Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/12—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/14—Sulfonamides having sulfur atoms of sulfonamide groups bound to carbon atoms of rings other than six-membered aromatic rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/15—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/22—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/22—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/22—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/30—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/30—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/48—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
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
  • C07C311/51—Y being a hydrogen or a carbon atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • 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
  • C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
  • C07C311/52—Y being a hetero atom
  • C07C311/53—X and Y not being nitrogen atoms, e.g. N-sulfonylcarbamic acid
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—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
  • C07D213/02—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
  • C07D213/04—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
  • 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
  • C07D213/32—Sulfur atoms
  • C07D213/34—Sulfur atoms to which a second hetero atom is attached
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—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
  • C07D213/02—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
  • C07D213/04—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
  • 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
  • C07D213/61—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—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
  • C07D213/02—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
  • C07D213/04—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
  • 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
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/70—Sulfur atoms
  • C07D213/71—Sulfur atoms to which a second hetero atom is attached
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
  • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
  • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D215/36—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
  • C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
  • C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
  • C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members 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
  • C07D241/16—Halogen atoms; Nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
  • C07D241/36—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems
  • C07D241/38—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings condensed with carbocyclic rings or ring systems with only hydrogen or carbon atoms directly attached to the ring nitrogen atoms
  • C07D241/40—Benzopyrazines
  • C07D241/42—Benzopyrazines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
  • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
  • C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
  • C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
  • C07D307/64—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
  • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
  • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
  • C07D333/30—Hetero atoms other than halogen
  • C07D333/34—Sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/04—Systems containing only non-condensed rings with a four-membered ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
  • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C2601/00—Systems containing only non-condensed rings
  • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
  • C07C2601/14—The ring being saturated

