,2-oxazol-5-yl) thiophen-2-yl H
633 5-(l,3-Oxazol-5-yl)thiophen-2-yl H633 5- (1,3-oxazol-5-yl) thiophen-2-yl H
634 3,4-Dichlorthiophen-2-yl H634 3,4-dichlorothiophen-2-yl H
635 5-(2-Pyridyl)thiophen-2-yl H635 5- (2-pyridyl) thiophen-2-yl H
636 4-iso-Butylphenyl H636 4-iso-butylphenyl H
637 5 -n-Pentylphenyl H637 5 -n-pentylphenyl H
638 4-tert-Butylphenyl H638 4-tert-butylphenyl H
639 5-iso-Pentylphenyl H No. R5 R6 639 5-iso-pentylphenyl H No. R 5 R 6
640 5-neo-Pentylphenyl H  640 5-neo-pentylphenyl H
641 Furan-2-yl H  641 Furan-2-yl H
642 5-Methylfuran-2-yl H  642 5-methylfuran-2-yl H
643 5-Ethylfuran-2-yl H  643 5-ethyl-furan-2-yl H
644 5-Methoxycarbonylfuran-2-yl H  644 5-Methoxycarbonyl-furan-2-yl H
645 5-Chlorfüran-2-yl H  645 5-chlorofuran-2-yl H
646 5-Bromfüran-2-yl H  646 5-Bromofuran-2-yl H
647 n-Pentyl H  647 n-pentyl H
648 n-Hexyl H  648 n-hexyl H
649 n-Heptyl H  649 n-heptyl H
650 n-Octyl H  650 n-octyl H
Figure imgf000088_0001
Figure imgf000088_0001
Tabelle 1.2: Bevorzugt für die Verwendung von Verbindungen der Formel (1.2) sind die Verbindungen 1.2-1 bis 1.2-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.2-1 bis 1.2-650 der Tabelle 1.2 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Table 1.2: Preferred for the use of compounds of formula (1.2) are the compounds 1.2-1 to 1.2-650, wherein R 5 and R 6 have the meanings given in the respective line of Table 1. The compounds 1.2-1 to 1.2-650 of Table 1.2 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000088_0002
Figure imgf000088_0002
Tabelle 1.3: Bevorzugt für die Verwendung von Verbindungen der Formel (1.3) sind die Verbindungen 1.3-1 bis 1.3-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.3-1 bis 1.3-650 der Tabelle 1.3 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Table 1.3: Preferred for the use of compounds of formula (1.3) are the compounds 1.3-1 to 1.3-650, wherein R 5 and R 6 have the meanings of Table 1 given in the respective line. The compounds 1.3-1 to 1.3-650 of Table 1.3 are thus determined by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000088_0003
Tabelle 1.4: Bevorzugt für die Verwendung von Verbindungen der Formel (1.4) sind die Verbindungen 1.4-1 bis 1.4-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.4-1 bis 1.4-650 der Tabelle 1.4 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000088_0003
Preferred compounds for use of compounds of the formula (1.4) are the compounds 1.4-1 to 1.4-650, in which R 5 and R 6 have the meanings of Table 1 given in the respective line. The compounds 1.4-1 to 1.4-650 of Table 1.4 are thus by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000089_0001
Figure imgf000089_0001
Tabelle 1.5: Bevorzugt für die Verwendung von Verbindungen der Formel (1.5) sind die Verbindungen 1.5-1 bis 1.5-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.5-1 bis 1.5-650 der Tabelle 1.5 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Table 1.5: Preferred for the use of compounds of formula (1.5) are the compounds 1.5-1 to 1.5-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.5-1 to 1.5-650 of Table 1.5 are thus by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000089_0002
Figure imgf000089_0002
Tabelle 1.6: Bevorzugt für die Verwendung von Verbindungen der Formel (1.6) sind die Verbindungen 1.6-1 bis 1.6-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.6-1 bis 1.6-650 der Tabelle 1.6 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Table 1.6: Preferred for the use of compounds of formula (1.6) are the compounds 1.6-1 to 1.6-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.6-1 to 1.6-650 of Table 1.6 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000089_0003
Figure imgf000089_0003
Tabelle 1.7: Bevorzugt für die Verwendung von Verbindungen der Formel (1.7) sind die Verbindungen 1.7-1 bis 1.7-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.7-1 bis 1.7-650 der Tabelle 1.7 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000090_0001
Table 1.7: Preferred for the use of compounds of formula (1.7) are the compounds 1.7-1 to 1.7-650, wherein R 5 and R 6 have the meanings of Table 1 given in the respective line. The compounds 1.7-1 to 1.7-650 of Table 1.7 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000090_0001
Tabelle 1.8: Bevorzugt für die Verwendung von Verbindungen der Formel (1.8) sind die Verbindungen 1.8-1 bis 1.8-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.8-1 bis 1.8-650 der Tabelle 1.8 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Table 1.8: Preferred for the use of compounds of formula (1.8) are the compounds 1.8-1 to 1.8-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.8-1 to 1.8-650 of Table 1.8 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000090_0002
Tabelle 1.9: Bevorzugt für die Verwendung von Verbindungen der Formel (1.9) sind die Verbindungen 1.9-1 bis 1.9-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.9-1 bis 1.9-650 der Tabelle 1.9 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000090_0002
Table 1.9: Preferred for the use of compounds of formula (1.9) are the compounds 1.9-1 to 1.9-650, wherein R 5 and R 6 have the meanings of Table 1 given in the respective line. The compounds 1.9-1 to 1.9-650 of Table 1.9 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000090_0003
Figure imgf000090_0003
Tabelle 1.10: Bevorzugt für die Verwendung von Verbindungen der Formel (1.10) sind die Table 1.10: Preferred for the use of compounds of the formula (1.10) are the
Verbindungen 1.10-1 bis 1.10-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Compounds 1.10-1 to 1.10-650, wherein R 5 and R 6 are as indicated in the respective line
Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.10-1 bis 1.10-650 der Tabelle 1.10 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Meanings of Table 1 have. The compounds 1.10-1 to 1.10-650 of Table 1.10 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000090_0004
Figure imgf000090_0004
Tabelle 1.11 : Bevorzugt für die Verwendung von Verbindungen der Formel (1.11) sind die Table 1.11: Preferred for the use of compounds of the formula (1.11) are the
Verbindungen L I 1-1 bis L I 1-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.11-1 bis L I 1-650 der Tabelle 1.11 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds LI 1-1 to LI 1-650, wherein R 5 and R 6 are as indicated in the respective line Meanings of Table 1 have. The compounds 1.11-1 to LI 1-650 of Table 1.11 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000091_0001
Figure imgf000091_0001
Tabelle 1.12: Bevorzugt für die Verwendung von Verbindungen der Formel (1.12) sind die Table 1.12: Preferred for the use of compounds of formula (1.12) are the
Verbindungen 1.12-1 bis 1.12-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.12-1 bis 1.12-650 der Tabelle 1.12 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.12-1 to 1.12-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.12-1 to 1.12-650 of Table 1.12 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000091_0002
Figure imgf000091_0002
Tabelle 1.13: Bevorzugt für die Verwendung von Verbindungen der Formel (1.13) sind die Table 1.13: Preferred for the use of compounds of the formula (1.13) are the
Verbindungen 1.13-1 bis 1.13-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.13-1 bis 1.13-650 der Tabelle 1.13 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.13-1 to 1.13-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.13-1 to 1.13-650 of Table 1.13 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000091_0003
Figure imgf000091_0003
Tabelle 1.14: Bevorzugt für die Verwendung von Verbindungen der Formel (1.14) sind die Table 1.14: Preferred for the use of compounds of formula (1.14) are the
Verbindungen 1.14-1 bis 1.14-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.14-1 bis 1.14-650 der Tabelle 1.14 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.14-1 to 1.14-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.14-1 to 1.14-650 of Table 1.14 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
(1.15)(1.15)
Figure imgf000091_0004
Tabelle 1.15: Bevorzugt für die Verwendung von Verbindungen der Formel (1.15) sind die
Figure imgf000091_0004
Table 1.15: Preferred for the use of compounds of the formula (1.15) are the
Verbindungen 1.15-1 bis 1.15-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.15- 1 bis 1.15-650 der Tabelle 1.15 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.15-1 to 1.15-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.15- 1 to 1.15-650 of Table 1.15 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000092_0001
Figure imgf000092_0001
Tabelle 1.16: Bevorzugt für die Verwendung von Verbindungen der Formel (1.16) sind die Table 1.16: Preferred for the use of compounds of the formula (1.16) are the
Verbindungen 1.16-1 bis 1.16-650, worin R5 und R6 die in der jeweiligen Zeile angegebenenCompounds 1.16-1 to 1.16-650, wherein R 5 and R 6 are as indicated in the respective line
Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.16-1 bis 1.16-650 der Tabelle 1.16 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Meanings of Table 1 have. The compounds 1.16-1 to 1.16-650 of Table 1.16 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000092_0002
Figure imgf000092_0002
Tabelle 1.17: Bevorzugt für die Verwendung von Verbindungen der Formel (1.17) sind die Table 1.17: Preferred for the use of compounds of formula (1.17) are the
Verbindungen 1.17-1 bis 1.17-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.17-1 bis 1.17-650 der Tabelle 1.17 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.17-1 to 1.17-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.17-1 to 1.17-650 of Table 1.17 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000092_0003
Figure imgf000092_0003
Tabelle 1.18: Bevorzugt für die Verwendung von Verbindungen der Formel (1.18) sind die Table 1.18: Preferred for the use of compounds of the formula (1.18) are the
Verbindungen 1.18-1 bis 1.18-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.18-1 bis 1.18-650 der Tabelle 1.18 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000093_0001
Compounds 1.18-1 to 1.18-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.18-1 to 1.18-650 of Table 1.18 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000093_0001
Tabelle 1.19: Bevorzugt für die Verwendung von Verbindungen der Formel (1.19) sind die Table 1.19: Preferred for the use of compounds of the formula (1.19) are the
Verbindungen 1.19-1 bis 1.19-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.19-1 bis 1.19-650 der Tabelle 1.19 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.19-1 to 1.19-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.19-1 to 1.19-650 of Table 1.19 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000093_0002
Tabelle 1.20: Bevorzugt für die Verwendung von Verbindungen der Formel (1.20) sind die
Figure imgf000093_0002
Table 1.20: Preferred for the use of compounds of the formula (1.20) are the
Verbindungen 1.20-1 bis 1.20-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.20-1 bis 1.20-650 der Tabelle 1.20 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.20-1 to 1.20-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.20-1 to 1.20-650 of Table 1.20 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000093_0003
Figure imgf000093_0003
Tabelle 1.21 : Bevorzugt für die Verwendung von Verbindungen der Formel (1.21) sind die Table 1.21: Preferred for the use of compounds of formula (1.21) are the
Verbindungen 1.21-1 bis 1.21-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.21-1 bis 1.21-650 der Tabelle 1.21 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.21-1 to 1.21-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.21-1 to 1.21-650 of Table 1.21 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
(1.22)(1.22)
Figure imgf000093_0004
Tabelle 1.22: Bevorzugt für die Verwendung von Verbindungen der Formel (1.22) sind die Verbindungen 1.22-1 bis 1.22-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.22-1 bis 1.22-650 der Tabelle 1.22 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000093_0004
Table 1.22: Preferred for the use of compounds of the formula (1.22) are the compounds 1.22-1 to 1.22-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.22-1 to 1.22-650 of Table 1.22 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000094_0001
Figure imgf000094_0001
Tabelle 1.23: Bevorzugt für die Verwendung von Verbindungen der Formel (1.23) sind die Table 1.23: Preferred for the use of compounds of the formula (1.23) are the
Verbindungen 1.23-1 bis 1.23-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.23-1 bis 1.23-650 der Tabelle 1.23 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.23-1 to 1.23-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.23-1 to 1.23-650 of Table 1.23 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000094_0002
Tabelle 1.24: Bevorzugt für die Verwendung von Verbindungen der Formel (1.24) sind die
Figure imgf000094_0002
Table 1.24: Preferred for the use of compounds of formula (1.24) are the
Verbindungen 1.24-1 bis 1.24-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.24-1 bis 1.24-650 der Tabelle 1.24 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.24-1 to 1.24-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.24-1 to 1.24-650 of Table 1.24 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000094_0003
Figure imgf000094_0003
Tabelle 1.25: Bevorzugt für die Verwendung von Verbindungen der Formel (1.25) sind die Table 1.25: Preferred for the use of compounds of the formula (1.25) are the
Verbindungen 1.25-1 bis 1.25-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.25-1 bis 1.25-650 der Tabelle 1.25 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000095_0001
Compounds 1.25-1 to 1.25-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.25-1 to 1.25-650 of Table 1.25 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000095_0001
Tabelle 1.26: Bevorzugt für die Verwendung von Verbindungen der Formel (1.26) sind die Table 1.26: Preferred for the use of compounds of the formula (1.26) are the
Verbindungen 1.26-1 bis 1.26-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.26-1 bis 1.26-650 der Tabelle 1.26 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.26-1 to 1.26-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.26-1 to 1.26-650 of Table 1.26 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000095_0002
Tabelle 1.27: Bevorzugt für die Verwendung von Verbindungen der Formel (1.27) sind die
Figure imgf000095_0002
Table 1.27: Preferred for the use of compounds of the formula (1.27) are the
Verbindungen 1.27-1 bis 1.27-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.27-1 bis 1.27-650 der Tabelle 1.27 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.27-1 to 1.27-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.27-1 to 1.27-650 of Table 1.27 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000095_0003
Figure imgf000095_0003
Tabelle 1.28: Bevorzugt für die Verwendung von Verbindungen der Formel (1.28) sind die Table 1.28: Preferred for the use of compounds of the formula (1.28) are the
Verbindungen 1.28-1 bis 1.28-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.28-1 bis 1.28-650 der Tabelle 1.28 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.28-1 to 1.28-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.28-1 to 1.28-650 of Table 1.28 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
(1.29)(1.29)
Figure imgf000095_0004
Tabelle 1.29: Bevorzugt für die Verwendung von Verbindungen der Formel (1.29) sind die
Figure imgf000095_0004
Table 1.29: Preferred for the use of compounds of the formula (1.29) are the
Verbindungen 1.29-1 bis 1.29-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.29-1 bis 1.29-650 der Tabelle 1.29 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.29-1 to 1.29-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.29-1 to 1.29-650 of Table 1.29 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000096_0001
Figure imgf000096_0001
Tabelle 1.30: Bevorzugt für die Verwendung von Verbindungen der Formel (1.30) sind die Table 1.30: Preferred for the use of compounds of the formula (1.30) are the
Verbindungen 1.30-1 bis 1.30-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.30-1 bis 1.30-650 der Tabelle 1.30 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.30-1 to 1.30-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.30-1 to 1.30-650 of Table 1.30 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000096_0002
Figure imgf000096_0002
Tabelle 1.31 : Bevorzugt für die Verwendung von Verbindungen der Formel (1.31) sind die Table 1.31: Preferred for the use of compounds of the formula (1.31) are the
Verbindungen 1.31-1 bis 1.31-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.31-1 bis 1.31-650 der Tabelle 1.31 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.31-1 to 1.31-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.31-1 to 1.31-650 of Table 1.31 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000096_0003
Figure imgf000096_0003
Tabelle 1.32: Bevorzugt für die Verwendung von Verbindungen der Formel (1.32) sind die Table 1.32: Preferred for the use of compounds of the formula (1.32) are the
Verbindungen 1.32-1 bis 1.32-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.32-1 bis 1.32-650 der Tabelle 1.32 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000097_0001
Compounds 1.32-1 to 1.32-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.32-1 to 1.32-650 of Table 1.32 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000097_0001
Tabelle 1.33: Bevorzugt für die Verwendung von Verbindungen der Formel (1.33) sind die Table 1.33: Preferred for the use of compounds of the formula (1.33) are the
Verbindungen 1.33-1 bis 1.33-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.33-1 bis 1.33-650 der Tabelle 1.33 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.33-1 to 1.33-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.33-1 to 1.33-650 of Table 1.33 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000097_0002
Tabelle 1.34: Bevorzugt für die Verwendung von Verbindungen der Formel (1.34) sind die
Figure imgf000097_0002
Table 1.34: Preferred for the use of compounds of the formula (1.34) are the
Verbindungen 1.34-1 bis 1.34-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.34-1 bis 1.34-650 der Tabelle 1.34 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.34-1 to 1.34-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.34-1 to 1.34-650 of Table 1.34 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000097_0003
Figure imgf000097_0003
Tabelle 1.35: Bevorzugt für die Verwendung von Verbindungen der Formel (1.35) sind die Table 1.35: Preferred for the use of compounds of the formula (1.35) are the
Verbindungen 1.35-1 bis 1.35-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.35-1 bis 1.35-650 der Tabelle 1.35 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.35-1 to 1.35-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.35-1 to 1.35-650 of Table 1.35 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000097_0004
Tabelle 1.36: Bevorzugt für die Verwendung von Verbindungen der Formel (1.36) sind die Verbindungen 1.36-1 bis 1.36-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.36-1 bis 1.36-650 der Tabelle 1.36 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000097_0004
Table 1.36: Preferred for the use of compounds of the formula (1.36) are the compounds 1.36-1 to 1.36-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.36-1 to 1.36-650 of Table 1.36 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000098_0001
Figure imgf000098_0001
Tabelle 1.37: Bevorzugt für die Verwendung von Verbindungen der Formel (1.37) sind die Table 1.37: Preferred for the use of compounds of formula (1.37) are the
Verbindungen 1.37-1 bis 1.37-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.37-1 bis 1.37-650 der Tabelle 1.37 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.37-1 to 1.37-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.37-1 to 1.37-650 of Table 1.37 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000098_0002
Tabelle 1.38: Bevorzugt für die Verwendung von Verbindungen der Formel (1.38) sind die
Figure imgf000098_0002
Table 1.38: Preferred for the use of compounds of the formula (1.38) are the
Verbindungen 1.38-1 bis 1.38-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.38-1 bis 1.38-650 der Tabelle 1.38 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.38-1 to 1.38-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.38-1 to 1.38-650 of Table 1.38 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000098_0003
Figure imgf000098_0003
Tabelle 1.39: Bevorzugt für die Verwendung von Verbindungen der Formel (1.39) sind die Table 1.39: Preferred for the use of compounds of formula (1.39) are the
Verbindungen 1.39-1 bis 1.39-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.39-1 bis 1.39-650 der Tabelle 1.39 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000099_0001
Compounds 1.39-1 to 1.39-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.39-1 to 1.39-650 of Table 1.39 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000099_0001
Tabelle 1.40: Bevorzugt für die Verwendung von Verbindungen der Formel (1.40) sind die Table 1.40: Preferred for the use of compounds of the formula (1.40) are the
Verbindungen 1.40-1 bis 1.40-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.40-1 bis 1.40-650 der Tabelle 1.40 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.40-1 to 1.40-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.40-1 to 1.40-650 of Table 1.40 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000099_0002
Tabelle 1.41 : Bevorzugt für die Verwendung von Verbindungen der Formel (1.41) sind die
Figure imgf000099_0002
Table 1.41: Preferred for the use of compounds of the formula (1.41) are the
Verbindungen 1.41-1 bis 1.41-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.41-1 bis 1.41-650 der Tabelle 1.41 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.41-1 to 1.41-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.41-1 to 1.41-650 of Table 1.41 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000099_0003
Figure imgf000099_0003
Tabelle 1.42: Bevorzugt für die Verwendung von Verbindungen der Formel (1.42) sind die Table 1.42: Preferred for the use of compounds of the formula (1.42) are the
Verbindungen 1.42-1 bis 1.42-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.42-1 bis 1.42-650 der Tabelle 1.42 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.42-1 to 1.42-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.42-1 to 1.42-650 of Table 1.42 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
(1.43)(1:43)
Figure imgf000099_0004
Tabelle 1.43: Bevorzugt für die Verwendung von Verbindungen der Formel (1.43) sind die
Figure imgf000099_0004
Table 1.43: Preferred for the use of compounds of the formula (1.43) are the
Verbindungen 1.43-1 bis 1.43-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.43-1 bis 1.43-650 der Tabelle 1.43 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.43-1 to 1.43-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.43-1 to 1.43-650 of Table 1.43 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000100_0001
Figure imgf000100_0001
Tabelle 1.44: Bevorzugt für die Verwendung von Verbindungen der Formel (1.44) sind die Table 1.44: Preferred for the use of compounds of the formula (1.44) are the
Verbindungen 1.44-1 bis 1.44-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.44-1 bis 1.44-650 der Tabelle 1.44 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.44-1 to 1.44-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.44-1 to 1.44-650 of Table 1.44 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000100_0002
Tabelle 1.45: Bevorzugt für die Verwendung von Verbindungen der Formel (1.45) sind die
Figure imgf000100_0002
Table 1.45: Preferred for the use of compounds of the formula (1.45) are the
Verbindungen 1.45-1 bis 1.45-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.45-1 bis 1.45-650 der Tabelle 1.45 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.45-1 to 1.45-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.45-1 to 1.45-650 of Table 1.45 are therefore distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000100_0003
Figure imgf000100_0003
Tabelle 1.46: Bevorzugt für die Verwendung von Verbindungen der Formel (1.46) sind die Table 1.46: Preferred for the use of compounds of formula (1.46) are the
Verbindungen 1.46-1 bis 1.46-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.46-1 bis 1.46-650 der Tabelle 1.46 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert.
Figure imgf000101_0001
Compounds 1.46-1 to 1.46-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.46-1 to 1.46-650 of Table 1.46 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000101_0001
Tabelle 1.47: Bevorzugt für die Verwendung von Verbindungen der Formel (1.47) sind die Table 1.47: Preferred for the use of compounds of formula (1.47) are the
Verbindungen 1.47-1 bis 1.47-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.47-1 bis 1.47-650 der Tabelle 1.47 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.47-1 to 1.47-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.47-1 to 1.47-650 of Table 1.47 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000101_0002
Tabelle 1.48: Bevorzugt für die Verwendung von Verbindungen der Formel (1.48) sind die
Figure imgf000101_0002
Table 1.48: Preferred for the use of compounds of the formula (1.48) are the
Verbindungen 1.48-1 bis 1.48-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.48-1 bis 1.48-650 der Tabelle 1.48 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.48-1 to 1.48-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.48-1 to 1.48-650 of Table 1.48 are thus characterized by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Figure imgf000101_0003
Figure imgf000101_0003
Tabelle 1.49: Bevorzugt für die Verwendung von Verbindungen der Formel (1.49) sind die Table 1.49: Preferred for the use of compounds of formula (1.49) are the
Verbindungen 1.49-1 bis 1.49-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.49-1 bis 1.49-650 der Tabelle 1.49 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Compounds 1.49-1 to 1.49-650, wherein R 5 and R 6 have the meanings indicated in the respective line of Table 1. The compounds 1.49-1 to 1.49-650 of Table 1.49 are thus distinguished by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
(1.50)(1.50)
Figure imgf000101_0004
Tabelle 1.50: Bevorzugt für die Verwendung von Verbindungen der Formel (1.50) sind die Verbindungen 1.50-1 bis 1.50-650, worin R5 und R6 die in der jeweiligen Zeile angegebenen
Figure imgf000101_0004
Table 1.50: Preferred for the use of compounds of the formula (1.50) are the compounds 1.50-1 to 1.50-650, wherein R 5 and R 6 are those indicated in the respective line
Bedeutungen der Tabelle 1 haben. Die Verbindungen 1.50-1 bis 1.50-650 der Tabelle 1.50 sind somit durch die Bedeutung der jeweiligen Einträge No. 1 bis 650 für R5 und R6 der Tabelle 1 definiert. Meanings of Table 1 have. The compounds 1.50-1 to 1.50-650 of Table 1.50 are thus affected by the meaning of the respective entries no. 1 to 650 defined for R 5 and R 6 of Table 1.
Spektroskopische Daten ausgewählter Tabellenbeispiele: Spectroscopic data of selected table examples:
Die nachfolgend aufgeführten spektroskopischen Daten ausgewählter Tabellenbeispiele wurden über NMR-Peak-Listenverfahren ausgewertet. Zu jedem Signalpeak wird erst der δ-Wert in ppm und dann die Signalintensität in runden Klammern aufgeführt. Die δ-Wert - Signalintensitäts- Zahlenpaare von verschiedenen Signalpeaks werden durch Semikolons voneinander getrennt aufgelistet. Die Peakliste eines Beispieles hat daher die Form: δι (Intensität^; 82 (Intensität2); ; δ; (Intensität^; ; δη (Intensitätn) The following spectroscopic data of selected table examples were evaluated by NMR peak list method. For each signal peak, first the δ value in ppm and then the signal intensity in round brackets are listed. The δ-value signal intensity number pairs of different signal peaks are listed separated by semicolons. The peak list of an example therefore has the form: δι (intensity ^; 82 (intensity 2);; δ; (intensity ^;; δ η (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. Zur Kalibrierung der chemischen Verschiebung von 1H-NMR-Spektren benutzen wir Tetramethylsilan und/oder die chemische Verschiebung des 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 true ratios of the signal intensities. For broad 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. To calibrate the chemical shift of 1H NMR spectra, we use tetramethylsilane and / or the chemical shift of the
Lösungsmittels, besondern im Falle von Spektren, die in DMSO gemessen werden. Daher kann in NMR-Peaklisten der Tetramethylsilan-Peak vorkommen, muss es aber nicht. Die Listen der 'H-NMR- Peaks sind ähnlich den klassischen 1H-NMR- Ausdrucken und enthalten somit gewöhnlich alle Peaks, die bei einer klassischen NMR-Interpretation aufgeführt werden.Darüber hinaus können sie wie klassische 1H-NMR- Ausdrucke Lösungsmittelsignale, Signale von Stereoisomeren der  Solvent, especially in the case of spectra, which are measured in DMSO. Therefore, the tetramethylsilane peak can occur in NMR peaks, but it does not have to. The lists of the 'H NMR peaks are similar to the classical 1H NMR prints and thus usually contain all the peaks that are listed in a classical NMR interpretation. In addition, they can, like classical 1H NMR prints solvent signals, signals from Stereoisomers of
Zielverbindungen, die ebenfalls Gegenstand der Erfindung sind, und/oder Peaks von Verunreinigungen zeigen. Bei der Angabe von Verbindungssignalen im Delta-Bereich von Lösungsmitteln und/oder Wasser sind in unseren Listen von IH-NMR-Peaks die gewöhnlichen Lösungsmittelpeaks, zum Beispiel Peaks von DMSO in DMSO-D6 und der Peak von Wasser, gezeigt, die gewöhnlich im Durchschnitt eine hohe Intensität aufweisen. Die Peaks von Stereoisomeren der Targetverbindungen und/oder Peaks von Verunreinigungen haben gewöhnlich im Durchschnitt eine geringere Intensität als die Peaks der Zielverbindungen (zum Beispiel mit einer Reinheit von >90 %).  Target compounds, which are also the subject of the invention, and / or show peaks of impurities. When indicating compound signals in the delta range of solvents and / or water, our lists of IH NMR peaks show the usual solvent peaks, for example, peaks of DMSO in DMSO-D6 and the peak of water, which are usually average have a high intensity. The peaks of stereoisomers of the target compounds and / or peaks of impurities usually have on average a lower intensity 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 may be typical of each
Herstellungsverfahren sein. Ihre Peaks können somit dabei helfen, die Reproduktion unseres Be manufacturing process. Their peaks can thus help the reproduction of our
Herstellungsverfahrens anhand von "Nebenprodukt-Fingerabdrucken" zu erkennen. Detect manufacturing process by "by-product fingerprints".
Einem Experten, der die Peaks der Zielverbindungen mit bekannten Verfahren (MestreC, ACD- Simulation, aber auch mit empirisch ausgewerteten Erwartungswerten) berechnet, kann je nach Bedarf die Peaks der Zielverbindungen isolieren, wobei gegebenenfalls zusätzliche Intensitätsfilter eingesetzt werden. Diese Isolierung wäre ähnlich dem betreffenden Peak-Picking bei der klassischen 1H-NMR- Interpretation. Weitere Details zu 'H-NMR-Peaklisten können der Research Disclosure Database Number 564025 entnommen werden. An expert who calculates the peaks of the target compounds using known methods (MestreC, ACD simulation, but also with empirically evaluated expectation values) can, as needed isolate the peaks of the target compounds, optionally using additional intensity filters. This isolation would be similar to peak picking in classical 1H NMR interpretation. Further details on 'H NMR peaks can be found in Research Disclosure Database Number 564025.
Beispiel Nr. 1.1-1 : Example No. 1.1-1:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.4734 (3.2); 7.4686 (1.0); 7.4562 (1.0); 7.4514 (3.5); 7.1159 (0.8); 6.7193 (0.8); 6.6664 (3.4); 6.6615 (1.0); 6.6491 (0.9); 6.6442 (3.3); 3.3137 (7.0); 3.2393 (1.5); 3.2232 (1.6); 3.2075 (0.8); 3.1091 (0.7); 3.0934 (1.6); 3.0775 (1.4); 2.9026 (16.0); 2.5106 (4.1); 2.5060 (9.1); 2.5015 (12.8); 2.4969 (9.1); 2.4923 (4.2); -0.0002 (5.3) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.4734 (3.2); 7.4686 (1.0); 7.4562 (1.0); 7.4514 (3.5); 7.1159 (0.8); 6.7193 (0.8); 6.6664 (3.4); 6.6615 (1.0); 6.6491 (0.9); 6.6442 (3.3); 3.3137 (7.0); 3.2393 (1.5); 3.2232 (1.6); 3.2075 (0.8); 3.1091 (0.7); 3.0934 (1.6); 3.0775 (1.4); 2.9026 (16.0); 2.5106 (4.1); 2.5060 (9.1); 2.5015 (12.8); 2.4969 (9.1); 2.4923 (4.2); -0.0002 (5.3)
Beispiel Nr. 1.1-4: Example No. 1.1-4:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.4721 (4.0); 7.4673 (1.6); 7.4501 (4.2); 7.4449 (0.8); 7.1175 (0.6); 7.1028 (1.2); 7.0885 (0.6); 6.7101 (0.5); 6.6956 (1.1); 6.6814 (0.7); 6.6568 (4.6); 6.6519 (1.4); 6.6345 (4.1); 3.3142 (19.3); 3.2337 (0.7); 3.2172 (1.9); 3.2020 (2.1); 3.1869 (1.9); 3.1702 (1.5); 3.1532 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.4721 (4.0); 7.4673 (1.6); 7.4501 (4.2); 7.4449 (0.8); 7.1175 (0.6); 7.1028 (1.2); 7.0885 (0.6); 6.7101 (0.5); 6.6956 (1.1); 6.6814 (0.7); 6.6568 (4.6); 6.6519 (1.4); 6.6345 (4.1); 3.3142 (19.3); 3.2337 (0.7); 3.2172 (1.9); 3.2020 (2.1); 3.1869 (1.9); 3.1702 (1.5); 3.1532
(1.1) ; 3.1091 (0.9); 3.0926 (1.9); 3.0769 (1.7); 3.0609 (0.6); 2.5106 (8.2); 2.5061 (17.0); 2.5015 (22.7); 2.4970 (15.8); 2.4924 (7.1); 1.6833 (1.4); 1.6759 (1.4); 1.2131 (16.0); 1.1961 (15.6); -0.0002 (3.9). (1.1); 3.1091 (0.9); 3.0926 (1.9); 3.0769 (1.7); 3.0609 (0.6); 2.5106 (8.2); 2.5061 (17.0); 2.5015 (22.7); 2.4970 (15.8); 2.4924 (7.1); 1.6833 (1.4); 1.6759 (1.4); 1.2131 (16.0); 1.1961 (15.6); -0.0002 (3.9).
Beispiel Nr. 1.1-34: Example Nos. 1.1-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8673 (6.2); 7.8542 (7.0); 7.8448 (8.1); 7.8318 (7.4); 7.7956 (5.9); 7.4421 (13.0); 7.4366 (11.5); 7.4202 (16.0); 7.4141 (16.0); 7.3919 (6.9); 6.6611 (2.3); 6.6467 (4.6); 6.6320 (2.6); 6.5826 (11.9); 6.5607 (12.1); 3.3175 (22.7); 3.1921 (2.7); 3.1765 (9.4); 3.1604 (8.8); 3.1447 (3.5); 2.8966 (5.7); 2.8802 (10.2); 2.8638 (4.9); 2.5033 (59.4); -0.0002 (16.6); -0.0017 (12.1). Beispiel Nr. 1.1-35: 1H NMR (400.0 MHz, de-DMSO): δ = 7.8673 (6.2); 7.8542 (7.0); 7.8448 (8.1); 7.8318 (7.4); 7.7956 (5.9); 7.4421 (13.0); 7.4366 (11.5); 7.4202 (16.0); 7.4141 (16.0); 7.3919 (6.9); 6.6611 (2.3); 6.6467 (4.6); 6.6320 (2.6); 6.5826 (11.9); 6.5607 (12.1); 3.3175 (22.7); 3.1921 (2.7); 3.1765 (9.4); 3.1604 (8.8); 3.1447 (3.5); 2.8966 (5.7); 2.8802 (10.2); 2.8638 (4.9); 2.5033 (59.4); -0.0002 (16.6); -0.0017 (12.1). Example Nos. 1.1-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7932 (11.8); 7.7883 (4.4); 7.7767 (4.6); 7.7715 (16.0); 7.6519 (15.7); 7.6469 (4.4); 7.6351 (3.8); 7.6302 (11.3); 7.4361 (11.5); 7.4140 (12.3); 6.6325 (3.1); 6.5704 (11.4); 6.5481 (11.0); 3.3089 (121.8); 3.1865 (2.0); 3.1708 (5.8); 3.1551 (6.2); 3.1388 (2.8); 2.9043 (4.6); 2.8878 (8.2); 2.8711 (3.5); 2.6702 (1.7); 2.5098 (101.1); 2.5053 (210.4); 2.5007 (287.7); 2.4962 (204.2); 2.4917 (94.0); 2.3276 (1.7); 0.0081 (3.4); -0.0002 (88.6); -0.0086 (2.8). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7932 (11.8); 7.7883 (4.4); 7.7767 (4.6); 7.7715 (16.0); 7.6519 (15.7); 7.6469 (4.4); 7.6351 (3.8); 7.6302 (11.3); 7.4361 (11.5); 7.4140 (12.3); 6.6325 (3.1); 6.5704 (11.4); 6.5481 (11.0); 3.3089 (121.8); 3.1865 (2.0); 3.1708 (5.8); 3.1551 (6.2); 3.1388 (2.8); 2.9043 (4.6); 2.8878 (8.2); 2.8711 (3.5); 2.6702 (1.7); 2.5098 (101.1); 2.5053 (210.4); 2,5007 (287.7); 2.4962 (204.2); 2.4917 (94.0); 2.3276 (1.7); 0.0081 (3.4); -0.0002 (88.6); -0.0086 (2.8).
Beispiel Nr. 1.1-40: Example No. 1.1-40:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7352 (0.5); 7.7276 (4.0); 7.7225 (1.2); 7.7105 (1.4); 7.7055 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7352 (0.5); 7.7276 (4.0); 7.7225 (1.2); 7.7105 (1.4); 7.7055
(4.2) ; 7.4384 (3.5); 7.4341 (1.1); 7.4165 (3.6); 7.1077 (0.5); 7.1002 (4.1); 7.0951 (1.2); 7.0830 (1.3); 7.0780 (3.7); 6.6502 (0.6); 6.6354 (1.1); 6.6207 (0.5); 6.5751 (3.6); 6.5705 (1.2); 6.5530 (3.4); 3.8259(4.2); 7.4384 (3.5); 7.4341 (1.1); 7.4165 (3.6); 7.1077 (0.5); 7.1002 (4.1); 7.0951 (1.2); 7.0830 (1.3); 7.0780 (3.7); 6.6502 (0.6); 6.6354 (1.1); 6.6207 (0.5); 6.5751 (3.6); 6.5705 (1.2); 6.5530 (3.4); 3.8259
(16.0); 3.3157 (10.7); 3.1778 (0.8); 3.1601 (1.8); 3.1442 (1.9); 3.1279 (0.8); 2.8489 (1.0); 2.8327 (1.6); 2.8164 (0.8); 2.5246 (0.5); 2.5113 (5.8); 2.5069 (11.1); 2.5024 (14.5); 2.4979 (10.1); 2.4935 (4.6); 2.0735 (0.7); -0.0002 (4.6). (16.0); 3.3157 (10.7); 3.1778 (0.8); 3.1601 (1.8); 3.1442 (1.9); 3.1279 (0.8); 2.8489 (1.0); 2.8327 (1.6); 2.8164 (0.8); 2.5246 (0.5); 2.5113 (5.8); 2.5069 (11.1); 2.5024 (14.5); 2.4979 (10.1); 2.4935 (4.6); 2.0735 (0.7); -0.0002 (4.6).
Beispiel Nr. 1.1-50: Example No. 1.1-50:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.6824 (12.5); 7.6781 (4.5); 7.6660 (5.6); 7.6617 (16.0); 7.65661 H NMR (400.0 MHz, de-DMSO): δ = 7.6824 (12.5); 7.6781 (4.5); 7.6660 (5.6); 7.6617 (16.0); 7.6566
(4.5) ; 7.4386 (13.7); 7.4340 (4.1); 7.4213 (4.1); 7.4166 (14.6); 7.3842 (10.4); 7.3644 (9.2); 6.6489 (1.8); 6.6342 (3.6); 6.6191 (1.8); 6.5783 (1.6); 6.5721 (13.7); 6.5673 (4.2); 6.5548 (4.0); 6.5499 (13.1); 4.0898 (0.6); 4.0768 (0.7); 3.3181 (27.9); 3.1790 (5.8); 3.1659 (5.9); 3.1605 (6.5); 3.1444 (6.7); 3.1283 (2.8); 2.8454 (4.0); 2.5253 (0.8); 2.5204 (1.1); 2.5119 (17.5); 2.5073 (38.4); 2.5027 (53.9); 2.4981 (38.2); 2.4936 (17.4); 2.3715 (36.0); 2.0738 (2.2); 0.0079 (0.7); -0.0002 (22.5); -0.0085 (0.7). (4.5); 7.4386 (13.7); 7.4340 (4.1); 7.4213 (4.1); 7.4166 (14.6); 7.3842 (10.4); 7.3644 (9.2); 6.6489 (1.8); 6.6342 (3.6); 6.6191 (1.8); 6.5783 (1.6); 6.5721 (13.7); 6.5673 (4.2); 6.5548 (4.0); 6.5499 (13.1); 4.0898 (0.6); 4.0768 (0.7); 3,3181 (27.9); 3.1790 (5.8); 3.1659 (5.9); 3.1605 (6.5); 3.1444 (6.7); 3.1283 (2.8); 2.8454 (4.0); 2.5253 (0.8); 2.5204 (1.1); 2.5119 (17.5); 2.5073 (38.4); 2.5027 (53.9); 2.4981 (38.2); 2.4936 (17.4); 2.3715 (36.0); 2.0738 (2.2); 0.0079 (0.7); -0.0002 (22.5); -0.0085 (0.7).
Beispiel Nr. 1.1-54: Example No. 1.1-54:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9233 (2.7); 7.9107 (6.2); 7.8961 (3.2); 7.7907 (10.9); 7.7617 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9233 (2.7); 7.9107 (6.2); 7.8961 (3.2); 7.7907 (10.9); 7.7617
(5.8) ; 7.7411 (7.6); 7.7269 (5.2); 7.7043 (7.3); 7.6366 (7.1); 7.6171 (9.5); 7.5971 (3.9); 7.4400 (14.1); 7.4185 (16.0); 6.6683 (2.8); 6.6540 (5.5); 6.6393 (2.9); 6.5836 (14.5); 6.5624 (14.5); 3.3136 (115.3);(5.8); 7.7411 (7.6); 7.7269 (5.2); 7.7043 (7.3); 7.6366 (7.1); 7.6171 (9.5); 7,591 (3.9); 7.4400 (14.1); 7.4185 (16.0); 6.6683 (2.8); 6.6540 (5.5); 6.6393 (2.9); 6.5836 (14.5); 6.5624 (14.5); 3.3136 (115.3);
3.1965 (3.1); 3.1809 (9.5); 3.1643 (11.4); 3.1488 (4.4); 2.9308 (3.6); 2.9161 (9.2); 2.9007 (8.7); 2.8844 (3.2); 2.6740 (0.9); 2.5016 (157.6); 2.3297 (0.9); -0.0002 (25.3); -0.0015 (22.4). 3.1965 (3.1); 3.1809 (9.5); 3.1643 (11.4); 3.1488 (4.4); 2.9308 (3.6); 2.9161 (9.2); 2.9007 (8.7); 2.8844 (3.2); 2.6740 (0.9); 2.5016 (157.6); 2.3297 (0.9); -0.0002 (25.3); -0.0015 (22.4).
Beispiel Nr. 1.1-61 : Example No. 1.1-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9822 (10.3); 7.9637 (9.8); 7.9616 (9.3); 7.6359 (15.4); 7.6339 (14.5); 7.6277 (12.4); 7.6227 (9.6); 7.6193 (7.6); 7.6028 (1.9); 7.5477 (4.4); 7.5397 (4.0); 7.5338 (3.8); 7.5279 (5.5); 7.5212 (3.9); 7.5135 (3.3); 7.5064 (3.1); 7.4361 (15.4); 7.4142 (16.0); 6.6364 (2.8); 6.6226 (5.4); 6.6070 (3.0); 6.5461 (15.6); 6.5240 (14.8); 4.0895 (0.6); 4.0762 (0.7); 3.3159 (30.5); 3.1784 (6.6); 3.1650 (10.5); 3.1473 (9.0); 3.1308 (4.6); 2.9809 (7.4); 2.9664 (6.9); 2.6725 (0.6); 2.5072 (71.6); 2.5028 (91.0); 2.4983 (67.6); 2.3340 (1.1); 2.0740 (8.2); -0.0002 (25.5) 1H NMR (400.0 MHz, de-DMSO): δ = 7.9822 (10.3); 7.9637 (9.8); 7.9616 (9.3); 7.6359 (15.4); 7.6339 (14.5); 7.6277 (12.4); 7.6227 (9.6); 7.6193 (7.6); 7.6028 (1.9); 7.5477 (4.4); 7.5397 (4.0); 7.5338 (3.8); 7.5279 (5.5); 7.5212 (3.9); 7.5135 (3.3); 7.5064 (3.1); 7.4361 (15.4); 7.4142 (16.0); 6.6364 (2.8); 6.6226 (5.4); 6.6070 (3.0); 6.5461 (15.6); 6.5240 (14.8); 4.0895 (0.6); 4.0762 (0.7); 3.3159 (30.5); 3.1784 (6.6); 3.1650 (10.5); 3.1473 (9.0); 3.1308 (4.6); 2.9809 (7.4); 2.9664 (6.9); 2.6725 (0.6); 2.5072 (71.6); 2.5028 (91.0); 2.4983 (67.6); 2.3340 (1.1); 2.0740 (8.2); -0.0002 (25.5)
Beispiel Nr. 1.1-62: Example Nos. 1.1-62:
1H-NMR(400.0 MHz, d6-DMSO): δ= 8.0182 (4.6); 7.8199 (2.4); 7.8156 (2.7); 7.8008 (4.6); 7.7965 1 H-NMR (400.0 MHz, d6-DMSO): δ = 8.0182 (4.6); 7.8199 (2.4); 7.8156 (2.7); 7.8008 (4.6); 7.7965
(4.9) ; 7.7819 (2.6); 7.7774 (2.8); 7.7175 (1.3); 7.7131 (1.3); 7.7048 (1.4); 7.6992 (2.2); 7.6967 (2.0); 7.6944 (2.0); 7.6924 (1.8); 7.6861 (2.0); 7.6839 (1.9); 7.6817 (2.1); 7.6787 (2.3); 7.6736 (1.6); 7.6654(4.9); 7.7819 (2.6); 7.7774 (2.8); 7.7175 (1.3); 7.7131 (1.3); 7.7048 (1.4); 7.6992 (2.2); 7.6967 (2.0); 7.6944 (2.0); 7.6924 (1.8); 7.6861 (2.0); 7.6839 (1.9); 7.6817 (2.1); 7.6787 (2.3); 7.6736 (1.6); 7.6654
(1.6) ; 7.6609 (1.4); 7.4474 (1.6); 7.4412 (14.3); 7.4363 (7.1); 7.4239 (4.2); 7.4191 (16.0); 7.4123 (4.3); 7.4096 (3.9); 7.3952 (4.6); 7.3923 (4.8); 7.3887 (3.0); 7.3762 (6.5); 7.3736 (5.7); 7.3571 (3.4); 7.3544 (3.1); 6.6637 (1.8); 6.6489 (3.6); 6.6340 (1.8); 6.5773 (1.6); 6.5710 (14.2); 6.5661 (4.2); 6.5537 (4.0); 6.5488 (13.5); 6.5426 (1.5); 3.3158 (35.7); 3.1982 (2.0); 3.1821 (6.0); 3.1654 (6.8); 3.1495 (2.9); 3.0122 (5.1); 2.9950 (7.9); 2.9786 (3.4); 2.5251 (1.1); 2.5204 (1.5); 2.5118 (19.6); 2.5072 (42.6); 2.5026 (59.2); 2.4980 (41.8); 2.4934 (19.0); 0.0080 (0.8); -0.0002 (24.6); -0.0085 (0.7). Beispiel Nr. 1.1-64: (1.6); 7.6609 (1.4); 7.4474 (1.6); 7.4412 (14.3); 7.4363 (7.1); 7.4239 (4.2); 7.4191 (16.0); 7.4123 (4.3); 7.4096 (3.9); 7.3952 (4.6); 7.3923 (4.8); 7.3887 (3.0); 7.3762 (6.5); 7.3736 (5.7); 7.3571 (3.4); 7.3544 (3.1); 6.6637 (1.8); 6.6489 (3.6); 6.6340 (1.8); 6.5773 (1.6); 6.5710 (14.2); 6.5661 (4.2); 6.5537 (4.0); 6.5488 (13.5); 6.5426 (1.5); 3.3158 (35.7); 3.1982 (2.0); 3.1821 (6.0); 3.1654 (6.8); 3.1495 (2.9); 3.0122 (5.1); 2.9950 (7.9); 2.9786 (3.4); 2.5251 (1.1); 2.5204 (1.5); 2.5118 (19.6); 2.5072 (42.6); 2.5026 (59.2); 2.4980 (41.8); 2.4934 (19.0); 0.0080 (0.8); -0.0002 (24.6); -0.0085 (0.7). Example Nos. 1.1-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8939 (4.9); 7.6801 (0.8); 7.6606 (4.2); 7.6486 (10.4); 7.6452 (11.1); 7.6427 (8.6); 7.6398 (6.0); 7.6363 (8.1); 7.6291 (1.4); 7.6169 (0.5); 7.5946 (3.1); 7.5894 (3.6); 7.5865 (4.0); 7.5715 (3.3); 7.5679 (3.5); 7.5650 (3.5); 7.5302 (2.0); 7.5234 (3.0); 7.5174 (2.0); 7.5143 (2.0); 7.5074 (4.0); 7.5011 (2.7); 7.4974 (2.3); 7.4899 (2.2); 7.4850 (1.6); 7.4784 (1.2); 7.4422 (15.2); 7.4376 (4.9); 7.4202 (15.7); 7.4141 (1.9); 6.6721 (2.3); 6.6575 (4.3); 6.6428 (2.2); 6.5883 (16.0); 6.5836 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8939 (4.9); 7.6801 (0.8); 7.6606 (4.2); 7.6486 (10.4); 7.6452 (11.1); 7.6427 (8.6); 7.6398 (6.0); 7.6363 (8.1); 7.6291 (1.4); 7.6169 (0.5); 7.5946 (3.1); 7.5894 (3.6); 7.5865 (4.0); 7.5715 (3.3); 7.5679 (3.5); 7.5650 (3.5); 7.5302 (2.0); 7.5234 (3.0); 7.5174 (2.0); 7.5143 (2.0); 7.5074 (4.0); 7.5011 (2.7); 7.4974 (2.3); 7.4899 (2.2); 7.4850 (1.6); 7.4784 (1.2); 7.4422 (15.2); 7.4376 (4.9); 7.4202 (15.7); 7.4141 (1.9); 6.6721 (2.3); 6.6575 (4.3); 6.6428 (2.2); 6.5883 (16.0); 6.5836
(5.1) ; 6.5707 (5.4); 6.5662 (14.9); 6.5601 (1.8); 3.3150 (32.1); 3.1991 (2.9); 3.1829 (8.4); 3.1670 (9.5); 3.1513 (3.5); 2.9295 (6.0); 2.9132 (10.5); 2.8967 (4.5); 2.5248 (2.4); 2.5117 (26.5); 2.5073 (51.8); 2.5027 (68.5); 2.4982 (48.1); 2.4937 (22.0); 0.0079 (1.2); -0.0002 (25.6); -0.0084 (0.9). (5.1); 6.5707 (5.4); 6.5662 (14.9); 6.5601 (1.8); 3.3150 (32.1); 3.1991 (2.9); 3.1829 (8.4); 3.1670 (9.5); 3.1513 (3.5); 2.9295 (6.0); 2.9132 (10.5); 2.8967 (4.5); 2.5248 (2.4); 2.5117 (26.5); 2.5073 (51.8); 2.5027 (68.5); 2.4982 (48.1); 2.4937 (22.0); 0.0079 (1.2); -0.0002 (25.6); -0.0084 (0.9).
Beispiel Nr. 1.1-73: Example No. 1.1-73:
'H-NMR^OO.O MHZ, de-DMSO): δ= 7.7559 (1.2); 7.5227 (1.0); 7.5028 (2.0); 7.4827 (1.6); 7.4405 'H-NMR ^ OO.O MHZ, de-DMSO): δ = 7.7559 (1.2); 7.5227 (1.0); 7.5028 (2.0); 7.4827 (1.6); 7.4405
(3.2) ; 7.4359 (1.0); 7.4231 (1.0); 7.4185 (3.4); 7.3787 (1.0); 7.3763 (1.3); 7.3747 (1.2); 7.3723 (1.1); 7.3594 (0.8); 7.3570 (0.9); 7.3554 (1.0); 7.3531 (0.8); 7.2977 (1.3); 7.2916 (1.7); 7.2873 (1.3); 7.2112 (1.0); 7.2091 (1.0); 7.2048 (0.9); 7.2027 (0.8); 7.1906 (0.9); 7.1884 (0.8); 7.1841 (0.8); 7.1820 (0.7); 6.6492 (0.9); 6.5833 (3.3); 6.5785 (1.1); 6.5660 (1.0); 6.5611 (3.1); 3.8113 (16.0); 3.3177 (5.8); 3.1873 (0.6); 3.1785 (0.8); 3.1710 (1.8); 3.1552 (1.7); 3.1391 (0.7); 2.8905 (1.2); 2.8739 (2.0); 2.8573 (0.9); 2.5206 (0.5); 2.5121 (3.8); 2.5075 (7.7); 2.5029 (10.5); 2.4984 (7.4); 2.4938 (3.4); -0.0002 (4.7) Beispiel Nr. 1.1-92: (3.2); 7.4359 (1.0); 7.4231 (1.0); 7.4185 (3.4); 7.3787 (1.0); 7.3763 (1.3); 7.3747 (1.2); 7.3723 (1.1); 7.3594 (0.8); 7.3570 (0.9); 7.3554 (1.0); 7.3531 (0.8); 7.2977 (1.3); 7.2916 (1.7); 7.2873 (1.3); 7.2112 (1.0); 7.2091 (1.0); 7.2048 (0.9); 7.2027 (0.8); 7.1906 (0.9); 7.1884 (0.8); 7.1841 (0.8); 7.1820 (0.7); 6.6492 (0.9); 6.5833 (3.3); 6.5785 (1.1); 6.5660 (1.0); 6.5611 (3.1); 3.8113 (16.0); 3.3177 (5.8); 3.1873 (0.6); 3.1785 (0.8); 3.1710 (1.8); 3.1552 (1.7); 3.1391 (0.7); 2.8905 (1.2); 2.8739 (2.0); 2.8573 (0.9); 2.5206 (0.5); 2.5121 (3.8); 2.5075 (7.7); 2.5029 (10.5); 2.4984 (7.4); 2.4938 (3.4); -0.0002 (4.7) Example Nos. 1.1-92:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7733 (3.5); 7.7295 (4.0); 7.7267 (3.3); 7.5400 (0.8); 7.5252 (1.6); 7.5109 (0.8); 7.4544 (4.2); 7.4325 (4.4); 6.6711 (0.8); 6.6562 (1.4); 6.6425 (0.7); 6.5962 (4.4); 6.5741 (4.0); 3.6833 (16.0); 3.3153 (14.6); 3.1950 (0.8); 3.1789 (2.2); 3.1626 (2.2); 3.1460 (1.0); 2.9842 (1.1); 2.9690 (2.2); 2.9519 (2.1); 2.9357 (0.7); 2.5062 (16.8); 2.5018 (22.1); 2.4974 (16.0); -0.0002 (1.5) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7733 (3.5); 7.7295 (4.0); 7.7267 (3.3); 7.5400 (0.8); 7.5252 (1.6); 7.5109 (0.8); 7.4544 (4.2); 7.4325 (4.4); 6.6711 (0.8); 6.6562 (1.4); 6.6425 (0.7); 6.5962 (4.4); 6.5741 (4.0); 3.6833 (16.0); 3.3153 (14.6); 3.1950 (0.8); 3.1789 (2.2); 3.1626 (2.2); 3.1460 (1.0); 2.9842 (1.1); 2.9690 (2.2); 2.9519 (2.1); 2.9357 (0.7); 2.5062 (16.8); 2.5018 (22.1); 2.4974 (16.0); -0.0002 (1.5)
Beispiel Nr. 1.1-204: Example No. 1.1-204:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.4631 (1.5); 7.4570 (12.0); 7.4524 (3.8); 7.4467 (4.6); 7.4402 (5.4); 7.4349 (16.0); 7.4307 (4.1); 7.4236 (5.4); 7.4147 (0.8); 7.3918 (3.3); 7.3848 (3.6); 7.3810 (4.4); 7.3741 (4.2); 7.3687 (7.1); 7.3609 (1.7); 7.3563 (1.7); 7.3075 (1.6); 7.3019 (0.8); 7.2955 (7.8); 7.2936 (7.5); 7.2892 (5.2); 7.2830 (8.0); 7.2768 (4.4); 7.2721 (5.4); 7.2705 (5.1); 7.2584 (0.9); 6.7323 (1.6); 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.4631 (1.5); 7.4570 (12.0); 7.4524 (3.8); 7.4467 (4.6); 7.4402 (5.4); 7.4349 (16.0); 7.4307 (4.1); 7.4236 (5.4); 7.4147 (0.8); 7.3918 (3.3); 7.3848 (3.6); 7.3810 (4.4); 7.3741 (4.2); 7.3687 (7.1); 7.3609 (1.7); 7.3563 (1.7); 7.3075 (1.6); 7.3019 (0.8); 7.2955 (7.8); 7.2936 (7.5); 7.2892 (5.2); 7.2830 (8.0); 7.2768 (4.4); 7.2721 (5.4); 7.2705 (5.1); 7.2584 (0.9); 6.7323 (1.6);
6.7177 (3.3); 6.7033 (1.6); 6.6638 (1.5); 6.6575 (12.7); 6.6527 (3.8); 6.6401 (3.6); 6.6353 (12.0); 3.3111 (229.0); 3.2780 (3.9); 3.2646 (4.9); 3.2561 (5.9); 3.2521 (6.1); 3.2477 (6.5); 3.2365 (11.8); 3.2208 (2.9); 3.1757 (0.6); 3.1625 (0.8); 3.1506 (2.3); 3.1355 (5.1); 3.1201 (4.3); 3.1041 (1.4); 3.0839 (5.6); 3.0729 (3.8); 3.0626 (3.7); 3.0561 (3.5); 3.0429 (3.4); 2.6745 (0.9); 2.6699 (1.3); 2.6651 (0.9); 2.5233 (3.5); 2.5186 (5.2); 2.5099 (72.3); 2.5053 (156.6); 2.5008 (218.1); 2.4962 (155.1); 2.4916 (70.9); 2.3321 (0.9); 2.3276 (1.3); 2.3230 (1.0); 2.3029 (0.5); 0.0080 (1.2); -0.0002 (39.0); -0.0085 (1.2) Beispiel Nr. 1.2-1 : 6.7177 (3.3); 6.7033 (1.6); 6.6638 (1.5); 6.6575 (12.7); 6.6527 (3.8); 6.6401 (3.6); 6.6353 (12.0); 3.3111 (229.0); 3.2780 (3.9); 3.2646 (4.9); 3.2561 (5.9); 3.2521 (6.1); 3.2477 (6.5); 3.2365 (11.8); 3.2208 (2.9); 3.1757 (0.6); 3.1625 (0.8); 3.1506 (2.3); 3.1355 (5.1); 3.1201 (4.3); 3.1041 (1.4); 3.0839 (5.6); 3.0729 (3.8); 3.0626 (3.7); 3.0561 (3.5); 3.0429 (3.4); 2.6745 (0.9); 2.6699 (1.3); 2.6651 (0.9); 2.5233 (3.5); 2.5186 (5.2); 2.5099 (72.3); 2.5053 (156.6); 2,5008 (218.1); 2.4962 (155.1); 2.4916 (70.9); 2.3321 (0.9); 2.3276 (1.3); 2.3230 (1.0); 2.3029 (0.5); 0.0080 (1.2); -0.0002 (39.0); -0.0085 (1.2) Example No. 1.2-1:
'H-NMR^OO.O MHz, de-DMSO): δ= 7.5504 (2.4); 7.5286 (2.5); 7.1327 (0.7); 7.1174 (1.4); 7.1023 (0.8); 7.0823 (0.7); 7.0681 (1.3); 7.0536 (0.7); 6.7902 (2.8); 6.7847 (2.8); 6.6463 (1.5); 6.6407 (1.4); 6.6244 (1.5); 6.6188 (1.3); 3.3142 (5.6); 3.2770 (0.8); 3.2614 (2.3); 3.2455 (2.6); 3.2301 (1.1); 3.1029 (1.1); 3.0870 (2.8); 3.0714 (2.5); 3.0551 (0.8); 2.9082 (16.0); 2.5065 (13.7); 2.5022 (17.2); 2.4978 (12.1); -0.0002 (0.8)  'H NMR ^ OO.O MHz, de-DMSO): δ = 7.5504 (2.4); 7.5286 (2.5); 7.1327 (0.7); 7.1174 (1.4); 7.1023 (0.8); 7.0823 (0.7); 7.0681 (1.3); 7.0536 (0.7); 6.7902 (2.8); 6.7847 (2.8); 6.6463 (1.5); 6.6407 (1.4); 6.6244 (1.5); 6.6188 (1.3); 3.3142 (5.6); 3.2770 (0.8); 3.2614 (2.3); 3.2455 (2.6); 3.2301 (1.1); 3.1029 (1.1); 3.0870 (2.8); 3.0714 (2.5); 3.0551 (0.8); 2.9082 (16.0); 2.5065 (13.7); 2.5022 (17.2); 2.4978 (12.1); -0.0002 (0.8)
Beispiel Nr. 1.2-4: Example No. 1.2-4:
1H-NMR(400.0 MHz, CDC13): δ= 7.3954 (2.6); 7.3739 (2.7); 7.2613 (23.7); 6.6269 (2.5); 6.6211 (2.7); 6.5068 (1.6); 6.5010 (1.4); 6.4852 (1.5); 6.4794 (1.4); 4.9909 (0.5); 3.4107 (1.4); 3.4068 (1.0); 3.3967 (1.8); 3.3908 (0.8); 3.3810 (1.0); 3.3451 (0.8); 3.3318 (1.5); 3.3179 (1.1); 3.2195 (1.1); 3.2024 (1.4); 3.1854 (1.1); 1.5699 (5.0); 1.3980 (16.0); 1.3809 (15.7); -0.0002 (8.1) 1 H-NMR (400.0 MHz, CDCl 3 ): δ = 7.3954 (2.6); 7.3739 (2.7); 7.2613 (23.7); 6.6269 (2.5); 6.6211 (2.7); 6.5068 (1.6); 6.5010 (1.4); 6.4852 (1.5); 6.4794 (1.4); 4.9909 (0.5); 3.4107 (1.4); 3.4068 (1.0); 3.3967 (1.8); 3,3908 (0.8); 3.3810 (1.0); 3.3451 (0.8); 3.3318 (1.5); 3.3179 (1.1); 3.2195 (1.1); 3.2024 (1.4); 3.1854 (1.1); 1.5699 (5.0); 1.3980 (16.0); 1.3809 (15.7); -0.0002 (8.1)
Beispiel Nr. 1.2-34: Example Nos. 1.2-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8681 (0.8); 7.8604 (8.0); 7.8551 (3.3); 7.8473 (8.7); 7.8430 (4.1); 7.8380 (9.0); 7.8303 (3.6); 7.8250 (8.6); 7.8173 (1.2); 7.7945 (4.6); 7.5168 (9.7); 7.4950 (10.3); 7.4388 (0.9); 7.4312 (8.6); 7.4259 (2.6); 7.4142 (2.8); 7.4091 (16.0); 7.4039 (2.9); 7.3921 (2.4); 7.3869 (7.6); 7.3791 (0.7); 7.0071 (1.8); 6.9923 (3.8); 6.9773 (1.8); 6.6947 (9.2); 6.6891 (10.0); 6.5675 (5.3); 6.5618 (4.9); 6.5456 (5.0); 6.5399 (4.8); 3.3159 (23.1); 3.2185 (2.3); 3.2025 (7.1); 3.1870 (7.6); 3.1715 (2.8); 2.8918 (5.4); 2.8760 (10.9); 2.8598 (4.5); 2.5258 (1.1); 2.5212 (1.7); 2.5125 (25.7); 2.5080 (56.3); 2.5034 (79.2); 2.4988 (56.1); 2.4942 (25.5); 0.0080 (1.1); -0.0002 (34.5); -0.0085 (1.0) 1 H NMR (400.0 MHz, de-DMSO): δ = 7.8681 (0.8); 7.8604 (8.0); 7.8551 (3.3); 7.8473 (8.7); 7.8430 (4.1); 7.8380 (9.0); 7.8303 (3.6); 7.8250 (8.6); 7.8173 (1.2); 7.7945 (4.6); 7.5168 (9.7); 7.4950 (10.3); 7.4388 (0.9); 7.4312 (8.6); 7.4259 (2.6); 7.4142 (2.8); 7.4091 (16.0); 7.4039 (2.9); 7.3921 (2.4); 7.3869 (7.6); 7.3791 (0.7); 7.0071 (1.8); 6.9923 (3.8); 6.9773 (1.8); 6.6947 (9.2); 6.6891 (10.0); 6.5675 (5.3); 6.5618 (4.9); 6.5456 (5.0); 6.5399 (4.8); 3.3159 (23.1); 3.2185 (2.3); 3.2025 (7.1); 3.1870 (7.6); 3.1715 (2.8); 2.8918 (5.4); 2.8760 (10.9); 2.8598 (4.5); 2.5258 (1.1); 2.5212 (1.7); 2.5125 (25.7); 2.5080 (56.3); 2.5034 (79.2); 2.4988 (56.1); 2.4942 (25.5); 0.0080 (1.1); -0.0002 (34.5); -0.0085 (1.0)
Beispiel Nr. 1.2-35: Example No. 1.2-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8663 (1.8); 7.8517 (3.9); 7.8371 (1.8); 7.7949 (1.3); 7.7885 (11.7); 7.7834 (3.8); 7.7719 (4.4); 7.7667 (16.0); 7.7604 (1.9); 7.6527 (1.9); 7.6464 (15.7); 7.6413 (4.2); 7.6297 (3.6); 7.6247 (11.1); 7.6182 (1.1); 7.5106 (7.4); 7.4888 (7.8); 6.9883 (1.4); 6.9735 (2.9); 6.9586 (1.4); 6.6848 (7.1); 6.6792 (7.6); 6.5548 (4.2); 6.5491 (3.8); 6.5329 (4.0); 6.5272 (3.7); 3.3128 (54.1); 3.2130 (1.8); 3.1971 (5.5); 3.1816 (5.8); 3.1661 (2.1); 2.9106 (2.2); 2.8952 (6.2); 2.8801 (5.7); 2.8642 (1.8); 2.6712 (0.5); 2.5246 (1.7); 2.5199 (2.3); 2.5112 (29.2); 2.5067 (62.7); 2.5021 (86.9); 2.4975 (60.8); 2.4929 (27.4); 2.3289 (0.5); 1.9887 (1.4); 1.1754 (0.8); -0.0002 (2.1). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8663 (1.8); 7.8517 (3.9); 7.8371 (1.8); 7.7949 (1.3); 7.7885 (11.7); 7.7834 (3.8); 7.7719 (4.4); 7.7667 (16.0); 7.7604 (1.9); 7.6527 (1.9); 7.6464 (15.7); 7.6413 (4.2); 7.6297 (3.6); 7.6247 (11.1); 7.6182 (1.1); 7.5106 (7.4); 7.4888 (7.8); 6.9883 (1.4); 6.9735 (2.9); 6.9586 (1.4); 6.6848 (7.1); 6.6792 (7.6); 6.5548 (4.2); 6.5491 (3.8); 6.5329 (4.0); 6.5272 (3.7); 3.3128 (54.1); 3.2130 (1.8); 3.1971 (5.5); 3.1816 (5.8); 3.1661 (2.1); 2.9106 (2.2); 2.8952 (6.2); 2.8801 (5.7); 2.8642 (1.8); 2.6712 (0.5); 2.5246 (1.7); 2.5199 (2.3); 2.5112 (29.2); 2.5067 (62.7); 2.5021 (86.9); 2.4975 (60.8); 2.4929 (27.4); 2.3289 (0.5); 1.9887 (1.4); 1.1754 (0.8); -0.0002 (2.1).
Beispiel Nr. 1.2-40: Example No. 1.2-40:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7204 (3.8); 7.7152 (1.1); 7.7033 (1.1); 7.6981 (4.1); 7.5705 (1.0); 7.5123 (2.2); 7.4905 (2.3); 7.0924 (3.9); 7.0872 (1.1); 7.0753 (1.0); 7.0701 (3.6); 6.9803 (0.9); 6.6893 (2.0); 6.6837 (2.2); 6.5593 (1.2); 6.5536 (1.1); 6.5374 (1.1); 6.5317 (1.0); 3.8258 (16.0); 3.3132 (8.3); 3.2008 (0.5); 3.1848 (1.6); 3.1691 (1.6); 3.1533 (0.6); 2.8496 (0.5); 2.8342 (1.3); 2.8192 (1.2); 2.5113 (6.3); 2.5068 (13.5); 2.5022 (18.6); 2.4976 (13.0); 2.4930 (5.8); -0.0002 (10.1) Beispiel Nr. 1.2-50: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7204 (3.8); 7.7152 (1.1); 7.7033 (1.1); 7.6981 (4.1); 7.5705 (1.0); 7.5123 (2.2); 7.4905 (2.3); 7.0924 (3.9); 7.0872 (1.1); 7.0753 (1.0); 7.0701 (3.6); 6.9803 (0.9); 6.6893 (2.0); 6.6837 (2.2); 6.5593 (1.2); 6.5536 (1.1); 6.5374 (1.1); 6.5317 (1.0); 3.8258 (16.0); 3.3132 (8.3); 3.2008 (0.5); 3.1848 (1.6); 3.1691 (1.6); 3.1533 (0.6); 2.8496 (0.5); 2.8342 (1.3); 2.8192 (1.2); 2.5113 (6.3); 2.5068 (13.5); 2.5022 (18.6); 2.4976 (13.0); 2.4930 (5.8); -0.0002 (10.1) Example No. 1.2-50:
'H-NMR^OO.O MHz, de-DMSO): δ= 7.6725 (11.9); 7.6518 (16.0); 7.5115 (9.1); 7.4897 (9.5); 7.3760 'H-NMR ^ OO.O MHz, de-DMSO): δ = 7.6725 (11.9); 7.6518 (16.0); 7.5115 (9.1); 7.4897 (9.5); 7.3760
(9.8) ; 7.3562 (9.0); 6.9908 (1.7); 6.9759 (3.6); 6.9611 (1.8); 6.6827 (8.2); 6.6771 (8.8); 6.5537 (4.7); 6.5481 (4.2); 6.5319 (4.4); 6.5262 (4.2); 4.0863 (0.9); 4.0732 (0.9); 3.3112 (99.0); 3.1984 (2.2); 3.1823(9.8); 7.3562 (9.0); 6.9908 (1.7); 6.9759 (3.6); 6.9611 (1.8); 6.6827 (8.2); 6.6771 (8.8); 6.5537 (4.7); 6.5481 (4.2); 6.5319 (4.4); 6.5262 (4.2); 4.0863 (0.9); 4.0732 (0.9); 3.3112 (99.0); 3.1984 (2.2); 3.1823
(6.6) ; 3.1762 (7.1); 3.1664 (7.5); 3.1633 (8.2); 3.1511 (2.5); 2.8529 (4.2); 2.8369 (8.0); 2.8205 (3.6); 2.6705 (1.0); 2.5236 (2.4); 2.5190 (3.7); 2.5103 (59.4); 2.5058 (130.5); 2.5012 (182.4); 2.4966 (128.5); 2.4921 (58.4); 2.3703 (34.4); 2.3452 (0.9); 2.3278 (1.0); 0.0080 (2.6); -0.0002 (86.8); -0.0086 (2.6). Beispiel Nr. 1.2-54: (6.6); 3.1762 (7.1); 3.1664 (7.5); 3.1633 (8.2); 3.1511 (2.5); 2.8529 (4.2); 2.8369 (8.0); 2.8205 (3.6); 2.6705 (1.0); 2.5236 (2.4); 2.5190 (3.7); 2.5103 (59.4); 2.5058 (130.5); 2.5012 (182.4); 2.4966 (128.5); 2.4921 (58.4); 2.3703 (34.4); 2.3452 (0.9); 2.3278 (1.0); 0.0080 (2.6); -0.0002 (86.8); -0.0086 (2.6). Example No. 1.2-54:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9258 (3.4); 7.9106 (7.6); 7.8964 (3.5); 7.7839 (7.8); 7.7793 (15.9); 7.7746 (11.1); 7.7561 (5.5); 7.7533 (7.4); 7.7491 (4.4); 7.7368 (6.9); 7.7339 (9.3); 7.7299 (6.6); 7.7203 (5.0); 7.7176 (5.6); 7.7152 (4.5); 7.7124 (4.3); 7.7001 (8.1); 7.6974 (7.0); 7.6950 (7.9); 7.6923 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9258 (3.4); 7.9106 (7.6); 7.8964 (3.5); 7.7839 (7.8); 7.7793 (15.9); 7.7746 (11.1); 7.7561 (5.5); 7.7533 (7.4); 7.7491 (4.4); 7.7368 (6.9); 7.7339 (9.3); 7.7299 (6.6); 7.7203 (5.0); 7.7176 (5.6); 7.7152 (4.5); 7.7124 (4.3); 7.7001 (8.1); 7.6974 (7.0); 7.6950 (7.9); 7.6923
(5.7) ; 7.6297 (11.4); 7.6099 (14.6); 7.5902 (5.8); 7.5137 (14.9); 7.4919 (15.6); 7.0110 (3.0); 6.9962 (5.9); 6.9815 (2.9); 6.6956 (14.8); 6.6900 (16.0); 6.5655 (8.2); 6.5598 (7.6); 6.5436 (7.7); 6.5379 (7.2); 5.7538 (0.6); 3.3138 (74.2); 3.2247 (3.5); 3.2088 (11.1); 3.1934 (11.8); 3.1779 (4.3); 2.9338 (4.3); 2.9185 (11.7); 2.9034 (10.8); 2.8879 (3.4); 2.6722 (0.8); 2.5252 (2.2); 2.5205 (3.4); 2.5118 (48.7); 2.5073 (105.2); 2.5027 (146.2); 2.4982 (102.9); 2.4936 (46.8); 2.3301 (0.7); 0.0078 (0.9); -0.0002(5.7); 7.6297 (11.4); 7.6099 (14.6); 7.5902 (5.8); 7.5137 (14.9); 7.4919 (15.6); 7.0110 (3.0); 6.9962 (5.9); 6.9815 (2.9); 6.6956 (14.8); 6.6900 (16.0); 6.5655 (8.2); 6.5598 (7.6); 6.5436 (7.7); 6.5379 (7.2); 5.7538 (0.6); 3.3138 (74.2); 3.2247 (3.5); 3.2088 (11.1); 3.1934 (11.8); 3.1779 (4.3); 2.9338 (4.3); 2.9185 (11.7); 2.9034 (10.8); 2.8879 (3.4); 2.6722 (0.8); 2.5252 (2.2); 2.5205 (3.4); 2.5118 (48.7); 2.5073 (105.2); 2.5027 (146.2); 2.4982 (102.9); 2.4936 (46.8); 2.3301 (0.7); 0.0078 (0.9); -0.0002
(30.4) ; -0.0085 (0.9). (30.4); -0.0085 (0.9).
Beispiel Nr. 1.2-61 : Example No. 1.2-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9696 (1.5); 7.9600 (1.2); 7.9499 (1.6); 7.6216 (2.6); 7.6122 (3.0); 7.5390 (0.7); 7.5281 (1.0); 7.5188 (0.9); 7.5086 (2.3); 7.4975 (0.5); 7.4867 (1.9); 6.9632 (0.9); 6.6618 (1.8); 6.6564 (1.9); 6.5316 (1.0); 6.5263 (0.9); 6.5098 (0.9); 6.5045 (0.9); 4.0397 (0.7); 4.0218 (0.7); 3.3148 (10.5); 3.1914 (1.4); 3.1756 (1.6); 3.1598 (0.6); 2.9968 (0.6); 2.9808 (1.6); 2.9652 (1.5); 2.5072 (11.9); 2.5029 (16.0); 2.4985 (11.6); 1.9892 (2.8); 1.1936 (0.7); 1.1759 (1.4); 1.1581 (0.7); - 0.0002 (2.2). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9696 (1.5); 7.9600 (1.2); 7.9499 (1.6); 7.6216 (2.6); 7.6122 (3.0); 7.5390 (0.7); 7.5281 (1.0); 7.5188 (0.9); 7.5086 (2.3); 7.4975 (0.5); 7.4867 (1.9); 6.9632 (0.9); 6.6618 (1.8); 6.6564 (1.9); 6.5316 (1.0); 6.5263 (0.9); 6.5098 (0.9); 6.5045 (0.9); 4.0397 (0.7); 4.0218 (0.7); 3.3148 (10.5); 3.1914 (1.4); 3.1756 (1.6); 3.1598 (0.6); 2.9968 (0.6); 2.9808 (1.6); 2.9652 (1.5); 2.5072 (11.9); 2.5029 (16.0); 2.4985 (11.6); 1.9892 (2.8); 1.1936 (0.7); 1.1759 (1.4); 1.1581 (0.7); - 0.0002 (2.2).
Beispiel Nr. 1.2-62: Example No. 1.2-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 8.0141 (7.1); 7.8086 (3.8); 7.8043 (4.3); 7.7895 (7.3); 7.78521H-NMR (400.0 MHz, de-DMSO): δ = 8.0141 (7.1); 7.8086 (3.8); 7.8043 (4.3); 7.7895 (7.3); 7.7852
(7.9) ; 7.7706 (4.2); 7.7662 (4.4); 7.7126 (2.0); 7.7081 (2.0); 7.6998 (2.3); 7.6945 (3.7); 7.6917 (3.2); 7.6895 (3.2); 7.6811 (3.2); 7.6767 (3.4); 7.6739 (3.9); 7.6687 (2.5); 7.6605 (2.6); 7.6561 (2.3); 7.5152(7.9); 7.7706 (4.2); 7.7662 (4.4); 7.7126 (2.0); 7.7081 (2.0); 7.6998 (2.3); 7.6945 (3.7); 7.6917 (3.2); 7.6895 (3.2); 7.6811 (3.2); 7.6767 (3.4); 7.6739 (3.9); 7.6687 (2.5); 7.6605 (2.6); 7.6561 (2.3); 7.5152
(14.5) ; 7.4934 (15.3); 7.4277 (4.6); 7.4256 (5.2); 7.4070 (4.5); 7.4047 (4.9); 7.3991 (5.8); 7.3882 (6.9); 7.3857 (5.6); 7.3782 (4.9); 7.3693 (10.6); 7.3667 (9.1); 7.3501 (5.2); 7.3476 (4.6); 7.0105 (3.0); 6.9955 (6.1); 6.9805 (3.0); 6.6878 (14.9); 6.6822 (16.0); 6.5557 (8.3); 6.5501 (7.6); 6.5339 (7.9); 6.5282 (7.5); 4.0570 (0.9); 4.0392 (2.7); 4.0214 (2.7); 4.0036 (0.9); 3.3130 (81.2); 3.2249 (3.4); 3.2087 (10.4); 3.1929 (11.4); 3.1771 (4.6); 3.0074 (6.0); 2.9914 (10.1); 2.9752 (4.4); 2.6759 (0.7); 2.6712 (0.9); 2.6667 (0.7); 2.5247 (2.6); 2.5199 (3.8); 2.5113 (48.2); 2.5068 (103.0); 2.5022 (142.7); 2.4977 (100.9); 2.4931 (46.0); 2.3336 (0.6); 2.3290 (0.8); 2.3244 (0.6); 1.9888 (11.7); 1.2463 (1.0); 1.1932 (3.1); 1.1753 (6.2); 1.1576 (3.0); 0.8581 (1.6); 0.8405 (0.6); 0.0080 (1.7); -0.0002 (51.6); -0.0085 (1.5). Beispiel Nr. 1.2-64: (14.5); 7.4934 (15.3); 7.4277 (4.6); 7.4256 (5.2); 7.4070 (4.5); 7.4047 (4.9); 7.3991 (5.8); 7.3882 (6.9); 7.3857 (5.6); 7.3782 (4.9); 7.3693 (10.6); 7.3667 (9.1); 7.3501 (5.2); 7.3476 (4.6); 7.0105 (3.0); 6.9955 (6.1); 6.9805 (3.0); 6.6878 (14.9); 6.6822 (16.0); 6.5557 (8.3); 6.5501 (7.6); 6.5339 (7.9); 6.5282 (7.5); 4.0570 (0.9); 4.0392 (2.7); 4.0214 (2.7); 4.0036 (0.9); 3.3130 (81.2); 3.2249 (3.4); 3.2087 (10.4); 3.1929 (11.4); 3.1771 (4.6); 3.0074 (6.0); 2.9914 (10.1); 2.9752 (4.4); 2.6759 (0.7); 2.6712 (0.9); 2.6667 (0.7); 2.5247 (2.6); 2.5199 (3.8); 2.5113 (48.2); 2.5068 (103.0); 2.5022 (142.7); 2.4977 (100.9); 2.4931 (46.0); 2.3336 (0.6); 2.3290 (0.8); 2.3244 (0.6); 1.9888 (11.7); 1.2463 (1.0); 1.1932 (3.1); 1.1753 (6.2); 1.1576 (3.0); 0.8581 (1.6); 0.8405 (0.6); 0.0080 (1.7); -0.0002 (51.6); -0.0085 (1.5). Example No. 1.2-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8951 (6.3); 7.6721 (1.1); 7.6528 (4.4); 7.6398 (9.4); 7.6362 (13.4); 7.6274 (9.3); 7.5823 (3.4); 7.5745 (4.3); 7.5526 (4.7); 7.5236 (2.6); 7.5155 (14.1); 7.5068 (2.8); 7.5010 (4.9); 7.4938 (16.0); 7.4782 (2.2); 7.4718 (1.6); 7.0168 (2.5); 7.0017 (4.8); 6.9872 (2.4); 6.6990 (12.0); 6.6934 (13.3); 6.5693 (6.8); 6.5636 (6.4); 6.5474 (6.5); 6.5417 (6.4); 3.3116 (92.5); 3.2236 (3.0); 3.2077 (9.5); 3.1921 (10.3); 3.1765 (3.6); 2.9239 (7.4); 2.9082 (15.0); 2.8924 (5.9); 2.6705 (1.3); 2.5240 (3.2); 2.5193 (4.7); 2.5107 (75.2); 2.5061 (163.9); 2.5015 (228.5); 2.4970 (161.1); 2.4924 (73.3); 2.3280 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8951 (6.3); 7.6721 (1.1); 7.6528 (4.4); 7.6398 (9.4); 7.6362 (13.4); 7.6274 (9.3); 7.5823 (3.4); 7.5745 (4.3); 7.5526 (4.7); 7.5236 (2.6); 7.5155 (14.1); 7.5068 (2.8); 7.5010 (4.9); 7.4938 (16.0); 7.4782 (2.2); 7.4718 (1.6); 7.0168 (2.5); 7.0017 (4.8); 6.9872 (2.4); 6.6990 (12.0); 6.6934 (13.3); 6.5693 (6.8); 6.5636 (6.4); 6.5474 (6.5); 6.5417 (6.4); 3.3116 (92.5); 3.2236 (3.0); 3.2077 (9.5); 3.1921 (10.3); 3.1765 (3.6); 2.9239 (7.4); 2.9082 (15.0); 2.8924 (5.9); 2.6705 (1.3); 2.5240 (3.2); 2.5193 (4.7); 2.5107 (75.2); 2.5061 (163.9); 2.5015 (228.5); 2.4970 (161.1); 2.4924 (73.3); 2.3280
(1.2) ; 0.0080 (2.7); -0.0002 (86.9); -0.0086 (2.5) (1.2); 0.0080 (2.7); -0.0002 (86.9); -0.0086 (2.5)
Beispiel Nr. 1.2-73: Example No. 1.2-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7491 (1.8); 7.5134 (3.1); 7.4919 (3.5); 7.4746 (1.7); 7.3662 (1.8); 7.3468 (1.4); 7.2790 (2.4); 7.2015 (1.3); 7.1972 (1.2); 7.1808 (1.2); 7.1765 (1.1); 7.0072 (0.6); 6.9924 (1.3); 6.9776 (0.7); 6.6968 (2.4); 6.6916 (2.7); 6.5641 (1.3); 6.5587 (1.3); 6.5420 (1.3); 6.53681 H NMR (400.0 MHz, de-DMSO): δ = 7.7491 (1.8); 7.5134 (3.1); 7.4919 (3.5); 7.4746 (1.7); 7.3662 (1.8); 7.3468 (1.4); 7.2790 (2.4); 7.2015 (1.3); 7.1972 (1.2); 7.1808 (1.2); 7.1765 (1.1); 7.0072 (0.6); 6.9924 (1.3); 6.9776 (0.7); 6.6968 (2.4); 6.6916 (2.7); 6.5641 (1.3); 6.5587 (1.3); 6.5420 (1.3); 6.5368
(1.3) ; 4.0391 (0.7); 4.0213 (0.7); 3.8094 (16.0); 3.3149 (5.9); 3.2117 (0.7); 3.1962 (2.3); 3.1805 (2.4); 3.1650 (1.0); 2.8841 (1.4); 2.8685 (2.5); 2.8529 (1.2); 2.5025 (22.9); 2.4983 (18.0); 1.9890 (2.8); 1.1934 (0.8); 1.1756 (1.5); 1.1578 (0.8); -0.0002 (7.9). (1.3); 4.0391 (0.7); 4.0213 (0.7); 3.8094 (16.0); 3.3149 (5.9); 3.2117 (0.7); 3.1962 (2.3); 3.1805 (2.4); 3.1650 (1.0); 2.8841 (1.4); 2.8685 (2.5); 2.8529 (1.2); 2.5025 (22.9); 2.4983 (18.0); 1.9890 (2.8); 1.1934 (0.8); 1.1756 (1.5); 1.1578 (0.8); -0.0002 (7.9).
Beispiel Nr. 1.2-204: Example No. 1.2-204:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.5289 (12.3); 7.5072 (13.0); 7.4551 (0.7); 7.4472 (6.5); 7.4415 (3.8); 7.4342 (5.6); 7.4308 (5.0); 7.4240 (8.8); 7.4150 (1.4); 7.4095 (0.8); 7.3969 (5.6); 7.3898 (5.1); 7.3864 (7.2); 7.3792 (6.1); 7.3734 (11.0); 7.3159 (0.8); 7.3096 (2.7); 7.2973 (12.7); 7.2948 (12.2); 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.5289 (12.3); 7.5072 (13.0); 7.4551 (0.7); 7.4472 (6.5); 7.4415 (3.8); 7.4342 (5.6); 7.4308 (5.0); 7.4240 (8.8); 7.4150 (1.4); 7.4095 (0.8); 7.3969 (5.6); 7.3898 (5.1); 7.3864 (7.2); 7.3792 (6.1); 7.3734 (11.0); 7.3159 (0.8); 7.3096 (2.7); 7.2973 (12.7); 7.2948 (12.2);
7.2913 (9.1); 7.2844 (16.0); 7.2777 (7.7); 7.2740 (8.9); 7.2716 (7.9); 7.2593 (1.6); 7.2531 (0.8); 7.08097.2913 (9.1); 7.2844 (16.0); 7.2777 (7.7); 7.2740 (8.9); 7.2716 (7.9); 7.2593 (1.6); 7.2531 (0.8); 7.0809
(3.0) ; 7.0658 (6.0); 7.0515 (2.8); 6.7812 (14.6); 6.7756 (15.5); 6.7634 (0.7); 6.6349 (8.6); 6.6292 (7.8); 6.6130 (8.2); 6.6074 (7.8); 3.3615 (1.4); 3.3448 (1.2); 3.3105 (491.9); 3.2818 (9.2); 3.2721 (11.4); 3.2690 (11.1); 3.2576 (13.2); 3.2517 (10.4); 3.2408 (14.5); 3.1756 (0.7); 3.1623 (0.8); 3.1424 (3.5); 3.1291 (7.7); 3.1142 (6.8); 3.0816 (10.0); 3.0706 (6.8); 3.0605 (6.6); 3.0537 (6.1); 3.0406 (6.0); 2.9012(3.0); 7.0658 (6.0); 7.0515 (2.8); 6.7812 (14.6); 6.7756 (15.5); 6.7634 (0.7); 6.6349 (8.6); 6.6292 (7.8); 6.6130 (8.2); 6.6074 (7.8); 3.3615 (1.4); 3.3448 (1.2); 3.3105 (491.9); 3.2818 (9.2); 3.2721 (11.4); 3.2690 (11.1); 3.2576 (13.2); 3.2517 (10.4); 3.2408 (14.5); 3.1756 (0.7); 3.1623 (0.8); 3.1424 (3.5); 3.1291 (7.7); 3.1142 (6.8); 3.0816 (10.0); 3.0706 (6.8); 3.0605 (6.6); 3.0537 (6.1); 3.0406 (6.0); 2.9012
(2.1) ; 2.6745 (2.0); 2.6699 (2.7); 2.6652 (1.9); 2.5405 (1.3); 2.5232 (7.5); 2.5185 (11.3); 2.5099 (151.4); 2.5053 (323.4); 2.5008 (445.6); 2.4962 (315.9); 2.4917 (143.4); 2.3321 (2.0); 2.3275 (2.8); 2.3226 (2.5); 0.0080 (2.6); -0.0002 (82.3); -0.0085 (2.4) Beispiel Nr. 1.3-1 : (2.1); 2.6745 (2.0); 2.6699 (2.7); 2.6652 (1.9); 2.5405 (1.3); 2.5232 (7.5); 2.5185 (11.3); 2.5099 (151.4); 2.5053 (323.4); 2,5008 (445.6); 2.4962 (315.9); 2.4917 (143.4); 2.3321 (2.0); 2.3275 (2.8); 2.3226 (2.5); 0.0080 (2.6); -0.0002 (82.3); -0.0085 (2.4) Example No. 1.3-1:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7458 (1.2); 7.7241 (1.3); 7.2872 (0.8); 7.1412 (1.3); 7.0558 (1.3); 7.0505 (1.4); 6.8906 (0.9); 6.8847 (0.8); 6.8688 (0.8); 6.8630 (0.8); 3.3328 (0.6); 3.3137 (5.2); 3.3012 (2.0); 3.2855 (0.8); 3.1150 (1.5); 3.0991 (2.7); 3.0825 (1.1); 2.9118 (16.0); 2.5115 (5.5); 2.5070 (12.1); 2.5024 (17.0); 2.4978 (12.1); 2.4932 (5.6); -0.0002 (7.2) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7458 (1.2); 7.7241 (1.3); 7.2872 (0.8); 7.1412 (1.3); 7.0558 (1.3); 7.0505 (1.4); 6.8906 (0.9); 6.8847 (0.8); 6.8688 (0.8); 6.8630 (0.8); 3.3328 (0.6); 3.3137 (5.2); 3.3012 (2.0); 3.2855 (0.8); 3.1150 (1.5); 3.0991 (2.7); 3.0825 (1.1); 2.9118 (16.0); 2.5115 (5.5); 2.5070 (12.1); 2.5024 (17.0); 2.4978 (12.1); 2.4932 (5.6); -0.0002 (7.2)
Beispiel Nr. 1.3-35: Example No. 1.3-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8913 (2.0); 7.8764 (4.3); 7.8619 (2.1); 7.7844 (11.9); 7.7794 (4.1); 7.7678 (5.0); 7.7628 (16.0); 7.7031 (5.1); 7.6811 (5.2); 7.6343 (16.0); 7.6292 (4.8); 7.6126 (11.4); 7.2105 (1.8); 7.1947 (3.5); 7.1804 (1.7); 6.9557 (5.2); 6.7947 (3.2); 6.7886 (3.1); 6.7727 (3.2); 6.7667 (3.1); 3.3112 (85.9); 3.2680 (2.1); 3.2533 (6.4); 3.2377 (6.7); 3.2220 (2.5); 2.9349 (2.6); 2.9194 (7.0); 2.9047 (6.5); 2.8886 (2.1); 2.6713 (0.9); 2.5107 (59.8); 2.5063 (121.5); 2.5018 (163.0); 2.4972 (115.7); 2.4928 (54.2); 2.3287 (0.9); -0.0002 (29.6). 1 H NMR (400.0 MHz, de-DMSO): δ = 7.8913 (2.0); 7.8764 (4.3); 7.8619 (2.1); 7.7844 (11.9); 7.7794 (4.1); 7.7678 (5.0); 7.7628 (16.0); 7.7031 (5.1); 7.6811 (5.2); 7.6343 (16.0); 7.6292 (4.8); 7.6126 (11.4); 7.2105 (1.8); 7.1947 (3.5); 7.1804 (1.7); 6.9557 (5.2); 6.7947 (3.2); 6.7886 (3.1); 6.7727 (3.2); 6.7667 (3.1); 3.3112 (85.9); 3.2680 (2.1); 3.2533 (6.4); 3.2377 (6.7); 3.2220 (2.5); 2.9349 (2.6); 2.9194 (7.0); 2.9047 (6.5); 2.8886 (2.1); 2.6713 (0.9); 2.5107 (59.8); 2.5063 (121.5); 2.5018 (163.0); 2.4972 (115.7); 2.4928 (54.2); 2.3287 (0.9); -0.0002 (29.6).
Beispiel Nr. 1.3-50: Example No. 1.3-50:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7043 (6.2); 7.6824 (7.6); 7.6705 (14.9); 7.6498 (16.0); 7.3660 (11.4); 7.3461 (10.1); 7.2144 (2.1); 7.1994 (4.0); 7.1837 (2.0); 6.9653 (5.7); 6.9609 (5.7); 6.7918 (3.7); 6.7861 (3.5); 6.7703 (3.5); 6.7645 (3.3); 3.3146 (42.0); 3.2590 (2.7); 3.2429 (7.6); 3.2274 (8.0); 3.2114 (2.8); 2.8801 (3.8); 2.8646 (6.6); 2.8489 (3.1); 2.6726 (0.5); 2.5121 (33.0); 2.5077 (66.3); 2.5031 (88.9); 2.4985 (62.2); 2.4940 (28.2); 2.3625 (38.6); 2.3299 (0.6); 2.0742 (2.0); 0.0079 (1.1); -0.0002 (26.4); - 0.0087 (0.9). Beispiel Nr. 1.3-61 : 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7043 (6.2); 7.6824 (7.6); 7.6705 (14.9); 7.6498 (16.0); 7.3660 (11.4); 7.3461 (10.1); 7.2144 (2.1); 7.1994 (4.0); 7.1837 (2.0); 6.9653 (5.7); 6.9609 (5.7); 6.7918 (3.7); 6.7861 (3.5); 6.7703 (3.5); 6.7645 (3.3); 3.3146 (42.0); 3.2590 (2.7); 3.2429 (7.6); 3.2274 (8.0); 3.2114 (2.8); 2.8801 (3.8); 2.8646 (6.6); 2.8489 (3.1); 2.6726 (0.5); 2.5121 (33.0); 2.5077 (66.3); 2.5031 (88.9); 2.4985 (62.2); 2.4940 (28.2); 2.3625 (38.6); 2.3299 (0.6); 2.0742 (2.0); 0.0079 (1.1); -0.0002 (26.4); - 0.0087 (0.9). Example No. 1.3-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9829 (5.0); 7.9632 (4.6); 7.9617 (5.2); 7.9602 (5.6); 7.9586 (4.6); 7.9438 (4.5); 7.9414 (7.6); 7.9389 (4.5); 7.6982 (5.5); 7.6766 (5.8); 7.6036 (5.8); 7.5999 (12.0); 7.5907 (16.0); 7.5887 (13.1); 7.5800 (1.2); 7.5347 (0.8); 7.5237 (4.3); 7.5144 (3.8); 7.5111 (3.5); 7.5040 (4.3); 7.5020 (3.4); 7.4931 (4.7); 7.4823 (2.6); 7.1937 (1.9); 7.1789 (4.0); 7.1639 (1.9); 6.9293 (5.7); 6.9240 (6.0); 6.7680 (3.5); 6.7624 (3.4); 6.7463 (3.4); 6.7406 (3.2); 4.0906 (1.4); 4.0775 (1.4); 4.0645 (0.5); 3.3193 (36.6); 3.2658 (2.2); 3.2497 (6.8); 3.2341 (7.4); 3.2183 (2.9); 3.1798 (8.2); 3.1670 (7.9); 3.0182 (4.4); 3.0022 (8.0); 2.9860 (3.4); 2.5271 (1.0); 2.5224 (1.5); 2.5137 (18.2); 2.5092 (39.2); 2.5046 (54.6); 2.5000 (38.8); 2.4955 (17.7); 0.0080 (1.0); -0.0002 (32.4); -0.0085 (1.0). Beispiel Nr. 1.3-62: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9829 (5.0); 7.9632 (4.6); 7.9617 (5.2); 7.9602 (5.6); 7.9586 (4.6); 7.9438 (4.5); 7.9414 (7.6); 7.9389 (4.5); 7.6982 (5.5); 7.6766 (5.8); 7.6036 (5.8); 7.5999 (12.0); 7.5907 (16.0); 7.5887 (13.1); 7.5800 (1.2); 7.5347 (0.8); 7.5237 (4.3); 7.5144 (3.8); 7.5111 (3.5); 7.5040 (4.3); 7.5020 (3.4); 7.4931 (4.7); 7.4823 (2.6); 7.1937 (1.9); 7.1.789 (4.0); 7.1639 (1.9); 6.9293 (5.7); 6.9240 (6.0); 6.7680 (3.5); 6.7624 (3.4); 6.7463 (3.4); 6.7406 (3.2); 4.0906 (1.4); 4.0775 (1.4); 4.0645 (0.5); 3.3193 (36.6); 3.2658 (2.2); 3.2497 (6.8); 3.2341 (7.4); 3.2183 (2.9); 3.1798 (8.2); 3.1670 (7.9); 3.0182 (4.4); 3.0022 (8.0); 2.9860 (3.4); 2.5271 (1.0); 2.5224 (1.5); 2.5137 (18.2); 2.5092 (39.2); 2.5046 (54.6); 2,5000 (38,8); 2.4955 (17.7); 0.0080 (1.0); -0.0002 (32.4); -0.0085 (1.0). Example No. 1.3-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 8.0391 (10.1); 7.8012 (3.9); 7.7969 (4.4); 7.7820 (7.7); 7.7777 (8.3); 7.7633 (4.1); 7.7589 (4.6); 7.7067 (8.7); 7.6972 (2.7); 7.6926 (2.8); 7.6847 (11.1); 7.6584 (4.0); 7.6533 (2.6); 7.6450 (2.7); 7.6405 (2.4); 7.4067 (5.4); 7.3859 (5.2); 7.3803 (6.4); 7.3749 (8.0); 7.3723 (5.6); 7.3591 (6.0); 7.3560 (11.8); 7.3533 (9.4); 7.3369 (5.4); 7.3343 (4.8); 7.2284 (3.0); 7.2140 (5.9); 7.1995 (3.0); 6.9539 (9.2); 6.9485 (9.8); 6.7967 (5.7); 6.7911 (5.4); 6.7752 (5.5); 6.7695 (5.1); 3.3151 (43.8); 3.2835 (3.6); 3.2673 (10.9); 3.2516 (11.8); 3.2359 (4.4); 3.0359 (8.3); 3.0200 (16.0); 3.0036 (6.5); 2.6725 (0.6); 2.5258 (2.1); 2.5126 (44.9); 2.5081 (98.3); 2.5035 (137.9); 2.4989 (98.3); 2.4944 (45.2); 2.3302 (0.8); 2.0747 (1.0); 0.0079 (1.4); -0.0002 (44.6); -0.0084 (1.4). 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.0391 (10.1); 7.8012 (3.9); 7.7969 (4.4); 7.7820 (7.7); 7.7777 (8.3); 7.7633 (4.1); 7.7589 (4.6); 7.7067 (8.7); 7.6972 (2.7); 7.6926 (2.8); 7.6847 (11.1); 7.6584 (4.0); 7.6533 (2.6); 7.6450 (2.7); 7.6405 (2.4); 7.4067 (5.4); 7.3859 (5.2); 7.3803 (6.4); 7.3749 (8.0); 7.3723 (5.6); 7.3591 (6.0); 7.3560 (11.8); 7.3533 (9.4); 7.3369 (5.4); 7.3343 (4.8); 7.2284 (3.0); 7.2140 (5.9); 7.1995 (3.0); 6.9539 (9.2); 6.9485 (9.8); 6.7967 (5.7); 6.7911 (5.4); 6.7752 (5.5); 6.7695 (5.1); 3.3151 (43.8); 3.2835 (3.6); 3.2673 (10.9); 3.2516 (11.8); 3.2359 (4.4); 3.0359 (8.3); 3.0200 (16.0); 3.0036 (6.5); 2.6725 (0.6); 2.5258 (2.1); 2.5126 (44.9); 2.5081 (98.3); 2.5035 (137.9); 2.4989 (98.3); 2.4944 (45.2); 2.3302 (0.8); 2.0747 (1.0); 0.0079 (1.4); -0.0002 (44.6); -0.0084 (1.4).
Beispiel Nr. 1.3-204: Example No. 1.3-204:
1H-NMR(400.6 MHz, de-DMSO): δ= 7.7307 (6.8); 7.7091 (7.2); 7.4518 (1.0); 7.4439 (6.4); 7.4375 (3.9); 7.4320 (6.8); 7.4283 (5.8); 7.4206 (10.0); 7.4117 (5.7); 7.3970 (6.0); 7.3896 (4.3); 7.3859 (6.5); 7.3801 (4.0); 7.3736 (7.5); 7.3659 (1.2); 7.3154 (2.9); 7.3056 (4.6); 7.3011 (7.2); 7.2931 (16.0); 7.2874 (10.8); 7.2828 (11.6); 7.2812 (12.0); 7.2766 (7.7); 7.2702 (11.0); 7.2582 (1.5); 7.2513 (0.5); 7.0463 (8.1); 7.0411 (8.7); 6.8851 (5.2); 6.8795 (5.0); 6.8634 (5.0); 6.8578 (4.8); 4.0565 (1.2); 4.0388 (3.5); 4.0210 (3.5); 4.0033 (1.2); 3.3570 (2.0); 3.3286 (175.3); 3.3148 (12.7); 3.2990 (4.4); 3.2887 (6.5);1 H NMR (400.6 MHz, de-DMSO): δ = 7.7307 (6.8); 7.7091 (7.2); 7.4518 (1.0); 7.4439 (6.4); 7.4375 (3.9); 7.4320 (6.8); 7.4283 (5.8); 7.4206 (10.0); 7.4117 (5.7); 7.3970 (6.0); 7.3896 (4.3); 7.3859 (6.5); 7.3801 (4.0); 7.3736 (7.5); 7.3659 (1.2); 7.3154 (2.9); 7.3056 (4.6); 7.3011 (7.2); 7.2931 (16.0); 7.2874 (10.8); 7.2828 (11.6); 7.2812 (12.0); 7.2766 (7.7); 7.2702 (11.0); 7.2582 (1.5); 7.2513 (0.5); 7.0463 (8.1); 7.0411 (8.7); 6.8851 (5.2); 6.8795 (5.0); 6.8634 (5.0); 6.8578 (4.8); 4.0565 (1.2); 4.0388 (3.5); 4.0210 (3.5); 4.0033 (1.2); 3.3570 (2.0); 3.3286 (175.3); 3.3148 (12.7); 3.2990 (4.4); 3.2887 (6.5);
3.2760 (6.4); 3.2682 (6.5); 3.2589 (6.9); 3.2477 (9.5); 3.1596 (7.5); 3.1439 (13.5); 3.1277 (5.4); 3.0813 (8.8); 3.0703 (6.1); 3.0597 (6.2); 3.0534 (5.6); 3.0402 (5.6); 2.6768 (0.5); 2.6721 (0.7); 2.6675 (0.5); 2.5323 (1.7); 2.5261 (2.4); 2.5213 (3.4); 2.5123 (40.2); 2.5079 (86.2); 2.5033 (120.5); 2.4988 (87.8); 2.4943 (41.6); 2.3304 (0.7); 1.9895 (15.8); 1.2787 (1.1); 1.2438 (4.8); 1.1933 (4.5); 1.1756 (8.8); 1.1578 (4.2); 0.8747 (2.2); 0.8581 (7.7); 0.8404 (2.9); -0.0002 (7.6). 3.2760 (6.4); 3.2682 (6.5); 3.2589 (6.9); 3.2477 (9.5); 3.1596 (7.5); 3.1439 (13.5); 3.1277 (5.4); 3.0813 (8.8); 3.0703 (6.1); 3.0597 (6.2); 3.0534 (5.6); 3.0402 (5.6); 2.6768 (0.5); 2.6721 (0.7); 2.6675 (0.5); 2.5323 (1.7); 2.5261 (2.4); 2.5213 (3.4); 2.5123 (40.2); 2.5079 (86.2); 2.5033 (120.5); 2.4988 (87.8); 2.4943 (41.6); 2.3304 (0.7); 1.9895 (15.8); 1.2787 (1.1); 1.2438 (4.8); 1.1933 (4.5); 1.1756 (8.8); 1.1578 (4.2); 0.8747 (2.2); 0.8581 (7.7); 0.8404 (2.9); -0.0002 (7.6).
Beispiel Nr. 1.4-1 : Example No. 1.4-1:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.3941 (2.1); 7.3728 (2.2); 7.1064 (1.0); 6.6063 (0.9); 6.5413 (1.4); 6.5364 (1.8); 6.5064 (1.2); 6.5007 (0.9); 6.4851 (1.1); 6.4793 (0.9); 3.3151 (13.0); 3.2453 (0.5); 3.2292 (1.6); 3.2131 (1.8); 3.1974 (0.8); 3.1030 (0.8); 3.0872 (1.9); 3.0713 (1.8); 3.0550 (0.5); 2.9023 (16.0); 2.5106 (3.6); 2.5060 (7.8); 2.5015 (10.9); 2.4969 (7.9); 2.4924 (3.7); 2.3214 (10.1); -0.0002 (2.3). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.3941 (2.1); 7.3728 (2.2); 7.1064 (1.0); 6.6063 (0.9); 6.5413 (1.4); 6.5364 (1.8); 6.5064 (1.2); 6.5007 (0.9); 6.4851 (1.1); 6.4793 (0.9); 3.3151 (13.0); 3.2453 (0.5); 3.2292 (1.6); 3.2131 (1.8); 3.1974 (0.8); 3.1030 (0.8); 3.0872 (1.9); 3.0713 (1.8); 3.0550 (0.5); 2.9023 (16.0); 2.5106 (3.6); 2.5060 (7.8); 2.5015 (10.9); 2.4969 (7.9); 2.4924 (3.7); 2.3214 (10.1); -0.0002 (2.3).
Beispiel Nr. 1.4-4: Example No. 1.4-4:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.3930 (2.4); 7.3717 (2.5); 7.1100 (0.6); 7.0951 (1.2); 7.0804 (0.6); 6.5962 (0.5); 6.5818 (1.1); 6.5675 (0.6); 6.5327 (1.9); 6.5279 (2.3); 6.4961 (1.5); 6.4904 (1.1); 6.4748 (1.4); 6.4690 (1.2); 3.3133 (27.8); 3.2225 (0.7); 3.2069 (2.1); 3.1877 (2.3); 3.1747 (1.1); 3.1702 (1.8); 3.1531 (1.2); 3.1022 (0.9); 3.0860 (1.9); 3.0701 (1.7); 3.0538 (0.6); 2.5191 (0.5); 2.5104 (7.4); 2.5059 (16.1); 2.5013 (22.5); 2.4967 (16.0); 2.4922 (7.4); 2.3201 (13.2); 1.6845 (2.0); 1.6768 (2.1); 1.2149 (16.0); 1.1979 (15.8); -0.0002 (4.4). 1H NMR (400.0 MHz, de-DMSO): δ = 7.3930 (2.4); 7.3717 (2.5); 7.1100 (0.6); 7.0951 (1.2); 7.0804 (0.6); 6.5962 (0.5); 6.5818 (1.1); 6.5675 (0.6); 6.5327 (1.9); 6.5279 (2.3); 6.4961 (1.5); 6.4904 (1.1); 6.4748 (1.4); 6.4690 (1.2); 3.3133 (27.8); 3.2225 (0.7); 3.2069 (2.1); 3.1877 (2.3); 3.1747 (1.1); 3.1702 (1.8); 3.1531 (1.2); 3.1022 (0.9); 3.0860 (1.9); 3.0701 (1.7); 3.0538 (0.6); 2.5191 (0.5); 2.5104 (7.4); 2.5059 (16.1); 2.5013 (22.5); 2.4967 (16.0); 2.4922 (7.4); 2.3201 (13.2); 1.6845 (2.0); 1.6768 (2.1); 1.2149 (16.0); 1.1979 (15.8); -0.0002 (4.4).
Beispiel Nr. 1.4-34: Example No. 1.4-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8692 (0.8); 7.8616 (8.1); 7.8562 (3.3); 7.8485 (8.8); 7.8441 (4.1); 7.8392 (9.0); 7.8315 (3.6); 7.8262 (8.6); 7.8184 (1.1); 7.7858 (3.6); 7.4400 (1.0); 7.4322 (8.5); 7.4269 (2.5); 7.4150 (3.0); 7.4100 (16.0); 7.4048 (3.0); 7.3930 (2.5); 7.3878 (7.6); 7.3802 (0.8); 7.3601 (8.8); 7.3389 (9.2); 6.5418 (1.9); 6.5267 (3.9); 6.5121 (1.8); 6.4366 (7.6); 6.4202 (5.1); 6.4144 (3.2); 6.3989 (4.4); 6.3932 (3.4); 3.3148 (34.6); 3.1772 (3.0); 3.1647 (8.4); 3.1486 (7.3); 3.1328 (2.9); 2.8902 (5.4); 2.8737 (9.9); 2.8572 (4.3); 2.6714 (0.6); 2.5248 (1.5); 2.5115 (31.6); 2.5069 (68.6); 2.5023 (95.4); 2.4978 (67.2); 2.4932 (30.4); 2.3293 (0.6); 2.2994 (42.5); 0.0080 (1.0); -0.0002 (32.7); -0.0085 (1.0). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8692 (0.8); 7.8616 (8.1); 7.8562 (3.3); 7.8485 (8.8); 7.8441 (4.1); 7.8392 (9.0); 7.8315 (3.6); 7.8262 (8.6); 7.8184 (1.1); 7.7858 (3.6); 7.4400 (1.0); 7.4322 (8.5); 7.4269 (2.5); 7.4150 (3.0); 7.4100 (16.0); 7.4048 (3.0); 7.3930 (2.5); 7.3878 (7.6); 7.3802 (0.8); 7.3601 (8.8); 7.3389 (9.2); 6.5418 (1.9); 6.5267 (3.9); 6.5121 (1.8); 6.4366 (7.6); 6.4202 (5.1); 6.4144 (3.2); 6.3989 (4.4); 6.3932 (3.4); 3.3148 (34.6); 3.1772 (3.0); 3.1647 (8.4); 3.1486 (7.3); 3.1328 (2.9); 2.8902 (5.4); 2.8737 (9.9); 2.8572 (4.3); 2.6714 (0.6); 2.5248 (1.5); 2.5115 (31.6); 2.5069 (68.6); 2.5023 (95.4); 2.4978 (67.2); 2.4932 (30.4); 2.3293 (0.6); 2.2994 (42.5); 0.0080 (1.0); -0.0002 (32.7); -0.0085 (1.0).
Beispiel Nr. 1.4-35: Example No. 1.4-35:
'H-NMR^OO.O MHZ, de-DMSO): δ= 7.8444 (3.9); 7.7979 (1.3); 7.7915 (11.7); 7.7864 (3.8); 7.7748 (4.4); 7.7697 (16.0); 7.7634 (2.0); 7.6547 (1.8); 7.6484 (15.6); 7.6433 (4.2); 7.6316 (3.6); 7.6267 (11.3); 7.6203 (1.2); 7.3559 (6.6); 7.3347 (7.0); 6.5258 (1.5); 6.5109 (2.9); 6.4960 (1.5); 6.4259 (5.6); 6.4107 (3.9); 6.4050 (2.4); 6.3893 (3.4); 6.3838 (2.7); 3.3140 (31.7); 3.1771 (1.8); 3.1608 (5.2); 3.1451 (5.6); 3.1292 (2.2); 2.9024 (3.7); 2.8862 (6.8); 2.8699 (2.9); 2.5250 (1.0); 2.5202 (1.6); 2.5115 (24.6); 2.5069 (54.4); 2.5023 (76.2); 2.4977 (53.9); 2.4932 (24.5); 2.3006 (31.7); 2.0738 (11.9); 0.0080 (0.8); -0.0002 (26.5); -0.0085 (0.8). 'H-NMR ^ OO.O MHZ, de-DMSO): δ = 7.8444 (3.9); 7.7979 (1.3); 7.7915 (11.7); 7.7864 (3.8); 7.7748 (4.4); 7.7697 (16.0); 7.7634 (2.0); 7.6547 (1.8); 7.6484 (15.6); 7.6433 (4.2); 7.6316 (3.6); 7.6267 (11.3); 7.6203 (1.2); 7.3559 (6.6); 7.3347 (7.0); 6.5258 (1.5); 6.5109 (2.9); 6.4960 (1.5); 6.4259 (5.6); 6.4107 (3.9); 6.4050 (2.4); 6.3893 (3.4); 6.3838 (2.7); 3.3140 (31.7); 3.1771 (1.8); 3.1608 (5.2); 3.1451 (5.6); 3.1292 (2.2); 2.9024 (3.7); 2.8862 (6.8); 2.8699 (2.9); 2.5250 (1.0); 2.5202 (1.6); 2.5115 (24.6); 2.5069 (54.4); 2.5023 (76.2); 2.4977 (53.9); 2.4932 (24.5); 2.3006 (31.7); 2.0738 (11.9); 0.0080 (0.8); -0.0002 (26.5); -0.0085 (0.8).