Definitions

• 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.
• 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.
• certain aryl- and heteroaryl-substituted sulfonamides can be used as active ingredients against abiotic plant stress (see WO 2011/113861).
• substituted arylsulfonamides cf., for example, WO 2009/105774, WO 2006/124875, WO 96/36595
• substituted hetarylsulfonamides cf., WO 2009/113600, WO 2007/122219
• 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
• urokinase inhibitors see WO 2000/05214
• active ingredients for the treatment of diabetes see WO 2003/091211
• analgesics see WO 2008/131947
• ⁇ -secretase modulators see WO 2010/108067
• 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 .
• signal transduction chains eg transcription factors, kinases, phosphatases
• physiological response of the plant cell eg ion transport, detoxification of reactive oxygen species.
• signal chain genes of the abiotic stress response include transcription factors, kinases, phosphatases
• LSA Proteins Embryogenesis Abundant Proteins
• dehydrins as an important class
• ROS reactive oxygen species
• HSF Heat Shock Factors
• HSP Heat Shock Proteins
• Naphthylsulfamidocarboxylic acid N - [(4-bromo-1-naphthyl) sulfonyl] -5-methoxynorvaline
• 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).
• the molecular causes of the anti-stress effects of these substances are largely unknown.
• PARP poly-ADP-ribose polymerases
• PARG poly (ADP-ribose) glycohydrolases
• the object of the present invention to provide compounds which further increase the tolerance to abiotic stress in plants, a strengthening of the
• Plant growth and / or contribute to increase the plant yield Plant growth and / or contribute to increase the plant yield.
• 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.
• Plant yield can be used.
• 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,
• 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 is cyano, halogen, (C 1 -C 8 ) -alkyl, OR 12 , (C 1 -C 10) -haloalkyl, (C 1 -C 8 ) -haloalkoxy,
• 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
• 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,
• R 3, R 4, R 7 and R 8 independently represent hydrogen, (Ci-C 8) alkyl, (C 2 -C 8) alkenyl, halogen,
• 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
• 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,
• 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,
• 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
• 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
• 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 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
• R 5 is amino, (Ci-C 8) -alkyl, (C 3 -C 8) -cycloalkyl, (C3-C8) -cycloalkyl- (Ci-C8) alkyl, (Ci-C 8) -
• R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 8 ) -alkyl,
• the compounds of general formula (I) can be prepared by addition of a suitable organic compound.
• 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.
• 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.
• Sulfonklareamide 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
• Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine and pyridine and ammonium, alkali or
• Potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular alkali metal salts or
• Alkaline earth metal salts 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
• 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 such as (Ci-C4) -trialkylsulfonium and (Ci-C4) -Trialkylsulfoxoniumsalze.
• 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 is cyano, halogen, (C 1 -C 4) -alkyl, OR 12 , (C 1 -C 4) -haloalkyl, (C 1 -C 4) -haloalkoxy,
• 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
• (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- (
• R 3 and R 4 with the carbon atom to which they are attached, a fully saturated 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,
• 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,
• 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
• 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 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
• 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
• 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,
• (Ci-C7) alkyl 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
• 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 is cyano, halogen, (C 1 -C 6 ) -alkyl, OR 12 , (C 1 -C 6 ) -haloalkyl, (C 1 -C 6 ) -haloalkoxy,
• 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, (C
• 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,
• 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
• R 7 and R 8 with the carbon atom to which they are attached, a fully saturated 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,
• 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 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
• 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 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
• R 5 is amino, (Ci-C 6) -alkyl, (C 3 -C 6) -cycloalkyl, (C3-C6) cycloalkyl (Ci-C 6) alkyl, (Ci-C 6) -
• 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) cycloal
• 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,
• 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- (
• 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,
• Methylaminocarbonyloxy ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy,
• Cyclohexylmethyl trifluoromethyl, pentafluoroethyl, 1,1,2,2-tetrafluoroethyl, heptafluoro-n-propyl, heptafluoro-isopropyl, nonafluorobutyl, chlorodifluoromethyl, bromodifluoromethyl, dichlorofluoromethyl, iododifluoromethyl, bromofluoromethyl, 1-fluoroethyl, 2-fluoroethyl,
• Fluoromethyl difluoromethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, difluoro-tert-butyl,
• Chloromethyl bromomethyl, fluoromethyl, 3,3,3-trifluoro-n-propyl, methoxycarbonyl,
• Ethoxycarbonyl iso-propyloxycarbonyl, n-propyloxycarbonyl, n-butyloxycarbonyl, tert-butyloxycarbonyl, benzyloxycarbonyl, allyloxycarbonyl, methylaminocarbonyl,
• Methylaminosulfonylamino dimethylaminosulfonylamino, ethylaminosulfonylamino, diethylaminosulfonylamino, iso-propylaminosulfonylamino, cyclopropylaminosulfonylamino, cyclobutylaminosulfonylamino, cyclopentylaminosulfonylamino,
• 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,
• Cyclohexylmethyl methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsulfonyl,
• Difluoromethylcarbonyl allyl, propargyl, 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 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,
• Ethoxycarbonyl ior-propyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl, allyloxycarbonyl, benzyloxycarbonyl, dimethylaminocarbonyl, aminocarbonyl,
• Cyclopentylaminocarbonylmethyl cyclohexylaminocarbonylmethyl, 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 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
• 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,
• 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,