Beispiel Nr. 1.4-40: Example No. 1.4-40:
1H-NMR(400.0 MHz, de-DMSO): δ = 7.7264 (3.9); 7.7212 (1.1); 7.7093 (1.1); 7.7040 (4.2); 7.3583 (2.0); 7.3371 (2.1); 7.0988 (3.9); 7.0936 (1.1); 7.0817 (1.0); 7.0765 (3.6); 6.5197 (0.9); 6.4387 (1.3); 6.4338 (1.7); 6.4157 (1.1); 6.4100 (0.7); 6.3944 (1.0); 6.3887 (0.8); 3.8248 (16.0); 3.3164 (4.7); 3.1662 (0.5); 3.1501 (1.5); 3.1340 (1.6); 3.1179 (0.6); 2.8266 (1.0); 2.5118 (4.8); 2.5072 (10.4); 2.5026 (14.6); 2.4981 (10.3); 2.4935 (4.7); 2.2984 (9.5); -0.0002 (6.2). Beispiel Nr. 1.4-50: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7264 (3.9); 7.7212 (1.1); 7.7093 (1.1); 7.7040 (4.2); 7.3583 (2.0); 7.3371 (2.1); 7.0988 (3.9); 7.0936 (1.1); 7.0817 (1.0); 7.0765 (3.6); 6.5197 (0.9); 6.4387 (1.3); 6.4338 (1.7); 6.4157 (1.1); 6.4100 (0.7); 6.3944 (1.0); 6,387 (0.8); 3.8248 (16.0); 3.3164 (4.7); 3.1662 (0.5); 3.1501 (1.5); 3.1340 (1.6); 3.1179 (0.6); 2.8266 (1.0); 2.5118 (4.8); 2.5072 (10.4); 2.5026 (14.6); 2.4981 (10.3); 2.4935 (4.7); 2.2984 (9.5); -0.0002 (6.2). Example No. 1.4-50:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.6792 (12.3); 7.6585 (16.0); 7.6444 (4.4); 7.6302 (2.0); 7.3840 (10.4); 7.3640 (9.3); 7.3570 (9.3); 7.3358 (8.7); 6.5354 (1.8); 6.5215 (3.6); 6.5059 (1.8); 6.4333 (6.9); 6.4113 (4.6); 6.4056 (3.2); 6.3898 (4.1); 6.3842 (3.3); 3.3118 (60.0); 3.1765 (0.9); 3.1637 (2.6); 3.1484 (6.3); 3.1322 (6.5); 3.1159 (2.6); 2.8576 (2.4); 2.8417 (5.8); 2.8261 (5.5); 2.8100 (2.0); 2.6699 (0.7); 2.5237 (1.7); 2.5103 (43.5); 2.5057 (95.4); 2.5012 (133.4); 2.4966 (94.8); 2.4921 (43.6); 2.4510 (0.6); 2.3706 (36.2); 2.3278 (0.8); 2.2965 (39.5); 0.0080 (1.3); -0.0002 (44.6); -0.0083 (1.4) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.6792 (12.3); 7.6585 (16.0); 7.6444 (4.4); 7.6302 (2.0); 7.3840 (10.4); 7.3640 (9.3); 7.3570 (9.3); 7.3358 (8.7); 6.5354 (1.8); 6.5215 (3.6); 6.5059 (1.8); 6.4333 (6.9); 6.4113 (4.6); 6.4056 (3.2); 6.3898 (4.1); 6.3842 (3.3); 3.3118 (60.0); 3.1765 (0.9); 3.1637 (2.6); 3.1484 (6.3); 3.1322 (6.5); 3.1159 (2.6); 2.8576 (2.4); 2.8417 (5.8); 2.8261 (5.5); 2.8100 (2.0); 2.6699 (0.7); 2.5237 (1.7); 2.5103 (43.5); 2.5057 (95.4); 2.5012 (133.4); 2.4966 (94.8); 2.4921 (43.6); 2.4510 (0.6); 2.3706 (36.2); 2.3278 (0.8); 2.2965 (39.5); 0.0080 (1.3); -0.0002 (44.6); -0.0083 (1.4)
Beispiel Nr. 1.4-54: Example No. 1.4-54:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9169 (3.5); 7.9024 (7.6); 7.8880 (3.5); 7.7925 (7.7); 7.7880 (16.0); 7.7834 (10.9); 7.7608 (5.7); 7.7580 (7.4); 7.7538 (4.7); 7.7415 (6.8); 7.7387 (9.3); 7.7345 (7.0); 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9169 (3.5); 7.9024 (7.6); 7.8880 (3.5); 7.7925 (7.7); 7.7880 (16.0); 7.7834 (10.9); 7.7608 (5.7); 7.7580 (7.4); 7.7538 (4.7); 7.7415 (6.8); 7.7387 (9.3); 7.7345 (7.0);
7.7245 (5.1); 7.7218 (5.8); 7.7193 (4.6); 7.7166 (4.7); 7.7044 (8.3); 7.7017 (7.2); 7.6992 (8.2); 7.69657.7245 (5.1); 7.7218 (5.8); 7.7193 (4.6); 7.7166 (4.7); 7.7044 (8.3); 7.7017 (7.2); 7.6992 (8.2); 7.6965
(6.1); 7.6325 (11.1); 7.6127 (14.8); 7.5930 (5.8); 7.3593 (13.4); 7.3380 (13.9); 6.5503 (2.9); 6.5353(6.1); 7.6325 (11.1); 7.6127 (14.8); 7.5930 (5.8); 7.3593 (13.4); 7.3380 (13.9); 6.5503 (2.9); 6.5353
(5.9); 6.5207 (2.9); 6.4468 (8.3); 6.4417 (11.0); 6.4230 (7.3); 6.4173 (4.9); 6.4017 (6.6); 6.3959 (5.3);(5.9); 6.5207 (2.9); 6.4468 (8.3); 6.4417 (11.0); 6.4230 (7.3); 6.4173 (4.9); 6.4017 (6.6); 6.3959 (5.3);
3.3153 (62.0); 3.1896 (3.4); 3.1732 (10.2); 3.1576 (11.1); 3.1418 (4.3); 2.9295 (4.5); 2.9137 (11.4); 2.8982 (10.5); 2.8820 (3.5); 2.6719 (0.7); 2.5251 (1.8); 2.5205 (2.6); 2.5118 (41.4); 2.5073 (91.5);3.3153 (62.0); 3.1896 (3.4); 3.1732 (10.2); 3.1576 (11.1); 3.1418 (4.3); 2.9295 (4.5); 2.9137 (11.4); 2.8982 (10.5); 2.8820 (3.5); 2.6719 (0.7); 2.5251 (1.8); 2.5205 (2.6); 2.5118 (41.4); 2.5073 (91.5);
2.5027 (129.0); 2.4981 (91.5); 2.4936 (41.5); 2.3295 (0.8); 2.3022 (62.1); 2.0742 (0.8); 0.0081 (1.5); -2.5027 (129.0); 2.4981 (91.5); 2.4936 (41.5); 2.3295 (0.8); 2.3022 (62.1); 2.0742 (0.8); 0.0081 (1.5); -
0.0002 (49.3); -0.0086 (1.6). Beispiel Nr. 1.4-61 : 0.0002 (49.3); -0.0086 (1.6). Example No. 1.4-61:
1H-NMR(400.0 MHz, de-DMSO): δ = 7.9775 (10.2); 7.9591 (10.1); 7.9569 (9.0); 7.6415 (1.5); 7.6318 (15.1); 7.6294 (16.0); 7.6224 (11.7); 7.6189 (9.8); 7.6153 (8.2); 7.5989 (1.0); 7.5953 (1.4); 7.5550 (1.0); 7.5439 (4.9); 7.5352 (4.5); 7.5308 (3.7); 7.5242 (5.1); 7.5166 (4.2); 7.5103 (3.2); 7.5026 (3.1); 7.3546 (10.7); 7.3333 (11.3); 6.5189 (2.4); 6.5047 (5.0); 6.4897 (2.4); 6.4080 (9.2); 6.3855 (5.9); 6.3799 (4.2); 6.3642 (5.4); 6.3583 (4.3); 3.3127 (65.4); 3.1686 (2.6); 3.1520 (7.5); 3.1349 (7.6); 3.1190 (3.8); 2.9678 (5.7); 2.6711 (0.8); 2.5243 (2.2); 2.5108 (49.5); 2.5063 (107.5); 2.5017 (150.2); 2.4971 (106.8); 2.4926 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9775 (10.2); 7.9591 (10.1); 7.9569 (9.0); 7.6415 (1.5); 7.6318 (15.1); 7.6294 (16.0); 7.6224 (11.7); 7.6189 (9.8); 7.6153 (8.2); 7.5989 (1.0); 7.5953 (1.4); 7.5550 (1.0); 7.5439 (4.9); 7.5352 (4.5); 7.5308 (3.7); 7.5242 (5.1); 7.5166 (4.2); 7.5103 (3.2); 7.5026 (3.1); 7.3546 (10.7); 7.3333 (11.3); 6.5189 (2.4); 6.5047 (5.0); 6.4897 (2.4); 6.4080 (9.2); 6.3855 (5.9); 6.3799 (4.2); 6.3642 (5.4); 6.3583 (4.3); 3.3127 (65.4); 3.1686 (2.6); 3.1520 (7.5); 3.1349 (7.6); 3.1190 (3.8); 2.9678 (5.7); 2.6711 (0.8); 2.5243 (2.2); 2.5108 (49.5); 2.5063 (107.5); 2.5017 (150.2); 2.4971 (106.8); 2.4926
(48.7) ; 2.3282 (1.0); 2.2959 (51.8); 2.0734 (13.0); 0.0080 (1.5); -0.0002 (53.3); -0.0085 (1.5). (48.7); 2.3282 (1.0); 2.2959 (51.8); 2.0734 (13.0); 0.0080 (1.5); -0.0002 (53.3); -0.0085 (1.5).
Beispiel Nr. 1.4-62: Example No. 1.4-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9999 (4.3); 7.8149 (4.0); 7.8103 (4.6); 7.7955 (8.1); 7.7912 (8.9); 7.7766 (4.7); 7.7720 (4.9); 7.7147 (2.2); 7.7102 (2.1); 7.7018 (2.4); 7.6959 (4.1); 7.6761 (4.6); 7.6708 (2.9); 7.6628 (2.9); 7.6582 (2.6); 7.4313 (5.6); 7.4103 (5.5); 7.4049 (6.6); 7.3919 (7.6); 7.3893 (6.9); 7.3841 (5.6); 7.3728 (11.9); 7.3595 (15.4); 7.3539 (6.5); 7.3382 (16.0); 6.5471 (3.3); 6.5317 (6.9); 6.5169 (3.4); 6.4322 (12.9); 6.4095 (8.3); 6.4037 (6.1); 6.3882 (7.5); 6.3827 (6.1); 3.3110 (105.8); 3.1862 (3.6); 3.1694 (11.0); 3.1532 (11.3); 3.1369 (5.2); 3.0046 (9.5); 2.9872 (14.8); 2.9707 (6.4); 2.6704 (1.6); 2.5236 (3.6); 2.5102 (89.6); 2.5057 (197.2); 2.5012 (278.0); 2.4966 (199.7); 2.4921 (93.3); 2.4553 (1.0); 2.3281 (1.8); 2.2981 (73.2); 0.0080 (2.5); -0.0002 (85.0); -0.0085 (2.9). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9999 (4.3); 7.8149 (4.0); 7.8103 (4.6); 7.7955 (8.1); 7.7912 (8.9); 7.7766 (4.7); 7.7720 (4.9); 7.7147 (2.2); 7.7102 (2.1); 7.7018 (2.4); 7.6959 (4.1); 7.6761 (4.6); 7.6708 (2.9); 7.6628 (2.9); 7.6582 (2.6); 7.4313 (5.6); 7.4103 (5.5); 7.4049 (6.6); 7.3919 (7.6); 7.3893 (6.9); 7.3841 (5.6); 7.3728 (11.9); 7.3595 (15.4); 7.3539 (6.5); 7.3382 (16.0); 6.5471 (3.3); 6.5317 (6.9); 6.5169 (3.4); 6.4322 (12.9); 6.4095 (8.3); 6.4037 (6.1); 6.3882 (7.5); 6.3827 (6.1); 3.3110 (105.8); 3.1862 (3.6); 3.1694 (11.0); 3.1532 (11.3); 3.1369 (5.2); 3.0046 (9.5); 2.9872 (14.8); 2.9707 (6.4); 2.6704 (1.6); 2.5236 (3.6); 2.5102 (89.6); 2.5057 (197.2); 2.5012 (278.0); 2.4966 (199.7); 2.4921 (93.3); 2.4553 (1.0); 2.3281 (1.8); 2.2981 (73.2); 0.0080 (2.5); -0.0002 (85.0); -0.0085 (2.9).
Beispiel Nr. 1.4-64: Example No. 1.4-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8872 (8.9); 7.6758 (1.0); 7.6562 (4.8); 7.6414 (14.8); 7.6323 (10.9); 7.5822 (5.8); 7.5614 (5.5); 7.5270 (2.6); 7.5199 (3.7); 7.5113 (2.9); 7.5040 (5.0); 7.4977 (3.7); 7.4868 (2.9); 7.4752 (1.8); 7.3598 (11.1); 7.3386 (11.9); 6.5537 (3.0); 6.5399 (6.2); 6.5245 (3.4); 6.4449 (12.0); 6.4256 (7.4); 6.4045 (6.6); 6.3990 (5.6); 3.3143 (33.2); 3.1880 (3.7); 3.1720 (10.8); 3.1564 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8872 (8.9); 7.6758 (1.0); 7.6562 (4.8); 7.6414 (14.8); 7.6323 (10.9); 7.5822 (5.8); 7.5614 (5.5); 7.5270 (2.6); 7.5199 (3.7); 7.5113 (2.9); 7.5040 (5.0); 7.4977 (3.7); 7.4868 (2.9); 7.4752 (1.8); 7.3598 (11.1); 7.3386 (11.9); 6.5537 (3.0); 6.5399 (6.2); 6.5245 (3.4); 6.4449 (12.0); 6.4256 (7.4); 6.4045 (6.6); 6.3990 (5.6); 3.3143 (33.2); 3.1880 (3.7); 3.1720 (10.8); 3.1564
(11.8) ; 3.1402 (5.0); 2.9222 (8.8); 2.9061 (16.0); 2.8896 (7.3); 2.6702 (0.7); 2.5062 (93.2); 2.5022 (126.2); 2.4978 (96.0); 2.2996 (59.3); 2.0739 (3.4); -0.0002 (30.1) (11.8); 3.1402 (5.0); 2.9222 (8.8); 2.9061 (16.0); 2.8896 (7.3); 2.6702 (0.7); 2.5062 (93.2); 2.5022 (126.2); 2.4978 (96.0); 2.2996 (59.3); 2.0739 (3.4); -0.0002 (30.1)
Beispiel Nr. 1.4-73: Example No. 1.4-73:
1H-NMR(400.0 MHz, d6-DMSO): δ= 7.7451 (1.0); 7.5196 (1.0); 7.4997 (2.1); 7.4797 (1.6); 7.3720 (1.4); 7.3682 (1.2); 7.3580 (2.2); 7.3512 (1.1); 7.3369 (2.2); 7.2933 (1.4); 7.2872 (1.8); 7.2829 (1.4); 7.2060 (1.0); 7.2013 (0.9); 7.1872 (0.9); 7.1808 (0.8); 6.5319 (1.0); 6.5172 (0.5); 6.4411 (1.8); 6.4210 (1.2); 6.4150 (0.8); 6.3995 (1.1); 6.3937 (0.8); 3.8084 (16.0); 3.3137 (11.4); 3.1758 (0.6); 3.1597 (1.6); 3.1436 (1.7); 3.1277 (0.7); 2.8811 (0.9); 2.8652 (1.5); 2.8489 (0.7); 2.5109 (8.2); 2.5064 (17.4); 2.5018 (23.8); 2.4973 (16.9); 2.4928 (7.8); 2.2982 (10.1); 2.0733 (0.5); -0.0002 (7.9). Beispiel Nr. 1.4-92: 1H-NMR (400.0 MHz, d6-DMSO): δ = 7.7451 (1.0); 7.5196 (1.0); 7.4997 (2.1); 7.4797 (1.6); 7.3720 (1.4); 7.3682 (1.2); 7.3580 (2.2); 7.3512 (1.1); 7.3369 (2.2); 7.2933 (1.4); 7.2872 (1.8); 7.2829 (1.4); 7.2060 (1.0); 7.2013 (0.9); 7.1872 (0.9); 7.1808 (0.8); 6.5319 (1.0); 6.5172 (0.5); 6.4411 (1.8); 6.4210 (1.2); 6.4150 (0.8); 6.3995 (1.1); 6.3937 (0.8); 3.8084 (16.0); 3.3137 (11.4); 3.1758 (0.6); 3.1597 (1.6); 3.1436 (1.7); 3.1277 (0.7); 2.8811 (0.9); 2.8652 (1.5); 2.8489 (0.7); 2.5109 (8.2); 2.5064 (17.4); 2.5018 (23.8); 2.4973 (16.9); 2.4928 (7.8); 2.2982 (10.1); 2.0733 (0.5); -0.0002 (7.9). Example No. 1.4-92:
1H-NMR(400.6 MHz, de-DMSO): δ= 7.7826 (3.1); 7.7799 (3.4); 7.7308 (3.8); 7.7277 (3.6); 7.5261 (0.7); 7.3780 (2.6); 7.3567 (2.7); 6.5718 (0.7); 6.5571 (1.4); 6.5425 (0.7); 6.4810 (2.0); 6.4764 (2.3); 6.4376 (1.5); 6.4321 (1.2); 6.4163 (1.3); 6.4107 (1.2); 3.6837 (16.0); 3.3321 (12.4); 3.3315 (12.3); 3.1876 (0.7); 3.1716 (1.9); 3.1547 (2.0); 3.1386 (0.9); 2.9557 (1.6); 2.5121 (4.2); 2.5077 (8.4); 2.5032 (11.3); 2.4987 (8.2); 2.4943 (3.8); 2.3113 (12.7); -0.0002 (1.6) 1 H-NMR (400.6 MHz, de-DMSO): δ = 7.7826 (3.1); 7.7799 (3.4); 7.7308 (3.8); 7.7277 (3.6); 7.5261 (0.7); 7.3780 (2.6); 7.3567 (2.7); 6.5718 (0.7); 6.5571 (1.4); 6.5425 (0.7); 6.4810 (2.0); 6.4764 (2.3); 6.4376 (1.5); 6.4321 (1.2); 6.4163 (1.3); 6.4107 (1.2); 3.6837 (16.0); 3.3321 (12.4); 3.3315 (12.3); 3.1876 (0.7); 3.1716 (1.9); 3.1547 (2.0); 3.1386 (0.9); 2.9557 (1.6); 2.5121 (4.2); 2.5077 (8.4); 2.5032 (11.3); 2.4987 (8.2); 2.4943 (3.8); 2.3113 (12.7); -0.0002 (1.6)
Beispiel Nr. 1.4-204: Example No. 1.4-204:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.4544 (0.8); 7.4467 (6.2); 7.4403 (3.4); 7.4348 (6.3); 7.4310 (4.8); 7.4235 (8.3); 7.4147 (1.3); 7.4110 (0.9); 7.3951 (1.0); 7.3864 (5.4); 7.3762 (16.0); 7.3693 (5.0); 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.4544 (0.8); 7.4467 (6.2); 7.4403 (3.4); 7.4348 (6.3); 7.4310 (4.8); 7.4235 (8.3); 7.4147 (1.3); 7.4110 (0.9); 7.3951 (1.0); 7.3864 (5.4); 7.3762 (16.0); 7.3693 (5.0);
7.3631 (8.8); 7.3553 (14.0); 7.3133 (0.8); 7.3063 (2.7); 7.3017 (1.8); 7.2945 (14.3); 7.2879 (8.6); 7.28307.3631 (8.8); 7.3553 (14.0); 7.3133 (0.8); 7.3063 (2.7); 7.3017 (1.8); 7.2945 (14.3); 7.2879 (8.6); 7.2830
(10.0); 7.2816 (10.0); 7.2770 (7.2); 7.2708 (11.0); 7.2585 (1.4); 7.2517 (0.5); 6.6207 (2.5); 6.6061 (5.2);(10.0); 7.2816 (10.0); 7.2770 (7.2); 7.2708 (11.0); 7.2585 (1.4); 7.2517 (0.5); 6.6207 (2.5); 6.6061 (5.2);
6.5915 (2.5); 6.5309 (7.7); 6.5260 (9.7); 6.4991 (6.4); 6.4934 (4.9); 6.4777 (5.8); 6.4720 (5.0); 3.31626.5915 (2.5); 6.5309 (7.7); 6.5260 (9.7); 6.4991 (6.4); 6.4934 (4.9); 6.4777 (5.8); 6.4720 (5.0); 3.3162
(88.9); 3.2736 (5.7); 3.2606 (8.4); 3.2551 (7.0); 3.2525 (7.4); 3.2436 (13.6); 3.2318 (15.3); 3.2140 (4.2); 3.1778 (0.5); 3.1647 (0.6); 3.1411 (5.9); 3.1254 (8.5); 3.1090 (3.5); 3.0834 (8.8); 3.0726 (6.2); 3.0619(88.9); 3.2736 (5.7); 3.2606 (8.4); 3.2551 (7.0); 3.2525 (7.4); 3.2436 (13.6); 3.2318 (15.3); 3.2140 (4.2); 3.1778 (0.5); 3.1647 (0.6); 3.1411 (5.9); 3.1254 (8.5); 3.1090 (3.5); 3.0834 (8.8); 3.0726 (6.2); 3.0619
(5.7); 3.0555 (5.4); 3.0423 (5.2); 2.6712 (0.6); 2.5246 (1.8); 2.5199 (2.5); 2.5113 (31.2); 2.5067 (68.0);(5.7); 3.0555 (5.4); 3.0423 (5.2); 2.6712 (0.6); 2.5246 (1.8); 2.5199 (2.5); 2.5113 (31.2); 2.5067 (68.0);
2.5021 (94.7); 2.4975 (67.4); 2.4930 (30.9); 2.3335 (0.6); 2.3289 (0.8); 2.3241 (0.8); 2.3171 (2.3);2.5021 (94.7); 2.4975 (67.4); 2.4930 (30.9); 2.3335 (0.6); 2.3289 (0.8); 2.3241 (0.8); 2.3171 (2.3);
2.3043 (54.0); 0.0080 (0.6); -0.0002 (18.4); -0.0085 (0.5). Beispiel Nr. 1.6-1 : 2.3043 (54.0); 0.0080 (0.6); -0.0002 (18.4); -0.0085 (0.5). Example No. 1.6-1:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.3140 (2.4); 7.2929 (2.5); 7.1370 (1.0); 6.7419 (0.9); 6.2687 (1.7); 6.2639 (2.4); 6.2498 (1.6); 6.2448 (1.0); 6.2285 (1.4); 6.2235 (1.1); 3.8200 (13.8); 3.3107 (10.1); 3.2757 (0.5); 3.2594 (1.6); 3.2433 (1.7); 3.2271 (0.8); 3.1103 (0.8); 3.0939 (1.8); 3.0778 (1.7); 3.0620 (0.5); 2.9126 (16.0); 2.5099 (7.8); 2.5053 (17.0); 2.5008 (23.9); 2.4962 (17.1); 2.4917 (7.9); -0.0002 (7.5). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.3140 (2.4); 7.2929 (2.5); 7.1370 (1.0); 6.7419 (0.9); 6.2687 (1.7); 6.2639 (2.4); 6.2498 (1.6); 6.2448 (1.0); 6.2285 (1.4); 6.2235 (1.1); 3.8200 (13.8); 3.3107 (10.1); 3.2757 (0.5); 3.2594 (1.6); 3.2433 (1.7); 3.2271 (0.8); 3.1103 (0.8); 3.0939 (1.8); 3.0778 (1.7); 3.0620 (0.5); 2.9126 (16.0); 2.5099 (7.8); 2.5053 (17.0); 2.5008 (23.9); 2.4962 (17.1); 2.4917 (7.9); -0.0002 (7.5).
Beispiel Nr. 1.6-4: Example No. 1.6-4:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.3121 (2.9); 7.2910 (2.8); 7.1416 (0.6); 7.1268 (1.2); 7.1120 (0.6); 6.7401 (0.5); 6.7254 (1.1); 6.7108 (0.6); 6.2601 (1.9); 6.2553 (2.6); 6.2407 (1.9); 6.2358 (1.7); 6.2314 (0.6); 6.2196 (1.7); 6.2146 (1.3); 3.8222 (16.0); 3.3138 (26.2); 3.2557 (0.7); 3.2394 (1.8); 3.2216 (2.1); 3.2045 (1.7); 3.1873 (1.5); 3.1703 (1.1); 3.1078 (0.8); 3.0911 (1.7); 3.0752 (1.7); 3.0592 (0.6); 2.5191 (0.6); 2.5104 (7.1); 2.5059 (15.3); 2.5013 (21.3); 2.4967 (15.2); 2.4922 (7.0); 1.6867 (2.4); 1.6768 (2.5); 1.2181 (15.0); 1.2011 (14.8); -0.0002 (3.8). Beispiel Nr. 1.6-34: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.3121 (2.9); 7.2910 (2.8); 7.1416 (0.6); 7.1268 (1.2); 7.1120 (0.6); 6.7401 (0.5); 6.7254 (1.1); 6.7108 (0.6); 6.2601 (1.9); 6.2553 (2.6); 6.2407 (1.9); 6.2358 (1.7); 6.2314 (0.6); 6.2196 (1.7); 6.2146 (1.3); 3.8222 (16.0); 3.3138 (26.2); 3.2557 (0.7); 3.2394 (1.8); 3.2216 (2.1); 3.2045 (1.7); 3.1873 (1.5); 3.1703 (1.1); 3.1078 (0.8); 3.0911 (1.7); 3.0752 (1.7); 3.0592 (0.6); 2.5191 (0.6); 2.5104 (7.1); 2.5059 (15.3); 2.5013 (21.3); 2.4967 (15.2); 2.4922 (7.0); 1.6867 (2.4); 1.6768 (2.5); 1.2181 (15.0); 1.2011 (14.8); -0.0002 (3.8). Example No. 1.6-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8663 (2.2); 7.8609 (1.1); 7.8533 (2.6); 7.8443 (2.6); 7.8310 (2.6); 7.4389 (2.4); 7.4167 (4.4); 7.3945 (2.0); 7.2859 (2.8); 7.2648 (2.9); 6.6717 (1.3); 6.1803 (2.7); 6.1704 (2.0); 6.1489 (1.6); 6.1440 (1.1); 3.7977 (16.0); 3.3092 (76.6); 3.1989 (1.9); 3.1842 (1.9); 3.1670 (0.8); 2.8836 (1.9); 2.6696 (1.0); 2.5231 (2.9); 2.5097 (56.2); 2.5052 (120.0); 2.5006 (165.5); 2.4960 (115.2); 2.4915 (51.7); 2.3275 (0.9); 0.0081 (2.1); -0.0002 (68.0); -0.0085 (1.8). Beispiel Nr. 1.6-35: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8663 (2.2); 7.8609 (1.1); 7.8533 (2.6); 7.8443 (2.6); 7.8310 (2.6); 7.4389 (2.4); 7.4167 (4.4); 7.3945 (2.0); 7.2859 (2.8); 7.2648 (2.9); 6.6717 (1.3); 6.1803 (2.7); 6.1704 (2.0); 6.1489 (1.6); 6.1440 (1.1); 3.7977 (16.0); 3.3092 (76.6); 3.1989 (1.9); 3.1842 (1.9); 3.1670 (0.8); 2.8836 (1.9); 2.6696 (1.0); 2.5231 (2.9); 2.5097 (56.2); 2.5052 (120.0); 2,5006 (165.5); 2.4960 (115.2); 2.4915 (51.7); 2.3275 (0.9); 0.0081 (2.1); -0.0002 (68.0); -0.0085 (1.8). Example No. 1.6-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8073 (0.6); 7.8009 (4.4); 7.7960 (1.6); 7.7843 (1.7); 7.7792 (6.0); 7.7729 (0.8); 7.6647 (0.7); 7.6585 (5.8); 7.6534 (1.6); 7.6417 (1.3); 7.6368 (4.2); 7.2850 (2.8); 7.2639 (3.0); 6.6760 (0.6); 6.6613 (1.1); 6.6465 (0.5); 6.1788 (1.9); 6.1742 (2.8); 6.1651 (2.0); 6.1601 (1.0); 6.1438 (1.6); 6.1389 (1.2); 3.8004 (16.0); 3.3161 (11.9); 3.2152 (0.6); 3.1991 (1.9); 3.1833 (2.0); 3.1782 (1.7); 3.1653 (1.6); 2.9163 (1.5); 2.9001 (2.8); 2.8837 (1.2); 2.5119 (7.7); 2.5073 (17.0); 2.5027 (23.8); 2.4982 (17.0); 2.4936 (7.7); 2.0741 (4.1); -0.0002 (9.2) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8073 (0.6); 7.8009 (4.4); 7.7960 (1.6); 7.7843 (1.7); 7.7792 (6.0); 7.7729 (0.8); 7.6647 (0.7); 7.6585 (5.8); 7.6534 (1.6); 7.6417 (1.3); 7.6368 (4.2); 7.2850 (2.8); 7.2639 (3.0); 6.6760 (0.6); 6.6613 (1.1); 6.6465 (0.5); 6.1788 (1.9); 6.1742 (2.8); 6.1651 (2.0); 6.1601 (1.0); 6.1438 (1.6); 6.1389 (1.2); 3.8004 (16.0); 3.3161 (11.9); 3.2152 (0.6); 3.1991 (1.9); 3.1833 (2.0); 3.1782 (1.7); 3.1653 (1.6); 2.9163 (1.5); 2.9001 (2.8); 2.8837 (1.2); 2.5119 (7.7); 2.5073 (17.0); 2.5027 (23.8); 2.4982 (17.0); 2.4936 (7.7); 2.0741 (4.1); -0.0002 (9.2)
Beispiel Nr. 1.6-40: Example No. 1.6-40:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7282 (3.8); 7.7230 (1.1); 7.7111 (1.2); 7.7059 (4.1); 7.2840 (2.2); 7.2629 (2.4); 7.1005 (3.9); 7.0953 (1.1); 7.0833 (1.0); 7.0781 (3.6); 6.6584 (0.9); 6.1802 (1.5); 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7282 (3.8); 7.7230 (1.1); 7.7111 (1.2); 7.7059 (4.1); 7.2840 (2.2); 7.2629 (2.4); 7.1005 (3.9); 7.0953 (1.1); 7.0833 (1.0); 7.0.781 (3.6); 6.6584 (0.9); 6.1802 (1.5);
6.1755 (2.2); 6.1661 (1.5); 6.1612 (0.8); 6.1449 (1.2); 6.1399 (1.0); 3.8246 (16.0); 3.7964 (12.6); 3.3152 (10.0); 3.2022 (0.5); 3.1859 (1.4); 3.1777 (1.4); 3.1699 (1.5); 3.1647 (1.4); 3.1538 (0.6); 2.8588 (0.8); 2.8417 (1.4); 2.8252 (0.7); 2.5112 (6.4); 2.5067 (13.9); 2.5021 (19.4); 2.4975 (13.7); 2.4930 (6.2); 2.0735 (2.4); -0.0002 (8.3). 6.1755 (2.2); 6.1661 (1.5); 6.1612 (0.8); 6.1449 (1.2); 6.1399 (1.0); 3.8246 (16.0); 3.7964 (12.6); 3.3152 (10.0); 3.2022 (0.5); 3.1859 (1.4); 3.1777 (1.4); 3.1699 (1.5); 3.1647 (1.4); 3.1538 (0.6); 2.8588 (0.8); 2.8417 (1.4); 2.8252 (0.7); 2.5112 (6.4); 2.5067 (13.9); 2.5021 (19.4); 2.4975 (13.7); 2.4930 (6.2); 2.0735 (2.4); -0.0002 (8.3).
Beispiel Nr. 1.6-50: Example No. 1.6-50:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.6822 (4.2); 7.6779 (1.9); 7.6659 (2.2); 7.6616 (4.8); 7.3841 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.6822 (4.2); 7.6779 (1.9); 7.6659 (2.2); 7.6616 (4.8); 7.3841
(3.3) ; 7.3642 (3.0); 7.2836 (2.8); 7.2625 (3.0); 6.6740 (0.6); 6.6592 (1.2); 6.6445 (0.6); 6.1783 (2.0); 6.1737 (2.9); 6.1636 (1.9); 6.1587 (1.1); 6.1424 (1.6); 6.1374 (1.2); 3.7947 (16.0); 3.3158 (14.8); 3.2045 (0.7); 3.1883 (2.0); 3.1779 (3.0); 3.1724 (2.2); 3.1649 (2.6); 3.1562 (0.8); 2.8687 (0.9); 2.8529 (1.5); 2.8374 (0.7); 2.5112 (6.4); 2.5066 (13.5); 2.5021 (18.4); 2.4975 (13.1); 2.4931 (5.9); 2.3712 (11.3); 2.0733 (2.3); -0.0002 (9.9) (3.3); 7.3642 (3.0); 7.2836 (2.8); 7.2625 (3.0); 6.6740 (0.6); 6.6592 (1.2); 6.6445 (0.6); 6.1783 (2.0); 6.1737 (2.9); 6.1636 (1.9); 6.1587 (1.1); 6.1424 (1.6); 6.1374 (1.2); 3.7947 (16.0); 3.3158 (14.8); 3.2045 (0.7); 3.1883 (2.0); 3.1779 (3.0); 3.1724 (2.2); 3.1649 (2.6); 3.1562 (0.8); 2.8687 (0.9); 2.8529 (1.5); 2.8374 (0.7); 2.5112 (6.4); 2.5066 (13.5); 2.5021 (18.4); 2.4975 (13.1); 2.4931 (5.9); 2.3712 (11.3); 2.0733 (2.3); -0.0002 (9.9)
Beispiel Nr. 1.6-54: Example No. 1.6-54:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7979 (1.5); 7.7926 (3.2); 7.7882 (2.1); 7.7650 (1.3); 7.76221 H NMR (400.0 MHz, de-DMSO): δ = 7.7979 (1.5); 7.7926 (3.2); 7.7882 (2.1); 7.7650 (1.3); 7.7622
(1.4) ; 7.7428 (1.8); 7.7387 (1.3); 7.7270 (1.1); 7.7094 (1.6); 7.7040 (1.7); 7.6371 (2.2); 7.6174 (2.8); 7.5975 (1.1); 7.2848 (2.8); 7.2636 (2.9); 6.6785 (1.1); 6.1806 (3.0); 6.1728 (2.1); 6.1515 (1.6); 6.1464 (1.2); 3.7992 (16.0); 3.3095 (93.3); 3.2069 (2.1); 3.1913 (2.2); 3.1751 (1.4); 3.1621 (0.7); 2.9315 (1.4); 2.9165 (2.7); 2.9002 (1.1); 2.6700 (1.0); 2.5232 (2.8); 2.5184 (4.1); 2.5097 (57.3); 2.5051 (124.4); 2.5006 (173.5); 2.4960 (122.8); 2.4915 (55.5); 2.3273 (0.9); 0.0080 (1.8); -0.0002 (63.1); -0.0085 (2.0). Beispiel Nr. 1.6-61 : (1.4); 7.7428 (1.8); 7.7387 (1.3); 7.7270 (1.1); 7.7094 (1.6); 7.7040 (1.7); 7.6371 (2.2); 7.6174 (2.8); 7.5975 (1.1); 7.2848 (2.8); 7.2636 (2.9); 6.6785 (1.1); 6.1806 (3.0); 6.1728 (2.1); 6.1515 (1.6); 6.1464 (1.2); 3.7992 (16.0); 3.3095 (93.3); 3.2069 (2.1); 3.1913 (2.2); 3.1751 (1.4); 3.1621 (0.7); 2.9315 (1.4); 2.9165 (2.7); 2.9002 (1.1); 2,60700 (1.0); 2.5232 (2.8); 2.5184 (4.1); 2.5097 (57.3); 2.5051 (124.4); 2,5006 (173.5); 2.4960 (122.8); 2.4915 (55.5); 2.3273 (0.9); 0.0080 (1.8); -0.0002 (63.1); -0.0085 (2.0). Example No. 1.6-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9757 (2.3); 7.9538 (2.1); 7.6319 (4.5); 7.6254 (3.3); 7.6203 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9757 (2.3); 7.9538 (2.1); 7.6319 (4.5); 7.6254 (3.3); 7.6203
(2.5) ; 7.6167 (2.4); 7.5454 (1.1); 7.5378 (1.2); 7.5238 (1.4); 7.5107 (0.9); 7.5042 (0.9); 7.2797 (2.8); 7.2585 (3.1); 6.6512 (1.5); 6.1526 (3.2); 6.1361 (1.8); 6.1154 (1.7); 3.7962 (16.0); 3.3104 (53.8); 3.1906 (2.2); 3.1743 (2.4); 3.1592 (1.2); 2.9960 (1.9); 2.9791 (2.9); 2.9617 (1.5); 2.6699 (0.6); 2.5051 (82.9); 2.5006 (119.9); 2.4962 (93.8); 2.3269 (0.6); 0.0080 (1.2); -0.0002 (35.9). (2.5); 7.6167 (2.4); 7.5454 (1.1); 7.5378 (1.2); 7.5238 (1.4); 7.5107 (0.9); 7.5042 (0.9); 7.2797 (2.8); 7.2585 (3.1); 6.6512 (1.5); 6.1526 (3.2); 6.1361 (1.8); 6.1154 (1.7); 3.7962 (16.0); 3.3104 (53.8); 3.1906 (2.2); 3.1743 (2.4); 3.1592 (1.2); 2.9960 (1.9); 2.9791 (2.9); 2.9617 (1.5); 2.6699 (0.6); 2.5051 (82.9); 2,5006 (119.9); 2.4962 (93.8); 2.3269 (0.6); 0.0080 (1.2); -0.0002 (35.9).
Beispiel Nr. 1.6-62: Example No. 1.6-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 8.0404 (0.9); 7.8201 (0.7); 7.8158 (0.8); 7.8010 (1.4); 7.7967 (1.5); 7.7821 (0.8); 7.7777 (0.8); 7.6996 (0.7); 7.6974 (0.6); 7.6950 (0.6); 7.6867 (0.6); 7.6823 (0.6); 7.6792 (0.7); 7.4405 (0.8); 7.4382 (1.0); 7.4173 (0.9); 7.4139 (0.9); 7.4116 (1.0); 7.3966 (1.4); 7.3938 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.0404 (0.9); 7.8201 (0.7); 7.8158 (0.8); 7.8010 (1.4); 7.7967 (1.5); 7.7821 (0.8); 77777 (0.8); 7.6996 (0.7); 7.6974 (0.6); 7.6950 (0.6); 7.6867 (0.6); 7.6823 (0.6); 7.6792 (0.7); 7.4405 (0.8); 7.4382 (1.0); 7.4173 (0.9); 7.4139 (0.9); 7.4116 (1.0); 7.3966 (1.4); 7.3938
(1.7) ; 7.3909 (0.9); 7.3775 (1.9); 7.3749 (1.7); 7.3585 (1.0); 7.3558 (0.9); 7.2873 (2.9); 7.2661 (3.1); 6.6947 (0.5); 6.6796 (1.1); 6.6649 (0.6); 6.1816 (1.9); 6.1768 (2.7); 6.1642 (1.8); 6.1592 (1.1); 6.1430(1.7); 7.3909 (0.9); 7.3775 (1.9); 7.3749 (1.7); 7.3585 (1.0); 7.3558 (0.9); 7.2873 (2.9); 7.2661 (3.1); 6.6947 (0.5); 6.6796 (1.1); 6.6649 (0.6); 6.1816 (1.9); 6.1768 (2.7); 6.1642 (1.8); 6.1592 (1.1); 6.1430
(1.6) ; 6.1379 (1.2); 3.8008 (16.0); 3.3156 (8.4); 3.2271 (0.6); 3.2111 (1.6); 3.1948 (1.7); 3.1783 (0.9); 3.0049 (1.4); 2.5118 (6.8); 2.5073 (14.9); 2.5027 (20.9); 2.4981 (14.8); 2.4935 (6.7); -0.0002 (11.6) (1.6); 6.1379 (1.2); 3.8008 (16.0); 3.3156 (8.4); 3.2271 (0.6); 3.2111 (1.6); 3.1948 (1.7); 3.1783 (0.9); 3.0049 (1.4); 2.5118 (6.8); 2.5073 (14.9); 2.5027 (20.9); 2.4981 (14.8); 2.4935 (6.7); -0.0002 (11.6)
Beispiel Nr. 1.6-64: Example No. 1.6-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.6608 (1.0); 7.6483 (2.5); 7.6449 (2.8); 7.6360 (2.2); 7.5875 (1.0); 7.5656 (0.9); 7.5300 (0.5); 7.5230 (0.8); 7.5172 (0.5); 7.5140 (0.5); 7.5070 (1.0); 7.5010 (0.7); 7.4968 (0.6); 7.4895 (0.6); 7.2853 (2.8); 7.2642 (2.9); 6.6953 (0.6); 6.6805 (1.2); 6.6659 (0.6); 6.1894 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.6608 (1.0); 7.6483 (2.5); 7.6449 (2.8); 7.6360 (2.2); 7.5875 (1.0); 7.5656 (0.9); 7.5300 (0.5); 7.5230 (0.8); 7.5172 (0.5); 7.5140 (0.5); 7.5070 (1.0); 7.5010 (0.7); 7.4968 (0.6); 7.4895 (0.6); 7.2853 (2.8); 7.2642 (2.9); 6.6953 (0.6); 6.6805 (1.2); 6.6659 (0.6); 6.1894
(1.8) ; 6.1847 (2.8); 6.1755 (2.0); 6.1704 (1.0); 6.1542 (1.6); 6.1492 (1.3); 3.7984 (16.0); 3.3101 (36.3); 3.2246 (0.7); 3.2082 (1.9); 3.1922 (2.1); 3.1763 (0.9); 2.9347 (1.3); 2.9188 (2.3); 2.9014 (1.0); 2.5234 (1.2); 2.5186 (1.7); 2.5100 (23.5); 2.5055 (50.4); 2.5009 (69.7); 2.4963 (49.2); 2.4918 (22.2); 2.3277 (0.5); 0.0081 (1.0); -0.0002 (28.4); -0.0085 (0.8) (1.8); 6.1847 (2.8); 6.1755 (2.0); 6.1704 (1.0); 6.1542 (1.6); 6.1492 (1.3); 3.7984 (16.0); 3.3101 (36.3); 3.2246 (0.7); 3.2082 (1.9); 3.1922 (2.1); 3.1763 (0.9); 2.9347 (1.3); 2.9188 (2.3); 2.9014 (1.0); 2.5234 (1.2); 2.5186 (1.7); 2,5100 (23.5); 2.5055 (50.4); 2,5009 (69.7); 2.4963 (49.2); 2.4918 (22.2); 2.3277 (0.5); 0.0081 (1.0); -0.0002 (28.4); -0.0085 (0.8)
Beispiel Nr. 1.6-73: Example No. 1.6-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7733 (0.6); 7.5219 (1.0); 7.5020 (2.0); 7.4820 (1.6); 7.3771 (0.9); 7.3747 (1.2); 7.3708 (1.1); 7.3579 (0.8); 7.3538 (1.0); 7.3515 (0.8); 7.2953 (1.4); 7.2892 (1.8); 7.2843 (3.3); 7.2629 (2.3); 7.2098 (0.9); 7.2077 (1.0); 7.2033 (0.8); 7.2012 (0.8); 7.1891 (0.8); 7.1869 (0.8); 7.1826 (0.8); 7.1805 (0.7); 6.6716 (0.9); 6.1873 (1.5); 6.1826 (2.2); 6.1721 (1.5); 6.1671 (0.8); 6.1509 (1.2); 6.1458 (1.0); 3.8101 (16.0); 3.7975 (12.5); 3.3127 (11.7); 3.1973 (1.4); 3.1814 (1.5); 3.1652 (0.6); 2.8858 (1.0); 2.8727 (1.0); 2.5107 (7.9); 2.5062 (17.3); 2.5016 (24.0); 2.4970 (17.0); 2.4925 (7.8); -0.0002 (9.4). Beispiel Nr. 1.6-92: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7733 (0.6); 7.5219 (1.0); 7.5020 (2.0); 7.4820 (1.6); 7.3771 (0.9); 7.3747 (1.2); 7.3708 (1.1); 7.3579 (0.8); 7.3538 (1.0); 7.3515 (0.8); 7.2953 (1.4); 7.2892 (1.8); 7.2843 (3.3); 7.2629 (2.3); 7.2098 (0.9); 7.2077 (1.0); 7.2033 (0.8); 7.2012 (0.8); 7.1891 (0.8); 7.1869 (0.8); 7.1826 (0.8); 7.1805 (0.7); 6.6716 (0.9); 6.1873 (1.5); 6.1826 (2.2); 6.1721 (1.5); 6.1671 (0.8); 6.1509 (1.2); 6.1458 (1.0); 3.8101 (16.0); 3.7975 (12.5); 3.3127 (11.7); 3.1973 (1.4); 3.1814 (1.5); 3.1652 (0.6); 2.8858 (1.0); 2.8727 (1.0); 2.5107 (7.9); 2.5062 (17.3); 2.5016 (24.0); 2.4970 (17.0); 2.4925 (7.8); -0.0002 (9.4). Example No. 1.6-92:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7756 (3.5); 7.7270 (3.8); 7.7240 (3.4); 7.5579 (0.8); 7.5428 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7756 (3.5); 7.7270 (3.8); 7.7240 (3.4); 7.5579 (0.8); 7.5428
(1.7) ; 7.5284 (0.8); 7.2965 (2.8); 7.2751 (3.0); 6.7075 (0.6); 6.6938 (1.4); 6.6789 (0.7); 6.2356 (2.5); 6.2308 (2.8); 6.1853 (1.7); 6.1804 (1.4); 6.1639 (1.6); 6.1590 (1.4); 3.8139 (15.6); 3.6838 (16.0); 3.3121 (12.8); 3.2275 (0.7); 3.2113 (1.8); 3.1947 (1.9); 3.1780 (1.0); 2.9969 (0.9); 2.9816 (1.9); 2.9638 (1.9); 2.9477 (0.8); 2.5099 (13.4); 2.5056 (27.9); 2.5011 (38.3); 2.4967 (28.2); 2.4922 (14.1); -0.0002 (7.4). Beispiel Nr. 1.13-73: (1.7); 7.5284 (0.8); 7.2965 (2.8); 7.2751 (3.0); 6.7075 (0.6); 6.6938 (1.4); 6.6789 (0.7); 6.2356 (2.5); 6.2308 (2.8); 6.1853 (1.7); 6.1804 (1.4); 6.1639 (1.6); 6.1590 (1.4); 3.8139 (15.6); 3.6838 (16.0); 3.3121 (12.8); 3.2275 (0.7); 3.2113 (1.8); 3.1947 (1.9); 3.1780 (1.0); 2.9969 (0.9); 2.9816 (1.9); 2.9638 (1.9); 2.9477 (0.8); 2.5099 (13.4); 2.5056 (27.9); 2.5011 (38.3); 2.4967 (28.2); 2.4922 (14.1); -0.0002 (7.4). Example No. 1.13-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7682 (1.5); 7.6210 (1.8); 7.5988 (1.9); 7.5020 (1.1); 7.4820 (2.4); 7.4621 (1.8); 7.3701 (1.8); 7.3508 (1.4); 7.2861 (2.5); 7.1852 (1.4); 7.1789 (1.3); 7.1645 (1.3); 7.1583 (1.1); 7.0255 (2.2); 6.9022 (0.7); 6.8869 (1.4); 6.8722 (0.8); 6.7941 (1.1); 6.7723 (1.1); 3.7976 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7682 (1.5); 7.6210 (1.8); 7.5988 (1.9); 7.5020 (1.1); 7.4820 (2.4); 7.4621 (1.8); 7.3701 (1.8); 7.3508 (1.4); 7.2861 (2.5); 7.1852 (1.4); 7.1789 (1.3); 7.1645 (1.3); 7.1583 (1.1); 7.0255 (2.2); 6.9022 (0.7); 6.8869 (1.4); 6.8722 (0.8); 6.7941 (1.1); 6.7723 (1.1); 3.7976
(16.0) ; 3.3195 (16.1); 3.2422 (0.8); 3.2267 (2.3); 3.2111 (2.5); 3.1953 (1.0); 3.1801 (1.2); 3.1671 (1.2); 2.9162 (1.2); 2.9013 (2.2); 2.8865 (1.2); 2.5043 (21.5); 2.5003 (17.1); -0.0002 (3.0). (16.0); 3.3195 (16.1); 3.2422 (0.8); 3.2267 (2.3); 3.2111 (2.5); 3.1953 (1.0); 3.1801 (1.2); 3.1671 (1.2); 2.9162 (1.2); 2.9013 (2.2); 2.8865 (1.2); 2.5043 (21.5); 2.5003 (17.1); -0.0002 (3.0).
Beispiel Nr. 1.23-34: Example No. 1.23-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8696 (1.0); 7.8618 (8.3); 7.8566 (3.4); 7.8488 (8.9); 7.8441 (4.6); 7.8396 (9.2); 7.8318 (3.8); 7.8266 (8.6); 7.8188 (1.2); 7.7846 (3.9); 7.4264 (1.0); 7.4186 (8.6); 7.4133 (2.7); 7.3965 (16.0); 7.3915 (3.1); 7.3795 (2.6); 7.3743 (7.6); 7.3666 (0.9); 7.3264 (6.5); 7.3044 (7.0); 6.8914 (7.6); 6.8844 (8.3); 6.7420 (3.8); 6.7348 (3.6); 6.7200 (3.6); 6.7130 (3.3); 6.2942 (2.1); 6.2790 (4.3); 6.2642 (2.2); 3.3184 (30.7); 3.1644 (2.7); 3.1480 (7.7); 3.1322 (8.2); 3.1163 (3.2); 2.8970 (6.4); 2.8808 (11.7); 2.8643 (4.9); 2.5132 (26.3); 2.5087 (55.5); 2.5042 (75.9); 2.4996 (53.7); 2.4951 (24.7); 0.0080 (0.5); -0.0002 (14.7). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8696 (1.0); 7.8618 (8.3); 7.8566 (3.4); 7.8488 (8.9); 7.8441 (4.6); 7.8396 (9.2); 7.8318 (3.8); 7.8266 (8.6); 7.8188 (1.2); 7.7846 (3.9); 7.4264 (1.0); 7.4186 (8.6); 7.4133 (2.7); 7.3965 (16.0); 7.3915 (3.1); 7.3795 (2.6); 7.3743 (7.6); 7.3666 (0.9); 7.3264 (6.5); 7.3044 (7.0); 6.8914 (7.6); 6.8844 (8.3); 6.7420 (3.8); 6.7348 (3.6); 6.7200 (3.6); 6.7130 (3.3); 6.2942 (2.1); 6.2790 (4.3); 6.2642 (2.2); 3.3184 (30.7); 3.1644 (2.7); 3.1480 (7.7); 3.1322 (8.2); 3.1163 (3.2); 2.8970 (6.4); 2.8808 (11.7); 2.8643 (4.9); 2.5132 (26.3); 2.5087 (55.5); 2.5042 (75.9); 2.4996 (53.7); 2.4951 (24.7); 0.0080 (0.5); -0.0002 (14.7).
Beispiel Nr. 1.23-35: Example No. 1.23-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8615 (1.7); 7.8470 (3.8); 7.8324 (1.8); 7.8021 (1.4); 7.7958 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8615 (1.7); 7.8470 (3.8); 7.8324 (1.8); 7.8021 (1.4); 7.7958
(12.1) ; 7.7907 (3.9); 7.7791 (4.4); 7.7739 (16.0); 7.7676 (1.9); 7.6490 (1.9); 7.6427 (15.6); 7.6376 (4.2); 7.6259 (3.7); 7.6209 (11.2); 7.6146 (1.2); 7.3240 (4.6); 7.3020 (4.9); 6.8937 (5.6); 6.8867 (5.9); 6.7341 (2.7); 6.7271 (2.6); 6.7122 (2.5); 6.7050 (2.4); 6.2892 (1.5); 6.2742 (2.9); 6.2592 (1.4); 3.3134 (15.7); 3.1620 (1.8); 3.1456 (5.3); 3.1298 (5.8); 3.1141 (2.2); 2.9132 (2.4); 2.8974 (6.0); 2.8821 (5.5); 2.8660 (1.8); 2.5258 (1.1); 2.5210 (1.7); 2.5124 (24.0); 2.5078 (51.8); 2.5032 (71.8); 2.4986 (50.2); 2.4941 (22.4); 0.0080 (0.6); -0.0002 (20.2); -0.0085 (0.6). Beispiel Nr. 1.23-40: (12.1); 7.7907 (3.9); 7.7791 (4.4); 7.7739 (16.0); 7.7676 (1.9); 7.6490 (1.9); 7.6427 (15.6); 7.6376 (4.2); 7.6259 (3.7); 7.6209 (11.2); 7.6146 (1.2); 7.3240 (4.6); 7.3020 (4.9); 6.8937 (5.6); 6.8867 (5.9); 6.7341 (2.7); 6.7271 (2.6); 6.7122 (2.5); 6.7050 (2.4); 6.2892 (1.5); 6.2742 (2.9); 6.2592 (1.4); 3.3134 (15.7); 3.1620 (1.8); 3.1456 (5.3); 3.1298 (5.8); 3.1141 (2.2); 2.9132 (2.4); 2.8974 (6.0); 2.8821 (5.5); 2.8660 (1.8); 2.5258 (1.1); 2.5210 (1.7); 2.5124 (24.0); 2.5078 (51.8); 2.5032 (71.8); 2.4986 (50.2); 2.4941 (22.4); 0.0080 (0.6); -0.0002 (20.2); -0.0085 (0.6). Example No. 1.23-40:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7240 (3.8); 7.7187 (1.1); 7.7068 (1.2); 7.7016 (4.1); 7.5641 (1.0); 7.3241 (1.3); 7.3020 (1.4); 7.0873 (3.8); 7.0820 (1.1); 7.0701 (1.0); 7.0649 (3.5); 6.8965 (1.6); 6.8895 (1.8); 6.7337 (0.8); 6.7269 (0.8); 6.7119 (0.8); 6.7049 (0.7); 3.8195 (16.0); 3.3304 (1.4); 3.1298 (1.0); 3.1171 (1.0); 2.8550 (0.7); 2.8392 (1.7); 2.8233 (1.6); 2.8071 (0.6); 2.5119 (6.6); 2.5074 (14.0); 2.5028 (19.3); 2.4982 (13.5); 2.4937 (6.0); -0.0002 (7.0) Beispiel Nr. 1.23-54: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7240 (3.8); 7.7187 (1.1); 7.7068 (1.2); 7.7016 (4.1); 7.5641 (1.0); 7.3241 (1.3); 7.3020 (1.4); 7.0873 (3.8); 7.0820 (1.1); 7.0701 (1.0); 7.0649 (3.5); 6.8965 (1.6); 6.8895 (1.8); 6.7337 (0.8); 6.7269 (0.8); 6.7119 (0.8); 6.7049 (0.7); 3.8195 (16.0); 3.3304 (1.4); 3.1298 (1.0); 3.1171 (1.0); 2.8550 (0.7); 2.8392 (1.7); 2.8233 (1.6); 2.8071 (0.6); 2.5119 (6.6); 2.5074 (14.0); 2.5028 (19.3); 2.4982 (13.5); 2.4937 (6.0); -0.0002 (7.0) Example No. 1.23-54:
'H-NMR^OO.O MHZ, de-DMSO): δ= 7.9017 (6.5); 7.7904 (7.8); 7.7859 (16.0); 7.7815 (10.8); 7.7589 'H-NMR ^ OO.O MHZ, de-DMSO): δ = 7.9017 (6.5); 7.7904 (7.8); 7.7859 (16.0); 7.7815 (10.8); 7.7589
(6.2) ; 7.7561 (7.9); 7.7547 (6.0); 7.7518 (5.3); 7.7396 (7.6); 7.7368 (9.4); 7.7354 (8.1); 7.7325 (7.2); 7.7074 (5.0); 7.7047 (5.8); 7.7022 (4.8); 7.6994 (4.9); 7.6873 (8.6); 7.6845 (7.7); 7.6820 (8.5); 7.6793 (6.6); 7.6204 (11.4); 7.6005 (15.6); 7.5808 (6.0); 7.3246 (9.0); 7.3026 (9.8); 6.8969 (11.3); 6.8899(6.2); 7.7561 (7.9); 7.7547 (6.0); 7.7518 (5.3); 7.7396 (7.6); 7.7368 (9.4); 7.7354 (8.1); 7.7325 (7.2); 7.7074 (5.0); 7.7047 (5.8); 7.7022 (4.8); 7.6994 (4.9); 7.6873 (8.6); 7.6845 (7.7); 7.6820 (8.5); 7.6793 (6.6); 7.6204 (11.4); 7.6005 (15.6); 7.5808 (6.0); 7.3246 (9.0); 7.3026 (9.8); 6.8969 (11.3); 6.8899
(12.2) ; 6.7420 (5.5); 6.7349 (5.2); 6.7199 (5.2); 6.7130 (4.8); 6.3021 (3.1); 6.2872 (6.4); 6.2722 (3.1); 3.3142 (39.3); 3.1703 (3.5); 3.1542 (11.0); 3.1385 (12.0); 3.1228 (4.6); 2.9271 (5.4); 2.9112 (9.4); 2.8952 (4.2); 2.6771 (0.5); 2.6724 (0.7); 2.6678 (0.5); 2.5259 (2.0); 2.5212 (2.9); 2.5125 (38.1); 2.5079 (82.9); 2.5033 (115.9); 2.4987 (81.9); 2.4941 (37.1); 2.3301 (0.7); 2.3254 (0.5); 1.9895 (0.9); 0.0080 (1.8); -0.0002 (60.0); -0.0085 (1.7). (12.2); 6.7420 (5.5); 6.7349 (5.2); 6.7199 (5.2); 6.7130 (4.8); 6.3021 (3.1); 6.2872 (6.4); 6.2722 (3.1); 3.3142 (39.3); 3.1703 (3.5); 3.1542 (11.0); 3.1385 (12.0); 3.1228 (4.6); 2.9271 (5.4); 2.9112 (9.4); 2.8952 (4.2); 2.6771 (0.5); 2.6724 (0.7); 2.6678 (0.5); 2.5259 (2.0); 2.5212 (2.9); 2.5125 (38.1); 2.5079 (82.9); 2.5033 (115.9); 2.4987 (81.9); 2.4941 (37.1); 2.3301 (0.7); 2.3254 (0.5); 1.9895 (0.9); 0.0080 (1.8); -0.0002 (60.0); -0.0085 (1.7).
Beispiel Nr. 1.23-61 : Example No. 1.23-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9712 (7.1); 7.9519 (10.9); 7.6088 (13.2); 7.5995 (16.0); 7.5965 (8.1); 7.5764 (0.6); 7.5370 (0.9); 7.5267 (4.2); 7.5158 (6.0); 7.5069 (4.5); 7.4972 (3.7); 7.4951 (3.2); 7.4853 (2.6); 7.3168 (6.7); 7.2950 (7.2); 6.8614 (8.0); 6.8544 (8.6); 6.7040 (4.0); 6.6969 (3.8); 6.6819 (3.7); 6.6751 (3.5); 6.2725 (2.3); 6.2577 (4.6); 6.2431 (2.3); 4.0898 (0.6); 4.0761 (0.7); 3.3166 (38.9); 3.1795 (3.9); 3.1663 (4.0); 3.1562 (2.2); 3.1397 (6.9); 3.1234 (7.3); 3.1072 (3.4); 2.9880 (3.7); 2.9733 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9712 (7.1); 7.9519 (10.9); 7.6088 (13.2); 7.5995 (16.0); 7.5965 (8.1); 7.5764 (0.6); 7.5370 (0.9); 7.5267 (4.2); 7.5158 (6.0); 7.5069 (4.5); 7.4972 (3.7); 7.4951 (3.2); 7.4853 (2.6); 7.3168 (6.7); 7.2950 (7.2); 6.8614 (8.0); 6.8544 (8.6); 6.7040 (4.0); 6.6969 (3.8); 6.6819 (3.7); 6.6751 (3.5); 6.2725 (2.3); 6.2577 (4.6); 6.2431 (2.3); 4.0898 (0.6); 4.0761 (0.7); 3.3166 (38.9); 3.1795 (3.9); 3.1663 (4.0); 3.1562 (2.2); 3.1397 (6.9); 3.1234 (7.3); 3.1072 (3.4); 2.9880 (3.7); 2.9733
(5.7) ; 2.5129 (27.9); 2.5084 (59.6); 2.5038 (82.3); 2.4993 (58.6); 2.4948 (27.0); 2.0750 (3.6); 0.0079(5.7); 2.5129 (27.9); 2.5084 (59.6); 2.5038 (82.3); 2.4993 (58.6); 2.4948 (27.0); 2.0750 (3.6); 0.0079
(1.3) ; -0.0002 (36.3); -0.0085 (1.2). (1.3); -0.0002 (36.3); -0.0085 (1.2).
Beispiel Nr. 1.23-62: Example No. 1.23-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 8.0070 (7.1); 7.8124 (5.0); 7.8081 (5.5); 7.7932 (9.7); 7.7890 (10.6); 7.7744 (5.3); 7.7700 (5.8); 7.7024 (2.6); 7.6980 (2.6); 7.6897 (2.8); 7.6841 (4.8); 7.6638 (5.1); 7.6586 (3.3); 7.6503 (3.4); 7.6459 (3.1); 7.4133 (6.9); 7.3924 (6.6); 7.3870 (8.2); 7.3794 (9.3); 7.3769 (7.1); 7.3660 (6.8); 7.3604 (14.0); 7.3579 (11.8); 7.3413 (6.8); 7.3388 (6.2); 7.3252 (12.3); 7.3033 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.0070 (7.1); 7.8124 (5.0); 7.8081 (5.5); 7.7932 (9.7); 7.7890 (10.6); 7.7744 (5.3); 7.7700 (5.8); 7.7024 (2.6); 7.6980 (2.6); 7.6897 (2.8); 7.6841 (4.8); 7.6638 (5.1); 7.6586 (3.3); 7.6503 (3.4); 7.6459 (3.1); 7.4133 (6.9); 7.3924 (6.6); 7.3870 (8.2); 7.3794 (9.3); 7.3769 (7.1); 7.3660 (6.8); 7.3604 (14.0); 7.3579 (11.8); 7.3413 (6.8); 7.3388 (6.2); 7.3252 (12.3); 7.3033
(13.3) ; 6.8868 (14.7); 6.8797 (16.0); 6.7332 (7.4); 6.7264 (6.9); 6.7113 (6.8); 6.7043 (6.4); 6.3044 (4.1); 6.2893 (8.4); 6.2744 (4.1); 4.0914 (0.8); 4.0783 (0.8); 3.3195 (47.0); 3.1810 (5.6); 3.1763 (4.4); 3.1679(13.3); 6.8868 (14.7); 6.8797 (16.0); 6.7332 (7.4); 6.7264 (6.9); 6.7113 (6.8); 6.7043 (6.4); 6.3044 (4.1); 6.2893 (8.4); 6.2744 (4.1); 4.0914 (0.8); 4,0783 (0.8); 3.3195 (47.0); 3.1810 (5.6); 3.1763 (4.4); 3.1679
(6.4) ; 3.1604 (12.8); 3.1441 (13.8); 3.1282 (6.4); 3.0016 (8.4); 2.6741 (0.5); 2.5277 (1.5); 2.5141 (35.0); 2.5096 (77.2); 2.5050 (108.6); 2.5005 (77.9); 2.4959 (36.1); 2.3310 (0.5); 0.0080 (1.5); -0.0002 (50.9); - 0.0084 (1.7) (6.4); 3.1604 (12.8); 3.1441 (13.8); 3.1282 (6.4); 3.0016 (8.4); 2.6741 (0.5); 2.5277 (1.5); 2.5141 (35.0); 2.5096 (77.2); 2.5050 (108.6); 2,5005 (77.9); 2.4959 (36.1); 2.3310 (0.5); 0.0080 (1.5); -0.0002 (50.9); - 0.0084 (1.7)
Beispiel Nr. 1.23-64: Example No. 1.23-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8832 (8.4); 7.6433 (7.8); 7.6367 (12.9); 7.6339 (14.2); 7.6298 (16.0); 7.6201 (7.7); 7.6008 (1.6); 7.5772 (5.6); 7.5620 (5.8); 7.5580 (5.3); 7.5543 (4.6); 7.5077 (2.8); 7.5012 (2.8); 7.4963 (3.5); 7.4917 (2.6); 7.4855 (4.9); 7.4788 (6.0); 7.4705 (3.2); 7.4633 (3.2); 7.4560 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8832 (8.4); 7.6433 (7.8); 7.6367 (12.9); 7.6339 (14.2); 7.6298 (16.0); 7.6201 (7.7); 7.6008 (1.6); 7.5772 (5.6); 7.5620 (5.8); 7.5580 (5.3); 7.5543 (4.6); 7.5077 (2.8); 7.5012 (2.8); 7.4963 (3.5); 7.4917 (2.6); 7.4855 (4.9); 74788 (6.0); 7.4705 (3.2); 7.4633 (3.2); 7.4560
(1.8) ; 7.3241 (9.5); 7.3022 (10.4); 6.8972 (11.5); 6.8903 (12.3); 6.7442 (5.8); 6.7373 (5.2); 6.7224 (5.6); 6.7154 (5.2); 6.3049 (3.1); 6.2894 (6.4); 6.2745 (3.3); 3.3133 (27.3); 3.1714 (3.7); 3.1552 (11.4); 3.1395 (12.6); 3.1236 (4.9); 2.9276 (7.1); 2.9112 (12.9); 2.8951 (5.8); 2.6723 (0.8); 2.5257 (2.3); 2.5123 (51.4); 2.5078 (107.2); 2.5032 (144.4); 2.4987 (102.7); 2.4942 (48.5); 2.4380 (1.0); 2.3346 (0.8); 1.9894 (1.2); 1.1761 (0.7); 0.8579 (0.5); -0.0002 (25.3). Beispiel Nr. 1.23-73: (1.8); 7.3241 (9.5); 7.3022 (10.4); 6.8972 (11.5); 6.8903 (12.3); 6.7442 (5.8); 6.7373 (5.2); 6.7224 (5.6); 6.7154 (5.2); 6.3049 (3.1); 6.2894 (6.4); 6.2745 (3.3); 3.3133 (27.3); 3.1714 (3.7); 3.1552 (11.4); 3.1395 (12.6); 3.1236 (4.9); 2.9276 (7.1); 2.9112 (12.9); 2.8951 (5.8); 2.6723 (0.8); 2.5257 (2.3); 2.5123 (51.4); 2.5078 (107.2); 2.5032 (144.4); 2.4987 (102.7); 2.4942 (48.5); 2.4380 (1.0); 2.3346 (0.8); 1.9894 (1.2); 1.1761 (0.7); 0.8579 (0.5); -0.0002 (25.3). Example No. 1.23-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7416 (1.0); 7.5065 (1.0); 7.4867 (2.1); 7.4666 (1.6); 7.3738 (1.0); 7.3714 (1.3); 7.3676 (1.1); 7.3546 (0.8); 7.3506 (1.0); 7.3483 (0.8); 7.3233 (1.4); 7.3014 (1.6); 7.2946 (1.4); 7.2886 (1.8); 7.2842 (1.4); 7.1945 (1.0); 7.1924 (1.0); 7.1880 (0.9); 7.1860 (0.8); 7.1738 (0.9); 7.1717 (0.8); 7.1673 (0.8); 6.9021 (1.7); 6.8950 (1.8); 6.7388 (0.9); 6.7320 (0.8); 6.7170 (0.8); 6.7099 (0.8); 6.2786 (1.0); 3.8035 (16.0); 3.3213 (9.4); 3.1811 (1.1); 3.1680 (1.1); 3.1608 (0.6); 3.1445 (1.6); 3.1286 (1.7); 3.1128 (0.7); 2.8986 (0.6); 2.8830 (1.4); 2.8680 (1.3); 2.5138 (4.2); 2.5093 (9.0); 2.5048 (12.4); 2.5002 (8.8); 2.4957 (4.1); -0.0002 (2.2). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7416 (1.0); 7.5065 (1.0); 7.4867 (2.1); 7.4666 (1.6); 7.3738 (1.0); 7.3714 (1.3); 7.3676 (1.1); 7.3546 (0.8); 7.3506 (1.0); 7.3483 (0.8); 7.3233 (1.4); 7.3014 (1.6); 7.2946 (1.4); 7.2886 (1.8); 7.2842 (1.4); 7.1945 (1.0); 7.1924 (1.0); 7.1880 (0.9); 7.1860 (0.8); 7.1738 (0.9); 7.1717 (0.8); 7.1673 (0.8); 6.9021 (1.7); 6.8950 (1.8); 6.7388 (0.9); 6.7320 (0.8); 6.7170 (0.8); 6.7099 (0.8); 6.2786 (1.0); 3.8035 (16.0); 3.3213 (9.4); 3.1811 (1.1); 3.1680 (1.1); 3.1608 (0.6); 3.1445 (1.6); 3.1286 (1.7); 3.1128 (0.7); 2.8986 (0.6); 2.8830 (1.4); 2.8680 (1.3); 2.5138 (4.2); 2.5093 (9.0); 2.5048 (12.4); 2.5002 (8.8); 2.4957 (4.1); -0.0002 (2.2).
Beispiel Nr. 1.33-50: Example No. 1.33-50:
1H-NMR(400.0 MHz, CDC13): δ= 7.7530 (0.8); 7.7481 (5.2); 7.7438 (1.8); 7.7317 (1.9); 7.7274 (5.7); 7.7224 (0.9); 7.3116 (3.8); 7.3100 (4.4); 7.3050 (1.4); 7.2951 (1.4); 7.2902 (4.0); 7.2886 (3.5); 7.2614 (60.9); 7.2532 (0.6); 7.2516 (0.5); 7.2508 (0.5); 6.9999 (0.9); 6.9977 (0.9); 6.9750 (2.0); 6.9502 (1.1); 6.6610 (2.2); 6.6535 (2.3); 6.6470 (2.3); 6.6394 (2.1); 4.8007 (0.6); 4.7860 (1.1); 4.7710 (0.6); 3.2523 (1.0); 3.2484 (1.1); 3.2373 (2.8); 3.2319 (2.3); 3.2223 (3.6); 3.2028 (2.1); 3.2005 (2.0); 3.1929 (1.5); 3.1878 (3.1); 3.1770 (1.9); 3.1719 (2.1); 3.1607 (0.8); 3.1572 (0.7); 2.4254 (16.0); 0.0080 (0.6); -0.0002 (23.1); -0.0085 (0.8). 1 H NMR (400.0 MHz, CDCl 3 ): δ = 7.7530 (0.8); 7.7481 (5.2); 7.7438 (1.8); 7.7317 (1.9); 7.7274 (5.7); 7.7224 (0.9); 7.3116 (3.8); 7.3100 (4.4); 7.3050 (1.4); 7.2951 (1.4); 7.2902 (4.0); 7.2886 (3.5); 7.2614 (60.9); 7.2532 (0.6); 7.2516 (0.5); 7.2508 (0.5); 6.9999 (0.9); 6.9977 (0.9); 6.9750 (2.0); 6.9502 (1.1); 6.6610 (2.2); 6.6535 (2.3); 6.6470 (2.3); 6.6394 (2.1); 4.8007 (0.6); 4.7860 (1.1); 4.7710 (0.6); 3.2523 (1.0); 3.2484 (1.1); 3.2373 (2.8); 3.2319 (2.3); 3.2223 (3.6); 3.2028 (2.1); 3.2005 (2.0); 3.1929 (1.5); 3.1878 (3.1); 3.1770 (1.9); 3.1719 (2.1); 3.1607 (0.8); 3.1572 (0.7); 2.4254 (16.0); 0.0080 (0.6); -0.0002 (23.1); -0.0085 (0.8).
Beispiel Nr. 1.33-61 : Example No. 1.33-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9739 (7.0); 7.9539 (8.3); 7.9422 (8.5); 7.6114 (15.3); 7.6021 (16.0); 7.5784 (1.2); 7.5369 (0.8); 7.5270 (3.4); 7.5155 (4.5); 7.5055 (4.6); 7.4984 (3.2); 7.4949 (3.4); 7.4856 (2.4); 7.1870 (2.4); 7.1611 (4.6); 7.1387 (3.2); 6.7302 (3.8); 6.7125 (9.0); 6.7002 (9.2); 5.9781 (2.5); 5.9631 (5.3); 5.9485 (2.9); 3.3180 (23.3); 3.1792 (0.9); 3.1666 (1.0); 3.1302 (2.4); 3.1131 (7.4); 3.0969 (8.8); 3.0810 (4.2); 2.9877 (7.0); 2.9712 (10.4); 2.9547 (4.6); 2.5042 (71.4); 2.5001 (59.5); - 0.0002 (26.9). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9739 (7.0); 7.9539 (8.3); 7.9422 (8.5); 7.6114 (15.3); 7.6021 (16.0); 7.5.784 (1.2); 7.5369 (0.8); 7.5270 (3.4); 7.5155 (4.5); 7.5055 (4.6); 7.4984 (3.2); 7.4949 (3.4); 7.4856 (2.4); 7.1870 (2.4); 7.1611 (4.6); 7.1387 (3.2); 6.7302 (3.8); 6.7125 (9.0); 6.7002 (9.2); 5.9781 (2.5); 5.9631 (5.3); 5.9485 (2.9); 3.3180 (23.3); 3.1792 (0.9); 3.1666 (1.0); 3.1302 (2.4); 3.1131 (7.4); 3.0969 (8.8); 3.0810 (4.2); 2.9877 (7.0); 2.9712 (10.4); 2.9547 (4.6); 2.5042 (71.4); 2,5001 (59.5); - 0.0002 (26.9).
Beispiel Nr. 1.33-62: Example No. 1.33-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 8.0103 (3.7); 7.9969 (8.5); 7.9831 (3.8); 7.8132 (5.6); 7.8088 (6.2); 7.7940 (10.8); 7.7897 (11.6); 7.7751 (6.2); 7.7707 (6.5); 7.7029 (2.9); 7.6984 (3.0); 7.6901 (3.3); 7.6845 (5.3); 7.6714 (4.6); 7.6670 (5.0); 7.6640 (5.6); 7.6590 (3.8); 7.6507 (3.8); 7.6462 (3.4); 7.4170 (6.8); 7.4148 (7.6); 7.3961 (6.6); 7.3938 (7.3); 7.3882 (8.8); 7.3792 (10.3); 7.3765 (8.1); 7.3673 (7.3); 7.3601 (15.5); 7.3575 (13.0); 7.3411 (7.6); 7.3384 (6.9); 7.1941 (4.2); 7.1687 (7.4); 7.1462 (5.8); 6.7657 (2.8); 6.7576 (6.4); 6.7480 (5.4); 6.7386 (16.0); 6.7265 (15.7); 6.0080 (4.4); 5.9927 (9.0); 5.9778 (4.4); 3.3183 (66.4); 3.1495 (4.2); 3.1333 (13.3); 3.1170 (14.6); 3.1008 (7.2); 3.0171 (5.6); 3.0017 (11.4); 2.9863 (10.2); 2.9710 (3.6); 2.6738 (0.8); 2.5272 (2.0); 2.5224 (2.9); 2.5137 (45.0); 2.5092 (98.7); 2.5046 (139.2); 2.5000 (99.2); 2.4955 (45.4); 2.3314 (0.8); 0.0081 (2.0); -0.0002 (68.2); -0.0084 (2.1) Beispiel Nr. 1.33-64: 1 H-NMR (400.0 MHz, de-DMSO): δ = 8.0103 (3.7); 7.9969 (8.5); 7.9831 (3.8); 7.8132 (5.6); 7.8088 (6.2); 7.7940 (10.8); 7.7897 (11.6); 7.7751 (6.2); 7.7707 (6.5); 7.7029 (2.9); 7.6984 (3.0); 7.6901 (3.3); 7.6845 (5.3); 7.6714 (4.6); 7.6670 (5.0); 7.6640 (5.6); 7.6590 (3.8); 7.6507 (3.8); 7.6462 (3.4); 7.4170 (6.8); 7.4148 (7.6); 7.3961 (6.6); 7.3938 (7.3); 7.3882 (8.8); 7.3792 (10.3); 7.3765 (8.1); 7.3673 (7.3); 7.3601 (15.5); 7.3575 (13.0); 7.3411 (7.6); 7.3384 (6.9); 7.1941 (4.2); 7.1687 (7.4); 7.1462 (5.8); 6.7657 (2.8); 6.7576 (6.4); 6.7480 (5.4); 6.7386 (16.0); 6.7265 (15.7); 6.0080 (4.4); 5.9927 (9.0); 5.9778 (4.4); 3.3183 (66.4); 3.1495 (4.2); 3.1333 (13.3); 3.1170 (14.6); 3.1008 (7.2); 3.0171 (5.6); 3.0017 (11.4); 2.9863 (10.2); 2.9710 (3.6); 2.6738 (0.8); 2.5272 (2.0); 2.5224 (2.9); 2.5137 (45.0); 2.5092 (98.7); 2.5046 (139.2); 2.5000 (99.2); 2.4955 (45.4); 2.3314 (0.8); 0.0081 (2.0); -0.0002 (68.2); -0.0084 (2.1) Example No. 1.33-64:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8899 (3.6); 7.8753 (7.6); 7.8610 (3.6); 7.6450 (9.1); 7.6353 (14.6); 7.6319 (16.0); 7.6209 (7.6); 7.6015 (1.8); 7.5788 (5.5); 7.5633 (5.3); 7.5593 (5.6); 7.5097 (2.8); 7.5026 (2.6); 7.4984 (4.0); 7.4870 (4.8); 7.4807 (5.6); 7.4716 (2.8); 7.4649 (3.5); 7.4577 (1.7); 7.1927 (3.3); 7.1675 (5.7); 7.1447 (4.5); 6.7694 (4.9); 6.7594 (4.4); 6.7505 (12.2); 6.7382 (11.8); 6.0051 (3.3); 5.9907 (6.8); 5.9751 (3.5); 3.3153 (29.9); 3.1459 (3.9); 3.1296 (11.8); 3.1138 (13.0); 3.0978 (5.3); 2.9340 (5.1); 2.9185 (12.5); 2.9030 (11.5); 2.8871 (3.9); 2.6732 (0.8); 2.5124 (50.4); 2.5081 (101.5); 2.5037 (135.4); 2.4993 (97.1); 2.4949 (46.7); 2.3314 (0.8); 1.9895 (0.9); 1.1759 (0.5); -0.0002 (22.1). 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8899 (3.6); 7.8753 (7.6); 7.8610 (3.6); 7.6450 (9.1); 7.6353 (14.6); 7.6319 (16.0); 7.6209 (7.6); 7.6015 (1.8); 7.5788 (5.5); 7.5633 (5.3); 7.5593 (5.6); 7.5097 (2.8); 7.5026 (2.6); 7.4984 (4.0); 7.4870 (4.8); 7.4807 (5.6); 7.4716 (2.8); 7.4649 (3.5); 7.4577 (1.7); 7.1927 (3.3); 7.1675 (5.7); 7.1447 (4.5); 6.7694 (4.9); 6.7594 (4.4); 6.7505 (12.2); 6.7382 (11.8); 6.0051 (3.3); 5.9907 (6.8); 5.9751 (3.5); 3.3153 (29.9); 3.1459 (3.9); 3.1296 (11.8); 3.1138 (13.0); 3.0978 (5.3); 2.9340 (5.1); 2.9185 (12.5); 2.9030 (11.5); 2,888 (3.9); 2.6732 (0.8); 2.5124 (50.4); 2.5081 (101.5); 2.5037 (135.4); 2.4993 (97.1); 2.4949 (46.7); 2.3314 (0.8); 1.9895 (0.9); 1.1759 (0.5); -0.0002 (22.1).
Beispiel Nr. 1.33-73: Example No. 1.33-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7464 (0.5); 7.7321 (1.1); 7.5067 (1.0); 7.4870 (2.1); 7.4668 (1.6); 7.3742 (1.0); 7.3719 (1.3); 7.3681 (1.1); 7.3550 (0.8); 7.3511 (1.0); 7.3488 (0.8); 7.2968 (1.4); 7.2908 (1.7); 7.2864 (1.4); 7.1939 (1.5); 7.1895 (1.1); 7.1752 (1.1); 7.1729 (1.1); 7.1687 (1.8); 7.1430 (0.5); 6.7656 (0.8); 6.7567 (1.3); 6.7502 (1.4); 6.7376 (1.7); 5.9797 (1.0); 3.8035 (16.0); 3.3184 (11.0); 3.1342 (0.6); 3.1180 (1.6); 3.1019 (1.8); 3.0859 (0.7); 2.8966 (0.7); 2.8811 (1.6); 2.8654 (1.5); 2.8495 (0.5); 2.5130 (5.2); 2.5085 (11.2); 2.5040 (15.5); 2.4994 (11.1); 2.4949 (5.2); -0.0002 (2.8) 1 H NMR (400.0 MHz, de-DMSO): δ = 7.7464 (0.5); 7.7321 (1.1); 7.5067 (1.0); 7.4870 (2.1); 7.4668 (1.6); 7.3742 (1.0); 7.3719 (1.3); 7.3681 (1.1); 7.3550 (0.8); 7.3511 (1.0); 7.3488 (0.8); 7.2968 (1.4); 7.2908 (1.7); 7.2864 (1.4); 7.1939 (1.5); 7.1895 (1.1); 7.1752 (1.1); 7.1729 (1.1); 7.1687 (1.8); 7.1430 (0.5); 6.7656 (0.8); 6.7567 (1.3); 6.7502 (1.4); 6.7376 (1.7); 5.9797 (1.0); 3.8035 (16.0); 3.3184 (11.0); 3.1342 (0.6); 3.1180 (1.6); 3.1019 (1.8); 3.0859 (0.7); 2.8966 (0.7); 2.8811 (1.6); 2.8654 (1.5); 2.8495 (0.5); 2.5130 (5.2); 2.5085 (11.2); 2.5040 (15.5); 2.4994 (11.1); 2.4949 (5.2); -0.0002 (2.8)
Beispiel Nr. 1.43-34: Example No. 1.43-34:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8663 (2.1); 7.8611 (0.8); 7.8532 (2.2); 7.8487 (1.2); 7.8441 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8663 (2.1); 7.8611 (0.8); 7.8532 (2.2); 7.8487 (1.2); 7.8441
(2.3) ; 7.8362 (1.0); 7.8311 (2.1); 7.7612 (1.0); 7.4233 (2.2); 7.4180 (0.7); 7.4012 (4.1); 7.3961 (0.8); 7.3841 (0.7); 7.3790 (2.0); 7.0269 (1.2); 7.0026 (1.4); 6.7334 (3.4); 6.7265 (1.9); 6.7178 (1.2); 5.5709(2.3); 7.8362 (1.0); 7.8311 (2.1); 7.7612 (1.0); 7.4233 (2.2); 7.4180 (0.7); 7.4012 (4.1); 7.3961 (0.8); 7.3841 (0.7); 7.3790 (2.0); 7.0269 (1.2); 7.0026 (1.4); 6.7334 (3.4); 6.7265 (1.9); 6.7178 (1.2); 5.5709
(0.6); 5.5554 (1.2); 5.5402 (0.6); 3.7428 (16.0); 3.3198 (9.9); 3.1017 (0.7); 3.0855 (1.9); 3.0692 (2.0); 3.0528 (0.8); 2.8807 (1.3); 2.8696 (1.2); 2.5130 (5.8); 2.5086 (11.8); 2.5041 (15.8); 2.4995 (11.1); 2.4951 (5.1); -0.0002 (2.8). Beispiel Nr. 1.43-35: (0.6); 5.5554 (1.2); 5.5402 (0.6); 3.7428 (16.0); 3.3198 (9.9); 3.1017 (0.7); 3.0855 (1.9); 3.0692 (2.0); 3.0528 (0.8); 2.8807 (1.3); 2.8696 (1.2); 2.5130 (5.8); 2.5086 (11.8); 2.5041 (15.8); 2.4995 (11.1); 2.4951 (5.1); -0.0002 (2.8). Example No. 1.43-35:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.8415 (0.7); 7.8274 (1.5); 7.8134 (0.8); 7.7993 (3.7); 7.7780 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.8415 (0.7); 7.8274 (1.5); 7.8134 (0.8); 7.7993 (3.7); 7.7780
(5.4) ; 7.6490 (5.0); 7.6322 (1.3); 7.6271 (4.2); 7.0220 (1.5); 7.0005 (1.7); 6.7299 (4.9); 6.7086 (1.3); 5.5686 (0.7); 5.5532 (1.5); 5.5378 (0.8); 3.7431 (16.0); 3.3151 (11.0); 3.1784 (0.6); 3.1652 (0.6); 3.0986 (0.7); 3.0816 (2.1); 3.0657 (2.4); 3.0496 (1.1); 2.9035 (0.9); 2.8875 (2.2); 2.8720 (2.0); 2.8558 (0.8); 2.5071 (18.5); 2.5026 (27.0); 2.4983 (21.6); -0.0002 (10.6) Beispiel Nr. 1.43-40: (5.4); 7.6490 (5.0); 7.6322 (1.3); 7.6271 (4.2); 7.0220 (1.5); 7,0005 (1.7); 6.7299 (4.9); 6.7086 (1.3); 5.5686 (0.7); 5.5532 (1.5); 5.5378 (0.8); 3.7431 (16.0); 3.3151 (11.0); 3.1784 (0.6); 3.1652 (0.6); 3.0986 (0.7); 3.0816 (2.1); 3.0657 (2.4); 3.0496 (1.1); 2.9035 (0.9); 2.8875 (2.2); 2.8720 (2.0); 2.8558 (0.8); 2.5071 (18.5); 2.5026 (27.0); 2.4983 (21.6); -0.0002 (10.6) Example No. 1.43-40:
'H-NMR^OO.O MHZ, de-DMSO): δ= 7.7316 (0.5); 7.7245 (4.1); 7.7199 (1.3); 7.7072 (1.5); 7.7027 (4.2); 7.6947 (0.5); 7.5566 (0.7); 7.5418 (1.5); 7.5272 (0.7); 7.0981 (0.6); 7.0910 (4.3); 7.0864 (1.4); 7.0737 (1.4); 7.0690 (3.9); 7.0217 (1.3); 7.0006 (1.5); 6.7299 (4.5); 6.7090 (1.1); 6.7021 (0.7); 5.5590 (0.6); 5.5437 (1.4); 5.5285 (0.7); 3.8191 (16.0); 3.7391 (15.0); 3.3090 (19.6); 3.0824 (0.7); 3.0663 (1.9); 3.0499 (2.0); 3.0332 (0.9); 2.8469 (0.9); 2.8311 (1.9); 2.8145 (1.8); 2.7986 (0.7); 2.5234 (1.0); 2.5099 (16.9); 2.5056 (33.5); 2.5011 (44.2); 2.4968 (32.0); 2.4928 (16.2); 0.0009 (8.5); -0.0002 (10.8); -0.0072 (0.5); -0.0085 (0.5). Beispiel Nr. 1.43-50:  'H-NMR ^ OO.O MHZ, de-DMSO): δ = 7.7316 (0.5); 7.7245 (4.1); 7.7199 (1.3); 7.7072 (1.5); 7.7027 (4.2); 7.6947 (0.5); 7.5566 (0.7); 7.5418 (1.5); 7.5272 (0.7); 7.0981 (0.6); 7.0910 (4.3); 7.0864 (1.4); 7.0737 (1.4); 7.0690 (3.9); 7.0217 (1.3); 7,0006 (1.5); 6.7299 (4.5); 6.7090 (1.1); 6.7021 (0.7); 5.5590 (0.6); 5.5437 (1.4); 5.5285 (0.7); 3.8191 (16.0); 3.7391 (15.0); 3.3090 (19.6); 3.0824 (0.7); 3.0663 (1.9); 3.0499 (2.0); 3.0332 (0.9); 2.8469 (0.9); 2.8311 (1.9); 2.8145 (1.8); 2.7986 (0.7); 2.5234 (1.0); 2.5099 (16.9); 2.5056 (33.5); 2.5011 (44.2); 2.4968 (32.0); 2.4928 (16.2); 0.0009 (8.5); -0.0002 (10.8); -0.0072 (0.5); -0.0085 (0.5). Example No. 1.43-50:
1H-NMR(400.0 MHz, CDC13): δ= 7.7470 (2.7); 7.7427 (1.0); 7.7307 (1.0); 7.7263 (3.1); 7.7214 (0.6); 7.3075 (2.0); 7.3059 (2.3); 7.3009 (0.8); 7.2908 (0.7); 7.2861 (2.2); 7.2845 (1.9); 7.2613 (25.0); 7.2572 1 H-NMR (400.0 MHz, CDCl 3 ): δ = 7.7470 (2.7); 7.7427 (1.0); 7.7307 (1.0); 7.7263 (3.1); 7.7214 (0.6); 7.3075 (2.0); 7.3059 (2.3); 7.3009 (0.8); 7.2908 (0.7); 7.2861 (2.2); 7.2845 (1.9); 7.2613 (25.0); 7.2572
(1.0) ; 7.2564 (0.8); 7.2556 (0.7); 7.2548 (0.6); 7.2540 (0.5); 6.8644 (1.1); 6.8424 (1.5); 6.7256 (1.1); 6.7184 (1.8); 6.7046 (1.0); 6.6973 (0.6); 6.6827 (0.7); 6.6755 (0.6); 4.7918 (0.6); 3.8259 (3.6); 3.8198 (16.0); 3.2313 (0.6); 3.2204 (1.5); 3.2148 (1.4); 3.2053 (2.0); 3.1883 (1.1); 3.1861 (1.1); 3.1789 (0.9); 3.1735 (1.7); 3.1632 (1.1); 3.1576 (1.2); 2.4223 (8.5); -0.0002 (9.8) (1.0); 7.2564 (0.8); 7.2556 (0.7); 7.2548 (0.6); 7.2540 (0.5); 6.8644 (1.1); 6.8424 (1.5); 6.7256 (1.1); 6.7184 (1.8); 6.7046 (1.0); 6.6973 (0.6); 6.6827 (0.7); 6.6755 (0.6); 4.7918 (0.6); 3.8259 (3.6); 3.8198 (16.0); 3.2313 (0.6); 3.2204 (1.5); 3.2148 (1.4); 3.2053 (2.0); 3.1883 (1.1); 3.1861 (1.1); 3.1789 (0.9); 3.1735 (1.7); 3.1632 (1.1); 3.1576 (1.2); 2.4223 (8.5); -0.0002 (9.8)
Beispiel Nr. 1.43-61 : Example No. 1.43-61:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9781 (1.9); 7.9757 (1.1); 7.9595 (1.6); 7.9573 (1.7); 7.9394 (1.2); 7.9259 (0.6); 7.6220 (3.2); 7.6196 (3.4); 7.6129 (2.5); 7.6092 (2.1); 7.6057 (1.7); 7.5302 (1.0); 7.5214 (0.9); 7.5172 (0.8); 7.5105 (1.1); 7.5028 (0.9); 7.4966 (0.7); 7.4889 (0.7); 7.0171 (1.1); 6.9962 (1.2); 6.7034 (4.0); 6.6830 (1.0); 6.6760 (0.6); 5.5585 (0.5); 5.5435 (1.2); 5.5284 (0.6); 3.7414 (16.0); 3.3158 (9.9); 3.0764 (1.4); 3.0601 (1.6); 3.0438 (0.8); 2.9862 (0.8); 2.9696 (1.5); 2.9541 (1.4); 2.5120 (6.4); 2.5075 (14.0); 2.5029 (19.5); 2.4983 (13.9); 2.4938 (6.4); -0.0002 (9.1) 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9781 (1.9); 7.9757 (1.1); 7.9595 (1.6); 7.9573 (1.7); 7.9394 (1.2); 7.9259 (0.6); 7.6220 (3.2); 7.6196 (3.4); 7.6129 (2.5); 7.6092 (2.1); 7.6057 (1.7); 7.5302 (1.0); 7.5214 (0.9); 7.5172 (0.8); 7.5105 (1.1); 7.5028 (0.9); 7.4966 (0.7); 7.4889 (0.7); 7.0171 (1.1); 6.9962 (1.2); 6.7034 (4.0); 6.6830 (1.0); 6.6760 (0.6); 5.5585 (0.5); 5.5435 (1.2); 5.5284 (0.6); 3.7414 (16.0); 3.3158 (9.9); 3.0764 (1.4); 3.0601 (1.6); 3.0438 (0.8); 2.9862 (0.8); 2.9696 (1.5); 2.9541 (1.4); 2.5120 (6.4); 2.5075 (14.0); 2.5029 (19.5); 2.4983 (13.9); 2.4938 (6.4); -0.0002 (9.1)
Beispiel Nr. 1.43-62: Example No. 1.43-62:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.9851 (1.1); 7.8149 (0.7); 7.8107 (0.7); 7.7957 (1.4); 7.7918 (1.4); 7.7766 (1.0); 7.7729 (0.9); 7.6889 (0.8); 7.6749 (0.7); 7.6686 (0.8); 7.4225 (1.1); 7.4008 (1.0); 7.3953 (1.2); 7.3813 (1.3); 7.3747 (1.0); 7.3623 (2.0); 7.3432 (1.0); 7.0257 (1.2); 7.0017 (1.4); 6.7260 (4.6); 6.7078 (1.3); 6.7013 (0.8); 5.5849 (0.7); 5.5700 (1.4); 5.5548 (0.7); 3.7424 (16.0); 3.7277 (0.7); 3.3139 (8.3); 3.1652 (1.6); 3.1098 (0.5); 3.0937 (1.7); 3.0772 (2.1); 3.0611 (1.1); 2.9840 (1.5); 2.5111 (8.8); 2.5070 (17.0); 2.5026 (22.3); 2.4983 (16.2); 2.4942 (8.1); 1.9891 (1.5); 1.1755 (0.8); 0.8583 (0.6); -0.0002 (6.5). Beispiel Nr. 1.43-73: 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.9851 (1.1); 7.8149 (0.7); 7.8107 (0.7); 7.7957 (1.4); 7.7918 (1.4); 7.7766 (1.0); 7.7729 (0.9); 7.6889 (0.8); 7.6749 (0.7); 7.6686 (0.8); 7.4225 (1.1); 7,4008 (1.0); 7.3953 (1.2); 7.3813 (1.3); 7.3747 (1.0); 7.3623 (2.0); 7.3432 (1.0); 7.0257 (1.2); 7.0017 (1.4); 6.7260 (4.6); 6.7078 (1.3); 6.7013 (0.8); 5.5849 (0.7); 5.5700 (1.4); 5.5548 (0.7); 3.7424 (16.0); 3.7277 (0.7); 3.3139 (8.3); 3.1652 (1.6); 3.1098 (0.5); 3.0937 (1.7); 3.0772 (2.1); 3.0611 (1.1); 2.9840 (1.5); 2.5111 (8.8); 2.5070 (17.0); 2.5026 (22.3); 2.4983 (16.2); 2.4942 (8.1); 1.9891 (1.5); 1.1755 (0.8); 0.8583 (0.6); -0.0002 (6.5). Example No. 1.43-73:
1H-NMR(400.0 MHz, de-DMSO): δ= 7.7346 (0.6); 7.7200 (1.3); 7.7052 (0.6); 7.5094 (1.1); 7.4897 1 H-NMR (400.0 MHz, de-DMSO): δ = 7.7346 (0.6); 7.7200 (1.3); 7.7052 (0.6); 7.5094 (1.1); 7.4897
(2.1) ; 7.4694 (1.6); 7.3704 (1.4); 7.3502 (1.0); 7.2973 (1.4); 7.2913 (1.9); 7.2870 (1.4); 7.1995 (1.0); 7.1932 (1.0); 7.1789 (0.9); 7.1725 (0.9); 7.0222 (1.1); 7.0018 (1.3); 6.7344 (3.8); 6.7130 (1.0); 5.5666 (0.5); 5.5518 (1.1); 5.5362 (0.6); 3.8027 (16.0); 3.7393 (14.4); 3.3121 (36.3); 3.0926 (0.6); 3.0761 (1.6); 3.0598 (1.7); 3.0434 (0.7); 2.8867 (0.8); 2.8710 (1.7); 2.8543 (1.6); 2.8389 (0.5); 2.5239 (1.0); 2.5102 (16.0); 2.5057 (33.2); 2.5012 (44.6); 2.4967 (31.4); 2.4922 (14.4); -0.0002 (6.1). (2.1); 7.4694 (1.6); 7.3704 (1.4); 7.3502 (1.0); 7.2973 (1.4); 7.2913 (1.9); 7.2870 (1.4); 7.1995 (1.0); 7.1932 (1.0); 7.1789 (0.9); 7.1725 (0.9); 7.0222 (1.1); 7.0018 (1.3); 6.7344 (3.8); 6.7130 (1.0); 5.5666 (0.5); 5.5518 (1.1); 5.5362 (0.6); 3.8027 (16.0); 3.7393 (14.4); 3.3121 (36.3); 3.0926 (0.6); 3.0761 (1.6); 3.0598 (1.7); 3.0434 (0.7); 2.8867 (0.8); 2.8710 (1.7); 2.8543 (1.6); 2.8389 (0.5); 2.5239 (1.0); 2.5102 (16.0); 2.5057 (33.2); 2.5012 (44.6); 2.4967 (31.4); 2.4922 (14.4); -0.0002 (6.1).
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung mindestens eines N-Sulfonyl-N'- aryldiaminoalkans und N-Sulfonyl-N'- heteroaryldiaminoalkans der allgemeinen Formel (I), in Another object of the present invention is the use of at least one N-sulfonyl-N'-aryldiaminoalkans and N-sulfonyl-N'-heteroaryldiaminoalkans the general formula (I), in
Kombination mit weiteren agrochemischen Wirkstoffen wie beispielsweise Fungizide, Insektizide, Herbizide, Pflanzenwachstumsregulatoren oder Safener, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren, bevorzugt Trockenstress, sowie zur Stärkung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags. Combination with other agrochemical active substances such as, for example, fungicides, insecticides, herbicides, plant growth regulators or safeners, for increasing the resistance of plants to abiotic stress factors, preferably drought stress, and for strengthening plant growth and / or for increasing the plant yield.
Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Another object of the present invention is a spray solution for the treatment of plants, containing one for increasing the resistance of plants to abiotic
Stressfaktoren wirksame Menge von mindestens einer Verbindung, ausgewählt aus der Gruppe, bestehend aus mindestens einem der erfindungsgemäß substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'-heteroaryldiaminoalkane, der allgemeinen Formel (I). Zu den dabei relativierbaren abiotischen Streßbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress (Stress verursacht durch Trockenheit und/oder Wassermangel), osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Stress factors effective amount of at least one compound selected from the group consisting of at least one of the inventively substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane, the general formula (I). For example, heat, drought, cold and dry stress (stress caused by dryness and / or lack of water), osmotic stress, waterlogging, increased soil salt content, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, may be among the abiotic stress conditions that can be relativized. limited availability of
Phosphornährstoffen zählen. Counting phosphorus nutrients.
In einer Ausführungsform kann beispielsweise vorgesehen sein, dass eine oder mehrere der For example, in one embodiment, one or more of the
erfindungsgemäß zu verwendenden Verbindungen, d. h. die entsprechenden erfindungsgemäß substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'-heteroaryldiaminoalkane der allgemeinen Formel (I), durch eine Sprühapplikation auf entsprechend zu behandelnde Pflanzen oder Pflanzenteile aufgebracht werden. Die Verwendung der Verbindungen der allgemeinen Formel (I) oder deren Salze erfolgt vorzugsweise mit einer Dosierung zwischen 0,00005 und 3 kg/ha, besonders bevorzugt zwischen 0,0001 und 2 kg/ha, insbesondere bevorzugt zwischen 0,0005 und 1 kg/ha, im Speziellen bevorzugt zwischen 0,001 und 0,25 kg/ha. According to the invention to be used compounds, d. H. the corresponding inventively substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I) are applied by spray application to be treated according to plants or plant parts. The use of the compounds of the general formula (I) or salts thereof is preferably carried out with a dosage of between 0.00005 and 3 kg / ha, particularly preferably between 0.0001 and 2 kg / ha, particularly preferably between 0.0005 and 1 kg / ha, more preferably between 0.001 and 0.25 kg / ha.
Unter der Bezeichnung Resistenz bzw. Widerstandsfähigkeit gegenüber abiotischem Stress werden im Rahmen der vorliegenden Erfindung verschiedenartige Vorteile für Pflanzen verstanden. Solche vorteilhaften Eigenschaften äußern sich beispielsweise in den nachfolgend genannten verbesserten Pflanzencharakteristika: verbessertes Wurzelwachstum hinsichtlich Oberfläche und Tiefe, vermehrte Ausläuferbildung oder BeStockung, stärkere und produktivere Ausläufer und Bestockungstriebe, Verbesserang des Sproßwachstums, erhöhte Standfestigkeit, vergrößerte Sprossbasisdurchmesser, vergrößerte Blattfläche, höhere Erträge an Nähr- und Inhaltsstoffen, wie z.B. Kohlenhydrate, Fette, Öle, Proteine, Vitamine, Mineralstoffe, ätherische Öle, Farbstoffe, Fasern, bessere Faserqualität, früheres Blühen, gesteigerte Blütenanzahl, reduzierter Gehalt an toxischen Produkten wie Mycotoxine, reduzierter Gehalt an Rückständen oder unvorteilhaften Bestandteilen jeglicher Art oder bessere Verdaulichkeit, verbesserte Lagerstabilität des Erntegutes, verbesserter Toleranz gegenüber unvorteilhaften Temperaturen, verbesserter Toleranz gegenüber Dürre und Trockenheit, wie auch Sauerstoffmangel durch Wasserüberschuß, verbesserte Toleranz gegenüber erhöhten Salzgehalten in Böden und Wasser, gesteigerte Toleranz gegenüber Ozonstress, verbesserte Verträglichkeit gegenüber Herbiziden und anderen Pflanzenbehandlungsmitteln, verbesserte Wasseraufnahme und In the context of the present invention, the term resistance or resistance to abiotic stress is understood to mean various advantages for plants. Such advantageous properties are manifested, for example, in the following improved plant characteristics: improved root growth in terms of surface area and depth, increased runners or stocking, stronger and more productive shoots and tillers, Improvement of shoot growth, increased stability, increased shoot base diameter, increased leaf area, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers , reduced content of toxic products such as mycotoxins, reduced content of residues or unfavorable ingredients of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperatures, improved tolerance to drought and drought, as well as oxygen deficiency due to excess water, improved tolerance to increased Salt contents in soils and water, increased tolerance to ozone stress, improved tolerance to herbicides and other plant treatment products, improved water absorption and
Photosyntheseleistung, vorteilhafte Pflanzeneigenschaften, wie beispielsweise Beschleunigung der Reifung, gleichmäßigere Abreife, größere Anziehungskraft für Nützlinge, verbesserte Bestäubung oder andere Vorteile, die einem Fachmann durchaus bekannt sind. Insbesondere zeigt die Verwendung einer oder mehrerer erfindungsgemäßen Verbindungen der allgemeinen Formel (I) in der Sprühapplikation auf Pflanzen und Pflanzenteilen die beschriebenen Vorteile. Die kombinierte Verwendung von erfindungsgemäßen N-Sulfonyl-N'-aryldiaminoalkanen und N-Sulfonyl-N'-heteroaryldiaminoalkanen der allgemeinen Formel (I) mit gentechnisch veränderten Sorten in Bezug auf erhöhte abiotische Stresstoleranz ist darüber hinaus ebenfalls möglich.  Photosynthetic performance, beneficial plant properties, such as acceleration of maturation, more uniform maturity, greater attraction for beneficials, improved pollination or other benefits that are well known to a person skilled in the art. In particular, the use of one or more compounds of the general formula (I) according to the invention in the spray application to plants and plant parts has the advantages described. The combined use of N-sulfonyl-N'-aryldiaminoalkanen invention and N-sulfonyl-N'-heteroaryldiaminoalkanen the general formula (I) with genetically modified varieties in terms of increased abiotic stress tolerance is also possible.
Die weiter oben genannten verschiedenartigen Vorteile für Pflanzen lassen sich bekannterweise partiell zusammenfassen und mit allgemein gültigen Begriffen belegen. Soche Begriffe sind beispielsweise die nachfolgend aufgeführten Bezeichnungen: phytotonischer Effekt, Widerstandsfähigkeit gegenüber Stressfaktoren, weniger Pflanzenstress, Pflanzengesundheit, gesunde Pflanzen, Pflanzenfitness, („Plant Fitness"),„Plant Wellness",„Plant Concept",„Vigor Effect",„Stress Shield", Schutzschild,„CropThe various advantages for plants mentioned above can, as is known, be partially summarized and substantiated by generally valid terms. Soche terms are, for example, the following: phytotonic effect, resistance to stress factors, less plant stress, plant health, healthy plants, plant fitness, plant wellness, plant concept, vigor effect, stress Shield, "Shield," Crop
Health",„Crop Health Properties",„Crop Health Products",„Crop Health Management",„Crop Health Therapy",„Plant Health", Plant Health Properties", Plant Health Products",„Plant Health Health, Crop Health Properties, Crop Health Products, Crop Health Management, Plant Health, Plant Health Properties, Plant Health Products, Plant Health
Management",„Plant Health Therapy", Grünungseffekt („Greening Effect" oder„Re-greening Effect"), „Freshness" oder andere Begriffe, die einem Fachmann durchaus bekannt sind. Management, Plant Health Therapy, Greening Effect, Freshness or other terms well known to those skilled in the art.
Im Rahmen der vorliegenden Erfindung wird unter einem guten Effekt auf die Widerstandsfähigkeit gegenüber abiotischem Stress nicht beschränkend mindestens ein um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbessertes Auflaufen, In the context of the present invention, a good effect on the abiotic stress resistance is not limited to at least one emergence, which is improved by generally 3%, in particular greater than 5%, particularly preferably greater than 10%.
mindestens einen im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % gesteigerten Ertrag, mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Wurzelentwicklung, at least one generally 3%, in particular greater than 5%, particularly preferably greater than 10% increased yield, at least one root development generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % ansteigende Sproßgröße,  at least one shoot size increasing by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
· mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % vergrößerte Blattfläche, At least one leaf area increased by generally 3%, in particular greater than 5%, particularly preferably greater than 10%,
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Photosyntheseleistung und/oder  at least one in general 3%, in particular greater than 5%, particularly preferably greater than 10%, improved photosynthesis performance and / or
mindestens eine um im Allgemeinen 3 %, insbesondere größer als 5 % besonders bevorzugt größer als 10 % verbesserte Blütenausbildung verstanden, wobei die Effekte einzeln oder aber in beliebiger Kombination von zwei oder mehreren Effekten auftreten können. Weiterer Gegenstand der vorliegenden Erfindung ist eine Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen  at least one flower formation generally improved by 3%, in particular greater than 5%, particularly preferably greater than 10%, the effects being able to occur individually or else in any combination of two or more effects. Another object of the present invention is a spray solution for the treatment of plants, containing one for increasing the resistance of plants to abiotic
Stressfaktoren wirksame Menge von mindestens einer Verbindung aus der Gruppe der erfindungsgemäß substituierten N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I). Die Sprühlösung kann andere übliche Bestandteile aufweisen, wie Stress factors effective amount of at least one compound from the group of substituted according to the invention N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I). The spray solution may have other common ingredients, such as
Lösungsmittel, Formulierhilfsstoffe, insbesondere Wasser, enthalten. Weitere Bestandteile können unter anderem agrochemische Wirkstoffe sein, welche unten noch weiter beschrieben werden. Solvents, formulation auxiliaries, especially water. Other ingredients may include agrochemical agents, which are further described below.
Weiterer Gegenstand der vorliegenden Erfindung ist die Verwendung von entsprechenden Another object of the present invention is the use of corresponding
Sprühlösungen zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Spraying solutions to increase the resistance of plants to abiotic
Stressfaktoren. Die nachfolgenden Ausführungen gelten sowohl für die Verwendung einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) an sich als auch für die entsprechenden Sprühlösungen. Stress factors. The following statements apply both to the use of one or more compounds of the general formula (I) according to the invention per se and to the corresponding spray solutions.
Eswurde darüber hinaus gefunden, dass die Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der allgemeinen Formel (I) in Kombination mit mindestens einem Düngemittel wie weiter unten stehend definiert auf Pflanzen oder in deren Umgebung möglich ist. It has also been found that the use of one or more compounds of the general formula (I) according to the invention in combination with at least one fertilizer as defined below is possible on plants or in their environment.
Düngemittel, die erfindungsgemäß zusammen mit den oben näher erläuterten erfindungsgemäßen Verbindungen der allgemeinen Formel (I) verwendet werden können, sind im Allgemeinen organische und anorganische Stickstoff-haltige Verbindungen wie beispielsweise Harnstoffe, Harnstoff- Formaldehyd-Kondensationsprodukte, Aminosäuren, Ammoniumsalze und -nitrate, Kaliumsalze (bevorzugt Chloride, Sulfate, Nitrate), Phosphorsäuresalze und/oder Salze von Phosphoriger Säure (bevorzugt Kaliumsalze und Ammoniumsalze). Insbesondere zu nennen sind in diesem Zusammenhang die NPK-Dünger, d.h. Düngemittel, die Stickstoff, Phosphor und Kalium enthalten, Kalkammonsalpeter, d.h. Düngemittel, die noch Calcium enthalten, Ammonsulfatsalpeter (Allgemeine Formel
Figure imgf000124_0001
Fertilizers which can be used according to the invention together with the compounds of the general formula (I) described above in more general terms are organic and inorganic nitrogen-containing compounds such as, for example, ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates), phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts). Particularly noteworthy in this context are the NPK fertilizers, ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers that still contain calcium, ammonium sulfate nitrate (General formula
Figure imgf000124_0001
NH4NO3), Ammonphosphat und Ammonsulfat. Diese Düngemittel sind dem Fachmann allgemein bekannt, siehe auch beispielsweise Ullmann's Encyclopedia of Industrial Chemistry, 5. Edition, Vol. A 10, Seiten 323 bis 431, Verlagsgesellschaft, Weinheim, 1987. NH4NO3), ammonium phosphate and ammonium sulfate. These fertilizers are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
Die Düngemittel können auch Salze aus Mikronährstoffen (bevorzugt Calcium, Schwefel, Bor, Mangan, Magnesium, Eisen, Bor, Kupfer, Zink, Molybdän und Kobalt) und Phytohormonen (z. B. Vitamin Bl und Indol-(III)essigsäure) oder Gemische davon enthalten. Erfindungsgemäß eingesetzte Düngemittel können auch weitere Salze wie Monoammoniumphosphat (MAP), Diammoniumphosphat (DAP), Kaliumsulfat, Kaliumchlorid, Magnesiumsulfat enthalten. Geeignete Mengen für die sekundären Nährstoffe oder Spurenelemente sind Mengen von 0,5 bis 5 Gew.-%, bezogen auf das gesamte The fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indole (III) acetic acid) or mixtures included. Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate, potassium chloride, magnesium sulfate. Suitable amounts for the secondary nutrients or trace elements are amounts of 0.5 to 5 wt .-%, based on the total
Düngemittel. Weitere mögliche Inhaltsstoffe sind Pflanzenschutzmittel, Insektizide, Fungizide, Safener oder Wachstumsregulatoren oder Gemische davon. Hierzu folgen weiter unten weitergehende Fertilizer. Further possible ingredients are crop protection agents, insecticides, fungicides, safeners or growth regulators or mixtures thereof. Further below follow this
Ausführungen. Versions.
Die Düngemittel können beispielsweise in Form von Pulvern, Granulaten, Prills oder Kompaktaten eingesetzt werden. Die Düngemittel können jedoch auch in flüssiger Form, gelöst in einem wässrigen Medium, eingesetzt werden. In diesem Fall kann auch verdünnter wässriger Ammoniak als The fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, diluted aqueous ammonia can also be used as
Stickstoffdüngemittel eingesetzt werden. Weitere mögliche Inhaltsstoffe für Düngemittel sind beispielsweise in Ullmann's Encyclopedia of Industrial Chemistry, 5. Auflage, 1987, Band A 10, Seiten 363 bis 401, DE-A 41 28 828, DE-A 19 05 834 und DE-A 196 31 764 beschrieben. Die allgemeine Zusammensetzung der Düngemittel, bei welchen es sich im Rahmen der vorliegenden Erfindung um Einzelnährstoff- und/oder Mehrnährstoffdünger handeln kann, beispielsweise aus Stickstoff, Kalium oder Phosphor, kann innerhalb eines breiten Bereichs variieren. Im Allgemeinen ist ein Gehalt von 1 bis 30 Gew.-% Stickstoff (bevorzugt 5 bis 20 Gew.-%), von 1 bis 20 Gew.-% Kalium (bevorzugt 3 bis 15 Gew.-%) und ein Gehalt von 1 bis 20 Gew.-% Phosphor (bevorzugt 3 bis 10 Gew.-%) vorteilhaft. Der Gehalt von Mikroelementen ist üblicherweise im ppm-Bereich, bevorzugt im Bereich von von 1 bis 1000 ppm. Nitrogen fertilizers are used. Further possible ingredients for fertilizers are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 , The general composition of the fertilizers, which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example nitrogen, potassium or phosphorus, may vary within a wide range. In general, a content of 1 to 30 wt .-% of nitrogen (preferably 5 to 20 wt .-%), from 1 to 20 wt .-% potassium (preferably 3 to 15 wt .-%) and a content of 1 to 20% by weight of phosphorus (preferably 3 to 10% by weight) is advantageous. The content of microelements is usually in the ppm range, preferably in the range of from 1 to 1000 ppm.
Im Rahmen der vorliegenden Erfindung können das Düngemittel sowie eine oder mehrere In the context of the present invention, the fertilizer and one or more
erfindungsgemäße Verbindungen der allgemeinen Formel (I) zeitgleich verabreicht werden. Es ist jedoch auch möglich, zunächst das Düngemittel und dann eine oder mehrere erfindungsgemäße Compounds according to the invention of the general formula (I) are administered at the same time. However, it is also possible, first the fertilizer and then one or more inventive
Verbindungen der allgemeinen Formel (I) oder zunächst eine oder mehrere Verbindungen der allgemeinen Formel (I) und dann das Düngemittel anzuwenden. Bei nicht zeitgleicher Anwendung einer oder mehrerer Verbindungen der allgemeinen Formel (I) und des Düngemittels erfolgt im Rahmen der vorliegenden Erfindung jedoch die Anwendung in funktionellem Zusammenhang, insbesondere innerhalb eines Zeitraums von im Allgemeinen 24 Stunden, bevorzugt 18 Stunden, besonders bevorzugt 12 Stunden, speziell 6 Stunden, noch spezieller 4 Stunden, noch weiter spezieller innerhalb 2 Stunden. In ganz besonderen Ausführungsformen der vorliegenden Erfindung erfolgt die Anwendung einer oder mehrerer erfindungsgemäßer Verbindungen der Formel (I) und des Düngemittels in einem zeitlichen Rahmen von weniger als 1 Stunden, vorzugsweise weniger als 30 Minuten, besonders bevorzugt weniger als 15 Minuten. Compounds of general formula (I) or first one or more compounds of general formula (I) and then to apply the fertilizer. In the case of non-simultaneous application of one or more compounds of the general formula (I) and of the fertilizer takes place in the context of However, the present invention relates to the use in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, more particularly 4 hours, even more particularly within 2 hours. In very particular embodiments of the present invention, the use of one or more compounds of the formula (I) and of the fertilizer according to the invention takes place in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
Bevorzugt ist die Verwendung von erfindungsgemäßen Verbindungen der allgemeinen Formel (I) auf Pflanzen aus der Gruppe der Nutzpflanzen, Zierpflanzen, Rasenarten, allgemein genutzte Bäume, die in öffentlichen und privaten Bereichen als Zierpflanzen Verwendungen finden, und Forstbestand. Der Forstbestand umfasst Bäume für die Herstellung von Holz, Zellstoff, Papier und Produkten die aus Teilen der Bäume hergestellt werden. Der Begriff Nutzpflanzen, wie hier verwendet, bezeichnet Kulturpflanzen, die als Pflanzen für die Gewinnung von Nahrungsmitteln, Futtermitteln, Treibstoffe oder für technische Zwecke eingesetzt werden. Preference is given to the use of compounds of the general formula (I) according to the invention on plants from the group of useful plants, ornamental plants, lawn species, generally used trees which are used as ornamental plants in public and private areas, and forest stands. The forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees. The term crops as used herein refers to crops used as plants for the production of food, feed, fuel or for technical purposes.