• 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
• 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
• 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
• 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
• 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-
• 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 .
• 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
• 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, (
• 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,
• 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-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 (
• R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
• R 7 and R 8 with the carbon atom to which they are attached, a fully saturated 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,
• R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
• R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 8) -alkyl, heteroaryl- (C 1 -C 8) -alkyl, heterocyclyl- (C 1 -C 6) -alkyl,
• R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 8) -alkyl,
• 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, heteroary
• 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-C
• Preferred further subject of the invention are compounds of general formula (I) wherein
• 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
• 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
• Cycloalkylaminosulfonylamino tris - [(C 1 -C 7 ) -alkyl] silyl, bis - [(C 1 -C 7 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 7 ) -alkyl] silyl,
• 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,
• 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 ) -al
• R 10 is R u N- (C 1 -C 7) -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, a fully saturated or
• R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
• R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
• R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 7 ) -alkyl, heteroaryl- (C 1 -C 7 ) -alkyl, heterocyclyl- (C 1 -C 7 ) -alkyl,
• R 10 and R 11 are identical or different and independently of one another represent hydrogen, (C 1 -C 7) -alkyl,
• 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-
• 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
• 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
• 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 )
• Cycloalkylaminosulfonylamino tris - [(C 1 -C 6 ) -alkyl] silyl, bis - [(C 1 -C 6 ) -alkyl] (aryl) silyl, bis-aryl [(C 1 -C 6 ) -alkyl] silyl,
• 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,
• 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 ) alky
• R and R with the carbon atom to which they are attached, a fully saturated or
• R 7 and R 8 with the carbon atom to which they are attached, a fully saturated 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,
• R 4 and R 8 with the carbon atoms to which they are attached, a fully saturated or
• R 5 represents heteroaryl, heterocyclyl, aryl- (C 1 -C 6 ) -alkyl, heteroaryl- (C 1 -C 6 ) -alkyl, heterocyclyl- (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,
• 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
• 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
• 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
• R 1 is hydrogen, fluorine, chlorine, bromine, iodine, cyano, nitro, hydroxy, amino, methylamino,
• Ethylamino dimethylamino, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, methoxycarbonylmethylamino, methoxycarbonylethylamino,
• Methylaminocarbonyloxy ethylaminocarbonyloxy, n-propylaminocarbonyloxy, isopropylaminocarbonyloxy, benzylaminocarbonyloxy, phenylaminocarbonyloxy,
• Ethoxycarbonyl iso-propyloxycarbonyl, n-propyloxycarbonyl, tert-butyloxycarbonyl,
• Benzyloxycarbonyl allyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n-propylaminocarbonyl, iso -propylaminocarbonyl, benzylaminocarbonyl, phenylaminocarbonyl, cyclopropylaminocarbonyl, cyclobutylaminocarbonyl, cyclopentylaminocarbonyl,
• Methylaminocarbonylmethyl ethylaminocarbonylmethyl, n-propylaminocarbonylmethyl, iso-propylaminocarbonylmethyl, benzylaminocarbonylmethyl, phenylaminocarbonylmethyl, cyclopropylaminocarbonylmethyl, cyclobutylaminocarbonylmethyl, Cyclopentylaminocarbonylmethyl, cyclohexylaminocarbonylmethyl,
• 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,
• Cyclohexylmethyl methylsulfonyl, ethylsulfonyl, iso -propylsulfonyl, n-propylsulfonyl, n-butylsulfonyl, 1-methylprop-1-yl, 2-methylprop-1-yl, 1,1-dimethyleth-1-ylsulfonyl,
• Difluoromethylcarbonyl allyl, propargyl, 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 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,
• R 3 and R 4 with the carbon atom to which they are attached, a fully saturated or
• R 7 and R 8 with the carbon atom to which they are attached, a fully saturated or
• 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
• 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
• R 5 is pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrazine-2-yl, pyridazin-3-yl, pyridazin-4-yl,
• 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.
• a composite chemical group such.
• alkyl is therefore also an alkylene group.
• 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
• 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-methylpent
• heteroarylsulfonyl is optionally substituted pyridylsulfonyl
• Heteroarylsulfonyl here in particular optionally substituted quinolinylsulfonyl, for example substituted by fluorine, chlorine, bromine, iodine, cyano, nitro, alkyl, haloalkyl, haloalkoxy, amino, alkylamino, alkylcarbonylamino, dialkylamino or alkoxy groups.
• alkylthio alone or as part of a chemical group - is straight-chain or branched S-alkyl, preferably with 1 to 8, or with 1 to 6
• Carbon atoms such as (Ci-Cio) -, (CI-C ⁇ ) - 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- Dimethylbut
• Alkenylthio in the invention means an alkenyl radical bonded via a sulfur atom
• Alkynylthio represents an alkynyl group bonded through a sulfur atom
• cycloalkylthio represents a cycloalkyl group bonded through a sulfur atom
• cycloalkenylthio represents an above
• Alkylsulfinyl e.g.
• 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-methyl
• 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-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
• cycloalkenyloxy means a cycloalkenyl radical bonded via an oxygen atom.
• the number of carbon atoms refers to the alkyl radical in the
• the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyl group.
• 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) -
• the number of C atoms here refers to the alkyl radical in the alkylcarbonyloxy group.
• the number of C atoms refers to the alkenyl or alkynyl radical in the alkenyl or alkynylcarbonyloxy group.
• aryl means an optionally substituted mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
• optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, 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]