Zu den Nutzpflanzen zählen z. B. folgende Pflanzenarten: Triticale, Durum (Hartweizen), Turf, Reben, Getreide, beispielsweise Weizen, Gerste, Roggen, Hafer, Reis, Mais und Hirse; Rüben, beispielsweise Zuckerrüben und Futterrüben; Früchte, beispielsweise Kernobst, Steinobst und Beerenobst, Among the useful plants include z. The following plant species: triticale, durum (durum wheat), turf, vines, cereals, for example wheat, barley, rye, oats, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and berry fruit,
beispielsweise Äpfel, Birnen, Pflaumen, Pfirsiche, Mandeln, Kirschen und Beeren, z. B. Erdbeeren, Himbeeren, Brombeeren; Hülsenfrüchte, beispielsweise Bohnen, Linsen, Erbsen und Sojabohnen; For example, apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans;
Ölkulturen, beispielsweise Raps, Senf, Mohn, Oliven, Sonnenblumen, Kokos, Castorölpflanzen, Kakaobohnen und Erdnüsse; Gurkengewächse, beispielsweise Kürbis, Gurken und Melonen; Oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons;
Fasergewächse, beispielsweise Baumwolle, Flachs, Hanf und Jute; Citrusfrüchte, beispielsweise Orangen, Zitronen, Pampelmusen und Mandarinen; Gemüsesorten, beispielsweise Spinat, (Kopfj-Salat, Spargel, Kohlarten, Möhren, Zwiebeln, Tomaten, Kartoffeln und Paprika; Lorbeergewächse, beispielsweise Avocado, Cinnamomum, Kampfer, oder ebenso Pflanzen wie Tabak, Nüsse, Kaffee, Aubergine, Zuckerrohr, Tee, Pfeffer, Weinreben, Hopfen, Bananen, Naturkautschukgewächse sowie Zierpflanzen, beispielsweise Blumen, Sträucher, Laubbäume und Nadelbäume wie Koniferen. Diese Aufzählung stellt keine Limitierung dar. Fiber plants, for example cotton, flax, hemp and jute; Citrus fruits, such as oranges, lemons, grapefruit and mandarins; Vegetables such as spinach, (headj salad, asparagus, cabbage, carrots, onions, tomatoes, potatoes and peppers, laurel family, such as avocado, cinnamomum, camphor or even plants such as tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper , Vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers, this list is not limiting.
Als besonders geeignete Zielkulturen für die Anwendung des erfindungsgemäßen Verfahrens sind folgende Pflanzen anzusehen: Hafer, Roggen, Triticale, Durum, Baumwolle, Aubergine, Turf, Kernobst, Steinobst, Beerenobst, Mais, Weizen, Gerste, Gurke, Tabak, Reben, Reis, Getreide, Birne, Pfeffer, Bohnen, Sojabohnen, Raps, Tomate, Paprika, Melonen, Kohl, Kartoffel und Apfel. Als Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, seien beispielhaft genannt: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.. Particularly suitable target crops for the application of the method according to the invention are the following plants: oats, rye, triticale, durum, cotton, aubergine, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals , Pear, pepper, beans, soybeans, rape, tomato, paprika, melons, cabbage, potato and apple. Examples of trees which can be improved according to the method of the invention are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp , Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
Als bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Aus der Baumart Aesculus: A. hippocastanum, A. pariflora, A. carnea; aus der Baumart Platanus: P. aceriflora, P. occidentalis, P. racemosa; aus der Baumart Picea: P. abies; aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P. jeffregi, P. baksiana, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus. As preferred trees, which can be improved according to the method of the invention, may be mentioned: From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.
Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Aus der Baumart Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; aus der Baumart Eucalyptus: E. grandis, E. globulus und E. camadentis. As particularly preferred trees, which can be improved according to the method of the invention, may be mentioned: From the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus and E. camadentis.
Als besonders bevorzugte Bäume, die entsprechend dem erfindungsgemäßen Verfahren verbessert werden können, können genannt werden: Rosskastanie, Platanengewächs, Linde und Ahornbaum. Die vorliegende Erfindung kann auch an beliebigen Rasenarten („turfgrasses") durchgeführt werden, einschließlich„cool season turfgrasses" und„warm season turfgrasses". Beispiele für Rasenarten für die kalte Jahreszeit sind Blaugräser („blue grasses"; Poa spp.), wie„Kentucky bluegrass" (Poa pratensis L.), „rough bluegrass" (Poa trivialis L.),„Canada bluegrass" (Poa compressa L.),„annual bluegrass" (Poa annua L.),„upland bluegrass" (Poa glaucantha Gaudin),„wood bluegrass" (Poa nemoralis L.) und „bulbous bluegrass" (Poa bulbosa L.); Straussgräser („Bentgrass", Agrostis spp.), wie„creeping bentgrass" (Agrostis palustris Huds.),„colonial bentgrass" (Agrostis tenuis Sibth.),„velvet bentgrass" (Agrostis canina L.),„South German Mixed Bentgrass" (Agrostis spp. einschließlich Agrostis tenius Sibth., Agrostis canina L., und Agrostis palustris Huds.), und„redtop" (Agrostis alba L.); Schwingel („Fescues", Festucu spp.), wie„red fescue" (Festuca rubra L. spp. rubra),„creeping fescue" (Festuca rubra L.),„chewings fescue" (Festuca rubra commutata Gaud.),„sheep fescue" (Festuca ovina L.),„hard fescue" (Festuca longifolia Thuill.),„hair fescue" (Festucu capillata Lam.),„tall fescue" (Festuca arundinacea Schreb.) und„meadow fescue" (Festuca elanor L.); As particularly preferred trees that can be improved according to the method of the invention can be mentioned: horse chestnut, sycamore, linden and maple tree. The present invention may also be practiced on any turfgrasses, including "cool season turfgrasses" and "warm season turfgrasses." Examples of cold season turf species are blue grasses (Poa spp.), Such as "Kentucky bluegrass" (Poa pratensis L.), "rough bluegrass" (Poa trivialis L.), "Canada bluegrass" (Poa compressa L.), "annual bluegrass" (Poa annua L.), "upland bluegrass" (Poa glaucantha Gaudin), "wood bluegrass" (Poa nemoralis L.) and "bulbous bluegrass" (Poa bulbosa L.); ostrich grasses ("Bentgrass", Agrostis spp.), such as "creeping bentgrass" (Agrostis palustris Huds.), " colonial bentgrass "(Agrostis tenuis sib.)," velvet bentgrass "(Agrostis canina L.)," South German Mixed Bentgrass "(Agrostis spp including Agrostis tenius Sibth., Agrostis canina L., and Agrostis palustris Huds.), and "Redtop" (Agrostis alba L.), fescue ("Fescues", Festucu spp.), Such as "red fescue" (Festuca rubra L. spp. rubra), "creeping fescue" (Festuca rubra L.), "chewings fescue" (Festuca rubra commutata Gaud.), "sheep fescue" (Festuca ovina L.), "hard fescue" (Festuca longifolia Thuill.), "Hair fescue" (Festucu capillata lam.), "Tall fescue" (Festuca arundinacea Schreb.) And "meadow fescue" (Festuca elanor L.);
Lolch („ryegrasses", Lolium spp.), wie„annual ryegrass" (Lolium multiflorum Lam.),„perennial ryegrass" (Lolium perenne L.) und„italian ryegrass" (Lolium multiflorum Lam.); und Weizengräser ("wheatgrasses", Agropyron spp..), wie "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.),„crested wheatgrass" (Agropyron desertorum (Fisch.) Schult.) und "western wheatgrass" (Agropyron smithii Rydb.). Beispiele für weitere "cool season turfgrasses" sind "beachgrass" (Ammophila breviligulata Fern.),Lolium ("ryegrasses", Lolium spp.), Such as "annual ryegrass" (Lolium multiflorum Lam.), "Perennial ryegrass" (Lolium perenne L.) and "Italian ryegrass" (Lolium multiflorum Lam.); and wheat grasses ("wheatgrasses", Agropyron spp.), such as "fairway wheatgrass" (Agropyron cristatum (L.) Gaertn.), "crested wheatgrass" (Agropyron desertorum (fish.) Schult.) and "western wheatgrass" (Agropyron smithii Rydb.) Examples of other "cool season turfgrasses" are "beachgrass" (Ammophila breviligulata Fern.),
"smooth bromegrass" (Bromus inermis Leyss.), Schilf ("cattails") wie "Timothy" (Phleum pratense L.), "sand cattail" (Phleum subulatum L.), "orchardgrass" (Dactylis glomerata L.), "weeping alkaligrass" (Puccinellia distans (L.) Pari.) und "crested dog's-tail" (Cynosurus cristatus L.). Beispiele für "warm season turfgrasses" sind„Bermudagrass" (Cynodon spp. L. C. Rieh), "zoysiagrass" (Zoysia spp. Willd.),„St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze),„centipedegrass" (Eremochloa ophiuroides Munro Hack.),„carpetgrass" (Axonopus affinis Chase),„Bahia grass" (Paspalum notatum Flügge),„Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.),„buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.), "Blue gramma" (Bouteloua gracilis (H.B.K.) Lag. ex Griffiths),„seashore paspalum" (Paspalum vaginatum Swartz) und„sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" sind für die erfindungsgemäße Verwendung im Allgemeinen bevorzugt. Besonders bevorzugt sind Blaugras, Straussgras und„redtop", Schwingel und Lolch. Straussgras ist insbesondere bevorzugt. Besonders bevorzugt werden mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) Pflanzen der jeweils handelsüblichen oder in Gebrauch befindlichen Pflanzensorten behandelt. Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften ("Traits"), die sowohl durch konventionelle Züchtung, durch Mutagenese oder mit Hilfe rekombinanter DNA-Techniken, gezüchtet worden sind. Kulturpflanzen können demnach Pflanzen sein, die durch konventionelle Züchtungs- und "smooth bromegrass" (Bromus inermis leyss.), reeds ("cattails") such as "Timothy" (Phleum pratense L.), "sand cattail" (Phleum subulatum L.), "Orchardgrass" (Dactylis glomerata L.), " weeping alkaligrass "(Puccinellia distans (L.) Pari.) and" crested dog's-tail "(Cynosurus cristatus L.). Examples of "warm season turfgrasses" are "Bermudagrass" (Cynodon spp., LC Rieh), "zoysiagrass" (Zoysia spp. Willd.), "St. Augustine grass" (Stenotaphrum secundatum Walt Kuntze), "centipedegrass" (Eremochloa ophiuroides Munro Hack.), "Carpetgrass" (Axonopus affinis chase), "Bahia grass" (Paspalum notatum flügge), "Kikuyugrass" (Pennisetum clandestinum Höchst, ex Chiov.), "Buffalo grass" (Buchloe daetyloids (Nutt.) Engelm.) , "Blue gramma" (Bouteloua gracilis (HBK) lag. Ex Griffiths), "seashore paspalum" (Paspalum vaginatum Swartz) and "sideoats grama" (Bouteloua curtipendula (Michx. Torr.). "Cool season turfgrasses" are for the present invention Particularly preferred are bluegrass, ostrich grass and "redtop", fescue and lollypole. "Ostrich grass is particularly preferred." Particularly preferred compounds of the general formula (I) according to the invention are plants of the commercially available or in use P Plant varieties are understood to be plants having novel properties ("traits") that have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. Crop plants can therefore be plants produced by conventional breeding and
Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder Optimization methods or by biotechnological and genetic engineering methods or
Kombinationen dieser Methoden erhalten werden können, einschließlich der transgenen Pflanzen und einschließlich der durch Sortenschutzrechte schützbaren oder nicht schützbaren Pflanzensorten.  Combinations of these methods can be obtained, including transgenic plants and including those protected by plant breeders' rights or non-protectable plant varieties.
Das erfindungsgemäße Behandlungsverfahren kann somit auch für die Behandlung von genetisch modifizierten Organismen (GMOs), z. B. Pflanzen oder Samen, verwendet werden. Genetisch modifizierte Pflanzen (oder transgene Pflanzen) sind Pflanzen, bei denen ein heterologes Gen stabil in das Genom integriert worden ist. Der Begriff "heterologes Gen" bedeutet im wesentlichen ein Gen, das außerhalb der Pflanze bereitgestellt oder assembliert wird und das bei Einführung in das Zellkerngenom, das Chloroplastengenom oder das Hypochondriengenom der transformierten Pflanze dadurch neue oder verbesserte agronomische oder sonstige Eigenschaften verleiht, dass es ein interessierendes Protein oder Polypeptid exprimiert oder dasses ein anderes Gen, das in der Pflanze vorliegt bzw. andere Gene, die in der Pflanze vorliegen, herunterreguliert oder abschaltet (zum Beispiel mittels Antisense-Technologie, Co-suppressionstechnologie oder RNAi-Technologie [RNA Interference]). Ein heterologes Gen, das im Genom vorliegt, wird ebenfalls als Transgen bezeichnet. Ein Transgen, das durch sein spezifisches Vorliegen im Pflanzengenom definiert ist, wird als Transformations- bzw. transgenes Event bezeichnet. Zu Pflanzen und Pflanzensorten, die vorzugsweise mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden, zählen alle Pflanzen, die über Erbgut verfügen, das diesen Pflanzen besonders vorteilhafte, nützliche Merkmale verleiht (egal, ob dies durch Züchtung und/oder Biotechnologie erzielt wurde). Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die gegen einen oder mehrere abiotische Streßfaktoren resistent sind. Zu den abiotischen Streßbedingungen können zum Beispiel Hitze, Dürre, Kälte- und Trockenstress,, osmotischer Streß, Staunässe, erhöhter Bodensalzgehalt, erhöhtes The treatment method according to the invention can thus also for the treatment of genetically modified organisms (GMOs), z. As plants or seeds are used. Genetically modified plants (or transgenic plants) are plants in which a heterologous gene has been stably integrated into the genome. The term "heterologous gene" essentially means a gene which is provided or assembled outside the plant and which, when introduced into the nuclear genome, the chloroplast genome or the hypochondriacal genome, imparts new or improved agronomic or other properties to the transformed plant Expressing protein or polypeptide or that it downregulates or shuts down another gene present in the plant or other genes present in the plant (for example by means of antisense technology, Co-suppression technology or RNAi technology [RNA Interference]). A heterologous gene present in the genome is also referred to as a transgene. A transgene defined by its specific presence in the plant genome is referred to as a transformation or transgenic event. Plants and plant varieties which are preferably treated with the compounds of the general formula (I) according to the invention include all plants which have genetic material which gives these plants particularly advantageous, useful features (regardless of whether this is achieved by breeding and / or biotechnology has been). Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are resistant to one or more abiotic stress factors. The abiotic stress conditions may include, for example, heat, drought, cold and dry stress, osmotic stress, waterlogging, elevated soil salinity, increased levels of heat
Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkte Verfügbarkeit von Stickstoffnährstoffen, beschränkte Verfügbarkeit von Phosphornährstoffen oder Vermeidung von Schatten zählen. Exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
Pflanzen und Pflanzensorten, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind solche Pflanzen, die durch erhöhte Ertragseigenschaften gekennzeichnet sind. Ein erhöhter Ertrag kann bei diesen Pflanzen z. B. auf verbesserter Plants and plant varieties which can also be treated with the compounds of the general formula (I) according to the invention are those plants which are characterized by increased yield properties. An increased yield can in these plants z. B. on improved
Pflanzenphysiologie, verbessertem Pflanzenwuchs und verbesserter Pflanzenentwicklung, wie  Plant physiology, improved plant growth and improved plant development, such as
Wasserverwertungseffizienz, Wasserhalteeffizienz, verbesserter Stickstoffverwertung, erhöhter Kohlenstoffassimilation, verbesserter Photosynthese, verstärkter Keimkraft und beschleunigter Abreife beruhen. Der Ertrag kann weiterhin durch eine verbesserte Pflanzenarchitektur (unter Streß- und nicht- Streß-Bedingungen) beeinflußt werden, darunter frühe Blüte, Kontrolle der Blüte für die Produktion von Hybridsaatgut, Keimpflanzenwüchsigkeit, Pflanzengröße, Internodienzahl und -abstand, Water utilization efficiency, water retention efficiency, improved nitrogen utilization, increased carbon assimilation, improved photosynthesis, increased germination power and accelerated Abreife based. The yield may be further influenced by improved plant architecture (under stress and non-stress conditions), including early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internodal number and spacing,
Wurzelwachstum, Samengröße, Fruchtgröße, Schotengröße, Schoten- oder Ährenzahl, Anzahl der Samen pro Schote oder Ähre, Samenmasse, verstärkte Samenfüllung, verringerter Samenausfall, verringertes Schotenplatzen sowie Standfestigkeit. Zu weiteren Ertragsmerkmalen zählen Root growth, seed size, fruit size, pod size, pod or ear number, number of seeds per pod or ear, seed mass, increased seed filling, reduced seed failure, reduced pod popping and stability. Other income characteristics include
Samenzusammensetzung wie Kohlenhydratgehalt, Proteingehalt, Ölgehalt und Ölzusammensetzung, Nährwert, Verringerung der nährwidrigen Verbindungen, verbesserte Verarbeitbarkeit und verbesserte Lagerfähigkeit. Seed composition such as carbohydrate content, protein content, oil content and oil composition, nutritional value, reduction of nontoxic compounds, improved processability and improved shelf life.
Pflanzen, die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Hybridpflanzen, die bereits die Eigenschaften der Heterosis bzw. des Hybrideffekts exprimieren, was im allgemeinen zu höherem Ertrag, höherer Wüchsigkeit, besserer Gesundheit und besserer Resistenz gegen biotische und abiotische Streßfaktoren führt. Solche Pflanzen werden typischerweise dadurch erzeugt, dass man eine ingezüchtete pollensterile Elternlinie (den weiblichen Kreuzungspartner) mit einer anderen ingezüchteten pollenfertilen Elternlinie (dem männlichen Plants which can also be treated with the compounds of the general formula (I) according to the invention are hybrid plants which already express the properties of the heterosis or the hybrid effect, which generally results in higher yield, higher vigor, better health and better resistance to biotic and abiotic stress factors. Such plants will be typically produced by mixing an inbred male sterile parental line (the female crossover partner) with another inbred male fertile parent line (the male
Kreuzungspartner) kreuzt. Das Hybridsaatgut wird typischerweise von den pollensterilen Pflanzen geerntet und an Vermehrer verkauft. Pollensterile Pflanzen können manchmal (z. B. beim Mais) durch Entfahnen (d. h. mechanischem Entfernen der männlichen Geschlechtsorgane bzw. der männlichen Blüten), produziert werden; es ist jedoch üblicher, dass die Pollensterilität auf genetischen Crossing partner). The hybrid seed is typically harvested from the male sterile plants and sold to propagators. Pollen sterile plants can sometimes be produced (eg in maize) by delaving (i.e., mechanically removing male genitalia or male flowers); however, it is more common for male sterility to be genetic
Determinanten im Pflanzengenom beruht. In diesem Fall, insbesondere dann, wenn es sich bei dem gewünschten Produkt, da man von den Hybridpflanzen ernten will, um die Samen handelt, ist es üblicherweise günstig, sicherzustellen, dass die Pollenfertilität in Hybridpflanzen, die die für die Pollensterilität verantwortlichen genetischen Determinanten enthalten, völlig restoriert wird. Dies kann erreicht werden, indem sichergestellt wird, dass die männlichen Kreuzungspartner entsprechende Fertilitätsrestorergene besitzen, die in der Lage sind, die Pollenfertilität in Hybridpflanzen, die die genetischen Determinanten, die für die Pollensterilität verantwortlich sind, enthalten, zu restorieren. Genetische Determinanten für Pollensterilität können im Cytoplasma lokalisiert sein. Beispiele für cytoplasmatische Pollensterilität (CMS) wurden zum Beispiel für Brassica- Arten beschrieben (WO 92/005251, WO 95/009910, WO 98/27806, WO 2005/002324, WO 2006/021972 und US 6,229,072). Genetische Determinanten für Pollensterilität können jedoch auch im Zellkerngenom lokalisiert sein. Pollensterile Pflanzen können auch mit Methoden der pflanzlichen Biotechnologie, wie Gentechnik, erhalten werden. Ein besonders günstiges Mittel zur Erzeugung von pollensterilen Pflanzen ist in WO 89/10396 beschrieben, wobei zum Beispiel eine Ribonuklease wie eine Barnase selektiv in den Determinants in the plant genome is based. In this case, especially when the desired product, as one wants to harvest from the hybrid plants, is the seeds, it is usually beneficial to ensure that the pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility , completely restored. This can be accomplished by ensuring that the male crossing partners possess appropriate fertility restorer genes capable of restoring pollen fertility in hybrid plants containing the genetic determinants responsible for male sterility. Genetic determinants of pollen sterility may be localized in the cytoplasm. Examples of cytoplasmic male sterility (CMS) have been described, for example, for Brassica species (WO 92/005251, WO 95/009910, WO 98/27806, WO 2005/002324, WO 2006/021972 and US 6,229,072). However, genetic determinants of pollen sterility may also be localized in the nuclear genome. Pollen sterile plants can also be obtained using plant biotechnology methods such as genetic engineering. A particularly convenient means of producing male sterile plants is described in WO 89/10396, wherein, for example, a ribonuclease such as a barnase selectively into the
Tapetumzellen in den Staubblättern exprimiert wird. Die Fertilität kann dann durch Expression eines Ribonukleasehemmers wie Barstar in den Tapetumzellen restoriert werden (z. B. WO 91/002069).  Tapetumzellen is expressed in the stamens. The fertility can then be restorated by expression of a ribonuclease inhibitor such as barstar in the tapetum cells (eg WO 91/002069).
Pflanzen oder Pflanzensorten (die mit Methoden der Pflanzenbiotechnologie, wie der Gentechnik, erhalten werden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind herbizidtolerante Pflanzen, d. h. Pflanzen, die gegenüber einem oder mehreren vorgegebenen Herbiziden tolerant gemacht worden sind. Solche Pflanzen können entweder durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Herbizidtoleranz verleiht, erhalten werden. Plants or plant varieties (obtained by plant biotechnology methods, such as genetic engineering), which can also be treated with the compounds of the general formula (I) according to the invention, are herbicide-tolerant plants, i. H. Plants tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation conferring such herbicide tolerance.
Herbizidtolerante Pflanzen sind zum Beispiel glyphosatetolerante Pflanzen, d. h. Pflanzen, die gegenüber dem Herbizid Glyphosate oder dessen Salzen tolerant gemacht worden sind. So können zum Beispiel glyphosatetolerante Pflanzen durch Transformation der Pflanze mit einem Gen, das für das Enzym 5-Enolpyruvylshikimat-3-phosphatsynthase (EPSPS) kodiert, erhalten werden. Beispiele für solche EPSPS-Gene sind das AroA-Gen (Mutante CT7) des Bakterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), das CP4-Gen des Bakteriums Agrobacterium sp. (Barry et al., Curr. Topics Plant Physiol. (1992), 7, 139-145), die Gene, die für eine EPSPS aus der Petunie (Shah et al., Science (1986), 233, 478-481), für eine EPSPS aus der Tomate (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) oder für eine EPSPS aus Eleusine (WO 2001/66704) kodieren. Es kann sich auch um eine mutierte EPSPS handeln, wie sie zum Beispiel in EP-A 0837944, WO 2000/066746, WO Herbicide-tolerant plants are, for example, glyphosate-tolerant plants, ie plants that have been tolerated to the herbicide glyphosate or its salts. Thus, for example, glyphosate-tolerant plants can be obtained by transforming the plant with a gene encoding the enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS). Examples of such EPSPS genes are the AroA gene (mutant CT7) of the bacterium Salmonella typhimurium (Comai et al., Science (1983), 221, 370-371), the CP4 gene of the bacterium Agrobacterium sp. (Barry et al., Curr Topics Plant Physiol. (1992), 7, 139-145), the genes useful for petunia EPSPS (Shah et al al., Science (1986), 233, 478-481), for an EPSPS from tomato (Gasser et al., J. Biol. Chem. (1988), 263, 4280-4289) or for an EPSPS from Eleusine ( WO 2001/66704). It may also be a mutated EPSPS, as described for example in EP-A 0837944, WO 2000/066746, WO
2000/066747 oder WO 2002/026995 beschrieben ist. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-Oxidoreduktase-Enzym, wie es in US 5,776,760 und US 5,463,175 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man ein Gen exprimiert, das für ein Glyphosate-acetyltransferase- Enzym, wie es in z. B. WO 2002/036782, WO 2003/092360, WO 2005/012515 und WO 2007/024782 beschrieben ist, kodiert. Glyphosatetolerante Pflanzen können auch dadurch erhalten werden, dass man Pflanzen, die natürlich vorkommende Mutationen der oben erwähnten Gene, wie sie zum Beispiel in WO 01/024615 oder WO 2003/013226 beschrieben sind, enthalten, selektiert. 2000/066747 or WO 2002/026995. Glyphosate-tolerant plants can also be obtained by expressing a gene coding for a glyphosate oxidoreductase enzyme as described in US 5,776,760 and US 5,463,175. Glyphosate-tolerant plants may also be obtained by expressing a gene encoding a glyphosate acetyltransferase enzyme as described in, e.g. As WO 2002/036782, WO 2003/092360, WO 2005/012515 and WO 2007/024782 is encoded. Glyphosate-tolerant plants can also be obtained by selecting plants containing naturally-occurring mutations of the above-mentioned genes, as described, for example, in WO 01/024615 or WO 2003/013226.
Sonstige herbizidresistente Pflanzen sind zum Beispiel Pflanzen, die gegenüber Herbiziden, die das Enzym Glutaminsynthase hemmen, wie Bialaphos, Phosphinotricin oder Glufosinate, tolerant gemacht worden sind. Solche Pflanzen können dadurch erhalten werden, dass man ein Enzym exprimiert, das das Herbizid oder eine Mutante des Enzyms Glutaminsynthase, das gegenüber Hemmung resistent ist, entgiftet. Solch ein wirksames entgiftendes Enzym ist zum Beispiel ein Enzym, das für ein Other herbicide-resistant plants are, for example, plants which have been tolerated to herbicides which inhibit the enzyme glutamine synthase, such as bialaphos, phosphinotricin or glufosinate. Such plants can be obtained by expressing an enzyme which detoxifies the herbicide or a mutant of the enzyme glutamine synthase, which is resistant to inhibition. Such an effective detoxifying enzyme is, for example, an enzyme suitable for
Phosphinotricin-acetyltransferase kodiert (wie zum Beispiel das bar- oder pat-Protein aus Streptomyces- Arten). Pflanzen, die eine exogene Phosphinotricin-acetyltransferase exprimieren, sind zum Beispiel in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US Phosphinotricin acetyltransferase encoded (such as the bar or pat protein from Streptomyces species). Plants expressing an exogenous phosphinotricin acetyltransferase are described, for example, in US 5,561,236; US 5,648,477; US 5,646,024; US 5,273,894; US 5,637,489; US 5,276,268; US
5,739,082; US 5,908,810 und US 7,112,665 beschrieben. 5,739,082; US 5,908,810 and US 7,112,665.
Weitere herbizidtolerante Pflanzen sind auch Pflanzen, die gegenüber den Herbiziden, die das Enzym Hydroxyphenylpyruvatdioxygenase (HPPD) hemmen, tolerant gemacht worden sind. Bei den Further herbicide-tolerant plants are also plants tolerant to the herbicides which inhibit the enzyme hydroxyphenylpyruvate dioxygenase (HPPD). Both
Hydroxyphenylpyruvatdioxygenasen handelt es sich um Enzyme, die die Reaktion, in der para-Hydroxyphenylpyruvate dioxygenases are enzymes which inhibit the reaction in the
Hydroxyphenylpyruvat (HPP) zu Homogentisat umgesetzt wird, katalysieren. Pflanzen, die gegenüber HPPD-Hemmern tolerant sind, können mit einem Gen, das für ein natürlich vorkommendes resistentes HPPD-Enzym kodiert, oder einem Gen, das für ein mutiertes HPPD-Enzym gemäß WO 96/038567, WO 99/024585 und WO 99/024586 kodiert, transformiert werden. Eine Toleranz gegenüber HPPD- Hemmern kann auch dadurch erzielt werden, dass man Pflanzen mit Genen transformiert, die für gewisse Enzyme kodieren, die die Bildung von Homogentisat trotz Hemmung des nativen HPPD- Enzyms durch den HPPD-Hemmer ermöglichen. Solche Pflanzen und Gene sind in WO 99/034008 und WO 2002/36787 beschrieben. Die Toleranz von Pflanzen gegenüber HPPD-Hemmern kann auch dadurch verbessert werden, dass man Pflanzen zusätzlich zu einem Gen, das für ein HPPD-tolerantes Enzym kodiert, mit einem Gen transformiert, das für ein Prephenatdehydrogenase-Enzym kodiert, wie dies in WO 2004/024928 beschrieben ist. Weitere herbizidresistente Pflanzen sind Pflanzen, die gegenüber Acetolactatsynthase (ALS)-Hemmern tolerant gemacht worden sind. Zu bekannten ALS-Hemmern zählen zum Beispiel Sulfonylharnstoff, Imidazolinon, Triazolopyrimidine, Pyrimidinyloxy(thio)benzoate und/oder Sulfonylaminocarbonyl- triazolinon-Herbizide. Es ist bekannt, dass verschiedene Mutationen im Enzym ALS (auch als Hydroxyphenylpyruvate (HPP) is converted to homogentisate catalyze. Plants tolerant of HPPD inhibitors may be treated with a gene encoding a naturally occurring resistant HPPD enzyme, or a gene encoding a mutant HPPD enzyme as described in WO 96/038567, WO 99/024585 and WO 99/1998 / 024586, are transformed. Tolerance to HPPD inhibitors can also be achieved by transforming plants with genes encoding certain enzymes that allow the formation of homogentisate despite inhibition of the native HPPD enzyme by the HPPD inhibitor. Such plants and genes are described in WO 99/034008 and WO 2002/36787. The tolerance of plants to HPPD inhibitors can also be improved by transforming plants in addition to a gene coding for an HPPD-tolerant enzyme with a gene coding for a prephenate dehydrogenase enzyme, as described in WO 2004 / 024928 is described. Other herbicide-resistant plants are plants that have been tolerated to acetolactate synthase (ALS) inhibitors. Examples of known ALS inhibitors include sulfonylurea, imidazolinone, triazolopyrimidines, pyrimidinyloxy (thio) benzoates and / or sulfonylaminocarbonyltriazolinone herbicides. It is known that various mutations in the enzyme ALS (also known as
Acetohydroxysäure-Synthase, AHAS, bekannt) eine Toleranz gegenüber unterschiedlichen Herbiziden bzw. Gruppen von Herbiziden verleihen, wie dies zum Beispiel bei Tranel und Wright, Weed Science (2002), 50, 700-712, jedoch auch in US 5,605,011, US 5,378,824, US 5,141,870 und US 5,013,659, beschrieben ist. Die Herstellung von sulfonylharnstofftoleranten Pflanzen und imidazolinontoleranten Pflanzen ist in US 5,605,011 ; US 5,013,659; US 5,141,870; US 5,767,361 ; US 5,731,180; US Acetohydroxy acid synthase, AHAS) confer a tolerance to different herbicides or groups of herbicides, as for example in Tranel and Wright, Weed Science (2002), 50, 700-712, but also in US 5,605,011, US 5,378,824, US 5,141,870 and US 5,013,659. The preparation of sulfonylurea tolerant plants and imidazolinone tolerant plants is described in US 5,605,011; US 5,013,659; US 5,141,870; US 5,767,361; US 5,731,180; US
5,304,732; US 4,761,373; US 5,331,107; US 5,928,937; und US 5,378,824; sowie in der internationalen Veröffentlichung WO 96/033270 beschrieben. Weitere imidazolmontolerante Pflanzen sind auch in z. B. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 und WO 2006/060634 beschrieben. Weitere Sulfonylharnstoff- und imidazolmontolerante Pflanzen sind auch in z.B. WO 2007/024782 beschrieben. 5,304,732; US 4,761,373; US 5,331,107; US 5,928,937; and US 5,378,824; and in international publication WO 96/033270. Other imidazole-tolerant plants are also in z. WO 2004/040012, WO 2004/106529, WO 2005/020673, WO 2005/093093, WO 2006/007373, WO 2006/015376, WO 2006/024351 and WO 2006/060634. Other sulfonylurea and imidazole-tolerant plants are also disclosed in e.g. WO 2007/024782 described.
Weitere Pflanzen, die gegenüber ALS-Inhibitoren, insbesondere gegenüber Imidazolinonen, Other plants which are resistant to ALS inhibitors, in particular to imidazolinones,
Sulfonylharnstoffen und/oder Sulfamoylcarbonyltriazolinonen tolerant sind, können durch induzierte Mutagenese, Selektion in Zellkulturen in Gegenwart des Herbizids oder durch Mutationszüchtung erhalten werden, wie dies zum Beispiel für die Sojabohne in US 5,084,082, für Reis in WO 97/41218, für die Zuckerrübe in US 5,773,702 und WO 99/057965, für Salat in US 5,198,599 oder für die Sulfonylureas and / or sulfamoylcarbonyltriazolinones can be obtained by induced mutagenesis, selection in cell cultures in the presence of the herbicide or by mutation breeding, as for example for the soybean in US 5,084,082, for rice in WO 97/41218, for the sugar beet in US 5,773,702 and WO 99/057965, for salad in US 5,198,599 or for the
Sonnenblume in WO 2001/065922 beschrieben ist. Sunflower is described in WO 2001/065922.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind insektenresistente transgene Pflanzen, d.h. Pflanzen, die gegen Befall mit gewissen Zielinsekten resistent gemacht wurden. Solche Pflanzen können durch genetische Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated with the compounds of the general formula (I) according to the invention are insect-resistant transgenic plants, i. Plants that have been made resistant to attack by certain target insects. Such plants can be caused by genetic
Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Transformation or by selection of plants that contain a mutation that such a
Insektenresistenz verleiht, erhalten werden. Der Begriff "insektenresistente transgene Pflanze" umfaßt im vorliegenden Zusammenhang jeglicheInsect resistance. The term "insect-resistant transgenic plant" as used herein includes any
Pflanze, die mindestens ein Transgen enthält, das eine Kodiersequenz umfaßt, die für folgendes kodiert: Plant containing at least one transgene comprising a coding sequence coding for:
1) ein Insektizides Kristallprotein aus Bacillus thuringiensis oder einen Insektiziden Teil davon, wie die Insektiziden Kristallproteine, die von Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, zusammengestellt wurden, von Crickmore et al. (2005) in der Bacillus thuringiensis-Toxinnomenklatur aktualisiert (online bei: 1) an insecticidal crystal protein from Bacillus thuringiensis or an insecticidal portion thereof, such as the insecticidal crystal proteins collected by Crickmore et al., Microbiology and Molecular Biology Reviews (1998), 62, 807-813, by Crickmore et al. (2005) in the Bacillus thuringiensis toxin nomenclature (online at:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), oder Insektizide Teile davon, z.B. Proteine der Cry-Proteinklassen CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae oder Cry3Bb oder Insektizide Teile davon; oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/), or insecticidal parts thereof, eg proteins the cry protein classes CrylAb, CrylAc, CrylF, Cry2Ab, Cry3Ae or Cry3Bb or insecticidal parts thereof; or
2) ein Kristallprotein aus Bacillus thuringiensis oder einen Teil davon, der in Gegenwart eines zweiten, anderen Kristallproteins als Bacillus thuringiensis oder eines Teils davon insektizid wirkt, wie das binäre Toxin, das aus den Kristallproteinen Cy34 und Cy35 besteht (Moellenbeck et al., Nat. 2) a crystal protein from Bacillus thuringiensis or a part thereof which is insecticidal in the presence of a second, different crystal protein than Bacillus thuringiensis or a part thereof, such as the binary toxin consisting of the crystal proteins Cy34 and Cy35 (Moellenbeck et al., Nat ,
Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71, 1765-1774); oder Biotechnol. (2001), 19, 668-72; Schnepf et al., Applied Environm. Microb. (2006), 71, 1765-1774); or
3) ein Insektizides Hybridprotein, das Teile von zwei unterschiedlichen Insektiziden 3) an insecticidal hybrid protein containing parts of two different insecticides
Kristallproteinen aus Bacillus thuringiensis umfaßt, wie zum Beispiel ein Hybrid aus den Proteinen von 1) oben oder ein Hybrid aus den Proteinen von 2) oben, z. B. das Protein CrylA.105, das von dem Mais- Event MON98034 produziert wird (WO 2007/027777); oder Crystal proteins from Bacillus thuringiensis, such as a hybrid of the proteins of 1) above or a hybrid of the proteins of 2) above, e.g. The protein CrylA.105 produced by the corn event MON98034 (WO 2007/027777); or
4) ein Protein gemäß einem der Punkte 1) bis 3) oben, in dem einige, insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden 4) a protein according to any one of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding
Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierung oder Transformation induziert wurden, wie das Protein Cry3Bbl in Mais-Events MON863 oder MON88017 oder das Protein Cry3A im Mais-Event MIR 604; oder To expand target insect species and / or due to changes induced in the coding DNA during cloning or transformation, such as the protein Cry3Bbl in maize events MON863 or MON88017 or the protein Cry3A in the maize event MIR 604; or
5) ein Insektizides sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus oder einen Insektiziden Teil davon, wie die vegetativ wirkenden insektentoxischen Proteine (vegetative insecticidal proteins, VIP), die unter folgendem Link angeführt sind, z. B. Proteine der Proteinklasse VIP3Aa: 5) an insecticidal secreted protein from Bacillus thuringiensis or Bacillus cereus or an insecticidal part thereof, such as the vegetative insecticidal proteins (VIP) mentioned under the following link, e.g. B. Proteins of protein class VIP3Aa:
http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html oder http://www.lifesci.sussex.ac.uk/Home/Neil_Crickmore/Bt/vip.html or
6) ein sezerniertes Protein aus Bacillus thuringiensis oder Bacillus cereus, das in Gegenwart eines zweiten sezernierten Proteins aus Bacillus thuringiensis oder B. cereus insektizid wirkt, wie das binäre Toxin, das aus den Proteinen VIP1A und VIP2A besteht (WO 94/21795); oder 7) ein Insektizides Hybridprotein, das Teile von verschiedenen sezernierten Proteinen von Bacillus thuringiensis oder Bacillus cereus umfaßt, wie ein Hybrid der Proteine von 1) oder ein Hybrid der Proteine von 2) oben; oder 6) a secreted protein from Bacillus thuringiensis or Bacillus cereus which is insecticidal in the presence of a second secreted protein from Bacillus thuringiensis or B. cereus, such as the binary toxin consisting of the proteins VIP1A and VIP2A (WO 94/21795); or 7) an insecticidal hybrid protein comprising parts of various secreted proteins of Bacillus thuringiensis or Bacillus cereus, such as a hybrid of the proteins of 1) or a hybrid of the proteins of 2) above; or
8) ein Protein gemäß einem der Punkte 1) bis 3) oben, in dem einige, insbesondere 1 bis 10, Aminosäuren durch eine andere Aminosäure ersetzt wurden, um eine höhere Insektizide Wirksamkeit gegenüber einer Zielinsektenart zu erzielen und/oder um das Spektrum der entsprechenden 8) a protein according to any of items 1) to 3) above, in which some, in particular 1 to 10, amino acids have been replaced by another amino acid in order to achieve a higher insecticidal activity against a target insect species and / or the spectrum of the corresponding
Zielinsektenarten zu erweitern und/oder wegen Veränderungen, die in die Kodier- DNA während der Klonierang oder Transformation induziert wurden (wobei die Kodierung für ein Insektizides Protein erhalten bleibt), wie das Protein VIP3Aa im Baumwoll- Event COT 102. Target species and / or due to changes in the coding DNA during the Cloning or transformation (preserving the coding for an insecticidal protein), such as the protein VIP3Aa in cotton event COT 102.
Natürlich zählt zu den insektenresistenten transgenen Pflanzen im vorliegenden Zusammenhang auch jegliche Pflanze, die eine Kombination von Genen umfaßt, die für die Proteine von einer der oben genannten Klassen 1 bis 8 kodieren. In einer Ausführangsform enthält eine insektenresistente Pflanze mehr als ein Transgen, das für ein Protein nach einer der oben genannten 1 bis 8 kodiert, um das Spektrum der entsprechenden Zielinsektenarten zu erweitern oder um die Entwicklung einer Resistenz der Insekten gegen die Pflanzen dadurch hinauszuzögern, dass man verschiedene Proteine einsetzt, die für dieselbe Zielinsektenart insektizid sind, jedoch eine unterschiedliche Wirkungsweise, wie Bindung an unterschiedliche Rezeptorbindungsstellen im Insekt, aufweisen. Of course, insect-resistant transgenic plants in the present context also include any plant comprising a combination of genes encoding the proteins of any of the above classes 1 to 8. In one embodiment, an insect resistant plant contains more than one transgene encoding a protein of any one of the above 1 to 8 in order to extend the spectrum of the corresponding target insect species or to delay the development of resistance of the insects to the plants by use different proteins which are insecticidal for the same target insect species, but have a different mode of action, such as binding to different receptor binding sites in the insect.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind gegenüber abiotischen Streßfaktoren tolerant. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solch eine Streßresistenz verleiht, erhalten werden. Zu besonders nützlichen Pflanzen mit Streßtoleranz zählen folgende: a. Pflanzen, die ein Transgen enthalten, das die Expression und/oder Aktivität des Gens für die Poly(ADP-ribose)polymerase (PARP) in den Pflanzenzellen oder Pflanzen zu reduzieren vermag, wie dies in WO 2000/004173 oder EP 04077984.5 oder EP 06009836.5 beschrieben ist. b. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das die Expression und/oder Aktivität der für PARG kodierenden Gene der Pflanzen oder Pflanzenzellen zu reduzieren vermag, wie dies z.B. in WO 2004/090140 beschrieben ist; c. Pflanzen, die ein streßtoleranzförderndes Transgen enthalten, das für ein in Pflanzen funktionelles Enzym des Nicotinamidadenindinukleotid-Salvage-Biosynthesewegs kodiert, darunter Nicotinamidase, Nicotinatphosphoribosyltransferase, Nicotinsäuremononukleotid-adenyltransferase,Plants or plant varieties (obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated with the compounds of the general formula (I) according to the invention, are tolerant of abiotic stress factors. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such stress resistance. Particularly useful plants with stress tolerance include the following: a. Plants which contain a transgene capable of reducing the expression and / or activity of the gene for the poly (ADP-ribose) polymerase (PARP) in the plant cells or plants, as described in WO 2000/004173 or EP 04077984.5 or EP 06009836.5 is described. b. Plants containing a stress tolerance-enhancing transgene capable of reducing the expression and / or activity of the PARG-encoding genes of the plants or plant cells, e.g. in WO 2004/090140 is described; c. Plants containing a stress tolerance-enhancing transgene encoding a plant-functional enzyme of the nicotinamide adenine dinucleotide salvage biosynthetic pathway, including nicotinamidase, nicotinate phosphoribosyltransferase, nicotinic acid mononucleotide adenyltransferase,
Nicotinamidadenindinukleotidsynthetase oder Nicotinamidphosphoribosyl-transferase, wie dies z. B. in EP 04077624.7 oder WO 2006/133827 oder PCT/EP07/002433 beschrieben ist. Nicotinamide adenine dinucleotide synthetase or nicotinamide phosphoribosyltransferase as described e.g. As described in EP 04077624.7 or WO 2006/133827 or PCT / EP07 / 002433.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, weisen eine veränderte Menge, Qualität und/oder Lagerfähigkeit des Ernteprodukts und/oder veränderte Eigenschaften von bestimmten Bestandteilen des Ernteprodukts auf, wie zum Beispiel: Plants or plant varieties (which have been obtained by methods of plant biotechnology, such as genetic engineering), which can also be treated with the compounds of the general formula (I) according to the invention, have a modified amount, quality and / or shelf life of the Crop product and / or altered characteristics of certain components of the crop, such as:
1) Transgene Pflanzen, die eine modifizierte Stärke synthetisieren, die bezüglich ihrer chemisch- physikalischen Eigenschaften, insbesondere des Amylosegehalts oder des Amylose/Amylopektin- Verhältnisses, des Verzweigungsgrads, der durchschnittlichen Kettenlänge, der Verteilung der 1) Transgenic plants that synthesize a modified starch with respect to their physicochemical properties, in particular the amylose content or the amylose / amylopectin ratio, the degree of branching, the average chain length, the distribution of the
Seitenketten, des Viskositätsverhaltens, der Gelfestigkeit, der Stärkekorngröße und/oder Side chains, the viscosity behavior, the gel strength, the starch grain size and / or
Stärkekornmorphologie im Vergleich mit der synthetisierten Stärke in Wildtyppflanzenzellen oder - pflanzen verändert ist, so dass sich diese modifizierte Stärke besser für bestimmte Anwendungen eignet. Diese transgenen Pflanzen, die eine modifizierte Stärke synthetisieren, sind zum Beispiel in EP Starch grain morphology is altered in wildtype plant cells or plants compared to the synthesized starch, so that this modified starch is better suited for certain applications. These transgenic plants that synthesize a modified starch are described, for example, in EP
0571427, WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO  0571427, WO 95/004826, EP 0719338, WO 96/15248, WO 96/19581, WO 96/27674, WO 97/11188, WO 97/26362, WO 97/32985, WO 97/42328, WO 97/44472, WO 97/45545, WO 98/27212, WO 98/40503, WO 99/58688, WO 99/58690, WO 99/58654, WO 2000/008184, WO 2000/008185, WO 2000/28052, WO 2000/77229, WO 2001/12782, WO 2001/12826, WO 2002/101059, WO 2003/071860, WO 2004/056999, WO 2005/030942, WO 2005/030941, WO 2005/095632, WO 2005/095617, WO 2005/095619, WO 2005/095618, WO 2005/123927, WO 2006/018319, WO 2006/103107, WO
2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO 2006/108702, WO 2007/009823, WO 2000/22140, WO 2006/063862, WO 2006/072603, WO
2002/034923, EP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341, WOEP 06090134.5, EP 06090228.5, EP 06090227.7, EP 07090007.1, EP 07090009.7, WO 2001/14569, WO 2002/79410, WO 2003/33540, WO 2004/078983, WO 2001/19975, WO 95/26407, WO 96/34968, WO 98/20145, WO 99/12950, WO 99/66050, WO 99/53072, US 6,734,341, WO
2000/11192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 94/004693, WO 94/009144, WO 94/11520, WO 95/35026 bzw. WO 97/20936 beschrieben. 2) Transgene Pflanzen, die Nichtstärkekohlenhydratpolymere synthetisieren, oder 2000/11192, WO 98/22604, WO 98/32326, WO 2001/98509, WO 2001/98509, WO 2005/002359, US 5,824,790, US 6,013,861, WO 94/004693, WO 94/009144, WO 94/11520, WO 95/35026 and WO 97/20936, respectively. 2) Transgenic plants that synthesize non-starch carbohydrate polymers, or
Nichtstärkekohlenhydratpolymere, deren Eigenschaften im Vergleich zu Wildtyppflanzen ohne genetische Modifikation verändert sind. Beispiele sind Pflanzen, die Polyfructose, insbesondere des Inulin- und Levantyps, produzieren, wie dies in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 und WO 99/024593 beschrieben ist, Pflanzen, die alpha- 1,4-Glucane produzieren, wie dies in WO 95/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 und WO 2000/14249 beschrieben ist, Pflanzen, die alpha- 1,6-verzweigte alpha- 1,4-Glucane produzieren, wie dies in WO 2000/73422 beschrieben ist, und Pflanzen, die Alternan produzieren, wie dies in WO 2000/047727, EP 06077301.7, US 5,908,975 und EP 0728213 beschrieben ist.  Non-starch carbohydrate polymers whose properties are altered compared to wild-type plants without genetic modification. Examples are plants which produce polyfructose, in particular of the inulin and levan type, as described in EP 0663956, WO 96/001904, Wo 96/021023, WO 98/039460 and WO 99/024593, plants which are alpha-1 , 4-glucans, as described in WO 95/031553, US 2002/031826, US 6,284,479, US 5,712,107, WO 97/047806, WO 97/047807, WO 97/047808 and WO 2000/14249, plants which alpha-1,6-branched alpha-1,4-glucans as described in WO 2000/73422 and plants producing alternan as described in WO 2000/047727, EP 06077301.7, US 5,908,975 and EP 0728213 is.
3) Transgene Pflanzen, die Hyaluronan produzieren, wie dies zum Beispiel in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 und WO 2005/012529 beschrieben ist. Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Baumwollpflanzen mit veränderten Fasereigenschaften. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Fasereigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von Cellulosesynthasegenen enthalten, wie dies in WO 98/000549 beschrieben ist, b) Pflanzen wie Baumwollpflanzen, die eine veränderte Form von rsw2- oder rsw3 -homologen Nukleinsäuren enthalten, wie dies in WO 2004/053219 beschrieben ist; c) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der 3) Transgenic plants which produce hyaluronan, as described, for example, in WO 06/032538, WO 2007/039314, WO 2007/039315, WO 2007/039316, JP 2006/304779 and WO 2005/012529. Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated with the compounds of the general formula (I) according to the invention are plants such as cotton plants with altered fiber properties. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered fiber properties; These include: a) plants, such as cotton plants, containing an altered form of cellulose synthase genes as described in WO 98/000549; b) plants, such as cotton plants, containing an altered form of rsw2 or rsw3 homologous nucleic acids as described in U.S. Pat WO 2004/053219 is described; c) plants such as cotton plants with an increased expression of the
Saccharosephosphatsynthase, wie dies in WO 2001/017333 beschrieben ist; d) Pflanzen wie Baumwollpflanzen mit einer erhöhten Expression der Saccharosesynthase, wie dies in WO 2002/45485 beschrieben ist; e) Pflanzen wie Baumwollpflanzen bei denen der Zeitpunkt der Durchlaßsteuerung der Sucrose phosphate synthase as described in WO 2001/017333; d) plants such as cotton plants with increased expression of sucrose synthase, as described in WO 2002/45485; e) plants, such as cotton plants, where the timing of the passage control of the
Plasmodesmen an der Basis der Faserzelle verändert ist, z. B. durch Herunterregulieren der Plasmodesms is changed at the base of the fiber cell, z. B. by down-regulating the
faserselektiven ß-l,3-Glucanase, wie dies in WO 2005/017157 beschrieben ist; f) Pflanzen wie Baumwollpflanzen mit Fasern mit veränderter Reaktivität, z. B. durch Expression des N-Acetylglucosamintransferasegens, darunter auch nodC, und von Chitinsynthasegenen, wie dies in WO 2006/136351 beschrieben ist. fiber-selective ß-l, 3-glucanase, as described in WO 2005/017157; f) plants such as cotton plants with modified reactivity fibers, e.g. By expression of the N-acetylglucosamine transferase gene, including nodC, and chitin synthase genes, as described in WO 2006/136351.
Pflanzen oder Pflanzensorten (die nach Methoden der pflanzlichen Biotechnologie, wie der Gentechnik, erhalten wurden), die ebenfalls mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen wie Raps oder verwandte Brassica-Pflanzen mit veränderten Eigenschaften der Ölzusammensetzung. Solche Pflanzen können durch genetische Transformation oder durch Selektion von Pflanzen, die eine Mutation enthalten, die solche veränderten Öleigenschaften verleiht, erhalten werden; dazu zählen: a) Pflanzen wie Rapspflanzen, die Öl mit einem hohen Ölsäuregehalt produzieren, wie dies zum Beispiel in US 5,969,169, US 5,840,946 oder US 6,323,392 oder US 6,063, 947 beschrieben ist; b) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen Linolensäuregehalt produzieren, wie dies in US 6,270828, US 6,169,190 oder US 5,965,755 beschrieben ist. c) Pflanzen wie Rapspflanzen, die Öl mit einem niedrigen gesättigten Fettsäuregehalt produzieren, wie dies z. B. in US 5,434,283 beschrieben ist. Plants or plant varieties (obtained by plant biotechnology methods such as genetic engineering) which can also be treated with the compounds of the general formula (I) according to the invention are plants such as rape or related Brassica plants with altered properties of the oil composition. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered oil properties; These include: a) plants such as rape plants that produce high oleic oil, as described, for example, in US 5,969,169, US 5,840,946 or US 6,323,392 or US 6,063,947; b) plants such as oilseed rape plants which produce low linolenic acid oil, as described in US 6,270,828, US 6,169,190 or US 5,965,755. c) plants such as oilseed rape plants which produce oil with a low saturated fatty acid content, such as e.g. As described in US 5,434,283.
Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind Pflanzen, die Transformations-Events, oder eine Kombination von Transformations-Events, enthalten und die zum Beispiel in den Dateien von verschiedenen nationalen oder regionalen Behörden angeführt sind. Particularly useful transgenic plants that can be treated with the compounds of the general formula (I) according to the invention are plants which contain transformation events, or a combination of transformation events, and which, for example, in the files of various national or regional authorities are listed.
Besonders nützliche transgene Pflanzen, die mit den erfindungsgemäßen Verbindungen der allgemeinen Formel (I) behandelt werden können, sind beispielhaft Pflanzen mit einem oder mehreren Genen, die für ein oder mehrere Toxine kodieren, sind die transgenen Pflanzen, die unter den folgenden Particularly useful transgenic plants which can be treated with the compounds of the general formula (I) according to the invention are, by way of example, plants with one or more genes which code for one or more toxins, the transgenic plants which are the following
Handelsbezeichnungen angeboten werden: YIELD GARD® (zum Beispiel Mais, Baumwolle, Commercial names: YIELD GARD® (for example corn, cotton,
Sojabohnen), KnockOut® (zum Beispiel Mais), BiteGard® (zum Beispiel Mais), BT-Xtra® (zum Beispiel Mais), StarLink® (zum Beispiel Mais), Bollgard® (Baumwolle), Nucotn® (Baumwolle), Nucotn 33B® (Baumwolle), NatureGard® (zum Beispiel Mais), Protecta® und NewLeaf® (Kartoffel). Herbizidtolerante Pflanzen, die zu erwähnen sind, sind zum Beispiel Maissorten, Baumwollsorten und Sojabohnensorten, die unter den folgenden Handelsbezeichnungen angeboten werden: Roundup Ready® (Glyphosatetoleranz, zum Beispiel Mais, Baumwolle, Sojabohne), Liberty Link®  Soybeans), KnockOut® (for example corn), BiteGard® (for example maize), BT-Xtra® (for example corn), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton), Nucotn 33B® (cotton), NatureGard® (for example corn), Protecta® and NewLeaf® (potato). Herbicide-tolerant crops to be mentioned include, for example, corn, cotton and soybean varieties sold under the following tradenames: Roundup Ready® (glyphosate tolerance, for example corn, cotton, soybean), Liberty Link®
(Phosphinotricintoleranz, zum Beispiel Raps), IMI® (Imidazolinontoleranz) und SCS® (Phosphinotricin tolerance, for example rapeseed), IMI® (imidazolinone tolerance) and SCS®
(Sylfonylharnstofftoleranz), zum Beispiel Mais. Zu den herbizidresistenten Pflanzen (traditionell auf Herbizidtoleranz gezüchtete Pflanzen), die zu erwähnen sind, zählen die unter der Bezeichnung Clearfield® angebotenen Sorten (zum Beispiel Mais). (Sylfonylurea tolerance), for example corn. Herbicide-resistant plants (plants traditionally grown for herbicide tolerance) to be mentioned include the varieties sold under the name Clearfield® (for example corn).
Die erfindungsgemäß zu verwendenden Verbindungen der Formel (I) können in übliche Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, wasser- und ölbasierte Suspensionen, Pulver, Stäubemittel, Pasten, lösliche Pulver, lösliche Granulate, Streugranulate, Suspensions- Emulsions-Konzentrate, Wirkstoff- imprägnierte Naturstoffe, Wirkstoff- imprägnierte synthetischeThe compounds of the formula (I) to be used according to the invention can be converted into customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension emulsion concentrates, Active substance-impregnated natural substances, active ingredient-impregnated synthetic
Stoffe, Düngemittel sowie Feinstverkapselungen in polymeren Stoffen. Im Rahmen der vorliegenden Erfindung ist es insbesondere bevorzugt, wenn die Verbindungen der allgemeinen Formel (I) in der Form einer Sprühformulieruing verwendet werden. Die vorliegende Erfindung betrifft daher darüber hinaus auch eine Sprühformulierung zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischem Stress. Im Folgenden wird eine Substances, fertilizers and microencapsulation in polymeric substances. In the context of the present invention it is particularly preferred if the compounds of the general formula (I) are used in the form of a spray formulation. The present invention therefore further relates to a spray formulation for increasing the resistance of plants to abiotic stress. The following is a
Sprühformulierung näher beschrieben: Die Formulierungen zur Sprühapplikation werden in bekannter Weise hergestellt, z.B. durch Vermischen der zu verwendenden erfindungsgemäßen Verbindungen der allgmeinen Formel (I) mit Streckmitteln, also flüssigen Lösungsmitteln und/oder festen Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, also Emulgiermitteln und/oder Dispergiermitteln und/oder schaumerzeugenden Mitteln. Weitere übliche Zusatzstoffe, wie zum Beispiel übliche Streckmittel sowie Lösungs- oder Verdünnungsmittel, Farbstoffe, Netzmittel, Dispergiermittel, Emulgatoren, Entschäumer, Konservierungsmittel, sekundäre Verdickungsmittel, Kleber, Gibberelline und auch Wasser, können gegebenenfalls auch verwendet werden. Die Herstellung der Formulierungen erfolgt entweder in geeigneten Anlagen oder auch vor oder während der Anwendung. Als Hilfsstoffe können solche Stoffe Verwendung finden, die geeignet sind, dem Mittel selbst oder und/oder davon abgeleitete Zubereitungen (z.B. Spritzbrühen) besondere Eigenschaften zu verleihen, wie bestimmte technische Eigenschaften und/oder auch besondere biologische Eigenschaften. Als typische Hilfsmittel kommen in Frage: Streckmittel, Lösemittel und Trägerstoffe. Als Streckmittel eignen sich z.B. Wasser, polare und unpolare organische chemische Flüssigkeiten z.B. aus den Klassen der aromatischen und nicht-aromatischen Kohlenwasserstoffe (wie Paraffine, Spray formulation is described in more detail: The spray application formulations are prepared in a known manner, e.g. by mixing the compounds according to the invention of general formula (I) to be used with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents. Other conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water, may optionally also be used. The preparation of the formulations is carried out either in suitable systems or before or during use. Excipients which can be used are those which are suitable for imparting special properties to the composition itself or to preparations derived therefrom (for example spray mixtures), such as certain technical properties and / or special biological properties. Typical auxiliaries are: extenders, solvents and carriers. As extender, e.g. Water, polar and non-polar organic chemical liquids e.g. from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins,
Alkylbenzole, Alkylnaphthaline, Chlorbenzole), der Alkohole und Polyole (die ggf. auch substituiert, verethert und/oder verestert sein können), der Ketone (wie Aceton, Cyclohexanon), Ester (auch Fette und Öle) und (Poly-)Ether, der einfachen und substituierten Amine, Amide, Lactame (wie N- Alkylpyrrolidone) und Lactone, der Sulfone und Sulfoxide (wie Dimethylsysulfoxid). Alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may also be substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly) ethers, the simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, the sulfones and sulfoxides (such as dimethyl sulfoxide).
Im Falle der Benutzung von Wasser als Streckmittel können z.B. auch organische Lösemittel als Hilfslösungsmittel verwendet werden. Als flüssige Lösemittel kommen im wesentlichen in Frage: In the case of using water as an extender, e.g. also organic solvents can be used as auxiliary solvent. As liquid solvents are essentially in question:
Aromaten, wie Xylol, Toluol, oder Alkylnaphthaline, chlorierte Aromaten und chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzole, Chlorethylene oder Methylenchlorid, aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z.B. Erdölfraktionen, mineralische und pflanzliche Öle, Alkohole, wie Butanol oder Glykol sowie deren Ether und Ester, Ketone wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon, stark polare Lösungsmittel, wie Dimethylsulfoxid, sowie Wasser. Es können Farbstoffe wie anorganische Pigmente, z.B. Eisenoxid, Titanoxid, Ferrocyanblau und organische Farbstoffe, wie Alizarin-, Azo- und Metallphthalocyaninfarbstoffe und Spurennährstoffe wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink verwendet werden. Als Netzmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen, die Benetzung fördernden Stoffe in Frage. Vorzugsweise verwendbar sind Alkylnaphthalin-Sulfonate, wie Diisopropyl- oder Diisobutylnaphthalin-Sulfonate. Als Dispergiermittel und/oder Emulgatoren, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle zur Formulierung von agrochemischen Wirkstoffen üblichen nichtionischen, anionischen und kationischen Dispergiermittel in Betracht. Vorzugsweise verwendbar sind nichtionische oder anionische Dispergiermittel oder Gemische von nichtionischen oder anionischen Dispergiermitteln. Als geeignete nichtionische Dispergiermittel sind insbesondere Ethylenoxid- Propylenoxid-Blockpolymere, Alkylphenolpolyglykolether sowie Tristryrylphenolpolyglyko lether und deren phosphatierte oder sulfatierte Derivate zu nennen. Geeignete anionische Dispergiermittel sind insbesondere Ligninsulfonate, Polyacrylsäuresalze und Arylsulfonat-Formaldehydkondensate. Aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and Esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water. Dyes such as inorganic pigments such as iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used. Suitable wetting agents which may be present in the formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds. Preferably usable are alkylnaphthalene sulfonates such as diisopropyl or diisobutylnaphthalene sulfonates. Suitable dispersants and / or emulsifiers which may be present in the formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Particularly suitable nonionic dispersants are ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives. Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
Als Entschäumer können in den erfindungsgemäß verwendbaren Formulierungen alle zur Formulierung von agrochemischen Wirkstoffen üblichen schaumhemmenden Stoffe enthalten sein. Vorzugsweise verwendbar sind Silikonentschäumer und Magnesiumstearat. Defoamers which may be present in the formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds. Preferably usable are silicone defoamers and magnesium stearate.
Als Konservierungsmittel können in den erfindungsgemäß verwendbaren Formulierungen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe vorhanden sein. Beispielhaft genannt seien Dichlorophen und Benzylalkoholhemiformal. Preservatives which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
Als sekundäre Verdickungsmittel, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle für derartige Zwecke in agrochemischen Mitteln einsetzbaren Stoffe in Frage. Vorzugsweise in Betracht kommen Cellulosederivate, Acrylsäurederivate, Xanthan, modifizierte Tone und hochdisperse Kieselsäure. Suitable secondary thickeners which may be present in the formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
Als Kleber, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen alle üblichen in Beizmitteln einsetzbaren Bindemittel in Frage. Vorzugsweise genannt seien Suitable adhesives which may be present in the formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned
Polyvinylpyrrolidon, Polyvinylacetat, Polyvinylalkohol und Tylose. Als Gibberelline, die in den erfindungsgemäß verwendbaren Formulierungen enthalten sein können, kommen vorzugsweise diePolyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. Gibberellins which may be present in the formulations which can be used according to the invention are preferably those
Gibberelline AI, A3 (= Gibberellinsäure), A4 und A7 infrage, besonders bevorzugt verwendet man die Gibberellinsäure. Die Gibberelline sind bekannt (vgl. R. Wegler„Chemie der Pflanzenschutz- und Schädlingsbekämpfungsmittel", Bd. 2, Springer Verlag, 1970, S. 401-412). Gibberellins AI, A3 (= gibberellic acid), A4 and A7 in question, particularly preferably using the Gibberellic acid. The gibberellins are known (see R. Wegler "Chemie der Pflanzenschutz- und Schädlingsbekungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).
Weitere Additive können Duftstoffe, mineralische oder vegetabilische gegebenenfalls modifizierte Öle, Wachse und Nährstoffe (auch Spurennährstoffe), wie Salze von Eisen, Mangan, Bor, Kupfer, Kobalt, Molybdän und Zink sein. Weiterhin enthalten sein können Stabilisatoren wie Kältestabilisatoren, Oxidationsschutzmittel, Lichtschutzmittel oder andere die chemische und / oder physikalische Stabilität verbessernde Mittel. Die Formulierungen enthalten im Allgemeinen zwischen 0,01 und 98 Gew.-%, vorzugsweise zwischen 0,5 und 90 GEw. %, der Verbindung der allgemeinen Formel (I). Other additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also micronutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. Stabilizers such as cold stabilizers, antioxidants, light stabilizers or other chemical and / or physical stability improving agents may also be included. The formulations generally contain between 0.01 and 98% by weight, preferably between 0.5 and 90% by weight. %, the compound of general formula (I).
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) können in handelsüblichen The compounds of the general formula (I) according to the invention can be prepared in commercial
Formulierungen sowie in den aus diesen Formulierungen bereiteten Anwendungsformen in Mischung mit anderen Wirkstoffen wie Insektiziden, Lockstoffen, Sterilantien, Bakteriziden, Akariziden,Formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides,
Nematiziden, Fungiziden, wachstumsregulierenden Stoffen, Herbiziden, Safenern, Düngemitteln oder Semiochemicals vorliegen. Nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
Ferner lässt sich die beschriebene positive Wirkung der Verbindungen der Formel (I) auf die pflanzeneigenen Abwehrkräfte durch eine zusätzliche Behandlung mit insektziden, fungiziden oder bakteriziden Wirkstoffen unterstützen. Furthermore, the described positive effect of the compounds of the formula (I) on the plant's own defenses can be assisted by additional treatment with insecticidal, fungicidal or bactericidal active substances.
Bevorzugte Zeitpunkte für die Applikation der erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze zur Steigerung der Resistenz gegenüber abiotischem Stress sind Boden-, Stamm- und/oder Blattbehandlungen mit den zugelassenen Aufwandmengen. Preferred times for the application of the compounds of the general formula (I) according to the invention or their salts for increasing the resistance to abiotic stress are soil, stem and / or leaf treatments with the permitted application rates.
Die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) oder deren Salze können im The compounds of general formula (I) or their salts according to the invention can be described in
Allgemeinen darüber hinaus in ihren handelsüblichen Formulierungen sowie in den aus diesen In addition, in their commercial formulations as well as in these
Formulierungen bereiteten Anwendungsformen in Mischungen mit anderen Wirkstoffen, wie Formulations prepared uses in mixtures with other agents, such as
Insektiziden, Lockstoffen, Sterilantien, Akariziden, Nematiziden, Fungiziden, Bakteriziden, wachstumsregulierenden Stoffen, die Pflanzenreife beeinflussenden Stoffen, Safenern oder Herbiziden vorliegen. Insecticides, attractants, sterilants, acaricides, nematicides, fungicides, bactericides, growth regulators, the plant ripeness affecting substances, safeners or herbicides are present.
Die Erfindung soll durch die nachfolgenden biologischen Beispiele veranschaulicht werden, ohne sie jedoch darauf einzuschränken. Biologische Beispiele The invention will be illustrated by the following biological examples without, however, limiting them thereto. Biological examples
In vitro- Analysen Effekte des Phytohormons Abscisinsäure (ABA) auf das Verhalten von Pflanzen unter abiotischem Stress und der Wirkmechanismus von ABA sind in der Literatur beschrieben (vgl. Abrams et al, W097/23441, Park et al. Science, 2009, 324, 1068; Grill et al. Science, 2009, 324, 1064; Tanokura et al. Biophysics, 2011, 7, 123; Schroeder et al. Plant J. 2010, 61, 290). Daher kann man mit Hilfe eines geeigneten in vitro-Testsystems eine Korrelation zwischen der Wirkung von ABA und der Stressantwort einer Pflanze unter abiotischem Stress ableiten. Unter Wassermangel (Trockenstress) bilden Pflanzen das Phytohormon Abscisinsäure (ABA). Dieses bindet mit einem Co-Regulator (Regulatory Component of ABA-Receptor = RCAR nach Grill et al. Science, 2009, 324, 1064 oder PYR/PYL nach Cutler et al. Science, 2009, 324, 1068) an eine Phosphatase (z.B. ABU, eine Typ 2C Proteinphosphatase, auch als PP2C abgekürzt) und hemmt diese in ihrer Aktivität. In der Folge wird eine„downstream" Kinase (z.B. SnRK2) nicht mehr dephosphoryliert. Diese somit aktive Kinase schaltet über Phosphorylierung von Transkriptionsfaktoren (z.B. AREB/ABF, vgl. Yoshida et al., 2010, 61, 672) ein genetisches In Vitro Analyzes Effects of the phytohormone abscisic acid (ABA) on the behavior of plants under abiotic stress and the mechanism of action of ABA are described in the literature (Abrams et al., WO 97/24444, Park et al., Science, 2009, 324, Science, 2009, 324, 1064; Tanokura et al., Biophysics, 2011, 7, 123; Schroeder et al., Plant J. 2010, 61, 290). Therefore, a suitable in vitro test system can be used to derive a correlation between the effect of ABA and the stress response of a plant under abiotic stress. Under water shortage (drought stress) plants form the phytohormone abscisic acid (ABA). This binds with a co-regulator (Regulatory Component of ABA Receptor = RCAR according to Grill et al., Science, 2009, 324, 1064 or PYR / PYL by Cutler et al., Science, 2009, 324, 1068) to a phosphatase (eg ABU, a type 2C protein phosphatase, also abbreviated as PP2C) and inhibits them in their activity. As a result, a downstream kinase (e.g., SnRK2) is no longer dephosphorylated, and thus this active kinase switches on a genetic link via phosphorylation of transcription factors (e.g., AREB / ABF, see Yoshida et al., 2010, 61, 672)
Schutzprogramm zur Erhöhung der Trockenstresstoleranz an. Protection program to increase the dry stress tolerance.
In dem im Folgenden beschriebenen Assay wird die Hemmung der Phosphatase ABU über den Co- Regulator RCAR11/PYR1 aus Arabidopsis thaliana genutzt. Für die Aktivitätsbestimmung wurde die Dephosphorylierung von 4-Methylumbelliferylphosphat (MUP) bei 460nm gemessen. Der in vitro Assay wurde in Greiner 384-well PS-Mikroplatten F-well durchgeführt unter Verwendung von zwei Kontrollen, a) 0.5 % Dimethylsulfoxid (DMSO) sowie b) 5 μΜ Abscisinsäure (ABA). Der hier beschriebene Assay wurde im Allgemeinen mit Substratkonzentrationen der entsprechenden chemischen Testsubstanzen in einem Konzentrationsbereich von 0.1 μΜ bis 100 μΜ in einer Lösung aus DMSO und Wasser durchgeführt. Die so erhaltene Substanzlösung wurde gegebenenfalls mit Esterase aus  In the assay described below, the inhibition of the phosphatase ABU via the co-regulator RCAR11 / PYR1 from Arabidopsis thaliana is used. For activity determination, dephosphorylation of 4-methylumbelliferyl phosphate (MUP) at 460nm was measured. The in vitro assay was performed in Greiner 384-well PS microplates F-well using two controls, a) 0.5% dimethyl sulfoxide (DMSO) and b) 5 μΜ abscisic acid (ABA). The assay described herein was generally performed with substrate concentrations of the respective chemical test substances in a concentration range of 0.1 μΜ to 100 μΜ in a solution of DMSO and water. The substance solution thus obtained was optionally esterase
Schweineleber (EC 3.1.1.1) 3 h lang bei Raumtemperatur gerührt und 30 Min lang bei 4000rpm zentrifugiert. In jede Kavität der Mikroplatte wurde ein Gesamtvolumen von 45 μΕ gegeben, das sich wie folgt zusammensetzt: 1) 5μΕ Substanzlösung, d.h. a) DMSO 5% oder b) Abscisinsäure lösung oder c) die entsprechendePork liver (EC 3.1.1.1) was stirred for 3 h at room temperature and centrifuged for 30 min at 4000 rpm. Into each well of the microplate was added a total volume of 45 μΕ, composed as follows: 1) 5μΕ substance solution, i. a) DMSO 5% or b) abscisic acid solution or c) the corresponding
Beispielverbindung der allgemeinen Formel (I) gelöst in 5% DMSO. Example compound of general formula (I) dissolved in 5% DMSO.
2) 20μΕ Enzympuffermix, der sich aus a) 40 Vol% Enzympuffer (10 mL enthalten zu gleichen Volumenanteilen 500 mM Tris-HCl pH8, 500 mM NaCl, 3.33 mM MnCl2, 40 mM 2) 20μΕ enzyme buffer mix consisting of a) 40% by volume of enzyme buffer (10 mL in equal volumes of 500 mM Tris-HCl pH8, 500 mM NaCl, 3.33 mM MnCl 2 , 40 mM
Dithiothreitol (DTT)), b) 4 Vol% ABU -Verdünnung (Proteinstammlösung wurde so verdünnt, daß nach Zugabe eine Endkonzentration im Assay von 0.15 μg ABIl/well entsteht), c) 4 Vol% RCAR11 -Verdünnung (Enzymstock wurde so verdünnt, daß bei Zugabe der Verdünnung in den Enzympuffermix eine Endkonzentration im Assay von 0.30 μg Enzym/well entsteht), d) 5 Vol% Tween20 (1%), e) 47 Vol% H2O bi-dest zusammensetzt. 3) 20μΕ Substratmix, der sich aus a) 10 Vol% 500 mM Tris-HCl pH8, b) 10 Vol% 500 mM NaCl, c) 10 Vol% 3.33 mM MnCl2, d) 5 Vol% 25 mM MUP, 5 Vol% Tween20 (1%), 60 Vol% H20 bi-dest zusammensetzt. Dithiothreitol (DTT)), b) 4% ABU dilution by volume (protein stock solution was diluted to give a final concentration in the assay of 0.15 μg ABIl / well after addition), c) 4% by volume RCAR11 Dilution (Enzyme stock was diluted such that when the dilution was added to the enzyme buffer mix, a final assay concentration of 0.30 μg enzyme / well was generated), d) 5% by volume Tween20 (1%), e) 47% by volume H2O bi-dist composed. 3) 20μΕ substrate mix consisting of a) 10% by volume 500 mM Tris-HCl pH8, b) 10% by volume 500 mM NaCl, c) 10% by volume 3.33 mM MnCl 2 , d) 5% by volume 25 mM MUP, 5% by volume % Tween20 (1%), 60% by volume H 2 0 bi-dist.
Enzympuffermix und Substratmix wurden 5 Minuten vor der Zugabe angesetzt und auf eine Temperatur von 35 °C erwärmt. Nach vollständigem Pipettieren aller Lösungen und vollständiger Durchmischung wurde die Platte 20 Minuten lang bei 35 °C inkubiert. Abschließend erfolgte eine relative Enzyme buffer mix and substrate mix were prepared 5 minutes prior to addition and heated to a temperature of 35 ° C. After complete pipetting of all solutions and complete mixing, the plate was incubated at 35 ° C for 20 minutes. Finally, a relative
Fluoreszenzmessung bei 35 °C mit einem Mikroplatten-Lesegerät„POLARstar Optima" der Firma BMG Labtech unter Verwendung eines Anregungsfilters 340/10 nm und einem Emmissionsfilter von 460 nm. Die Wirkstärke der Verbindungen der allgemeinen Formel (I) wird in der nachfolgenden Tabelle unter Verwendung von Abscisinsäure (5μΜ) als Vergleichssubstanz (Abscisinsäure, No 53) nach folgender Einteilung angegeben: ++++ (Inhibition > 90 %), +++ (90 % > Inhibition _> 70%), ++ (70 % > Inhibition > 50%), + (50 % > Inhibition > 30%). Fluorescence measurement at 35 ° C. with a microplate reader "POLARstar Optima" from BMG Labtech using an excitation filter 340/10 nm and an emission filter of 460 nm. The potency of the compounds of the general formula (I) is shown in the table below of abscisic acid (5μΜ) as reference substance (abscisic acid, No.53) according to the following classification: ++++ (inhibition> 90%), +++ (90%> inhibition _> 70%), ++ (70%> inhibition > 50%), + (50%> inhibition> 30%).
In nachfolgender Tabelle A-1 sind die Effekte ausgewählter Verbindungen der allgemeinen Formel (I) im oben beschriebenen in vitro- Assay bei einer Konzentration von 5μΜ der betreffenden Substanz der allgemeinen Formel (I) in einer Lösung aus DMSO und Wasser aufgeführt. Die hierbei verwendeten Nummern der gemessenen Substanzen entsprechen den Nummern der Tabellenbeispiele 1-1 bis 1-50 Table A-1 below shows the effects of selected compounds of the general formula (I) in the above-described in vitro assay at a concentration of 5 μΜ of the relevant substance of the general formula (I) in a solution of DMSO and water. The numbers of the measured substances used herein correspond to the numbers of Table Examples 1-1 to 1-50
Tabelle A-1 Table A-1
No. Substanz ABU Inhibition  No. Substance ABU inhibition
1 1.1-34 ++  1 1.1-34 ++
2 1.1-35 +++  2 1.1-35 +++
3 1.1-40 ++  3 1.1-40 ++
4 1.1-50 ++++  4 1.1-50 ++++
5 1.1-54 ++  5 1.1-54 ++
6 1.1-62 +++  6 1.1-62 +++
7 1.1-92 ++++  7 1.1-92 ++++
8 1.1-204 +++  8 1.1-204 +++
9 1.2-4 +++  9 1.2-4 +++
10 1.2-34 ++++  10 1.2-34 ++++
11 1.2-35 ++++ No. Substanz ABU Inhibition11 1.2-35 ++++ No. Substance ABU inhibition
12 1.2-40 12 1.2-40
13 1.2-50  13 1.2-50
14 1.2-54  14 1.2-54
15 1.2-61  15 1.2-61
16 1.2-62  16 1.2-62
17 1.2-64  17 1.2-64
18 1.2-73  18 1.2-73
19 1.2-204  19 1.2-204
20 1.3-1  20 1.3-1
21 1.3-35  21 1.3-35
22 1.3-50  22 1.3-50
23 1.3-61  23 1.3-61
24 1.3-62  24 1.3-62
25 1.3-204  25 1.3-204
26 1.4-34  26 1.4-34
27 1.4-35  27 1.4-35
28 1.4-40  28 1.4-40
29 1.4-50  29 1.4-50
30 1.4-54  30 1.4-54
31 1.4-61  31 1.4-61
32 1.4-62  32 1.4-62
33 1.4-64  33 1.4-64
34 1.4-73  34 1.4-73
35 1.4-92  35 1.4-92
36 1.4-204  36 1.4-204
37 1.6-4  37 1.6-4
38 1.6-34  38 1.6-34
39 1.6-35  39 1.6-35
40 1.6-40  40 1.6-40
41 1.6-50  41 1.6-50
42 1.6-54  42 1.6-54
43 1.6-61  43 1.6-61
44 1.6-62  44 1.6-62
45 1.6-64  45 1.6-64
46 1.6-73 No. Substanz ABU Inhibition46 1.6-73 No. Substance ABU inhibition
47 1.6-92 ++++ 47 1.6-92 ++++
48 1.33-34 ++  48 1.33-34 ++
49 1.33-40 +++  49 1.33-40 +++
50 1.33-50 +++  50 1.33-50 +++
51 1.33-61 ++  51 1.33-61 ++
52 1.33-62 ++  52 1.33-62 ++
53 Abscisinsäure ++++  53 abscisic acid ++++

Claims

Patentansprüche claims
1. Verwendung substituierter N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I) oder deren Salze 1. Use of substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiaminoalkane of the general formula (I) or salts thereof
Figure imgf000144_0001
zur Steigerung der Stresstoleranz in Pflanzen gegenüber abiotischem Stress, sowie zur Steigerung des Pflanzenwachstums und/oder zur Erhöhung des Pflanzenertrags, wobei
Figure imgf000144_0001
to increase the stress tolerance in plants to abiotic stress, as well as to increase plant growth and / or increase plant yield, wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, A 1 , A 2 , A 3 and A 4 are the same or different and are each independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 has the same or different meanings as defined below,
X für Cyano, Halogen, (Ci-C8)-Alkyl, OR12, (Ci-Cio)-Haloalkyl, (Ci-C8)-Haloalkoxy, Aminocarbonyl, Aminothiocarbonyl steht, X is cyano, halogen, (C 1 -C 8 ) -alkyl, OR 12 , (C 1 -C 10) -haloalkyl, (C 1 -C 8 ) -haloalkoxy, aminocarbonyl, aminothiocarbonyl,
R1 für Wasserstoff, Halogen, Cyano, Nitro, NR^R1 OR12, S(0)mR13, Thiocyanato, R 1 is hydrogen, halogen, cyano, nitro, NR 1 R 1 OR 12 , S (0) m R 13 , thiocyanato,
Isothiocyanato, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)- Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl- (Ci-C8)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkinyl, Heteroaryl- (Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)-alkyl](aryl)silyl-(C2-C8)-alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)- alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)- alkenyl, Heterocyclyl-(C2-C8)-alkenyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminosulfonylamino, (C3-C8)- Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C8)-alkyl]silyl, Bis- [(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)-alkyl]silyl steht, Isothiocyanato, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, ( C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, pentafluorothio, (Ci-C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) - alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio ) -Cycloalkenyl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl- (C 1 -C 8 ) -alkyl, C ( 0) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N ( O) C- (C 1 -C 8 ) -alkyl, R 10 R u N- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkynyl, heteroaryl- (C 1 -C 8 ) -alkynyl, heterocyclyl (Ci-C8) -alkynyl, tris - silyl [(Ci-C 8) alkyl] (C 2 -C 8) -al kinyl, bis - [(Ci-C 8 ) alkyl] (aryl) silyl (C 2 -C 8 ) alkynyl, bis-aryl [(Ci-C 8 ) alkyl] silyl (C 2 -C 8 ) - alkynyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkynyl, aryl- (C 2 -C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkenyl, (C 1 -C 8 ) - Alkoxy (Ci-C8) alkoxy (Ci-C8) alkyl, (Ci-C8) -Alkylaminosulfonylamino, (C3-C8) - Cycloalkylaminosulfonylamino, diazo, Aryldiazo, tris - [(Ci-C 8) -alkyl ] silyl, bis- [(Ci-C 8 ) alkyl] (aryl) silyl, bis-aryl [(Ci-C 8 ) alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, Cyano- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C8)- alkylsulfonyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cg)- Haloalkyl, Halo-(C2-C8)-alkinyl, Halo-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkylsulfonyl, Heterocyclyl-(Ci-C8)-alkylsulfonyl, (C4-C8)-Cycloalkenyl, (C4-C8)-Cycloalkenyl- (Ci-C8)-alkyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-Cs)- Alkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Bis-[(Ci-C8)- Alkyljaminocarbonyl stehen, R 2 and R 6 independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl, cyano- (C 1 -C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkyl- (C 1 -C 4) -cycloalkyl, C 8 ) -alkyl, (C 1 -C 8 ) -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 8 ) -cycloalkylsulfonyl, heterocyclylsulfonyl, aryl- (C 1 -C 8 ) -alkylsulfonyl, (C 1 -C 8 ) -alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C8) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C8) alkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (Ci-C 8) haloalkylcarbonyl, (C 2 -C 8 ) Alkenyl, (C 2 -C 8 ) alkynyl, (Ci-Cg) haloalkyl, halo (C 2 -C 8 ) alkynyl, halo (C 2 -C 8 ) alkenyl, (Ci-C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, amino, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) alkylsulfonyl, heterocyclyl (Ci-C8) alkylsulfonyl, (C4-C8) cycloalkenyl, (C4-C8) cycloalkenyl (Ci-C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, (Ci-Cs) - alkylaminocarbonyl, (C3-C8) cycloalkylaminocarbonyl, bis - [(Ci-C 8) - Alkyljaminocarbon yl stand,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-Cg)-Alkyl, (C2-C8)-Alkenyl, Halogen, (Ci-C8)-Haloalkyl, Aryl, Heteroaryl, (C3-C8)-Cycloalkyl, Heterocyclyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy- (Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino-(Ci-C8)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, (C 1 -C 6 ) -alkyl, (C 2 -C 8 ) -alkenyl, halogen, (C 1 -C 8 ) -haloalkyl, aryl, heteroaryl, ( C 3 -C 8 ) -cycloalkyl, heterocyclyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -cycloalkyl, heterocyclyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl; 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, bis - [(C 1 -C 8 ) -alkyl] amino- (C 1 -C 8 -alkyl) 8 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl , R 10 R u is N (O) C- (C 1 -C 8 ) -alkyl, R 10 is R u N- (C 1 -C 8 ) -alkyl, m is 0, 1 or 2, n is 1, 2 or 3 stands,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or partially saturated, optionally interrupted by heteroatoms and
gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  optionally further substituted 3 to 10-membered monocyclic or bicyclic ring form, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or partially saturated, optionally interrupted by heteroatoms and
gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, optionally further substituted 3 to 10-membered monocyclic or bicyclic ring form, or R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 6 with the nitrogen atoms to which they are attached and the carbon atoms connecting the nitrogen atoms form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder für Amino, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Haloalkyl, (C3-C8)-Halocycloalkyl, (C i-C8)-Cycloalkenyl, Aryl, Heteroaryl, Heterocyclyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-Cg)-Alkoxycarbonyl-(Ci-Cg)-alkyl, Aryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkoxycarbonyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)- alkoxycarbonyl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkoxycarbonyl-(Ci-C8)-alkyl, Aminocarbonyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminocarbonyl-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylaminocarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkylaminocarbonyl-(Ci-C8)- alkyl, (Ci-C8)-Alkylamino, Arylamino, (C3-C8)-Cycloalkylamino, Aryl-(Ci-C8)- alkylamino, Heteroaryl-(Ci-C8)-alkylamino, Heteroarylamino, Heterocyclylamino, Aryloxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Heteroaryloxy-(Ci-C8)-alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (C2-C8)-Alkenylamino, (C2-C8)-Alkinylamino, Bis- [(Ci-C8)-alkenyl]amino, Aryloxy, Bis-[(Ci-C8)-Alkyl]amino, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)-alkenyl, Heterocyclyl-(C2-C8)-alkenyl, Aryloxycarbonyl-(Ci-C8)- alkyl, Heteroaryloxycarbonyl-(Ci-C8)-alkyl, Bis[(Ci-C8)-alkyl]aminocarbonyl-(Ci-C8)- alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, Cyano-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)- alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonylamino-(Ci-C8)-alkyl, (C3-C8)- Cycloalkylsulfonylamino-(Ci-C8)-alkyl, Arylsulfonylamino-(Ci-C8)-alkyl, R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or amino, (Ci-C 8) -alkyl, (C 3 -C 8) -cycloalkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (Ci-C 8) haloalkyl, ( C 3 -C 8 ) -halocycloalkyl, (C 1 -C 8 ) -cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl, heterocyclyl- (C 1 -C 8 -cycloalkyl) 8 ) -alkyl, (Ci-Cg) -alkoxycarbonyl (Ci-Cg) -alkyl, aryl (Ci-C 8 ) -alkoxycarbonyl (Ci-C 8 ) -alkyl, (C 3 -C 8 ) -cycloalkoxycarbonyl - (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) - alkoxycarbonyl (Ci-C 8) alkyl, heteroaryl (Ci-C8) alkoxycarbonyl ( Ci-C8) alkyl, aminocarbonyl (Ci-C8) alkyl, (Ci-C8) alkylaminocarbonyl (Ci-C8) alkyl, (C 3 -C 8) - cycloalkylaminocarbonyl (Ci C 8) alkyl, aryl (Ci-C8) alkylaminocarbonyl (Ci-C8) - alkyl, (Ci-C 8) alkylamino, arylamino, (C3-C8) cycloalkylamino, aryl (C -C 8) - alkylamino, heteroaryl (Ci-C 8) alkylamino, heteroarylamino, heterocyclylamino, aryloxy (Ci-C8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) -alkyl , heteroaryloxy- (Ci-C 8) alkyl, (C2-C8) alkenyl, (C2-C8) -alkynyl, (C2-C 8) -alkenylamino, (C2-C8) -alkynylamino, bis [(Ci-C 8) alkenyl] amino, aryloxy, bis - [(Ci-C 8) -alkyl] amino, aryl (C2-C 8) alkenyl, heteroaryl (C 2 -C 8) alkenyl, heterocyclyl- (C 2 -C 8) alkenyl, aryloxycarbonyl (Ci-C 8) - alkyl, heteroaryloxycarbonyl, (Ci-C 8) -alkyl , bis [(Ci-C 8) alkyl] aminocarbonyl (Ci-C8) - alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, cyano (Ci-C8) - alkyl, (Ci-C 8) alkoxy (Ci-C 8) - alkoxy- (Ci-C 8) alkyl, (Ci-C8) alkylsulfonylamino (Ci-C 8) alkyl, (C 3 -C 8) - Cycloalkylsulfonylamino- (Ci-C 8) alkyl, arylsulfonylamino (Ci-C 8) alkyl,
Heteroarylsulfonylamino-(Ci-C8)-alkyl, Heterocyclylsulfonylamino-(Ci-C8)-alkyl, Bis- [(Ci-C8)-alkyl]aminosulfonyl-(Ci-C8)-alkyl steht, und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cs)- Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy- (Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl- (Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR12, SO2R13, (Ci-C8)-Alkyl-HN02S-, (C3-C8)- Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- Alkoxycarbonyl, Heteroaryl-(Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C i-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Cs)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl steht und Heteroarylsulfonylamino- (C 1 -C 8 ) -alkyl, heterocyclylsulfonylamino- (C 1 -C 8 ) -alkyl, bis- [(C 1 -C 8 ) -alkyl] -aminosulfonyl- (C 1 -C 8 ) -alkyl, and R 11 are the same or are different and independently of one another for hydrogen, (Ci-Cs) - alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (Ci-C 8 ) -cyanoalkyl, (Ci-Cio ) -Haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, ( C 4 -C 10) -halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) - Alkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl - (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio) -cycloalkenyl - (Ci-C 8) alkyl, COR 12, SO 2 R 13, (Ci-C8) alkyl-S- HN0 2, (C 3 -C 8) - cycloalkyl HN0 2 S-, heterocyclyl, (Ci- C8) alkoxycarbonyl (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, aryl (Ci-C 8) -Alkoxyca rbonyl- (Ci-C 8) alkyl, aryl (Ci-C8) - alkoxycarbonyl, heteroaryl- (Ci-C8) alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) alkynyloxycarbonyl, heterocyclyl (Ci-C 8) -alkyl, hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci- C 8 ) -cyanoalkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -Cio) - Halocycloalkyl, (Ci-Cio) -cycloalkenyl, (C4-Cio) -halocycloalkenyl, (Ci-Cs) - Alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 8 ) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C4-C10) - cycloalkenyl (Ci-C 8) alkyl, (Ci-C8) alkoxycarbonyl (Ci -C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, hydroxycarbonyl (C -C 8) alkyl, heterocyclyl, heterocyclyl (Ci-C 8) -alkyl and
R13 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Cs)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) ) -Halocycloalkenyl, (C 1 -C 5 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) - alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C8) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio) -Cycloalkenyl- (Ci-C 8 ) alkyl, NR 10 R U.
Verwendung gemäß Anspruch 1 , wobei in Formel (I) Use according to claim 1, wherein in formula (I)
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, für Cyano, Halogen, (Ci-C6)-Alkyl, OR12, (Ci-C6)-Haloalkyl, (Ci-C6)-Haloalkoxy, A 1 , A 2 , A 3 and A 4 are the same or different and are independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 each have the same or different meanings as defined below, for Cyano, halogen, (C 1 -C 6 ) -alkyl, OR 12 , (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy,
Aminocarbonyl, Aminothiocarbonyl steht, für Wasserstoff, Halogen, Cyano, Nitro, NR10RU, OR12, S(0)mR13, Thiocyanato, Isothiocyanato, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, Pentafluorthio, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, (Ci-C6)- Haloalkoxy-(Ci-C6)-haloalkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C7)-Cycloalkenyl- (Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkylcarbonyl-(Ci-C6)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C6)-alkyl, R10RuN(O)C- (Ci-C6)-alkyl, R10RuN-(Ci-C6)-alkyl, Aryl-(Ci-C6)-alkinyl, Heteroaryl-(Ci-C6)-alkinyl, Heterocyclyl-(Ci-C6)-alkinyl, Tris-[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, Bis-[(Ci-C6)- alkyl](aryl)silyl-(C2-C6)-alkinyl, Bis-aryl[(Ci-C6)-alkyl]silyl-(C2-C6)-alkinyl, (C3-C6)- Cycloalkyl-(C2-C6)-alkinyl, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)-alkenyl, Heterocyclyl- (C2-C6)-alkenyl, (C3-C6)-Cycloalkyl-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkylaminosulfonylamino, (C3-C6)-Cycloalkylaminosulfonylamino, Diazo, Aryldiazo, Tris-[(Ci-C6)-alkyl]silyl, Bis-[(Ci-C6)-alkyl](aryl)silyl, Bis-aryl[(Ci-C6)-alkyl]silyl steht, Aminocarbonyl, aminothiocarbonyl, represents hydrogen, halogen, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13, thiocyanato, isothiocyanato, (Ci-C 6) -alkyl, (C 2 -C 6) Alkenyl, (C 2 -C 6 ) alkynyl, (C 1 -C 6 ) haloalkyl, (C 2 -C 6 ) haloalkenyl, (C 2 -C 6 ) haloalkynyl, (C 3 -C 7 ) cycloalkyl , (C 3 -C 7) halocycloalkyl, (C 4 -C 7) cycloalkenyl, (C 4 -C 7) -Halocycloalkenyl, pentafluorosulfanyl, (Ci-C6) alkoxy (Ci-C 6) -haloalkyl , (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, Heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 7 ) -cycloalkenyl- (C 1 -C 6 ) -alkyl, heterocyclyl , heterocyclyl (Ci-C 6) alkyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, (Ci-C 6) - alkylthio, (Ci-C 6) alkyl, (C -C 6) -Haloalkylthio- (Ci-C 6) alkyl, (Ci-C6) alkylcarbonyl (Ci-C 6) - alkyl, C (0) OR 12, C (O) NR 10 R u, C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 6 ) -alkyl, R 10 R u N (O) C- (C 1 -C 6 ) -alkyl, R 10 R u N- (C 1 -C 6 ) -alkyl , Aryl- (C 1 -C 6 ) -alkynyl, heteroaryl- (C 1 -C 6 ) -alkynyl, heterocyclyl- (C 1 -C 6 ) -alkynyl, tris - [(C 1 -C 6 ) -alkyl] silyl- (C 2 -C 6) alkynyl, - bis [(Ci-C 6) - alkyl] (aryl) silyl (C 2 -C 6) -alkynyl, bis-aryl [(Ci-C6) alkyl] silyl (C 2 -C 6) -alkynyl, (C 3 -C 6) - cycloalkyl, (C 2 -C 6) alkynyl, aryl (C 2 -C 6) alkenyl, heteroaryl (C 2 -C 6) alkenyl, heterocyclyl - (C 2 -C 6) alkenyl, (C3-C6) cycloalkyl (C 2 -C 6) alkenyl, (Ci-C6) alkoxy (Ci-C6) alkoxy (Ci-C 6 ) - alkyl, (C 1 -C 6 ) -alkylaminosulfonylamino, (C 3 -C 6 ) -cycloalkylaminosulfonylamino, diazo, aryldiazo, tris - [(C 1 -C 6 ) -alkyl] silyl, bis - [(C 1 -C 6 ) -alkyl] (aryl) silyl, bis-aryl [(Ci-C 6 ) alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, Cyano-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylsulfonyl, Arylsulfonyl, R 2 and R 6 are each independently hydrogen, (Ci-C6) alkyl, (C3-C6) cycloalkyl, cyano (Ci-C6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkylsulfonyl, arylsulfonyl,
Heteroarylsulfonyl, (C3-C6)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C6)- alkylsulfonyl, (Ci-C6)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C6)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C6)-Alkoxycarbonyl, Aryl-(Ci-C6)- alkoxycarbonyl, (Ci-C6)-Haloalkylcarbonyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-Ce)- Haloalkyl, Halo-(C2-C6)-alkinyl, Halo-(C2-C6)-alkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Amino, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkylsulfonyl, Heterocyclyl- (Ci-C6)-alkylsulfonyl, (C4-C6)-Cycloalkenyl, (C4-C6)-Cycloalkenyl-(Ci-C6)-alkyl, (C2-C6)- Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, (Ci-C6)-Alkylaminocarbonyl, (C3-C6)- Cycloalkylaminocarbonyl, Bis-[(Ci-C6)-Alkyl]aminocarbonyl stehen, 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 6) - Alkoxycarbonyl, aryl- (C 1 -C 6) alkoxycarbonyl, (C 1 -C 6) -haloalkylcarbonyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 1 -C 6) -haloalkyl, halo- (C 2 -C 6) -alkynyl, halo- (C 2 -C 6) alkenyl, (Ci-C6) alkoxy (Ci-C 6) alkyl, amino, (Ci-C6) alkoxy (Ci -C 6 ) alkoxy- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkylsulfonyl, heterocyclyl- (C 1 -C 6 ) -alkylsulfonyl, (C 4 -C 6 ) -cycloalkenyl, (C 4 -C 6 ) cycloalkenyl (Ci-C 6) alkyl, (C 2 -C 6) - alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, (Ci-C6) alkylaminocarbonyl, (C3-C6) - cycloalkylaminocarbonyl, bis- [(C 1 -C 6) -alkyl] aminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, Halogen,R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyl, halogen,
(Ci-C6)-Haloalkyl, Aryl, Heteroaryl, (C3-C6)-Cycloalkyl, Heterocyclyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkoxy-(Ci-C6)-alkyl, (Ci-C6)- Haloalkylthio-(Ci-C6)-alkyl, Bis-[(Ci-C6)-Alkyl]amino-(Ci-C6)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C6)-alkyl, R10RuN(O)C-(Ci-C6)-alkyl, R10RuN-(Ci-C6)- alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, (Ci-C 6) -haloalkyl, aryl, heteroaryl, (C 3 -C 6) cycloalkyl, heterocyclyl, (Ci-C6) alkoxy (Ci-C 6) - alkyl, (Ci-C 6) - Alkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, bis [ (C 1 -C 6) -alkyl] amino- (C 1 -C 6) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 are alkyl, m - (0) C- (Ci-C 6) alkyl, R 10 R u N (O) C- (Ci-C 6) alkyl, R 10 R u N- (Ci-C 6) is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, form part-saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or R 3 and R 7 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, R 4 and R 8 with the carbon atoms to they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome R 2 and R 6 with the nitrogen atoms to which they are attached, as well as the nitrogen atoms
verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder  connecting carbon atoms form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2 und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2 und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R5 für Amino, (Ci-C6)-Alkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (Ci-C6)- Haloalkyl, (C3-C6)-Halocycloalkyl, (C i-C6)-Cycloalkenyl, Aryl, Heteroaryl, Heterocyclyl, Aryl-R 5 is amino, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) - haloalkyl , (C 3 -C 6) -halocycloalkyl, (C 1 -C 6) -cycloalkenyl, aryl, heteroaryl, heterocyclyl, aryl-
(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (Ci-C6)-Alkoxycarbonyl- (Ci-C6)-alkyl, Aryl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkoxycarbonyl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkoxycarbonyl-(Ci-C6)-alkyl, Heteroaryl-(Ci-C6)- alkoxycarbonyl-(Ci-C6)-alkyl, Aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylaminocarbonyl- (Ci-C6)-alkyl, (C3-C6)-Cycloalkylaminocarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)- alkylaminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylamino, Arylamino, (C3-C6)-Cycloalkylamino, Aryl-(Ci-C6)-alkylamino, Heteroaryl-(Ci-C6)-alkylamino, Heteroarylamino, Heterocyclylamino, Aryloxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, Heteroaryloxy-(Ci-C6)-alkyl, (C2-C6)- Alkenyl, (C2-C6)-Alkinyl, (C2-C6)-Alkenylamino, (C2-C6)-Alkinylamino, Bis-[(Ci-C6)- alkenyl]amino, Aryloxy, Bis-[(Ci-C6)-Alkyl]amino, Aryl-(C2-C6)-alkenyl, Heteroaryl-(C2-C6)- alkenyl, Heterocyclyl-(C2-C6)-alkenyl, Aryloxycarbonyl-(Ci-C6)-alkyl, Heteroaryloxycarbonyl- (Ci-C6)-alkyl, Bis[(Ci-C6)-alkyl]aminocarbonyl-(Ci-C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, Cyano-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkoxy-(Ci-C6)-alkyl, (Ci-C6)- Alkylsulfonylamino-(Ci-C6)-alkyl, (C3-C6)-Cycloalkylsulfonylamino-(Ci-C6)-alkyl, (C 1 -C 6) -alkyl, heteroaryl- (C 1 -C 6) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkyl ) -alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 3 -C 6) -cycloalkoxycarbonyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) ) -alkyl, aminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkylaminocarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkylaminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylamino, arylamino, (C 3 -C 6 ) -cycloalkylamino, aryl- (C 1 -C 6 ) -alkylamino, heteroaryl- (C 1 -C 4) -alkylamino, C 6 ) -alkylamino, heteroarylamino, heterocyclylamino, aryloxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, heteroaryloxy- (C 1 -C 6 ) -alkyl, ( C 2 -C 6) - alkenyl, (C 2 -C 6) -alkynyl, (C2-C6) -alkenylamino, (C2-C6) alkynylamino, bis - [(Ci-C 6) - alkenyl] amino, Aryloxy, bis - [(C 1 -C 6) alkyl] amino, aryl- (C 2 -C 6) alkenyl, heteroaryl- (C 2 -C 6) alkenyl, heterocyclyl- (C 2 -C 6) alkenyl, aryloxycarbonyl- (Ci -C 6) -alkyl, heteroaryloxycarbonyl- (C 1 -C 6 ) -alkyl, bis [(C 1 -C 6 ) -alkyl] aminocarbonyl- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkylthio (C 1 -C 4 ) -alkyl C 6 ) -alkyl, cyano- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) alkyl, (C 1 -C 6 ) -alkylsulfonylamino- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkylsulfonylamino- (C 1 -C 6 ) -alkyl,
Arylsulfonylamino-(Ci-C6)-alkyl, Heteroarylsulfonylamino-(Ci-C6)-alkyl,  Arylsulfonylamino (C 1 -C 6) -alkyl, heteroarylsulfonylamino (C 1 -C 6) -alkyl,
Heterocyclylsulfonylamino-(Ci-C6)-alkyl, Bis-[(Ci-C6)-alkyl]aminosulfonyl-(Ci-C6)-alkyl steht, und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-C6)-Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)-Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, (C i-C6)- Alkoxy-(C i-C6)-alkyl, (C i-C6)-Haloalkoxy-(C i -C6)-alkyl, (Ci-C6)-Alkylthio-(Ci-C6)-alkyl, (Ci-C6)-Haloalkylthio-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)- haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl- (Ci-C6)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C6)-alkyl, COR12, S02R13, (Ci-C6)-Alkyl-HN02S-, (C3-C6)-Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl, Aryl-(Ci-C6)-Alkoxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)-Alkoxycarbonyl, Heteroaryl-(C i-Ce)-Alkoxycarbonyl, (C2-C6)-Alkenyloxycarbonyl, (C2-C6)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C6)-alkyl stehen, für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (C1-C7)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C7)-Cycloalkyl, (C3-C7)- Halocycloalkyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)-alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl-(Ci-C6)- alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C8)-Cycloalkenyl-(Ci-C6)-alkyl, (Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, (C2-C6)-Alkenyloxycarbonyl-(Ci-C6)-alkyl, Aryl-(Ci-C6)- Alkoxycarbonyl-(Ci-C6)-alkyl, Hydroxycarbonyl-(Ci-C6)-alkyl, Heterocyclyl, Heterocyclyl- (Ci-C6)-alkyl steht für Wasserstoff, (Ci-C6)-Alkyl, (C2-C6)-Alkenyl, (C2-C6)-Alkinyl, (Ci-C6)-Cyanoalkyl, (Ci-Cio)- Haloalkyl, (C2-C6)-Haloalkenyl, (C2-C6)-Haloalkinyl, (C3-C8)-Cycloalkyl, (C3-C8)- Halocycloalkyl, (C4-C8)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C6)-Alkoxy-(Ci-C6)- alkyl, (Ci-C6)-Alkoxy-(Ci-C6)-haloalkyl, Aryl, Aryl-(Ci-C6)-alkyl, Heteroaryl, Heteroaryl- (Ci-C6)-alkyl, Heterocyclyl-(Ci-C6)-alkyl, (C3-C6)-Cycloalkyl-(Ci-C6)-alkyl, (C4-C8)- Cycloalkenyl-(Ci-C6)-alkyl, NR10RU steht. Heterocyclylsulfonylamino (C 1 -C 6) -alkyl, bis - [(C 1 -C 6) -alkyl] aminosulfonyl- (C 1 -C 6) -alkyl, and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) -haloalkyl, (C 2 -C 6) haloalkenyl , (C 2 -C 6 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -halocycloalkenyl , (C iC 6) - alkoxy (C iC 6) alkyl, (C iC 6) haloalkoxy (C i -C 6) alkyl, (Ci-C 6) alkylthio (Ci-C 6) -alkyl, (C 1 -C 6 ) -haloalkylthio (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl , Heteroaryl, heteroaryl- (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl- (C 1 -C 6 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 6 ) -alkyl, COR 12 , S0 2 R 13, (Ci-C 6) alkyl-S- HN0 2, (C3-C6) -cycloalkyl-HN0 2 S-, heterocyclyl, (Ci-C 6) alkoxycarbonyl (Ci-C 6 ) -alkyl, (C 1 -C 6 ) -alkoxycarbonyl, aryl- (C 1 -C 6 ) -alkoxycarbonyl- (C 1 -C 6 ) -alkyl, aryl- (C 1 -C 6 ) -alkoxycarbon yl, heteroaryl- (C 1 -C 6) -alkoxycarbonyl, (C 2 -C 6) -alkenyloxycarbonyl, (C 2 -C 6) -alkynyloxycarbonyl, heterocyclyl- (C 1 -C 6) -alkyl, for hydrogen, (C 1 -C 6 ) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (C1-C7) - haloalkyl, (C 2 -C 6) haloalkenyl , (C 2 -C 6 ) -haloalkynyl, (C 3 -C 7 ) -cycloalkyl, (C 3 -C 7 ) -halocycloalkyl, (C 4 -C 7 ) -cycloalkenyl, (C 4 -C 7 ) -halocycloalkenyl, ( C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -alkyl, (C 1 -C 6 ) -alkoxy- (C 1 -C 6 ) -haloalkyl, aryl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl, heteroaryl (Ci-C 6) - alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C4-C8) cycloalkenyl (Ci-C 6) alkyl, (Ci-C 6 ) - alkoxycarbonyl- (C 1 -C 6) -alkyl, (C 2 -C 6) -alkenyloxycarbonyl- (C 1 -C 6) -alkyl, aryl- (C 1 -C 6) -alkoxycarbonyl- (C 1 -C 6) -alkyl, hydroxycarbonyl- ( C 1 -C 6 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 6 ) -alkyl is hydrogen, (Ci-C 6) -alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) -alkynyl, (Ci-C 6) cyanoalkyl, (Ci-Cio) - haloalkyl, ( C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -haloalkynyl, (C 3 -C 8 ) -cycloalkyl, (C 3 -C 8 ) -halocycloalkyl, (C 4 -C 8 ) -cycloalkenyl, (C 4 -C 6 ) -haloalkynyl, Cio) -halocycloalkenyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -alkyl, (C 1 -C 6) -alkoxy- (C 1 -C 6) -haloalkyl, aryl, aryl- (C 1 -C 6) -alkyl, heteroaryl , heteroaryl (Ci-C 6) alkyl, heterocyclyl (Ci-C 6) alkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (C 4 -C 8) - cycloalkenyl - (Ci-C 6 ) -alkyl, NR 10 R U.