• Alkylaminocarbonyl cycloalkylaminocarbonyl, bis-alkylaminocarbonyl, heteroarylalkoxy,
• heterocyclic radical contains at least one heterocyclic ring
• heterocyclic ring in which at least one C atom is replaced by a heteroatom, preferably by a heteroatom from the group N, O, S, P
• N, O, S, P saturated, unsaturated, partially saturated or heteroaromatic and may be unsubstituted or substituted, wherein the binding site is located on a ring atom.
• heterocyclyl or heterocyclic ring is optionally substituted, it may be fused with other carbocyclic or heterocyclic rings.
• 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.
• optionally substituted heterocyclyl also become
• the heterocyclic ring preferably contains 3 to 9 ring atoms, in particular 3 to 6 ring atoms, and one or more, preferably 1 to 4, in particular 1, 2 or 3 heteroatoms in the heterocyclic ring, preferably from the group N, O, and S, but not two
• Oxygen atoms are 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
• 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.
• 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-
• 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;
• 1,2-dithiin-3 or 4-yl 1,2-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
• 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,
• heterocycles listed above are preferably, for example, hydrogen, halogen, alkyl, haloalkyl, hydroxy, alkoxy, cycloalkoxy, aryloxy, alkoxyalkyl, alkoxyalkoxy, cycloalkyl,
• Alkylaminocarbonyl bis-alkylaminocarbonyl, cycloalkylaminocarbonyl,
• 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.
• 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.
• N (O) and -S (0) groups both enantiomers are included.
• heteroaryl stands for heteroaromatic compounds, ie.
• 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,
• Carbon atoms part of another aromatic ring they are fused heteroaromatic systems, such as benzo-fused or multiply fused heteroaromatic.
• quinolines e.g., quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl
• Isoquinolines e.g., 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
• 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-y
• halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
• alkyl means a straight-chain or branched, open-chain, saturated hydrocarbon radical which is optionally monosubstituted or polysubstituted 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.
• bis also includes the combination of different alkyl radicals, for example, methyl (ethyl) or ethyl (methyl).
• Haloalkyl means by the same or different halogen atoms, partially or fully substituted alkyl, alkenyl and alkynyl, for example monohaloalkyl
• ( 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
• Partially fluorinated haloalkyl means a straight-chain or branched, saturated one
• 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.
• (C 1 -C 4) -alkyl denotes a short notation for straight-chain or branched alkyl having one to four carbon atoms corresponding to the formula
• Range for C atoms 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.
• 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.
• 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
• alkenyl in particular also includes straight-chain or branched open-chain
• Hydrocarbon radicals having more than one double bond such as 1,3-butadienyl and 1,4-pentadienyl, but also allenyl or cumulenyl radicals having one or more 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,
• alkynyl in particular also includes straight-chain or branched open-chain
• 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-
• 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,
• Cycloalkylaminocarbonyl In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on
• 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.
• (C3-Cv) cycloalkyl means a shorthand notation for cycloalkyl of three to seven
• 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 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
• the explanations apply to substituted Corresponding to cycloalkyl.
• Cycloalkylalkyloxy means a cycloalkylalkyl radical bonded via an oxygen atom
• arylalkyloxy means an arylalkyl radical bonded via an oxygen atom
• Alkoxyalkyl means an alkoxy group attached via an alkyl group
• 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 means an alkylthioalkyl radical bonded via an oxygen atom.
• Arylalkoxyalkyl stands for an aryloxy radical bound via an alkyl group
• Heteroaryloxyalkyl means a heteroaryloxy group bonded via an alkyl group.
• Haloalkoxyalkyl means a haloalkoxy radical attached and "haloalkylthioalkyl” means a haloalkylthio radical attached via an alkyl group.
• Arylalkyl means an aryl group attached via an alkyl group
• heteroarylalkyl means a heteroaryl group bonded via an alkyl group
• heterocyclylalkyl means a heterocyclyl group bonded through an alkyl group.
• 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 is an aryl group bonded through an alkenyl group
• heteroarylalkenyl means a heteroaryl group bonded via an alkenyl group
• 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
• heterocyclylalkynyl denotes a heterocyclyl radical bonded via an alkynyl group.
• 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
• Carbon atoms such as (Ci-Cs) -, (CI-C ⁇ ) - 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.
• 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 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.
• 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
• 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.
• 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).
• enantiomers, diastereomers, Z and E isomers are all encompassed by the formula (I).
• diastereomers Z- and E- Isomers
• 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.
• 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.
• the purification can also by
• 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
• 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
• 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).
• 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
• a suitable base eg triethylamine, pyridine or sodium hydroxide
• a suitable solvent eg tetrahydrofuran, acetonitrile, dimethylsulfoxide or dichloromethane
• an optionally substituted Sulfonylchloridvorme with a suitable optionally substituted bromoalkylamine in an intermediate optionally further substituted sulfonylaziridine be transferred.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.
• 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.

Landscapes

• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Plural Heterocyclic Compounds (AREA)

Abstract

Applications Claiming Priority (2)

Publications (1)

Family

ID=59501334

Family Applications (1)

Country Status (1)

Cited By (2)

Citations (204)

• 2018
  • 2018-07-12 WO PCT/EP2018/068975 patent/WO2019025153A1/fr active Application Filing

Patent Citations (215)

Non-Patent Citations (44)

Similar Documents

Legal Events