Verwendung gemäß Anspruch 1, wobei in Formel (I) Use according to claim 1, wherein in formula (I)
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der nachfolgenden Definition hat, für Cyano, Fluor, Chlor, Brom, Iod, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1 -Methyl- prop-l -yl, 2-Methylprop-l -yl, 1 , 1 -Dimethyleth-l -yl, n-Pentyl, Methoxy, Ethoxy, n-Propyloxy, Trifluormethyl, Difluormethyl, Pentafluorethyl, Heptafluor-n-propyl, Heptafluor-iso-propyl, Trifluormethoxy, Difluormethoxy, Aminocarbonyl, Aminothiocarbonyl steht, für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, Hydroxy, Methylamino, Ethylamino, iso-Propylamino, n-Propylamino, Dimethylamino, Diethylamino, Cyclopropylamino, A 1 , A 2 , A 3 and A 4 are the same or different and are independently N (nitrogen) or the group CR 1 and wherein R 1 in the group CR 1 each have the same or different meanings as defined below, for Cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1, 1-dimethylethyl l -yl, n-pentyl, methoxy, ethoxy, n-propyloxy, trifluoromethyl, difluoromethyl, pentafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, trifluoromethoxy, difluoromethoxy, aminocarbonyl, aminothiocarbonyl, for hydrogen, fluorine, chlorine, Bromine, iodine, cyano, nitro, hydroxy, methylamino, ethylamino, iso-propylamino, n-propylamino, dimethylamino, diethylamino, cyclopropylamino,
Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Methoxycarbonylmethylamino, Methoxycarbonylethylamino, Ethoxycarbonylmethylamino, Ethoxycarbonylethylamino, Methoxycarbonylamino, Ethoxycarbonylamino, tert-Butyloxycarbonylamino, Phenylamino, N- Piperidinyl, N-Pyrrolidinyl, N-Morpholinyl, Methylaminocarbonylamino, Cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino, phenylamino, N-piperidinyl, N-pyrrolidinyl, N-morpholinyl, methylaminocarbonylamino,
Ethylaminocarbonylamino, n-Propylaminocarbonylamino, iso-propylaminocarbonylamino, Benzylaminocarbonylamino, Phenylaminocarbonylamino, p-Cl-Phenylaminocarbonylamino, m- Cl-Phenylaminocarbonylamino, o-Cl-Phenylaminocarbonylamino, Ethylaminocarbonylamino, n-propylaminocarbonylamino, iso -propylaminocarbonylamino, benzylaminocarbonylamino, phenylaminocarbonylamino, p-Cl-phenylaminocarbonylamino, m-Cl-phenylaminocarbonylamino, o-Cl-phenylaminocarbonylamino,
Cyclopropylaminocarbonylamino, Cyclobutylaminocarbonylamino, Cyclopropylaminocarbonylamino, cyclobutylaminocarbonylamino,
Cyclopentylaminocarbonylamino, Cyclohexylaminocarbonylamino, Cyclopentylaminocarbonylamino, cyclohexylaminocarbonylamino,
Dimethylaminocarbonylamino, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n-Butyloxy, tert- Butyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, tert-Butyloxycarbonyloxy,  Dimethylaminocarbonylamino, methoxy, ethoxy, n-propyloxy, isopropoxy, n-butyloxy, tert-butyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy,
Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n-Propylaminocarbonyloxy, iso- propylaminocarbonyloxy, Benzylaminocarbonyloxy, Phenylaminocarbonyloxy, Methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy,
Cyclopropylammocarbonyloxy, Cyclobutylammocarbonyloxy, Cyclopentylammocarbonyloxy, Cyclohexylaminocarbonyloxy, Dimethylaminocarbonyloxy, Phenyloxy, p-Cl-Phenyloxy, o-Cl- Phenyloxy, m-Cl-Phenyloxy, m-Trifluormethylphenyloxy, p-Trifluormethylphenyloxy, Trifluormethyloxy, Difluormethyloxy, 2,2-Difluorethyloxy, 2,2,2-Trifluorethyloxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Phenylthio, p-Cl-Phenylthio, m-Cl-Phenylthio, o-Cl- Phenylthio, Pyridin-2-ylthio, Pyridin-3-ylthio, Benzylthio, Trifluormethylthio, Cyclopropylammocarbonyloxy, cyclobutylammocarbonyloxy, cyclopentylammocarbonyloxy, cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, phenyloxy, p-C1-phenyloxy, o-Cl-phenyloxy, m-Cl-phenyloxy, m-trifluoromethylphenyloxy, p-trifluoromethylphenyloxy, Trifluoromethyloxy, difluoromethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, isopropylthio, phenylthio, p-Cl-phenylthio, m-Cl-phenylthio, o-Cl-phenylthio, Pyridin-2-ylthio, pyridin-3-ylthio, benzylthio, trifluoromethylthio,
Pentafluorethylthio, Cyclopropylthio, Cyclobutylthio, Cyclopentylthio, Cyclohexylthio, Methylsulfinyl, Ethylsulfinyl, n-Propylsulfinyl, iso-Propylsulfinyl, n-Butylsulfmyl, tert- Butylsulfinyl, Phenylsulfinyl, Benzylsulfinyl, Pyridin-2-ylsulfinyl, Methylsulfonyl, Pentafluoroethylthio, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, iso-propylsulfinyl, n-butylsulfmyl, tert-butylsulfinyl, phenylsulfinyl, benzylsulfinyl, pyridin-2-ylsulfinyl, methylsulfonyl,
Ethylsulfonyl, n-Propylsulfonyl, iso-Propylsulfonyl, n-Butylsulfonyl, tert-Butylsulfonyl, Phenylsulfonyl, Benzylsulfonyl, Pyridin-2-ylsulfonyl, 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-Di-methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2-Ethylbutyl, 1,1,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1- Ethyl-1 -methylpropyl, 1 -Ethyl-2-methylpropyl, Thiocyanato, Isothiocyanato, Ethenyl, 1- Propenyl, 2-Propenyl, 1 -Methyl- ethenyl, 1-Butenyl, 2-Butenyl, 3-Butenyl, 1 -Methyl- 1-propenyl, 2-Methyl- 1-propenyl, 1 -Methyl-2-propenyl, 2-Methyl-2-propenyl, 1-Pentenyl, 2-Pentenyl, 3- Pentenyl, 4-Pentenyl, 1 -Methyl- 1-butenyl, 2-Methyl- 1-butenyl, 3 -Methyl- 1-butenyl, 1-Methyl- 2-butenyl, 2-Methyl-2-butenyl, 3-Methyl-2-butenyl, l-Methyl-3-butenyl, 2-Methyl-3-butenyl, 3- Methyl-3-butenyl, 1 , 1 -Dimethyl-2-propenyl, 1 ,2-Dimethyl- 1-propenyl, 1 ,2-Dimethyl-2- propenyl, 1-Ethyl-l -propenyl, l-Ethyl-2-propenyl, Ethinyl, 1-Propinyl, 2-Propinyl, 1-Butinyl, 2- Butinyl, 3-Butinyl, 1 -Methyl-2-propinyl, 1-Pentinyl, 2-Pentinyl, 3-Pentinyl, 4-Pentinyl, 1- Methyl-2-butinyl, l-Methyl-3-butinyl, 2-Methyl-3-butinyl, 3 -Methyl- 1-butinyl, l,l-Dimethyl-2- propinyl, 1 -Ethyl-2-propinyl, 1-Hexinyl, 2-Hexinyl, 3-Hexinyl, 3,3-Difluorcyclobut-l-yl, 3- Fluorcyclobut-l-yl, 1-Fluorcyclobut-l-yl, 2,2-Difluorcycloprop-l-yl, 1-Fluorcycloprop-l-yl, 2- Fluorcycloprop-l-yl, 4-Fluorcyclohexyl, 4,4-Difluorcyclohexyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Methylcycloprop-l-yl, 2-Methylcycloprop-l-yl, 2,2- Dimethylcycloprop-l-yl, 2,3-Dimethylcyclopropyl, 1 -Cyanopropyl, 2-Cyanopropyl, 1- Methylcyclobutyl, 2-Methylcyclobutyl, 3-Methylcyclobutyl, 3,3-Dimethylcyclobutyl, 1- Cyanocyclobutyl, 2-Cyanocyclobutyl, 3-Cyanocyclobutyl, 1 -Allylcyclopropyl, 1- Vinylcyclobutyl, 1 -Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2- Methylcyclohexyl, 3 -Methylcyclohexyl, 1 -Methoxycyclohexyl, 2-Methoxycyclohexyl, 3- Methoxycyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Ethylsulfonyl, n-propylsulfonyl, iso -propylsulfonyl, n-butylsulfonyl, tert-butylsulfonyl, phenylsulfonyl, benzylsulfonyl, pyridin-2-ylsulfonyl, 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-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, thiocyanato, isothiocyanato, ethenyl, 1-propenyl, 2-propenyl, 1-methyl-ethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-Me ethyl-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, Ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-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, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-yl, 1-fluorocycloprop-1-yl yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcyclopropyl 1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dim ethylcyclobutyl, 1-cyanocyclobutyl, 2-cyanocyclobutyl, 3-cyanocyclobutyl, 1-allylcyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1,1,2,2-Tetrafluorethyl, Heptafluor-n- propyl, Heptafluor-iso-propyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl,
Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, Fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl,
Chlormethyl, Brommethyl, Fluormethyl, 3,3,3-Trifluor-n-propyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propyloxycarbonyl, n-Propyloxycarbonyl, n-Butyloxycarbonyl, tert- Butyloxycarbonyl, Benzyloxycarbonyl, Allyloxycarbonyl, Methylaminocarbonyl, Chloromethyl, bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl, Ethoxycarbonyl, iso-propyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl,
Ethylaminocarbonyl, n-Propylaminocarbonyl, iso-Propylaminocarbonyl, Benzylaminocarbonyl, Phenylaminocarbonyl, Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Ethylaminocarbonyl, n-propylaminocarbonyl, iso -propylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,
Cyclopentylaminocarbonyl, Cyclohexylaminocarbonyl, Dimethylaminocarbonyl, Cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl,
Diethylaminocarbonyl, Allylaminocarbonyl, Pentafluorthio, Methoxydifluormethyl, Diethylaminocarbonyl, allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl,
Ethoxydifluormethyl, n-Propyloxydifluormethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethoxy-n-propyl, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, Ethoxyethyl, Methoxyethyl, n-Propyloxyethyl, Methoxy-n-propyl, Ethoxy-n-propyl, 1-Methoxyeth-l-yl, 1- Methoxyprop-l-yl, 1-Ethoxyeth-l-yl, 2-Methoxyprop-2-yl, 2-Ethoxyprop-2-yl, Ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-l yl, 1-methoxyprop-1-yl, 1-ethoxyeth-1-yl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl,
Methylthiomethyl, Methylthioethyl, Methylthio-n-propyl, Ethylthiomethyl, Methylthiomethyl, methylthioethyl, methylthio-n-propyl, ethylthiomethyl,
Trifluormethylthiomethyl, Petntafluorethylthiomethyl, Trifluormethylthioethyl, Trifluoromethylthiomethyl, petlafluoroethylthiomethyl, trifluoromethylthioethyl,
Trifluormethylthio-n-propyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, n- Butylcarbonyl, tert-Butylcarbonyl, Phenylcarbonyl, o-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, p-Cl-Phenylcarbonyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n-Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, tert- Butyloxycarbonylethyl, Hydroxycarbonylmethyl, Hydroxycarbonylethyl, Hydroxycarbonyl, Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, n-Propylaminocarbonylmethyl, iso- Propylaminocarbonylmethyl, Benzylaminocarbonylmethyl, Phenylaminocarbonylmethyl, Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl, Trifluoromethylthio-n-propyl, methylcarbonyl, ethylcarbonyl, iso-propylcarbonyl, n-butylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, o-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, p-Cl-phenylcarbonyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, tert-butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n -propylaminocarbonylmethyl, iso -propylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl,
Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl, Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl,
Dimethylaminocarbonylmethyl, Diethylaminocarbonylmethyl, Allylaminocarbonylmethyl, Methylaminomethyl, Dimethylaminomethyl, Diethylaminomethyl, Ethylaminomethyl, iso- Propylaminomethyl, n-Propylaminomethyl, n-Butylaminomethyl, Methylaminoethyl, Dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl, allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl, diethylaminomethyl, ethylaminomethyl, iso-propylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl,
Dimethylaminoethyl, Diethylaminoethyl, N-Pyrrolidinylmethyl, N-Piperidinylmethyl, Dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, N-piperidinylmethyl,
Hydroxyimino, Methoxyimino, Ethoxyimino, n-Propyloxyimino, n-Butyloxyimino, iso- Propyloxyimino, tert-Butyloxyimino, Cyclopropylmethoxyimino, Hydroxyimino, methoxyimino, ethoxyimino, n-propyloxyimino, n-butyloxyimino, iso-propyloxyimino, tert-butyloxyimino, cyclopropylmethoxyimino,
Cyclobutylmethoxyimino,Cyclopentylmethoxyimino, Cyclohexylmethoxyimino, Cyclobutylmethoxyimino, cyclopentylmethoxyimino, cyclohexylmethoxyimino,
Benzyloxyimino, Phenyloxyimino, Allyloxyimino, p-Cl-Phenylmethyloxyimino, Phenylethinyl, p-Cl-Phenylethinyl, m-Cl-Phenylethinyl, o-Cl-Phenylethinyl, p-F-Phenylethinyl, m-F- Phenylethinyl, o-F-Phenylethinyl, Pyridin-2-ylethinyl, Pyridin-3-ylethinyl, Thiophen-2- ylethinyl, Trimethylsilylethinyl, Triethylsilylethinyl, Tri(iso-propyl)silylethinyl, Benzyloxyimino, phenyloxyimino, allyloxyimino, p-Cl-phenylmethyloxyimino, phenylethynyl, p-Cl-phenylethynyl, m-Cl-phenylethynyl, o-Cl-phenylethynyl, pF-phenylethynyl, mF-phenylethynyl, oF-phenylethynyl, pyridin-2-ylethynyl, Pyridin-3-ylethynyl, thiophen-2-ylethynyl, trimethylsilylethynyl, triethylsilylethynyl, tri (iso-propyl) silylethynyl,
Cyclopropylethinyl, Cyclobutylethinyl, Cyclopentylethinyl, Cyclohexylethinyl, Phenyl, Benzyl, p-Cl-Phenyl, m-Cl-Phenyl, o-Cl-Phenyl, p-F-Phenyl, m-F-Phenyl, o-F-Phenyl, p- Trifluormethylphenyl, m-Trifluormethylphenyl, o-Trifluormethylphenyl, p-Methylphenyl, m- Methylphenyl, o-Methylphenyl, p-Methoxyphenyl, m-Methoxyphenyl, o-Methoxyphenyl, p-Cl- Phenylmethyl, m-Cl-Phenylmethyl, o-Cl-Phenylmethyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Thiophen-2-yl, Thiophen-3-yl, Furan-2-yl, Furan-3-yl, Pyrimidin-2-yl, Pyrazin-2-yl, Cyclopropylethynyl, cyclobutylethynyl, cyclopentylethynyl, cyclohexylethynyl, phenyl, benzyl, p-Cl-phenyl, m-Cl-phenyl, o-Cl-phenyl, pF-phenyl, mF-phenyl, oF-phenyl, p-trifluoromethylphenyl, m-trifluoromethylphenyl, o-trifluoromethylphenyl, p-methylphenyl, m-methylphenyl, o-methylphenyl, p-methoxyphenyl, m-methoxyphenyl, o-methoxyphenyl, p-Cl-phenylmethyl, m-Cl-phenylmethyl, o-Cl-phenylmethyl, pyridin-2 yl, pyridin-3-yl, pyridin-4-yl, Thiophen-2-yl, thiophen-3-yl, furan-2-yl, furan-3-yl, pyrimidin-2-yl, pyrazine-2-yl,
Methoxymethoxymethyl, Ethoxyethoxymethyl, Methoxyethoxymethyl,  Methoxymethoxymethyl, ethoxyethoxymethyl, methoxyethoxymethyl,
Methylaminosulfonylamino, Dimethylaminosulfonylamino, Ethylaminosulfonylamino, Diethylaminosulfonylamino, iso-Propylaminosulfonylamino, Cyclopropylaminosulfonylamino, Cyclobutylaminosulfonylamino, Cyclopentylaminosulfonylamino,  Methylaminosulfonylamino, dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, iso-propylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino, cyclopentylaminosulfonylamino,
Cyclohexylaminosulfonylamino, steht,  Cyclohexylaminosulfonylamino,
R2 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1 - Methyl-prop-l-yl, 2-Methyl-prop-l-yl, n-Pentyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanomethyl, 2-Cyanoeth-l-yl, 1-Cyano-eth-l-yl, 3-Cyanoprop-l-yl, R 2 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methyl-prop-1-yl, 2-methyl-prop-1-yl, n-pentyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanomethyl, 2-cyanoeth-1-yl, 1-cyano-eth-1-yl, 3-cyanoprop-1-yl,
Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, Cyclopentylmethyl,  Cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl, cyclopentylmethyl,
Cyclohexylmethyl, Methylsulfonyl, Ethylsulfonyl, iso-Propylsulfonyl, n-Propylsulfonyl, n- Butylsulfonyl, 1-Methylprop-l-yl, 2-Methylprop-l -yl, 1,1-Dimethyleth-l-ylsulfonyl,  Cyclohexylmethyl, methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsulfonyl,
Cyclopropylsulfonyl, Cyclobutylsulfonyl, Cyclopentylsulfonyl, Cyclohexylsulfonyl,  Cyclopropylsulfonyl, cyclobutylsulfonyl, cyclopentylsulfonyl, cyclohexylsulfonyl,
Phenylsulfonyl, p-Cl-Phenylsulfonyl, m-Cl-Phenylsulfonyl, p-Cl-Phenylsulfonyl, p-F- Phenylsulfonyl, m-F-Phenylsulfonyl, p-F-Phenylsulfonyl, p-Cyano-Phenylsulfonyl, m-Cyano- Phenylsulfonyl, p-Cyano-Phenylsulfonyl, p-Methylphenylsulfonyl, m-Methylphenylsulfonyl, p- Methylphenylsulfonyl, p-Trifluormethylphenylsulfonyl, m-Trifluormethylphenylsulfonyl, p- Trifluormethylphenylsulfonyl, Benzylsulfonyl, p-Cl-Phenylmethylsulfonyl, m-Cl- Phenylmethylsulfonyl, p-Cl-Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, m-F- Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, m-Cyano- Phenylmethylsulfonyl, p-Cyano-Phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, m- Methyl-phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, m-Trifluormethyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, tert.-Butylcarbonyl, Phenylcarbonyl, p-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, o-Cl-Phenylcarbonyl, p-F- Phenylcarbonyl, m-F-Phenylcarbonyl, o-F-Phenylcarbonyl, Pyridin-2-ylcarbonyl, Pyridin-3- ylcarbonyl, Pyridin-4-ylcarbonyl, 4-Trifluormethyl-pyridin-3-ylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexylcarbonyl, Methoxycarbonyl,  Phenylsulfonyl, p-Cl-phenylsulfonyl, m-Cl-phenylsulfonyl, p-Cl-phenylsulfonyl, pF-phenylsulfonyl, mF-phenylsulfonyl, pF-phenylsulfonyl, p-cyano-phenylsulfonyl, m-cyano-phenylsulfonyl, p-cyano-phenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, p-methylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, m-trifluoromethylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, benzylsulfonyl, p-Cl-phenylmethylsulfonyl, m-Cl-phenylmethylsulfonyl, p-Cl-phenylmethylsulfonyl, pF-phenylmethylsulfonyl, mF- Phenylmethylsulfonyl, p-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, m-cyano-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, p-methylphenylmethylsulfonyl, m-methylphenylmethylsulfonyl, p-methylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, m- Trifluoromethylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, methylcarbonyl, ethylcarbonyl, iso -propylcarbonyl, tert -butylcarbonyl, phenylcarbonyl, p-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, o-Cl-P henylcarbonyl, pF-phenylcarbonyl, mF-phenylcarbonyl, oF-phenylcarbonyl, pyridin-2-ylcarbonyl, pyridin-3-ylcarbonyl, pyridin-4-ylcarbonyl, 4-trifluoromethylpyridin-3-ylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, methoxycarbonyl,
Ethoxycarbonyl, tert-Butyloxycarbonyl, Benzyloxycarbonyl, Trifluormethylcarbonyl,  Ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, trifluoromethylcarbonyl,
Difluormethylcarbonyl, Allyl, Propargyl, 2,2-Difluorethyl, 3,3,3-Trifluorethyl, Methoxymethyl, Methoxyethyl, Methoxy-n-propyl, Ethoxyethyl, Ethoxymethyl, Ethoxy-n-propyl, Amino, Methylaminocarbonyl, Ethylaminocarbonyl, Dimethylaminocarbonyl stehen,  Difluoromethylcarbonyl, allyl, propargyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, methoxymethyl, methoxyethyl, methoxy-n-propyl, ethoxyethyl, ethoxymethyl, ethoxy-n-propyl, amino, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, Fluor, Trifluormethyl, Difluormethyl, Phenyl, p-Cl-Phenyl, m-Cl-Phenyl, o-Cl-Phenyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Methoxymethyl, Ethoxymethyl, Ethoxyethyl, Methoxyethyl, Methylthiomethyl, Ethylthiomethyl, Methylthioethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Trifluormethylthiomethyl, Trifluormethylthioethyl, R 3 , R 4 , R 7 and R 8 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, fluorine, trifluoromethyl, difluoromethyl, phenyl, p-Cl-phenyl, m-Cl-phenyl, Cl-phenyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methoxymethyl, ethoxymethyl, ethoxyethyl, Methoxyethyl, methylthiomethyl, ethylthiomethyl, methylthioethyl, trifluoromethoxymethyl, trifluoromethoxyethyl, trifluoromethylthiomethyl, trifluoromethylthioethyl,
Dimethylaminomethyl, Dimethylaminoethyl, Hydroxycarbonyl, methoxycarbonyl,  Dimethylaminomethyl, dimethylaminoethyl, hydroxycarbonyl, methoxycarbonyl,
Ethoxycarbonyl, ior-Propyloxycarbonyl, n-Propyloxycarbonyl, tert-Butyloxycarbonyl, Allyloxycarbonyl, Benzyloxycarbonyl, Dimethylaminocarbonyl, Aminocarbonyl,  Ethoxycarbonyl, ior-propyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, dimethylaminocarbonyl, aminocarbonyl,
Methylaminocarbonyl, Ethylaminocarbonyl, iso-Propylaminocarbonyl,  Methylaminocarbonyl, ethylaminocarbonyl, iso-propylaminocarbonyl,
Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentylaminocarbonyl, Cyclohexylaminocarbonyl, Hydroxycarbonylmethyl, Methoxycarbonylmethyl,  Cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, hydroxycarbonylmethyl, methoxycarbonylmethyl,
Ethoxycarbonylmethyl, ior-Propyloxycarbonylmethyl, n-Propyloxycarbonylmethyl, tert- Butyloxycarbonylmethyl, Allyloxycarbonylmethyl, Benzyloxycarbonylmethyl,  Ethoxycarbonylmethyl, iorpropyloxycarbonylmethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, allyloxycarbonylmethyl, benzyloxycarbonylmethyl,
Dimethylaminocarbonylmethyl, Aminocarbonylmethyl, Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, iso-Propylaminocarbonylmethyl,  Dimethylaminocarbonylmethyl, aminocarbonylmethyl, methylaminocarbonylmethyl, ethylaminocarbonylmethyl, iso-propylaminocarbonylmethyl,
Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl,  Cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl,
Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht,  Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 4 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 7 and R 8 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R2 und R6 mit den Stickstoffatomen, an die sie gebunden sind, sowie den die Stickstoffatome R 2 and R 6 with the nitrogen atoms to which they are attached, as well as the nitrogen atoms
verbindenden Kohlenstoffatomen einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder carbon atoms a fully saturated or partially saturated, form optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 7 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R3 und R6 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 6 with the nitrogen atoms and carbon atoms to which they are respectively attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R2und R3 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 2 and R 3 with the nitrogen atoms and carbon atoms to which they are each bonded form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring, or
R6und R7 mit den Stickstoffatomen und Kohlenstoffatomen, an die sie jeweils gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 5 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden und R 6 and R 7 with the nitrogen atoms and carbon atoms to which they are each bonded, form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 5 to 10-membered monocyclic or bicyclic ring and
R5 für 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 und 1 -Ethyl-2-methylpropyl. Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2- Trifluorethyl, 3,3,3-Trifluorpropyl, Pentafluorethyl, Heptafluor-n-Propyl, Heptafluor-iso-propyl, Nonafluor-n-butyl, Phenyl, 2-Cyanophenyl, 3-Cyanophenyl, 4-Cyanophenyl, 2-Fluor-Phenyl, 3- Fluor-Phenyl, 4-Fluor-Phenyl, 2,4-Difluor-Phenyl, 2,5-Difluor-Phenyl, 2,6-Difluor-Phenyl, 2,3- Difluor-Phenyl, 3,4-Difluor-Phenyl, 3,5-Difluor-Phenyl, 2,4,5-Trifluor-Phenyl, 3,4,5-Trifluor- Phenyl, 2-Chlor-Phenyl, 3-Chlor-Phenyl, 4-Chlor-Phenyl, 2,4-Dichlor-Phenyl, 2,5-Dichlor- Phenyl, 2,6-Dichlor-Phenyl, 2,3-Dichlor-Phenyl, 3,4-Dichlor-Phenyl, 3,5-Dichlor-Phenyl, 2,4,5- Trichlor-Phenyl, 3,4,5-Trichlor-Phenyl, 2,4,6-Trichlor-Phenyl, 2-Brom-Phenyl, 3-Brom-Phenyl, 4-Brom-Phenyl, 2-Iod-Phenyl, 3-Iod-Phenyl, 4-Iod-Phenyl, 2-Brom-4-Fluor-Phenyl, 2-Brom-4- Chlor-Phenyl, 3-Brom-4-Fluor-Phenyl, 3-Brom-4-Chlor-Phenyl, 3-Brom-5-Fluor-Phenyl, 3- Brom-5-Chlor-Phenyl, 2-Fluor-4-Brom-Phenyl, 2-Chlor-4-Brom-Phenyl, 3-Fluor-4-Brom- Phenyl, 3-Chlor-4-Brom-Phenyl, 2-Chlor-4-Fluor-Phenyl, 3-Chlor-4-Fluor-Phenyl, 2-Fluor-3- Chlor-Phenyl, 2-Fluor-4-Chlor-Phenyl, 2-Fluor-5-Chlor-Phenyl, 3-Fluor-4-Chlor-Phenyl, 3- Fluor-5-Chlor-Phenyl, 2-Fluor-6-Chlor-Phenyl, 2-Methyl-Phenyl, 3-Methyl-Phenyl, 4-Methyl- Phenyl, 2,4-Dimethyl-Phenyl, 2,5-Dimethyl-Phenyl, 2,6-Dimethyl-Phenyl, 2,3-Dimethyl- Phenyl, 3,4-Dimethyl-Phenyl, 3,5-Dimethyl-Phenyl, 2,4,5-Trimethyl-Phenyl, 3,4,5-Trimethyl- Phenyl, 2,4,6-Trimethyl-Phenyl, 2-Methoxy-Phenyl, 3-Methoxy-Phenyl, 4-Methoxy-Phenyl, 2,4-Dimethoxy-Phenyl, 2,5-Dimethoxy-Phenyl, 2,6-Dimethoxy-Phenyl, 2,3-Dimethoxy-Phenyl, 3,4-Dimethoxy-Phenyl, 3,5-Dimethoxy-Phenyl, 2,4,5-Trimethoxy-Phenyl, 3,4,5-Trimethoxy- Phenyl, 2,4,6-Trimethoxy-Phenyl, 2-Trifluormethoxy-Phenyl, 3-Trifluormethoxy-Phenyl, 4- Trifluormethoxy-Phenyl, 2-Difluormethoxy-Phenyl, 3-Difluormethoxy-Phenyl, 4- Difluormethoxy-Phenyl, 2-Trifluormethyl-Phenyl, 3-Trifluormethyl-Phenyl, 4-Trifluormethyl- Phenyl, 2-Difluormethyl-Phenyl, 3-Difluormethyl-Phenyl, 4-Difluormethyl-Phenyl, 3,5- Bis(Trifluormethyl)-Phenyl, 3-Trifluormethyl-5-Fluor-Phenyl, 3-Trifluormethyl-5-Chlor- Phenyl, 3-Methyl-5-Fluor-Phenyl, 3-Methyl-5-Chlor-Phenyl, 3-Methoxy-5-Fluor-Phenyl, 3- Methoxy-5-Chlor-Phenyl, 3-Trifluormethoxy-5-Chlor-Phenyl, 2-Ethoxy-Phenyl, 3-Ethoxy- Phenyl, 4-Ethoxy-Phenyl, 2-Methylthio-Phenyl, 3-Methylthio-Phenyl, 4-Methylthio-Phenyl, 2- Trifluormethylthio-Phenyl, 3-Trifluormethylthio-Phenyl, 4-Trifluormethylthio-Phenyl, 2-Ethyl- Phenyl, 3-Ethyl-Phenyl, 4-Ethyl-Phenyl, 2-Methoxycarbonyl-Phenyl, 3-Methoxycarbonyl- Phenyl, 4-Methoxycarbonyl-Phenyl, 2-Ethoxycarbonyl-Phenyl, 3-Ethoxycarbonyl-Phenyl, 4- Ethoxycarbonyl-Phenyl, 4-(Methylcarbonylamino)phenyl, 4-(iso-Propylcarbonylamino)phenyl, 4-(cyclo-Propylamino)phenyl, Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyridazin- 3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-5-yl, Pyrimidin-4-yl, Pyridazin-3 -ylmethyl, Pyridazin-4-ylmethyl, Pyrimidin-2 -ylmethyl, Pyrimidin-5-ylmethyl, Pyrimidin-4-ylmethyl, Pyrazin-2-ylmethyl, 3-Chlor-Pyrazin-2-yl, 3-Brom-Pyrazin-2-yl, 3-Methoxy-Pyrazin-2-yl, 3- Ethoxy-Pyrazin-2-yl, 3-Trifluormethylpyrazin-2-yl, 3-Cyanopyrazin-2-yl, Naphth-2-yl, Naphth- 1-yl, Chinolin-4-yl, Chinolin-6-yl, Chinolin-8-yl, Chinolin-2-yl, Chinoxalin-2-yl, 2- Naphthylmethyl, 1 -Naphthylmethyl, Chinolin-4-ylmethyl, Chinolin-6-ylmethyl, Chinolin-8- ylmethyl, Chinolin-2-ylmethyl, Chinoxalin-2 -ylmethyl, Pyrazin-2-ylmethyl, 4-Chloropyridin-2- yl, 3-Chloropyridin-4-yl, 2-Chloropyridin-3-yl, 2-Chloropyridin-4-yl, 2-Chlorpyridin-5-yl, 2,6- Dichlorpyridin-4-yl, 3-Chlorpyridin-5-yl, 3,5-Dichlorpyridin-2-yl, 3-Chlor-5- Trifluormethylpyridin-2-yl, (4-Chloropyridin-2-yl)methyl, (3-Chloropyridin-4-yl)methyl, (2- Chloropyridin-3-yl)methyl, (2-Chloropyridin-4-yl)methyl, (2-Chlorpyridin-5-yl)methyl, (2,6- Dichlorpyridin-4-yl)methyl, (3-Chlorpyridin-5-yl)methyl, (3,5-Dichlorpyridin-2-yl)methyl, Thiophen-2-yl, Thiophen-3-yl, 5-Methylthiophen-2-yl, 5-Ethylthiophen-2-yl, 5-Chlorthiophen- 2-yl, 5-Bromthiophen-2-yl, 4-Methylthiophen-2-yl, 3-Methylthiophen-2-yl, 5-Fluorthiophen-3- yl, 3,5-Dimethylthiophen-2-yl, 3-Ethylthiophen-2-yl, 4,5-Dimethylthiophen-2-yl, 3,4- Dimethylthiophen-2-yl, 4-Chlorthiophen-2-yl, Furan-2-yl, 5-Methylfuran-2-yl, 5-Ethylfüran-2- yl, 5-Methoxycarbonylfuran-2-yl, 5-Chlorfuran-2-yl, 5-Bromfuran-2-yl, Thiophan-2-yl, Thiophan-3-yl, Sulfolan-2-yl, Sulfolan-3-yl, Tetrahydrothiopyran-4-yl, Tetrahydropyran-4-yl, Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, 2-Phenyleth-l-yl, l-(4-Methylphenyl)eth-l-yl, 1- (3-Methylphenyl)eth-l-yl, l-(2-Methylphenyl)eth-l-yl, l-(4-Chlorphenyl)eth-l-yl, l-(3- Chlorphenyl)eth-l-yl, l-(2-Chlorphenyl)eth-l-yl, l-(4-Trifluormethylphenyl)eth-l-yl, l-(3- Trifluormethylphenyl)eth- 1 -yl, 1 -(2-Trifluormethylphenyl)eth- 1 -yl, 1 -(4-Fluorphenyl)eth- 1 -yl, l-(3-Fluorphenyl)eth-l-yl, l-(2-Fluorphenyl)eth-l-yl, l-(4-Cyanophenyl)eth-l-yl, l-(3- Cyanophenyl)eth-l-yl, l-(2-Cyanophenyl)eth-l-yl, 2-(3-Fluorphenyl)eth-l-yl, 2-(4- Fluorphenyl)eth-l-yl, 2-(2-Fluorphenyl)eth-l -yl, 2-(2-Chlorphenyl)eth-l-yl, 2-(3- Chlorphenyl)eth-l-yl, 2-(4-Chlorphenyl)eth-l-yl, 2-(2-Bromphenyl)eth-l-yl, 2-(3- Bromphenyl)eth-l-yl, 2-(4-Bromphenyl)eth-l-yl, 2-(2-Cyanophenyl)eth-l-yl, 2-(3- Cyanophenyl)eth-l-yl, 2-(4-Cyanophenyl)eth-l-yl, 2-(2-Trifluormethylphenyl)eth-l-yl, 2-(3- Trifluormethylphenyl)eth- 1 -yl, 2-(4-Trifluormethylphenyl)eth- 1 -yl, 2-(2-Methoxyphenyl)eth- 1 - yl, 2-(3-Methoxyphenyl)eth-l-yl, 2-(4-Methoxyphenyl)eth-l-yl, 2-(4-Methylphenyl)eth-l-yl, 2- (2-Methylphenyl)eth-l-yl, Benzyl, (4-Fluorphenyl)methyl, (3-Fluorphenyl)methyl, (2- Fluorphenyl)methyl, (2,4-Difluorphenyl)methyl, (3,5-Difluorphenyl)methyl, (2,5- Difluorphenyl)methyl, (2,6-Difluorphenyl)methyl, (2,4,5-Trifluorphenyl)methyl, (2,4,6- Trifluorphenyl)methyl, (4-Chlorphenyl)methyl, (3-Chlorphenyl)methyl, (2-Chlorphenyl)methyl, (2,4-Dichlorphenyl)methyl, (3,5-Dichlorphenyl)methyl, (2,5-Dichlorphenyl)methyl, (2,6- Dichlorphenyl)methyl, (2,4,5-Trichlorphenyl)methyl, (2,4,6-Trichlorphenyl)methyl, (4- Bromphenyl)methyl, (3-Bromphenyl)methyl, (2-Bromphenyl)methyl, (4-Iodphenyl)methyl, (3- Iodphenyl)methyl, (2-Iodphenyl)methyl, (3-Chlor-5-Trifluormethyl-pyridin-2-yl)methyl, (2- Brom-4-Fluorphenl)methyl, (2-Brom-4-Chlorphenyl)methyl, (3-Brom-4-Fluorphenyl)methyl, (3-Brom-4-Chlorphenyl)methyl, (3-Brom-5-Fluorphenyl)methyl, (3-Brom-5- Chlorphenyl)methyl, (2-Fluor-4-Bromphenyl)methyl, (2-Chlor-4-Bromphenyl)methyl, (3-Fluor- 4-Bromphenyl)methyl, (3-Chlor-4-Bromphenyl)methyl, (2-Chlor-4-Fluorphenyl)methyl, (3- Chlor-4-Fluorphenyl)methyl, (2-Fluor-3 -Chlorphenyl)methyl, (2-Fluor-4-Chlorphenyl)methyl, (2-Fluor-5-Chlorphenyl)methyl, (3-Fluor-4-Chlorphenyl)methyl, (3-Fluor-5- Chlorphenyl)methyl, (2-Fluor-6-Chlorphenyl)methyl, 2-Phenyleth-l-yl, 3-Trifluormethyl-4- Chlorphenyl, 3-Chlor-4-Trifluormethylphenyl, 2-Chlor-4-Trifluormethylphenyl, 3,5- Dfluorpyridin-2-yl, (3,6-Dichlor-pyridin-2-yl)methyl, (4-Trifluormethylphenyl)methyl, (3- Trifluormethylphenyl)methyl, (2-Trifluormethylphenyl)methyl, (4-Ethylphenyl)methyl, (3- Ethylphenyl)methyl, (2-Ethylphenyl)methyl, (4-Trifluormethoxyphenyl)methyl, (3- Trifluormethoxyphenyl)methyl, (2-Trifluormethoxyphenyl)methyl, (4-Methoxyphenyl)methyl, (3-Methoxyphenyl)methyl, (2-Methoxyphenyl)methyl, (4-Methylphenyl)methyl, (3- Methylphenyl)methyl, (2-Methylphenyl)methyl, (4-Cyanophenyl)methyl, (3- Cyanophenyl)methyl, (2-Cyanophenyl)methyl, (2,4-Diethylphenyl)methyl, (3,5- Diethylphenyl)methyl, (3,4-Dimethylphenyl)methyl, (3,5-Dimethoxyphenyl)methyl, 1- Phenyleth-l-yl, l-(2,4-Dichlorphenyl)eth-l -yl, l,3-Thiazol-2-yl, 4-Methyl-l,3-thiazol-2-yl, 1,3- Thiazol-2-yl, l-Methyl-imidazol-4-yl, 1 -Methyl- imidazol-5-yl, 1 -Ethyl-imidazol-4-yl, 1-Ethyl- imidazol-5-yl, l-iso-Propyl-imidazol-4-yl, l-iso-Propyl-imidazol-5-yl, 4- (Methylcarbonylamino)phenylmethyl, 4-(iso-Propylcarbonylamino)phenylmethyl,4-(cyclo- Propylamino)phenylmethyl, Aminophenyl, Methylaminophenyl, Ethylaminophenyl, 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-ethyl-2-methylpropyl. Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 3,3,3-trifluoropropyl, pentafluoroethyl, heptafluoro-n-propyl, Heptafluoro-isopropyl, nonafluoro-n-butyl, phenyl, 2-cyanophenyl, 3-cyanophenyl, 4-cyanophenyl, 2-fluoro-phenyl, 3-fluoro-phenyl, 4-fluoro-phenyl, 2,4-difluoro- Phenyl, 2,5-difluoro-phenyl, 2,6-difluoro-phenyl, 2,3-difluoro-phenyl, 3,4-difluoro-phenyl, 3,5-difluoro-phenyl, 2,4,5-trifluoro-phenyl Phenyl, 3,4,5-trifluoro-phenyl, 2-chloro-phenyl, 3-chloro-phenyl, 4-chloro-phenyl, 2,4-dichloro-phenyl, 2,5-dichloro-phenyl, 2,6- Dichloro-phenyl, 2,3-dichloro-phenyl, 3,4-dichloro-phenyl, 3,5-dichloro-phenyl, 2,4,5- Trichloro-phenyl, 3,4,5-trichloro-phenyl, 2,4,6-trichloro-phenyl, 2-bromo-phenyl, 3-bromo-phenyl, 4-bromo-phenyl, 2-iodo-phenyl, 3 Iodo-phenyl, 4-iodo-phenyl, 2-bromo-4-fluoro-phenyl, 2-bromo-4-chloro-phenyl, 3-bromo-4-fluoro-phenyl, 3-bromo-4-chloro-phenyl, 3-bromo-5-fluoro-phenyl, 3-bromo-5-chloro-phenyl, 2-fluoro-4-bromo-phenyl, 2-chloro-4-bromo-phenyl, 3-fluoro-4-bromo-phenyl, 3-chloro-4-bromo-phenyl, 2-chloro-4-fluoro-phenyl, 3-chloro-4-fluoro-phenyl, 2-fluoro-3-chloro-phenyl, 2-fluoro-4-chloro-phenyl, 2-fluoro-5-chloro-phenyl, 3-fluoro-4-chloro-phenyl, 3-fluoro-5-chloro-phenyl, 2-fluoro-6-chloro-phenyl, 2-methyl-phenyl, 3-methyl Phenyl, 4-methyl-phenyl, 2,4-dimethyl-phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 2,3-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3, 5-dimethyl-phenyl, 2,4,5-trimethyl-phenyl, 3,4,5-trimethyl-phenyl, 2,4,6-trimethyl-phenyl, 2-methoxy-phenyl, 3-methoxy-phenyl, 4- Methoxy-phenyl, 2,4-dimethoxy-phenyl, 2,5-dimethoxy-phenyl, 2,6-dimethoxy-phenyl, 2,3-dimethoxy-phenyl, 3,4-dimethoxy-phenyl, 3,5-dim ethoxy-phenyl, 2,4,5-trimethoxy-phenyl, 3,4,5-trimethoxy-phenyl, 2,4,6-trimethoxy-phenyl, 2-trifluoromethoxy-phenyl, 3-trifluoromethoxy-phenyl, 4-trifluoromethoxy Phenyl, 2-difluoromethoxy-phenyl, 3-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl-phenyl, 2-difluoromethyl-phenyl, 3-difluoromethyl-phenyl, 4-difluoromethyl-phenyl, 3,5-bis (trifluoromethyl) -phenyl, 3-trifluoromethyl-5-fluoro-phenyl, 3-trifluoromethyl-5-chloro-phenyl, 3-methyl-5-fluoro-phenyl, 3-methyl 5-chloro-phenyl, 3-methoxy-5-fluoro-phenyl, 3-methoxy-5-chloro-phenyl, 3-trifluoromethoxy-5-chloro-phenyl, 2-ethoxy-phenyl, 3-ethoxy-phenyl, 4 -Ethoxy-phenyl, 2-methylthio-phenyl, 3-methylthio-phenyl, 4-methylthio-phenyl, 2-trifluoromethylthio-phenyl, 3-trifluoromethylthio-phenyl, 4-trifluoromethylthio-phenyl, 2-ethyl-phenyl, 3-ethyl Phenyl, 4-ethyl-phenyl, 2-methoxycarbonyl-phenyl, 3-methoxycarbonyl-phenyl, 4-methoxycarbonyl-phenyl, 2-ethoxycarbonyl-phenyl, 3-ethoxycarbo nyl-phenyl, 4-ethoxycarbonyl-phenyl, 4- (methylcarbonylamino) -phenyl, 4- (iso -propylcarbonylamino) -phenyl, 4- (cyclopropylamino) -phenyl, pyridin-2-yl, pyridin-3-yl, pyridine-4 -yl, pyrazine-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidin-4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl , Pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazino-2-ylmethyl, 3-chloro-pyrazino-2-yl, 3-bromo-pyrazino-2-yl, 3-methoxy-pyrazine -2-yl, 3-ethoxy-pyrazino-2-yl, 3-trifluoromethylpyrazino-2-yl, 3-cyanopyrazino-2-yl, naphth-2-yl, naphth-1-yl, quinolin-4-yl, quinoline 6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinolin-4-ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinoline -2-ylmethyl, quinoxaline-2-ylmethyl, pyrazine-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2-chloropyridin-3-yl, 2-chloropyridin-4-yl, 2 -Chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl, 3-C chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl) methyl, (3-chloropyridin-4-yl) methyl, (2-chloropyridin-3-yl) methyl, (2-chloropyridine-4-yl) yl) methyl, (2-chloropyridin-5-yl) methyl, (2,6-dichloropyridin-4-yl) methyl, (3-chloropyridin-5-yl) methyl, (3,5-dichloropyridin-2-yl) methyl, Thiophen-2-yl, thiophen-3-yl, 5-methylthiophene-2-yl, 5-ethylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 4-methylthiophene-2 yl, 3-methylthiophene-2-yl, 5-fluorothiophene-3-yl, 3,5-dimethylthiophene-2-yl, 3-ethylthiophene-2-yl, 4,5-dimethylthiophene-2-yl, 3,4- Dimethylthiophen-2-yl, 4-chlorothiophene-2-yl, furan-2-yl, 5-methyl-furan-2-yl, 5-ethyl-furan-2-yl, 5-methoxycarbonyl-furan-2-yl, 5-chlorofuran-2 yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4-yl, tetrahydrofuran-2 yl, tetrahydrofuran-3-yl, 2-phenyleth-1-yl, 1- (4-methylphenyl) eth-1-yl, 1- (3-methylphenyl) eth-1-yl, 1- (2-methylphenyl) eth -l-yl, 1- (4-chlorophenyl) eth-1-yl, 1- (3-chlorophenyl) eth-1-yl, 1- (2-chlorophenyl) eth-1-yl, 1- (4-trifluoromethylphenyl ) eth-1-yl, 1- (3-trifluoromethylphenyl) eth-1-yl, 1- (2-trifluoromethyl-phenyl) -eth-1-yl, 1- (4-fluorophenyl) -eth-1-yl, 1- (3 Fluorophenyl) eth-1-yl, 1- (2-fluorophenyl) eth-1-yl, 1- (4-cyanophenyl) eth-1-yl, 1 (3 Cyanophenyl) eth-1-yl, 1- (2-cyanophenyl) eth-1-yl, 2- (3-fluorophenyl) eth-1-yl, 2- (4-fluorophenyl) eth-1-yl, 2- 2-fluorophenyl) eth-1-yl, 2- (2-chlorophenyl) eth-1-yl, 2- (3-chlorophenyl) eth-1-yl, 2- (4-chlorophenyl) eth-1-yl, 2 - (2-bromophenyl) eth-1-yl, 2- (3-bromophenyl) eth-1-yl, 2- (4-bromophenyl) eth-1-yl, 2- (2-cyanophenyl) eth-1-yl , 2- (3-Cyanophenyl) eth-1-yl, 2- (4-cyanophenyl) eth-1-yl, 2- (2-trifluoromethylphenyl) eth-1-yl, 2- (3-trifluoromethylphenyl) eth-1 -yl, 2- (4-trifluoromethylphenyl) eth-1-yl, 2- (2-methoxyphenyl) eth-1-yl, 2- (3-methoxyphenyl) eth-1-yl, 2- (4-methoxyphenyl) eth -l-yl, 2- (4-methylphenyl) eth-1-yl, 2- (2-methylphenyl) eth-1-yl, benzyl, (4-fluorophenyl) methyl, (3-fluorophenyl) methyl, (2- Fluorophenyl) methyl, (2,4-difluorophenyl) methyl, (3,5-difluorophenyl) methyl, (2,5-difluorophenyl) methyl, (2,6-difluorophenyl) methyl, (2,4,5-trifluorophenyl) methyl , (2,4,6-trifluorophenyl) methyl, (4-chlorophenyl) methyl, (3-chlorophenyl) methyl, (2-chlorophenyl) methyl, (2,4-dichlorophenyl) methyl, (3,5-dichlorophenyl) m ethyl, (2,5-dichlorophenyl) methyl, (2,6-dichlorophenyl) methyl, (2,4,5-trichlorophenyl) methyl, (2,4,6-trichlorophenyl) methyl, (4-bromophenyl) methyl, ( 3-bromophenyl) methyl, (2-bromophenyl) methyl, (4-iodophenyl) methyl, (3-iodophenyl) methyl, (2-iodophenyl) methyl, (3-chloro-5-trifluoromethylpyridin-2-yl) methyl , (2-bromo-4-fluorophenol) methyl, (2-bromo-4-chlorophenyl) methyl, (3-bromo-4-fluorophenyl) methyl, (3-bromo-4-chlorophenyl) methyl, (3-bromo) 5-fluorophenyl) methyl, (3-bromo-5-chlorophenyl) methyl, (2-fluoro-4-bromophenyl) methyl, (2-chloro-4-bromophenyl) methyl, (3-fluoro-4-bromophenyl) methyl, (3-chloro-4-bromophenyl) methyl, (2-chloro-4-fluorophenyl) methyl, (3-chloro-4-fluorophenyl) methyl, (2-fluoro-3-chlorophenyl) methyl, (2-fluoro-4 -Chlorophenyl) methyl, (2-fluoro-5-chlorophenyl) methyl, (3-fluoro-4-chlorophenyl) methyl, (3-fluoro-5-chlorophenyl) methyl, (2-fluoro-6-chlorophenyl) methyl, 2 -Phenyleth-1-yl, 3-trifluoromethyl-4-chlorophenyl, 3-chloro-4-trifluoromethylphenyl, 2-chloro-4-trifluoromethylphenyl, 3,5-dibromopyridin-2-yl, (3,6-di chloro-pyridin-2-yl) methyl, (4-trifluoromethylphenyl) methyl, (3-trifluoromethylphenyl) methyl, (2-trifluoromethylphenyl) methyl, (4-ethylphenyl) methyl, (3-ethylphenyl) methyl, (2-ethylphenyl) methyl, (4-trifluoromethoxyphenyl) methyl, (3 Trifluoromethoxyphenyl) methyl, (2-trifluoromethoxyphenyl) methyl, (4-methoxyphenyl) methyl, (3-methoxyphenyl) methyl, (2-methoxyphenyl) methyl, (4-methylphenyl) methyl, (3-methylphenyl) methyl, (2-methylphenyl ) methyl, (4-cyanophenyl) methyl, (3-cyanophenyl) methyl, (2-cyanophenyl) methyl, (2,4-diethylphenyl) methyl, (3,5-diethylphenyl) methyl, (3,4-dimethylphenyl) methyl , (3,5-Dimethoxyphenyl) methyl, 1-phenyleth-1-yl, 1- (2,4-dichlorophenyl) eth-1-yl, 1,3-thiazol-2-yl, 4-methyl-1,3 -thiazol-2-yl, 1,3-thiazol-2-yl, 1-methyl-imidazol-4-yl, 1-methyl-imidazol-5-yl, 1-ethyl-imidazol-4-yl, 1-ethyl imidazol-5-yl, 1-isopropyl-imidazol-4-yl, 1-iso-propyl-imidazol-5-yl, 4- (methylcarbonylamino) phenylmethyl, 4- (iso -propylcarbonylamino) phenylmethyl, 4- ( cyclopropylamino) phenylmethyl, aminophenyl, methylaminophenyl, ethylaminophenyl,
Dimethylaminophenyl, , 2-(5-Chlor-2-fluorphenyl)eth-l-yl, 2-(4-Chlor-2-fluorphenyl)eth-l -yl, 2-(2-Chlor-4-fluorphenyl)eth- 1 -yl, 2-(2-Chlor-5-fluorphenyl)eth- 1 -yl, 2-(3 -Chlor-2- fluorphenyl)eth-l-yl, 2-(3-Chlor-4-fluorphenyl)eth-l-yl, 2-(3-Chlor-5-fluorphenyl)eth-l-yl, 2- (4-Chlor-3 -fluorphenyl)eth- 1 -yl, 2-(2-Chlor-6-fluorphenyl)eth- 1 -yl, 2-(2,6-Difluorphenyl)eth- 1 - yl, 2-(2,5-Difluorphenyl)eth-l-yl , 2-(2,4-Difluorphenyl)eth-l-yl, 2-(2,6-Dichlorphenyl)eth-l-yl, 2-(2,5-Dichlorphenyl)eth-l-yl , 2-(2,4-Dichlorphenyl)eth-l-yl,  Dimethylaminophenyl, 2- (5-chloro-2-fluorophenyl) eth-1-yl, 2- (4-chloro-2-fluorophenyl) eth-1-yl, 2- (2-chloro-4-fluorophenyl) ethane 1 -yl, 2- (2-chloro-5-fluorophenyl) eth-1-yl, 2- (3-chloro-2-fluorophenyl) eth-1-yl, 2- (3-chloro-4-fluorophenyl) eth -l-yl, 2- (3-chloro-5-fluorophenyl) eth-1-yl, 2- (4-chloro-3-fluorophenyl) eth-1-yl, 2- (2-chloro-6-fluorophenyl) eth-1-yl, 2- (2,6-difluorophenyl) eth-1-yl, 2- (2,5-difluorophenyl) eth-1-yl, 2- (2,4-difluorophenyl) eth-1-yl , 2- (2,6-dichlorophenyl) eth-1-yl, 2- (2,5-dichlorophenyl) eth-1-yl, 2- (2,4-dichlorophenyl) eth-1-yl,
2-(2,2- (2,
3-Dichlorphenyl)eth-l-yl, 2- (3,5-Dichlorphenyl)eth-l-yl, 2-(4-Nitrophenyl)eth-l-yl, 2-(2-Nitrophenyl)eth-l-yl steht. 3-dichlorophenyl) eth-1-yl, 2- (3,5-dichlorophenyl) eth-1-yl, 2- (4-nitrophenyl) eth-1-yl, 2- (2-nitrophenyl) eth-1-yl stands.
4. Behandlung von Pflanzen, umfassend die Applikation einer zur Steigerung der 4. Treatment of plants, comprising the application of a to increase the
Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksamen, nichttoxischen Menge einer oder mehrerer der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3.  Resistance of plants to abiotic stress factors effective, non-toxic amount of one or more of the compounds of formula (I), or in each case their salts according to one of claims 1 to 3.
5. Behandlung gemäß Anspruch 4, wobei die abiotischen Stressbedingungen einer oder mehrerer Bedingungen ausgewählt aus der Gruppe bestehend aus Dürre, Kältestress, Hitzestress, Trockenstress, osmotischem Stress, Staunässe, erhöhtem Bodensalzgehalt, erhöhtem 5. The treatment of claim 4, wherein the abiotic stress conditions of one or more conditions selected from the group consisting of drought, cold stress, heat stress, drought stress, osmotic stress, waterlogging, increased soil salt content, elevated
Ausgesetztsein an Mineralien, Ozonbedingungen, Starklichtbedingungen, beschränkter Verfügbarkeit von Stickstoffnährstoffen und beschränkter Verfügbarkeit von  Exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients and limited availability of
Phosphornährstoffen entsprechen.  Phosphorus nutrients.
6. Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit einem oder mehrer Wirkstoffen ausgewählt aud der Gruppe der Insektizide, Lockstoffe, Akarizide, Fungizide, Nematizide, Herbizide, wachstumsregulatorische Stoffe, Safener, die Pflanzenreife beeinflussende Stoffe und Bakterizide. 6. Use of one or more compounds of the formula (I), or in each case their salts according to one of claims 1 to 3 in the spray application to plants and plant parts in combinations with one or more active ingredients selected from the group of insecticides, attractants, acaricides, fungicides , Nematicides, herbicides, growth regulators, safeners, plant maturity affecting substances and bactericides.
Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 in der Sprühapplikation auf Pflanzen und Pflanzenteilen in Kombinationen mit Düngemitteln. Use of one or more compounds of the formula (I), or in each case their salts according to one of Claims 1 to 3, in the spray application on plants and plant parts in combinations with fertilizers.
8. Verwendung einer oder mehrerer Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 zur Applikation auf gentechnisch veränderten Sorten, deren Saatgut, oder auf Anbauflächen auf denen diese Sorten wachsen. 8. Use of one or more compounds of the formula (I), or in each case their salts according to one of claims 1 to 3 for application to genetically modified varieties, their seed, or on cultivated areas on which these varieties grow.
9. Verwendung von Sprühlösungen, die eine oder mehrere der Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 enthalten, zur Steigerung der Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren. 9. Use of spray solutions containing one or more of the compounds of the formula (I), or in each case their salts according to one of claims 1 to 3, for increasing the resistance of plants to abiotic stress factors.
10. Verfahren zur Erhöhung der Stresstoleranz bei Pflanzen ausgewählt aus der Gruppe der 10. A method for increasing the stress tolerance in plants selected from the group of
Nutzpflanzen, Zierpflanzen, Rasenarten, oder Bäumen, dadurch gekennzeichnet, dass die Applikation einer ausreichenden, nicht-toxischen Menge einer oder mehrere Verbindungen der Formel (I), oder jeweils deren Salze gemäß einem der Ansprüche 1 bis 3 auf die Fläche, wo die entsprechende Wirkung gewünscht wird, umfassend die Anwendung auf die Pflanzen, deren Saatgut oder auf die Fläche auf der die Pflanzen wachsen, erfolgt.  Crops, ornamental plants, lawn species, or trees, characterized in that the application of a sufficient, non-toxic amount of one or more compounds of formula (I), or their salts according to any one of claims 1 to 3 on the area where the corresponding Effect is desired, comprising the application to the plants whose seeds or on the surface on which the plants grow takes place.
11. Verfahren gemäß Anspruch 10, wobei die Widerstandsfähigkeit der so behandelten Pflanzen gegenüber abiotischem Stress gegenüber nicht behandelten Pflanzen unter ansonsten gleichen physiologischen Bedingungen um mindestens 3% erhöht ist. 11. A method according to claim 10, wherein the resistance of the plants so treated to abiotic stress is increased by at least 3% over untreated plants under otherwise identical physiological conditions.
12. Substituierte N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiaminoalkane der allgemeinen Formel (I), oder deren Salze, 12. Substituted N-sulfonyl-N'-aryldiaminoalkanes and N-sulfonyl-N'-heteroaryldiaminoalkanes of the general formula (I), or salts thereof,
Figure imgf000161_0001
worin
Figure imgf000161_0001
wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, X für Cyano steht, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above, X stands for cyano,
R1 für Wasserstoff, Halogen, Cyano, Nitro, NR^R1 OR12, S(0)mR13, Thiocyanato, R 1 is hydrogen, halogen, cyano, nitro, NR 1 R 1 OR 12 , S (0) m R 13 , thiocyanato,
Isothiocyanato, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C i-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-haloalkyl, (Ci-C8)- Haloalkoxy-(Ci-C8)-alkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)- alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, Isothiocyanato, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-Cio) -haloalkyl, (C 2 -C 8) -haloalkenyl, ( C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (Ci-Cio) -halocycloalkenyl, pentafluorothio, (Ci-C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -haloalkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) - alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio ) Cycloalkenyl (C 1 -C 8 ) -alkyl,
Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)- Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkylcarbonyl- (Ci-C8)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl, Aryl-(Ci-C8)-alkinyl, Heteroaryl- (Ci-C8)-alkinyl, Heterocyclyl-(Ci-C8)-alkinyl, Tris-[(Ci-C8)-alkyl]silyl-(C2-C8)-alkinyl, Bis-[(Ci-C8)-alkyl](aryl)silyl-(C2-C8)-alkinyl, Bis-aryl[(Ci-C8)-alkyl]silyl-(C2-C8)- alkinyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkinyl, Aryl-(C2-C8)-alkenyl, Heteroaryl-(C2-C8)- alkenyl, Heterocyclyl-(C2-C8)-alkenyl, (C3-C8)-Cycloalkyl-(C2-C8)-alkenyl, (Ci-C8)- Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylaminosulfonylamino, (C3-C8)- Cycloalkylaminosulfonylamino, Tris-[(Ci-C8)-alkyl]silyl, Bis-[(Ci-C8)-alkyl](aryl)silyl, Bis-aryl[(Ci-C8)-alkyl]silyl steht, Heterocyclyl, heterocyclyl (Ci-C8) alkyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) - alkylthio (Ci-C8) alkyl, ( C 1 -C 8 ) -haloalkylthio (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkylcarbonyl- (C 1 -C 8 ) -alkyl, C (O) OR 12 , C (O) N-R 10 R and the like , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N (O) C- (C 1 -C 8 ) -alkyl, R 10 R u N- (C 1 -C 8 ) -alkyl, aryl- (C 1 -C 8 ) -alkynyl, heteroaryl- (C 1 -C 8 ) -alkynyl, heterocyclyl- (C 1 -C 8 ) -alkynyl, tris [(Ci-C 8) alkyl] silyl (C 2 -C 8) -alkynyl, - bis [(Ci-C 8) alkyl] (aryl) silyl (C 2 -C 8) -alkynyl, bis -aryl [(C 1 -C 8 ) -alkyl] silyl (C 2 -C 8 ) -alkynyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkynyl, aryl- (C 2 -) C 8 ) -alkenyl, heteroaryl- (C 2 -C 8 ) -alkenyl, heterocyclyl- (C 2 -C 8 ) -alkenyl, (C 3 -C 8 ) -cycloalkyl- (C 2 -C 8 ) -alkenyl, (Ci-C8) - alkoxy (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C 8) -Alkylaminosulfonylamino, (C 3 -C 8) - Cycloalkylaminosulfonylamino, tris - [( C 1 -C 8 ) -alkyl] silyl, bis - [(C 1 -C 8 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 8 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C3-C8)-Cycloalkyl, Cyano- (Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (Ci-C8)-Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C8)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C8)- alkylsulfonyl, (Ci-C8)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C8)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C8)-Alkoxycarbonyl, Aryl-(Ci-C8)- alkoxycarbonyl, (Ci-C8)-Haloalkylcarbonyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-Cg)- Haloalkyl, Halo-(C2-C8)-alkinyl, Halo-(C2-C8)-alkenyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, Amino, (Ci-C8)-Alkoxy-(Ci-C8)-alkoxy-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkylsulfonyl, Heterocyclyl-(Ci-C8)-alkylsulfonyl, (C4-C8)-Cycloalkenyl, (C4-C8)-Cycloalkenyl- (Ci-C8)-alkyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, (Ci-Cs)- Alkylaminocarbonyl, (C3-C8)-Cycloalkylaminocarbonyl, Bis-[(Ci-C8)- Alkyljaminocarbonyl stehen, R 2 and R 6 are each independently hydrogen, (Ci-C 8) -alkyl, (C 3 -C 8) cycloalkyl, cyano (Ci-C 8) alkyl, (C 3 -C 8) cycloalkyl (Ci-C 8) alkyl, (Ci-C8) alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 8) cycloalkylsulfonyl, heterocyclylsulfonyl, aryl (Ci-C8) - alkylsulfonyl, (Ci-C 8 ) alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C 3 -C 8) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C8) alkoxycarbonyl, aryl (Ci-C8) - alkoxycarbonyl, (Ci-C 8) haloalkylcarbonyl, ( C 2 -C 8 ) alkenyl, (C 2 -C 8 ) alkynyl, (C 1 -C 8 ) haloalkyl, halo (C 2 -C 8 ) alkynyl, halo (C 2 -C 8 ) alkenyl , (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, amino, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, heteroaryl (Ci-C8) alkylsulfonyl, heterocyclyl (Ci-C8) alkylsulfonyl, (C4-C8) cycloalkenyl, (C 4 -C 8) cycloalkenyl (Ci-C 8) alkyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, (Ci-Cs) - alkylaminocarbonyl, (C 3 -C 8) cycloalkylaminocarbonyl, bis - [(Ci-C 8) - Alk yljaminocarbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, Halogen, (Ci-C8)-Haloalkyl, Aryl, Heteroaryl, (C3-C8)-Cycloalkyl, Heterocyclyl, (Ci-C8)-Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy- (Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, Bis-[(Ci-C8)-Alkyl]amino-(Ci-C8)- alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C8)-alkyl, R10RuN(O)C-(Ci-C8)-alkyl, R10RuN-(Ci-C8)-alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R 3, R 4, R 7 and R 8 independently represent hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halogen, (Ci-C8) haloalkyl, aryl, heteroaryl, (C 3 -C 8) cycloalkyl, heterocyclyl, (Ci-C 8) alkoxy (Ci-C 8) alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (C -C 8 ) -haloalkoxy (Ci-C 8) alkyl, (Ci-C8) -Haloalkylthio- (Ci-C 8) alkyl, - bis [(Ci-C 8) alkyl] amino- (Ci-C 8) - alkyl, C (0) OR 12 , C (O) NR 10 R u , C (0) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 8 ) -alkyl, R 10 R u N (O) C- (C 1 -C 8 ) -alkyl, R 10 R u N- (C 1 -C 8 ) -alkyl, m is 0, 1 or 2, n is 1, 2 or 3,
R3 und R4 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 4 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 7 and R 8 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R5 für Heteroaryl, Heterocyclyl, Aryl-(Ci-C8)-alkyl, Heteroaryl-(Ci-C8)-alkyl, R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 8 ) -alkyl, heteroaryl- (C 1 -C 8 ) -alkyl,
Heterocyclyl-(Ci-C8)-alkyl steht, Heterocyclyl (C 1 -C 8 ) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (Ci-Cs)- Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C i-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C8)-Alkoxy- (Ci-C8)-alkyl, (Ci-C8)-Haloalkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkylthio-(Ci-C8)-alkyl, (Ci-C8)-Haloalkylthio-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl- (Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, COR12, S02R13, (Ci-C8)-Alkyl-HN02S-, (C3-C8)- Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (Ci-C8)- Alkoxycarbonyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)- Alkoxycarbonyl, Heteroaryl-(Ci-C8)-Alkoxycarbonyl, (C2-C8)-Alkenyloxycarbonyl, (C2-C8)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C8)-alkyl stehen, R 10 and R 11 are identical or different and are each independently hydrogen, (C 1 -C 8 ) -alkyl, (C 2 -C 8 ) -alkenyl, (C 2 -C 8 ) -alkynyl, (C 1 -C 8 ) - Cyanoalkyl, (C 1 -C 8 ) -haloalkyl, (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C i -C) cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -haloalkoxy- (C 1 -C 8 ) -alkyl, (Ci-C8) alkylthio (Ci-C8) alkyl, (Ci-C 8) -Haloalkylthio- (Ci-C 8) alkyl, (Ci-C 8) alkoxy (Ci-C 8 ) -haloalkyl, aryl, aryl (Ci-C 8) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C 4 -Cio) cycloalkenyl ( Ci-C 8) alkyl, COR 12, S0 2 R 13, (Ci-C8) alkyl-S- HN0 2, (C 3 -C 8) - cycloalkyl HN0 2 S-, heterocyclyl, (Ci- C8) alkoxycarbonyl (Ci-C 8) alkyl, (Ci-C8) - alkoxycarbonyl, aryl (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C 8) - alkoxycarbonyl, heteroaryl- (Ci-C8) alkoxycarbonyl, (C 2 -C 8) alkenyloxycarbonyl, (C 2 -C 8) -alkynyloxycarbonyl, heterocyclyl (Ci-C 8) -alkyl,
R12 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Cs)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl-(Ci-C8)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C8)-alkyl, (Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, (C2-C8)- Alkenyloxycarbonyl-(Ci-C8)-alkyl, Aryl-(Ci-C8)-Alkoxycarbonyl-(Ci-C8)-alkyl, Hydroxycarbonyl-(Ci-C8)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C8)-alkyl steht und R 12 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -) Cio) -halocycloalkenyl, (C 1 -C 5 ) -alkoxy- (C 1 -C 8 ) -alkyl, (C 1 -C 8 ) -alkoxy- (C 1 -C 8 ) -haloalkyl, aryl, aryl- (C 1 -C 8 ) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, (C 3 -C 8) -cycloalkyl- (Ci-C8) alkyl, (C4-C10) - cycloalkenyl (Ci-C8) - alkyl, (Ci-C8) alkoxycarbonyl (Ci-C 8) alkyl, (C 2 -C 8) - alkenyloxycarbonyl (Ci-C 8) alkyl, aryl (Ci-C8) alkoxycarbonyl (C 1 -C 8 ) -alkyl, hydroxycarbonyl- (C 1 -C 8 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 8 ) -alkyl and
R13 für Wasserstoff, (Ci-C8)-Alkyl, (C2-C8)-Alkenyl, (C2-C8)-Alkinyl, (Ci-C8)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C8)-Haloalkenyl, (C2-C8)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-Cs)- Alkoxy-(Ci-C8)-alkyl, (Ci-C8)-Alkoxy-(Ci-C8)-haloalkyl, Aryl, Aryl-(Ci-C8)-alkyl, Heteroaryl, Heteroaryl-(Ci-C8)-alkyl, Heterocyclyl-(Ci-C8)-alkyl, (C3-C8)-Cycloalkyl- (Ci-C8)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C8)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, (C 2 -C 8) -alkynyl, (Ci-C 8) cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 8 ) -haloalkenyl, (C 2 -C 8 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -Cio) -Halocycloalkenyl, (Ci-Cs) - alkoxy (Ci-C 8 ) -alkyl, (Ci-C 8 ) -Alkoxy- (Ci-C 8 ) -haloalkyl, aryl, aryl- (Ci-C 8 ) alkyl, heteroaryl, heteroaryl (Ci-C 8) alkyl, heterocyclyl (Ci-C8) alkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (C 4 - Cio) -Cycloalkenyl- (Ci-C 8 ) alkyl, NR 10 R U.
13. Substituierte N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiammoalkane der allgemeinen Formel (I), gemäß Anspruch 12 oder deren Salze, worin 13. Substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiammoalkane of the general formula (I), according to claim 12 or salts thereof, wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, NR10RU, OR12, S(0)mR13,R 1 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, NR 10 R U, OR 12, S (0) m R 13,
Thiocyanato, Isothiocyanato, (Ci-Cv)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C10)- Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, Pentafluorthio, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-haloalkyl, (C1-C7)- Haloalkoxy-(Ci-C7)-alkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-Cv)- alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, Thiocyanato, isothiocyanato, (C 1 -C 4 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 10) -haloalkyl, (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) - Halocycloalkyl, (C4-Cio) cycloalkenyl, (C4-Cio) -Halocycloalkenyl, pentafluorosulfanyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, (Ci-C7) haloalkoxy (Ci-C 7 ) -haloalkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, aryl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 4 ) -alkyl, (C 3 -C 4 ) -alkyl, C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 7 ) -alkyl,
Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (C1-C7)- Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkylcarbonyl- (Ci-C7)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C-(Ci-C7)-alkyl, R10RuN(O)C-(Ci-C7)-alkyl, R10RuN-(Ci-C7)-alkyl, Aryl-(Ci-C7)-alkinyl, Heteroaryl- (Ci-C7)-alkinyl, Heterocyclyl-(Ci-C7)-alkinyl, Tris-[(Ci-C7)-alkyl]silyl-(C2-C7)-alkinyl, Bis-[(Ci-C7)-alkyl](aryl)silyl-(C2-C7)-alkinyl, Bis-aryl[(Ci-C7)-alkyl]silyl-(C2-C7)- alkinyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkinyl, Aryl-(C2-C7)-alkenyl, Heteroaryl-(C2-C7)- alkenyl, Heterocyclyl-(C2-C7)-alkenyl, (C3-C7)-Cycloalkyl-(C2-C7)-alkenyl, (C1-C7)- Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylaminosulfonylamino, (C3-C7)- Cycloalkylaminosulfonylamino, Tris-[(Ci-C7)-alkyl]silyl, Bis-[(Ci-C7)-alkyl](aryl)silyl, Bis-aryl[(Ci-C7)-alkyl]silyl steht, Heterocyclyl, heterocyclyl (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (C1-C7) - alkylthio (Ci-C7) alkyl, (C -C 7) -Haloalkylthio- (Ci-C7) alkyl, (Ci-C 7) alkylcarbonyl (Ci-C7) alkyl, C (0) OR 12, C (O) NR 10 R u, C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (C 1 -C 7 ) -alkyl, R 10 R u N (O) C- (Ci-C 7 ) -alkyl, R 10 R u N- (C 1 -C 7 ) -alkyl, aryl- (C 1 -C 7 ) -alkynyl, heteroaryl- (C 1 -C 7 ) -alkynyl, heterocyclyl- (C 1 -C 7 ) -alkynyl, tris- (Ci-C 7) alkyl] silyl (C 2 -C 7) alkynyl, - bis [(Ci-C 7) alkyl] (aryl) silyl (C 2 -C 7) alkynyl, bis- aryl [(Ci-C 7 ) alkyl] silyl (C 2 -C 7 ) alkynyl, (C 3 -C 7 ) cycloalkyl (C 2 -C 7 ) alkynyl, aryl (C 2 -C 7 ) alkenyl, heteroaryl (C 2 -C 7 ) alkenyl, heterocyclyl (C 2 -C 7 ) alkenyl, (C 3 -C 7 ) cycloalkyl (C 2 -C 7 ) alkenyl, ( C1-C7) - alkoxy (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C 7) -Alkylaminosulfonylamino, (C3-C7) - Cycloalkylaminosulfonylamino, tris - [(Ci-C 7 ) -alkyl] silyl, bis - [(C 1 -C 7 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 7 ) -alkyl] silyl,
R2 und R6 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C3-C7)-Cycloalkyl, Cyano- (Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (Ci-C7)-Alkylsulfonyl, Arylsulfonyl, Heteroarylsulfonyl, (C3-C7)-Cycloalkylsulfonyl, Heterocyclylsulfonyl, Aryl-(Ci-C7)- alkylsulfonyl, (Ci-C7)-Alkylcarbonyl, Arylcarbonyl, Heteroarylcarbonyl, (C3-C7)- Cycloalkylcarbonyl, Heterocyclylcarbonyl, (Ci-C7)-Alkoxycarbonyl, Aryl-(Ci-C7)- alkoxycarbonyl, (Ci-C7)-Haloalkylcarbonyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (C1-C7)- Haloalkyl, Halo-(C2-C7)-alkinyl, Halo-(C2-C7)-alkenyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, Amino, (Ci-C7)-Alkoxy-(Ci-C7)-alkoxy-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkylsulfonyl, Heterocyclyl-(Ci-C7)-alkylsulfonyl, (C4-C7)-Cycloalkenyl, (C4-C7)-Cycloalkenyl- (Ci-C7)-alkyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, (C1-C7)- Alkylaminocarbonyl, (C3-C7)-Cycloalkylaminocarbonyl, Bis-[(Ci-C7)- Alkyljaminocarbonyl stehen, R 2 and R 6 are each independently hydrogen, (Ci-C7) alkyl, (C3-C 7) cycloalkyl, cyano (Ci-C7) alkyl, (C 3 -C 7) -cycloalkyl- ( C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkylsulfonyl, arylsulfonyl, heteroarylsulfonyl, (C 3 -C 7 ) -cycloalkylsulfonyl, heterocyclylsulfonyl, aryl- (C 1 -C 7 ) -alkylsulfonyl, (C 1 -C 7 ) - alkylcarbonyl, arylcarbonyl, heteroarylcarbonyl, (C3-C7) - cycloalkylcarbonyl, heterocyclylcarbonyl, (Ci-C 7) alkoxycarbonyl, aryl (Ci-C7) - alkoxycarbonyl, (Ci-C 7) haloalkylcarbonyl, (C 2 - C 7 ) alkenyl, (C 2 -C 7 ) alkynyl, (C 1 -C 7 ) haloalkyl, halo (C 2 -C 7 ) alkynyl, halo (C 2 -C 7 ) alkenyl, (Ci -C 7) alkoxy (Ci-C7) alkyl, amino, (Ci-C7) alkoxy (Ci-C7) alkoxy (Ci-C7) alkyl, heteroaryl (Ci- C 7) alkylsulfonyl, heterocyclyl (Ci-C7) alkylsulphonyl, (C4-C7) cycloalkenyl, (C4-C7) cycloalkenyl (C 7) alkyl, (C 2 -C 7 ) alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, (C1-C7) - alkylaminocarbonyl, (C3-C 7) cycloalkylaminocarbonyl, bis - [(Ci-C 7) - Alkyljaminoca stand by rbonyl,
R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, Fluor, Chlor, Brom, Iod, (Ci-C7)-Haloalkyl, Aryl, Heteroaryl, (C3-C7)-Cycloalkyl, Heterocyclyl, (Ci-C7)-Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)- Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, Bis-[(Ci-C7)- Alkyl]amino-(Ci-C7)-alkyl, C(0)OR12, C(O)NR10Ru, C(0)R12 , -C=NOR12, R120(0)C- (Ci-C7)-alkyl, R10RuN(O)C-(Ci-C7)-alkyl, R10RuN-(Ci-C7)-alkyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht, R 3, R 4, R 7 and R 8 independently represent hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, fluorine, chlorine, bromine, iodine, (Ci-C7) - haloalkyl, aryl, heteroaryl, (C 3 -C 7) cycloalkyl, heterocyclyl, (Ci-C7) alkoxy (Ci-C7) alkyl, (Ci-C7) -alkylthio (Ci-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 ) - Alkyl] amino- (C 1 -C 7 ) -alkyl, C (O) OR 12 , C (O) NR 10 R u , C (O) R 12 , -C = NOR 12 , R 12 0 (0) C- (Ci-C 7 ) alkyl, R 10 R u N (O) C (Ci-C 7 ) alkyl, R 10 R u is N- (Ci-C 7 ) alkyl, m is 0, 1 or 2 stands, n is 1, 2 or 3,
R und R mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R and R with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 7 and R 8 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 3 and R 7 with the carbon atoms to which they are attached form a completely saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring,
R5 für Heteroaryl, Heterocyclyl, Aryl-(Ci-C7)-alkyl, Heteroaryl-(Ci-C7)-alkyl, R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl,
Heterocyclyl-(Ci-C7)-alkyl steht, Heterocyclyl- (C 1 -C 7 ) -alkyl,
R10 und R11 gleich oder verschieden sind und unabhängig voneinander für Wasserstoff, (C1-C7)- Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-Cv)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-C10)- Halocycloalkyl, (C i-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (Ci-C7)-Alkoxy- (Ci-Cv)-alkyl, (Ci-C7)-Haloalkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkylthio-(Ci-C7)-alkyl, (Ci-C7)-Haloalkylthio-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl- (Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, COR12, SO2R13, (Ci-C7)-Alkyl-HN02S-, (C3-C7)- Cycloalkyl-HN02S-, Heterocyclyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, (C1-C7)- Alkoxycarbonyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)- Alkoxycarbonyl, Heteroaryl-(Ci-C7)-Alkoxycarbonyl, (C2-C7)-Alkenyloxycarbonyl, (C2-C7)-Alkinyloxycarbonyl, Heterocyclyl-(Ci-C7)-alkyl stehen R 10 and R 11 are the same or different and are each independently hydrogen, (C 1 -C 7 ) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 4) -cycloalkyl , (Ci-Cio) -haloalkyl, (C 2 -C 7) haloalkenyl, (C2-C7) haloalkynyl, (C 3 -Cio) cycloalkyl, (C3-C10) - halocycloalkyl, (C i-Cio ) Cycloalkenyl, (C 4 -C 10) -halocycloalkenyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 4) -alkyl, (C 1 -C 7 ) -haloalkoxy- (C 1 -C 7 ) -alkyl, C 7 ) -alkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -haloalkylthio (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxy- (C 1 -C 7 ) -haloalkyl , aryl, aryl (Ci-C7) alkyl, heteroaryl, heteroaryl (Ci-C7) alkyl, (C 3 -C 7) cycloalkyl (Ci-C7) alkyl, (C 4 - Cio) cycloalkenyl (C 7) alkyl, COR 12, SO 2 R 13, (Ci-C7) alkyl-S- HN0 2, (C 3 -C 7) - cycloalkyl HN0 2 S-, heterocyclyl , (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, (C 1 -C 7 ) -alkoxycarbonyl, aryl- (C 1 -C 7 ) -alkoxycarbonyl- (C 1 -C 7 ) -alkyl, aryl- Ci-C 7 ) - Alkoxycarbonyl, heteroaryl- (Ci-C7) alkoxycarbonyl, (C 2 -C 7) alkenyloxycarbonyl, (C 2 -C 7) -alkynyloxycarbonyl, are heterocyclyl (Ci-C7) alkyl
R12 für Wasserstoff, (Ci-Cv)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-Cv)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (C1-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl-(Ci-C7)-alkyl, (C4-C10)- Cycloalkenyl-(Ci-C7)-alkyl, (Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, (C2-C7)- Alkenyloxycarbonyl-(Ci-C7)-alkyl, Aryl-(Ci-C7)-Alkoxycarbonyl-(Ci-C7)-alkyl, Hydroxycarbonyl-(Ci-C7)-alkyl, Heterocyclyl, Heterocyclyl-(Ci-C7)-alkyl steht und R 12 is hydrogen, (C 1 -C 4) -alkyl, (C 2 -C 7 ) -alkenyl, (C 2 -C 7 ) -alkynyl, (C 1 -C 4 ) -cyanoalkyl, (C 1 -C 10) -haloalkyl, ( C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) - Halocycloalkenyl, (C 1 -C 7) - alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C7) - alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 4 -C 10) -cycloalkenyl- (C 1 -C 7 ) -alkyl , (Ci-C 7) alkoxycarbonyl (Ci-C7) alkyl, (C2-C7) - alkenyloxycarbonyl (Ci-C7) alkyl, aryl (Ci-C7) alkoxycarbonyl (Ci- C 7 ) -alkyl, hydroxycarbonyl- (C 1 -C 7 ) -alkyl, heterocyclyl, heterocyclyl- (C 1 -C 7 ) -alkyl and
R13 für Wasserstoff, (Ci-C7)-Alkyl, (C2-C7)-Alkenyl, (C2-C7)-Alkinyl, (Ci-C7)-Cyanoalkyl, (Ci-Cio)-Haloalkyl, (C2-C7)-Haloalkenyl, (C2-C7)-Haloalkinyl, (C3-Cio)-Cycloalkyl, (C3-Cio)-Halocycloalkyl, (C4-Cio)-Cycloalkenyl, (C4-Cio)-Halocycloalkenyl, (C1-C7)- Alkoxy-(Ci-C7)-alkyl, (Ci-C7)-Alkoxy-(Ci-C7)-haloalkyl, Aryl, Aryl-(Ci-C7)-alkyl, Heteroaryl, Heteroaryl-(Ci-C7)-alkyl, Heterocyclyl-(Ci-C7)-alkyl, (C3-C7)-Cycloalkyl- (Ci-C7)-alkyl, (C4-Cio)-Cycloalkenyl-(Ci-C7)-alkyl, NR10RU steht. R 13 is hydrogen, (Ci-C7) alkyl, (C 2 -C 7) alkenyl, (C 2 -C 7) alkynyl, (Ci-C 7) cyanoalkyl, (Ci-Cio) -haloalkyl , (C 2 -C 7 ) -haloalkenyl, (C 2 -C 7 ) -haloalkynyl, (C 3 -C 10) -cycloalkyl, (C 3 -C 10) -halocycloalkyl, (C 4 -C 10) -cycloalkenyl, (C 4 -C 10) ) -Halocycloalkenyl, (C 1 -C 7) - alkoxy (Ci-C7) alkyl, (Ci-C7) alkoxy (Ci-C7) haloalkyl, aryl, aryl (Ci-C 7 ) -alkyl, heteroaryl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 7 ) -alkyl, (C 4 -) Cio) -Cycloalkenyl- (Ci-C 7 ) -alkyl, NR 10 R U.
14. Substituierte N-Sulfonyl-N'-aryldiaminoalkane und N-Sulfonyl-N'- heteroaryldiammoalkane der allgemeinen Formel (I), gemäß Anspruch 12 oder deren Salze, worin 14. Substituted N-sulfonyl-N'-aryldiaminoalkane and N-sulfonyl-N'-heteroaryldiammoalkane of the general formula (I), according to claim 12 or salts thereof, wherein
A1, A2, A3 und A4 gleich oder verschieden sind und unabhängig voneinander für N (Stickstoff) oder die Gruppierung C-R1 stehen und wobei R1 in der Gruppierung C-R1 jeweils gleiche oder verschiedene Bedeutungen gemäß der oben stehenden Definition hat, A 1 , A 2 , A 3 and A 4 are identical or different and independently of one another represent N (nitrogen) or the group CR 1 and where R 1 in the grouping CR 1 has the same or different meanings as defined above,
X für Cyano steht, X stands for cyano,
R1 für Wasserstoff, Fluor, Chlor, Brom, Iod, Cyano, Nitro, Hydroxy, Amino, Methylamino, Ethylamino, Dimethylamino, Cyclopropylamino, Cyclobutylamino, Cyclopentylamino, Cyclohexylamino, Methoxycarbonylmethylamino, Methoxycarbonylethylamino, Ethoxycarbonylmethylamino, Ethoxycarbonylethylamino, Methoxycarbonylamino, Ethoxycarbonylamino, tert-Butyloxycarbonylamino, Phenylamino, N-Piperidinyl, N- Pyrrolidinyl, N-Morpholinyl, Methoxy, Ethoxy, n-Propyloxy, iso-Propyloxy, n- Butyloxy, tert-Butyloxy, Methoxycarbonyloxy, Ethoxycarbonyloxy, tert- Butyloxycarbonyloxy, Methylaminocarbonyloxy, Ethylaminocarbonyloxy, n- Propylaminocarbonyloxy, iso-propylaminocarbonyloxy, Benzylaminocarbonyloxy, Phenylaminocarbonyloxy, Cyclopropylaminocarbonyloxy, R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, amino, methylamino, ethylamino, dimethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino, ethoxycarbonylmethylamino, ethoxycarbonylethylamino, methoxycarbonylamino, ethoxycarbonylamino, tert-butyloxycarbonylamino , Phenylamino, N-piperidinyl, N-pyrrolidinyl, N-morpholinyl, methoxy, ethoxy, n-propyloxy, iso-propyloxy, n-butyloxy, tert-butyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, tert-butyloxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-propylaminocarbonyloxy , iso-propylaminocarbonyloxy, benzylaminocarbonyloxy, Phenylaminocarbonyloxy, cyclopropylaminocarbonyloxy,
Cyclobutylaminocarbonyloxy, Cyclopentylaminocarbonyloxy, Cyclobutylaminocarbonyloxy, cyclopentylaminocarbonyloxy,
Cyclohexylaminocarbonyloxy, Dimethylaminocarbonyloxy, Trifluormethyloxy, Difluormethyloxy, 2,2-Difluorethyloxy, 2,2,2-Trifluorethyloxy, Methylthio, Ethylthio, n-Propylthio, iso-Propylthio, Methyl, Ethyl, n-Propyl, 1-Methylethyl, n-Butyl, 1- Methylprop-l-yl, 2-Methylprop-l-yl, 1 , 1 -Dimethyleth- 1 -yl, n-Pentyl, 1 -Methylbutyl, 2- Methylbutyl, 3 -Methylbutyl, 1,1-Dimethylprop-l-yl, 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-Di- methylbutyl, 2,2-Dimethylbutyl, 2,3-Dimethylbutyl, 3,3-Dimethylbutyl, 1 -Ethylbutyl, 2- Ethylbutyl, 1 , 1 ,2-Trimethylpropyl, 1 ,2,2-Trimethylpropyl, 1 -Ethyl- 1 -methylpropyl, 1- Ethyl-2-methylpropyl, 3,3-Difluorcyclobut-l-yl, 3 -Fluorcyclobut- 1-yl, 1 -Fluorcyclobut- 1-yl, 2,2-Difluorcycloprop-l-yl, 1-Fluorcycloprop-l -yl, 2-Fluorcycloprop-l -yl, 4- Fluorcyclohexyl, 4,4-Difluorcyclohexyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, 1-Methylcycloprop-l-yl, 2-Methylcycloprop-l-yl, 2,2-Dimethylcycloprop- 1-yl, 2,3-Dimethylcyclopropyl, 1 -Cyanopropyl, 2-Cyanopropyl, 1 -Methylcyclobutyl, 2- Methylcyclobutyl, 3 -Methylcyclobutyl, 3,3-Dimethylcyclobutyl, 1 -Cyanocyclobutyl, 2- Cyanocyclobutyl, 3 -Cyanocyclobutyl, 1 -Allylcyclopropyl, 1 -Vinylcyclobutyl, 1- Vinylcyclopropyl, 1 -Ethylcyclopropyl, 1 -Methylcyclohexyl, 2-Methylcyclohexyl, 3- Methylcyclohexyl, 1 -Methoxycyclohexyl, 2-Methoxycyclohexyl, 3 -Methoxycyclohexyl, Cyclopropylmethyl, Cyclobutylmethyl, Cyclopentylmethyl, Cyclohexylmethyl, Trifluormethyl, Pentafluorethyl, 1,1,2,2-Tetrafluorethyl, Heptafluor-n-propyl, Cyclohexylaminocarbonyloxy, dimethylaminocarbonyloxy, trifluoromethyloxy, difluoromethyloxy, 2,2-difluoroethyloxy, 2,2,2-trifluoroethyloxy, methylthio, ethylthio, n-propylthio, isopropylthio, methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1, 1-dimethyleth-1-yl, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylprop-1-one yl, 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-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl, 3,3-difluorocyclobut-1-yl, 3-fluorocyclobut-1-yl, 1-fluorocyclobut-1-yl, 2,2-difluorocycloprop-1-one yl, 1-fluorocycloprop-1-yl, 2-fluorocycloprop-1-yl, 4-fluorocyclohexyl, 4,4-difluorocyclohexyl, cyclopropyl, cyclobutyl, cyclopentyl, Cyc lohexyl, 1-methylcycloprop-1-yl, 2-methylcycloprop-1-yl, 2,2-dimethylcycloprop-1-yl, 2,3-dimethylcyclopropyl, 1-cyanopropyl, 2-cyanopropyl, 1-methylcyclobutyl, 2-methylcyclobutyl, 3-methylcyclobutyl, 3,3-dimethylcyclobutyl, 1-cyano-cyclobutyl, 2-cyano-cyclobutyl, 3-cyano-cyclobutyl, 1-allyl-cyclopropyl, 1-vinylcyclobutyl, 1-vinylcyclopropyl, 1-ethylcyclopropyl, 1-methylcyclohexyl, 2-methylcyclohexyl, 3-methylcyclohexyl, 1-methoxycyclohexyl, 2-methoxycyclohexyl, 3-methoxycyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl,
Heptafluor-iso-propyl, Nonafluorbutyl, Chlordifluormethyl, Bromdifluormethyl, Dichlorfluormethyl, Ioddifluormethyl, Bromfluormethyl, 1 -Fluorethyl, 2-Fluorethyl, Fluormethyl, Difluormethyl, 2,2-Difluorethyl, 2,2,2-Trifluorethyl, Difluor-tert.-butyl, 3,3,3-Trifluor-n-propyl, Methoxycarbonyl, Ethoxycarbonyl, iso-Propyloxycarbonyl, n- Propyloxycarbonyl, tert-Butyloxycarbonyl, Benzyloxycarbonyl, Allyloxycarbonyl, Methylaminocarbonyl, Ethylaminocarbonyl, n-Propylaminocarbonyl, iso- Propylaminocarbonyl, Benzylaminocarbonyl, Phenylaminocarbonyl, Heptafluoro-isopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl, fluoromethyl, difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl , 3,3,3-trifluoro-n-propyl, methoxycarbonyl, ethoxycarbonyl, isopropyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, iso-propylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl,
Cyclopropylaminocarbonyl, Cyclobutylaminocarbonyl, Cyclopentylaminocarbonyl, Cyclohexylaminocarbonyl, Dimethylaminocarbonyl, Diethylaminocarbonyl, Cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl, cyclohexylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,
Allylaminocarbonyl, Pentafluorthio, Methoxydifluormethyl, Ethoxydifluormethyl, n- Propyloxydifluormethyl, Trifluormethoxymethyl, Trifluormethoxyethyl, Allylaminocarbonyl, pentafluorothio, methoxydifluoromethyl, ethoxydifluoromethyl, n-propyloxydifluoromethyl, trifluoromethoxymethyl, trifluoromethoxyethyl,
Trifluormethoxy-n-propyl, Methoxymethyl, Ethoxymethyl, n-Propyloxymethyl, Ethoxy ethyl, Methoxy ethyl, n-Propyloxy ethyl, Methoxy-n-propyl, Ethoxy-n-propyl, 1 - Methoxyeth-l-yl, 1-Methoxyprop-l -yl, 1 -Ethoxy eth- 1-yl, 2-Methoxyprop-2-yl, 2- Ethoxyprop-2-yl, Methylthiomethyl, Methylthioethyl, Methylthio-n-propyl, Ethylthiomethyl, Trifluormethylthiomethyl, Petntafluorethylthiomethyl, Trifluoromethoxy-n-propyl, methoxymethyl, ethoxymethyl, n-propyloxymethyl, ethoxyethyl, methoxyethyl, n-propyloxyethyl, methoxy-n-propyl, ethoxy-n-propyl, 1-methoxyeth-1-yl, 1-methoxyprop-l -yl, 1-ethoxy-eth-1-yl, 2-methoxyprop-2-yl, 2-ethoxyprop-2-yl, methylthiomethyl, methylthioethyl, methylthio-n-propyl, Ethylthiomethyl, trifluoromethylthiomethyl, Petntafluorethylthiomethyl,
Trifluormethylthioethyl, Trifluormethylthio-n-propyl, Methoxycarbonylmethyl, Ethoxycarbonylmethyl, Methoxycarbonylethyl, Ethoxycarbonylethyl, n- Propyloxycarbonylmethyl, tert-Butyloxycarbonylmethyl, tert-Butyloxycarbonylethyl, Hydroxycarbonylmethyl, Hydroxycarbonylethyl, Hydroxycarbonyl,  Trifluoromethylthioethyl, trifluoromethylthio-n-propyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n-propyloxycarbonylmethyl, tert-butyloxycarbonylmethyl, tert-butyloxycarbonylethyl, hydroxycarbonylmethyl, hydroxycarbonylethyl, hydroxycarbonyl,
Methylaminocarbonylmethyl, Ethylaminocarbonylmethyl, n- Propylaminocarbonylmethyl, iso-Propylaminocarbonylmethyl,  Methylaminocarbonylmethyl, ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, iso -propylaminocarbonylmethyl,
Benzylaminocarbonylmethyl, Phenylaminocarbonylmethyl,  Benzylaminocarbonylmethyl, phenylaminocarbonylmethyl,
Cyclopropylaminocarbonylmethyl, Cyclobutylaminocarbonylmethyl,  Cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl,
Cyclopentylaminocarbonylmethyl, Cyclohexylaminocarbonylmethyl,  Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl,
Dimethylaminocarbonylmethyl, Diethylaminocarbonylmethyl,  Dimethylaminocarbonylmethyl, diethylaminocarbonylmethyl,
Allylaminocarbonylmethyl, Methylaminomethyl, Dimethylaminomethyl,  Allylaminocarbonylmethyl, methylaminomethyl, dimethylaminomethyl,
Diethylaminomethyl, Ethylaminomethyl, iso-Propylaminomethyl, n- Propylaminomethyl, n-Butylaminomethyl, Methylaminoethyl, Dimethylaminoethyl, Diethylaminoethyl, N-Pyrrolidinylmethyl, N-Piperidinylmethyl steht,  Diethylaminomethyl, ethylaminomethyl, iso -propylaminomethyl, n-propylaminomethyl, n-butylaminomethyl, methylaminoethyl, dimethylaminoethyl, diethylaminoethyl, N-pyrrolidinylmethyl, N-piperidinylmethyl,
R2 und R6 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n- Butyl, 1-Methyl-prop-l-yl, 2-Methyl-prop-l-yl, n-Pentyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl, Cyanomethyl, 2-Cyanoeth-l-yl, 1-Cyano-eth-l-yl, 3- Cyanoprop-l-yl, Cyclopropylmethyl, Cyclopropylethyl, Cyclobutylmethyl, R 2 and R 6 independently of one another represent hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methyl-prop-1-yl, 2-methyl-prop-1-yl, n-pentyl, Cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyanomethyl, 2-cyanoeth-1-yl, 1-cyanoeth-1-yl, 3-cyanoprop-1-yl, cyclopropylmethyl, cyclopropylethyl, cyclobutylmethyl,
Cyclopentylmethyl, Cyclohexylmethyl, Methylsulfonyl, Ethylsulfonyl, iso- Propylsulfonyl, n-Propylsulfonyl, n-Butylsulfonyl, 1-Methylprop-l-yl, 2-Methylprop-l - yl, 1,1-Dimethyleth-l -ylsulfonyl, Cyclopropylsulfonyl, Cyclobutylsulfonyl,  Cyclopentylmethyl, cyclohexylmethyl, methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsylsulfonyl, cyclopropylsulfonyl, cyclobutylsulfonyl,
Cyclopentylsulfonyl, Cyclohexylsulfonyl, Phenylsulfonyl, p-Cl-Phenylsulfonyl, m-Cl- Phenylsulfonyl, p-Cl-Phenylsulfonyl, p-F-Phenylsulfonyl, m-F-Phenylsulfonyl, p-F- Phenylsulfonyl, p-Cyano-Phenylsulfonyl, m-Cyano-Phenylsulfonyl, p-Cyano- Phenylsulfonyl, p-Methylphenylsulfonyl, m-Methylphenylsulfonyl, p- Methylphenylsulfonyl, p-Trifluormethylphenylsulfonyl, m- Cyclopentylsulfonyl, cyclohexylsulfonyl, phenylsulfonyl, p-Cl-phenylsulfonyl, m-Cl-phenylsulfonyl, p-Cl-phenylsulfonyl, pF-phenylsulfonyl, mF-phenylsulfonyl, pF-phenylsulfonyl, p-cyano-phenylsulfonyl, m-cyano-phenylsulfonyl, p- Cyano-phenylsulfonyl, p-methylphenylsulfonyl, m-methylphenylsulfonyl, p-methylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, m-
Trifluormethylphenylsulfonyl, p-Trifluormethylphenylsulfonyl, Benzylsulfonyl, p-Cl- Phenylmethylsulfonyl, m-Cl-Phenylmethylsulfonyl, p-Cl-Phenylmethylsulfonyl, p-F- Phenylmethylsulfonyl, m-F-Phenylmethylsulfonyl, p-F-Phenylmethylsulfonyl, p-Cyano- Phenylmethylsulfonyl, m-Cyano-Phenylmethylsulfonyl, p-Cyano- Phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, m-Methyl- phenylmethylsulfonyl, p-Methyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, m-Trifluormethyl-phenylmethylsulfonyl, p-Trifluormethyl- phenylmethylsulfonyl, Methylcarbonyl, Ethylcarbonyl, iso-Propylcarbonyl, tert.- Butylcarbonyl, Phenylcarbonyl, p-Cl-Phenylcarbonyl, m-Cl-Phenylcarbonyl, o-Cl- Phenylcarbonyl, p-F-Phenylcarbonyl, m-F-Phenylcarbonyl, o-F-Phenylcarbonyl, Pyridin-2-ylcarbonyl, Pyridin-3-ylcarbonyl, Pyridin-4-ylcarbonyl, 4-Trifluormethyl- pyridin-3-ylcarbonyl, Cyclopropylcarbonyl, Cyclobutylcarbonyl, Cyclopentylcarbonyl, Cyclohexylcarbonyl, Methoxycarbonyl, Ethoxycarbonyl, tert-Butyloxycarbonyl, Benzyloxycarbonyl, Trifluormethylcarbonyl, Difluormethylcarbonyl, Allyl, Propargyl,Trifluoromethylphenylsulfonyl, p-trifluoromethylphenylsulfonyl, benzylsulfonyl, p-Cl-phenylmethylsulfonyl, m-Cl-phenylmethylsulfonyl, p-Cl-phenylmethylsulfonyl, pF-phenylmethylsulfonyl, mF-phenylmethylsulfonyl, pF-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, m-cyano-phenylmethylsulfonyl, p-cyano-phenylmethylsulfonyl, p-methylphenylmethylsulfonyl, m-methylphenylmethylsulfonyl, p-methylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, m-trifluoromethylphenylmethylsulfonyl, p-trifluoromethylphenylmethylsulfonyl, methylcarbonyl, ethylcarbonyl, iso-propylcarbonyl, tert-butylcarbonyl, phenylcarbonyl, p-Cl-phenylcarbonyl, m-Cl-phenylcarbonyl, o-Cl- Phenylcarbonyl, pF-phenylcarbonyl, mF-phenylcarbonyl, oF-phenylcarbonyl, pyridin-2-ylcarbonyl, pyridin-3-ylcarbonyl, pyridin-4-ylcarbonyl, 4-trifluoromethyl-pyridin-3-ylcarbonyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, Methoxycarbonyl, ethoxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, trifluoromethylcarbonyl, difluoromethylcarbonyl, allyl, propargyl,
2,2-Difluorethyl, 3,3,3-Trifluorethyl, Methoxymethyl, Methoxyethyl, Methoxy-n- propyl, Ethoxyethyl, Ethoxymethyl, Ethoxy-n-propyl, Amino, Methylaminocarbonyl, Ethylaminocarbonyl, Dimethylaminocarbonyl stehen, R3, R4, R7 und R8 unabhängig voneinander für Wasserstoff, Methyl, Ethyl, n-Propyl, iso-Propyl, n-Butyl, 1-Methylprop-l-yl, 2-Methylprop-l-yl, tert-Butyl, Trifluormethyl, 2,2-difluoroethyl, 3,3,3-trifluoroethyl, methoxymethyl, methoxyethyl, methoxy-n-propyl, ethoxyethyl, ethoxymethyl, ethoxy-n-propyl, amino, methylaminocarbonyl, ethylaminocarbonyl, dimethylaminocarbonyl, R 3 , R 4 , R 7 and R 8 independently of one another are hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, 1-methylprop-1-yl, 2-methylprop-1-yl, tert-butyl, trifluoromethyl,
Difluormethyl, Cyclopropyl, Cyclobutyl, Cyclopentyl, Cyclohexyl stehen, m für 0, 1 oder 2 steht, n für 1 , 2 oder 3 steht,  Difluoromethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, m is 0, 1 or 2, n is 1, 2 or 3,
R und R mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R and R with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R7 und R8 mit dem Kohlenstoffatom, an das sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 7 and R 8 with the carbon atom to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R3 und R7 mit den Kohlenstoffatomem, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden, oder R 3 and R 7 form the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, or
R4 und R8 mit den Kohlenstoffatomen, an die sie gebunden sind, einen vollständig gesättigten oder teilgesättigten, gegebenenfalls durch Heteroatome unterbrochenen und gegebenenfalls weiter substituierten 3 bis 10-gliedrigen monocyclischen oder bicyclischen Ring bilden und für Pyridin-2-yl, Pyridin-3-yl, Pyridin-4-yl, Pyrazin-2-yl, Pyridazin-3-yl, Pyridazin-4-yl, Pyrimidin-2-yl, Pyrimidin-5-yl, Pyrimidin-4-yl, Pyridazin-3-ylmethyl, Pyridazin-4- ylmethyl, Pyrimidin-2-ylmethyl, Pyrimidin-5-ylmethyl, Pyrimidin-4-ylmethyl, Pyrazin- 2-ylmethyl, 3-Chlor-Pyrazin-2-yl, 3-Brom-Pyrazin-2-yl, 3-Methoxy-Pyrazin-2-yl, 3- Ethoxy-Pyrazin-2-yl, 3-Trifluormethylpyrazin-2-yl, 3-Cyanopyrazin-2-yl, Naphth-2-yl, Naphth-l-yl, Chinolin-4-yl, Chinolin-6-yl, Chinolin-8-yl, Chinolin-2-yl, Chinoxalin-2- yl, 2-Naphthylmethyl, 1 -Naphthylmethyl, Chinolin-4-ylmethyl, Chinolin-6-ylmethyl, Chinolin-8-ylmethyl, Chinolin-2-ylmethyl, Chinoxalin-2-ylmethyl, Pyrazin-2-ylmethyl, 4-Chloropyridin-2-yl, 3-Chloropyridin-4-yl, 2-Chloropyridin-3-yl, 2-Chloropyridin-4-yl, 2-Chlorpyridin-5-yl, 2,6-Dichlorpyridin-4-yl, 3-Chlorpyridin-5-yl, 3,5-Dichlorpyridin-2- yl, 3-Chlor-5-Trifluormethylpyridin-2-yl, (4-Chloropyridin-2-yl)methyl, (3- Chloropyridin-4-yl)methyl, (2-Chloropyridin-3 -yl)methyl, (2-Chloropyridin-4- yl)methyl, (2-Chlorpyridin-5-yl)methyl, (2,6-Dichlorpyridin-4-yl)methyl, (3- Chlorpyridin-5-yl)methyl, (3,5-Dichlorpyridin-2-yl)methyl, Thiophen-2-yl, Thiophen-3- yl, 5-Methylthiophen-2-yl, 5-Ethylthiophen-2-yl, 5-Chlorthiophen-2-yl, 5- Bromthiophen-2-yl, 4-Methylthiophen-2-yl, 3-Methylthiophen-2-yl, 5-Fluorthiophen-3- yl, 3,5-Dimethylthiophen-2-yl, 3-Ethylthiophen-2-yl, 4,5-Dimethylthiophen-2-yl, 3,4- Dimethylthiophen-2-yl, 4-Chlorthiophen-2-yl, Furan-2-yl, 5-Methylfuran-2-yl, 5- Ethylfuran-2-yl, 5-Methoxycarbonylfuran-2-yl, 5-Chlorfüran-2-yl, 5-Bromfuran-2-yl, Thiophan-2-yl, Thiophan-3-yl, Sulfolan-2-yl, Sulfolan-3-yl, Tetrahydrothiopyran-4-yl, Tetrahydropyran-4-yl, Tetrahydrofuran-2-yl, Tetrahydrofuran-3-yl, 2-Phenyleth-l-yl, 1- (4-Methylphenyl)eth-l-yl, l-(3-Methylphenyl)eth-l-yl, l-(2-Methylphenyl)eth-l-yl, 1- (4-Chlorphenyl)eth-l-yl, l-(3-Chlorphenyl)eth-l-yl, l-(2-Chlorphenyl)eth-l-yl, l-(4- Trifluormethylphenyl)eth- 1 -yl, 1 -(3 -Trifluormethylphenyl)eth- 1 -yl, 1 -(2- Trifluormethylphenyl)eth-l-yl, l-(4-Fluorphenyl)eth-l -yl, l-(3-Fluorphenyl)eth-l-yl, 1- (2-Fluorphenyl)eth-l-yl, l-(4-Cyanophenyl)eth-l-yl, l-(3-Cyanophenyl)eth-l-yl, l-(2- Cyanophenyl)eth-l-yl, 2-(3-Fluorphenyl)eth-l-yl, 2-(4-Fluorphenyl)eth-l-yl, 2-(2- Fluorphenyl)eth-l-yl, 2-(2-Chlorphenyl)eth-l -yl, 2-(3-Chlorphenyl)eth-l-yl, 2-(4- Chlorphenyl)eth-l-yl, 2-(2-Bromphenyl)eth-l-yl, 2-(3-Bromphenyl)eth-l-yl, 2-(4- Bromphenyl)eth-l-yl, 2-(2-Cyanophenyl)eth-l-yl, 2-(3-Cyanophenyl)eth-l-yl, 2-(4- Cyanophenyl)eth-l-yl, 2-(2-Trifluormethylphenyl)eth- 1 -yl, 2-(3- Trifluormethylphenyl)eth- 1 -yl, 2-(4-Trifluormethylphenyl)eth- 1 -yl, 2-(2- Methoxyphenyl)eth- 1 -yl, 2-(3 -Methoxyphenyl)eth- 1 -yl, 2-(4-Methoxyphenyl)eth- 1 -yl, 2-(4-Methylphenyl)eth-l-yl, 2-(2-Methylphenyl)eth-l-yl, Benzyl, (4- Fluorphenyl)methyl, (3-Fluorphenyl)methyl, (2-Fluorphenyl)methyl, (2,4- Difluorphenyl)methyl, (3,5-Difluorphenyl)methyl, (2,5-Difluorphenyl)methyl, (2,6- Difluorphenyl)methyl, (2,4,5-Trifluorphenyl)methyl, (2,4,6-Trifluorphenyl)methyl, (4- Chlorphenyl)methyl, (3-Chlorphenyl)methyl, (2-Chlorphenyl)methyl, (2,4- Dichlorphenyl)methyl, (3,5-Dichlorphenyl)methyl, (2,5-Dichlorphenyl)methyl, (2,6- Dichlorphenyl)methyl, (2,4,5-Trichlorphenyl)methyl, (2,4,6-Trichlorphenyl)methyl, (4- Bromphenyl)methyl, (3-Bromphenyl)methyl, (2-Bromphenyl)methyl, (4- Iodphenyl)methyl, (3-Iodphenyl)methyl, (2-Iodphenyl)methyl, (3-Chlor-5- Trifluormethyl-pyridin-2-yl)methyl, (2-Brom-4-Fluorphenl)methyl, (2-Brom-4- Chlorphenyl)methyl, (3 -Brom-4-Fluorphenyl)methyl, (3 -Brom-4-Chlorphenyl)methyl, (3-Brom-5-Fluorphenyl)methyl, (3-Brom-5-Chlorphenyl)methyl, (2-Fluor-4- Bromphenyl)methyl, (2-Chlor-4-Bromphenyl)methyl, (3 -Fluor-4-Bromphenyl)methyl, (3-Chlor-4-Bromphenyl)methyl, (2-Chlor-4-Fluorphenyl)methyl, (3-Chlor-4- Fluorphenyl)methyl, (2-Fluor-3 -Chlorphenyl)methyl, (2-Fluor-4-Chlorphenyl)methyl, (2-Fluor-5-Chlorphenyl)methyl, (3-Fluor-4-Chlorphenyl)methyl, (3-Fluor-5- Chlorphenyl)methyl, (2-Fluor-6-Chlorphenyl)methyl, 1-Phenyleth-l-yl, 3,5- Dfluorpyridin-2-yl, (3,6-Dichlor-pyridin-2-yl)methyl, (4-Trifluormethylphenyl)methyl, (3-Trifluormethylphenyl)methyl, (2-Trifluormethylphenyl)methyl, (4- Ethylphenyl)methyl, (3-Ethylphenyl)methyl, (2-Ethylphenyl)methyl, (4- Trifluormethoxyphenyl)methyl, (3-Trifluormethoxyphenyl)methyl, (2- Trifluormethoxyphenyl)methyl, (4-Methoxyphenyl)methyl, (3 -Methoxyphenyl)methyl, (2-Methoxyphenyl)methyl, (4-Methylphenyl)methyl, (3-Methylphenyl)methyl, (2- Methylphenyl)methyl, (4-Cyanophenyl)methyl, (3-Cyanophenyl)methyl, (2- Cyanophenyl)methyl, (2,4-Diethylphenyl)methyl, (3,5-Diethylphenyl)methyl, (3,4- Dimethylphenyl)methyl, (3,5-Dimethoxyphenyl)methyl, 1-Phenyleth-l -yl, l-(2,4- Dichlorphenyl)eth- 1 -yl, 2-(5-Chlor-2-fluorphenyl)eth- 1 -yl, 2-(4-Chlor-2- fluorphenyl)eth- 1 -yl, 2-(2-Chlor-4-fluorphenyl)eth- 1 -yl, 2-(2-Chlor-5-fluorphenyl)eth-R 4 and R 8 with the carbon atoms to which they are attached form a fully saturated or partially saturated, optionally interrupted by heteroatoms and optionally further substituted 3 to 10-membered monocyclic or bicyclic ring, and for pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-5-yl, pyrimidine 4-yl, pyridazin-3-ylmethyl, pyridazin-4-ylmethyl, pyrimidin-2-ylmethyl, pyrimidin-5-ylmethyl, pyrimidin-4-ylmethyl, pyrazine-2-ylmethyl, 3-chloro-pyrazine-2-yl , 3-bromo-pyrazino-2-yl, 3-methoxy-pyrazino-2-yl, 3-ethoxy-pyrazino-2-yl, 3-trifluoromethylpyrazino-2-yl, 3-cyanopyrazino-2-yl, naphtho-2 -yl, naphth-1-yl, quinolin-4-yl, quinolin-6-yl, quinolin-8-yl, quinolin-2-yl, quinoxalin-2-yl, 2-naphthylmethyl, 1-naphthylmethyl, quinoline-4 -ylmethyl, quinolin-6-ylmethyl, quinolin-8-ylmethyl, quinolin-2-ylmethyl, quinoxalin-2-ylmethyl, pyrazine-2-ylmethyl, 4-chloropyridin-2-yl, 3-chloropyridin-4-yl, 2 -Chloropyridin-3-yl, 2-chloropyridin-4-yl, 2-chloropyridin-5-yl, 2,6-dichloropyridin-4-yl, 3-chloropyridin-5-yl, 3,5-dichloropyridin-2-yl , 3-Chloro-5-trifluoromethylpyridin-2-yl, (4-chloropyridin-2-yl) methyl, (3-chloropyridin-4-yl) methyl, (2-chloropyridin-3-yl) methyl, (2-Chl oropyridin-4-yl) methyl, (2-chloropyridin-5-yl) methyl, (2,6-dichloropyridin-4-yl) methyl, (3-chloropyridin-5-yl) methyl, (3,5-dichloropyridine) 2-yl) methyl, thiophen-2-yl, thiophen-3-yl, 5-methylthiophene-2-yl, 5-ethylthiophene-2-yl, 5-chlorothiophene-2-yl, 5-bromothiophene-2-yl, 4-methylthiophene-2-yl, 3-methylthiophene-2-yl, 5-fluorothiophene-3-yl, 3,5-dimethylthiophene-2-yl, 3-ethylthiophene-2-yl, 4,5-dimethylthiophene-2 yl, 3,4-dimethylthiophene-2-yl, 4-chlorothiophene-2-yl, furan-2-yl, 5-methyl-furan-2-yl, 5-ethyl-furan-2-yl, 5-methoxycarbonyl-furan-2-yl, 5-chlorofuran-2-yl, 5-bromofuran-2-yl, thiophan-2-yl, thiophan-3-yl, sulfolan-2-yl, sulfolan-3-yl, tetrahydrothiopyran-4-yl, tetrahydropyran-4 yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, 2-phenyleth-1-yl, 1- (4-methylphenyl) eth-1-yl, 1- (3-methylphenyl) eth-1-yl, (2-methylphenyl) eth-1-yl, 1- (4-chlorophenyl) eth-1-yl, 1- (3-chlorophenyl) eth-1-yl, 1- (2-chlorophenyl) eth-1-yl, 1- (4-trifluoromethylphenyl) eth-1-yl, 1- (3-trifluoromethylphenyl) eth-1-yl, 1- (2-trifluoromethylphenyl) eth-1-yl, 1- (4-fluorophenyl) eth-1-yl, 1- (3-fluorophenyl) eth-1-yl, 1- (2-fluorophenyl) eth-1-one yl, 1- (4-cyanophenyl) eth-1-yl, 1- (3-cyanophenyl) eth-1-yl, 1- (2-cyanophenyl) eth-1-yl, 2- (3-fluorophenyl) ethane 1-yl, 2- (4-fluorophenyl) eth-1-yl, 2- (2-fluorophenyl) eth-1-yl, 2- (2-chlorophenyl) eth-1-yl, 2- (3-chlorophenyl) eth-1-yl, 2- (4-chlorophenyl) eth-1-yl, 2- (2-bromophenyl) eth-1-yl, 2- (3-bromophenyl) eth-1-yl, 2- (4- Bromophenyl) eth-1-yl, 2- (2-cyanophenyl) eth-1-yl, 2- (3-cyanophenyl) eth-1-yl, 2- (4-cyanophenyl) eth-1-yl, 2- 2-trifluoromethylphenyl) eth-1-yl, 2- (3-trifluoromethyl-phenyl) -eth-1-yl, 2- (4-trifluoromethyl-phenyl) -eth-1-yl, 2- (2-methoxyphenyl) -eth-1-yl, 2 - (3-methoxyphenyl) eth-1-yl, 2- (4-methoxyphenyl) eth-1-yl, 2- (4-methyl-phenyl) -eth-1-yl, 2- (2-methyl-phenyl) -eth-1-yl , Benzyl, (4-fluorophenyl) methyl, (3-fluorophenyl) methyl, (2-fluorophenyl) methyl, (2,4-difluorophenyl) methyl, (3,5-difluorophenyl) methyl, (2,5-difluorophenyl) methyl , (2,6-difluorophenyl) methyl, (2,4,5-trifluoroph enyl) methyl, (2,4,6-trifluorophenyl) methyl, (4- Chlorophenyl) methyl, (3-chlorophenyl) methyl, (2-chlorophenyl) methyl, (2,4-dichlorophenyl) methyl, (3,5-dichlorophenyl) methyl, (2,5-dichlorophenyl) methyl, (2,6- Dichlorophenyl) methyl, (2,4,5-trichlorophenyl) methyl, (2,4,6-trichlorophenyl) methyl, (4-bromophenyl) methyl, (3-bromophenyl) methyl, (2-bromophenyl) -methyl, (4- Iodophenyl) methyl, (3-iodophenyl) methyl, (2-iodophenyl) methyl, (3-chloro-5-trifluoromethylpyridin-2-yl) methyl, (2-bromo-4-fluorophenol) methyl, (2-bromo 4-chlorophenyl) methyl, (3-bromo-4-fluorophenyl) methyl, (3-bromo-4-chlorophenyl) methyl, (3-bromo-5-fluorophenyl) methyl, (3-bromo-5-chlorophenyl) methyl , (2-fluoro-4-bromophenyl) methyl, (2-chloro-4-bromophenyl) methyl, (3-fluoro-4-bromophenyl) methyl, (3-chloro-4-bromophenyl) methyl, (2-chloro) 4-fluorophenyl) methyl, (3-chloro-4-fluorophenyl) methyl, (2-fluoro-3-chlorophenyl) methyl, (2-fluoro-4-chlorophenyl) methyl, (2-fluoro-5-chlorophenyl) methyl, (3-Fluoro-4-chlorophenyl) methyl, (3-fluoro-5-chlorophenyl) methyl, (2-fluoro-6-chlorophenyl) methyl, 1-phenyleth-1-yl, 3,5-D-fluorop yridin-2-yl, (3,6-dichloropyridin-2-yl) methyl, (4-trifluoromethylphenyl) methyl, (3-trifluoromethylphenyl) methyl, (2-trifluoromethylphenyl) methyl, (4-ethylphenyl) methyl, ( 3-ethylphenyl) methyl, (2-ethylphenyl) methyl, (4-trifluoromethoxyphenyl) methyl, (3-trifluoromethoxyphenyl) methyl, (2-trifluoromethoxyphenyl) methyl, (4-methoxyphenyl) methyl, (3-methoxyphenyl) methyl, (2 -Methoxyphenyl) methyl, (4-methylphenyl) methyl, (3-methylphenyl) methyl, (2-methylphenyl) methyl, (4-cyanophenyl) methyl, (3-cyanophenyl) methyl, (2-cyanophenyl) methyl, (2, 4-diethylphenyl) methyl, (3,5-diethylphenyl) methyl, (3,4-dimethylphenyl) methyl, (3,5-dimethoxyphenyl) methyl, 1-phenyleth-1-yl, 1- (2,4-dichlorophenyl) eth-1-yl, 2- (5-chloro-2-fluorophenyl) eth-1-yl, 2- (4-chloro-2-fluorophenyl) eth-1-yl, 2- (2-chloro-4-fluorophenyl ) eth-1-yl, 2- (2-chloro-5-fluorophenyl) ethane
1- yl, 2-(3-Chlor-2-fluorphenyl)eth-l -yl, 2-(3-Chlor-4-fluorphenyl)eth-l-yl, 2-(3-Chlor- 5-fluorphenyl)eth- 1 -yl, 2-(4-Chlor-3 -fluorphenyl)eth- 1 -yl, 2-(2-Chlor-6- fluorphenyl)eth-l-yl, l,3-Thiazol-2-yl, 4-Methyl-l,3-thiazol-2-yl, l,3-Thiazol-2-yl, 1- Methyl-imidazol-4-yl, 1 -Methyl- imidazo 1-5 -yl, 1 -Ethyl-imidazol-4-yl, 1-Ethyl- imidazol-5-yl, l-iso-Propyl-imidazol-4-yl, l-iso-Propyl-imidazol-5-yl, 4- (Methylcarbonylamino)phenylmethyl, 4-(iso-Propylcarbonylamino)phenylmethyl,4- (cyclo-Propylamino)phenylmethyl, 2-(2,6-Difluorphenyl)eth- 1 -yl, 2-(2,5- Difluorphenyl)eth-l-yl , 2-(2,4-Difluorphenyl)eth-l -yl, 2-(2,6-Dichlorphenyl)eth-l-yl,1-yl, 2- (3-chloro-2-fluorophenyl) eth-1-yl, 2- (3-chloro-4-fluorophenyl) eth-1-yl, 2- (3-chloro-5-fluorophenyl) eth - 1 -yl, 2- (4-chloro-3-fluorophenyl) eth-1-yl, 2- (2-chloro-6-fluorophenyl) eth-1-yl, l, 3-thiazol-2-yl, 4 -Methyl-l, 3-thiazol-2-yl, l, 3-thiazol-2-yl, 1-methyl-imidazol-4-yl, 1-methylimidazo-1-5-yl, 1-ethyl-imidazole 4-yl, 1-ethyl-imidazol-5-yl, 1-iso-propyl-imidazol-4-yl, 1-iso-propyl-imidazol-5-yl, 4- (methylcarbonylamino) phenylmethyl, 4- (iso- Propylcarbonylamino) phenylmethyl, 4- (cyclopropylamino) phenylmethyl, 2- (2,6-difluorophenyl) eth-1-yl, 2- (2,5-difluorophenyl) eth-1-yl, 2- (2,4- Difluorophenyl) eth-1-yl, 2- (2,6-dichlorophenyl) eth-1-yl,
2- (2,5-Dichlorphenyl)eth-l-yl , 2-(2,4-Dichlorphenyl)eth-l-yl, 2-(2,3- Dichlorphenyl)eth-l-yl, 2-(3,5-Dichlorphenyl)eth-l-yl, 2-(4-Nitrophenyl)eth-l-yl, 2-(2- Nitrophenyl)eth-l-yl steht. 2- (2,5-dichlorophenyl) eth-1-yl, 2- (2,4-dichlorophenyl) eth-1-yl, 2- (2,3-dichlorophenyl) eth-1-yl, 2- (3, 5-dichlorophenyl) eth-1-yl, 2- (4-nitrophenyl) eth-1-yl, 2- (2-nitrophenyl) eth-1-yl.
15. Sprühlösung zur Behandlung von Pflanzen, enthaltend eine zur Steigerung der 15. Spraying solution for the treatment of plants, containing one for increasing the
Widerstandsfähigkeit von Pflanzen gegenüber abiotischen Stressfaktoren wirksame Menge oder mehrerer der substituierten N-Sulfonyl-N'-aryldiaminoalkane  Resistance of plants to abiotic stress factors effective amount or more of the substituted N-sulfonyl-N'-aryldiaminoalkane
und N-Sulfonyl-N'- heteroaryldiammoalkane gemäß einem der Ansprüche 12, 13 oder 14.  and N-sulfonyl-N'-heteroaryldiammoalkanes according to one of claims 12, 13 or 14.
PCT/EP2018/068975 2017-07-31 2018-07-12 Use of substituted n-sulfonyl-n'-aryl diaminoalkanes and n-sulfonyl-n'-heteroaryl diaminoalkanes or salts thereof for increasing the stress tolerance in plants WO2019025153A1 (en)

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